interviewing-evaluating-candidates

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Help users design and execute a high-signal interview process that prioritizes real-world performance over superficial charisma or pedigree.

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# Interviewing and Evaluating Candidates - Frameworks, Templates & Checklists

*137 artifacts extracted from Lenny's Podcast and Newsletter*

## Frameworks

### 10 Jobs of a PM Interview Framework (My favorite PM interview questions)
A structured interview framework that maps one behavioral/situational question to each of the ten core PM jobs: Impact, Collaboration, Ownership, Leadership, Execution, Strategy, Customer Insights, Vision, Planning, and Communication, plus a bonus Decision Making question. Each question includes specific 'what to look for' criteria and red flags.

How it works: The framework maps 11 questions (10 core + 1 bonus) to PM competency areas:

1. IMPACT: 'What's the most important or impactful product you shipped? What made it so important or impactful?'
   Look for: Significant launch, how they measure impact, how much responsibility they had.
   Flags: Example isn't very important; didn't have much influence.

2. COLLABORATION: 'Tell me about a time you disagreed with an engineer on your team, and how you resolved it.'
   Look for: Convincing with information while preserving relationships; genuinely hearing others out; working backward from shared outcomes.
   Flags: Backing down immediately; railroading others.

3. OWNERSHIP: 'Share a time you shipped a product that failed. Why did it fail and what did you learn? Can you give me one other example?'
   Look for: Ownership of failure; identifying source of failure; lessons that inform current work.
   Flags: Throwing others under the bus; not taking failure seriously.

4. LEADERSHIP: 'Tell me about a time when your team didn't gel. What was the issue, and how did you deal with it? Has this happened on other teams you've been on?'
   Look for: Taking it upon themselves to fix team dynamics; articulating root cause; resolving it.
   Flags: 'It's not my job'; pattern of dysfunctional teams.

5. EXECUTION: 'Pick a project you're proud of that took 3-9 months. Walk me through it from beginning to end. I'll ask questions along the way. [Give this ~7-10 mins]'
   Look for: How they aligned on priorities/success criteria/timeline; dealt with delays/disagreements; kept everyone aligned; kept execs onboard; launch smoothness.
   Flags: Told what to build and just built it; zero issues (likely not honest).

6. STRATEGY: 'Pick a product you worked on in the past year—talk me through your product strategy for it.' [Alt: Take-home to come up with a strategy to 10x growth of existing product.]
   Look for: Excitement/energy; clear, succinct, cohesive strategy; deep insights into the problem.
   Flags: Lack of strategy; hard to follow.

7. CUSTOMER INSIGHTS: 'Tell me about a time you did user research on a product/feature, and that research had a big impact on the product.'
   Look for: Talking to customers before launch; research impacting what they launched; experience with different research modes.
   Flags: Haven't talked to customers; can't think of an example.

8. VISION: 'Tell me the vision for one of your recent projects or teams.'
   Look for: They have a vision; they're excited about it; it's at least somewhat inspiring.
   Flags: Only sharing planned impact or features vs. a vision of the future; no examples.

9. PLANNING: 'How do you get your team to commit to a deadline?'
   Look for: Co-creating deadlines with teammates; using deadlines to motivate/focus vs. forcing endless work; working backward from hard deadlines.
   Flags: Mandating deadlines without involving team; expecting deadlines to be hit or else.

10. COMMUNICATION: [Evaluated through all other questions]
    Look for: Clarity, conciseness, convincingness.
    Flags: Rambling; answers aren't convincing.

11. BONUS - DECISION MAKING: 'What's the biggest one-way-door product decision you've ever had to make?'
    Look for: Decision-making process and inputs; balancing business and user needs; bringing everyone along; de-risking.
    Flags: Working in a silo; relying too heavily on own opinion.

### 25 High-Signal Interview Questions Framework (Grouped by Theme) (How to learn the most about a candidate from a single interview question)
A structured collection of 25 interview questions organized into 5 categories, each with specific evaluation criteria from the leader who recommends it. Designed to maximize signal-to-noise in a 45-minute interview.

How it works: Categories and questions:

**Category 1: How do they handle the hard stuff? (7 questions)**
1. Talk me through your biggest product flop. What happened and what did you do about it? — Look for: brutal honesty about how bad it was and why it failed (Annie Pearl, Microsoft/Calendly)
2. What's the hardest thing you've ever done? — Look for: what 'hard' means to them, how they overcame it, how they worked with others, how much agency they had (Geoff Charles, Ramp)
3. Tell me about a time you've been in a challenging or highly ambiguous situation, and how you navigated that ambiguity. — Look for: seeking structure, seeking help and inputs vs 'this is the way' (JZ, Linktree/Webflow)
4. Describe a time when you were part of a controversial product decision, and what you did. — Look for: ability to represent both sides, even-keeled delivery, taking on different perspectives (Yuhki Yamashita, Figma)
5. Tell me about a time something went wrong. What happened and what did you do about it? — Look for: mindset when things fail, how they relate to evaluating the situation, self-perception during difficulty (Paige Costello, Asana)
6. What is the worst product that you've ever shipped? — Look for: humor, humility, ability to point out mistakes, learning from mistakes (Maggie Crowley, Toast)
7. Tell me about a time when you needed to disagree with your manager or fight for a position against higher leadership. — Look for: backbone + ability to disagree and commit (Ethan Evans, Amazon); influential communication skills, willingness to stand ground (Inbal Shani, GitHub)

**Category 2: How do they think? (4 questions)**
8. What's something that everyone takes for granted that you think is hogwash? — Look for: authenticity, genuine opinions, breaking the 'interview mindset'; can be adapted to domains like AI, management (Nikhyl Singhal, Meta)
9. What's an unfair secret you've learned to improve a product team's velocity and energy level? — Look for: original learnings not from Medium, how they learned and apply it (Noah Weiss, Slack)
10. Tell me about something you did that worked out but not for the reason that you thought it would. — Look for: introspection, reflective decision-making, incorporating learnings into mental models (Ayo Omojola, Carbon Health)
11. What is an experiment you launched that had a very unexpected result? And what did you do after that? — Look for: deep thinking, customer understanding; if result should have been expected based on their description, they're not thinking deeply enough (Hila Qu, growth advisor)

**Category 3: How do they build, ship, and drive impact? (6 questions)**
12. Tell me about your most significant professional accomplishment. — Look for: situation to result, who they influenced, how they influenced, decisions made, roadblocks encountered (Bill Carr, ex-Amazon)
13. Ask about a product they shipped that is NOT cherry-picked by them. — Look for: frameworks not just outcomes, how they build products, how they know if they're going to succeed (Laura Schaffer, Amplitude)
14. What's something that would not exist without your initiative? — Look for: ability to define something specific and tangible; getting startled is a warning sign (Upasna Gautam, CNN)
15. Tell me about a time when you delivered something that was impactful. — Look for: how they define impact, intrinsic motivation about business impact (Lauryn Isford, Notion)
16. Talk about a big problem that you worked on. — Look for: do you feel compelled to work on that problem after hearing them describe it? Tests storytelling and communication (Yuhki Yamashita, Figma)
17. Tell me about a piece of work that you're most proud of. — Look for: taste, judgment, motivations, what good looks like to them, what they like to do (Katie Dill, Stripe; Karri Saarinen, Linear)

**Category 4: Who are they as people? (6 questions)**
18. When I ask people you've worked with about you, what will I hear? What would they say are your superpowers and weaknesses? — Look for: self-awareness calibrated against actual references (people are usually accurate about strengths but not critiques); focus more on superpowers than weaknesses (Andrew Bosworth, Meta CTO)
19. To what do you attribute your success? (Can't say 'luck') — Look for: self-awareness, curiosity, reflection on why they are where they are (Eeke de Milliano, ex-Retool/Stripe)
20. Tell me about something you're really proud of that you accomplished. Take me through the process. — Look for: motivations, work ethic, what they care about, what good looks like (Camille Hearst, Spotify)
21. Fast-forward three years. What's different about you then? — Look for: humility, self-awareness about growth areas; red flag if they default to role/title aspirations only (Ben Williams, growth advisor)
22. Imagine you had a really great day at work and you're telling your partner about it. What are you telling them? — Look for: natural reward mechanisms, highest/best use of the person (Tom Conrad, Zero)
23. What frustrates you the most about where you're working right now? — Look for: what they're running away from, what they couldn't fix, whether they'll encounter the same issue at your company (Nilan Peiris, Wise)

**Category 5: Unexpected curveball questions (2 questions)**
24. A group of scientists have invented a teleportation device. They've hired you as their business counterpart. What two questions do you ask those scientists? — Look for: ability to find Eigenquestions that get to the heart of the problem (Shishir Mehrotra, Coda)
25. What question should I have asked you? — Look for: honest, off-guard answers; the person is an expert in themselves (Christina Wodtke, Stanford)

### 3-Dimensional Talent Evaluation (Oji Udezue)
A framework for assessing candidates and writing job descriptions beyond just technical abilities.

How it works: Evaluates candidates on 1. Skills (technical abilities), 2. Attributes (personality, proclivity, timid vs. bold), 3. Values (principles, ethics).

### 6 Core PM Interview Skills (How to interview product managers)
The six essential skills to evaluate when interviewing IC product managers, distilled from 10 total PM skills

How it works: 1. Communication
2. Collaboration
3. Execution
4. Strategy
5. Impact
6. Product Sense

Note: Product sense isn't typically on PM career ladders but is commonly tested in interviews. These 6 are for IC PMs (not managers).

### 6-Step PM Interview Process (How to interview product managers)
A complete end-to-end PM interview pipeline with recommended durations, pass-through rates, and what to focus on at each step

How it works: Step 1: Recruiter Phone Screen [30 min, optional] — Minimum requirements, expectations, personality fit (not an asshole), timelines. ~50% pass rate.
Step 2: Hiring Manager Phone Screen [30 min] — Get to know the person, discuss the role, test 1-2 most important skills/attributes. ~40-50% pass rate.
Step 3: Full-Day Interview [4-5 hours] — Two parts: (a) Project presentation (done at home or on-site), shared with potential colleagues; (b) 3-6 one-on-one interviews with potential colleagues, each testing a key PM skill.
Step 4: Post-Interview Panel Discussion [30-60 min] — Each interviewer blind votes: Strong No, No, Yes, or Strong Yes. Share votes, discuss, hiring manager decides.
Step 5: Reference Checks — Contact references and backchannel to verify.
Step 6: Make an Offer — Put together compelling offer, share it, and work hard to close.

### Agreeable/Disagreeable vs. Giver/Taker Matrix (Naomi Gleit)
A 2x2 matrix to evaluate team members based on their personality and their core motivations.

How it works: Axes: Agreeable vs. Disagreeable, Giver vs. Taker. Most dangerous employee: Agreeable Taker (nice but self-interested). Most precious employee: Disagreeable Giver (mission-driven but willing to push back and give hard feedback).

### Airbnb Early Hiring Framework (Summary: Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb))
How Airbnb screened and selected early employees to build a mission-driven team

How it works: Two-part hiring screen:
1. Excitement level: How excited is the candidate to be here? This was the #1 priority.
2. Motivation alignment: Understand their true motivations through dedicated 'culture interviews' and ensure they map to the company's core values.

Hiring philosophy:
- Hire diverse backgrounds: former founders, people outside the technology industry
- Diverse backgrounds contribute to better decision-making and a startup-like mindset
- Aim for a feeling of 'a group of friends with a special bond working on a project rather than a job'

### Andrew Bosworth's Superpower vs. Weakness Reference Check Triangulation (How to learn the most about a candidate from a single interview question)
An interview technique that asks candidates to predict what their references will say about their strengths and weaknesses, then triangulates against actual reference checks.

How it works: Question: 'When I ask people you've worked with about you, what will I hear? What would they say are your superpowers and weaknesses?'

Method:
1. Ask the question in the interview
2. Note their predicted strengths and weaknesses
3. Follow up with actual reference checks
4. Compare predictions to reality

Key insight: People are rarely accurate about what critiques others have of them, but they are usually pretty accurate about their strengths.

Evaluation focus: Prioritize understanding superpowers over weaknesses. Ask: 'What is the thing I can hitch a wagon to and ride?' That matters more than downside risk.

Acceptable weakness responses:
- 'You'll hear this critique, I don't think it's fair' (acceptable if they're robust about it)
- 'This is something I'm working on' (shows growth mindset)

### Automattic Work Trial Evaluation Scorecard Areas (Adding a work trial to your interview process)
Categories assessed in Automattic's structured work trial evaluation

How it works: Evaluation is asynchronous and uses scorecards assessing:
1. Core skills needed for the role
2. Communication quality (specifically in a distributed environment)
3. How well they take on constructive feedback throughout the trial
4. Additional nuanced areas tailored to the specific role

Process: Multiple evaluators involved (2-6+ people depending on role), continuous feedback given throughout trial so candidates can adapt and show best work

### Bar Raiser Program (Bill Carr)
A hiring mechanism to ensure objective, high-standard candidate evaluations.

How it works: Requires one designated 'Bar Raiser' per loop who does not report to the hiring manager. They run the debrief meeting, ensure behavioral questions map to objective company principles, and hold technical veto power.

### Candidate Convincing Framework for Work Trials (Adding a work trial to your interview process)
Five strategies from Automattic for getting candidates excited about investing time in a work trial

How it works: Two reasons candidates agree to participate:
1. It's a chance to get to know the company better than a typical interview—especially for distributed/async work
2. The format lets them showcase skills better than interviews—some people are better at doing than interviewing

Five enablers to support candidates:
1. Tailored trial projects: Not live work, but representative; sometimes synthetic, sometimes past challenges
2. Flexibility: Don't expect time off from current job; when/how much time is a conversation, not a mandate; can pause for life events
3. Continuous feedback: Not a take-home—ongoing feedback so candidates can adapt and learn
4. Set clear expectations: From first interview, explain the process, what it entails, time commitments
5. Dedicated Trial Leads: Specialized point of contact who knows the teams and work well

### DoorDash Data Interview Process (Jess Lachs)
A multi-step interview process designed to test both hard and soft skills.

How it works: Includes a technical coding screen followed by a shortened real-world business case where the interviewer intentionally introduces wrong assumptions to test the candidate's reaction, adaptability, and ability to make decisions with imperfect information.

### Drivers vs. Passengers Hiring Framework (How Snowflake builds product)
Snowflake's hiring philosophy for finding high-impact PMs who drive outcomes rather than passively follow

How it works: Core principle: Hire 'drivers' not 'passengers'

What to look for:
- People who get satisfaction from making things happen
- Strong sense of ownership
- Already driving impact and being successful in their current roles
- Adaptability, humbleness, and desire to learn

Interview process:
1. Candidate presentation: Almost every PM interview starts with a presentation from the candidate to the interview team and area leaders. Topic can be anything (often a product they delivered). Evaluates communication skills, passion, and pride in work
2. Values-based evaluation: Evaluate candidates across each of Snowflake's eight core values throughout the process
3. Back-channel references: Before extending an offer, tap into networks for references on candidate's impact and strengths

### Eigenquestion Test for Interviews (How to learn the most about a candidate from a single interview question)
A creative interview technique using a hypothetical scenario (teleportation device) to test whether candidates can quickly identify the one or two most important questions that get to the heart of a problem.

How it works: Prompt: 'A group of scientists have invented a teleportation device. They've hired you to be their business counterpart and bring this to market. What two questions do you ask those scientists?'

Concept: An Eigenquestion is the question that, when answered, most reduces the space of possible answers for all other questions. Sharp product managers and engineers quickly find the 1-2 Eigenquestions on any topic. This is a coded test of that ability.

What to look for: The candidate's two questions should dramatically narrow the problem space and reveal first-principles thinking about what matters most for commercializing a new technology.

### Fellowship Candidate Selection Framework (Meet your Lenny’s Newsletter Fellows ✨)
Lenny's criteria for selecting fellows from a large applicant pool, balancing experience with career upside.

How it works: Selection criteria for a creator-led fellowship:
1. Senior enough to have had firsthand experience building world-class, successful, and impactful products (i.e., real-life lessons to share with others)
2. Not so senior that the fellowship wouldn't meaningfully impact their career trajectory (i.e., meaningful career upside remaining)
3. Strong writing samples
4. Evidence of effort and passion in the application (video submissions, personal messages)
4. Diverse backgrounds across company stages (startup founders, big tech leaders, coaches/consultants)

Evaluation method: Read every application, watch every video, review every writing sample personally. Profile emerged through the process rather than being rigidly defined upfront.

### First-Round Interview Time Breakdown (How to pass any first-round interview (even in a terrible talent market))
The standard time allocation for a first-round tech interview from the employer's perspective

How it works: Standard breakdown:
- 10% intro
- 70% questions from the interviewer
- 20% questions from the candidate

For a 45-minute interview:
- 3-5 minutes intros
- 35 minutes questions from interviewer
- 5-7 minutes questions from candidate

Most first-round interviews are:
- 30 minutes to 1 hour
- Phone or video chat
- One interviewer (not panel)
- Conducted by hiring manager, peer, or someone familiar with the role
- Focused on behavioral questions
- Not comprehensive (1-2 core competencies + culture fit)

### Five-Step Analytical Thinking Interview Framework (The definitive guide to mastering analytical thinking interviews)
A linear flow for structuring a 35-minute analytical thinking interview to maximize signal delivery across all evaluated dimensions

How it works: Five sequential steps with recommended time allocation:

1. **Assumptions and Game Plan** (~1 min): State assumptions to narrow scope, share your game plan for the interview
2. **Product Rationale** (~2-3 min including think time): Articulate product context, market positioning, company-product alignment
3. **Metric Framework** (~12-15 min, largest chunk): Define ecosystem players, map value/actions to metrics, define North Star metric with guardrails
4. **Goal-Setting** (~5 min): Altitude shift from product-level to team-level, pick highest-leverage ecosystem player, score goals on impact and ability to influence
5. **Tradeoff Evaluation** (~10 min): Navigate real-world tradeoff questions by connecting back to mission, metrics, and strategy

Key signals interviewers evaluate: Strategic thinking, Analytical rigor, Structured communication, Decisive recommendations

### Growth Mindset Interview Question (Peter Deng)
Peter's go-to final interview question used across OpenAI, Uber, Instagram, and Airtable to assess growth mindset as the most critical hiring criterion.

How it works: Question: 'Think about one of the biggest mistakes you've made — truly, the more painful the better. Describe the situation, and tell me how you actually think differently now, work differently as a result. How has that turned into a core principle of yours?' Evaluation criteria: Look for genuine vulnerability (not 'I worked too hard'), depth of self-reflection, evidence that the mistake changed actual behavior or principles, passion in recounting. Second-order benefit: if hired, you've already established a relationship baseline of openness and psychological safety.

### Hell Yes or No Hiring Principle (What Seven Years at Airbnb Taught Me About Building a Business)
A simple decision framework for hiring: if you're not excited, don't hire.

How it works: Only hire people you feel 'hell yes' about. If it's a maybe, it's a no. The people you bring in determine the company you become. Reference: https://sivers.org/hellyeah

### Hiring Quality Triangle for Fast-Growth Companies (Ray Cao)
Three key qualities to evaluate when hiring for high-autonomy, fast-growth environments: curiosity, discipline, and ability to prioritize

How it works: Three qualities: (1) Curiosity: Naturally curious about new things, don't get stuck in their own domain. (2) Discipline: Follow guidance on collaboration ('reactive doing'), avoid creating chaos when given broad context. (3) Ability to Prioritize: Nobody can do everything — push the right agenda at the right time. Context: These traits are essential for 'context, no control' culture to work. Without them, broad autonomy creates chaos rather than innovation.

### Home Court / Away Court / Neutral Court Interview Design (Shishir Mehrotra)
A framework for balancing interview questions across three domains to avoid biased evaluation.

How it works: Home Court: Questions about your company/product ('What would you do about X at Coda?'). Risk: Tests if candidate reached same answer as you, not their actual ability. Away Court: Questions about their past work ('How did you solve this?'). Risk: Can't verify difficulty, attribution, or completeness. Neutral Court: Novel problems neither party has worked on (e.g., teleporter question). Safest for evaluation. Recommendation: Majority of interviews should be neutral court. Include a candidate presentation as the away court component — let them upper-bound themselves by presenting whatever they want ('the brag session').

### Interview Brainstorming Exercise for PM Candidates (Vikrama Dhiman)
An interview technique where you pick a product the candidate uses frequently and brainstorm product choices together in a collaborative, deepening conversation

How it works: Process: (1) Pick a product the candidate uses most often — choose one you don't have strong opinions on. (2) Ask: 'What if this product were to do X? Does it make sense?' (3) Go deeper: 'How would it evolve in 6 months? 12 months?' (4) Develop the idea together as a two-way conversation. Look for: Can they abstract out overall product goals? Can they identify users? Do they reason backwards from strategy? Are they obsessed with the feature or what it enables? Are they willing to consider alternative options?

### Interview Question Evaluation Rubric (What to Look For) (How to learn the most about a candidate from a single interview question)
For each of the 25 questions, a specific set of signals and evaluation criteria to determine a strong vs. weak answer. Can be used as a scorecard during interviews.

How it works: Key evaluation signals by category:

**Handling Hard Stuff — Strong signals:**
- Brutal honesty about failures (not deflecting)
- Clear sense of personal agency in overcoming difficulty
- Seeking structure and help through ambiguity (not 'I had all the answers')
- Ability to represent both sides of a controversy evenly
- Humor and humility about mistakes
- Backbone to disagree AND ability to commit after

**Thinking — Strong signals:**
- Genuine, authentic opinions (not rehearsed/predictable)
- Original insights learned from experience (not from blog posts)
- Introspection: reflecting on WHY things worked, incorporating into decision model
- Deep customer understanding revealed through unexpected experiment results

**Building/Shipping/Impact — Strong signals:**
- Can trace situation → actions → influence → decisions → roadblocks → result
- Has frameworks for building, not just outcome stories
- Can name specific tangible things that wouldn't exist without them
- Intrinsic motivation about business impact (not just personal achievement)
- Makes you feel compelled to work on the problem they describe (storytelling test)
- Reveals taste, judgment, and what 'good' means to them

**Who They Are — Strong signals:**
- Self-awareness calibrated with reality (especially about strengths)
- Openness about growth areas without defensiveness
- Natural reward mechanisms align with the role
- Can articulate what they're running from AND toward
- Focuses on personal/professional growth over title/role in 3-year vision

**Red flags across all categories:**
- Only telling you what they think you want to hear
- Unable to name a specific failure or worst product
- Expected experiment results described as 'unexpected'
- Defaulting to title/role aspirations for growth questions
- Unable to define something specific they initiated

### Interview Question for Growth PMs (Summary: The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab))
Hila Qu's go-to interview question for evaluating growth PM and analyst candidates

How it works: Question: 'What is an experiment you launched that had a very unexpected result? And what did you do after that?'

What it reveals:
1. Depth of thinking — how they designed and analyzed the experiment
2. Understanding of customers — why the result was unexpected
3. Approach to failure or unexpected results — how they responded and iterated

This is specifically recommended for growth PMs and analysts, where experimentation mindset is critical.

### Interview Question: Failure Story Assessment (Shweta Shriva)
A senior-level interview question asking candidates to describe a real failure and what they learned, used to assess depth of experience and self-awareness.

How it works: Question: 'Tell me about one time that you failed and what did you learn from it?' Red flags: 1) Candidate says they've never failed. 2) Candidate disguises a success story as a failure. What to look for: Real, solid examples with genuine learning. Signals: Candidates who can't answer authentically are either disingenuous or lack depth of experience.

### Interview Question: High Agency Test (Upasna Gautam)
A single interview question designed to assess whether a candidate demonstrates high agency and initiative

How it works: Question: 'What's something that would not exist without your initiative?' What to look for: Can the candidate define something specific and tangible? The ability to name a concrete contribution is in itself a strong positive signal. No specific 'right answer'—the test is whether they can articulate their unique contribution clearly.

### Interview Question: Solve an Unfamiliar Problem Live with Zapier (Zoelle Egner)
Interview exercise for customer-facing roles where candidates build a Zapier automation live to solve a problem they haven't seen before

How it works: Setup: Present the candidate with an unfamiliar problem you (as a customer) want solved. Ask them to build a solution using Zapier, with internet access allowed. Evaluates: 1) How they respond to unfamiliar/surprising situations (every client will give them one). 2) How they learn things in real-time. 3) How they keep their cool under pressure. Best for: Customer success, solutions engineering, customer-facing technical roles.

### Life Story Interview (Farhan Thawar)
An interview technique focused on understanding the 'why' behind a candidate's resume transitions.

How it works: Don't just ask what they did; ask why they made specific career moves to gauge curiosity, range, and decision-making.

### Linear's Hiring Process for Product Roles (How Linear builds product)
A multi-stage hiring process that evaluates product sense and culminates in a paid work trial.

How it works: What to look for:
- Product sense, taste, and judgment for ALL product roles (engineering, design)
- Ability to form AND articulate opinions on products/features (not just personal preference — must explain rationale)
- For non-product roles: look for adjacent skills beyond role requirements (e.g., storytelling for marketing, user understanding for operations)
- Overall: people who look and care beyond their immediate role

Interview stages:
1. Recruiter screen
2. Hiring manager interview
3. Skills assessment
4. Cross-functional or 'beyond' interviews (e.g., CEO interviews engineers for product thinking)
5. Paid work trial (1-5 days)

Product Thinking Assessment:
- Ask about past product work: 'Did you disagree with something you built at [past company]? Why?'
- Probe whether they can articulate rationale, not just state preferences

Work Trial Details:
- Paid sessions, 1-5 days
- Candidate works on a real project related to their function
- Access granted to: docs, codebase, designs, Slack
- Invited to relevant company and team meetings
- One-on-one chats with team members
- Present work at the end
- Engineers: build a feature from a spec
- Leadership candidates: develop response to a challenge/area prompt

Purpose: Understand how candidates approach problems, handle uncertainty, and communicate. Candidates get a realistic sense of the company and team.

### Little Hands (Meltem Kuran)
A cultural hiring heuristic to ensure candidates are willing to do nitty-gritty, unglamorous work.

How it works: Assess if a leader's first instinct is to do the tiny jobs themselves rather than immediately wanting to hire a team to do it. Essential for early-stage startup hires.

### Nikhyl Singhal's 'Save Question' Technique (How to learn the most about a candidate from a single interview question)
A technique to break candidates out of the 'interview mindset' where they predict what you want to hear, using a question that forces genuine, opinionated responses.

How it works: Core question: 'What's something that everyone takes for granted that you think is hogwash?'

Purpose: Acts as a 'save question' for candidates who may be high-quality but aren't being genuine in the interview. The question forces authenticity because it starts with 'What is the thing that YOU think...'

Variants for different contexts:
- For managers: 'You've managed hundreds of people. What's conventional wisdom about management that you bet against, that you've found is actually inaccurate?'
- For AI roles: 'What do people think about AI that's inaccurate, that everyone believes?'
- For any domain: Adapt the format to domain-specific conventional wisdom

When to use: When you suspect the candidate is giving rehearsed answers and you're at risk of dismissing a genuinely strong candidate.

### Nilan Peiris's 'Running Away From' Assessment (How to learn the most about a candidate from a single interview question)
A technique to understand a candidate's limits and potential fit issues by probing what frustrates them at their current role, rather than why they want to join your company.

How it works: Question: 'What frustrates you the most about where you're working right now?'

Rationale: What candidates are running away from is more interesting than what they say they're running toward. The frustration reveals:
1. Something broken they encountered
2. Something they were unable to fix (their limit)
3. A pattern that may or may not exist at your company

Evaluation: After hearing their frustration, ask yourself: 'Are they going to run into this here every day/every week? Or should they be fine?' Use this as a fit assessment.

### PM Archetypes: Artist, Scientist, General Manager (Nikita Miller)
A framework for evaluating PM talent and building a balanced team.

How it works: Categorizes PMs into three spikes: Artist (creative, design-oriented), Scientist (data-driven, technical), or General Manager (business, execution-oriented). Used in interviews to map candidate strengths against current team gaps.

### PM Interview Project Decision Matrix (How to interview product managers)
A framework for deciding how to deliver and scope the project portion of PM interviews, with pros/cons for each option

How it works: DELIVERY OPTIONS:
Option 1: At Home Before Interview
- Pros: More time to think, closer to real life, gives more interview time during the day
- Cons: Unfair for people with less time outside of work, some people don't like 'working' on their own time, more confounding variables
- ~2/3 of hiring managers prefer this option

Option 2: Day of Interview (e.g. 90 minutes)
- Pros: Equalizes interview conditions, doesn't suck up personal time
- Cons: Less time to think, more pressure, less time for other interviews

PROJECT TOPIC OPTIONS:
Option 1: A real problem you've faced (Lenny's preference — best signal)
Option 2: A hypothetical problem related to your product (most popular)
Option 3: A hypothetical problem unrelated to your product

Majority of hiring managers go with Option 1 or 2.

KEY EVALUATION CRITERIA (what to look for):
- How they break down the problem
- How they structure their solution
- How they communicate it
- NOT how close they got to the right answer
- The discussion afterward is often more valuable than the presentation

### PSHE (Problem, Solution, How, Execution) (Shishir Mehrotra)
A talent evaluation framework that assesses at which level of the problem-solving stack a person operates, replacing scope-based leveling that creates perverse incentives.

How it works: Levels from junior to senior: E (Execution) - Given problem, solution, and how; just execute the playbook. H (How) - Given problem and rough solution; figure out organization, milestones, go-to-market, rituals, meetings. S (Solution) - Given a problem; come back with creative, effective solutions. P (Problem) - Tell us what problems to solve; identify what actually matters. Key insights: 1) Scope is an input (assigned by manager), not an output to evaluate. 2) Mid-career 'trough of dissolution' where evaluation shifts from scope to PSHE is confusing for both employee and manager. 3) P-level thinking is correlated with eigenquestion ability. 4) Applies to all roles including sales (great salespeople are P-level, not just quota-hitters). The relationship between scope and PSHE forms a curve: early career grows in scope at E level, mid-career grows in PSHE, senior career grows in scope at P level.

### Post-Interview Blind Voting Scale (How to interview product managers)
A standardized voting system for post-interview panel discussions to reduce bias

How it works: Each interviewer independently (blind) votes one of four options before any discussion:
1. Strong No
2. No
3. Yes
4. Strong Yes

Process: Vote blind → Share votes → Discuss → Hiring manager makes final decision. The blind voting prevents anchoring bias from senior voices influencing others.

### Red Flags / Green Flags Evaluation Pattern (My favorite PM interview questions)
For each PM interview question, Lenny provides a structured 'What to look for' (green flags) and 'Flags' (red flags) pattern that can be adapted into any interview scorecard.

How it works: Each of the 11 interview questions follows a consistent evaluation structure:
- The question itself (behavioral/situational)
- 'What to look for': 2-5 positive signals indicating strong PM capability in that area
- 'Flags': 1-3 red flag behaviors or responses that indicate weakness

This pattern can be turned into a scorecard where interviewers rate each dimension on a scale (e.g., Strong No / No / Mixed / Yes / Strong Yes) based on whether they observed green flags, red flags, or a mix.

### SPOTAC (Matt MacInnis)
An acronym used to decode a hiring manager's intuition about a candidate.

How it works: Stands for Smart, Passionate, Optimistic, Tenacious, Adaptable, and Kind. Used to pinpoint exactly why a candidate didn't feel like a fit after an interview.

### STAR Method (Bill Carr)
An interviewing technique used to deeply probe a candidate's past professional accomplishments.

How it works: Stands for Situation, Task, Action, Result. Used to spend an entire hour dissecting a single significant professional accomplishment to understand influence, decision-making, and roadblock navigation.

### Spectrum of Product People (Casey Winters)
A model for evaluating PM talent and identifying areas for upskilling.

How it works: Left side: Crazy innovators (lots of ideas, poor execution). Right side: Executional focused (gets things done, lacks industry foresight). Middle: Strategists (the ideal hire who can generate good ideas and execute them).

### T-Shaped Marketer Assessment (Adam Grenier)
An interview exercise for founders to evaluate marketing leaders.

How it works: Identify the candidate's core strength (the vertical bar of the T) and then ask how they compensate for their weaker areas (the horizontal bar), looking for self-awareness and willingness to hire experts to fill gaps.

### The 'Obsession' Interview Question (Kevin Aluwi)
A specific interview question used to gauge passion and structured thinking.

How it works: Ask: 'Tell me about a subject or activity you've been obsessed with for a long time.' Look for: Ability to pitch the obsession, passion for obscure topics, and structured/detailed thinking.

### The 'Un-Cherry-Picked' Interview Question (Laura Schaffer)
An interview tactic to uncover a candidate's true product frameworks rather than their rehearsed success stories.

How it works: Instead of asking 'Tell me about a successful launch,' ask 'Tell me about your most recent ship' or set specific parameters that prevent them from picking their best project. This forces them to discuss their process and frameworks rather than just the positive outcome.

### The 14-Day VP Test (Jason M Lemkin)
An interview question to screen out burnt-out executives who only want to manage process.

How it works: Ask the candidate: 'What do you want to do your first 14 days?' If they say 'work on process, set up Salesforce, or territory planning,' reject them. If they say 'leave me alone, I'm going to go talk to 20 customers,' hire them.

### The Anti-Pitch Interview (Josh Miller)
An interviewing technique where the founder actively tries to talk the candidate out of taking the job.

How it works: The interviewer tells the candidate why most people shouldn't work there and relies entirely on the candidate asking questions ('What would you like to ask me?') to gauge authenticity and conviction.

### Tom Conrad's 'Natural Reward Mechanism' Question (How to learn the most about a candidate from a single interview question)
A question designed to uncover a candidate's intrinsic motivations and highest/best use by asking them to describe their ideal work day in a relatable context.

How it works: Question: 'Imagine you had a really great day at work and you're telling your partner all about it. What are you telling them?'

Purpose: Identifies what the candidate gravitates toward naturally because it rewards them intrinsically. This reveals their 'highest, best use' — the work where they'll be most effective and engaged.

Evaluation: Match their natural reward mechanism to the actual role requirements. The best hires are those whose intrinsic motivations align with what you need them to do.

### Work Trial Realism Spectrum (Adding a work trial to your interview process)
A spectrum for how realistic your work trial should be, from take-home projects to co-working in the real codebase, correlated with company size

How it works: The spectrum ranges from: (1) Take-home assignment with no team interaction and strategic ambiguity (37signals) → (2) Take-home project representative of real work but not actual shipped work (PostHog, Auth0) → (3) Synthetic project using real internal tools with async collaboration (Automattic) → (4) Co-working with future team in actual codebase for 3-5 days (Linear) → (5) Full contractor engagement for 4-6 weeks doing real roadmap work (Gumroad). Key principle: The fewer people you're hiring (and thus the more important each hire is), the more time you should invest in a work trial. As you grow, streamline the process.

## Templates

### 'Tell me about the last time...' Interview Prompt (Petra Wille)
A behavioral interview question format to extract concrete examples of past work.

How it works: Instead of asking theoretical questions, ask 'Tell me about the last time you did your last round of user interviews' or 'Tell me about the last time you onboarded a new colleague'.

### 2-Day Onsite Work Test (Michael Truell)
An interview format for evaluating early-stage startup hires.

How it works: 1. Bring candidate onsite for two full days. 2. Assign a mock project that mirrors real work in the actual codebase (but not production IP). 3. Let them execute end-to-end mostly independently but with some team collaboration. 4. Include multiple meals with the team to test cultural/social fit.

### Almost-Real-Life PM Interview Assignment (How Gong builds product)
A structured assignment-based interview process for PM candidates using real customer pain points and recorded customer conversations

How it works: Assignment structure:
1. Business background: Provide context about the product area and market (see example: pipeline management/collaboration use case).
2. Customer needs: Present real customer pain points with specific details.
3. Conversation snippets: Include recorded customer meeting excerpts so candidates can sense the real need.
4. Open-ended prompt: Ask candidate to show their thought process for how they'd approach the problem.

Design principles (documented by Eilon):
- Simulate working at Gong as closely as possible
- Let candidate experience what working at Gong is like (mutual evaluation)
- Respect candidates' time — completable in hours, not days (target <10 hours, feedback confirms this)
- Invest company's own time to prepare the right assignment
- Make the assignment interesting for the candidate

Evaluation criteria:
- Thought process (more important than the solution itself)
- Interpersonal style during panel discussion
- Balanced approach: discovery vs. solutioning ratio, what to assume vs. leave out
- Customer-centricity: do they enjoy working directly with customers vs. project management?
- Collaboration ability during panel discussion

Panel discussion: Assignment discussed with a panel in the same way any internal proposal would be brainstormed. No 'correct' answer expected.

Key insight: They've hired candidates with poor solutions but great process, and rejected candidates with great solutions who couldn't collaborate or replicate consistently.

### Core Interview Question: Proudest Accomplishment (Gokul Rajaram)
A high-signal interview question to assess how candidates measure their own impact.

How it works: Ask: 'Tell me about a career accomplishment you're most proud of.' Evaluate: Do they talk about shipping a feature, or changing customer behavior? Do they credit the team or just themselves?

### Dashboard/Competitor Redesign Interview Question (Shishir Mehrotra)
A multi-part interview question that progressively tests product thinking from metrics to prioritization to differentiation.

How it works: Sequence: 1) 'Pick your favorite technical product (can't be one you built, worked on, or competed with).' Ask why — this is a passion test. 2) 'Design the one-page dashboard for that product. If you're the CEO/GM, what's on it? Why?' — Tests E-level ability to identify what's important. 3) 'You've been hired by a competitor to build a me-too version. What's the bare minimum to build?' 4) 'You got a quarter of the time and a quarter of the team. What do you actually build?' 5) 'You can differentiate in only one place. What do you do?' This sequence tests PSHE across escalating constraints.

### Director of PM Interview Question Bank — 8 Skill Areas with 24+ Questions (This Week #7: Effectively communicating about a failure to execs, managing founder expectations, and hiring a Director of PM)
A comprehensive set of interview questions organized by the eight key competencies for evaluating Director of Product Management candidates, plus bonus questions

How it works: KEY DIFFERENTIATORS FOR DIRECTOR PM VS. IC PM: (1) Managing PMs, (2) Taking on large scope, (3) Working closely with senior leaders.

1. LONG-TERM STRATEGIC THINKING
   a. Have them pick a 3+ month-long project they've led and are proud of, and walk through it from inception to completion. Jump in to explore strategic thinking at each step.
   b. Present a sample challenge you're facing and have them talk through how they'd tackle it — from vision to strategy to execution.
   c. Give a candidate 2 hours to tackle a challenge on their own at a desk in the office, then present their proposal to the interview panel.

2. PEOPLE LEADERSHIP
   a. 'When I ask them, what would people you've managed in the past say about you? What about your peers?'
   b. 'Tell me about a time you've had to deal with a low-performer. How did you communicate something was wrong? And what did you do to help them improve?'
   c. 'Tell me about a time when a team you were leading didn't gel. Why do you think that happened, and what have you learned?'

3. STAKEHOLDER MANAGEMENT
   a. 'Tell me about a time you took the initiative and made something happen that needed to happen.'
   b. 'Tell me about a time you strongly disagreed with your manager. What did you do to convince them that you were right, and what happened?'
   c. 'Tell me about a time you were behind schedule on a high-visibility project — how did you communicate the news to stakeholders? How'd it go?'

4. IMPACT
   a. 'What measurable impact have you had at your previous companies?'
   b. 'How do you measure the impact of someone in your role?'
   c. 'Say we look back a year from now, what kind of impact would you like to have made?'

5. COMMUNICATION
   a. 'How do you keep your team updated on what's happening higher up in the org?'
   b. 'How do you keep your stakeholders updated on what's happening within your team?'
   c. 'Tell me about a time you messed up communicating something important to either your team or to execs — and what did you learn from that?'

6. DECISION MAKING
   a. 'Tell me about a time you had to make a decision that was counter to what your team wanted. How did you work through that?'
   b. 'When do you wait for consensus vs. making a call yourself?'
   c. 'Tell me about a time when you went against what the data was telling you?'

7. VISION
   a. 'Tell me about a time you had to develop a vision for a product or team.'
   b. 'How important is it to have a vision for your product or team?'
   c. 'What was the vision for your previous product or team?'

8. HIRING
   a. 'Tell me about one of your favorite (or hardest) hiring experiences in the past — how'd you find them, how'd you close them?'
   b. 'How much of your time do you expect to spend hiring?'
   c. 'What's your standard interview loop process?'

BONUS QUESTIONS:
   - 'What's something you're better at than most other people? What's your superpower?'
   - 'What's something you're working to improve?'
   - 'What was your biggest product mistake? What did you learn from it?'

### Empathy Interview Question (Adriel Frederick)
A prompt used to test a candidate's empathy, communication, and ability to read an audience.

How it works: Question: 'Teach me something you don't think I know.' This tests how well the candidate can read the interviewer, their depth of knowledge, and their ability to share information effectively.

### Experiment Design Take-Home Assignment (Crystal W)
A prompt structure for interviewing growth PMs.

How it works: Provide a scenario ('Here is what we see'). Ask: 'How do you know this is true?' and 'Design an experiment.' Give them 5 days to complete ~4 hours of work. Look for random sampling, selection bias awareness, and willingness to research/Google.

### Failure/Success Interview Prompt (Kayvon Beykpour)
An interview question designed to assess a candidate's self-reflection and risk profile.

How it works: Prompt: 'Talk about something you worked on that failed, and talk about something you built that succeeded.' Look for: Why didn't it work? What were the takeaways? Have they actually experienced failure?

### Glen Coates' 4-Question PM Interview (How Shopify builds product)
A simple, repeatable PM interview structure focused on reflection and builder mentality

How it works: Four questions asked in order: 1. Tell me about a product that you were responsible for that went well, and tell me the story of that thing. 2. Tell me about a product that you were responsible for that didn't go well, and tell me the story of that thing. 3. Tell me about a product manager who worked for you that went well [same format]. 4. Tell me about a product manager who worked for you that didn't go well [same format]. What to evaluate: - How the person thinks about what good or bad looks like. - How they reacted when things went wrong. - How insightful their analysis of what they'd do differently is. - In the 'went well' stories: Is there reflection on what could have been better? Are they tortured by imperfections even in successes? - Sheer horsepower and grit. - Tenacious builder mentality. Red flags: Over-reliance on frameworks and processes over substance.

### Growth PM Interview Question (Hila Qu)
A behavioral question to test a growth candidate's analytical depth.

How it works: Question: 'What is an experiment you launched that had a very unexpected result? And what did you do after that?' Looks for evidence of high experiment velocity, deep customer understanding, and ability to learn from failure.

### Introspection Interview Question (Ayo Omojola)
An interview question designed to tease out a candidate's ability to reflect on their decisions and update their mental models.

How it works: Ask: 'Tell me a bad decision that worked out, or a good decision that did not.' Look for candidates who are reflective about why things worked or failed and how they incorporate that into future decisions.

### Linear Work Trial Structure (Adding a work trial to your interview process)
Linear's structured work trial process including meetings, team assembly, and logistics

How it works: Team Assembly:
- Recruiter
- Hiring manager
- 3-5 teammates who would closely intersect with the role

Pre-Trial Logistics:
- Secure NDA
- Grant temporary tool access (GitHub, Figma, Slack, Notion)
- Schedule meetings
- Prep docs with context on goals and expectations

Standard Meetings During Trial:
1. Kickoff: Candidate meets team to review prompt, get context, ask clarifying questions, discuss initial approach
2. Check-in: Candidate-led status update to share progress, ask questions, get feedback (candidate-led to assess ownership and readiness to course-correct)
3. Final Presentation: Candidate presents final deliverable to work trial team, answers questions (discussion-based)

Between meetings: Candidate works on project, can reach out via dedicated Slack channel or ad hoc calls

Evaluation:
- Each team member submits feedback separately without seeing others' comments
- Debrief begins with blind thumbs-up or -down vote
- Open discussion anchored in specific examples and anecdotes
- Anything other than a strong yes is a no
- Hiring manager makes final decision; strong preference for unanimous decisions
- Recruiter documents highlights and key takeaways to share with candidate regardless of outcome

### PM Interview Questions by Skill (How to interview product managers)
Sample behavioral and situational interview questions mapped to each of the 6 core PM skills

How it works: Collaboration: 'Tell me about a time you disagreed with an engineer on your team and how you resolved it.'
Execution: 'Pick a project you're proud of that took 3-9 months. Walk me through it from beginning to end. I'll ask questions along the way.' [Give ~7-10 minutes]
Strategy: 'Pick a product you worked on in the past year—talk me through your strategy for it.'
Customer Insights: 'Tell me about a time you did user research on a product/feature and that research had a big impact on the product.'
Impact: 'What's the most important or impactful product you shipped? What made it so important or impactful? Would it have been as impactful without you, and why?'
Product Sense: 'How would you improve feature x in our product?'

Best practice: Keep questions consistent across candidates with predefined good and bad answers to avoid bias.

### PM Take-Home Assignment Structure (Merci Grace)
A method for evaluating PM candidates using a practical project.

How it works: Provide 3 different real-world problems. Let the candidate pick one. Evaluate based on: quality of the solution, technical feasibility (no 'magic wand' solutions), ability to tell a compelling narrative, and how they would measure success.

### Perspective-Shifting Behavioral Interview Question (John Cutler)
An interview technique to test a candidate's self-awareness and empathy.

How it works: After a candidate answers a standard behavioral question (e.g., 'Tell me about a time you faced adversity'), ask: 'Now imagine you are [Coworker Name mentioned in the story]. How would they answer that same question as it relates to you?'

### PostHog SuperDay Interview Process (Adding a work trial to your interview process)
PostHog's full interview pipeline including the SuperDay work trial format

How it works: Full Process:
1. Culture interview/screening with internal recruiter: 30 minutes
2. Technical interview with team leader + 1-2 team members: 60 minutes
3. Bar-raiser with CEO or CTO: 30 minutes
4. SuperDay work trial: typically 1 day, sometimes 3 days
   - Can split across multiple days (e.g. two half-days) for flexibility
   - 80% task work, 20% coffee chats with 2-3 selected staff
   - Coffee chats serve as additional culture screen + candidate Q&A

Task Design:
- Representative of day-to-day work but NOT actual shipped work
- Open-ended (e.g. build a new product from scratch vs. coding challenges)
- Designed to be too much for one person to complete—tests prioritization
- Example: PM candidate given product scenario to analyze and present

Evaluation:
- Decision within 48 hours
- Decision makers: team lead/hiring manager + both co-founders
- Collect feedback at every stage from everyone involved
- Score out of 4 (4 = strong yes, 3 = soft yes)
- Majority of 'soft yeses' = no (unless passionate advocate exists)
- Rule: hiring wrong person > passing on someone who might have been good

### Proud Accomplishment Interview Question (Camille Hearst)
A behavioral interview question designed to reveal a candidate's work ethic and motivations.

How it works: Question: 'Tell me about something you're really proud of that you accomplished and take me through the process and talk to me about why you're proud of it.' Look for: motivations, work ethic, what they care about, and what 'good' looks like to them.

### Reference Call Question: First Performance Review (Paul Adams)
A specific question to ask during candidate reference calls to get honest, unavoidable feedback.

How it works: Ask the reference: 'What feedback will I be giving this person in their first performance review?'

### Story of Your Career Interview Prompt (Kim Scott)
An open-ended interview question used to assess accountability and depth of experience.

How it works: Prompt: 'Tell me the story of your career.' Follow-up: Double-click into specific accomplishments to verify depth of knowledge. Listen for: How they approach setbacks and if they identify their own mistakes.

### Teach Me Something (Interview Question) (Laura Modi)
An interview question used to assess communication skills, passion, and clarity of thought.

How it works: Ask the candidate: 'Teach me something not related to work.' Look for their ability to take a core concept they understand well (e.g., cooking a perfect steak, the foundation of Latin) and explain it clearly to a novice.

### The $0 / $10k / $100k Interview Question (Meltem Kuran)
A case study prompt used during interviews to test a candidate's resourcefulness and ability to scale.

How it works: Ask the candidate to build a growth strategy with $0, $10,000, and $100,000. Look for their willingness to commit to bottom-funnel revenue metrics even at the $0 tier.

### The 'Hardest Thing' Interview Question (Geoff Charles)
A core interview question used to evaluate a candidate's resilience, agency, and definition of difficulty.

How it works: Question: 'What's the hardest thing you've ever done?' Follow-up probes: What does 'hard' mean to them? Why was it hard? How did they overcome it? How did they work with others? How much agency did they have in the outcome?

### The Passion Interview Question (Maya Prohovnik)
An interview question designed to test a candidate's general passion and enthusiasm.

How it works: Question: 'If you could make a podcast about anything, what would it be?' Red flag: If the candidate cannot think of anything, it indicates a lack of general passion, which is a negative signal for hiring.

### The Un-dodgeable Reference Call Question (Interview Q Compilation)
A specific question to ask during reference checks to bypass generic praise and uncover a candidate's actual areas for growth.

How it works: Ask the referee: 'What feedback will I be giving this person in their first performance review?'

### The Unsell Email (Kevin Yien)
An email sent to a candidate at the offer stage detailing the hardest, most unglamorous parts of the job to test their conviction.

How it works: Sent at the offer stage (not before). Maximum of 8 bullet points. Directly addresses fears hinted at during the interview process (e.g., expected working hours, startup chaos, weekend expectations).

### Work Trial Compensation Benchmarks (Adding a work trial to your interview process)
A reference table of how six companies compensate work trial candidates

How it works: Company | Rate | Notes
Gumroad | $150-$200/hr (same as full-time rate) | Contract via Flexile, candidates can choose equity split
Linear | $600/day flat | Regardless of seniority, role, or location
37signals | $1,500 for the week | Flat rate for 7-day trial period
PostHog | Candidate's existing day rate, or formula: (Annual basic salary + 30%) / 220 days | Offer charity donation if candidate can't accept payment
Automattic | $25/hr | Irrespective of location or role

### Work Trial Duration Benchmarks (Adding a work trial to your interview process)
Reference table showing how long different companies run their work trials

How it works: Company | Duration | Notes
PostHog | 1-3 days | Combined with interviews into 'SuperDays' or 'SuperWeeks'; 80% work, 20% meeting people
Linear | 3-5 days | 3-4 days typical, leadership hires take full 5 days; accommodates weekends/schedules
37signals | 7 days | Candidates spend 6-12 hours total; time is flexible
Auth0 | 7 days | Candidates typically spend a couple hours at night
Automattic | 40 hours | Measured in hours not days; could take 2 weeks to 3 months; flexibility is key
Gumroad | 4-6 weeks | 10-20 hours expected per week; candidates don't need to quit current job

### Written Sales Candidate Screening Doc (Pete Kazanjy)
A Google Doc with ~12 biographical questions sent to sales candidates before any interview, used to filter for seriousness, communication ability, and attention to detail.

How it works: Format: Google Doc with edit rights given to candidate. ~12 biographical questions like 'Tell me about something you've built that you're proud of.' Evaluation criteria: (1) Did they complete it at all? (57% won't). (2) Can they communicate compellingly with beginning/middle/end? (3) Attention to detail — typos, skipped questions. (4) Speed of completion. Used as first screen before any live interview.

## Checklists

### "Sell Me This App" Interview Test (Jason M Lemkin)
A practical interview assignment to test if a sales candidate can actually sell your specific product.

How it works: Have the candidate watch an explainer video or webinar of your product before the interview. During the interview, ask them to do a live demo and pitch the product back to you. Evaluate if they understand the core problem it solves, not just the technical features.

### 3-Point Adaptability Interview Checklist (Jason Droege)
A simplified interview criteria list for hiring adaptable talent in fast-moving industries.

How it works: 1. Are you a curious problem solver and can you articulate that verbally? 2. Can you work across people (are you humble enough)? 3. Are you a good leader?

### 5-Category Interview Panel Design Checklist (How to learn the most about a candidate from a single interview question)
A checklist for ensuring your interview panel covers all 5 critical evaluation dimensions when assessing a candidate.

How it works: Ensure your interview panel covers these 5 dimensions:

☐ 1. How do they handle the hard stuff? — Resilience, failure response, ambiguity navigation, conflict resolution, disagreeing with leadership
☐ 2. How do they think? — First-principles thinking, contrarian views, introspection, genuine curiosity, depth of analysis
☐ 3. How do they build, ship, and drive impact? — Accomplishments, frameworks (not just outcomes), initiative, storytelling, definition of impact
☐ 4. Who are they as people? — Self-awareness, motivations, values, growth trajectory, natural reward mechanisms, cultural fit
☐ 5. Curveball/authenticity check — Breaking the interview mindset, forcing genuine responses, testing problem-framing ability

Recommendation: Pick a few questions from each category that resonate with your process and goals. Don't use all 25.

### 5-Skill Stack Rank Interview Question (Bangaly Kaba)
An interview technique to assess self-awareness and skill fit for senior product roles.

How it works: Give the candidate 5 critical skills required for the role. Ask them to rank them 1 (strongest) to 5 (weakest). Probe into why they ranked #2, #4, and #5 where they did to understand their context and self-awareness.

### Board Deck Interview Hack (Brian Halligan)
A method to test if an executive candidate is a 'yes person' or a critical thinker.

How it works: 1. Have the candidate sign an NDA. 2. Send them the latest board deck or memo. 3. Schedule a 30-minute chat to discuss it. 4. Treat it as a red flag if they are purely complimentary; look for them to challenge you.

### Business Model Interview Question Criteria (Claire Vo)
What to look for when asking a PM candidate how they would improve the company's business model.

How it works: Evaluate if the candidate can identify: 1) How the company identifies people in the market, 2) The pricing model, 3) Underlying unit economics/COGS, and 4) Points of leverage along the funnel to improve top-line revenue or margin.

### CPO Interview Questions for PMs (Inbal S)
Two behavioral questions used to assess a candidate's character, vulnerability, and ability to influence.

How it works: 1. 'What is the most innovative thing you have done and why do you think it's innovative?' (Tests for vulnerability vs. ego). 2. 'Give me an example of a time you had a disagreement with your manager, what did you do, and how did it go?' (Tests for communication, influence, and willingness to push up).

### Community Engagement Manager Interview Questions (A founder’s guide to community)
Eight interview questions for hiring a community engagement manager

How it works: 1. Tell me about your background and why you're interested in leading this community.
2. We want to make sure that the person in this role has experience putting together an engagement plan for online community programs. Can you tell me about a time you worked on a problem like this?
3. What separates good from exceptional when leading communities?
4. What skills do you think are required to drive quality community engagement?
5. Say we've been seeing a drop in engagement consistently over three months. What would you do to assess the situation and turn things around?
6. What values are really important to you when it comes to the teams/companies that you work with?
7. How would your current or past colleagues describe you as a leader?
8. How would they describe an area that you could improve on?

### Executive Interview Question: Firing (Carilu Dietrich)
A behavioral interview question designed to test a leader's true management experience, tenure, and empathy.

How it works: Question: 'How many people have you fired? And tell me about each of the experiences.' Look for compassion, business drive, and the context (layoffs vs. performance management) to gauge their leadership under pressure. If they haven't fired anyone, they haven't managed at scale for long.

### Favorite Interview Questions from 100+ Guests (The Best of Lenny’s Newsletter—2024 Edition)
Crowdsourced collection of the best interview questions from over 100 podcast guests

How it works: A compilation of favorite interview questions collected from over 100 guests on Lenny's Podcast, spanning product management, engineering, design, and leadership roles.

### Further Study Resources for PM Interviewing (How to learn the most about a candidate from a single interview question)
A curated list of 6 related resources for deeper learning on PM interviewing from both the interviewer and candidate perspective.

How it works: 1. How to pass any first-round interview (even in a terrible talent market)
2. Adding a work trial to your interview process
3. Preparing for a PM interview
4. My favorite PM interview questions
5. How to interview product managers
6. Podcast episode: My favorite interview questions from 100+ guests

All available on lennysnewsletter.com

### Generalist Interview Questions (7 Questions for Any Function) (My favorite PM interview questions)
Seven versatile interview questions that Lenny uses across all roles and levels to assess self-awareness, character, initiative, and cultural fit.

How it works: 1. When I go ask people you've worked with about you, what will I hear?
2. What's something you're better at than most other people—what's your superpower?
3. What's something you're working to improve?
4. Among the people you've worked with, who do you admire most and why?
5. What kinds of people do you like to work with? What kinds of people have you found it difficult to work with?
6. Tell me about a time you took the initiative. What happened?
7. What's one part of your previous company's culture that you hope to bring to your next one? What one part do you hope to not find?

### Hard Reference Check Questions (Lauren Ipsen)
A list of pointed questions to ask during a reference check to get past standard positive fluff and uncover real insights.

How it works: 1. Why would I not hire this person? 2. What are their actual biggest weaknesses? (Push past 'they work too hard'). 3. Would you hire this person again? 4. Would you report to this person? 5. Would you endorse this person if you knew your name was attached to it?

### Interview Question Structure (Tom Conrad)
Two principles for structuring job interviews: use behavioral questions rooted in past experience and probe for intrinsic motivation

How it works: Principle 1: Avoid questions that ask candidates to solve your current problems (creates unfair imbalance). Instead, start every question with 'Tell me about a time in your career when...' to ground answers in actual experience. Principle 2: Near the end of the interview, ask 'Imagine you had a really great day at work. What was it that you did on that day?' This reveals natural reward mechanisms and helps identify highest-best-use alignment for the role.

### Interview Question: Tell Me About a Product You Love (Ravi Mehta)
A single screening interview question with a series of follow-up probes that can last 5 to 60 minutes and reveals product sense, values, and thinking

How it works: Opening: 'Tell me about a product that you love' (word 'love' is deliberate). Follow-ups: 1) Why do you love it? 2) Why do you think other people love it? 3) What would you like to see about it in the future? 4) Pick a feature you'd like to build for that product. 5) Why do you think that's a good feature? 6) How would you measure the success of that feature? Reveals: product sense, customer empathy, analytical thinking, personal values. Note: physical product answers reveal hobbies/interests.

### Interview Questions for Introspection and Character (Scott Belsky)
Two interview questions Scott uses to assess introspection and self-awareness in candidates

How it works: Question 1: 'Tell me something you've learned about yourself that reveals a limitation in how you work.' Tests: introspection, openness about weaknesses, whether they blame others or self-reflect when they hit limits. Question 2: 'Do you consider yourself lucky?' Tests: security/insecurity, comfort with acknowledging privilege and luck, humility.

### MarTech Interview Questions (Austin Hay)
Specific behavioral and situational questions to test a candidate's systems thinking and preparation.

How it works: 1. 'How did you prepare for this interview?' (Tests planning and systems thinking). 2. 'You start tomorrow. By Friday you have to write a report on all the things we should change in our system. What do you do?' (Tests for tool bias vs. problem-first thinking). 3. 'Tell me about the most difficult or challenging thing you've overcome in the last year.' (Tests vulnerability).

### Notion's EM Interview: Product Spec Review Exercise (How Notion builds product)
An interview exercise for engineering managers where they comment on a product spec, used to assess craft, attention to detail, and breadth of thinking

How it works: Exercise: Give the EM candidate a product spec and ask them to comment on it as if their team was working on it.

Evaluation dimensions (what interviewers look for):
1. Comments on the problem statement — Is the problem well-defined? Is it the right problem?
2. Whether the work is worth doing relative to other things — Prioritization thinking
3. ROI to the business — Business acumen and strategic thinking
4. Which pixels or UX elements look off — Craft and attention to visual/interaction detail
5. How the thing interacts with other parts of the product — Systems thinking

Overall hiring criteria across roles:
- Craft and attention to detail
- Expansive view of their role
- End-to-end ownership mentality

### One-Minute Teaching Interview Question (Ryan J. Salva)
An icebreaker interview question for early to mid-career PMs that tests communication ability

How it works: Prompt: 'Teach me something new in one minute.' Give candidate a moment to think, then start a timer. Evaluate on three criteria: 1) Completeness - Did they finish the lesson within one minute? 2) Complexity - How sophisticated was the topic they chose? (e.g., patting head vs. 18th century art history) 3) Clarity - Did you actually learn and understand something by the end? Best answer example: A Vanderbilt university candidate taught about 18th century art and its connection to religious trends—scored extremely high on all three criteria and was a strong hire.

### PM Interview Process with Prep Call (Melissa Tan)
A multi-stage interview process designed to test first principles thinking and coachability.

How it works: 1. Hiring manager screen with live problem solving (e.g., pulling up a pricing page and asking what to test). 2. Competency interviews with cross-functional team members. 3. Prep call with hiring manager to review presentation draft and give feedback. 4. 30-minute presentation (max 30 slides) with 15-min Q&A to see if feedback was incorporated.

### PM Interview Project Evaluation Criteria (Universal) (How to interview product managers)
Common themes across all project examples for what to look for when evaluating PM interview projects

How it works: When evaluating a PM interview project, look for:
1. How they break down the problem — what levers/dimensions do they identify?
2. How they structure their solution — is it logical and well-organized?
3. How they communicate — clear, succinct, compelling presentation and writing?
4. Do they think big (ideal state) or just incrementally (edge optimization)?
5. Do they tie solutions to success metrics?
6. Do they consider user experience deeply?
7. Do they create/reference user personas?
8. Are they curious — do they ask good questions?
9. Can they make gut calls with incomplete data?
10. Are solutions feasible, testable, and appropriately scoped?
11. Can they improve on their ideas in real-time during discussion?
12. Do they consider multiple constraints (design, technical, GTM)?
13. Do they think about before/during/after of a solution, not just the 'during'?

IMPORTANT: You are NOT looking at how close they got to the right answer. You are looking at process, structure, and communication.

### Paid Work Trial Process (Karri Saarinen)
A final interview step where candidates work as mini-contractors on a real problem.

How it works: 1. Give candidate a vague problem statement. 2. Candidate scopes it down to fit the timeframe. 3. Candidate gets codebase access and builds a version. 4. Candidate presents the work. 5. Both sides evaluate the working relationship.

### Performance Marketer Interview Criteria (Jonathan Becker)
Key traits and questions to evaluate when hiring a performance marketer.

How it works: 1. Technical background (math, physics, engineering). 2. Experience managing specific channels (Meta, Google). 3. Understanding of creative and attribution. 4. Composure test: Ask a difficult logic question (e.g., 'How many windows are in NYC?') to see how they react under pressure.

### Perplexity's PM Hiring Criteria (How Perplexity builds product)
Criteria for hiring PMs in an AI-native company, emphasizing what to look for and what to avoid

How it works: LOOK FOR: 1) Flexibility and initiative above all. 2) Ability to build constructively in a limited-resource environment. 3) Willingness to wear several hats. 4) Strong IC track record with clear quantitative impacts on USERS (not internal company impact). 5) Fundamental technical knowledge: math, statistics, basic grasp of programming. 6) Culture fit and being easy to work with. RED FLAGS / AVOID: 1) Resumes that prioritize 'helping other people and finding alignment' as core skills. 2) Terms like 'Agile expert' or 'scrum master.' 3) People whose primary strength is guiding other people's work. 4) People who rely on managing processes rather than building. PREDICTION: Technical PMs or engineers with product taste will become the most valuable people at a company over time.

### PostHog Work Trial Task Design Principles (Adding a work trial to your interview process)
Six principles for designing effective work trial tasks based on PostHog's experience

How it works: 1. Make the task open-ended (e.g., build a new product from scratch vs. coding challenges with specific answers)
2. Design tasks to be too much work for one person to complete in a day—tests prioritization ability
3. Use representative work, not actual work you'd ship (avoids IP issues, contractor requirements, and codebase complexity)
4. Assess both product skill AND engineering/functional skill simultaneously
5. Focus on themes throughout: scrappiness, low ego, ambition, optimism—have the scrappiest person assess scrappiness
6. If candidate isn't given a perfect score, force evaluator to explain why—surfaces patterns across multiple evaluators

### Product Sense Interview Evaluation Dimensions (The definitive guide to mastering product sense interviews)
The five dimensions interviewers use to score product sense candidates — candidates need at least a passing score on each

How it works: 1. Clear communication: Delivering an easy-to-follow response with solid structure. 2. Product motivation: Examining the product's purpose and mission. 3. Segmentation: Defining the audience and prioritizing a target segment. 4. Problem identification: Listing and prioritizing key pain points faced by the chosen segment. 5. Solution development: Brainstorming and prioritizing a solution for the problem, including a v1. Key note: Excellence in one area can't compensate for weakness in another. A solid score on each dimension is sufficient to pass — perfect scores aren't required.

### Reference Check Technique for PSHE Assessment (Shishir Mehrotra)
A set of techniques for conducting reference checks that reveal where a candidate falls on the PSHE spectrum without revealing what you value.

How it works: Techniques: 1) Blind reference (ideal): Don't name the person. Ask 'When you think of your teams, who is best at [identifying problems / solving hard problems / organizing teams / executing playbooks]?' 2) Contrast-based: Present four PSHE personas without ranking. Ask which one best describes the candidate. 3) Always ask: 'Would you hire this person again? How excitedly?' 4) Always ask: 'What questions should I have asked that I didn't?' 5) Don't reveal what you value — let them assign the persona. Key insight: Amazing H-level PMs get glowing references ('runs such efficient meetings!') but when you ask 'Who picks the right problems?' the answer is often someone else. Hiring signal priority: 1) Reference checks, 2) Work product/presentations, 3) Interviews.

### Rippling PM Interview Process (Jeremy Henrickson)
The step-by-step interview loop used to hire Product Managers at Rippling.

How it works: 1. Initial conversation with hiring manager. 2. Product discussion with Jeremy (starts with 'What questions do you have for me?'). 3. A case study designed to be too complex to solve upfront, allowing interviewers to change assumptions on the fly to test mental agility.

### The 'Worst Product' Interview Question (Failure)
A specific interview question used to evaluate PM candidates.

How it works: Question: 'What's the worst product you've ever shipped?' Criteria for passing: The candidate must have actually shipped something bad (showing they have enough reps) and must be able to admit it openly.

### What Interviewers Look For in PS Candidates (The definitive guide to mastering product sense interviews)
Six capabilities that interviewers evaluate throughout the entire product sense interview approach

How it works: Interviewers evaluate not just your final answer but your entire approach. They look for candidates who can: (1) Think systematically about product ecosystems, (2) Break down ambiguous problems with clear structure, (3) Identify specific user needs based on behavior and context, (4) Develop creative solutions that leverage company strengths, (5) Communicate complex ideas with clarity, (6) Respond thoughtfully to feedback and new information.

### Work Challenge Interview Format (Sanchan Saxena)
Airbnb's interview approach for evaluating content-oriented leaders using real business problems instead of generic presentations.

How it works: Steps: 1) Give candidates a real business problem (e.g., 'We need to build millions of Airbnb Plus homes but don't know how'), 2) Ask them to present how they'd solve it, 3) Evaluate depth of thinking and content — not just process frameworks, 4) Look for specific approaches (e.g., 'I'd find third-party companies to scale operations') vs generic process slides ('Ideation → Execution → Iteration'), 5) For past experience: ask candidates to describe the specific role THEY played, not what their team accomplished, 6) Ask 'Tell me the story of your career and focus on WHY you did what you did' — the why reveals more than the what.

### Work Trial Implementation Checklist (Adding a work trial to your interview process)
Comprehensive tips and lessons from six founders for setting up a successful work trial process

How it works: Pre-Trial Setup:
1. Define why you want to do work trials and ensure it fits your culture (Automattic)
2. Set clear expectations with your hiring teams about time commitment (Automattic)
3. Accept that time-to-hire will be longer (Automattic avg: 70+ days from first contact to offer)
4. Create exercises for each position with clear expectations per role (Auth0)
5. Only use work trial stage for candidates you'd otherwise hire—don't use it to decide if you're unsure (Auth0)
6. Write job ads describing 'what you would have done here last week' to attract the right finalists (37signals)
7. Be super-transparent about the whole process from the start—public handbook, job adverts (PostHog)
8. Mark roadmap tasks as 'good for trialers' throughout the year (Gumroad)

During Trial:
9. Create a dedicated Slack group a few days before and invite everyone relevant (PostHog)
10. Have dedicated Trial Leads or Buddies as point of contact (Automattic)
11. Provide continuous feedback so candidates can adapt (Automattic)
12. Keep interactions written down; avoid Zoom (or record it) for async review (Auth0)
13. Be available when candidates are working, including nights/weekends (Auth0)
14. Make the task open-ended so candidates can stretch themselves (PostHog)
15. Design tasks to be too much work for one person—tests prioritization ability (PostHog)
16. Set clear expectations on work intensity—don't send mixed signals (PostHog)
17. Balance 80% work, 20% meeting people in a single trial day (PostHog)

Post-Trial:
18. If doing multi-day trial, set expectation you may cut short to not waste time (PostHog)
19. Collect blind feedback from evaluators before group debrief (Linear)
20. Force team to give reasons for any non-perfect scores (PostHog)
21. Offer charity donation as alternative if candidate can't accept payment (PostHog)
22. Close feedback loop with candidates regardless of outcome (Linear)
23. Aim to make decisions within 48 hours (PostHog)

## Examples

### 37signals Design Work Trial Project Prompt (Adding a work trial to your interview process)
An actual project prompt 37signals gives to design candidates, asking them to build (not just design) improvements to Basecamp

How it works: Key characteristics of the 37signals approach:
- Candidates get 7 days, typically spend 6-12 hours
- Prompt is strategically vague (e.g., 'Here's a screen in Basecamp, what would you do to make it better?')
- Candidates must build in HTML/CSS, not just Figma mockups ('We're not making pictures here')
- No access to codebase—must recreate and build from scratch
- Candidates cannot ask the team questions during the trial
- What they choose to focus on is entirely up to them—this reveals priorities and judgment
- Full project prompt available at linked Google Doc

Evaluation call structure:
- Jason Fried + one other designer on the call
- Candidate shows and explains what they did and why
- Team pokes holes even if they like the work
- Tests: ability to think on feet, adapt, riff, take critique
- Final question: 'If you had an extra three days, what would you do differently?'
- After interviewing 5 people, 1-2 clearly stand out
- Judgment based entirely on this project, not portfolio or history

### AI-Assisted Interview Assessment (Brendan Foody)
A modern technical interview format that embraces AI tools.

How it works: Prompt candidates with: 'Use ChatGPT, Claude, Cursor, and whatever tools are available to build a website and let's see what product you're able to build in an hour.' Evaluates AI leverage rather than rote memorization.

### AI-Generated Interview Rubric (Jenny Wen)
A workflow for turning unstructured personal notes into a structured hiring rubric.

How it works: Step 1: Collect years of unstructured local notes (1-on-1s, random thoughts, interview notes, tiny memos) into a single folder. Step 2: Use an agent like Claude Cowork to ingest the folder. Step 3: Prompt: 'Read through all of my interview notes and memos related to design craft in this folder, and help me craft a memo/rubric for how I assess craft in interviews.' Step 4: Use the output to formalize your implicit hiring standards.

### Airbnb PM Interview Project — Host Conversion (How to interview product managers)
A day-of interview project about increasing host acceptance rates, used at Airbnb to hire IC PMs and managers

How it works: Format: Day-of interview, 90 minutes to work, then present to a small group of potential colleagues (engineer, designer, researcher). Shared from memory.

Prompt: 'When Airbnb guests attempt to book a place, 50% of the time they are ignored or rejected by hosts. This leads to a bad user experience and a lack of trust in the platform, and the business misses out on revenue. How would you increase this conversion rate from 50% to 90%?'

Context provided:
- Nearly all host rejections are for logistical reasons (calendar not updated, can't support pets, don't allow parties, etc.)
- Hosts sometimes don't know they received a guest request
- Hosts have 24 hours to respond before the request expires

Evaluation criteria:
- How did they break down the opportunity to increase conversion? What levers did they identify?
- Which lever/opportunity did they see as biggest, and why?
- Did they think big (working backward from the ideal) or incrementally (optimizing at edges)?
- How they prioritized — what did they optimize for?
- How they laid out their proposal and communicated it — did it make sense?
- How they balanced needs of both sides of the marketplace

### Auth0 Take-Home Exercise Approach (Adding a work trial to your interview process)
Auth0's historical work trial process using real past problems as take-home exercises

How it works: Original Process (pre-Okta):
1. Email screener
2. Two interviews (tech lead + engineering manager, or director + engineering manager)
   - Past work experience deep-dive
   - Communication and teamwork assessment
   - High-level design/tech problems (no algorithms/coding)
3. Take-home exercise (7 days)
4. Demo presentation

Exercise Design:
- Based on real-world situations the company faced and solved in the past
- This allowed evaluators to know ins and outs of the problem
- Same exercise reused across all levels, with adjusted expectations
- For rare positions (e.g. Director of Infrastructure), exercise created when candidates reached that stage
- Full example project prompt available at linked Google Doc

Post-Okta Change:
- Moved to 90-minute take-home code test via CodeSignal
- Reasons: larger candidate pipeline (original was too long, candidates self-selected out), reduced hiring team time
- Trade-off: less signal, acknowledged and accepted by org

### Chime PM Interview Project — Net(Income)Flix (How to interview product managers)
A real take-home PM interview project used at Chime to hire a manager for the identity product, about a hypothetical streaming service

How it works: Format: Take-home, timeboxed to 3-4 hours, presentation format, 45 minutes to present.

Prompt: 'Imagine you're the product lead for identity at a video streaming service called Net(Income)Flix. The CEO wants to maximize financial returns and has anecdotally heard that many customers share accounts with friends/family, leading to potential lost revenue. You have been tasked to come up with a plan to identify access to these rogue accounts and shut them down.'

Must address:
- How do you measure the scale of the problem/opportunity?
- What other product teams may be impacted? How to address their concerns?
- What features/solutions may address this issue (bullet point descriptions)?
- How do you prioritize and sequence your plan?
- How do you think about user experience?

Evaluation criteria:
- Answered the posed questions (some candidates didn't)
- Spent at least 1/4 of time on user experience
- Understood identity domain (2FA, device signals, location, etc.)
- Success metrics tied to the problem/opportunity
- Created user personas tied to features/UX, features tied back to success metrics
- [Bonus] Talked about quant and qual user feedback
- [Bonus] Pushed back saying some fraud is okay to optimize for UX
- [Bonus] Identified market opportunity for 'stolen' accounts (profiles, pricing, referrals)

### Contrarian Interview Question (Nikhyl Singhal)
An interview question designed to break candidates out of rehearsed answers and test authenticity.

How it works: Question: 'What's something that everyone takes for granted that you think is essentially hogwash or inaccurate?' (Can be tailored to management, AI, specific domains, etc.)

### Culture Fit Interview Scenario (Patrick Campbell)
A mini case study used in final interviews to test a candidate's judgment and alignment with the 'charitable interpretation' value.

How it works: Scenario: Someone shares a benign report in Slack, and another employee responds with something indirectly offensive (e.g., calling it 'stupid'). Question: 'What would you do, and what should the company do?' Used to filter out candidates with rigid zero-tolerance policies for gray-area mistakes.

### Designer Interview Project (Jason Fried)
A practical interview technique for assessing product designers.

How it works: Pay the final 5 candidates to complete a 1-week project. Critique the work with them. Ask: 'If you had another couple days, what would you do with this?' to test their gut instincts and ability to riff on the spot.

### Gumroad Full-Immersion Work Trial Model (Adding a work trial to your interview process)
Gumroad's approach of hiring candidates as contractors for 4-6 weeks with full internal access

How it works: Process:
1. One 30-minute 'culture fit' interview with CEO
2. 4-6 week work trial, 10-20 hours per week expected
3. Paid at $150-$200/hr (same rate as full-time), candidates can choose equity percentage
4. Contract signed via Flexile

How it works:
- Team marks roadmap tasks as 'good for trialers' throughout the year
- Candidates assigned these tasks (small bug fixes to large features like wishlists)
- Full access to internal tools: GitHub, Figma, Notion, Slack
- Candidates see all company internals: culture, finances, CEO attitude
- Framing: 'You're hired by default but will likely be fired in 30-60 days if you don't perform'
- Candidates don't need to quit their job
- Location-agnostic, no meetings, set own hours

Evaluation:
- Everyone participates, CEO makes final decision
- 'Hell yes' or 'no' framework
- ~20-30% of trialers pass
- 'If there's any doubt, there's no doubt'

### Interview Question: Explain Complex Concepts Simply (Summary: AI and product management | Marily Nika (Meta, Google))
Marily's favorite interview question for evaluating PM candidates

How it works: Ask candidates: 'How would you explain a database to a 3-year-old?' This tests communication skills and the ability to simplify complex technical concepts — a critical skill for AI PMs who must bridge technical and non-technical stakeholders.

### Laura Schaffer's Non-Cherry-Picked Product Question Technique (How to learn the most about a candidate from a single interview question)
A specific interview technique where the interviewer chooses which product/release to discuss rather than letting the candidate pick their best story.

How it works: Technique: Ask the candidate about a product they shipped or a release they led — but YOU choose which one to discuss, not the candidate.

Purpose: When candidates cherry-pick their examples, you only learn about outcomes. When you choose the product/release, you learn about their frameworks — how they build products, how they know if they're going to succeed, and how they approach building in general.

This reveals process and thinking, not just results.

### Linear Work Trial Project Examples by Role (Adding a work trial to your interview process)
Real examples of work trial projects Linear has given to candidates across different roles

How it works: Engineer: Building a feature allowing teams to effectively triage incoming feature requests (linked Notion doc available)
Content Marketer: Writing a blog post based on a feature release (linked Google Doc available); candidate's work was later shipped to production as part 2
Designer: Designing a way to resolve comments (visual mockup included)

Key principle: Work trial projects sometimes end up being the first project for the new hire when they get started.

### Procore/AppFolio PM Interview Project — Collaboration Tool Feature (How to interview product managers)
A take-home PM interview project about designing a new feature for a modern collaboration tool

How it works: Format: Take-home, on their own time, guidelines to keep to a few hours. 30-minute presentation + 30-minute discussion. Took 6-9 months to iterate and dial in the exercise.

Prompt: 'Pick a modern collaboration tool (e.g. Miro, Asana, Mural, Slack, etc.) and design a new feature or improvements to the acquisition, activation, or engagement steps.'

Constraints:
- 3 months of dev time with a team of 4 engineers who know the codebase
- Present: the problem, customer value, solution, success criteria, roadmap, trade-offs, release strategy, and mid-fidelity mock-up
- A one-pager supporting the presentation
- No bonus points for super-slick presentation; focus on content over form
- 30 minutes max to cover content, 30 minutes discussion

Assesses: product sense, execution, visual articulation (mocks), verbal articulation (presentation), and prose (one-pager). Also worked for designers with different constraints.

### Second-Order Thinking Interview Scenario (Kunal Shah)
An extreme hypothetical question used in interviews to test a candidate's ability to predict butterfly effects.

How it works: Example prompt: 'If everybody who has taken a COVID vaccine dies tonight, what happens in 12 months from now? Explain the impact on money, law, countries, military, and the stock market.' The interviewer evaluates the candidate based on the range of leaps they can make (A -> B -> C).

### Slack Growth PM Interview Project (How to interview product managers)
A real take-home PM interview project used at Slack to hire all levels of PM, focused on new team activation

How it works: Format: Take-home, complete within 72 hours, presentation format.

Background: 'The first part of your interview will be an assignment for members of the product, engineering, and design teams. Our goal is to see how you approach product problems in depth, with real-life situations.'

Problem Statement: 'Every day, people create new Slack teams. The most successful team creators get several people to create accounts and have a meaningful conversation within the first day or so. Inviting people is straightforward—set that aside. What is much more difficult is getting 3+ people to have a meaningful conversation in a new messaging service.

Go through the process of creating a new Slack team. Assume reasonable level of intent. Identify issues or missed opportunities with the current new-user experience that hold people back from meaningful conversations. Generate ideas for experiments. Prepare a prioritized plan. Flesh out at least 3 ideas into experiments the Growth team should run.'

What we want to see:
1. What questions do you have?
2. What assumptions are you making?
3. What data would help make your case?
4. How would you measure success?
5. How would you execute quickly?

Evaluation criteria:
- Structure and communicate ideas clearly and succinctly
- Curiosity — quality of questions asked
- Comfortable making gut calls with little/conflicting data
- Prioritizes quality customer experience when in doubt
- Creativity within product constraints — feasible, testable, not over-reaching
- Avoid hand-wavy solutions (e.g. over-relying on Slackbot as deus ex machina)

### Snap's Rapid Hiring Process (Tom Conrad)
Evan Spiegel made Tom Conrad a written VP of Product offer within 4 hours of their first meeting, illustrating both decisive leadership and potential red flags in hiring

How it works: Process: 45 min with Evan → 45 min with head of engineering → 45 min with head of legal → 1 hour group session with product designers → lunch break → called back → written offer in manila envelope with full terms and stock compensation. Tom's reaction: flattered but recognized potential red flags. Extended courtship by another week to meet more leadership. Key insight: brilliant founders can be decisive, but rapid offers merit additional due diligence.

### Square PM Interview Project — Square Training (How to interview product managers)
A real take-home PM interview project used at Square to assess mid-senior PMs about a fictional but realistic training product

How it works: Format: Take-home, 2-3 days to complete, expected 2-3 hours (everyone always spent more), 30-minute presentation + 15-minute discussion.

Prompt: 'You are the product manager for Square Training, a new product that we will build to help merchants train their staff on Square products (starting with the point of sale). Please prepare a short presentation to describe what you would build, in what order, and why. Designs are not required but may help in articulating the solution.'

Evaluation criteria:
- Problem context grounded in actual customer conversations (they went out and talked to real customers)
- Solution tangible and defined enough for actual conversation
- Able to reframe questions around a framework rather than getting bogged down
- Thought through before/during/after of a solution
- Considered design, technical, and GTM constraints (not just one)
- Able to improve upon the idea in the meeting rather than cling to original

Note: Experimented with both slide and doc formats; live discussion was both oral presentation and silent doc read.

### Teach me something I don't know (Interview Question) (Emily Kramer)
An interview question to test a candidate's ability to communicate complex topics simply.

How it works: Ask the candidate to describe something complicated they know well as simply as possible. Follow up by asking them to 'make it simpler' to test adaptability and clarity.

### Teleportation Device Interview Question (EOY Review, Shishir Mehrotra)
A hypothetical interview question used to test a candidate's ability to find 'eigenquestions'.

How it works: Setup: 'Scientists invented a teleportation device. You're hired to bring it to market. What do you do?' Let candidate generate questions freely. Then constrain: 'The scientists will only answer 2 questions, then expect a plan. What 2 questions do you ask?' Great answer example: Q1: 'Is it safe enough for humans?' Q2: 'Is it more expensive CapEx or OpEx (to buy or to run)?' These create four quadrants that drive completely different strategies (human fax machines, airport replacements, high-value goods transport, etc.). Note: Shishir no longer uses this exact question since publishing it; has a new unpublished version.

### The 'Deaf Friend Alarm Clock' Interview Question (Christian Idiodi)
A scenario-based interview question used to evaluate a candidate's collaborative problem-solving skills and empathy.

How it works: Prompt: 'I have a legally deaf friend who got a new job requiring them to wake up significantly earlier. Traditional alarm clocks won't work. Walk me through how you'd solve this.' Look for: Intellectual curiosity, asking questions, seeking collaboration (designers/engineers), and empathy, rather than jumping straight to a solo solution.

### The 'Impossible' Case Study (Matt MacInnis)
An interview tactic where every product candidate gets the same extremely difficult prompt.

How it works: Give everyone from entry-level to VP the same complex prompt. Evaluate how many 'corners' they see around, how they handle new invalidating information, and if they ask questions instead of getting defensive.

### The Teleportation Device Scenario (Interview Q Compilation)
A low-stakes, hypothetical interview question used to test a candidate's ability to identify the most critical variables in a new product launch.

How it works: Prompt: 'Scientists invented a teleportation device and hired you to bring it to market. What do you do?' After the candidate brainstorms questions, add a constraint: 'The scientists will only answer two questions, then they expect a plan. What two questions do you ask?' Look for questions that create distinct strategic quadrants (e.g., Is it safe for humans? Is it CapEx or OpEx?).

## Tools

### Collaborative Product Interview Prompts (Noam Lovinsky)
Interview questions designed to test craft through collaboration rather than behavioral recall.

How it works: Examples: 'Let's design an alarm clock for children.' or 'Given where technology is at, if we were to rebuild email, how might we do that?'

### Favorite Interview Question (Luc Levesque)
A prompt used to gauge a candidate's depth of knowledge and passion for their craft.

How it works: Question: 'Teach me something about growth that I don't already know.' Used to see what the candidate considers the top of their knowledge stack.

### Risk and Regret Interview Question (Jason Shah)
An interview question used to assess a candidate's growth mindset and self-reflection capabilities.

How it works: Ask the candidate: 'What is a risk you regret not taking, why, and what did you learn about yourself?' Look for the ability to be vocally self-critical without being unproductively hard on oneself.

### Self-Awareness Interview Question (Ian McAllister)
An unexpected interview question designed to test a candidate's self-reflection and awareness of their unique strengths.

How it works: Question: 'At this stage in your career, what have you learned about yourself? How are you different from other people?'

### Top 10 Accomplishments Interview Question (Barbra Gago)
An interview question used to gauge a candidate's values and balance of quantitative vs. qualitative achievements.

How it works: Ask the candidate: 'What are your top 10 accomplishments?' Look for whether they list personal vs. professional achievements, and how they balance quantitative metrics with qualitative milestones.

### Worst Product Shipped Interview Question (Maggie Crowley)
An interview question used to test a PM candidate's experience, humility, and ability to learn from failure.

How it works: Ask 'What's the worst product you've ever shipped?' Look for candidates who laugh, admit a real mistake, and explain what they learned from the failure.

# Interviewing and Evaluating Candidates - All Guest Insights

*48 sources, 77 insights*

---

## Albert Cheng

> "I saw some of the highest performers just being people that had very high agency, had that clock speed, had that energy, but they didn't necessarily need to have deep experience on that matter."

**Insight:** In rapidly evolving environments like AI growth, high individual agency and 'clock speed' are more predictive of success than deep domain experience.

**Tactical advice:**
- Prioritize hiring candidates with high agency who can solve problems without relying on established playbooks.
- Screen for 'clock speed' and energy to ensure team members can keep pace with shifting market conditions.
- Look for talent that is willing to intentionally discard outdated habits in favor of learning new, AI-accelerated workflows.

*Source: [How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)](https://www.youtube.com/watch?v=2BKmNmnEj9w) @ 01:08:03*

---

## Annie Duke

**Insight:** Improve hiring success rates by replacing vague gut feelings with explicit, structured evaluation rubrics.

**Tactical advice:**
- Define clear, measurable criteria for a role before beginning interviews.
- Move from implicit intuition to explicit scoring to identify where judgments go wrong.
- Use structured rubrics to ensure all candidates are evaluated against the same standard.

*Source: [This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player)](https://www.youtube.com/watch?v=svQMODvIGAE) @ 00:20:35*

---

## Anuj Rathi

**Insight:** 

*Source: [The full-stack PM | Anuj Rathi (Swiggy, Jupiter Money, Flipkart)](https://www.youtube.com/watch?v=1sClhfuCxP0) @ 00:49:19*

---

## Austin Hay

**Insight:** The ideal MarTech hire is essentially a specialized Product Manager who can architect technical platforms while managing the cross-functional processes between marketing and engineering.

**Tactical advice:**
- Target 'technical operators' who have experience standing up tools like CDPs or CRMs within growth or UA teams.
- Screen for candidates who view tools not as endpoints, but as systems meant to solve specific business problems.
- Evaluate the candidate's ability to manage the 'unsexy' but high-leverage work of contract negotiation and liability exposure.

*Source: [The ultimate guide to Martech | Austin Hay (Reforge, Ramp, Runway)](https://www.youtube.com/watch?v=B79p85DHLkU) @ 00:58:02*

---

## Bill Carr

**Insight:** Scaling high-quality hiring requires a scientific approach that utilizes specific mechanisms and systems to maintain standards as the CEO's direct involvement decreases.

**Tactical advice:**
- Implement a standardized hiring mechanism, like the Bar Raiser program, to ensure consistency across all departments.
- Treat the hiring process as a scientific experiment by testing hypotheses, measuring outcomes, and iteratively improving.
- Use a system of peer-led debriefs to ensure hiring decisions are based on data and leadership principles rather than urgency.

*Source: [Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards)](https://www.youtube.com/watch?v=S9WHQa_AJQo) @ 01:14:19*

---

## Brendan Foody

> "How can they leverage this technology to do so much more? We'll give people interviews where we say, 'Use whatever tools are available to build a website and let's see what product you're able to build in an hour.'"

**Insight:** Modern talent evaluation should focus on a candidate's ability to maximize output using AI tools rather than testing their ability to work unassisted.

**Tactical advice:**
- Allow candidates to use any available AI tools during the technical interview process.
- Set time-constrained tasks that require high output through tool leverage.
- Evaluate the quality of the final product and the candidate's speed of execution.

*Source: [Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor)](https://www.youtube.com/watch?v=ja6fWTDPQl4) @ 00:20:47*

---

## Brian Halligan

> "I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference."

**Insight:** Relying on formal interviews and resumes is often less effective than conducting rigorous blind references and testing a candidate's willingness to challenge the status quo.

**Tactical advice:**
- Conduct blind references and ask if the candidate was in the top 1% of employees or if the reference would enthusiastically rehire them.
- Have candidates review a real board deck under NDA to see if they provide meaningful challenges rather than just being a 'yes person.'
- Prioritize 'spiky' candidates with significant strengths over 'well-rounded' candidates who have fewer weaknesses but less impact.

*Source: [Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)](https://www.youtube.com/watch?v=3UyitfSbY6c) @ 00:06:11*

---

**Insight:** A founder's ability to scale is often driven by a state of 'constructive dissatisfaction' and a relentless focus on the future over past accomplishments.

**Tactical advice:**
- Look for leaders who maintain a state of positive dissatisfaction with their current progress and a singular focus on the end state.
- Evaluate if the founder is prepared for the 'full contact' reality of being always on seven days a week.
- Check if the founder is successfully transitioning their time toward executive recruiting and organizational design as the company grows.

*Source: [Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot)](https://www.youtube.com/watch?v=3UyitfSbY6c) @ 00:17:02*

---

## Carilu Dietrich

**Insight:** Verify an executive's leadership depth by investigating how many people they have actually managed during periods of rapid scaling.

*Source: [How to achieve hypergrowth in your business and career | Carilu Dietrich (Atlassian, Miro, Segment, 1Password)](https://www.youtube.com/watch?v=Pm7QSWDIEUc) @ 01:01:11*

---

## Crystal W

**Insight:** 

*Source: How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu @ 00:52:44*

---

## Dhanji R. Prasanna

**Insight:** 

*Source: [How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna](https://www.youtube.com/watch?v=JMeXWVw0r3E) @ 00:46:14*

---

## EOY Review

**Insight:** 

*Source: EOY Review @ 00:19:14*

---

## Elizabeth Stone

**Insight:** The quality of a company's outcomes is directly tied to the intentional maintenance of high talent density from its earliest days.

**Tactical advice:**
- Look for candidates who contribute to the overall talent density of the organization.
- Seek excellence in potential hires to ensure the company remains a place where top performers thrive.

*Source: [How Netflix builds a culture of excellence | Elizabeth Stone (CTO)](https://www.youtube.com/watch?v=2XgU6T4DalY) @ 00:39:33*

---

## Farhan Thawar

**Insight:** Practical, project-based evaluation provides a much clearer signal of a candidate's competence and drive than traditional resume screening.

**Tactical advice:**
- Ask candidates to build a functional tool or extension using your company's platform as part of the assessment.
- Look for evidence of self-directed learning and the ability to navigate complex documentation independently.
- Prioritize candidates who demonstrate tangible work in their repositories over those who only submit standard resumes.

*Source: [How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng)](https://www.youtube.com/watch?v=C_lhMOjG7PE) @ 01:03:28*

---

## Geoff Charles

> "It's also a great way to have positive selection in terms of talent because talent wants to join companies that ship fast. And a lot of people who join Ramp, I ask them, 'Why are you interested in joining the company?' And they often say, 'Well, it's because you guys are actually building things and shipping things and I want to know what that feels like.'"

**Insight:** Shipping products at an exceptional pace naturally attracts top talent who are motivated by impact and tangible results.

**Tactical advice:**
- Use the company's shipping velocity as a primary recruiting value proposition.
- Identify candidates who prioritize the ability to build and ship over corporate status.
- Ask candidates directly why they are drawn to high-velocity environments.

*Source: [Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product)](https://www.youtube.com/watch?v=aNJDZ_RzTVk) @ 01:02:06*

---

## Hari Srinivasan

**Insight:** 

*Source: [LinkedIn’s product evolution and the art of building complex systems | Hari Srinivasan (LinkedIn)](https://www.youtube.com/watch?v=ZUwkTs_QWqg) @ 00:58:06*

---

## Interview Q Compilation

**Insight:** Presenting a low-stakes hypothetical scenario helps reveal a candidate's natural ability to identify and prioritize the most important variables in a complex problem.

**Tactical advice:**
- Use a hypothetical, low-stakes scenario like a teleportation device to test strategic thinking.
- Limit the candidate to only two questions to force them to identify the most critical variables.
- Look for 'Eigenquestions' that clarify the fundamental constraints of the business model.

*Source: Interview Q Compilation @ 00:04:31*

---

> "Ambiguity is a big one for me, because at the end of the day, the PM job is really ambiguous. It's really hard to describe on a piece of paper all the things that you're going to encounter. Good answers are people who put structure and a way forward through the ambiguity."

**Insight:** Evaluating how a candidate structures their approach to ambiguity is the best way to determine if they can successfully navigate the inherently undefined nature of product management.

**Tactical advice:**
- Ask behavioral questions focused on how candidates have navigated ambiguous situations in the past.
- Look for candidates who proactively seek help and external inputs rather than claiming to have all the answers.
- Evaluate whether the candidate can create a structured path forward and define milestones for success.

*Source: Interview Q Compilation @ 00:11:29*

---

> ""Describe to me a time when you were part of a controversial product decision. What did you do?" All those things. I think it's really revealing, because if they can set up this conflict and understand why this problem was really important and represent both sides and such that you can understand why that conflict existed in the first place, and they can do it in this kind of even-keeled way where you realize that they can take on these different perspectives, you start to learn a lot about that person, I think."

**Insight:** Asking a candidate to describe a controversial decision and articulate both sides of the conflict reveals their ability to remain objective and think critically under pressure.

**Tactical advice:**
- Ask candidates to describe a time they were involved in a controversial product decision.
- Require the candidate to represent both sides of the conflict to see if they can understand the existential importance of the problem.
- Observe if they provide an "even-keeled" response that demonstrates their ability to take on different perspectives.

*Source: Interview Q Compilation @ 00:16:15*

---

**Insight:** Forcing candidates to move past 'luck' when explaining their success reveals their true level of self-awareness and how deeply they reflect on their own impact.

**Tactical advice:**
- Ask candidates what they attribute their success to, but explicitly prohibit them from saying "luck."
- Evaluate the candidate's level of self-awareness based on their ability to articulate the specific reasons for their progress.
- Look for curiosity and a clear mental model of how they interact with the world around them.

*Source: Interview Q Compilation @ 00:03:22*

---

## Jason Droege

**Insight:** 

*Source: [First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege](https://www.youtube.com/watch?v=W99jdYZOlN0) @ 01:09:31*

---

## Jason Fried

**Insight:** Small, constrained teams of two enable high-quality output by removing the friction of large meetings and collective indecision.

**Tactical advice:**
- Form small project units consisting of one designer and one programmer to maximize autonomy.
- Enforce firm deadlines on design iterations to force trade-offs and focus on the most important user needs.
- Minimize organizational layers and support staff to keep design work tight, simple, and clear.

*Source: [Jason Fried challenges your thinking on fundraising, goals, growth, and more](https://www.youtube.com/watch?v=dAnF0tk0di8) @ 00:50:34*

---

## Jeremy Henrickson

**Insight:** Evaluate PM candidates by testing their ability to simplify complex problems and demonstrate ownership over business outcomes.

**Tactical advice:**
- Assess mental agility by asking candidates to solve unfamiliar business problems in real-time.
- Look for 'systems thinking' to see if the candidate can anticipate how changes affect the broader platform.
- Check for a match between the candidate's preferred work stage (zero-to-one vs. scaling) and the team's current needs.

*Source: [Moving fast and navigating uncertainty | Jeremy Henrickson (Rippling, Coinbase)](https://www.youtube.com/watch?v=CsruQYKISYI) @ 00:52:48*

---

## Jess Lachs

> "I think this is something I saw when we would have some pockets of analytics folks embedded is having a consistent bar for talent in terms of what we're looking for, what are the technical skills, what are the soft skills? And being able to evaluate candidates with that same bar, using our same rubric."

**Insight:** Using a standardized evaluation rubric across a centralized organization prevents talent silos and ensures all data hires possess high-level technical and business-partnership skills.

**Tactical advice:**
- Implement a universal rubric to evaluate technical and soft skills consistently across all interview loops.
- Evaluate candidates on their ability to act as thought partners, not just technical service providers.
- Maintain a high bar for hiring centrally to ensure consistent data quality and methodology across the company.

*Source: [Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash)](https://www.youtube.com/watch?v=D4PDb_C8Dww) @ 00:24:31*

---

## Jessica Livingston

**Insight:** Effective interview panels benefit from a designated observer who focuses exclusively on interpersonal dynamics while others handle technical deep dives.

**Tactical advice:**
- Use a strict timer to keep the interview brief and maintain high intensity.
- Designate one team member to remain mostly silent to observe social cues and potential red flags.
- Test for flexibility by challenging the candidate's core assumptions to see if they respond with open conversation.

*Source: [The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host)](https://www.youtube.com/watch?v=h9MUuhsDJOM) @ 00:47:04*

---

## Judd Antin

**Insight:** 

*Source: [The UX research reckoning is here | Judd Antin (Airbnb, Meta)](https://www.youtube.com/watch?v=L6RKi9ZvkT4) @ 00:17:44*

---

## Karri Saarinen

**Insight:** Ensuring every hire—especially engineers—values product craft is essential for maintaining high quality without heavy management.

**Tactical advice:**
- Screen for a candidate's innate care for craft and quality regardless of their technical role.
- Look for engineers who take the initiative to improve product details beyond what is explicitly requested.
- Use work trials to evaluate how a candidate handles product decisions in real time.

*Source: [Inside Linear: Building with taste, craft, and focus | Karri Saarinen (co-founder, designer, CEO)](https://www.youtube.com/watch?v=4muxFVZ4XfM) @ 00:57:09*

---

## Katie Dill

**Insight:** Great designers must balance high-end craft and taste with the ability to execute on functional business needs.

**Tactical advice:**
- Look for candidates who demonstrate painstaking attention to detail and care for how things work.
- Evaluate if a designer can exceed user expectations rather than just delivering baseline functionality.
- Assess a candidate's ability to align their design decisions with growth and business metrics.

*Source: [Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)](https://www.youtube.com/watch?v=gfEEcssu304) @ 01:11:23*

---

## Keith Yandell

> "It's just like when you're interviewing someone, giving them tough feedback after the interview if there's an area of concern, but you otherwise like them, can be a really great way to see how they would interact with you personally as well as how they take feedback. And so that was my learning from the situation, is if you really enjoy an interview, except for maybe something on the culture side, to give the direct feedback and see how people engage."

**Insight:** Giving direct, even jarring, feedback to a candidate is the most effective way to test their humility and receptiveness to coaching.

**Tactical advice:**
- Provide blunt feedback on a specific cultural concern to see how the candidate responds.
- Look for curiosity and a desire to improve rather than defensiveness or ego.
- Use informal settings like dinner to probe personality traits that felt 'off' during formal interviews.

*Source: [Leading with empathy | Keith Yandell (DoorDash, Uber)](https://www.youtube.com/watch?v=tlCK9TuALtk) @ 00:03:55*

---

## Ken Norton

**Insight:** 

*Source: How to unlock your product leadership skills | Ken Norton, Ex-Google @ 01:05:40*

---

## Kevin Yien

> "When you get to offer stage, I send an email and I say all the terrible things that are probably going to reinforce their fears. If you can tell them that upfront and they can read that whole email and still be equally excited to join you, find yourself a A+ hire."

**Insight:** Exposing the most difficult parts of a job to a candidate before they sign ensures their commitment is based on a realistic understanding of the environment.

**Tactical advice:**
- Send an 'unsell email' at the offer stage detailing the company's biggest challenges and flaws.
- Directly address the specific fears a candidate might have about the role or culture.
- Prioritize candidates who maintain high excitement after learning the negative aspects of the position.

*Source: [Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)](https://www.youtube.com/watch?v=xOTO98MXG9o) @ 00:46:50*

---

## Kim Scott

**Insight:** Effective interviewing requires digging deep into a candidate's specific past actions to reveal their true level of accountability and expertise.

**Tactical advice:**
- Have candidates walk through their career history to look for patterns of accountability.
- Ask follow-up questions that force the candidate to explain the 'how' behind their accomplishments.
- Look for evidence of both technical skill and the ability to give and receive feedback.

*Source: [Radical Candor: From theory to practice with author Kim Scott](https://www.youtube.com/watch?v=V7tnbx-6Ayc) @ 01:19:22*

---

## Kunal Shah

**Insight:** Effective strategic thinkers demonstrate the ability to map out the 'second order' effects of decisions rather than just reacting to immediate needs.

*Source: [Kunal Shah on winning in India, second-order thinking, the philosophy of startups, and more](https://www.youtube.com/watch?v=EgBOVDzUUAA) @ 01:12:11*

---

## Lauren Ipsen

**Insight:** 

*Source: [Lessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, General Catalyst)](https://www.youtube.com/watch?v=v3pofqabzhs) @ 00:44:20*

---

**Insight:** 

*Source: [Lessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, General Catalyst)](https://www.youtube.com/watch?v=v3pofqabzhs) @ 00:49:53*

---

## Lenny Rachitsky

> "The more we thought about why some hires succeeded and some didn’t, the more we recognized that there is no substitute for working alongside someone in the trenches."

**Insight:** Implementing a work trial allows companies to move beyond superficial interview performance and gain high-fidelity signal on a candidate's actual productivity.

**Tactical advice:**
- Select a point on the realism spectrum based on your current company size.
- Invest more time in work trials when hiring for critical, early-stage roles.
- Aim to simulate a normal working environment as closely as possible.

*Source: [Adding a work trial to your interview process](https://www.lennysnewsletter.com/p/adding-a-work-trial-to-your-interview-process)*

---

> "Job candidates go through a paid work trial. Theyjoin the team for 1-5 days and work on a real project with the team."

**Insight:** High-fidelity work trials are the best way to evaluate a candidate's actual judgment, taste, and ability to collaborate on real projects.

**Tactical advice:**
- Incorporate a 1-5 day paid work trial on real projects for final-stage candidates.
- Evaluate all roles—not just PMs—on their product sense and ownership mentality.
- Assess how well candidates integrate feedback during the collaborative trial period.

*Source: [How Linear builds product](https://www.lennysnewsletter.com/p/how-linear-builds-product)*

---

> "The goal of the project is to get a taste of how a candidate approaches a new problem. Most importantly, you aren’t looking at how close they got to the right answer. Instead, you are looking at how they break down the problem, how they structure their solution, and how they communicate it to you."

**Insight:** PM interview projects should prioritize the evaluation of a candidate's structured thinking and communication process rather than just the final solution.

**Tactical advice:**
- Select a hypothetical problem related to your product to evaluate both problem-solving skills and domain interest.
- Focus your assessment on the candidate's problem breakdown and communication rather than the specific correctness of their answer.
- Decide between a take-home or day-of project based on whether you prioritize real-world research or equalizing pressure conditions.

*Source: [How to interview product managers](https://www.lennysnewsletter.com/p/how-to-interview-product-managers)*

---

**Insight:** Structuring interview questions around thematic areas like resilience and first-principles thinking allows you to extract deep insights in a short 45-minute window.

**Tactical advice:**
- Group interview questions by specific themes to ensure all essential competencies are explored.
- Look for signals like 'brutal honesty' or 'agency' in responses rather than just the outcome of the story.
- Incorporate behavioral questions that specifically focus on times when things did not go as planned.

*Source: [How to learn the most about a candidate from a single interview question](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate-from-a-single-interview-question)*

---

**Insight:** To effectively interview for the broad role of product management, use targeted questions mapped to the specific core responsibilities expected at your company.

**Tactical advice:**
- Select one specific question for each of the ten product manager 'jobs' to ensure comprehensive coverage.
- Distribute the ten questions across different interviewers to avoid overwhelming a single session.
- Tailor the selection of questions to the specific level and expectations of the PM role you are hiring for.

*Source: [My favorite PM interview questions](https://www.lennysnewsletter.com/p/my-favorite-pm-interview-questions)*

---

> "Most first PMs were previously individual-contributor product managers, or senior PMs. Very few were previously former directors, VPs, or heads of product. Surprisingly, almost a fourth were engineers."

**Insight:** The ideal first PM is typically an execution-oriented individual contributor or an internal transfer who already understands the product and customer base.

**Tactical advice:**
- Look for candidates who can effectively 'channel' the founder's vision rather than senior leaders looking to build a department.
- Consider internal transfers from engineering or analyst roles who have demonstrated strong product sense and customer empathy.
- Hire a Growth PM as the first hire if you are a product-minded founder to find a complementary skill set.

*Source: [When they hired their first PM](https://www.lennysnewsletter.com/p/when-they-hired-their-first-pm)*

---

> "The project was typically from a real-world situation we faced and solved in the past. This allowed us to know the ins and outs of the problem, which is useful when assessing and guiding candidates."

**Insight:** Basing work trial prompts on historical real-world challenges allows the hiring team to leverage their deep understanding of the problem to better evaluate the candidate’s solution.

**Tactical advice:**
- Use real-world situations your team has previously solved to ground the project prompt.
- Design tasks to be slightly over-scoped to test the candidate’s ability to prioritize.
- Keep project prompts open-ended to observe the candidate’s judgment and initiative.

*Source: [Adding a work trial to your interview process](https://www.lennysnewsletter.com/p/adding-a-work-trial-to-your-interview-process)*

---

**Insight:** Evaluation during a work trial should focus on qualities like initiative and taste that are nearly impossible to gauge through conversation alone.

**Tactical advice:**
- Look for evidence of 'good taste' and judgment that cannot be surfaced in a standard interview.
- Use the trial to see if the candidate is truly a 'builder' who can approach problems productively.
- Compare trial performance against initial interview impressions to filter for real productivity.

*Source: [Adding a work trial to your interview process](https://www.lennysnewsletter.com/p/adding-a-work-trial-to-your-interview-process)*

---

> "It’s so very hard a priori to know if someone can do the job. So we just pay them to do it!"

**Insight:** Compensating candidates for their work trial time ensures a fair exchange and helps secure commitment from high-quality talent who might otherwise opt out.

**Tactical advice:**
- Hire trialers as contractors to simplify intellectual property ownership and legal issues.
- Consider assigning small, real-world bug fixes or roadmap features to candidates.
- Compensate candidates for their time to ensure a fair 'two-way street' during the trial.

*Source: [Adding a work trial to your interview process](https://www.lennysnewsletter.com/p/adding-a-work-trial-to-your-interview-process)*

---

> "We recognized we were being influenced by aspects of an interview—such as someone’s manner of speaking or behavior in a restaurant—that have no bearing on how a candidate will actually perform. Some people are amazing interviewees and charm everyone they talk to. But if the job isn’t going to involve charming others, their interview skills don’t predict how well they’ll do as employees."

**Insight:** To convince leadership, demonstrate how standard interviews prioritize irrelevant charisma over the actual skills required for the role.

**Tactical advice:**
- Frame the trial as a necessary tool to filter for commitment and genuine interest.
- Highlight that polished interview skills are often poor predictors of actual job performance.
- Position trials as a way to gain significantly more signal and reduce the risk of a bad hire.

*Source: [Adding a work trial to your interview process](https://www.lennysnewsletter.com/p/adding-a-work-trial-to-your-interview-process)*

---

> "And don’t forget to keep your questions consistent, with predefined good and bad answers, to avoid bias. Companies should rely on a structured interview that standardizes the process among candidates, eliminating much subjectivity."

**Insight:** A structured, consistent interview process using standardized behavioral questions is essential for reducing bias and making fair comparisons between PM candidates.

**Tactical advice:**
- Ask candidates to walk through a proud project from beginning to end to evaluate their execution and reasoning.
- Request specific examples of past disagreements with engineers to gauge collaboration and conflict resolution skills.
- Define clear criteria for 'good' and 'bad' answers beforehand to keep the evaluation objective and consistent.

*Source: [How to interview product managers](https://www.lennysnewsletter.com/p/how-to-interview-product-managers)*

---

> "You can learn the most about how a person operates, thinks, and collaborates by exploring times when things didn’t go as planned. If they get hired, you can guarantee they’ll face unexpected challenges, so you’ll want to know how they’ll handle these moments before they have to tackle them on your team."

**Insight:** Probing into past product failures and ambiguous situations reveals a candidate's true mindset, humility, and ability to navigate professional adversity.

**Tactical advice:**
- Ask candidates to describe their biggest product flops and explain exactly what they did to handle the fallout.
- Evaluate resilience by asking for the hardest thing they have ever done and how they specifically overcame it.
- Test for backbone by asking about a time they had to disagree with a manager or fight against higher leadership.

*Source: [How to learn the most about a candidate from a single interview question](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate-from-a-single-interview-question)*

---

**Insight:** High-signal candidates differentiate themselves through introspection and the ability to question conventional wisdom rather than simply reciting rehearsed interview answers.

**Tactical advice:**
- Ask what conventional wisdom the candidate thinks is 'hogwash' to test for authentic, independent opinions.
- Inquire about experiments with unexpected results to see if the candidate understands customers at a deep, first-principles level.
- Tease out introspection by asking for examples of successes that worked out for different reasons than originally anticipated.

*Source: [How to learn the most about a candidate from a single interview question](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate-from-a-single-interview-question)*

---

> "The thought experiment for me is always, coming out of that, do I feel compelled to work on that problem? Right? No matter how boring it sounds on the surface, I think a really great product manager casts something. It’s like, ‘Well, this is why it’s so existential and this is why it’s so interesting, and really rallied the troops.’"

**Insight:** A PM's impact is measured not just by shipped outcomes, but by their initiative and their ability to frame complex problems as existential opportunities that rally a team.

**Tactical advice:**
- Ask candidates to define exactly what would not exist at their previous company without their specific initiative.
- Probe for releases that the candidate did not cherry-pick to understand their baseline frameworks for building products.
- Evaluate a candidate's communication by seeing if they can make even a mundane problem sound compelling and interesting.

*Source: [How to learn the most about a candidate from a single interview question](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate-from-a-single-interview-question)*

---

> "It tells me you have some humor, you’re humble, and you can point out when you’ve made a mistake. You’ve done enough to be able to confidently say, of course I’ve made a mistake. Because none of us are perfect. And you know how to spot those mistakes and you can learn from them."

**Insight:** Cultural fit is best assessed through indicators of humility and self-awareness, specifically the ability to candidly discuss personal mistakes without defensiveness.

**Tactical advice:**
- Ask for the 'worst product' a candidate has ever shipped to see if they possess the humility to own their mistakes.
- Look for 'intrinsic motivation' regarding business impact to ensure alignment with high-growth team cultures.
- Test for authenticity by breaking the 'interview mindset' with questions that require genuine, unscripted opinions.

*Source: [How to learn the most about a candidate from a single interview question](https://www.lennysnewsletter.com/p/how-to-learn-the-most-about-a-candidate-from-a-single-interview-question)*

---

> "I wasn’t exactly sure what profile I was looking for when I started, but I knew I wanted to find people who were senior enough to have had firsthand experience building world-class, successful, and impactful products (to have real-life lessons to share with others), while also not so senior that this fellowship wouldn’t meaningfully impact their career trajectory."

**Insight:** When hiring for a novel role, you can refine your selection criteria during the review process by identifying the sweet spot between proven expertise and future career upside.

**Tactical advice:**
- Review every application component, including videos and writing samples, to get a holistic sense of the talent pool.
- Look for candidates who have significant industry experience but are still at a stage where the opportunity provides meaningful career leverage.
- Balance the need for real-life lessons to share with the audience against the candidate's own potential for growth.

*Source: [Meet your Lenny’s Newsletter Fellows ✨](https://www.lennysnewsletter.com/p/meet-your-lennys-newsletter-fellows)*

---

**Insight:** Using a set of universal, non-functional interview questions helps assess character, self-awareness, and cultural fit across any role or seniority level.

**Tactical advice:**
- Ask candidates what their former colleagues would say about them to assess their reputation and self-perception.
- Identify a candidate's 'superpower' by asking what they are better at than most other people.
- Evaluate self-awareness and growth mindset by asking what specifically they are currently working to improve.

*Source: [My favorite PM interview questions](https://www.lennysnewsletter.com/p/my-favorite-pm-interview-questions)*

---

**Insight:** Evaluation of product talent should rely on assignments that mimic real-world job challenges to reveal a candidate's actual thought process.

**Tactical advice:**
- Replace abstract case studies with 'almost-real-life' assignments that reflect the actual work required in the role.
- Prioritize evaluating a candidate's customer-centricity and interpersonal style over looking for 'correct' answers.
- Use the assignment review to test how effectively the candidate can communicate design choices to a team.

*Source: [How Gong builds product](https://www.lennysnewsletter.com/p/how-gong-builds-product)*

---

**Insight:** A comprehensive PM hiring pipeline should progress through distinct screening, deep-dive, and closing stages to efficiently identify and secure top talent.

**Tactical advice:**
- Use a recruiter screen to ensure candidates meet minimum requirements and represent a cultural fit.
- Schedule a full-day interview that includes a project presentation and individual 1:1 sessions testing key PM skills.
- Ensure every interviewer blind-votes 'Strong No' to 'Strong Yes' before the final hiring manager decision.

*Source: [How to interview product managers](https://www.lennysnewsletter.com/p/how-to-interview-product-managers)*

---

**Insight:** Effective PM hiring focuses on identifying 'builders' who exhibit grit and the ability to reflect on their past work rather than those who simply follow a process.

**Tactical advice:**
- Design interview questions that probe for personal reflection on past successes and failures.
- Prioritize evidence of a builder mentality and the ability to drive projects to completion.
- Look for candidates who demonstrate 'truth-seeking' behavior over adherence to structured systems.

*Source: [How Shopify builds product](https://www.lennysnewsletter.com/p/how-shopify-builds-product)*

---

**Insight:** Hiring for 'drivers' ensures that every team member takes full ownership of moving projects forward without needing constant oversight.

**Tactical advice:**
- Screen for candidates who demonstrate the qualities of 'drivers' rather than 'passengers'.
- Evaluate all potential hires against core company values like 'Put Customers First'.

*Source: [How Snowflake builds product](https://www.lennysnewsletter.com/p/how-snowflake-builds-product)*

---

**Insight:** To effectively evaluate individual contributor PMs, narrow your focus to six essential skills: communication, collaboration, execution, strategy, impact, and product sense.

**Tactical advice:**
- Map specific interview slots to test for communication, collaboration, execution, strategy, impact, and product sense.
- Evaluate candidates for 'product sense' even if the skill is not explicitly defined on your company’s internal career ladder.
- Use the hiring manager screen to focus on the person as a human and identify the most important attributes for the specific role.

*Source: [How to interview product managers](https://www.lennysnewsletter.com/p/how-to-interview-product-managers)*

---

**Insight:** A structured interview rubric ensures that all interviewers maintain a consistent bar and helps eliminate unconscious bias during the evaluation process.

**Tactical advice:**
- Define specific 'what to look for' criteria for every question to guide interviewer evaluations.
- Identify 'flags' or warning signs in candidate answers to help interviewers spot potential issues.
- Utilize template builders to create a standardized grading system that the entire team can follow.

*Source: [My favorite PM interview questions](https://www.lennysnewsletter.com/p/my-favorite-pm-interview-questions)*

---

## Logan Kilpatrick

> "Finding people who are high agency and work with urgency, if I was hiring five people today, those are some of the top two characteristics that I would look for in people because you can take on the world if you have people who have high agency and not needing to get 50 people's different consensus."

**Insight:** High agency and a sense of urgency are the most critical traits for scaling a startup because they allow a small team to solve problems without bureaucratic friction.

**Tactical advice:**
- Screen candidates for high agency by looking for histories of solving problems without waiting for permission.
- Prioritize urgency as a core hiring trait to ensure the team can outpace competitors and navigate crises.
- Identify individuals who prioritize solving customer challenges over seeking broad internal consensus.

*Source: [Inside OpenAI | Logan Kilpatrick (head of developer relations)](https://www.youtube.com/watch?v=XkMbkWG2ca4) @ 00:00:00*

---

## Matt MacInnis

**Insight:** 

*Source: [10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling)](https://www.youtube.com/watch?v=O_W76LR77Vw) @ 00:34:30*

---

## Melissa Perri

**Insight:** Professional certifications often emphasize the mechanics of agile ceremonies over the core product management competencies required to build successful products.

**Tactical advice:**
- Prioritize candidates with practical experience in customer research and discovery over those with only technical agile certifications.
- Ask candidates to explain the strategic 'why' behind their decisions to distinguish them from process-focused practitioners.
- Be cautious of relying on CSPO or similar titles as a proxy for the ability to perform end-to-end product strategy.

*Source: How to create a winning product strategy | Melissa Perri @ 01:06:15*

---

## Melissa Tan

> "I think they looked for two main things. They looked for first principles thinkers, so not necessarily your experience, but how do you approach problems, how do you know the right questions to ask? And then create your own framework around that. Dropbox also hired for people that were just really humble, collaborative and team oriented."

**Insight:** Prioritize first-principles thinking and collaboration over specific domain experience to find candidates capable of driving cross-functional innovation.

**Tactical advice:**
- Assess for first-principles thinking by evaluating how candidates create their own frameworks rather than relying on experience.
- Look for humility and a team-oriented mindset to ensure the candidate can innovate across functions.
- Train the team to sell the company and specific roles during the interview process to close top talent.

*Source: [Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva)](https://www.youtube.com/watch?v=DoEfXj1b_ko) @ 00:43:13*

---

## Merci Grace

**Insight:** 

*Source: Merci Grace (ex-Head of Growth at Slack) on PLG, interviewing, storytelling, building a diverse team, hiring salespeople, building a growth team, and much more @ 44:46*

---

## Michael Truell

**Insight:** In an exponential growth phase, hiring too slowly can be a more significant risk to a startup's momentum than the traditional mistake of hiring too fast.

**Tactical advice:**
- Monitor growth trajectory closely to ensure that talent acquisition stays ahead of the exponential curve.
- Seek 'logic designers' who demonstrate high taste for both functional logic and user experience.
- Prioritize candidates who can operate at high levels of abstraction without losing sight of technical precision.

*Source: [The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO)](https://www.youtube.com/watch?v=En5cSXgGvZM) @ 00:51:38*

---

## Nabeel S. Qureshi

**Insight:** To attract candidates with exceptional drive, companies should project a polarizing mission that repels casual applicants while resonating deeply with those seeking high-stakes, meaningful work.

**Tactical advice:**
- Project a "distinctive bad signal" or polarizing mission that explicitly discourages people who don't share the company's core obsession.
- Screen for independent-mindedness by using founder-led, unstructured interviews that test the limits of a candidate's convictions.
- Use "murder boards" to rigorously critique project plans, ensuring leads possess both the drive and the tactical depth to succeed.

*Source: [How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)](https://www.youtube.com/watch?v=xQkSenlJvwA) @ 00:59:42*

---

## Oji Udezue

**Insight:** 

*Source: [Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform, Twitter, Calendly, Atlassian)](https://www.youtube.com/watch?v=T8TQGbJhv6Q) @ 01:01:27*

---

## Patrick Campbell

> "And so that was the other thing is we would pull all of this forward into the interview process and talk about it and basically say like, 'Hey, if this is not how you think, that's okay. We're not better than you, you're not better than us, it's just this is how we do things here.'"

**Insight:** Screening for culture fit requires being transparent about the company's specific behavioral trade-offs during the interview process so candidates can self-select out.

**Tactical advice:**
- Present a specific behavioral scenario, like handling a conflict, during the final interview.
- Be upfront about the difficult aspects of your culture to test for alignment.
- Filter for candidates who demonstrate judgment consistent with your established company values.

*Source: [10 lessons on bootstrapping a $200m business | Patrick Campbell (ProfitWell)](https://www.youtube.com/watch?v=FjLSCrSg5QY) @ 01:06:22*

---

## Pete Kazanjy

**Insight:** Replacing traditional interviews with job simulations and written tests provides a more accurate assessment of a sales candidate's actual communication and follow-through skills.

**Tactical advice:**
- Require candidates to complete written questionnaires to test their ability to articulate value.
- Use job simulations, such as mock discovery calls, to evaluate real-world sales skills.
- Look for attention to detail and consistent follow-through during the simulation phase of hiring.

*Source: [Founder-led sales | Pete Kazanjy (Founding Sales, Atrium)](https://www.youtube.com/watch?v=cZd5234Eem0) @ 00:57:12*

---

## Peter Deng

> "In 6 months, if I'm telling you what to do, I've hired the wrong person. It helps me and the person operate on a different level where the goal is not, did you hit this OKR? The Meta goal becomes, are we calibrating enough? Are we actually getting into a spot where in 6 months you're the one telling me what needs to be done?"

**Insight:** Great hiring focuses on finding individuals who will eventually drive the strategy and direct their managers.

**Tactical advice:**
- Test for the ability to take full ownership of a domain within six months.
- Focus management on calibration and alignment rather than just OKR tracking.
- Hire experts who operate at a level where they define the work rather than receiving it.

*Source: [From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng](https://www.youtube.com/watch?v=8TpakBfsmcQ) @ 00:50:34*

---

## Ryan J. Salva

**Insight:** Assessing communication skills involves evaluating a candidate's ability to convey complex experiences and new ideas with clarity and creative expression.

**Tactical advice:**
- Look for candidates who view software as a medium for creativity rather than just engineering.
- Evaluate how candidates express their experience of the world and how they communicate with others.
- Seek out cross-disciplinary backgrounds, such as philosophy or English, to find unique perspectives on product management.

*Source: [The role of AI in product development | Ryan J. Salva (VP of Product at GitHub, Copilot)](https://www.youtube.com/watch?v=awcd3P1DnX4) @ 01:00:46*

---

## Sanchan Saxena

**Insight:** Prioritize 'content' knowledge—knowing what to build—over 'process' knowledge when hiring product leaders.

**Tactical advice:**
- Evaluate candidates on their ability to identify what to build rather than just their knowledge of agile ceremonies.
- Replace traditional presentations with real-world work challenges to see how candidates think through problems.
- Determine if a candidate is a 'starter,' a 'zero-to-one' builder, or a 'scaler' to match them to the right role.

*Source: Sanchan Saxena (VP of Product at Coinbase) on the inside story of how Airbnb made it through Covid; what he’s learned from Brian Chesky, Brian Armstrong, and Kevin Systrom; much more @ 00:52:10*

---

## Shishir Mehrotra

> "I generally value the reference check over interview signals. If I had to stack rank in interviews, what is the best signal? The reference check is the top of the list. Those people, they worked with this person sometimes for years, their knowledge, what you're going to get out of 30 minutes of artificial scenarios it's just like never going to compare what a good reference check will give you."

**Insight:** Reference checks offer a high-fidelity signal of long-term performance that artificial interview environments simply cannot replicate.

**Tactical advice:**
- Stack rank reference checks as your #1 signal when evaluating candidates.
- Seek out references who have worked with the candidate for multiple years to gain deep historical context.
- Value real-world work history over performance in artificial, 30-minute interview scenarios.

*Source: [The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft](https://www.youtube.com/watch?v=7uSuMIJhONA) @ 01:15:17*

---

**Insight:** 

*Source: [The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft](https://www.youtube.com/watch?v=7uSuMIJhONA) @ 01:04:05*

---

**Insight:** 

*Source: [The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft](https://www.youtube.com/watch?v=7uSuMIJhONA) @ 00:58:20*

---

## Tim Holley

**Insight:** When hiring for product roles, prioritize candidates who exhibit curiosity, a growth mindset, and the ability to thrive in ambiguous, cross-functional environments.

**Tactical advice:**
- Look for 'collaboration excitement' as a key trait for working across engineering and design.
- Assess a candidate's ability to be decisive when faced with ambiguous data or conflicting goals.
- Hire for curiosity and the willingness to learn from peers across different domains.

*Source: [Inside Etsy’s product, growth, and marketplace evolution | Tim Holley (VP of Product)](https://www.youtube.com/watch?v=n4hRs2FsRug) @ 01:01:20*

---

## Tom Conrad

**Insight:** Better hiring decisions are made by focusing on past behaviors and natural motivations rather than hypothetical scenarios.

**Tactical advice:**
- Ask candidates to describe what a 'great day at work' looks like to understand their rewards.
- Structure questions around specific past experiences using 'tell me about a time when.'
- Avoid hypothetical 'what would you do' questions that allow for speculative answers.

*Source: [Billion dollar failures, and billion dollar success | Tom Conrad (Quibi, Pandora, Pets.com, Snap, Zero)](https://www.youtube.com/watch?v=maK0XD9ARoI) @ 01:32:56*

---

## Yuhki Yamashata

**Insight:** Hire great PMs by evaluating their ability to tell compelling stories about complex trade-offs and their command of product thinking across different altitudes.

**Tactical advice:**
- Assess candidates on their ability to synthesize controversial decisions into a clear narrative.
- Look for 'command of altitude'—the ability to move seamlessly between high-level vision and tactical details.
- Test a candidate's ability to fast-forward to an imagined future to see how they think about long-term impact.

*Source: Yuhki Yamashata @ 00:48:51*

---

---
name: interviewing-evaluating-candidates
description: Help users design and execute a high-signal interview process that prioritizes real-world performance over superficial charisma or pedigree.
---

# Interviewing and Evaluating Candidates

Move beyond resumes to assess high-fidelity signals like agency, first-principles thinking, and actual craft.

Help the user with interviewing and evaluating candidates using insights from 27 guests and posts across Lenny's Podcast and Newsletter.

## How to Help

1. **Define the Role Core** - Identify specific competencies and core jobs the candidate must perform based on your unique organizational needs.
2. **Design Practical Assessments** - Move from abstract case studies to almost-real-life assignments or paid work trials that mimic the actual job.
3. **Apply Standardized Evaluation** - Implement consistent rubrics and thematic questioning to reduce bias and increase signal quality.
4. **Conduct High-Fidelity Reference Checks** - Verify performance with past collaborators to triangulate interview signals and uncover long-term patterns.

## Core Principles

### Prioritize Enthusiastic Rehires
Brian Halligan: "I think CEOs and everyone dramatically overrates their ability to interview, and overrates their gut feeling, and underrates a really high quality blind reference."

The most effective hiring signal is asking a reference if the candidate was in the top 1 percent of employees and if they would enthusiastically rehire them.

### Use the Unsell Email
Kevin Yien: "When you get to offer stage, I send an email and I say all the terrible things that are probably going to reinforce their fears. If you can tell them that upfront and they can read that whole email and still be equally excited to join you, find yourself a A+ hire."

Send an email at the offer stage detailing your company's biggest flaws and challenges to ensure the candidate's commitment is based on reality.

### Screen for First-Principles Thinking
Melissa Tan: "I think they looked for two main things. They looked for first principles thinkers, so not necessarily your experience, but how do you approach problems, how do you know the right questions to ask? And then create your own framework around that. Dropbox also hired for people that were just really humble, collaborative and team oriented."

Evaluate how candidates create their own frameworks rather than relying on experience to find those capable of driving cross-functional innovation.

### Hire Future Strategy Drivers
Peter Deng: "In 6 months, if I'm telling you what to do, I've hired the wrong person. It helps me and the person operate on a different level where the goal is not, did you hit this OKR? The Meta goal becomes, are we calibrating enough? Are we actually getting into a spot where in 6 months you're the one telling me what needs to be done?"

Focus on finding individuals who will eventually drive the strategy and direct their managers within six months of starting.

### Stack Rank References First
Shishir Mehrotra: "I generally value the reference check over interview signals. If I had to stack rank in interviews, what is the best signal? The reference check is the top of the list. Those people, they worked with this person sometimes for years, their knowledge, what you're going to get out of 30 minutes of artificial scenarios it's just like never going to compare what a good reference check will give you."

Reference checks offer a high-fidelity signal of long-term performance that artificial interview environments cannot replicate; treat them as your primary signal.

## Questions to Help Users

- "What are the specific jobs or outcomes this hire needs to achieve in their first six months?"
- "Are you currently using a standardized rubric to evaluate all candidates for this role?"
- "What real-world problem from your current roadmap could serve as a work trial project?"
- "How are you screening for cultural traits like humility, agency, or clock speed?"
- "What is the most common reason candidates fail in this specific role at your company?"
- "How are you differentiating between a candidate's personal impact versus the success of their previous company?"

## Common Mistakes to Flag

- **Over-indexing on interview charisma** - Polished interview skills are often poor predictors of actual job performance and technical depth.
- **Hiring for domain experience over first-principles** - Relying on established playbooks prevents candidates from solving unique problems in evolving environments.
- **Treating reference checks as a formality** - References provide the only longitudinal data on a candidate's behavior and performance over years.
- **Using abstract or hypothetical case studies** - Hypotheticals reveal how someone thinks about imaginary problems rather than how they execute on real ones.

## Deep Dive

For all 39 sourced insights from 27 guests, see `references/guest-insights.md`

## Related Skills

- Hiring Product Talent
- Org Design
- Building Growth Team
- Founding Exec Team