40 Favorite Interview Questions from Some of the Sharpest Folks We Know

40 Favorite Interview Questions from Some of the Sharpest Folks We Know.jpg

by First Round

Here at First Round, we’re always searching for advice that gets overlooked or goes unshared, hoping to find the stones that company builders don’t even know to turn over.

Whether it’s through in-person events, online discussions on First Round Network (our internal Quora-style platform), or the articles and interviews we share here on the Review, we’re driven by an ambition to create the space founders and startup leaders need to exchange that “trapped” knowledge.

And in those spaces, we’ve seen time and time again how the conversation inevitably drifts back to a single topic. Whether it’s a Fast Track mentorship pairing, an intimate Co-Founder Forumdinner or a CTO unconference, hiring always seems to be top of mind.

There’s no shortage of challenges that could benefit from a dose of outside perspective, from finding hiring practices that scale to bringing on a new exec to nabbing a great in-house recruiter. And then there’s the interview.

When you’re scaling quickly, moving at warp speed, and sitting on several hiring panels, interviewing can seem like a task you just need to get through. But it’s worth pausing to remember that the decision to hire someone is an expensive and far-reaching one. And since you’re forced to make it after spending (at most) a few hours together, maximizing what you can learn about candidates in those precious few minutes becomes all the more crucial.

Of course, we’ve shared a fair amount of interview best practices in the past here on the Review. (Two particular must-reads come to mind: the seven characteristics that help you hire a top performer and this roundup of interview questions previously scattered across the Review archive).

But given the high-stakes nature of every hire, interviewing chops are always in need of sharpening. And that means our hunt for a crazy-good interview question is never over. We’re endlessly fascinated by the go-to inquiry in everyone’s back pocket, the kind that makes you want to steal it for your own hiring toolkit.

To that end, we’ve spent the past few months reaching out to some of the smartest and most thoughtful operators in our network to pose a simple question: What’s your favorite interview question and why?

The responses we got back were first class. What follows is an exclusive list of 40 interview questions, sent to us by the sharpest folks we’ve met or just outright admire. Some of the questions are (deceptively) short and sweet, some are probing and unexpected, others hinge on targeted follow-ups. Broken down by topic, they tackle everything from how candidates understand the role and process feedback to their first summer job, worst boss, and the last time they changed their mind. Most importantly, these incredible founders and company builders break down why they lean on these questions — and what to look for in the answers you hear.

We hope this collection serves as a rich jumping-off point that you can leverage as you design your own process, whether you’re building it from scratch or looking to give it a refresh as you double-down on hiring. Let’s get started.

QUESTIONS TO HELP UNPACK PIVOTAL TRANSITIONS:

1. What do you want to do differently in your next role?

When he asks this question, Instacart co-founder Max Mullen usually sees two kinds of responses — and there’s one camp that the best candidates usually fall into.

“I find that the best answers highlight what they’re running toward, rather than what they’re running from in their current job. If they launch into what they don’t like about their boss or current company, that tells you a lot. It tests whether they’re a positive person and how they handle adversity,” says Mullen.

“I also can often pick up on what interests them about our company specifically, and get a sense for how much research they’ve done. Finally, it gets into motivations — if they bring up how they’re looking for a more challenging opportunity, you can probe how they want to make an impact or the types of problems they’d love working on,” he says.

2. Imagine yourself in three years. What do you hope will be different about you then compared to now?

Julie Zhuo is a favorite of ours for a reason. The VP of Product Design at Facebook quite literally wrote the book on how first-time managers can approach building out their teams. She’s graced the pages of the Review before as well, sharing her well-honed perspective on hiring designers, and the essential (and unique) questions every manager should ask.

“At a growing organization, hiring well is the single most important thing you can do,” she writes in her book. “The most important thing to remember about hiring is this: hiring is not a problem to be solved but an opportunity to build the future of your organization.”

When we followed-up with Zhuo recently to find out what floats to the top as her favorite question after hiring hundreds of candidates over the years, her response had a similar focus on the future. “Asking a candidate to describe her vision for her own growth in the next three years helps me understand the candidate’s ambitions as well as how goal-oriented and self-reflective she is,” says Zhuo.

3. For the last few companies you’ve been at, take me through: (i) When you left, why did you leave? (ii) When you joined the next one, why did you choose it?

Kevin Weil likes to walk through a candidate’s recent career history with a unique lens. “I love this question because it helps me understand how they think through big decisions,” says the co-creator of the Libra cryptocurrency and VP of Product for Calibra at Facebook.

Weil finds he learns a lot about underlying motivations by unpacking why people leave and join companies. “What were they optimizing for that the career move maximized? Are they looking for safety, or are they eager to take risks?” he says. “Are they trying to develop new skills or perfect existing ones? Has their goal been to scale their management experience, or dive back into execution to get their hands dirty?”

Weil recommends paying special attention to how candidates cobble an answer together. “It’s interesting to see whether they weave the answer into a narrative arc or outline a series of distinct decisions,” he says. “Do they think big picture? Are they a great storyteller?”

Transitions are also Branch CEO Alex Austin’s favorite place to mine. “I find that it’s in the space between jobs when people have to make decisions entirely independently,” he says. “There’s no team member they can steal credit from or that can do work for them. It’s the only time in their career when you can get an incredibly deep insight into how they think and what motivates them. Then you can evaluate their answers against the characteristics you believe are required to succeed against the role.”

Get candidates to tell you about the transitions between jobs, rather than about each one. That’s a better window into what they value and how they make decisions.

QUESTIONS FOR SUSSING OUT MOTIVATIONS:

4. Among the people you’ve worked with, who do you admire and why?

On its face, this question might not seem to be designed to uncover motivations. But that’s exactly what Jules Walter is digging for when he asks it in interviews.

As an angel investor, product lead for Slack’s growth and monetization team and co-founder of CodePath.org, Walter stays busy pursuing the causes he cares about — and he’s interested in learning more about the values that drive folks who want to join his team.

“I want to uncover a candidate’s values, but I’ve found that asking about that directly isn’t as effective,” he says. “This question pulls out those drivers in a more subtle, yet honest way. What they admire in others tells you a lot about what they find important.”

You’ll learn a lot more about a candidate’s values by asking her who she admires. It’s a telling glimpse into the qualities she’s striving to cultivate herself.

5. Tell me about a time you took unexpected initiative. Follow-up: Can you tell me about another?

Brian Rothenberg is something of a growth guru. As the former VP of Growth at Eventbrite (and current investor at defy.vc) he’s shared the answers to the toughest growth questions and tried-and-true tactics for tailoring strategies from zero all the way to IPO.

So it comes as no surprise that his go-to interview question helps him uncover those candidates who push the bounds of their own personal growth. “I’ve found that the best people on your team consistently take initiative, even when it’s not expected of them,” says Rothenberg. “But after they give one example of an initiative in action, it’s critical to follow up by asking for anotherI want to see a pattern, whether it’s at work, school, or any other place.”

6. What’s something great about your current or previous job? Why?

bethanye McKinney Blount is a fount of company building wisdom. Across the course of her career, the co-founder and CEO of Compaas (and former engineering leader at Reddit and Facebook) has shared insights on everything from troubleshooting troublemakers in startup culture to introducing comp transparency.

“Asking this question in interviews tells me two different things,” says Blount. “First, I learn what someone loves and values — what’s important to them. Second, they nearly always follow up with a qualifier,” she says. “They’ll often say something like ‘But that doesn’t make up for…’ and so they’re also telling me something they don’t love. I find that second piece to be very instructive. It helps me understand where they feel uncomfortable, unsupported, or generally unhappy.”

7. What motivates you to work?

This one comes from Varun Srinivasan, former Senior Director of Engineer at Coinbase (where he had front-row seats to the company’s wild ascent and came through the other side with a valuable collection of lessons on scaling).

“On its face, it’s a simple question for the interviewer to ask. But it requires a tremendous amount of thought and introspection from interviewees,” says Srinivasan. “I’ve found the asymmetric nature of it unlocks valuable discussion. Great candidates will be able to articulate their intrinsic motivators and reflect on why they’ve worked at startups before — or unpack why they want to break in. Less-than-stellar candidates won’t wade into that self-inquiry. They’ll provide surface-level answers such as ‘I like hard technology challenges.’”

Jopwell co-founder and CEO Porter Braswell opt for a similarly open-ended question: What does success mean to you? “I find that asking questions like these makes the candidate pause and think,” says Braswell. “That helps drive a more organic and free-flowing conversation where I get to know the interviewee and what drives her on a deeper level compared to going through her resume.”

8. Looking back on the last five years of your career, what’s the highlight?

According to Michael Vaughan, this question is more powerful than it seems. “It tells me what type of person they are, what matters to them and how they think,” says the former COO of Venmo and current EIR at Oak HC/FT.

“For example, if they tell me about a personal accomplishment, then I know personal career development is a huge area of focus. If they tell me about the accomplishment of a direct report or the team, then I know they care about developing people,” says Vaughan. “If they tell me about a company feat, then I know that they tie their own success to the company’s success — which is a great mentality for weathering the early stages of a startup.”

QUESTIONS ON THEIR FIT FOR THE ROLE:

9. What are you really good at, but never want to do anymore?

Bryan Mason, Chief Business Officer at VSCO, is a fan of this question because it gets candidates to do three things:

  • Reflect on what they’ve learned about themselves.

  • Test their ability to speak with humility about being “good” at something

  • Talk about stuff you may find valuable on their resume, that they in fact no longer want to do.

“It’s amazing how often people answer saying they never want to do exactly what I’m hiring for in this role,” he says.

There are incredible candidates who excel at exactly what you’re hiring for. The trouble is that they don’t want to do it anymore.

10. What’s the difference between someone who’s great in your role versus someone who’s outstanding?

When interviewing candidates for LendingHome, co-founder and CEO Matt Humphrey is on the lookout for a keen understanding of the difference between A+ performance and what he calls “A+++”.

“I always follow-up with: ‘Can you give me some specific examples of this in your career and the results you saw?’ I look for how they answer the question just as much as the content of the answer itself,” he says. “The best candidates can answer almost immediately, maybe even with a wry smile because they know exactly what I’m getting at and they’re proud of doing something that was truly above and beyond.”

11. How did you prepare for this interview?

When he asks this question, Jonah Greenberger is testing for three things: proactiveness, resourcefulness, and passion.

“Those qualities are critical for almost any position,” says the CEO of Bright (a First Round-backed company). “I also like that this multi-purpose question is so open-ended. It gives room for candidates to show how concise, creative, and clear they are.”

12. What do you believe you can achieve with us personally or professionally that you can’t anywhere else in the world?

Shiva Rajaraman (CPO at WeWork and former VP of Product at Spotify) typically ask this question at the tail-end of an interview cycle.

“I like it because candidates reveal their individual motivations, creativity, and commitment to our mission all in one response,” says Rajaraman. “Often, they haven’t really thought about our company or capabilities deeply. The answers here can be revealing as to whether we are truly the best fit. It also helps cement that we are a special place for the person to thrive. Most importantly, if a candidate is able to articulate her ambitions and how we can help her achieve them, we are one step closer to closing her.”

Questions about why someone wants to work here and take on this particular role may seem routine, but they’re incredibly important. Often, candidates are fleeing something else and haven’t thought deeply about what they want next.

As the Corporate Communications Manager at Looker, a company that’s put tremendous thought and care into bringing new people on board, Tamara Ford John similarly recommends digging into what makes candidates passionate about the specific opportunity in front of them. “I always ask candidates, ‘Why do you want to work here? Why do you feel you will be good at this position?’” she says.

“I’ve found that the specifics of why someone is drawn to your company and believes they’ll succeed in a given role are often overlooked. It’s incredible how many times I’ve seen people fall down when it comes to answering these questions in interviews.”

13. What are the three most important characteristics of this role? How would you stack rank yourself from strongest to least developed among these traits?

When Jack Krawczyk is hiring for WeWork’s Product team, he’s hunting for candidates that have both a deep understanding of the role and an appreciation for the spots in which they still need to grow.

“I use this question when hiring product managers, but it can work for other roles,” he says. “I’ve found that it forces the candidate to be introspective and provide examples of how they’re a student of their craft.”

14. Tell me about your ideal next role. What characteristics does it have from a responsibility, team, and company culture perspective? What characteristics does it not have?

As the head of Square’s seller and developer business units, Alyssa Henry has her hands full, so the ability to quickly uncover alignment — or misalignment — in the hiring process is critical. Rather than asking directly about a candidate’s interest in a particular role, she’s found it helpful to abstract out to their ideal next role, a scenario that captures what they’re really after.

“This two-part question helps determine if there’s a match in expectations for the role. Particularly when you hear the answers to what they’re not looking for, sometimes you realize that the candidate is actually a better match for a different role,” she says. “But my favorite part is that it gives you the selling points you need to hit on when it comes time to close the candidate. You already know what they value, which makes it easier to tailor your pitch.”

15. It’s September 5, 2020. What impact on the business have you made in the year since you’ve joined?

When hiring for PatientPing, co-founder and CEO, Jay Desai wants to get candidates talking about the future, what the world will look like once they get the job, settle in and start making an impact.

Here’s what he’s able to learn from this question:

  • Timing: “I’ve found that it provides visibility into how long the candidate thinks things should take,” says Desai. “Folks coming from larger companies assume things take longer than they should, while someone from a smaller, scrappier startup might want to go faster than they should.”

  • Where their focus lies: “You can learn a lot from how they describe their hypothetical impact. Are they results-oriented, using numbers to describe their impact?” says Desai. “Maybe they’re more process-oriented, describing their impact in terms of the systems they’ve successfully set up. Candidates who are more people-oriented will talk about how the org will have grown and how the team will have developed.”

  • Understanding of the role: If a candidate is way off-base from your expectations when describing what they’d hope to achieve, that’s telling in a different way. “It tests the extent to which they have internalized this role and what the company is asking them to solve for,” says Desai.

The work to overcome other misunderstandings about the role and the hiring manager’s expectations doesn’t stop once a candidate officially joins the team. To continue strengthening relationships and getting to know each other, Desai relies on an incredibly tactical framework that provides a bedrock for productive employee/manager relationships.

QUESTIONS ON WORKING WITH OTHERS:

16. Tell me about a time you strongly disagreed with your manager. What did you do to convince him or her that you were right? What ultimately happened?

When we surveyed our network of thoughtful founders and operators, several mentioned this as their favorite interview question. Since they each had different points of emphasis and takeaways, we’ve combined a few perspectives here to highlight why this question packs such a punch.

Let’s start with Cristina Cordova. She joined Stripe as the 28th employee and first business development hire. In addition to joining First Round’s Angel Track program, she’s since led multiple teams across Business Development, Financial Partnerships, Partner Engineering, and Diversity & Inclusion functions — which means she’s done her fair share of hiring.

And this question has become her go-to in interviews for a few reasons. “It shows me how far someone will go in order to do what they believe is right,” says Cordova. “The way candidates choose to unpack the anecdote also shows me how they convince others in the face of obstacles. Do they use data? Do they gather support from others?” Asking about what ultimately happened is also particularly illustrative. “How they speak about not getting their way tells you a lot about whether they’re willing to disagree and commit to execution,” she says.

Current Head of People and Development at Opendoor (and former SVP of Sales at Yelp) Erica Galos Alioto leans on this question as well. “I’m looking to see how candidates deal with conflict in a work environment,” she says. “Do they openly address it and see their difference in opinion as a strength? Or are they unable to see the other person’s perspective? Do they try to resolve it or silently let it bother them? This tells me a lot about their ability to communicate effectively and how they will handle disagreements with others at work.”

Former Airbnb VP of Engineering Michael Curtis is also a fan of diving into how candidates handle disagreements in interviews. “I like this question for a few reasons,” says Curtis. “First, it’s hard to give a fluff answer to. I also find it gives me a great signal on the candidate’s personality in a number of dimensions, and it serves up useful data points that can be used in reference checks later on.”

Curtis probes deeper into the topic with targeted follow-ups that really get into the weeds of how the disagreement with their boss went down:

  • What was your manager’s reasoning?

  • What arguments did you find compelling in favor of the decision?

  • What was your reasoning and most compelling arguments against?

  • Were you ultimately right?

In addition to sharing more of his go-to questions (“Think of a time you had to cut corners on a project in a way you weren’t proud of to make a deadline. How did you handle it?”), Curtis lays out tips for focusing interviews on culture and character.

17. Tell me about the best and worst bosses you’ve ever had, specifically, in your career. What was the difference?

As the CEO of FoursquareJeffrey Glueck finds that candidates aren’t usually prepared for this question. “They often reveal what makes them tick through their answers,” he says. “While the best one is interesting for picking up insight on how to get the most growth out of them, I often find that the worst boss answer is more interesting. You might learn that they react strongly to micromanagement, are fiercely independent, or are very individual comp focused.”

The key is pushing candidates to get specific. “Don’t let them off with vague answers,” says Glueck. “They don’t have to name names, of course, but you need to insist they talk about two specific bosses at specific companies, not generalizations.”

18. 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?

Ben Kamens, the founder, and CEO of Spring Discovery (and alum of Khan Academy and Fog Creek Software) finds this question to be an effective way to probe candidates’ thoughtfulness when it comes to working with others, uncovering their understanding of how team dynamics and culture intersect.

“Do they immaturely rant about the failings of past teammates? Do they thoughtfully consider why certain problems existed, maturely discussing the tradeoffs their previous company had to make?” he says. “Can they reason through why one company or industry’s problems or culture might not apply to another’s?”

QUESTIONS ON LEARNING FROM MISTAKES:

19. When was the last time you changed your mind about something important?

For Sarah Fetter, the Executive Director of Dialog, this interview question is all about evolution.

“It allows you to see how — and if — the candidate’s belief system or set of core values has changed. How did a powerful experience or impactful person shift the candidate’s worldview?” she says. “Follow up with more questions to find out what they felt before, during and after the experience of being challenged — that will tell you a great deal.”

20. What’s the most important thing you’ve learned from a peer and how have you used that lesson in your day-to-day life?

This one comes from Dan Slate, Director of Product Management at Wealthfront. “I’m looking for a candidate’s ability to identify superpowers in those around them that they want to improve upon themselves,” he says.

“I like this question because it allows me to assess their self-reflection and growth mindset. Depending on the answer they provide, it can also be a good window into how humble they are.”

21. Tell me about a time you really screwed something up. How did you handle it and how did you address the mistake?

“In one fell swoop, this question tests for humility, self-reflection, problem-solving and communication skills,” says Chad Dickerson, former Etsy CEO turned coach-to-other-CEOs at Reboot.

He notes that it also provides greater insight into the scope of responsibility in prior roles. “The bigger one’s scope, the bigger the mistakes and the more complex the remediation of those mistakes,” says Dickerson.

22. Tell me about a time you made a mistake or failed at something. What did you learn from this experience? Can you give me two other examples?

As an alum of Glossier, the Chan Zuckerberg Initiative and Product Hunt, Corley Hughes has serious team-building chops. When hiring, she likes to focus on how a candidate has learned from failure — but she’s found that asking about it just once isn’t enough.

Asking for three examples gives me a better sense of someone’s actions and the natural way of working. Everyone who’s adequately prepared for an interview has one rehearsed answer on learning from failure in their pocket,” she says.

“The folks who can point to three different times they’ve messed up show that they have a well-honed habit of looking objectively at a situation and talking openly about what they’d do differently. I’ve found that these people tend to naturally self-course-correct, are constantly learning, and are willing to share bad news quickly, which are must-haves on my team.”

When listening to the answers, she’s specifically looking to see whether the candidate can:

  • Speak comfortably and openly about mistakes.

  • Reflect and apply what they learned.

  • Demonstrate that they don’t take themselves too seriously.

Every candidate has one canned answer on learning from failure in their pocket. The people who can point to three different examples are the true constant-learners — and the folks you need on your team.

23. When have you felt the lowest in your career? Did you realize how you felt in the moment? How did you respond?

Codeacademy co-founder and CEO Zach Sims (who’s previously shared his fundraising wisdom on the Review) is scouting for the tenacity with this question.

“We’re looking for people that know that careers have lots of ups and downs,” he says. “Can you handle those with aplomb, working through the downs with your team and the upswing that hopefully follows? Candidates that have experience with this rollercoaster can often ride out startups better than others.

QUESTIONS THAT SURFACE SELF-AWARENESS:

24. What’s one misconception your coworkers have about you?

Umbrella co-founder Sam Gerstenzang once wrote that it’s not the presence of weakness, but rather a failure to recognize it that usually holds people back — and accordingly, his go-to interview question centers around self-awareness.

“I’ve found this question tends to open up a candidate,” he tells us. “By asking for a misconception rather than something coworkers simply don’t know about you, the interviewer often receives a more important and revealing truth while also understanding how the candidate relates to their co-workers.”

In Gerstenzang’s experience, the misconception is often something a candidate wishes they had more or less of, which helps understand their underlying motivations. “A less-than-great answer often reveals an underdeveloped sense of self or poor communication with co-workers,” he says.

Asking about misconceptions is a powerful tool. It speaks to both your conception of yourself, and your understanding of how others perceive you — both of which are critical.

25. What are you better at than most anyone else? What’s your superpower and how will you leverage that to make an impact at this company?

Roli Saxena has some incredibly insightful interview questions up her sleeve. The current Chief Customer Officer at Brex (and former VP of Revenue at Clever) has previously spoken to the Review about how she hunts for resilience and prioritization to find candidates who are well-equipped to combat burnout and overwhelm.

Another one of her favorite questions similarly straddles two qualities. “By asking about their superpower and how that will specifically help them in this role, you can learn a lot about candidates’ self-awareness and how prepared they are,” she says. “If they can tailor their response to what our team is focused on and how they can add value, I know they’ve done the homework — both on our company and on themselves.”

Lenny Rachitsky is also a fan of asking candidates to share their superpowers. “As a manager, it’s important to help people flex what they’re really good at, instead of just trying to improve on the areas they’re struggling with,” he noted in his recent advice for handling performance reviews.

Here’s what the former Airbnb product lead is specifically looking for in answers to this interview question:

  • Getting thoughtful and concrete. “The best candidates take the time to pause and really think about it,” says Rachitsky. “It’s a red flag for me if they jump to stock-sounding generic answers. I want them to identify something focused, not vague.”

  • Showing humility and authenticity. “Can they honestly point out both good and bad? Do I feel like they are being real? I’m looking for an authentic insight into this person’s strengths and weaknesses,” he says. “Which is why I often tack on this follow-up: ‘If I were to ask your colleagues at your last job to tell me about you, what would I hear?’ I find that it consistently gets to real honest stuff.”

Rachitsky shared his thoughts on the role of superpowers in performance reviews, emphasizing a manager’s responsibility to describe their reports’ strengths — and how they can flex them further. Get his tactical advice (and incredibly helpful template) in this Review article how performance reviews can help managers uplevel from good to kickass.

26. If I were to go and speak to people who don’t think very highly of you, what would they say?

This question is clearly designed to probe the depths of a candidate’s self-awareness. But Gabriel Otte is also hunting for another quality: empathy.

Self-awareness isn’t just about understanding your own shortcomings. Develop empathy for the people who dislike you — otherwise you’ll get caught up in justifications and evasions that make it tough to truly internalize the criticism.

“When I pose this question to candidates, I’m always looking to see how much empathy they have for the people who don’t like them,” says Otte, the co-founder, and CEO of Freenome (and a partner in First Round’s Healthcare Co-op). “Do they evade or try to justify why people might not like them? Or are they in denial and think no one dislikes them?”

QUESTIONS TO FIND OUT HOW THEY RESPOND TO FEEDBACK:

27. What’s one critical piece of feedback you’ve received that was really difficult to hear? Why was it difficult and what did you do with that information? What did you learn about yourself?

As Medium’s Head of People, Pema Lin-Moore typically asks this question in the career history portion of the interview. “It gives me a glimpse into how a person responds to feedback that’s out of line with how they see themselves or how they wish to be seen,” she says. “You get a sense of how self-reflective a person can be, how resilient they are, and the type of environment they’ve been operating in.”

Nolan Church also similarly recommends probing into how a candidate deals with difficult feedback. “I learn more about someone from this question than anything else I ask,” says the Chief People Officer at Carta. “It gives me insight into an area for development, how they respond to feedback, and their level of introspection, vulnerability, and humility.”

In addition to providing question #11, LendingHome co-founder and CEO Matt Humphrey submitted another excellent question that also fits in here, adding a slight twist: “I always say ‘We’ll ask about this in references, but I’d love to hear it from you as well: Very specifically, what’s the most recent piece of critical feedback that you’ve gotten?” he says.

For him, the preface to the question is particularly key. “I’ve found that throwing in the ‘references’ comment is important because it tends to bring out more honest responses,” says Humphrey. “I’m literally looking for them to get into the nitty-gritty of the when and the how, not fluffy or abstract responses. So it’s helpful to have candidates know that if they lob in a softball, I may hear something different when I’m doing reference checks.”

28. Find a way to give the candidate feedback in the interview.

This one is less question, more targeted tactic, but it’s such valuable interview advice for hiring managers that we had to include it here. It was suggested by Nicky Goulimis, co-founder and COO of Nova Credit.

“In every interview, I try to find a way to give a candidate constructive feedback and see how they react,” she says. “How we navigate tough conversations is critical for how we’ll be able to work together in the future, so it’s important to test.”

It’s always unique to the candidate, so it’s hard to give one-size-fits-all advice, but here are two tactics she relies on to create an opening for a constructive feedback opportunity:

  • Feedback on the exercise: “Our business interview process typically involves a take-home that we have candidates present,” says Goulimis. “We always applaud the candidate at the end to share our appreciation, but then everyone on the interview panel goes around sharing feedback, both positive and constructive. It’s incredibly instructive to see a candidate internalize that feedback and respond to it in the moment.”

  • Feedback on their potential fit: “I also share constructive feedback when debriefing with candidates. I talk openly about what’s really exciting to me and where I still have question marks,” she says. “In addition to demonstrating my commitment to transparency, it also offers them an opportunity to react to or address those areas while they’re still being considered.”

QUESTIONS THAT PUT PASSION FRONT AND CENTER:

29. What was the last thing you nerded out on?

Shawne Ashton, VP of Growth at mindbodygreen(and former Director of Business Operations at Zola) levels this one at candidates as a final question. “It helps me get a sense of whether this person is a life-long learner, self-starter, naturally curious, and able to teach themselves new things they’re interested in,” she says. “By emphasizing that it doesn’t need to be work-related, I find that I also get to know the person a bit more beyond their direct job experience, and it ends the interview on a fun note.”

Upstart’s Head of Strategy and Partner Operations Cindy Smith asks a similar question, with a slight twist: Tell me about a topic that you’ve taken it upon yourself to learn about. “I want to hear them talk about something they’ve received no formal training on,” says Smith. “It shows curiosity, tenacity around learning and it helps me gauge how a person tackles hard topics and new challenges.”

30. What are some things outside of work that you’re irrationally passionate about?

While this question may seem like a standard getting-to-know-you inquiry, Laura Behrens Wu uses it as an opportunity to delve deeper into a candidate’s motivations.

“I’m looking for people who are intrinsically motivated, and hobbies are often an outlet for that,” says the co-founder and CEO of Shippo. “Over the years, I’ve found that intrinsically driven individuals typically have other passions outside of work that they pursue in an obsessive-like way. For example, if a candidate tells me they run 10 miles a day as a hobby, that’s a signal of a strong internal drive.”

31. What’s the first job you had, that’s not on your resume, and what did you learn from that experience?

This question is one of Maryann Kongovi’s favorites. “It relaxes the candidates and leads to fun conversations about summer jobs,” says the VP of Operations at Algolia. But there’s the intention behind it as well. “I always come away with better insight into their values and perspectives on work itself.”

QUESTIONS THAT THROW A CURVEBALL:

32. Why shouldn’t we hire you?

Romy Macasieb finds this question is a useful (and unexpected) tool for excavating where a candidate still has room to grow. “It goes much deeper than your standard ‘What are your 3 areas of improvement?’ type questions” says the founding PM and current VP of Product at Walker & Company.

“I like that it allows interviewees to play both sides of the table. They could highlight the skills they’re missing or why they might not be what we’re looking for by saying something like ‘You shouldn’t hire me if you want someone that is quant-only,’” Macasieb says. “But they can also turn the focus to why you might not be a fit for them. I’ve heard responses like ‘You shouldn’t hire me if you have an open office floor plan.’”

33. What should our team be doing differently that could yield 10x improvement?

Meka Asonye leads the Startup & SMB sales org at Stripe, a group that advises venture-backed companies on their commerce, monetization and expansion strategies. “I’m looking for folks who have a bias for action and can think like an owner,” he says. “Can they think at the CEO level, beyond just the job they’re applying for?”

Sometimes, this question surfaces some real gems. “We’re actually considering piloting one of the ideas a recent candidate mentioned. I’ve also had interviews where people have mentioned things that we have seriously considered but scrapped for various reasons,” says Asonye.

But when the answers are less than stellar, here’s where candidates tend to go wrong:

  • Ambitions aren’t lofty enough. “Oftentimes I hear ideas that are a 10% improvement, not 10X. The temptation can be to offer non-controversial, minor tweaks to the process,” says Asonye.

  • Can’t think of any suggestions. “This one is a big red flag for me, as I tend to see candidates in a second or third round interview after the candidate has met with five to 10 people,” says Asonye. “They should be pretty well-versed in our company and product by then, so it’s often a sign that they haven’t done their homework.”

To troubleshoot conversations that have stalled out, Asonye offers helpful footholds with these guiding questions:

  • Why might we be unable to raise our next round of financing?

  • Why would someone choose to work with our biggest competitor?

  • What product or service might we introduce that would be valuable to our core customer?

34. Teach me something.

This open-ended and surprising prompt was part of Nathalie McGrath’s interview toolkit while she was the VP of People at Coinbase. “It can tell you a great deal about a candidate’s thought process,” McGrath says. “How do they communicate and reason through an issue? Do they start from first principles? As an added benefit, I often get a glance into something they’re passionate about — plus the chance to personally learn something new.”

Kevin Morrill is also a fan of this approach in interviews — one that he’s built on and thoroughly thought through after asking it hundreds of times over the years. Morrill’s an engineering manager at Quizlet, former CTO of Mattermark, and the creator of Buried Reads, a fascinating newsletter that’s a must-read in our inbox.(He co-authors it along with his wife, Danielle Morrill former CEO and co-founder at Mattermark, and current GM at GitLab).

And when we asked why he favored this approach in interviews, Morrill was at the ready with this thorough Google Doc explanation on what he calls “the five-minute communication question.”

Here’s how it works: Morrill asks candidates to break down a topic for him. It can be anything — a hobby, book, or project — but they’ll only have five minutes to take him from a beginner to someone who understands what’s most important about the topic. Here’s a preview of what he’s come to look for in their explanations:

  • Empathy. As an interviewer posing this question, the key is to keep your face vacant and minimize interjections. “A star candidate will pick up on this and ask if I understand so far,” writes Morrill. “These are the same kind of people that empathize with customers and think about it in all the work they do once we hire them.”

  • Giving an analogy. Using a shortcut for explaining concepts is a telling indicator of a candidate’s skill. “One example I heard while someone was teaching me the basics of poker was to take advantage of the fact I had played backgammon, even though I hadn’t played poker. He talked about how in backgammon all the pieces on the board are exposed information that both players can see, but in poker, you have hidden information,” writes Morril. “These types of explanations go a long way towards quickly communicating an idea with all kinds of implications very succinctly.”

  • Taking the time to pause. “Once the trigger-happy type candidates get going, they don’t have any kind of bulleted list or outline in their head of what they hope to get across,” writes Morril. “What’s most incredible about this is how accurately it predicts disorganized and non-goal directed behavior on the job.”

It is amazing how many candidates won’t premeditate before diving into interview questions. Those who take the time to stop, think it through and have a few crystal clear points are amongst the best people I’ve ever worked with.

QUESTIONS THAT DIG INTO HOW THEY THINK:

35. If you were to take over as CEO of your current company tomorrow and had to increase your company’s current rate of growth, what three areas you would invest in?

Jeanne DeWitt heads up Revenue & Growth for North America at Stripe, so naturally, her favorite question has a growth bent to it. But by asking candidates to play CEO, she’s uncovered a sharp way to assess them on a few different variables.

“I’ve found it gives candidates an opportunity to highlight their strengths and strategic thinking,” she says. “But it also provides a chance for them to exercise empathy. If they get into how their hypothetical actions as CEO will affect the team, that signals a certain thoughtfulness about how their own working style impacts their peers or reports.”

36. How would you build a product for people who are looking for an apartment?

Bangaly Kaba (VP of Product at Instacart and former head of growth at Instagram) gives candidates 45 minutes to work through this one on a whiteboard. It’s part of the product sense portion of the PM interview process — and he finds that this seemingly mundane hypothetical can prove to be very difficult.

Here’s why it’s one of his favorite questions to ask in an interview:

  • There’s no one right answer. “As the interviewer, I’m agnostic when it comes to the exact product solution,” says Kaba. “What I care about is the rigor of the candidate’s approach, the depth of thinking and coherence of the product outcome, and the frameworks used to get there.”

  • It’s relevant to everyone. “Many product sense questions are niche and pertain to the company you’re interviewing for, which carries bias because there’s asymmetric information between interviewer and interviewee,” he says. “But finding housing is a universal need.”

  • It’s hard to game. “Even if you know the question in advance I can offer new constraints or twists that are similar to on-the-fly changes that PMs face day-to-day,” says Kaba. “It checks whether the interviewee can think the thorough the product idea holistically.”

37. What are 10 ways to speed up Domino’s pizza delivery?

When hiring for Coinbase’s product team, Max Branzburg likes to throw this unexpected, pizza-chain related inquiry out there.

“There’s no one right answer, but what I like about this question is that nearly everyone has the same context beforehand,” he says. “Good responses demonstrate an ability to ask clarifying questions, structure thoughts, be both creative and analytical, and consider technological and operational solutions. Plus, it’s undeniably fun.”

QUESTIONS THAT FLIP THE SCRIPT:

38. What can I tell you about working here?

A few years back at our CTO Summit, Kellan Elliott-McCrea gave an incredible talk on how Etsy grew their number of female engineers by 500% in one year. So we weren’t surprised that his take on interviewing was similarly deep and insightful.

The former SVP of Eng at Blink Health and Etsy CTO finds that the fundamental model we use to interview within the tech industry is wrong. “It assumes we’re panning a stream of high performing technical specialists for a few gems. This may have been true once upon a time, but it isn’t the world we live in anymore,” says Elliott-McCrea. “Software is a straightforward technical project, but a difficult social, cultural and operational one.”

Here’s his take on what interviewers should focus on instead:

Treating the interview as a collaboration to make sure that the role is a good fit is the first priority. Making sure the candidate has a positive experience is the second priority. Everything else is a nice-to-have.

39. If you were in my shoes, what attributes would you look for in hiring for this role?

NerdWallet co-founder and CEO Tim Chen recently shared his takeaways from navigating the shift from first-time founder to seasoned exec on the Review, which surfaced some particularly interesting insights on hiring, including how he’s revamped his approach to interviewing execs and the surprisingly honest reason why he interviewed every single person up until the NerdWallet team reached 200 people.

And when we followed up with him to get his favorite interview question, he surfaced yet another intriguing tactic: asking what the candidate would look for if they were on the other side of the table.

“Some of the attributes they list off are surprising,” says Chen. “It helps you think about the role in a different way. I’ve also found that candidates tend to highlight their own strengths, so it gives you a window into who they are. You can also get a sense of whether they’re good at breaking nebulous problems, like hiring, into the key drivers.”

40. What have I not asked you that I should have?

“This question surprises almost everyone,” says Liza Hausman, VP of Industry Marketing at Houzz. (And it’s the perfect one to end on.)

“I like it because it tells me what they think is important about their skills or experience. It also lets me know if they have an interview strategy of their own, which can be useful if they’re going to be building out a team.”

Got a favorite interview question of your own?

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