First Ipo Interview Questions

First ipo interview questions



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 Forum dinner 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.

First ipo interview questions

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.

Table of contents

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.

Got a favorite interview question of your own? Tell us on Twitter orshare it here. We’ll compile the best submissions and share them withFirst Round Review newsletter subscribers.



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.


First ipo interview questions

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 crytpocurrency 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 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.



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, 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 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.

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But after they give one example of initiative in action, it’s critical to follow up by asking for another. I 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.”


Using price action in binary options

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 upack 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 opts 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.

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“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.”


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.”



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).

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“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 (CTO at WeWork and former VP of Product at Spotify) typically asks 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.

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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.”


First ipo interview questions

What are the three most important characteristics of this function? 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 function they're in 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 functions,” 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?

2. Can you describe yourself using 3/5 words?

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.

    Interview questions to ask about their expectations:

    “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 — read more about it here.


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.

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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.

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“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 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, as well asadvice for busting bureaucracy before it starts in this Review article.

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

First ipo interview questions

What was the difference?

As the CEO of Foursquare, Jeffrey 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?”



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

For Sarah Fetter, Managing Director of East Rock Capital, 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.”


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 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.


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