The 40 Best Questions to Ask in an Interview — How to Go Deeper Than “What’s the Culture Like?”
People & Culture

The 40 Best Questions to Ask in an Interview — How to Go Deeper Than “What’s the Culture Like?”

Top startup leaders shared their favorite thought-provoking questions for candidates to ask during an interview to stand out from the crowd and gain in-depth knowledge about the company, the team, and the role.

When it comes to interviewing advice, there’s plenty to go around for hiring managers. We’ve certainly covered our fair share here on the Review — none more popular than last year's 40 Favorite Interview Questions from Some of the Sharpest Folks We Know.

Since we published this guide, it’s racked up hundreds of thousands of views and received tons of wonderfully-kind feedback, turning into something of a staple for interviewers prepping to dig in with a candidate. We were thrilled to see that getting folks to share their best interview questions — and crucially, why they ask it and what makes for a good answer — seemed to strike a chord. It confirmed our hunch that despite the wealth of content around crafting the right questions, there’s still a hunger for these resources to keep your hiring skills top-notch.

And there’s an appetite to match it on the other side of the table, of course. As a candidate, prepping for a job interview can feel like a job that’s never fully done. From shaping up your resume and settling on the key stories to highlight from your career path, to researching the company and stalking the interview panel on LinkedIn, there’s a daunting pile of prep work to tackle — and an insatiable need for advice to help get you through it.

Today we’re focusing on those moments when the interviewer turns to candidates and asks the inevitable, “Do you have any questions for me?” at the end of the interview. It's critical to come up with a slate of good questions to ask that uncover vital information about dthe job opportunity — and simultaneously serve up another chance to highlight your strengths as the ideal candidate.

But too often, interviewees fail to stand out here. There’s an easy temptation to focus on other aspects of prep and thus fall back on the most common interview questions over and over again — think “Why did you join this company?” or “What does a typical day look like here?” At best, these may elicit an interesting anecdote from your interviewer. At worst, you’ve wasted precious minutes just dipping a toe into the pool, instead of probing the most critical depths of this new role and your potential employer.

Since we’re always on the hunt for tactics and advice that can fill in existing gaps, we’ve spent the past month reaching out to some of the most thoughtful founders and startup leaders in our network for their take on this question:

What should candidates ask in interviews?

We were especially focused on unearthing the best questions that are not often raised, whether they were queries these leaders themselves have previously posed before joining a company, or ones they wish more candidates would put to them when they’ve got their hiring hats on. A few contributors will be familiar from previous Review articles, but most are new faces, eager to share their insights.

We were already big admirers of this group, but what we got in return blew us away: A wealth of favorite interview questions to keep in your back pocket, all that dig much deeper than the ones like “What’s the culture like?” that just barely scratch the surface.

Their responses span across all sorts of different categories, from the company’s future and the team’s biggest challenges, to professional development opportunities and what your day-to-day responsibilities will really look like. While some of the questions are geared towards sussing out valuable information — whether that’s red flags or indicators that it’s your dream job — others are oriented towards reinforcing your thoughtfulness to the interview panel. Not every question will be relevant to you or your role, but we promise you’ll find at least a few that you haven’t thought of before.

But while there’s plenty of variety, there’s also a clear common thread. Regardless of role, industry, or seniority, nearly all of leaders we polled were singing the same tune: Interviewees are on the receiving end of the questions, and thus have a very limited window to pose their own questions at the end of an interview. Before taking your seat across from the hiring manager, priortize around what’s most important in your new job: Company growth, personal role and responsibility, a great team and manager. Every single question you ask should clearly map back to those priorities — and pack a punch.

When jotting down the questions for your interview panel, focus on your deal breakers: What would make you walk away?

Anna Binder, Head of People Operations at Asana, takes a systematic approach here — narrowing down her list of possibly dozens of “nice-to-haves” to just the top five must-have criteria. “You need a proactive, intentional and mindful approach to managing your career. A lot of folks get caught up in a mindset that I liken to teenage dating — you get so excited that someone likes you, that you lose sight of whether or not you even like them back. Putting those five must-haves on paper puts you in the driver’s seat so you can be the CEO of your own career.”

With that framing in mind, we’ve broken this mega-list of smart questions down to eight targeted categories, based on what you might care about most in your job search. Click the links below to navigate to each section:

  • Company growth and priorities: What’s on the horizon for the company, and what are the biggest blockers to reaching that summit?
  • Culture and values: How does the company want to conduct its work?
  • Culture and values: How does the company want to conduct its work?
  • Employee experience: What factors determine whether or not someone is successful at growing within the company?
  • Founder fit: For those interviewing at early-stage startups, how do you assess whether the founding team is well-equipped for the bumpy road that lies ahead?
  • Manager compatibility: Will you and your manager work harmoniously, and will they be someone who gently nudges you to be better?
  • Role and responsibilities: Does the role adequately fulfill the next steps you’re looking to accomplish in your career?
  • Team impact and dynamics: How does the team function as a unit to drive meaningful change for the company and its customers?

We hope this serves as a rich starting block for pulling together a roster of questions that crystalizes whether the role and company in front of you is the perfect fit. Let’s dive in.


1. What’s the biggest existential threat to this business? What are the things that keep you up at night?

This straight-shooting question comes courtesy of Shreyas Subramaniam, Director of Product Management at Airbase, and should be near the top of the list for any job seeker. Regardless of your role or main priorities for your next gig, sketching out a more nuanced understanding of the business (aside from what you can dig up poking around on Google) is key to grasping what lies ahead if you join. A variation of this question popped up numerous times in our conversations (which clued us into just how valuable of a query it is), so we’ll also share a few alternative ways to approach it:

Jake Fuentes, Co-founder and CEO, Cascade

Kevin Caldwell, Co-founder and CEO of Ossium Health, likes to bifurcate the question this way: What's the biggest external risk to the company? What is the biggest Internal risk? Which worries you more?

Jake Fuentes, Co-founder and CEO at Cascade, approaches it a bit differently: If the company failed in 18 months, what’s the likely reason why? Now let’s say it’s a breakout success, what was the critical thing it did right? “I find this two-pronged approach reveals the real risk factors and opportunities for the business and — perhaps more importantly — how clear leadership is on those areas,” he says.

2. What are the most recent examples of things the company has tried and failed at?

With this question, Jeanne DeWitt Grosser, Head of Americas Revenue and Growth at Stripe, isn’t necessarily zeroing in on what the actual failure was — any startup vet knows that plenty of coal will turn up in your search for that diamond. Instead, mine for why it was a failure and how your potential employer responded. Is the interviewer honest in their answer, or trying to paint too rosy of a picture? Was the company able to pivot and right the ship? The response should also clearly articulate what the learnings were and how they trickled down across the company.

Sitting on the opposite end of the interview table, Max Mullen, Co-founder of Instacart, has been asked a related question: What were the single best and worst days/weeks in Instacart's journey? “As an interviewer you're often answering the same questions over and over — a hard question like this one gives you pause and actually makes you think of the answer on the fly,” he says.

When the candidate has the courage to ask a question that might challenge the interviewer, that’s a positive signal. I want them to ask the hard questions once they’re inside the company, too.

3. What are some of the key financial metrics that the company optimizes for?

“I don't think enough candidates ask about the business itself, regardless of the product,” says David Nunez, Head of Documentation at Stripe. “This question gives great insight into the health of the company, what they prioritize, and also reflects well on you as the candidate — you’re signaling that you really want to do your homework,” he says.

4. What are the top three customers that you’ve won, and the top three customers that you’ve lost?

We love that this question from Max Branzburg (VP of Product at Coinbase) requires a more specific answer than overly-sanitized marketing speak: “You get a real sense of how they're doing in the market, what's working well — and what's not,” he says. Key here is to also dig in with your follow-up questions: What are they doing to replicate their biggest wins, and what are the most valuable takeaways from the losses?

Kaye Mao, Interaction Designer, Google Health

5. Which companies does the leadership admire and hope to emulate? Why?

Kaye Mao, Interaction Designer at Google Health, loves this question she first heard from design vet Julie Zhuo (whose inside look at Facebook’s practices for hiring designers is still a Review favorite). In our view, it goes back to the heart of your interview process as a candidate — what’s most important in your next role? Answers here should indicate the company’s most powerful driving force, whether that be culture, hypergrowth, or delivering customer value. How closely does the company’s motivation align with your own?

6. What area of the business would you say this company is behind on, given its stage?

Cristina Cordova, Head of Platform and Partnerships at Notion, likes to lean on this question for getting a sense of the company’s bigger picture — and how that might impact your own role. “This question can often highlight functions that are not established and areas where you have to fill in cross-functionally that might surprise you,” she says.

Another way of approaching this question, also from Max Mullen of Instacart, is: If you had a magic wand, what would you change about the company?

7. What’s something that would only happen here but wouldn’t at other organizations?

This one comes from Adam Grant, bestselling author, podcast host and professor at The Wharton School. In fact, this question of his is such a hit that we got multiple submissions of it from folks other than Grant, citing him as the inspiration — likely due to the opinion piece he penned it for The New York Times: “The culture of a workplace — an organization’s values, norms and practices — has a huge impact on our happiness and success,” he says. “Values are the principles people say are important and, more crucially, the principles people show are important through their actions.” (Look for more of Grant's advice on how to standout as an original here on The Review.)

Liz Fosslien, Head of Content at Humu, is also a big fan of this question: “Grant says it’s the best way to instantly learn about the company’s culture. In my experience, he’s absolutely right," she says. "I’ve found people tend to either get an ‘Oh no’ look on their face, or they light up at the memory that pops into their head. Both reactions are strong signals about what it might be like to work there.”

8. How have you changed during your time here?

“This is an unusual one, but it will elicit some interesting insights,” says Camille Ricketts, Head of Marketing at Notion. “People might talk about how they've gotten more opportunities to learn or real mobility in their role. Sometimes they will say they've become more resilient or stronger, which is an indication of something else, perhaps. It gives you a fascinating perspective on what the culture brings out in people.”

A variation of this question comes from Nikita Miller, a seasoned product leader at Atlassian: What have you learned while working here that you’ll take with you no matter where you go next?

Laura Del Beccaro, Co-founder and CEO, Sora

9. When you’ve done your best work here, what about the culture has enabled you to do that?

Here’s another question, from Laura Del Beccaro, Co-founder and CEO of Sora, that continues to test the company’s cultural fabric — whether it supports employees like a warm, cozy blanket, or leaves them out in the cold.

10. Has the company ever made a decision that prioritized its values over revenue?

Most companies have a list of values — but whether those values actually leap off the webpage and are reflected in the day-to-day work can be a whole different story. Sean Byrnes, CEO of Outlier, gets down to brass tacks and separates hand-waving from harsh reality with this question.

Jiaona Zhang, VP of Product at Webflow, also wants to learn more about the company’s values in action. “It's definitely true that most companies have core values and that it is often hard to know what they really mean and whether they are upheld,” she says. “To get a better signal, I ask about the history of the core values; specially, I ask for how the core values have been (mis)interpreted, whether they've had to be revisited over time, and if there have been situations where they've been weaponized.”

Liz Fosslien, Head of Content, Humu

11. How did leadership at your organization respond in the first days of the COVID-19 crisis?

We love this topical question from Liz Fosslien of Humu, (who previously shared her tips for leading through emotional storms on the Review — so no surprise here that she's focused on employees' needs). “This question can reveal a lot about a company's culture. Did leadership put their people's safety and well-being first? Or did they drag their feet and then double-down on micromanaging employees?”


12. What specific initiatives has the company launched to improve diversity and inclusion?

Another contribution from Laura Del Beccaro of Sora, this question starts us off by looking at the concrete steps the company has taken to create a more equitable workplace for all. While virtually every company speaks to DEI in the form of public statements or formal plans, it’s critical to probe and see if there’s actual weight behind it, or simply talking points. Whether you identify as someone from an underrepresented background in tech or not, opening up the conversation to talk tangibles can unearth critical insights into how the company takes care of its employees.

13. What is the title of the most senior underrepresented person at the company?

Matt Wallaert, the behavioral scientist who we mentioned before diving in, leaves no wiggle room for editorializing with this question. “I focus on asking factual questions that don't have to do with how persuasive the person can be,” he says.

14. What would 1:1's be like with my direct manager? What types of topics would we discuss?

Howard Ekundayo, Engineering Manager, Netflix

While on its face, this might not seem to be a question specifically about DEI, Howard Ekundayo, Engineering Manager at Netflix, finds it can reveal how much leadership makes the effort to include every voice and show up for employees — especially when folks on their team can’t set aside external stressors when they sit down at their desks in the morning. “This question can provide insight into the degree to which a manager is inclusive, empathetic and transparent,” he says. “Our manager's style of leadership can significantly impact our overall success and growth in a specific role. Given the impact of COVID-19, the heightened coverage of systemic injustices, and anxiety stemming from the political climate (to name a few), it's important now more than ever that we can depend on the necessary level of support from leadership.”

15. How do you personally learn how to be more inclusive? What's an example of a situation in which these learnings have changed the way you do your job?

Aubrey Blanche, Director of Equitable Design and Impact at Culture Amp, and a self-described “Mathpath” (math nerd + empath) is laser focused on building a more equitable future. (You might recognize her from her previous Review interviews, where she’s gotten incredibly concrete in outlining tactics to make your DEI efforts less talk and more walk.) This interview question for candidates goes beyond the bird’s eye view of the company’s diversity and inclusion efforts as a whole, and zooms in on the individual commitment to moving the needle on these goals.

Aubrey Blanche, Director of Equitable Design and Impact at Culture Amp,

She also dives into how the team is folding DEI principles into everyday work with this follow-up question: How do you ensure that your team isn’t just building for themselves and their needs?


16. Can I see your calendar for the week?

Perhaps one of the most unique questions on our list comes from Anna Binder of Asana, but she’s got a pretty compelling argument for why this unconventional approach could unlock a vault of insights. “Time is your most valuable asset as a worker, and how your team leaders spend their time will tell you what they value,” she says.

I believe there’s truth in calendars. If someone tells you in an interview that they really care about the learning, development and mentorship of their employees, their calendar should reflect that.

“I’ve seen a CEO who blocked off time for parent-teacher conferences. I’ve seen a different CEO who was booked starting at 6am to 10pm every single day. When I interviewed with Asana’s CEO, something that really stuck out to me was the time he blocked off just for thinking and writing. He was diligent about creating the space to do the critical reflecting and strategic work that’s necessary to run a company effectively, for the long term.” (For another example of calendering prowess, we recommend checking out Front CEO Mathilde Collin’s approach.)

Anna Binder, Head of People Operations at Asana

The key to making sure this question lands, according to Binder, is prefacing it with what you’d like to glean. “For example, you could phrase this, ‘I’m really looking for a company that values learning and coaching, and makes space for those opportunities. Can I see your calendar and understand how much time you’re able to devote to working with your reports?’” says Binder.

17. What common attributes have you found among people who join and are successful, versus those who aren't?

“The answers to this question give you a lens into the types of behaviors and attitudes that are most valued — sometimes reinforcing published company values, but other times giving you insight into unstated norms,” says Michael Leibovich, Senior Director of Product Marketing at AppFolio.

Cristina Cordova of Notion also hits on this same idea with her version of this question: Can you describe someone (other than yourself) who you think has been very successful here and share what you believe made them successful? “Strong examples here can often highlight opportunities for upward mobility and detail what qualities are revered within an organization,” she says.

Another powerful way to learn which stars shine brightest and uncover what the interviewer personally values comes courtesy of a submission from a First Round community member: Who is the most under-recognized person in the company, and why are they under-recognized?

18. What are the top reasons that people have left the company of their own volition?

While questions around employees departing can quickly be brushed aside that they “weren’t a great fit” or “not well-equipped for the job,” this deft phrasing from Gokul Rajaram, product leader at DoorDash, can stir up striking conversations around clarity of role expectations and retention.

Sean Byrnes, CEO, Outlier

19. What is something that the company changed at the request of its employees that did not originate from an executive?

Another one from Outlier’s Sean Byrnes, who tackles the often broad conversation around “employee experience” by quickly narrowing the focus to simply employee impact. How much do employees have a voice? Is information flowing upward, or is the company stuck in a hierarchical standstill? While particularly valuable for folks interviewing as an individual contributor, even managers may find this question useful to look out for their future team’s growth potential.


20. Can you tell me about your founding team’s background and why you’re tackling this particular problem?

Ryan Hoover, Founder of Product Hunt, has a firm directive here:

More job candidates should think like an investor.

“After all, joining a company is one of the biggest investments one can make,” he says. Much like an investor will look closely to assess founder/market fit and intrinsic founder motivation to tackle this problem, so too should candidates when they’re hitching their career goals to a startup’s wagon.

21. If I asked your investors what they're worried about, what would they say?

Dan Pupius, Co-founder and CEO of Range, advises that you use your likely limited time with the founding team to dive deep into the startup’s short- and long-term prospects. To map the winding road ahead, he also leverages this question: What milestones do you need to hit for the next round of financing? How did you come up with those milestones?

22. Take me through key parts of your last board deck. How did you present the material to the board and what were one or two key insights from the board?

Board relationships can make the seas choppy or be a startup’s life preserver. Mike Smith, President and COO of StitchFix, recommends this question to test the waters.

23. Who is on your speed dial for when things aren’t going well with the business? Why that person?

A founder’s network of advisors — whether official, like board members, or unofficial sounding boards — can cushion some of the bumps along any startup’s path. Who the founders trust when they hit a fork in the road (and why they trust them) can reveal a lot about what they’re really looking for out of their advisors — a cheerleader, or someone who will deliver harsh truths. This question, from Vivek Sodera, Co-founder of Superhuman, assesses how robust that support layer really is for leadership.

24. Can you share the details of the company’s stock offerings for employees?

We’re folding together a cluster of questions from both Sean Byrnes of Outlier and Dan Pupius of Range that dive into the financial details you need to know before signing on with an early-stage company:

  • What is the last 409a valuation?
  • How often do you do re-evaluations?
  • Do you think there will be a secondary market for early liquidity? Who will have access to it?
  • What was the last preferred price?
  • What is the total number of stock options issued and what are the outstanding shares?
  • How much of the company do investors own?

“It’s important to ask details about the company that they should be willing to disclose to help you make a decision about whether or not to join,” says Byrnes. “Failure to share these things is a warning sign.”


Jiaona Zhang, VP of Product, Webflow

25. What's the hardest piece of feedback you've received, and what's the hardest feedback you've given?

Jiaona Zhang of Webflow previously outlined her insights on the Review for building minimum lovable products (not just MVPs) that puts the user and their feedback at the center, and it’s still a favorite among our readers. Zhang puts a premium not just on the customer’s feedback — she also wants to carefully excavate how comfortable a future manager is with criticism on both sides of the table. Here’s what to look for in the answer to this question:

  • They’ve got a few examples on the tip of their tongue. Doling out feedback should be a consistent line item of any people manager’s to-do list.
  • They talk about their approach. Candid, hard feedback should never be delivered haphazardly. How did they take extra care to create the right conditions so that this feedback could be best received?
  • Who do they typically receive feedback from? If all the examples reference the manager receiving feedback from higher-ups, you may have a hard time getting through if you’re trying to signal up the chain.

26. What relative weight do you put on the way people conduct their work, versus the work product they generate?

Matthew Metz, (also at Ossium Health as the Director of Strategic Partnerships) hammers home the emphasis on soft skills from a different angle. While plenty of cultures and teams talk about their “no brilliant jerks” policy, how is that grounded in reality? Look for tangible examples here, and use follow-up questions to prompt stories of when creating a psychologically safe environment was more important than hitting a deadline.

27. How would your team describe you?

Zainab Ghadiyali, former tech and product lead at Airbnb and Facebook

“What’s your management style?” is an all-too-common question, more likely to elicit platitudes than nuggets of wisdom — consider this minor reframing that majorly shifts the conversation, courtesy of Zainab Ghadiyali, a fount of career-building wisdom. She blazed an incredible trail as a product and tech lead at Airbnb and Facebook, and co-founded a side hustle that went on to be acquired by (She shared all of her top takeaways and advice for forging your own curiosity-driven career path on the Review last year and has her own newsletter where she shares writings on product, tech and leadership.)

“One of the top three reasons people leave a job is due to manager misfit, so during the interview it’s critical to understand what the hiring manager’s style is,” says Ghadiyali. “Framing it from the perspective of the reports prompts the manager to think beyond their intent and instead consider their actual working relationships with the team,” she says.

28. How do you cultivate and foster individual contributor growth on the team?

Joe Blau, Sr. iOS Engineer at Uber, underlines an important point here: Not everyone wants to (or feels ready to) lead a team. Some folks want to be the deep-sea divers of an organization, rather than looking down from above. Yet many companies neglect these critical individual contributor employees, instead focusing all development on building the skills necessary to one day step into management’s shoes.

29. What could I have done better during the interview process?

Kim Scott, Founder, Candor, Inc.

While not technically a question to ask during the interview, this suggestion from Kim Scott of Radical Candor fame was too valuable to pass up. “Here is advice I give people after they get a job offer. Try soliciting some feedback. Does your new boss tell you anything? You want to know if your new boss is going to give you feedback that’s going to help you grow. If the boss says, ‘Fine, everything was fine,’ that’s not a good sign. You already know it was fine — you got the job. Your question is, what could you have done better?” she says. And one final tip from Scott: “Offer some bit of feedback on what your boss-to-be could’ve done better. See how they respond. If they get angry or defensive don’t walk away from that job, run!”


30. If after 12 months I’ve failed, where did we go wrong?

Nikhyl Singhal, VP of Product, Facebook

Nikhyl Singhal, VP of Product at Facebook, most often finds this question phrased as “What does success look like in the first year?” But in his experience, he gets much clearer answers by eyeing failure instead. “The top reason why a new hire is a poor fit in a company is kind of obvious — they fail to meet the bar set for them. This angle allows me to tie together expectations, past failures for new hires, and the greatest strengths and weaknesses they see within my background so far,” he says. Singhal’s got an eye for long-term thinking — his Review article on crafting your product team at every stage of the company journey remains a gold standard for product leaders, and he’s even got his own newsletter dedicated to doling out top-notch career advice.

31. What will separate someone who is good at this job from someone who is really stellar?

Desiree Caballero, Brand Strategist at Robinhood leans on this question for assessing mutual fit — you want to work somewhere that values your skills as much as the company is looking for the ideal candidate.

It’s a favorite for Kimberly Muñoz, Engineering Manager at Slack, as well. “When I ask this, I usually get a better picture of what the hiring manager is looking for and the perceived needs of the organization,” Muñoz says.

32. Think back on a really great experience that you had with the last person who previously held this role. Why was it so great?

“This might be basic,” Jake Fleming, Lead Designer at Labelbox, wrote to us — but we think it’s anything but. “It could raise a red flag for the candidate if the interviewers cannot conjure up a great past experience with someone in this particular role. It also gives the candidate a pretty solid idea of what success looks like in this role at this company. Finally, it helps illuminate the company's ideal view of that particular role and how that compares and contrasts to the candidate’s own natural abilities and tendencies,” he says. (Of course, this one doesn’t apply when you’re interviewing for a brand-new position.)

33. What will my first 30, 60 and 90 days look like? Do you have an idea of the first problems you want me to help solve?

Alphonso Morris, Lead Product Designer, Netflix

Folks usually ask something like, “What would a typical day look like?” but you can also take the opportunity to get much more specific and sketch out a picture of how the early days will work in a new role and the milestones you should hit as you pick up steam. “Everyone wants to know what they will be working on,” says Alphonso "Fonz" Morris, Lead Product Designer for Global Conversion at Netflix. But this particular question may give you another critical cue: “It shows the candidate that the company has thought really clearly about onboarding.”

34. How do you see this position evolving as the company grows?

Ruchi Desai, Director of Operations at XCLAIM, likes that this question packs a one-two punch: “It shows that you as the candidate are thinking about the big picture, are ambitious and care about more than just the immediate tasks in front of you,” she says. “Conversely, it gives you insight into how the manager views the position — is the team merely filling an immediate need and piling on unwanted tasks, or is it critical to achieving the company’s vision and mission?

Camille Ricketts of Notion also thinks a powerful way to stand out from the candidate pool is with this variation of the question: If I were to succeed in this role, what would be true for the company? “It makes it clear that you as the candidate want to connect your work to meaningful impact and have an authentic desire to understand what the company needs. It sends the signal that you want to be accountable for making real things happen,” she says.


35. Talk me through a project that initially went off the rails that you are really proud of.

Carly Leahy, Co-founder and CCO, Modern Fertility

Carly Leahy, Co-founder and CCO of Modern Fertility, knows full well that some of the biggest company game-changers started off on shaky ground. But with the right team in place, it doesn’t have to mean the project is destined for the trash bin. “I love seeing how people can be flexible and nimble and make lemonade out of lemons,” she says.

Carl Narcisse, former Senior Technical Recruiter at Slack, also wishes more candidates would ask about the missteps — they often tell you a lot more than the times everything went smoothly. He emphasizes how the team extracted learnings with his version of this question: What’s one project in the past year that hasn’t gone as planned? What were the challenge areas, and how did the team learn from that?

36. Could you tell me about a time when a co-worker went out of their way to do something nice for a teammate?

It’s unlikely that anyone on your interview panel will come out and state frankly that the team culture could use some work. This question, from Kevin Deggelman, Senior Software Engineer for the San Francisco Giants and former head of product and engineering here at First Round, gets to the heart of what makes teamwork shine — it’s not necessarily planning fun offsite events or eating lunch together everyday, it’s being kind to one another. “This is a great question to assess the culture of the prospective team. During the interview process the company is trying to figure out what kind of teammate you'll be, but it's often hard for yourself as the candidate to assess what kind of team you’ll be joining,” he says.

Lindsey O'Niell, Director of Product of Crossbeam

Lindsey O'Niell, Director of Product of Crossbeam, still remembers when she found herself on the receiving end of this question in a hiring process. “I had a candidate ask me what the last nice or helpful thing I did for a coworker was. It completely took me by surprise and I thought it was a unique way to get a sense of the culture at a company and showed how thoughtful the candidate was about being a supportive teammate.”

37. How does the team deal with two urgent projects with conflicting deadlines?

“This is especially important for candidates interviewing for leadership roles, because resource and time constraints are common in startups,” says Todd Sundsted, CTO of Odeko. “The answers, and how the interviewer backs it up with experience, help me understand their tactics for balancing conflicting demands. I want to understand how they weigh these priorities or when they push back. It's almost always an equal-parts entertaining and valuable conversation.”

38. Who owns the goals and how are decisions made about what work needs to be done? What influence do I have towards the goals set for the department?

Raven Jackson-Stone, Product Manager, Root Insurance

At its core, delivering impact as an employee involves hitting your goals. But you also want to make sure that you have a seat at the table when those goals get drawn up in the first place. This question, from Raven Jackson-Stone, Product Manager at Root Insurance, gauges the level of influence that each employee has on the team — look out for answers that seem to indicate all OKRs come from the top-down, with no input from those that actually execute the directives.

39. In what ways could the team that I'm joining improve to be more impactful and deliver more value for the business, its stakeholders and its users?

“Ideally, the team you may join needs someone of your skill-set, background, experience and unique contributions. With that said, not all managers or leaders have done the work to identify where their team is weak,” says Howard Ekundayo (Netflix). “Additionally, the manager may not have the organizational decision-making power to make targeted hiring decisions even if they did do this work. The context around this question may significantly impact your decision to join the company, organization and team overall.”

40. How long did decision-making take with the most recent large decision?

Anna Binder (Asana) leans on this question to gauge speed and organizational effectiveness — but with a caveat here. “Speed is of course really important to being a nimble organization. Four weeks is probably too long for launching an A/B testing experiment. That being said, you also want to look out for chaos and lack of a fine-tuned strategy — if they launched a new product in two weeks, that could be a red flag, too.”

Jiaona Zhang of Webflow also wants to understand scenarios where the leadership team has disagreed and committed. “It’s really telling when you hear about a decision and what happened after the fact — I often learn that teams think they’ve disagreed and committed, when in reality, they never fully committed,” she says. “It leads to side-conversations amongst the team that can fester into churn-inducing behavior.”

Cover photo by Getty Images / Mohd Hafiez Mohd Razali / EyeEm.