20 Underrated Qualities to Look for in Candidates — And 50+ Interview Questions to Suss Them Out
People & Culture

20 Underrated Qualities to Look for in Candidates — And 50+ Interview Questions to Suss Them Out

We've rounded up a curated set of attributes you may be overlooking in your hiring process — and the interview questions you can use to surface them.

You likely won’t be surprised to hear that hiring has been heating up lately. You’ve read all of those articles about “The Great Resignation” wave sweeping across the country. You’ve seen countless “I’m hiring!” posts from your network on Twitter and LinkedIn. You’ve perhaps been tapped to join more interview loops yourself, as your company revs up its own recruiting machine.

This trend has (anecdotally) resulted in some unusual practices — think larger-than-usual referral fees, bigger-than-ever signing bonuses, or outsized counter-offers in an attempt to get current employees to stay put. The high-stakes nature and weighty choice behind every hiring decision is crashing into the sheer volume of interviews and competitive pressure to lure in the best candidates. In other words, in a hiring climate like this one, it’s tempting to take some shortcuts.

In our view, if you’re a hiring manager, this is the perfect time to check in and rededicate yourself to running an even better process, whether that’s by doubling down on your existing approach or trying out new hiring tactics that break the mold.

In particular, there's an opportunity to reconsider the very qualities you’re hunting for. Because, let’s be honest, when you ask founders and startup leaders what they are looking for when hiring, a steady set of (rather unspecific) staples usually crop up: High-performer. Driven. Mission-aligned. Team player. But that’s just scratching the surface. There’s a bevy of more targeted, under-the-radar qualities to add to your list — and there’s certainly room to dial in your search by tailoring it to both your company’s culture and the realities of how the workplace has changed since the onset of the pandemic.

If you’re looking to shake up your hiring process and bring a fresh eye to your conversations with candidates, we’re here to help. Over the years here on The Review, we've interviewed hundreds of startup leaders, collecting their go-to interview questions along the way. In the past, we’ve shared several interview question sets you can lean on (like this one and this one). But we thought you might appreciate a curated compilation that’s tailored around those attributes you may be overlooking in your hiring process.

That’s why we set out to collect the answers to these questions: What are those underrated traits that you should be looking for in hiring — especially in the early-stage startup context? And how do you unearth these unsung attributes in the interview process?

We hope this roundup from our archives surfaces fresh perspectives and steal-worthy interview questions that you can add to your own rotation. From how a candidate approaches leading teams, to their motivations, unique habits, and the particulars of their operating style, this collection highlights the qualities that should be on your hiring checklist — and the interview tactics that will help you figure out if a candidate has them in spades. Some tips are function-specific, others are targeted to candidates for leadership or individual contributor roles, but many apply across the board. Let’s dive right in.


1. Embrace change and exhibit adaptability.

No surprise that we’re starting with this one. The shift to remote work — and the emotional upheaval that’s accompanied it — has been the defining theme since we’ve (somewhat) settled into these times without precedent.

Several years ago, we interviewed Anne Dwane on this very topic of adaptability. The former ​​CBO at Chegg (and current co-founder and partner at Village Global) has had to adapt many times over in her career as she's started and sold companies. She’s been able to transform herself into a constant learner — the best way to adjust to any new environment or role quickly and effectively.

“When you boil it down, learning is about changing your mind,” she says. “The most powerful way to construct a job description is to clearly communicate that unyielding, consistent learning is a core part of the job.”

To spot those with an aptitude for adaptable learning, Dwane asks these questions:

  • What have you started?
  • How would you describe yourself in your own words?
  • How would a colleague describe you in three adjectives
  • What current trends are you seeing in your profession?
  • What new things have you tried recently?

The last two questions can help you get a better sense of whether a candidate is self-motivated to explore and embrace new trends, routines, and technology — which is why Dwane recommends probing more about the new process they introduced, why it intrigued them, and the results of implementing it.

Photo of Marco Rogers
Marco Rogers, Director Of Application Engineering at Mode.

Adaptability is also a slice of what Marco Rogers focuses on in interviews. (And as a Director of Engineering at Yammer, Clover Health, Lever, and more recently, Mode, he’s got plenty of experience with recruiting.) While some discount these kinds of “softer skills” when it comes to hiring engineers, he’s quick to disagree, and chooses to dig into this area with the questions below. (We’re focusing on his questions for assessing adaptability here, but make sure you read our interview with him for his full recruiting playbook)

  • Does the candidate know that the goal of a business is to grow and change?
  • Have they been a part of a team that has grown where the process has had to change or the team has had to be restructured?
  • If so, how have they reacted to those changes?
  • Do they seek opportunities for their growth in that change?

2. Can get their team to open up (remotely).

In addition to assessing general adaptability to ever-changing circumstances, a key part of hiring now hinges on sussing out a candidate’s ability to do the job virtually — especially if they are interviewing for a management or leadership role.

Maggie Leung is the perfect person to turn to here. At NerdWallet, she spent nearly eight years building out the 80-person fully remote content team — giving her tons of  material to create a remote leadership crash course for executives.

Here’s a preview of her advice for incorporating remote work criteria into your hiring process: “You want to ask about initiatives they drove, how they managed time, how much guidance they needed, how self-starting they are, how they got buy-in from various stakeholders and took into account different perspectives,” says Leung. “You want to assess how well someone communicates and builds trust or handles friction or problems. That’s because thriving while working remotely requires hard and soft skills over and above what’s needed in an office setting.”

Photo of Maggie Leung
Maggie Leung, Executive Editor of Future.com at a16z

But building that trust is trickier than ever. “As leaders, it’s easy to forget that folks on our teams often default to thinking they are the only ones who are nervous or anxious,” she says. “So whatever tactics you use — and the possibilities are endless — the key is to get people comfortable with talking to both managers and teammates. Then people can empathize and share ideas about how to deal. And managers can better target their efforts to help.”

That’s why an ability to create space for conversations is key. Consider asking candidates for management or leadership roles how they might go about doing that, whether in 1:1s or larger group settings.

You have to anticipate and try to calibrate emotions as much as workload. FOMO, anxiety and isolation are all things managers must take into consideration if remote teams are going to perform sustainably over months or years.

3. Care about empathy.

There’s a lot of corporate rhetoric about the importance of empathy. But in Mark Frein’s view, there’s a nuance to this that’s often overlooked: hiring leaders who truly care about empathy, and want to get better at it.

“It’s really important to me to make sure that people understand that one of their most important roles as a manager is ensuring their people feel heard and empathized with. And it's harder over the screen. It takes a little bit more effort to punch through and connect with people on the other end,” he says.

“There are leaders who are very talented at creating a safe environment naturally. There are leaders who aren't. And then there are leaders who don't care about it. I can help a leader who cares about this but maybe isn't naturally gifted get better at it. But I haven't yet figured out a way to get someone who doesn't care about this to care.”

As the former Chief People Officer at Lambda School, InVision, and Return Path, Frein is speaking from a deep well of experience here. Here’s his go-to, empathy-driven interview question:

“You can start with the ‘Tell me a story when something didn't go your way’ behavioral question, but some follow-ups that can really help you get a little bit deeper are: ‘Talk to me about how that impacted you. How did you feel?’ You can really catch someone when you ask them how they felt about something that was a struggle. Sometimes they blank and don't even remember how they felt. Or they’re surprised that you care about how they feel, or they don't even know how to answer that,” he says. “Often they don't really think it was a failure — watch out for when you ask them about their emotional journey and they can't talk about it with feeling.”

If a candidate isn’t capable of being in touch with their own emotions and self-reflective about a time they failed, it's highly unlikely — especially as a leader — that they will create environments where their people can be in touch with their emotions either.

4. Tell true tales of failure — not humble brags.

Photo of Corley Hughes
Corley Hughes, CFO at SonderMind

Corley Hughes relies on a similar line of inquiry, but offers up this slight twist: 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?

“Asking for three examples gives me a better sense of someone's actions and natural way of working. Everyone who’s adequately prepared for an interview has one canned answer on learning from failure in their pocket,” says the current CFO of SonderMind and alum of Glossier, the Chan Zuckerberg Initiative and Product Hunt. “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.”

In building Thumbtack, Marco Zappacosta has hunted for this exact trait. When interviewing candidates, he leans on two different questions, always paired together:

  • What professional achievement are you most proud of? “I ask them to take me really deep, so it’s not just like ‘Oh I’ve grown a lot in my career.’ I want to hear the specific thing that happened at your job and why you’re really proud of it. I want to know what your role was and what you uniquely brought to the project,” he says. “I’m trying to get a sense for how ambitious this person is, how balanced they are in assigning responsibility for success amongst the team, and how honest they are with whether it was just up and to the right, or if there were challenges along the way.”
  • What’s your biggest professional regret? “Typically someone is riding high off the last question because they got to brag and go deep on something they feel really good about, so this next question often surprises people,” says Zappacosta.

He finds the response to the latter typically goes one of two ways. “One is the person says, ‘Oh man, there’s one thing that instantly comes to mind. It’s hard to talk about, I’m not proud of it, but I’ve been able to really reflect on it,’” he says. “Then we can go really deep and talk about what they learned.”

But more frequently, he hears something different. “It’s often like, ‘Oh, I only got a B but I really wanted an A. Or this thing was only a modest success, not a tremendous success.’ It’s just one more chance for them to brag,” he says. “I’m very turned off by those types of answers. It means they’re either not self-aware, or they’re not self-confident enough to own their mistakes.”

I’m under no illusions that I’m hiring perfect people, but I want to make sure I’m hiring people who are self-aware of being imperfect.

5. Keep DEI top of mind.

Photo of Aubrey Blanche
Culture Amp's Aubrey Blanche

While diversity, equity, and inclusion may have been previously cast as more of a corporate-level type initiative, that lens overlooks the opportunity for individuals — both ICs and leaders — to get involved and truly bring DEI strategies to life in every corner of the company. The increased awareness around the importance of anti-racist and inclusive leadership has helped right-size this perspective — but it’s still a skill-set that's often left out of the hiring assessment.

Aubrey Blanche, Director of Equitable Design, Product & People at Culture Amp has previously offered very concrete tactics to make your DEI efforts less talk and more walk here on The Review — and these two interview questions are no different:

  • 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? It goes beyond the bird’s eye view of the company’s diversity and inclusion efforts, and zooms in on the individual commitment to moving the needle on these goals.
  • Blanche also recommends diving into how DEI principles are folded into everyday work with this follow-up question: How do you ensure that your team isn’t just building for themselves and their needs?

Sally Carson agrees. When unpacking how she prepared Duo Security’s product design function for hypergrowth, Carson shared how the company baked this focus into the hiring process. “We crafted questions to assess whether every candidate, particularly candidates for manager roles, valued diversity and inclusion as much as we did, making it a part of our rubric,” she says.

“The purpose of the interview questions is to uncover whether a candidate has meaningfully thought about these issues. Do they have a mature language and perspective when they talk about it? Have they thought about the purpose of DEI, beyond the surface level? If it’s clear they’ve never given a passing thought about DEI until now, that’s a strong signal that they aren’t for us.”

6. Sell the team, not themselves.

Photo of Adam Grant
Adam Grant, bestselling author and organizational psychologist

Adam Grant favors focusing on humility when hiring. The organizational psychologist, bestselling author, and professor at The Wharton School takes inspiration from an unusual source: Butler’s basketball program. Their signature focus on humility all starts with recruiting — and key pillars include keeping big egos off the team and not sacrificing culture for talent.

Grant unearthed a great recruiting question their scouts use to surface true humility: Would you rather your team win but you only score 5 points, or score 20 points but your team loses?

He adds two more to the interview list:

  • "Who do you owe your success to?" When listening, see if the candidate uses words such as “I” or “me” a lot, instead of giving credit to others. Also watch out for phony humility from people looking to game the system or name drop. “What differentiates a faker from a truly humble person is often that the fakers are really focused on impressing you and managing up and kissing up. So they will name people above them in the hierarchy,” says Grant.
  • "Who have you learned the most from in your career?” A mark of humility is a willingness to learn from someone who might not be in a position to teach you anything. “Humble people recognize you can learn from anyone and everyone,” says Grant. “Take the student who was admitted to Yale and who asked his school’s janitor to write his recommendation letter. The appreciation and curiosity that the student showed towards somebody who's literally at the bottom of the totem pole in that high school. That's humility.”
Humility isn’t insecurity. It’s just recognizing that if you step on the brakes or take your foot off the gas, there will always be other people who won't. Or there will be products that you'll end up responsible for that don't live up to your standards.

Jim Patterson adds another layer of nuance here. (He’s the former Chief Product Officer at Yammer and CEO of Eaze — and he’s got a wonderful take on why chefs and soldiers make the best PMs.)

“I can tell who the 'mid-level' people are. They're always selling themselves. They want to make sure that I know all the things they're working on and how hard they're working. The top PMs understand if your team is bad, you're bad. When things go well, you want a PM who gets out of the way and points to everyone else. Not everyone is capable of this,” says Patterson.

Like Grant, Patterson also recommends paying attention to the words a candidate uses. “People can't help it. I'll actually start to count the number of times they say 'I' and 'me' or 'we', 'my team' and 'us.' I've been in interviews where someone says 'I' 50 times — 'I did this, I did that.' They came from a big company. There's no way they did all of that alone.”


7. Look for ways to improve processes and reduce administrative burdens.

Photo of Farhan Thawar, VP of Eng at Shopify
Farhan Thawar, VP of Eng at Shopify.

Shopify’s Farhan Thawar has a slew of must-have attributes and insightful interview questions for you to consult when you’re specifically hiring a VP of Engineering. But many of them cut across functions and apply to leaders of all stripes.

He recommends starting by assessing a candidate’s optimization skills and their favored processes. “This doesn’t necessarily mean they will force this process onto your company (well, maybe), but it’s good to have strong opinions and their own toolbox of process techniques to try out,” Thawar says. “A strong leader must know whether to experiment with ideas like pair programming, daily standups, remote work, flex time, weekly retrospectives, frequent one-on-one’s, quarterly themes, and so on.”

Good process is like a traffic light. It may slow down the commute for a single driver, but it optimizes the system for everyone on the road.

Reducing admin burden is also critical. “Leaders also need tools for winning and keeping trust. Back in 1968, The Harvard Business Review (HBR) published a seminal article on how to motivate employees. Many of the lessons still resonate today. The most notable finding is that employees can become greatly dissatisfied based on company policy and how it’s administered. Good leaders must reduce this dissatisfaction, and it’s an especially urgent need in engineering,” says Thawar.

To surface strong experimenters and unblockers, he suggests asking these questions in your interviews (tweaking to your own function, of course):

  • Describe the development process at your last company. What would you try again and why? What would you not try again and why not?
  • What have you changed your mind about when it comes to the development process or engineering team practices?
  • Describe a shitty system at your last company. What did you do about it?
  • On larger teams, how do you get a sense of what’s working and not working?

8. Challenge the defaults.

Adam Grant recommends looking for similar traits in a candidate, albeit he frames it a bit differently.

He advises scouting for “originals”, the non-conformists who help propel a company to success. He specifically advises asking these questions to find IC-level candidates who challenge the defaults:

  • How would you improve our interview process? “It's an opportunity to see if they’re willing to speak up. It's also a window into their thinking process. When they encounter something that they don't like, do they have the instinct not only to raise why it may be broken but also suggest how it can be better?” asks Grant. “It's a chance to learn about their tendency to share opinions that might be unpopular but beneficial. It gives you a little bit of perspective on their ability and inclination to improve their environment.”
  • Tell me about the last time that you encountered a rule in an organization that you thought made no sense. What was the rule? What did you do and what was the result? “You’re not excited about candidates who just let it go. But you also don’t want somebody who says, ‘Yeah I saw this rule, marched into my boss’ office, argued and quit over it,” says Grant.

9. Can iterate and introduce change.

Photo of Nikhyl Singhal
Nikhyl Singhal, VP of Product at Facebook

This additional offshoot of process-based questioning comes from Nikhyl Singhal, the former Chief Product Officer at Credit Karma and a current VP of Product at Facebook. His playbook for product teams at every company stage is a must-read for founders and product leaders, but much of his hiring specific advice spans the org chart.

Particularly when hiring in the post product/market fit phase, Singhal recommends looking for candidates who know how to introduce that right level of structure the company will need. “When a startup begins to scale and there’s a focus on product depth and quality, process starts to actually matter — even though process is what many came to a startup to avoid. Half the job is figuring out what successful execution and predictable delivery looks like. You want someone to come in say, ‘We need to start setting goals, building the right communication habits and getting the right people around the table,’” he says.

Knowing what good process looks like and knowing how to introduce it to a company that doesn't have it are two entirely different skills.

You need to have soft skills and a sense for how to navigate the challenges that come along with that,” says Singhal. “Most candidates coming from successful product orgs didn't create the process, they just followed it.”

To hunt for these critical skills around introducing change, ask candidates about a time when a process was introduced and how it went over on their team. “I want to hear answers like, ‘Let me tell you how we used to do it and how we do it now,’ or ‘We tried making this change, but it really backfired, and here’s why it went wrong,’” he says.

The ability to iterate on something until it works is underrated.

10. Focus on outcomes, not shipping.

For Tyler Hogge, it’s less about the process, and more about the outcome. While the ability to create successful execution and predictable delivery are essential qualities in a PM, this Divvy and Wealthfront product leader is looking for much more when it comes to his hiring wishlist. “The main goal for a product manager is not simply to ship software — it’s to deliver business outcomes,” he says.

We’re focusing on his go-to interview questions to suss out this quality of course, but be sure to check out his entire guide for building an outcome-oriented product org — it’s full of interesting strategies on how PMs can sell and be incentivized by revenue targets.

Here’s the trio of questions and follow-ups Hogge leans on:

  • Question: What achievements or outcomes are you most proud of as a product manager? “This identifies whether they are outcome-driven. If they just talk about shipping stuff without any clear measurable outcome, they’re not of the mindset that we need,” says Hogge.
  • Follow-up: What did that achievement result in? “Some PMs can take that next step and say, ‘Well, it resulted in X amount of revenue.’ That’s better than some answers, but then you’ve got to go even a level deeper,” he says.
  • Additional follow-up: How did that result compare to what you said it would do? “This is where most PMs struggle, because they often don’t define clear and measurable outcomes up front, so then they’re not sure how it compares to what was expected. A great answer here might be, ‘We wanted to get to 50% adoption by the end of the year, and we actually got to 65%.’ There’s clear context for success and what was achieved.”
Great candidates can rattle off the results of each product they’ve helped ship.

11. Will help you avoid bureaucracy.

“When things break, you want people who will be motivated by solving problems — those are the people who won't pause to place blame, and blame is wasteful,” says Michael Curtis. We’d recommend taking his word here — as an alum of AltaVista, AOL, Yahoo, Facebook, and Airbnb, he’s a veteran of some legendary Silicon Valley giants, and an expert at chopping through red tape.

Several years back, he shared his playbook for beating bureaucracy here on The Review. Interestingly enough, upon a re-reading, this sentence stands out: “Your hiring process is where you can take the biggest strides toward preventing bureaucracy.”

​​The most important question that you have to answer when you're hiring somebody is ‘Is this person going to be energized by unknowns?’

To dig in, try figuring out what doesn’t give a candidate energy. Ask them about difficult experiences, or moments when they were somehow not in control. Some of Curtis’s go-to questions are:

  • Describe a time you really disagreed with management on something. What happened?
  • 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?

This exercise is all about reactions. “Does the candidate start pointing fingers and say, ‘This is why I couldn't get my job done, this is why this company is so screwed up’? Or do they start talking about how they understood another person's point of view and collaborated on a solution?” says Curtis.

Adam Grant also advises taking a similar tack, adding this question: In which job were you most miserable? Why and how did you deal with it? “This not only gauges attitude, but also reveals the triggers of discontent. If hiring originals, I want people who are frustrated by red tape more than people who are bored,” says Grant. “People who say, ‘This work is boring; I hate it’ are less likely to bring originality than those who say, ‘I don't like it, but I'm going to fix it.’”


12. Apply a long-term lens.

Photo of Todd Jackson
First Round partner Todd Jackson

Why do you want to work at this company or on this product?” is a classic formulation of an interview question. But when Todd Jackson was hiring product managers across his career at Google, Facebook, Twitter and Dropbox, it was all about analyzing the answers.

Here’s a weaker response: “X industry/company is getting a lot of buzz. Everyone is talking about it. It’s really hot right now.”

And here’s what Jackson considered to be a good answer: Clearly passionate about the industry, company or project. Specific ideas and plans for what they’d want to do and how they want to make things better. This indicates that they really did their homework and have thought deeply about the company.

In particular, keep your eyes peeled for long-term thinking, which indicates commitment to the industry or type of product. For example, is the person talking about what robots or drones will look like in 5 or 10 years? Or do they just talk about how robots and drones are exciting now?

You want people who are excited about the space, not just this one opportunity.

Here are some more concrete examples of responses to look out for:

  • I’ve always wanted to work in X industry, I’ve done Y and Z in the last couple years to really prepare for this career move.
  • Company X has a huge competitive advantage because of Y.
  • I have been using product X for a while, and I really like feature Y. I think feature Z could really improve growth/engagement/monetization and here’s why...

13. Are fueled by curiosity.

Instagram co-founder and CTO Mike Krieger learned to focus on hiring passionate and flexible generalists when building out the company’s engineering org. In particular, he was looking for candidates who “embodied the startup ethos of ‘I have an idea, and I will learn anything to make it happen.’”

In Krieger’s experience, this quality correlates closely with general and obvious curiosity as a basic personality trait. So start by listening for signs of natural inquisitiveness. “The candidates we got excited about were the ones who would say, ‘This week I was really interested in the game Go, so I built a Go prototype and learned this thing.’ Rather than, ‘Well, the company I work at uses React, so I'm using React.’”

You can further suss this out with these questions, especially at the early stage, Krieger says.

  • What are the side projects you're excited about?
  • When was the last time you went down the rabbit hole on a particular project? What did you learn?
When people's eyes light up and something excites them, you’ve hit on passion and not just vocation. You need passion early on, because the work will definitely not fall into a small box.

Looker’s Lloyd Tabb offers up a different way to get at that underlying passion, especially with more technical hires. “Throughout the years, I’ve met candidates that have over- and under-estimated their abilities, but their answer to one simple question has never steered me wrong to date. I ask them: Tell me something that happened at work in the last year that made it a truly great day.”

The purpose is two-fold. It prompts an answer that shows rather than tells, allowing the interviewer to draw her own conclusions. But more importantly, it separates their powers from their prowess. “Technologies change. Startups come and go. For the long-term success of both the engineer and me, I’m interested in what fuels the person, more than their last achievement. Then you can start to see where the love of work is coming from and the very depth of what inspires them,” says Tabb.

14. Are clear on the things they don’t want to do.

Bryan Mason always poses this simple question to candidates: What are you really good at, but never want to do anymore?

The former Chief Business Officer at VSCO and current VP at True Networks finds that it gets candidates to 1) reflect on what they've learned about themselves, 2) test their ability to speak with humility about being “good” at something, and 3) 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.

Todd Jackson asked a similar variation when interviewing PMs: What aspect of product management do you find the least interesting? Here’s how he assessed their answers:

  • Weak answer: A PM who complains about doing nitty gritty work (e.g. taking notes, scheduling meetings) and implies that these things are beneath them.
  • Good answer: A great PM understands that they need to lead from the back, and they relish their role as an unsung hero. The candidate doesn’t have to say they love the tough nitty-gritty stuff, but they should get points for acknowledging the grungy parts of PM work and why it’s important to be in service to the team and mission they’re supporting.


15. Exhibit thoughtfulness.

Photo of Julie Zhuo
Julie Zhuo, co-founder of Sundial

When hiring designers back in her Facebook days, this attribute was at the top of Julie Zhuo’s wishlist. “The mark of a really great designer is that every decision they've made has a purpose, has intentionality,” she says. To get at whether someone truly possesses this quality, Zhuo asks a few favorite interview questions:

  • Think of a long-term project. If you had two more months to work on it, what would you have done differently? What would you have added or continued to refine? Thoughtful candidates are the ones who have been so attached to a project that they’ve thought many many times about how they could have made it better. “Occasionally you’ll get people who’ll say what they ended up with was perfect and they’d change nothing, or who suggest very minor cosmetic changes, which doesn’t come across as super thoughtful,” she says.
  • Pick an app or a product you love — why do you think the person who designed it made the decisions they made? Do you agree with them? “We want someone who can dig into something they really do love but still see what they would have done differently.”

16. Can point to a pattern of taking initiative.

As the former VP of Growth at Eventbrite (and current investor at defy.vc), it’s hardly surprising that Brian Rothenberg is focused on finding 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,” he says.

That’s why he leans on this interview question: Tell me about a time you took unexpected initiative. “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,” he says.

17. Show a need for speed.

Photo of Jaleh Rezaei
Mutiny's Jaleh Rezaei

For Mutiny’s Jaleh Rezaei, speed is king. (Her framework for revving up your marketing org is a must-read.) But it’s not a trait that leaps out from a stack of resumes. Here’s what she’s looking for when interviewing marketing managers:

  • Pose a hypothetical to source their scrappy ideas. “Ask something like: We want to get to 1,000,000 blog subscribers in 12 months. Or we want to come up with a new scalable event model that’s going to help us acquire 5,000 customers by the end of the year. How do we do that?” she says. “How scrappy are their ideas? Can they quickly put pen to paper and ideate?” she says.
  • Compress the timeframe. “If they say they want to launch a new site, I might ask, ‘How would you do that? What tools would you use to get that done in a week?’ Then I’d follow up: That’s a great suggestion, now I want you to do it in one day. How would you get this out tomorrow? I listen for their ability to prioritize and find an 80-20 way to get to the same impact.”
  • Uncover the hidden assumptions that will slow them down. What might go wrong? What must be true for this idea to work? “When they list their hypotheses I ask them how they can vet them in a few days.”

18. Are good at spotting superpowers.

“I’m looking for a candidate’s ability to identify superpowers in those around them that they want to improve upon themselves,” says Dan Slate, Director of Product Management at Wealthfront. That’s why he leans on this question: 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? “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,” says Slate.

NextRoll’s Roli Saxena takes a similar approach but flips the perspective: 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?

“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. 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,” says the former Chief Customer Officer at Brex and VP of Revenue at Clever.

19. Demonstrate a knack for finding the 10X — not 10% — improvements.

Anne Raimondi, COO at Asana

When Anne Raimondi is hiring, she zeros in on several traits, including perspective. “I spend a lot of time seeing how a candidate would approach the very real problems and challenges that the company is dealing with. Are they starting to picture themselves actually in the company and in the role?” says the newly minted COO at Asana.

The people who are genuinely interested in the role ask questions as if they're already on the team. It’s the difference between just asking more of the superficial questions from a financial investor lens — growth rate, competition threats — versus “Help me understand some of the most important customers, what do they look like?”

First Round’s very own Meka Asonye agrees. Back when he was at Stripe, hiring for the Startup & SMB sales org, he focused on folks who were already thinking like an owner. “Can they think at the CEO level, beyond just the job they’re applying for?” he says.

That’s why he leaned on this interview question: What should our team be doing differently that could yield 10x improvement? Sometimes, responses yielded true gems that were seriously considered by the team. But often candidates ran into these troubles:

  • 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 process tweaks,” 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.”
First Round partner and former Stripe sales leader Meka Asonye

If a candidate gets stuck in that latter bucket, ask these more targeted alternatives that get at a similar line of thinking:

  • 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?

20. Can tell you what you should be looking for.

During the hiring process, you’re often (understandably) focused on your own must-haves. The bullets in your JD. The must-have capabilities to add to your team. The company culture or values assessment questions you need answered.

But for the final tip, we suggest you turn the tables to ask the candidate what you should be looking for. Here’s three variations to help you refine both your own sense of what you’re seeking and your understanding of a candidate’s capabilities.

  • What’s the difference between someone who’s great in your role versus someone who’s outstanding? LendingHome co-founder Matt Humphrey looks 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.”
  • 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 Google’s Jack Krawczyk is hiring for product teams, 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’ve found that it forces the candidate to be introspective and provide examples of how they’re a student of their craft,” says the former WeWork VP.
  • If you were in my shoes, what attributes would you look for in hiring for this role? NerdWallet co-founder and CEO Tim Chen loves 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.”

Cover image by Getty Images / jayk7.