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20 Underrated Qualities to Look for in Candidates And 50+ Questions to Surface Them
Most teams say they want “high performers,” “mission-aligned operators,” and “team players.” Useful, but vague. In a market where hiring is hyper-competitive and interview volume is high, those labels aren’t enough to separate good from exceptional.
There’s a deeper layer of traits that actually determine how someone will operate inside a fast-moving company: how they adapt, how they learn, how they think about others, how they handle mess, how they respond when things break.
This piece pulls together 20 underrated qualities and the specific interview questions that reliably bring them to the surface. Use it to sharpen your hiring lens, build stronger scorecards, and stop defaulting to generic labels.
TO SEE HOW A CANDIDATE LEADS, FIGURE OUT IF THEY…
1. Embrace change and learn quickly
Adaptability isn’t “nice to have” anymore; it’s baseline. Roles, priorities, and environments shift constantly. The people who thrive are the ones who treat learning as part of the job, not as an extracurricular.
Anne Dwane (Village Global, ex-Chegg) looks for adaptable learners and bakes that into how she hires.
Questions:
What have you started?
How would you describe yourself in your own words?
How would a colleague describe you in three adjectives?
What trends are you seeing in your profession?
What new things have you tried recently?
Follow up on the last two: what did they try, why did it interest them, what changed as a result?
Engineering leader Marco Rogers adds another angle: how people respond when teams and processes evolve.
Questions:
Have you been part of a team that had to change how it worked as it grew? What changed and how did you react?
When processes or structures shift, where do you look for your own growth in that change?
You’re looking for people who expect change and look for upside in it, rather than people who treat change as an inconvenience.
2. Can get people to open up remotely
For leadership roles, it’s not enough to “manage” remotely; they need to create trust, momentum, and honest dialogue through a screen.
Maggie Leung, who scaled NerdWallet’s fully remote content org, focuses on how leaders create space for real conversation and alignment at a distance.
Questions:
Tell me about a time you led a distributed or partially remote team. What did you do to build trust?
How do you structure 1:1s and team meetings so people feel safe raising concerns or uncertainty?
Describe a time you had to get buy-in remotely from multiple stakeholders. How did you approach it?
When a team member is disengaged or anxious and you’re not in the same room, how do you spot it and what do you do?
You’re trying to see if they think about emotion and communication as part of the job, not as an afterthought.
3. Care about empathy, not just talk about it
Every company claims to value empathy. The real question is whether the candidate sees it as a core responsibility of leadership.
Mark Frein (ex–Lambda School, InVision, Return Path) focuses on whether someone is willing to engage at an emotional level, not just describe events.
Questions:
Tell me about a time something at work didn’t go your way. What happened? How did it make you feel?
What did you do with that experience?
People who cannot describe how something felt, or who deflect away from emotion entirely, are unlikely to create empathetic environments for others.
4. Share real failures, not polished “learning moments”
Most candidates have one rehearsed “failure story.” You want the unvarnished ones.
Corley Hughes (CFO at SonderMind) gets past the canned answer by demanding more than one example.
Questions:
Tell me about a time you made a mistake or failed. What did you learn?
Give me two other examples of times you messed up and what you took away from them.
Three real examples reveal whether someone has a habit of honest self-assessment and course correction.
Marco Zappacosta (Thumbtack) pairs pride and regret in sequence:
Questions:
What professional achievement are you most proud of? Walk me through it in detail: your role, your unique contribution, what made it matter.
What’s your biggest professional regret?
If the “regret” answer is just another brag in disguise, that’s a signal: low self-awareness or low willingness to own mistakes.
5. Keep DEI top of mind in their actual work
Diversity, equity, and inclusion aren’t just company-level statements. Strong candidates can describe how they practice inclusion themselves.
Aubrey Blanche (Culture Amp) uses questions that bring DEI from theory into everyday behavior.
Questions:
How do you personally learn how to be more inclusive? Give an example of how those learnings changed the way you work.
How do you ensure your team isn’t just building for people like themselves?
Sally Carson (ex–Duo Security) looks for depth, not buzzwords: does the candidate have a mature perspective, or are they clearly thinking about this for the first time in the interview?
6. Sell the team, not just themselves
Humility is not about being small; it’s about being accurate and team-oriented.
Adam Grant cites one telling question from Butler basketball:
Question:
Would you rather your team win and you score 5 points, or your team lose and you score 20?
Two more that reveal real humility:
Who do you owe your success to?
Who have you learned the most from, and why?
Look for candidates who credit peers, reports, and unlikely sources, not just senior people.
Jim Patterson (ex-Yammer, Eaze) flags language as a tell: people who say “I” constantly in multi-stakeholder work are usually exaggerating their role. The best people talk about “we,” “my team,” and “us” when they describe wins.
TO SEE HOW A CANDIDATE WILL EXECUTE, FIGURE OUT IF THEY…
7. Improve processes and remove friction
Good leaders don’t just accept processes; they tune them.
Shopify VP of Engineering Farhan Thawar looks for candidates who have strong opinions about process and know how to experiment with it.
Questions:
Describe the development (or team) process at your last company. What would you absolutely use again and why? What would you avoid and why?
What have you changed your mind about when it comes to process or team practices?
Tell me about a system or process that was broken. What did you do about it?
On a larger team, how do you figure out what’s working and what isn’t?
You’re looking for people who reduce administrative pain and policy-driven dissatisfaction rather than add to it.
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That’s the idea behind our latest guide: The 5 Traits AI Can’t Replace & Why They Matter More Than Ever. A fast, actionable read for business operators who want to scale with clarity — not just speed.
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8. Challenge defaults and improve their environment
Adam Grant calls these people “originals” – the ones who question bad patterns without burning everything down.
Questions:
How would you improve our interview process?
Tell me about a rule at a previous company that didn’t make sense. What did you do, and what was the outcome?
You want candidates who investigate context, talk to stakeholders, and propose improvements, not people who quietly accept nonsense or blow up over it without trying to change it.
9. Know how to introduce change, not just operate within it
It’s one thing to follow a good process; it’s another to introduce structure into a company that doesn’t have it.
Nikhyl Singhal (Meta, ex–Credit Karma) looks for people who can design and roll out process in scaling environments.
Questions:
Tell me about a time a new process was introduced on your team. What changed and how did it go?
What did you learn from that change?
Can you walk me through something you’ve iterated on repeatedly until it worked?
Good answers sound like: “Here’s how we used to do it, here’s what we tried, here’s what failed, and here’s how we adjusted.” You want iteration, not one-off “big ideas.”
10. Focus on outcomes, not just shipping
Shipping is necessary, but not sufficient. Tyler Hogge (ex–Wealthfront, Divvy) hires PMs around business impact, not feature count.
Questions:
What achievements or outcomes are you most proud of?
What did those results lead to (revenue, adoption, retention, margin, etc.)?
How did those outcomes compare to what you said they would do? What was your original target?
Great candidates give numbers and context: “We aimed for 50% adoption by year-end; we hit 65%.” They can do this repeatedly across multiple projects.
11. Help you avoid bureaucracy
Michael Curtis (AltaVista, Yahoo, Facebook, Airbnb) points out that your hiring decisions are your best defense against future bureaucracy.
He looks for people energized by solving problems, not assigning blame.
Questions:
Describe a time you strongly disagreed with management. What happened?
Tell me about a time you had to cut corners to hit a deadline and you weren’t proud of it. How did you handle that?
You’re watching reactions: do they blame “the company” and “other people,” or do they show empathy for other perspectives and talk about how they worked toward a solution?
Adam Grant adds:
Question:
In which job were you most miserable? Why, and how did you handle it?
Look for people who responded to broken systems by trying to improve them, not by disengaging and complaining.
TO SEE WHAT A CANDIDATE CARES ABOUT, FIGURE OUT IF THEY…
12. Apply a long-term lens
Todd Jackson (Google, Facebook, Twitter, Dropbox, now First Round) uses an old question with a tighter filter:
Question:
Why do you want to work at this company or on this product?
Weak answers: “The space is hot,” “Everyone’s talking about it.”
Strong answers are specific and long-term:
“I’ve been interested in this space for years and did X and Y to prepare for this shift.”
“This company has an advantage because of Y, and here’s how I’d build on it.”
“I’ve used this product for a while; I love feature A, and I think improving B would move metric C for reason D.”
You want people excited about the category and problem space, not just this one job posting.
13. Are fueled by curiosity
Instagram cofounder Mike Krieger looked for “I’ll learn anything to make this happen” generalists.
He listens for curiosity that manifests in self-driven projects, not just tooling familiarity.
Questions:
What side projects are you excited about?
Tell me about a time you went down a rabbit hole on something recently. What triggered it and what did you learn?
You want eyes lighting up and detailed explanations, not generic “I like to learn new things.”
Looker founder Lloyd Tabb uses a simple diagnostic:
Question:
Tell me about a day at work in the last year that was truly great. What happened?
The answer reveals what energizes them and what motivates their best work, independent of tech stacks or company logos.
14. Are clear about what they don’t want to do
Bryan Mason (VSCO, True Networks) always asks:
Question:
What are you really good at that you never want to do again?
This surfaces three things at once: self-knowledge, humility, and landmines. Many people are excellent at something they’re actively trying to leave behind. If that’s the core of your role, you have a mismatch.
Todd Jackson uses a similar version for PMs:
Question:
What aspect of product management do you find least interesting?
Weak answers: complaining about “grunt work” as beneath them. Good answers: acknowledging the unglamorous parts as necessary and part of supporting the team.
TO SEE WHETHER THEY HAVE STANDOUT HABITS, FIGURE OUT IF THEY…
15. Exhibit real thoughtfulness
Julie Zhuo (Sundial, ex–Facebook) defines great designers as people whose decisions are intentional, not arbitrary.
Her questions work well beyond design.
Questions:
Think about a long-term project you worked on. If you’d had two more months, what would you have done differently?
Pick a product you love. Why do you think it was designed the way it was? What would you have done differently?
Thoughtful candidates have specific, considered answers, not “it was perfect as is” or trivial cosmetic tweaks.
16. Show a pattern of taking initiative
Brian Rothenberg (ex–Eventbrite, now investor) wants people who move without being asked.
Question:
Tell me about a time you took unexpected initiative.
Then he always asks for another example. The pattern is the point. You’re looking for repeated behavior across different contexts, not a one-time story.
17. Have a bias for speed and iteration
Jaleh Rezaei (Mutiny) hires marketers with a strong execution bias.
She uses hypotheticals to reveal execution instincts:
Questions:
We want to reach 1,000,000 blog subscribers in 12 months. What would you do?
How would you launch [X initiative] in a week? What if you only had one day?
What must be true for your idea to work? How could you test those assumptions in a few days?
You’re looking for prioritization, creative shortcuts, and fast learning loops, not perfectly polished plans that require six months and five new headcount.
18. Are good at spotting and learning from others’ superpowers
Dan Slate (Wealthfront) looks for people who notice and borrow from others’ strengths.
Question:
What’s the most important thing you’ve learned from a peer, and how have you used that lesson?
Roli Saxena (NextRoll, ex-Brex) flips it:
Question:
What are you better at than most people? What’s your superpower, and how would you use it here?
You want candidates who are both self-aware and able to connect their strengths to your context.
19. Think in 10x, not 10%
Asana COO Anne Raimondi and First Round partner (and former Stripe sales leader) Meka Asonye both look for people who think like owners.
Asonye’s favorite question:
Question:
What should our team be doing differently that could yield a 10x improvement?
Candidates who can’t think of anything, or only suggest minor tweaks, usually haven’t done the work to understand your product and business.
If they get stuck, you can narrow it:
Why might we struggle to raise our next round?
Why would someone pick our biggest competitor over us?
What new product or service could we launch that would be especially valuable to our core customer?
You’re looking for structured thinking about leverage, not generic criticism.
20. Can tell you what you should be looking for
Strong candidates understand their craft well enough to define excellence in it.
Three ways to flip the script:
From Matt Humphrey (LendingHome):
What’s the difference between someone who is great in this role and someone who’s outstanding?
Can you give specific examples from your own experience?
You’re testing whether they know what “A+++” actually looks like.
From Jack Krawczyk (Google, ex-WeWork):
What are the three most important characteristics in this function? How would you stack rank yourself on those, from strongest to least developed?
You learn how they think about the role and how honest they are about their own gaps.
From Tim Chen (NerdWallet):
If you were in my shoes, what attributes would you look for when hiring for this role?
Candidates usually emphasize their own strengths, which gives you another lens on how they see themselves and the role.
Used properly, these traits and questions move you out of “vibe-based hiring” and into something more predictable: structured judgment about how someone will actually operate when things are ambiguous, pressured, political, fast, or broken.
You don’t need to use all 50+ questions. Pick the 5–10 traits that matter most for your stage and culture, wire them into your scorecards, and standardize how you evaluate them. That’s how you stop hiring by gut and start hiring on signal.
