What to Review for Interviews for the Last 2 Hour
Here at First Round, nosotros're ever searching for advice that gets overlooked or goes unshared, hoping to find the stones that company builders don't even know to turn over.
Whether it'south through in-person events, online discussions on First Round Network (our internal Quora-fashion platform), or the articles and interviews we share hither on the Review, we're driven by an ambition to create the space founders and startup leaders demand to exchange that "trapped" knowledge.
And in those spaces, we've seen time and time once again how the conversation inevitably drifts back to a single topic. Whether it's a Fast Rail mentorship pairing, an intimate Co-Founder Forum dinner or a CTO unconference, hiring e'er seems to be elevation of heed.
There's no shortage of challenges that could benefit from a dose of exterior perspective, from finding hiring practices that scale to bringing on a new exec to nabbing a bang-up in-house recruiter. And then there's the interview.
When you lot're scaling chop-chop, moving at warp speed, and sitting on several hiring panels, interviewing tin can seem like a job you just need to get through. But it's worth pausing to remember that the decision to hire someone is an expensive and far-reaching one. And since y'all're forced to make it after spending (at most) a few hours together, maximizing what yous can learn about candidates in those precious few minutes becomes all the more crucial.
Of grade, we've shared a fair corporeality of interview best practices in the past here on the Review. (Ii item must-reads come to mind: the seven characteristics that help you hire a top performer and this roundup of interview questions previously scattered across the Review archive).
But given the high-stakes nature of every hire, interviewing chops are ever in demand of sharpening. And that means our hunt for a crazy-good interview question is never over. We're endlessly fascinated by the get-to research in everyone'due south back pocket, the kind that makes you want to steal it for your own hiring toolkit.
To that end, we've spent the past few months reaching out to some of the smartest and most thoughtful operators in our network to pose a unproblematic question: What's your favorite interview question and why?
The responses we got back were first class. What follows is an exclusive list of 40 interview questions, sent to us by the sharpest folks we've met or just outright admire. Some of the questions are (deceptively) brusque and sweet, some are probing and unexpected, others hinge on targeted follow-ups. Broken down by topic, they tackle everything from how candidates empathise the role and process feedback to their first summertime job, worst boss, and the final time they inverse their mind. Most importantly, these incredible founders and visitor builders intermission down why they lean on these questions — and what to look for in the answers you hear.
Nosotros promise this collection serves as a rich jumping off point that you tin can leverage as y'all design your ain process, whether you're edifice it from scratch or looking to give it a refresh equally you double-down on hiring. Let's go started.
Got a favorite interview question of your own? Tell the states on Twitter or share information technology here . We'll compile the best submissions and share them with Outset Round Review newsletter subscribers .
QUESTIONS TO HELP UNPACK PIVOTAL TRANSITIONS:
i. What practise you lot want to practice differently in your next role?
When he asks this question, Instacart co-founder Max Mullen ordinarily sees 2 kinds of responses — and in that location'south ane campsite that the best candidates unremarkably fall into.
"I find that the best answers highlight what they're running toward, rather than what they're running from in their current task. If they launch into what they don't like virtually their boss or current visitor, that tells you a lot. It tests whether they're a positive person and how they handle adversity," says Mullen.
"I besides can often pick up on what interests them about our company specifically, and become a sense for how much research they've done. Finally, it gets into motivations — if they bring up how they're looking for a more challenging opportunity, you can probe how they want to make an affect or the types of problems they'd love working on," he says.
2. Imagine yourself in three years. What do you promise will exist different about you then compared to now?
Julie Zhuo is a favorite of ours for a reason. The VP of Product Design at Facebook quite literally wrote the book on how offset-time managers can approach edifice out their teams. She's graced the pages of the Review earlier as well, sharing her well-honed perspective on hiring designers, and the essential (and unique) questions every managing director should ask.
"At a growing organization, hiring well is the single most important affair you lot can do," she writes in her book. "The most of import thing to retrieve near hiring is this: hiring is non a problem to be solved but an opportunity to build the future of your system."
When we followed-upwardly with Zhuo recently to find out what floats to the summit as her favorite question after hiring hundreds of candidates over the years, her response had a similar focus on the future. "Asking a candidate to describe her vision for her own growth in the next three years helps me sympathise the candidate'southward ambitions also as how goal-oriented and self-reflective she is," says Zhuo.
3. For the last few companies y'all've been at, take me through: (i) When you left, why did you get out? (two) When you joined the adjacent one, why did you cull it?
Kevin Weil likes to walk through a candidate'southward contempo career history with a unique lens. "I love this question because it helps me understand how they call up through large decisions," says the co-creator of the Libra crytpocurrency and VP of Product for Calibra at Facebook.
Weil finds he learns a lot nearly underlying motivations past unpacking why people leave and join companies. "What were they optimizing for that the career move maximized? Are they looking for safety, or are they eager to accept risks?" he says. "Are they trying to develop new skills, or perfect existing ones? Has their goal been to scale their management experience, or dive dorsum into execution to get their hands dirty?"
Weil recommends paying special attention to how candidates cobble an answer together. "It'southward interesting to see whether they weave the answer into a narrative arc or outline a serial of distinct decisions," he says. "Do they think big picture? Are they a slap-up storyteller?"
Transitions are also Co-operative CEO Alex Austin'southward favorite place to mine. "I find that it's in the infinite between jobs when people have to brand decisions entirely independently," he says. "There'due south no team fellow member they can steal credit from or that tin do work for them. It'due south the but time in their career when y'all can get incredibly deep insight into how they remember and what motivates them. And so you can evaluate their answers confronting the characteristics you believe are required to succeed against the part."
Go candidates to tell y'all about the transitions between jobs, rather than about each one. That's a better window into what they value and how they make decisions.
QUESTIONS FOR SUSSING OUT MOTIVATIONS:
4. Amongst the people you've worked with, who exercise y'all admire and why?
On its face, this question might not seem to be designed to uncover motivations. But that's exactly what Jules Walter is digging for when he asks it in interviews.
As an angel investor, product lead for Slack'southward growth and monetization team and co-founder of CodePath.org, Walter stays busy pursuing the causes he cares nearly — and he's interested in learning more most the values that bulldoze folks who want to join his team.
"I desire to uncover a candidate's values, merely I've found that request nearly that straight isn't equally effective," he says. "This question pulls out those drivers in a more subtle, even so honest way. What they admire in others tells you a lot almost what they discover of import."
You'll acquire a lot more virtually a candidate's values by request her who she admires. Information technology's a telling glimpse into the qualities she's striving to cultivate herself.
5. Tell me about a time you took unexpected initiative. Follow-upwards: Tin can you lot tell me about another?
Brian Rothenberg is something of a growth guru. Equally the erstwhile VP of Growth at Eventbrite (and current investor at defy.vc) he'southward shared the answers to the toughest growth questions and tried-and-true tactics for tailoring strategies from zero all the way to IPO.
So it comes equally no surprise that his get-to interview question helps him uncover those candidates who push button the bounds of their own personal growth. "I've found that the all-time people on your squad consistently take initiative, even when it's not expected of them," says Rothenberg. "But later on they requite one example of initiative in action, information technology's critical to follow up by asking for some other. I want to see a pattern, whether it'due south at piece of work, school, or any other place."
6. What'south something peachy about your current or previous job? Why?
bethanye McKinney Blount is a fount of company building wisdom. Beyond the class of her career, the co-founder and CEO of Compaas (and onetime engineering leader at Reddit and Facebook) has shared insights on everything from troubleshooting troublemakers in startup civilization to introducing comp transparency.
"Asking this question in interviews tells me 2 different things," says Blount. "First, I acquire what someone loves and values — what's important to them. Second, they nearly always follow up with a qualifier," she says. "They'll often say something like 'But that doesn't make up for…' and and then they're also telling me something they don't love. I find that second piece to be very instructive. It helps me understand where they feel uncomfortable, unsupported, or generally unhappy."
7. What motivates you to work?
This i comes from Varun Srinivasan, former Senior Manager of Engineer at Coinbase (where he had front-row seats to the company'south wild ascent and came through the other side with a valuable collection of lessons on scaling).
"On its face up, it's a elementary question for the interviewer to ask. Merely it requires a tremendous corporeality of thought and introspection from interviewees," says Srinivasan. "I've institute the disproportionate nature of it unlocks valuable discussion. Great candidates will be able to articulate their intrinsic motivators and reflect on why they've worked at startups before — or upack why they want to pause in. Less-than-stellar candidates won't wade into that self-inquiry. They'll provide surface level answers such as 'I like hard technology challenges.'"
Jopwell co-founder and CEO Porter Braswell opts for a similarly open-concluded question: What does success mean to you? "I find that request questions similar these makes the candidate pause and think," says Braswell. "That helps drive a more organic and free-flowing conversation where I become to know the interviewee and what drives her on a deeper level compared to going through her resume."
8. Looking dorsum on the last five years of your career, what'due south the highlight?
According to Michael Vaughan, this question is more powerful than it seems. "Information technology tells me what blazon of person they are, what matters to them and how they think," says the former COO of Venmo and current EIR at Oak HC/FT.
"For example, if they tell me about a personal accomplishment, then I know personal career development is a huge expanse of focus. If they tell me about the accomplishment of a direct report or the team, then I know they care about developing people," says Vaughan. "If they tell me nearly a visitor feat, then I know that they tie their own success to the company'due south success — which is a great mentality for weathering the early stages of a startup."
QUESTIONS ON THEIR FIT FOR THE Function:
9. What are you lot actually good at, but never want to do anymore?
Bryan Mason, Chief Business Officer at VSCO, is a fan of this question because it gets candidates to do three things:
Reflect on what they've learned well-nigh themselves.
Test their ability to speak with humility nearly being "adept" at something
Talk about stuff you may discover valuable on their resume, that they in fact no longer desire to exercise.
"It's astonishing how often people reply proverb they never want to do exactly what I'm hiring for in this part," he says.
There are incredible candidates who excel at exactly what you're hiring for. The trouble is that they don't want to do it anymore.
10. What'southward the difference between someone who'due south nifty in your role versus someone who's outstanding?
When interviewing candidates for LendingHome, co-founder and CEO Matt Humphrey is on the lookout for a keen understanding of the difference between A+ performance and what he calls "A+++".
"I always follow-up with: 'Tin you requite 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 all-time candidates can answer almost immediately, maybe even with a wry smile because they know exactly what I'thou getting at and they're proud of doing something that was truly above and beyond."
eleven. How did you prepare for this interview?
When he asks this question, Jonah Greenberger is testing for iii things: proactiveness, resourcefulness and passion.
"Those qualities are critical for almost whatsoever position," says the CEO of Bright (a First Circular-backed company). "I also similar that this multi-purpose question is and so open-concluded. It gives room for candidates to show how concise, creative, and articulate they are."
12. What exercise you believe yous can achieve with us personally or professionally that you can't anywhere else in the earth?
Shiva Rajaraman (CTO at WeWork and former VP of Product at Spotify) typically asks this question at the tail-end of an interview cycle.
"I like information technology because candidates reveal their individual motivations, creativity, and commitment to our mission all in one response," says Rajaraman. "Oftentimes, they haven't really thought about our company or capabilities deeply. The answers here can exist revealing as to whether we are truly the all-time fit. It also helps cement that we are a special identify for the person to thrive. Most importantly, if a candidate is able to articulate her ambitions and how we tin can help her achieve them, nosotros are i step closer to closing her."
Questions about why someone wants to work here and take on this detail office may seem routine, but they're incredibly important. Often, candidates are fleeing something else and haven't thought deeply about what they want next.
Equally the Corporate Communications Manager at Looker, a company that's put tremendous thought and care into bringing new people on board, Tamara Ford John similarly recommends digging into what makes candidates passionate nigh the specific opportunity in front of them. "I always enquire candidates, 'Why exercise you desire to piece of work here ? Why do you feel you lot will exist adept at this position?'" she says.
"I've found that the specifics of why someone is drawn to your visitor and believes they'll succeed in a given role are often overlooked. It'due south incredible how many times I've seen people fall down when it comes to answering these questions in interviews."
thirteen. What are the three well-nigh important characteristics of this part? How would yous stack rank yourself from strongest to least developed amidst these traits?
When Jack Krawczyk is hiring for WeWork's Product squad, he'due south 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 abound.
"I utilise this question when hiring product managers, but it can work for other functions," he says. "I've found that information technology forces the candidate to be introspective and provide examples of how they're a student of their craft."
xiv. Tell me about your platonic adjacent role. What characteristics does information technology accept from a responsibility, team, and company culture perspective? What characteristics does information technology not have?
As the head of Square'due south seller and developer business organization units, Alyssa Henry has her easily full, so the ability to quickly uncover alignment — or misalignment — in the hiring process is critical. Rather than asking direct nigh a candidate's involvement in a particular part, she's plant it helpful to abstract out to their platonic side by side office, a scenario that captures what they're really subsequently.
"This two-function question helps decide if there's a match in expectations for the office. Particularly when y'all hear the answers to what they're not looking for, sometimes you realize that the candidate is actually a better lucifer for a different role," she says. "But my favorite office is that it gives you the selling points you need to hitting on when it comes time to shut the candidate. You already know what they value, which makes it easier to tailor your pitch."
15. Information technology's September 5, 2020. What affect on the business organisation have you fabricated in the yr since y'all've joined?
When hiring for PatientPing, co-founder and CEO, Jay Desai wants to go candidates talking nearly the future, what the world will look like once they go the job, settle in and offset making an impact.
Here'southward what he'due south able to learn from this question:
Timing: "I've constitute that it provides visibility into how long the candidate thinks things should accept," says Desai. "Folks coming from larger companies assume things take longer than they should, while someone from a smaller, scrappier startup might want to become faster than they should."
Where their focus lies: "You can learn a lot from how they describe their hypothetical touch. Are they results-oriented, using numbers to depict their impact?" says Desai. "Maybe they're more process-oriented, describing their impact in terms of the systems they've successfully set up. Candidates who are more people-oriented will talk virtually how the org volition have grown and how the team will take adult."
Understanding of the role: If a candidate is manner off-base of operations from your expectations when describing what they'd hope to achieve, that'south telling in a different manner. "It tests the extent to which they take internalized this role and what the company is request them to solve for," says Desai.
The work to overcome other misunderstandings about the function and the hiring manager'due south expectations doesn't finish once a candidate officially joins the team. To continue strengthening relationships and getting to know each other, Desai relies on an incredibly tactical framework that provides a boulder for productive employee/manager relationships — read more almost information technology here .
QUESTIONS ON WORKING WITH OTHERS:
16. Tell me about a fourth dimension you strongly disagreed with your manager. What did yous do to convince him or her that you lot were right? What ultimately happened?
When nosotros surveyed our network of thoughtful founders and operators, several mentioned this as their favorite interview question. Since they each had different points of emphasis and takeaways, we've combined a few perspectives here to highlight why this question packs such a punch.
Permit's outset with Cristina Cordova. She joined Stripe equally the 28th employee and first business organization evolution hire. In addition to joining First Round's Affections Track program, she'south since led multiple teams across Business concern Development, Financial Partnerships, Partner Engineering and Variety & Inclusion functions — which ways she's done her fair share of hiring.
And this question has go her get-to in interviews for a few reasons. "It shows me how far someone will go in order to do what they believe is right," says Cordova. "The way candidates choose to unpack the anecdote also shows me how they convince others in the confront of obstacles. Do they use data? Do they gather support from others?" Asking nearly what ultimately happened is also particularly illustrative. "How they speak about not getting their way tells you lot a lot nigh whether they're willing to disagree and commit to execution," she says.
Electric current Head of People and Development at Opendoor (and former SVP of Sales at Yelp) Erica Galos Alioto leans on this question also. "I'g looking to meet how candidates deal with conflict in a work surround," she says. "Practise they openly address information technology and encounter their difference in stance equally a forcefulness? Or are they unable to see the other person's perspective? Do they endeavour to resolve it or silently let information technology bother them? This tells me a lot about their ability to communicate finer and how they volition handle disagreements with others at work."
Old Airbnb VP of Applied science Michael Curtis is also a fan of diving into how candidates handle disagreements in interviews. "I like this question for a few reasons," says Curtis. "Beginning, it's hard to give a fluff respond to. I also find it gives me bang-up bespeak on the candidate's personality in a number of dimensions, and information technology serves upwards useful data points that tin can be used in reference checks subsequently on."
Curtis probes deeper into the topic with targeted follow-ups that really become into the weeds of how the disagreement with their dominate went down:
What was your manager's reasoning?
What arguments did y'all find compelling in favor of the decision?
What was your reasoning and almost compelling arguments confronting?
Were you ultimately right?
In addition to sharing more of his go-to questions ("Recall of a fourth dimension y'all had to cut corners on a project in a fashion you weren't proud of to make a deadline. How did you handle it?"), Curtis lays out tips for focusing interviews on culture and character, equally well every bit advice for busting bureaucracy before information technology starts in this Review article.
17. Tell me about the best and worst bosses you've ever had, specifically, in your career. What was the difference?
As the CEO of Foursquare, Jeffrey Glueck finds that candidates aren't usually prepared for this question. "They often reveal what makes them tick through their answers," he says. "While the best 1 is interesting for picking up insight on how to get the well-nigh growth out of them, I often observe that the worst dominate answer is more interesting. You lot might learn that they react strongly to micromanagement, are fiercely independent, or are very individual comp focused."
The fundamental is pushing candidates to get specific. "Don't let them off with vague answers," says Glueck. "They don't have to proper name names, of course, just yous need to insist they talk about two specific bosses at specific companies, not generalizations."
xviii. What'south one role of your previous company'southward culture that yous hope to bring to your next one? What ane office practise you hope to non find?
Ben Kamens, the founder and CEO of Spring Discovery (and alum of Khan Academy and Fog Creek Software) finds this question to be an effective fashion to probe candidates' thoughtfulness when it comes to working with others, uncovering their understanding of how team dynamics and civilization intersect.
"Do they immaturely rant about the failings of past teammates? Practice they thoughtfully consider why certain issues existed, maturely discussing the tradeoffs their previous company had to brand?" he says. "Tin can they reason through why ane company or industry's bug or culture might non employ to another'due south?"
QUESTIONS ON LEARNING FROM MISTAKES:
19. When was the last time yous changed your listen near something important?
For Sarah Fetter, Managing director of East Rock Capital, this interview question is all about evolution.
"It allows you to see how — and if — the candidate'southward belief system or fix of core values has changed. How did a powerful experience or impactful person shift the candidate'south worldview?" she says. "Follow upwardly with more questions to find out what they felt before, during and after the experience of existence challenged — that will tell y'all a great deal."
20. What's the well-nigh important thing you've learned from a peer and how take you used that lesson in your day-to-day life?
This one comes from Dan Slate, Managing director of Product Direction at Wealthfront. "I'm looking for a candidate'south ability to identify superpowers in those effectually them that they want to improve upon themselves," he says.
"I like this question because it allows me to appraise their self-reflection and growth mindset. Depending on the answer they provide, it can also be a practiced window into how humble they are."
21. Tell me about a time you lot really screwed something up. How did you handle information technology and how did y'all address the mistake?
"In i barbarous swoop, this question tests for humility, self-reflection, problem-solving and communication skills," says Republic of chad Dickerson, quondam Etsy CEO turned charabanc-to-other-CEOs at Reboot.
He notes that it also provides greater insight into scope of responsibleness in prior roles. "The bigger one's scope, the bigger the mistakes and the more complex the remediation of those mistakes," says Dickerson.
22. Tell me nigh a time you made a mistake or failed at something. What did yous larn from this experience? Tin can you give me two other examples?
As an alum of Glossier, the Chan Zuckerberg Initiative and Production Chase, Corley Hughes has serious squad-building chops. When hiring, she likes to focus on how a candidate has learned from failure — but she's plant that request about information technology only once isn't enough.
"Request for three examples gives me a better sense of someone'due south deportment and natural way of working. Everyone who's adequately prepared for an interview has one rehearsed answer on learning from failure in their pocket," she says.
"The folks who can point to iii unlike times they've messed up evidence that they have a well-honed habit of looking considerately at a situation and talking openly nearly what they'd do differently. I've establish that these people tend to naturally self-course-correct, are constantly learning, and are willing to share bad news quickly, which are must-haves on my team."
When listening to the answers, she'southward specifically looking to encounter whether the candidate can:
Speak comfortably and openly about mistakes.
Reflect and apply what they learned.
Demonstrate that they don't take themselves too seriously.
Every candidate has ane canned answer on learning from failure in their pocket. The people who can signal to iii dissimilar examples are the true abiding-learners — and the folks you need on your squad.
23. When have you felt the lowest in your career? Did you realize how you felt in the moment? How did you lot respond?
Codeacademy co-founder and CEO Zach Sims (who's previously shared his fundraising wisdom on the Review) is scouting for tenacity with this question.
"We're looking for people that know that careers have lots of ups and downs," he says. "Can y'all handle those with aplomb, working through the downs with your team and the upswing that hopefully follows? Candidates that have experience with this rollercoaster can often ride out startups better than others.
QUESTIONS THAT SURFACE Self-Awareness:
24. What's one misconception your coworkers have virtually y'all?
Umbrella co-founder Sam Gerstenzang once wrote that it's not the presence of weakness, just rather a failure to recognize it that usually holds people dorsum — and accordingly, his get-to interview question centers effectually cocky-awareness.
"I've institute this question tends to open up a candidate," he tells united states of america. "By asking for a misconception rather than something coworkers only don't know about yous, the interviewer often receives a more of import and revealing truth while also understanding how the candidate relates to their co-workers."
In Gerstenzang's feel, the misconception is frequently something a candidate wishes they had more or less of, which helps understand their underlying motivations. "A less-than-bully respond ofttimes reveals an underdeveloped sense of cocky or poor advice with co-workers," he says.
Asking about misconceptions is a powerful tool. It speaks to both your conception of yourself, and your understanding of how others perceive you — both of which are critical.
25. What are you better at than about anyone else? What'south your superpower and how will you leverage that to make an impact at this visitor?
Roli Saxena has some incredibly insightful interview questions up her sleeve. The current Chief Customer Officer at Brex (and quondam VP of Acquirement at Clever) has previously spoken to the Review about how she hunts for resilience and prioritization to find candidates who are well-equipped to combat exhaustion and overwhelm.
Another one of her favorite questions similarly straddles 2 qualities. "Past request about their superpower and how that will specifically aid them in this role, you can learn a lot about candidates' self-awareness and how prepared they are," she says. "If they can tailor their response to what our team is focused on and how they tin can add value, I know they've washed the homework — both on our company, and on themselves."
Lenny Rachitsky is likewise a fan of request candidates to share their superpowers. "Equally a manager, it's important to help people flex what they're actually practiced at, instead of just trying to improve on the areas they're struggling with," he noted in his recent advice for handling performance reviews.
Here'southward what the former Airbnb product pb is specifically looking for in answers to this interview question:
Getting thoughtful and concrete. "The best candidates have the time to pause and actually call back about it," says Rachitsky. "It's a red flag for me if they jump to stock-sounding generic answers. I want them to identify something focused, not vague."
Showing humility and authenticity. "Can they honestly indicate out both good and bad? Do I feel similar they are beingness real? I'g looking for authentic insight into this person's strengths and weaknesses," he says. "Which is why I often tack on this follow-upward: 'If I were to ask your colleagues at your last job to tell me nigh you, what would I hear?' I find that it consistently gets to existent honest stuff."
Rachitsky shared his thoughts on the role of superpowers in operation reviews, emphasizing a manager's responsibility to describe their reports' strengths — and how they tin flex them further. Get his tactical advice (and incredibly helpful template) in this Review article how performance reviews can help managers uplevel from expert to kickass.
26. If I were to go and speak to people who don't think very highly of y'all, what would they say?
This question is clearly designed to probe the depths of a candidate'southward self-awareness. But Gabriel Otte is also hunting for another quality: empathy.
Self-sensation isn't but about understanding your ain shortcomings. Develop empathy for the people who dislike you lot — otherwise you'll get caught up in justifications and evasions that make it tough to truly internalize the criticism.
"When I pose this question to candidates, I'm always looking to see how much empathy they have for the people who don't like them," says Otte, the co-founder and CEO of Freenome (and a partner in First Round's Healthcare Co-op). "Do they evade or try to justify why people might not similar them? Or are they in denial and recollect no i dislikes them?"
QUESTIONS TO FIND OUT HOW THEY Respond TO FEEDBACK:
27. What's ane critical slice of feedback you've received that was really hard to hear? Why was it difficult and what did yous do with that data? What did yous learn well-nigh yourself?
As Medium'southward Head of People, Pema Lin-Moore typically asks this question in the career history portion of the interview. "Information technology gives me a glimpse into how a person responds to feedback that'south out of line with how they run across themselves or how they wish to be seen," she says. "Y'all become a sense of how self-reflective a person tin be, how resilient they are, and the type of environment they've been operating in."
Nolan Church also similarly recommends probing into how a candidate deals with difficult feedback. "I learn more most someone from this question than anything else I ask," says the Primary People Officer at Carta . "It gives me insight into an expanse for evolution, how they respond to feedback, and their level of introspection, vulnerability and humility."
In add-on to providing question #11, LendingHome co-founder and CEO Matt Humphrey submitted another excellent question that besides fits in hither, adding a slight twist: "I always say 'Nosotros'll ask about this in references, but I'd love to hear information technology from you besides: Very specifically, what's the nearly recent piece of critical feedback that you've gotten?" he says.
For him, the preface to the question is particularly fundamental. "I've institute that throwing in the 'references' comment is important considering it tends to bring out more than honest responses," says Humphrey. "I'grand literally looking for them to go into the nitty-gritty of the when and the how, not fluffy or abstruse responses. So it's helpful to have candidates know that if they lob in a softball, I may hear something different when I'm doing reference checks."
28. Detect a way to give the candidate feedback in the interview.
This i is less question, more targeted tactic, simply it's such valuable interview advice for hiring managers that we had to include it hither. It was suggested past Nicky Goulimis, co-founder and COO of Nova Credit.
"In every interview, I try to find a way to give a candidate constructive feedback and run into how they react," she says. "How we navigate tough conversations is critical for how we'll be able to work together in the future, so it's of import to test."
It's e'er unique to the candidate, and so information technology'southward hard to give one-size-fits all advice, only here are ii tactics she relies on to create an opening for a effective feedback opportunity:
Feedback on the exercise: "Our business organization interview process typically involves a have-home that we accept candidates present," says Goulimis. "Nosotros e'er applaud the candidate at the end to share our appreciation, only then everyone on the interview panel goes around sharing feedback, both positive and effective. Information technology's incredibly instructive to see a candidate internalize that feedback and respond to it in the moment."
Feedback on their potential fit: "I as well share constructive feedback when debriefing with candidates. I talk openly well-nigh what'due south really heady to me and where I still have question marks," she says. "In addition to demonstrating my commitment to transparency, information technology as well offers them an opportunity to react to or address those areas while they're notwithstanding being considered."
QUESTIONS THAT PUT PASSION Forepart AND Heart:
29. What was the last thing you nerded out on?
Shawne Ashton, VP of Growth at mindbodygreen (and old Director of Business Operations at Zola) levels this one at candidates as a final question. "It helps me go a sense of whether this person is a life-long learner, self-starter, naturally curious, and able to teach themselves new things they're interested in," she says. "By emphasizing that it doesn't demand to be piece of work related, I find that I also become to know the person a scrap more beyond their direct job experience, and it ends the interview on a fun notation."
Upstart'southward Caput of Strategy and Partner Operations Cindy Smith asks a like question, with a slight twist: Tell me nigh a topic that you've taken information technology upon yourself to learn about. "I want to hear them talk about something they've received no formal training on," says Smith. "It shows curiosity, tenacity effectually learning and it helps me gauge how a person tackle hard topics and new challenges."
30. What are some things outside of piece of work that y'all're irrationally passionate about?
While this question may seem like a standard getting-to-know-you inquiry, Laura Behrens Wu uses it every bit an opportunity to delve deeper into a candidate'due south motivations.
"I'thousand looking for people who are intrinsically motivated, and hobbies are oft an outlet for that," says the co-founder and CEO of Shippo. "Over the years, I've found that intrinsically driven individuals typically accept other passions outside of work that they pursue in an obsessive-like way. For case, if a candidate tells me they run 10 miles a day equally a hobby, that'due south a signal of a potent internal bulldoze."
31. What'south the get-go job you had, that's not on your resume, and what did you larn from that feel?
This question is one of Maryann Kongovi's favorites. "It relaxes the candidates and leads to fun conversations about summertime jobs," says the VP of Operations at Algolia. But in that location's intention behind information technology also. "I always come abroad with ameliorate insight into their values and perspectives on work itself."
QUESTIONS THAT THROW A CURVEBALL:
32. Why shouldn't nosotros hire you?
Romy Macasieb finds this question is a useful (and unexpected) tool for excavating where a candidate still has room to grow. "It goes much deeper than your standard 'What are your iii areas of comeback?' type questions," says the founding PM and current VP of Production at Walker & Company.
"I like that information technology allows interviewees to play both sides of the tabular array. They could highlight the skills they're missing or why they might not be what we're looking for past maxim something similar 'You shouldn't hire me if you lot want someone that is quant-simply,'" Macasieb says. "Only they tin can besides plow the focus to why you might not exist a fit for them. I've heard responses like 'You shouldn't rent me if yous have an open up role floor program.'"
33. What should our squad be doing differently that could yield 10x comeback?
Meka Asonye leads the Startup & SMB sales org at Stripe, a grouping that advises venture-backed companies on their commerce, monetization and expansion strategies. "I'chiliad looking for folks who have a bias for activeness and can think like an owner," he says. "Can they think at the CEO level, beyond but the job they're applying for?"
Sometimes, this question surfaces some real gems. "We're actually considering piloting one of the ideas a recent candidate mentioned. I've as well had interviews where people have mentioned things that we have seriously considered but scrapped for various reasons," says Asonye.
But when the answers are less than stellar, here'due south where candidates tend to go wrong:
Ambitions aren't lofty enough. "Ofttimes I hear ideas that are a 10% comeback, not 10X. The temptation tin be to offer non-controversial, minor tweaks to process," says Asonye.
Can't think of any suggestions. "This ane is a big red flag for me, every bit I tend to see candidates in a second or tertiary round interview, after the candidate has met with five to 10 people," says Asonye. "They should be pretty well-versed in our company and production by so, so it's often a sign that they oasis't done their homework."
To troubleshoot conversations that have stalled out, Asonye offers helpful footholds with these guiding questions:
Why might we be unable to raise our next round of financing?
Why would someone choose to work with our biggest competitor?
What product or service might we innovate that would be valuable to our core client?
34. Teach me something.
This open up-ended and surprising prompt was part of Nathalie McGrath's interview toolkit while she was the VP of People at Coinbase. "It tin tell you a great bargain about a candidate'due south thought procedure," McGrath says. "How exercise they communicate and reason through an issue? Do they start from offset principles? As an added do good, I often get a glance into something they're passionate near — plus the chance to personally learn something new."
Kevin Morrill is as well a fan of this approach in interviews — one that he's congenital on and thoroughly thought through afterward request it hundreds of times over the years. Morrill's an engineering manager at Quizlet, former CTO of Mattermark, and the creator of Buried Reads, a fascinating newsletter that'south a must-read in our inbox.(He co-authors information technology along with his wife, Danielle Morrill former CEO and co-founder at Mattermark, and current GM at GitLab).
And when we asked why he favored this approach in interviews, Morrill was at the prepare with this thorough Google Doc explanation on what he calls "the five-infinitesimal communication question."
Hither'due south how it works: Morrill asks candidates to break down a topic for him. It can be annihilation — a hobby, book, or project — but they'll but have five minutes to take him from a beginner to someone who understands what's most important about the topic. Here's a preview of what he's come to expect for in their explanations:
Empathy. As an interviewer posing this question, the cardinal is to keep your face vacant and minimize interjections. "A star candidate will selection up on this and ask if I sympathise so far," writes Morrill. "These are the aforementioned kind of people that empathize with customers and call back about it in all the work they do once we rent them."
Giving an illustration. Using a shortcut for explaining concepts is a telling indicator of a candidate's skill. "I case I heard while someone was teaching me the basics of poker was to take advantage of the fact I had played backgammon, even though I hadn't played poker. He talked most how in backgammon all the pieces on the board are exposed data that both players can see, simply in poker y'all have hidden data," writes Morril. "These types of explanations go a long way towards quickly communicating an thought with all kinds of implications very succinctly."
Taking the fourth dimension to pause. "Once the trigger-happy type candidates go going, they don't take any kind of bulleted listing or outline in their head of what they hope to get across," writes Morril. "What's most incredible about this is how accurately it predicts disorganized and non-goal directed behavior on the job."
It is amazing how many candidates won't premeditate before diving into interview questions. Those who take the time to stop, retrieve information technology through and take a few crystal articulate points are amongst the best people I've e'er worked with.
QUESTIONS THAT DIG INTO HOW THEY Think:
35. If you lot were to take over as CEO of your electric current company tomorrow, and had to increase your company's electric current charge per unit of growth, what three areas yous would invest in?
Jeanne DeWitt heads up Revenue & Growth for North America at Stripe, so naturally her favorite question has a growth bent to it. But by asking candidates to play CEO, she'due south uncovered a sharp way to assess them on a few different variables.
"I've found it gives candidates an opportunity to highlight their strengths and strategic thinking," she says. "But it also provides a take chances for them to practice empathy. If they get into how their hypothetical deportment as CEO will affect the squad, that signals a certain thoughtfulness about how their own working style impacts their peers or reports."
36. How would you lot build a production for people who are looking for an apartment?
Bangaly Kaba (VP of Product at Instacart and old head of growth at Instagram) gives candidates 45 minutes to piece of work through this i on a whiteboard. It'south part of the product sense portion of the PM interview process — and he finds that this seemingly mundane hypothetical can show to be very difficult.
Here'southward why it's 1 of his favorite questions to ask in an interview:
In that location's no one right reply. "As the interviewer I'm doubter when it comes to the exact product solution," says Kaba. "What I care about is the rigor of the candidate's arroyo, the depth of thinking and coherence of the product consequence, and the frameworks used to get there."
It's relevant to anybody. "Many product sense questions are niche and pertain to the company you lot're interviewing for, which carries bias considering there'south disproportionate information between interviewer and interviewee," he says. "Merely finding housing is a universal need."
It's hard to game. "Even if you know the question in advance I can offering new constraints or twists that are similar to on-the-fly changes that PMs face mean solar day-to-24-hour interval," says Kaba. "Information technology checks whether the interviewee tin recollect the thorough the product idea holistically."
37. What are ten means to speed upwards Domino'due south pizza delivery?
When hiring early-career PMs at Coinbase, Max Branzburg likes to throw this unexpected, pizza-chain related inquiry out there.
"There's no one right answer, but what I similar about this question is that nearly everyone has the same context beforehand," he says. "Skillful responses demonstrate an power to ask clarifying questions, structure thoughts, exist both creative and analytical, and consider technological and operational solutions. Plus, information technology's undeniably fun."
QUESTIONS THAT FLIP THE SCRIPT:
38. What can I tell yous about working here?
A few years back at our CTO Meridian, Kellan Elliott-McCrea gave an incredible talk on how Etsy grew their number of female person engineers past 500% in one year (see the Review commodity information technology inspired right here.) And then nosotros weren't surprised that his take on interviewing was similarly deep and insightful.
The former SVP of Eng at Blink Health and Etsy CTO finds that the fundamental model we utilize to interview within the tech industry is wrong. "It assumes we're panning a stream of loftier performing technical specialists for a few gems. This may have been truthful once upon a time, only it isn't the world we live in anymore," says Elliott-McCrea. "Software is a straightforward technical project, merely a difficult social, cultural and operational one."
Here's his take on what interviewers should focus on instead:
Treating the interview as a collaboration to make certain that the role is a skilful fit is the first priority. Making certain the candidate has a positive experience is the second priority. Everything else is a squeamish-to-have.
39. If you were in my shoes, what attributes would y'all look for in hiring for this function?
NerdWallet co-founder and CEO Tim Chen recently shared his takeaways from navigating the shift from starting time-time founder to seasoned exec on the Review, which surfaced some peculiarly interesting insights on hiring, including how he'south revamped his approach to interviewing execs and the surprisingly honest reason why he interviewed every single person upward until the NerdWallet team reached 200 people.
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And when we followed up with him to get his favorite interview question, he surfaced nonetheless some other intriguing tactic: request what the candidate would await 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 remember about the role in a dissimilar fashion. I've besides found that candidates tend to highlight their own strengths, then it gives you a window into who they are. You lot can also become a sense of whether they're good at breaking nebulous issues, similar hiring, into the cardinal drivers."
forty. What have I not asked y'all that I should accept?
"This question surprises almost anybody," says Liza Hausman, VP of Industry Marketing at Houzz. (And it'southward the perfect i to terminate on.)
"I like information technology considering it tells me what they think is of import nigh their skills or experience. It also lets me know if they have an interview strategy of their own, which can be useful if they're going to be edifice out a squad."
Got a favorite interview question of your own? Tell us on Twitter or share it hither . We'll compile the best submissions and share them with First Round Review newsletter subscribers .
Source: https://review.firstround.com/40-favorite-interview-questions-from-some-of-the-sharpest-folks-we-know
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