So the guys at first round have engaged some of the smartest and most thoughtful operators within the network to compile an innovative and contextualised set of interview questions. There are 40 questions in total
Some of the questions are (deceptively) short and sweet, some are probing and unexpected, others hinge on targeted follow-ups. Broken down by topic, they tackle everything from how candidates understand the role and process feedback to their first summer job, worst boss, and the last time they changed their mind.

We chose 13 out of those 40. Why 13?? That’s easy. I gave the questions to the Team at WOLFE and these rated the highest as each of us felt and saw the value not only of the questions but the amazing way they were broken down to see the complexity of the questions underneath- the why, who, how..and what to look for in the answers you hear.

The original article ‘40 Favourite interview Questions from some of the sharpest folks we know’ can be found here

Q1-For the last few companies you’ve been at, take me through: (i) When you left, why did you leave? (ii) When you joined the next one, why did you choose it?

Kevin Weil likes to walk through a candidate’s recent career history with a unique lens. “I love this question because it helps me understand how they think through big decisions,” says the co-creator of the Libra cryptocurrency and VP of Product for Calibra at Facebook.

Weil finds he learns a lot about underlying motivations by unpacking why people leave and join companies. “What were they optimising for that the career move maximised? Are they looking for safety, or are they eager to take risks?” he says. “Are they trying to develop new skills, or perfect existing ones? Has their goal been to scale their management experience, or dive back into execution to get their hands dirty?”

Weil recommends paying special attention to how candidates cobble an answer together. “It’s interesting to see whether they weave the answer into a narrative arc or outline a series of distinct decisions,” he says. “Do they think big picture? Are they a great storyteller?”

Transitions are also Branch CEO Alex Austin’s favourite place to mine. “I find that it’s in the space between jobs when people have to make decisions entirely independently,” he says. “There’s no team member they can steal credit from or that can do work for them. It’s the only time in their career when you can get incredibly deep insight into how they think and what motivates them. Then you can evaluate their answers against the characteristics you believe are required to succeed against the role.”

Get candidates to tell you about the transitions between jobs, rather than about each one. That’s a better window into what they value and how they make decisions.

 Q2-Among the people you’ve worked with, who do you admire and why?

On its face, this question might not seem to be designed to uncover motivations. But that’s exactly what Jules Walter is digging for when he asks it in interviews.

Jules Walter, product lead for monetization at Slack

As an angel investor, product lead for Slack’s growth and monetization team and co-founder of, Walter stays busy pursuing the causes he cares about — and he’s interested in learning more about the values that drive folks who want to join his team.

“I want to uncover a candidate’s values, but I’ve found that asking about that directly isn’t as effective,” he says. “This question pulls out those drivers in a more subtle, yet honest way. What they admire in others tells you a lot about what they find important.”

You’ll learn a lot more about a candidate’s values by asking her who she admires. It’s a telling glimpse into the qualities she’s striving to cultivate herself.

Q3-What motivates you to work?

This one comes from Varun Srinivasan, former Senior Director of Engineer at Coinbase (where he had front-row seats to the company’s wild ascent and came through the other side with a valuable collection of lessons on scaling).

“On its face, it’s a simple question for the interviewer to ask. But it requires a tremendous amount of thought and introspection from interviewees,” says Srinivasan. “I’ve found the asymmetric nature of it unlocks valuable discussion. Great candidates will be able to articulate their intrinsic motivators and reflect on why they’ve worked at startups before — or unpack why they want to break in. Less-than-stellar candidates won’t wade into that self-inquiry. They’ll provide surface level answers such as ‘I like hard technology challenges.’”

Jopwell co-founder and CEO Porter Braswell opts for a similarly open-ended question: What does success mean to you? “I find that asking questions like these makes the candidate pause and think,” says Braswell. “That helps drive a more organic and free-flowing conversation where I get to know the interviewee and what drives her on a deeper level compared to going through her resume.”

Q4-How did you prepare for this interview?

When he asks this question, Jonah Greenberger is testing for three things: pro-activeness, resourcefulness and passion.

“Those qualities are critical for almost any position,” says the CEO of Bright (a First Round-backed company). “I also like that this multi-purpose question is so open-ended. It gives room for candidates to show how concise, creative, and clear they are.”

Q5-What do you believe you can achieve with us personally or professionally that you can’t anywhere else in the world?

Shiva Rajaraman (CTO at WeWork and former VP of Product at Spotify) typically asks this question at the tail-end of an interview cycle.

“I like it because candidates reveal their individual motivations, creativity, and commitment to our mission all in one response,” says Rajaraman. “Often, they haven’t really thought about our company or capabilities deeply. The answers here can be revealing as to whether we are truly the best fit. It also helps cement that we are a special place for the person to thrive. Most importantly, if a candidate is able to articulate her ambitions and how we can help her achieve them, we are one step closer to closing her.”

Questions about why someone wants to work here and take on this particular role may seem routine, but they’re incredibly important. Often, candidates are fleeing something else and haven’t thought deeply about what they want next.

As the Corporate Communications Manager at Looker, a company that’s put tremendous thought and care into bringing new people on boardTamara Ford John similarly recommends digging into what makes candidates passionate about the specific opportunity in front of them. “I always ask candidates, ‘Why do you want to work here? Why do you feel you will be good at this position?’” she says.

“I’ve found that the specifics of why someone is drawn to your company and believes they’ll succeed in a given role are often overlooked. It’s incredible how many times I’ve seen people fall down when it comes to answering these questions in interviews.”

Q6-Tell  me about a time you strongly disagreed with your manager. What did you do to convince him or her that you were right? What ultimately happened?

When we surveyed our network of thoughtful founders and operators, several mentioned this as their favourite 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.

Stripe’s Cristina Cordova

Let’s start with Cristina Cordova. She joined Stripe as the 28th employee and first business development hire. In addition to joining First Round’s Angel Track program, she’s since led multiple teams across Business Development, Financial Partnerships, Partner Engineering and Diversity & Inclusion functions — which means she’s done her fair share of hiring.

And this question has become her go-to in interviews for a few reasons. “It shows me how far someone will go in order to do what they believe is right,” says Cordova. “The way candidates choose to unpack the anecdote also shows me how they convince others in the face of obstacles. Do they use data? Do they gather support from others?” Asking about what ultimately happened is also particularly illustrative. “How they speak about not getting their way tells you a lot about whether they’re willing to disagree and commit to execution,” she says.

Current Head of People and Development at Opendoor (and former SVP of Sales at Yelp) Erica Galos Alioto leans on this question as well. “I’m looking to see how candidates deal with conflict in a work environment,” she says. “Do they openly address it and see their difference in opinion as a strength? Or are they unable to see the other person’s perspective? Do they try to resolve it or silently let it bother them? This tells me a lot about their ability to communicate effectively and how they will handle disagreements with others at work.”

Former Airbnb VP of Engineering Michael Curtis is also a fan of diving into how candidates handle disagreements in interviews. “I like this question for a few reasons,” says Curtis. “First, it’s hard to give a fluff answer to. I also find it gives me great signal on the candidate’s personality in a number of dimensions, and it serves up useful data points that can be used in reference checks later on.”

Curtis probes deeper into the topic with targeted follow-ups that really get into the weeds of how the disagreement with their boss went down:

  • What was your manager’s reasoning?

  • What arguments did you find compelling in favour of the decision?

  • What was your reasoning and most compelling arguments against?

  • Were you ultimately right?

In addition to sharing more of his go-to questions (“Think of a time you had to cut corners on a project in a way you weren’t proud of to make a deadline. How did you handle it?”), Curtis lays out tips for focusing interviews on culture and character, as well as advice for busting bureaucracy before it starts in this Review article.

Q7-What’s one part of your previous company’s culture that you hope to bring to your next one? What one part do you hope to not find?

Ben Kamens, the founder and CEO of Spring Discovery (and alum of Khan Academy and Fog Creek Software) finds this question to be an effective way to probe candidates’ thoughtfulness when it comes to working with others, uncovering their understanding of how team dynamics and culture intersect.

“Do they immaturely rant about the failings of past teammates? Do they thoughtfully consider why certain problems existed, maturely discussing the trade-offs their previous company had to make?” he says. “Can they reason through why one company or industry’s problems or culture might not apply to another’s?”

Q8-When was the last time you changed your mind about something important?

For Sarah Fetter, Managing Director of East Rock Capital, this interview question is all about evolution.

“It allows you to see how — and if — the candidate’s belief system or set of core values has changed. How did a powerful experience or impactful person shift the candidate’s worldview?” she says. “Follow up with more questions to find out what they felt before, during and after the experience of being challenged — that will tell you a great deal.”

Q9-Tell me about a time you really screwed something up. How did you handle it and how did you address the mistake?

“In one fell swoop, this question tests for humility, self-reflection, problem-solving and communication skills,” says Chad Dickerson, former Etsy CEO turned coach-to-other-CEOs at Reboot.

Chad Dickerson, coach at Reboot and former CEO of Etsy

He notes that it also provides greater insight into scope of responsibility in prior roles. “The bigger one’s scope, the bigger the mistakes and the more complex the remediation of those mistakes,” says Dickerson.

Q10-When have you felt the lowest in your career? Did you realise how you felt in the moment? How did you 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 you 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.

Q11-What’s one critical piece of feedback you’ve received that was really difficult to hear? Why was it difficult and what did you do with that information? What did you learn about yourself?

As Medium’s Head of People, Pema Lin-Moore typically asks this question in the career history portion of the interview. “It gives me a glimpse into how a person responds to feedback that’s out of line with how they see themselves or how they wish to be seen,” she says. “You get a sense of how self-reflective a person can 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 about someone from this question than anything else I ask,” says the Chief People Officer at Carta. “It gives me insight into an area for development, how they respond to feedback, and their level of introspection, vulnerability and humility.”

In addition to providing question #11, LendingHome co-founder and CEO Matt Humphrey submitted another excellent question that also fits in here, adding a slight twist: “I always say ‘We’ll ask about this in references, but I’d love to hear it from you as well: Very specifically, what’s the most recent piece of critical feedback that you’ve gotten?” he says.

For him, the preface to the question is particularly key. “I’ve found that throwing in the ‘references’ comment is important because it tends to bring out more honest responses,” says Humphrey. “I’m literally looking for them to get into the nitty-gritty of the when and the how, not fluffy or abstract 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.”

Q12-Why shouldn’t we 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 3 areas of improvement?’ type questions,” says the founding PM and current VP of Product at Walker & Company.

“I like that it allows interviewees to play both sides of the table. They could highlight the skills they’re missing or why they might not be what we’re looking for by saying something like ‘You shouldn’t hire me if you want someone that is quant-only,’” Macasieb says. “But they can also turn the focus to why you might not be a fit for them. I’ve heard responses like ‘You shouldn’t hire me if you have an open office floor plan.’”

Q13-Teach me something!

This open-ended and surprising prompt was part of Nathalie McGrath’s interview toolkit while she was the VP of People at Coinbase. “It can tell you a great deal about a candidate’s thought process,” McGrath says. “How do they communicate and reason through an issue? Do they start from first principles? As an added benefit, I often get a glance into something they’re passionate about — plus the chance to personally learn something new.”

Kevin Morrill is also a fan of this approach in interviews — one that he’s built on and thoroughly thought through after asking 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’s a must-read in our inbox.(He co-authors it along with his wife, Danielle Morrill former CEO and co-founder at Mattermark, and current GM at GitLab).

And when we asked why he favoured this approach in interviews, Morrill was at the ready with this thorough Google Doc explanation on what he calls “the five-minute communication question.”

Here’s how it works: Morrill asks candidates to break down a topic for him. It can be anything — a hobby, book, or project — but they’ll only 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 look for in their explanations:

  • Empathy. As an interviewer posing this question, the key is to keep your face vacant and minimise interjections. “A star candidate will pick up on this and ask if I understand so far,” writes Morrill. “These are the same kind of people that empathise with customers and think about it in all the work they do once we hire them.”

  • Giving an analogy. Using a shortcut for explaining concepts is a telling indicator of a candidate’s skill. “One example 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 about how in backgammon all the pieces on the board are exposed information that both players can see, but in poker you have hidden information,” writes Morril. “These types of explanations go a long way towards quickly communicating an idea with all kinds of implications very succinctly.”

  • Taking the time to pause. “Once the trigger-happy type candidates get going, they don’t have any kind of bulleted list 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 disorganised and non-goal directed behaviour on the job.”

It is amazing how many candidates won’t premeditate before diving into interview questions. Those who take the time to stop, think it through and have a few crystal clear points are amongst the best people I’ve ever worked with.


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