When your startup is just a few folks who can all fit around the lunch table, management chops may not be top of mind. At this stage, when it’s just the founders and a few early employees, the management structure is probably pretty flat, and folks are instead left to ship quickly and largely manage themselves.
But as the product and customer base grows, so too does your org. You start hiring en masse, and suddenly that “move fast and break things” mentality needs heaps more guidance to ensure it’s moving in the right direction. At this stage, developing a stable of highly skilled managers at the company becomes priority number one.
But spotting folks who can become high-impact leaders at your company is exceptionally challenging in an interview setting. While you can probe IC skills with a coding test or other function-specific take-home projects, unraveling all the nuances that go into managing people can be incredibly tricky — especially with just a narrow sliver of time with each candidate.
So when sitting down with management candidates, interviewers tend to resort to the same ho-hum questions that barely scratch the surface. Think, “How do you describe your management style?” or “How do you motivate your team?” Any candidate who’s put the bare minimum prep work in before interviewing will have a perfectly prepped answer at the ready for these basic questions.
You’re not looking for a mediocre manager to lead a team — you’re looking for someone exceptional. So ditch the rudimentary questions and dig deeper.
Given the high-stakes nature of every hire, we’ve found that interview chops are always in need of sharpening. We’ve published a few of these interview guides on the Review in the past (like these 40 favorite interview questions and another 40 questions specifically for candidates to ask the hiring manager) — and they’re always fan favorites.
So we put out a call to some of the sharpest folks in our network for their best interview questions for management positions and assembled their responses into a new can’t-miss guide for hiring managers. We’ve broken the list down into a few targeted categories, segmented by some of the most critical management traits. We hope at least a few of them make their way onto your own list of favorites.
Looking to quickly access all the interview questions in this guide (plus some extra bonus questions)? We’ve assembled 50 questions into a handy guide for your next interview with a managerial candidate. Download the PDF below.
QUESTIONS FOR ASSESSING LEADERSHIP STYLE
1. What are 1-2 questions you always ask your team members in one-on-one meetings, and why?
This question jumps right into tactics — how does the candidate approach these recurring touchpoints with their team members? “This helps me understand how a manager motivates and builds relationships with their team,” says Zainab Ghadiyali, former Product Lead at Airbnb. It’s easy to get into discussing deliverables or completely veer on the side of connecting at a personal level. How a manager approaches 1:1s with their teams is one of the most important factors to a successful manager/report relationship.”
2. If I asked someone on your team about your leadership style, what would they say?
This prompt (also from Ghadiyali) is a slight twist on an all-too-common question — asking the candidates to reframe their perspective and put themselves in their team’s shoes. It seems simple on its face, but as a hiring manager she finds that most of the time this tweaked framing is met with a long pause, followed by a more fruitful discussion than the more basic “How would you describe your leadership style?”
3. Tell me about a time when you delved into significant detail and got your hands dirty.
At startups, there’s no room on the team for bench players — you need someone who’s equally game to make things happen, not just delegate. This question, from Gokul Rajaram, product leader at DoorDash, asks the candidate to give examples of when they’ve done just that.
Another framing, from Shippo founder and CEO Laura Behrens Wu, is to ask the candidate about the accomplishments that they’re most proud of. “Once you have the answer, ask ‘What role did you play in this? How did you contribute?’” she suggests.
At a startup, you can’t have managers who aren’t hands-on for big milestones.
4. What ritual or practice have you found to be most effective for helping your team connect and collaborate?
Management isn’t just about delivering against team goals — it’s about fostering an environment where folks can do their best work. Liz Fosslien, Head of Storytelling for Team Anywhere at Atlassian, is looking for a strong signal that folks have an existing management playbook, with repeatable processes that they can bring to the team.
5. Why did you leave IC work?
This question, which Shopify Head of Engineering Farhan Thawar introduced us to in his guide to hiring engineering VPs, is trying to sniff out folks who went into management to “get away” from whatever functional work they were doing before — like coding.
Or try out this alternative, courtesy of Richard Cho (EVP of Talent Acquisition of Charlie Health): “Management is a choice. Why did you pick this path and what keeps you in this role?”
6. How do you balance being a manager and a coach?
“I love this one because it helps me understand how someone sees their role as a manager. Often being a manager is confused with being a coach — but a manager is responsible for certain business objectives for the company and a large part of delivering on that objective is coaching their team,” says Zainab Ghadiyali. “It is, however, different from coaching which purely focuses on facilitating the development of an individual.”
(For more of Ghadiyali’s spot-on career advice, we highly recommend checking out her article on the Review on creating a curiosity-driven career).
7. What do your direct reports like about you? What does leadership like about you?
Melissa Huang (Senior Engineering Manager at Included Health) loves this question because it allows the candidate to demonstrate self-awareness and describe what they think success looks like. “The company wants a manager who understands and executes against the business goals while helping individual team members realize their full potential.”
Another framing to try out, from Merge founder and CEO Shensi Ding, is: Why would you want to work for yourself, and why would you not want to?
8. Walk me through the most significant change you’ve made as a manager in response to feedback you’ve received about your leadership.
Russ Laraway loves this question because he’s particularly passionate about developing high-quality managers — so much so that he literally wrote the book on it, titled “When They Win, You Win.” (You can get a sneak peek at the contents of his book by checking out our Review article with Laraway and this leadership hiring rubric for assessing management candidates.)
Kristina Fahl (Managing Director of Daisy Wheel Operators) suggests asking a similar question, as well as unpacking how the candidate specifically processed that piece of feedback. “We’ve all received coaching — solicited or otherwise. A manager who is open to continuous learning will have extensive experience processing feedback, as well as methods to determine what feedback to ignore,” she says.
9. When two team members disagree, how do you help solve the disagreement?
Another question pulled from Farhan Thawar’s guide for engineering leaders, but well worth adding to your repertoire for folks across any function. Conflict is bound to come up — even on high-performing, high-functioning teams. How does the leader get involved? Do they immediately leap in and solve the problem as the executive decision-maker? Do they sit back and take a more passive approach?
10. What’s something new you’ve learned recently?
Clarissa Shen, COO of Q Bio, is looking for leaders who are lifelong learners, whether they’re C-Suite executives or first-time managers. “I’m listening for an innate sense of curiosity as well as what motivates and interests them,” she says. (She’s got tons more advice for startup managers well worth your attention in her Review guide, “Give Away Your People.”)
QUESTIONS ABOUT HOW MANAGERIAL CANDIDATES SET GOALS AND COMMUNICATE STRATEGY
11. What processes have you put in place to ensure that each person on your team has a clear idea of the team's goals and each individual's role and responsibilities?
“A key part of a manager's job is setting clear goals and making sure everyone knows who is doing what. This is much harder than it sounds!” says Liz Fosslien. You’re looking for crisp frameworks and repeatable processes for keeping the team on track — not just a loosey-goosey sense that folks will eventually figure things out.
12. Can you share the vision for your org at your last company?
This question, from Stripe’s Global Head of Partnerships Jeanne DeWitt Grosser, comes paired with an important follow-up: What did you do to connect that vision with what your team actually did day to day?
You can even widen the aperture further — Kevin Caldwell, CEO and co-founder of Ossium Health, asks candidates to sell him on the vision of their most recent company. “I want to confirm that they understand the bigger picture beyond their specific domain,” he says.
13. What dashboard do you open up every morning?
While the dashboard framing is particularly apt for marketing and sales folks, this question from Dock co-founder and CEO Alex Kracov can also be slightly tweaked for any function by asking “What are the metrics and activities you are tracking every day?” You want to hire folks who are results-driven and metrics-minded — who won’t be surprised at the end of the quarter when they did or did not meet their OKRs.
14. Let's say you have to make a challenging announcement, like sharing news of a re-org or even a layoff. How would you prepare? What would you say to your team on the day of?
Another prompt courtesy of Liz Fosslien, with this situational question she’s looking to see if folks can successfully navigate through an issue that involves extensive planning. “I’m looking for things like: Do they know how to work with the relevant stakeholders, like legal or communications? Are they anticipating and preparing for concerns that the team will likely raise? Are they able to deliver hard news in a way that preserves as much trust as possible?” she says.
15. Describe a time when you felt your team wasn’t shipping frequently enough. What did you do about it?
Setting goals is just one piece of the puzzle — keeping your team on track to hit them is another. Farhan Thawar is looking for leaders who can nudge their team to stay motivated and keep pace.
Ravi Mehta (CEO of Outpace and former CPO of Tinder) takes this one step further with one of his favorite questions: “Tell me about a time when you set a critical goal for your team and they missed it. Why did they miss the goal and what did you do next?”
Setting ambitious (perhaps a bit too ambitious) goals is part and parcel with startup growth. But missing a major milestone isn’t something to sneeze at. How did the candidate right the ship and get back on track?
16. Tell me about a time when you made a meaningful impact on revenue / market cap / cost savings.
Which bottom-line metric they have the most direct influence on will depend on the role, but Ravi Mehta is looking for a candidate with a sharp strategic outlook. “Can they help us identify, prioritize, and decide on the bets that will meaningfully grow the company?” he says.
Along similar lines, David Schubring (CIO of Global Information Technology for SiteRX) is on the lookout for management candidates who can generate their own high-impact ideas, not just carry out the executive team’s vision. His suggested question is: “Give me an example of an initiative that you innovated on your own and were able to gather momentum and excitement around it. What was the initiative, what did the execution look like and what were the results?”
And Anique Drumright, COO of Loom, is looking to see that candidates have the tools in their toolbelt to get the job done with her situational prompt: "If all of your team disappeared and you had to rely on one hard skill to grow the business, what is it and why?"
17. Tell me about a time when you had to make a strategically important decision with limited data.
At startups you’re moving at warp speed, and you need leaders who are comfortable making tough calls with imperfect information. The course ahead may not always be crystal clear, can they plot their coordinates through the fog?
You could also try Ravi Mehta’s suggested question to plop the candidate into your business: “If you were to start tomorrow, what would you prioritize in the first 30 and 90 days to maximize growth?” The candidate doesn’t have nearly enough information to make a spot-on call here, but hopefully they have decent instincts and understand enough about the business to start heading in the right direction. You’re not so much looking for the “correct” answer, but more looking to peel back the layers about the steps they take to approach solving the problem.
And Ankit Gupta (co-founder and CTO of Reverie Labs) likes to see folks get reflective with one of his favorite questions: “Share a time you made a decision that you came to regret several months later. What did you learn from that?”
QUESTIONS ABOUT MANAGING HIGH AND LOW PERFORMERS
18. Who is the worst performing person on your team and how are you working to make them better?
For any manager who’s been at it for more than just a few months, lower performers are all but an inevitability (so much so that Subscript co-founder and CEO Sidharth Kakkar doesn’t even hire anyone who hasn’t let go of someone before. “They’re not that good at hiring, they’re just delusional,” he says).
This interview question, from Alex Kracov, unpacks how they approach the problem. Do they throw up their hands and give up, or do they roll up their sleeves with coaching to try to bring the struggling employee up to snuff?
19. How do you evaluate performance on your team?
When diving into lower performance, it’s critical to understand how the management candidate assesses it in the first place. “This question digs into their methodology and process for evaluating performance – what inputs do they use and are they objective and well-balanced (both leveraging objective measures like KPIs as well as feedback from stakeholders)?” asks Melissa Tan, former GM of Self-Service and Head of Growth at Webflow. “Does their process resonate with what will be needed for the role?”
Performance management is one of the most critical aspects of any manager’s role — and one of the hardest areas to get right.
20. Can you tell me about the last time you helped a star on your team find their dream job?
But far too often, managers get bogged down in spending all of their precious calendar blocks and energy on their low performers, leaving high-potential folks to just take care of themselves. But these are the folks who could end up making meaningful change in the company someday — with the right manager to help them rocket up their impact.
“I'm looking for signs of an internal ‘talent exporter’ — someone who cultivates a strong bench of talent and then sponsors them into high-impact roles across the company,” says Amanda Schwartz Ramirez, founder of Garden Labs and author of "Thinking in Quarters," a strategy and ops-focused newsletter.
If the candidate has a compelling story in response to this question, it tells her a few things:
- They understand the importance of talent retention and performance at the company level (versus solely within their team).
- They care about their team members' career and personal goals and play an active role in helping to achieve them.
- They possess the skills required to effectively sponsor someone on their team and place them in high-impact roles.
- And bonus, they possess the confidence and foresight to build a deep bench that allows them to export versus hoard top talent.
21. When new positions have opened up on your team, did you promote from within or hire externally? What is your philosophy on this?
There’s no one correct answer here — at some points in a company and team’s growth, there will be opportunities to promote current folks on the team. At other points, it may be time to bring in an outside voice. But with this question, Melissa Tan is looking for leaders who are on the hunt for chances to support their team’s career growth — those are your talent accelerators.
22. Tell me about someone you manage who’s been really successful at your company, and what made them so successful.
Lenny Rachitsky (the creator of the hugely popular Lenny’s Newsletter and Lenny’s Podcast) uses this prompt to start unpacking what the manager values most in their directs. Is it impact? Is it deft political maneuvering across the org? Is it working long hours? Is it agreeing with what the manager wants?
23. Can you tell me about one of your direct reports’ accomplishments that you’re most proud of?
One of the trickiest parts of management is you often get a few clicks farther away from the actual functional work. You’re no longer an IC churning out code or product specs — you are coaching and supporting your team. As veteran product leader Jiaona Zhang put it on the Review:
The biggest change in moving from IC to manager is that your impact is measured through your team and not what you do yourself.
And frankly, some folks struggle with finding fulfillment in the nuances of management’s job description. This interview question, courtesy of Rachael Harnish (VP of Operations at Shogun), can help assess whether the candidate is up to the task.
QUESTIONS FOR TESTING THE CANDIDATE’S CHOPS AS A HIRING MANAGER
24. Who on your team would you be happy to work for?
This is LangChain marketing leader Brie Wolfson’s go-to question, and for good reason. “We all know the popular maxims: ‘Hire people you would work for,’ or ‘A players hire A players, and B players hire C players.’ This question gets at whether or not a leader actually lives by those principles,” she says. “If a leader hires and runs a high-performing team, and is generally humble and takes pride in making their team look good, answering this question should be easy and joyful. If not, it’s a real stumbling block.”
25. Tell me about a time when you had to hire for a challenging role.
With this question, Ravi Mehta wants to dig into both what made the role a challenge to hire for, and how the candidate addressed those challenges. “Here, I’m looking for innovative approaches to sourcing, vetting and closing candidates,” he says.
26. What are the qualities that you look for when you’re hiring and do you exude them yourself?
Coaching high performers is a massively important charge for any manager — but that starts with spotting these high-potential folks in the interview process. Merge founder Shensi Ding likes to dig into exactly which traits the manager is looking for — are they trying to make up for some of their own weaknesses? Or amplifying a team strength?
27. Walk me through your end-to-end hiring process.
Melissa Tan devotes a huge amount of time in her manager interviews to digging into the candidate’s hiring practices — after all, it’s one of the most important tasks that all startup leaders will be doing. How do they recruit and evaluate candidates — do they leverage their network? Who do they include on the interview panel? How do they utilize references? And will they be able to make adjustments based on what’s needed at your company?
28. How do you help new team members ramp-to-impact quickly?
Recruiting and hiring is just the first step — onboarding new employees is not something that a high-quality manager should be just winging. “This might seem like one of those straightforward process questions — but listen closely and you'll learn a lot,” says Amanda Schwartz Ramirez. “Do they stand up systems to make ramping new contributors easy on both the new hire and the team, or are they totally ad-hoc? Do they rely solely on HR's onboarding, or do they take ownership of the 80% that is team-specific? Do they understand the value of ramping new hires effectively? Do they care?”
29. How do you keep track of the careers of the folks you’ve worked with previously?
With this question, Farhan Thawar is wary of folks who have never participated in or built out an alumni community based on their previous experience. Great managers take pride in seeing their former reports continue to flourish, even if they’re no longer at the same company.
QUESTIONS FOR EVALUATING HOW THEY WORK WITH OTHER TEAMS
30. Can you tell me about a time when you helped guide your team into better alignment with another team?
“Here, you're looking for high ownership, skillful influence, and a strong dose of humility — quite the potent cocktail,” admits Amanda Schwartz Ramirez. “An effective manager works hard to cultivate strong working relationships laterally, understanding that a team can only go so far alone. This will be an incredible superpower to have during periods of rapid scale or change, so it's worth looking for.”
Here’s her advice for assessing a poor, okay and great response:
- A challenged response acknowledges that alignment is tricky and there's "only so much you can do" (demonstrating low ownership and influence skills).
- A "so so" response may be about how they lobbied leadership and ended up shifting the misaligned team under their management (high ownership, questionable influence and humility).
- A solid response may be a story about how they took the time to learn (high humility), or developed relationships while challenging assumptions on either team (skillful influence).
She dives more into the delicate art of being a part of a cross-functional leadership team (and why fear might be holding the team back) in this Review article.
31. Which organizations have typically been your most important partners?
Watershed Head of Product Tara Seshan devotes a large portion of her management interviews to cross-functional stakeholder relationships — because even the sharpest people managers will flounder if they can’t work well with other teams. She likes to follow up on this question by asking specifically about the steps they took to build a positive relationship.
32. Which organizations have you encountered the most friction with?
Another one from Tara Seshan, which is the counterpart to the above question. How do they tackle trickier functions that they seem at odds with? How do they manage to come to a shared set of goals or processes to drive mutual accountability and respect?
33. Tell me about a time when you influenced another team in the company that had a diametrically opposed point of view.
Effective management is about influence, whether it’s at the team level, the org level, or the company level. Ravi Mehta is looking for a management candidate with strong organizational presence and the skills to motivate folks to align and move forward in the right direction. Really dig in here — what was the situation, what was at stake, and what did the candidate in particular do to enact change?
Another tactic here from Subscript CEO Sidharth Kakkar is to have candidates make a presentation to a cross-functional panel so you can witness these skills in action. “I want to see how good they are at expressing their ideas, engaging with other ideas, and recognizing when they might be wrong,” he says.
34. When you’ve worked as part of a successful team, explain the secret sauce that helped those activities go well.
“I’m looking for self-awareness — and experience,” says Kristina Fahl. “Has this person had enough road time to understand their own leadership style and the situations where they can most easily shine?”
35. Describe a shitty system at your last company. What did you do about it?
You don’t want a leader who has a tolerance for sub-optimal systems — full stop. With this question, one last one from Farhan Thawar, you’re looking for someone with a track record of making things better across the org. That’s the type of ownership mentality that distinguishes the upper-echelon of startup leaders.