Your team can make or break your startup. Seriously. This is so true that is has become a cliché.
Think about it. You’re going to be spending a lot of time together. You’re going to go through a lot of super stressful situations. You may or may not go broke at some point — together. So, when you’re forming your startup team, it’s really important to make sure you’re asking the right startup interview questions.
Sure, we all know the standards. What are your greatest weaknesses? Why do you want to work here? What was your biggest accomplishment in your last job? And a bunch of those standards made it onto this list. (After all, they’re standard for a reason.) But there are other questions you can ask applicants to your startup team that really get to the heart of who they are and why they may or may not be a good fit for your company.
And, sometimes, not having any startup interview questions at all can also be a route to take to that same destination. That’s what Arvind Raichur, CEO of MrOwl, does.
“I almost never go into an interview with a list of questions,” Arvind says. “It’s really important to be specific to the person and the situation and for the conversation to be free-flowing and organic. An interview that flows organically is better than an interview that is so strict and rigid that all you’re doing is checking boxes. Don’t just check boxes, or you could miss out on learning more at a deeper level about a potential candidate, and whether or not the person you’re talking to is the right fit for your team.”
But most of us aren’t quite as freewheeling as Arvind and would probably like at least a few questions going into a startup interview. And when you’re conducting an interview, there are usually a few different things you’re trying to figure out. Who is this person? Would they be a good fit for my company? How do they work?
With those questions in mind, I’ve broken up these 46 interview questions into five categories: personal, professional, your company, industry, and fun startup interview questions. Read them all or skip ahead to a section you’re struggling with for inspiration.
Startup interview questions that help you get to know them, personally
1. “What was a really thoughtful gift (birthday, anniversary, wedding whatever) you bought or made for someone?”
“This question typically gets them [a candidate] out of their comfort zone, because they’ve never heard of it. Typically candidates get a laugh and relate a completely unrehearsed story and you get to see what a person is all about in terms of their relationships with people, which is really what any business is all about.”
–Jim Jacobs, President, Focus Insite
2. “Tell me something you are learning right now.”
“I believe one of the most important things at a startup is having a team that loves to learn. Generally, startups are doing something that not many other companies are doing. There isn’t a playbook or a process built. The worst employees for a startup are those that come in and ask for the training manual. At a startup our job is to figure it out together, no one will spoon feed you a process. So we look for employees who love learning and weed out the ones that still think they know everything.”
–Bill Balderaz, Principal, Futurety
3. “What obstacles are you still working through?”
“’What obstacles are you still working through?’ because it allows them to tell a personal story, and I’ve found that focusing on areas of improvement tends to show a humbler, more ‘real’ side of the interviewee.”
–Anna Brockway, Co-Founder and CMO of Chairish
4. “How do you spend your time outside work?”“Everyone has hobbies, some are passionate enough about their job to pursue it as a hobby, we love those people!”
–Maxim Godin, CMO and Co-Founder, CrazyLister
5. “Tell me a joke.”
“This tells you their creativity level. It also tells you how fast they work and how many applications they’re sending out. You get answers with zero effort like ‘I’m not good at telling jokes, but I work hard.’ My favorite so far was: ‘Knock, knock. Who’s there? Hire. Hire who? Hire me!’”
–Mikhail Shvartsman, Esq., Director of Marketing, USB Memory Direct
6. “What is the best thing you have done in the last year?
“This question, my favorite to ask in interviews, opens the door for candidates to tell me a story, and to allow me to see them as a person. In a small business, team members must be well-rounded, wear many hats, and be able to overcome all kinds of challenges. If they can tell me a story about the best thing that they did, I learn about their passions and what gets them excited. Then I know if it can be applied at our company.”
– Dan Creviston, Chief Product Officer, CloudRanger
7. “Would you rather be good at a lot of things or an expert at one thing?”
“It’s important to know someone’s skill set type – do they have the concentration and dedication to perfect a task, or are they going to be more suited to a generalized role.”
–Charles Cridland, Technical Director, YourParkingSpace.co.uk
8. “Do you consider yourself a hardworking person or a smart person?”
“Does a potential hire consider himself/herself as a hardworking person or as a smart person (expressed by distribution of 10 points in between, but not equally with five for hard working and five in smart. We force them to choose). The goal of the question is for a candidate to give examples to prove the answer. It is also not a secret that we feel like a hardworking person fits a startup environment best, so the one who distributes the points in favour of this characteristic is more likely to get hired. In that sense we agree with Kevin Durant ‘Hard work beats talent when talent fails to work hard.’”
–Rune Johansen, CMO, NoMore
9. “What is your superpower?”
“There is a lot in this little question including a touch of humor and a call for creativity. What sets you apart from others? What is it that you do best? I am CEO of two fast-paced startups and we hire linchpins. I have to be able to hone in on a person’s true essence and find out what makes them indispensable. Will they run on their own without needing to be spoon fed? Will they play well with others? I usually find what I need in this question.”
–Felicite Moorman, CEO, STRATIS and Bulogics
10. “When you are online just for fun, what’s interesting to you in terms of content and sites?”
“‘When you are online just for fun, what’s interesting to you in terms of content and sites?’ I’m always curious to learn how they’re exploring the home + design category and what interests them outside of work.”
–Anna Brockway, Co-Founder and CMO of Chairish
11. “What’s your greatest weakness?”
“I don’t ask this because I actually want to know what their weakness is: I ask this because I want to know how they respond to this. If they respond with something like “I work too hard” or “I am a perfectionist” then that seems disingenuous to me. Everyone has weaknesses. I want to hear someone have the confidence and honesty to admit that they actually have real weaknesses.”
–Gil Gildner, Co-Founder, Discosloth
12. “What is the craziest thing you’ve ever done?”
“Since I’ve traveled extensively (in my former career I produced media for nonprofits all across the world) I am interested in hearing about how ambitious and daring people are. I want self-starters who aren’t timid, so I ask: What is the craziest thing you’ve ever done? The answers are almost always entertaining… Some people aren’t very crazy, and others have done things that would make your insides tingle.”
–Gil Gildner, Co-Founder, Discosloth
13. “Why do you want to come work at a startup, as opposed to an established company?”
“I love hearing the different responses, coming from people of different backgrounds and ages. It is a real eye-opener sometimes, and even though the question is somewhat cliche, I get a kick out of it.”
-John Ellis, Maple Holistics
14. “What gets you excited about the future?”
“There is of course no ‘right’ answer to this question, but it tells me a lot about the candidate. Is the candidate aware of where technology might be going? What is the candidate’s view about the future economy? What gets the candidate excited? Does the candidate have an optimistic view of the future? All of these can be answered by this question. More importantly many members of the our team (including myself) have very strong ideas about the future and how we can build a better future. So this question, though seemingly harmless, strikes at the very core of our culture.
–Marcus Harjani, Co-Founder and COO, FameMoose
15. “Is it always better to seek permission or ask forgiveness? Why?”
“The reason why I like this particular question isn’t for the answer itself, but the reasoning the person has for choosing it. Most ideal employees will act on their own initiative some of the time, but ask permission for really big things.
However, candidates often go off on extremes of either choice. Saying that won’t do anything without checking and getting permission from me (Note: I don’t have time to approve every single decision). Or conversely that they’d always ask forgiveness, which leads me to try and ask follow up questions about past examples where this happened, to help me figure out if they’re going to be more a liability than an asset.
For me personally, I’d say its better in life to ask forgiveness than seek permission in most things, except when it comes to taxes and regulation.”
–Ian Wright, Founder, Merchant Machine
16. ”Other than your family, what are you passionate about?”
‘Whether it’s their Sunday night bowling league or their sons Boy Scout group, they need to be passionate something. If the candidate is not passionate about anything, he/she will not be passionate about working for my company.”
–Gene Caballero, Co-Founder, YourGreenPal
Startup interview questions that help you get to know them, professionally
17. “If you weren’t building a product with us, what product would you build?”
“This helps me see where the passion lies and if they will have a passion for what we’re doing.”
–Martin Welker, Founder, Zenkit
18. “What’s are your favorite five apps?”
“This will show if they have an eye for great product and depending on the answer also helps show if they would be a good fit for the team.”
–Martin Welker, Founder, Zenkit
19. ”What would you have done differently in your previous (or last) role, that would have created a better positive impact for your company or better addressed a challenge that your company was facing?”
“This shows attitude, problem solving, and how candid the interviewee would be — all in a single question; and it gives the candidate the opportunity to shine and show where he can have the most impact in his new role in your organization.”
–David Radin, Founder and CEO, Confirmed
20. “If you had total freedom to design your own job here, what would that look like?”
“This questions shows what the person is most passionate about and how entrepreneurially they are able to align their interests and strengths with their understanding of what the company needs.”
–Meghan Kelleher, MKTC Consulting LLC
21. “You’ve been working on a project for a while, when your manager informs you that the project’s requirements changed suddenly. What would you do?”
“We’re looking for answers that show the person is open-minded, collaborative, considers all possible scenarios, and remains calm under pressure. If you want to keep up and thrive at a tech startup like ours, those are all traits you will need.”
–Julia Marvin, Public Relations Manager, DigaBit
22. “Do you prefer to work in a team or individually?”
“I leave this question open-ended, because it says how much of a risk-taker the candidate is. Everyone who took business 101 knows the word ‘synergy,’ so picking ‘in a team’ is a safe neutral answer. For marketing, or sales, the worst answer is ‘I could do either;’ these candidates usually require the most training. They play it too safe and ask you what to do at every corner. When someone says ‘individually’ my interest is piqued immediately. That’s a risk-takers answer; which is either great or horrible. When people are used to working individually, they’re usually multi-talented and with proper team management the synergy is still there. However, sometimes these candidates have ego issues. Finally, the candidates who write dissertations as answers are by far the worst — I’ve found that they usually have a hard time getting a message across simply and clearly.”
–Mikhail Shvartsman, Esq., Director of Marketing, USB Memory Direct
23. ”If you were to open your own business in the future, what kind of business will you open and why?”
“It’s my way of finding out if the applicant has ambition, proper planning techniques and an overall drive to work hard..”
–Ian McClarty, President, Phoenix NAP Global IT Services
24. “Can you share an example of when a superior asked you to do something you weren’t comfortable with?”
“One crucial characteristic I look for in new hires is integrity. I often ask questions such as: ‘Can you share an example of when a superior asked you to do something you weren’t comfortable with?’ or ‘Have you ever been in a situation where you put your neck on the line because you wanted to protect your team from something you knew wasn’t right?’ His or her response to those questions will show me how that individual would navigate an adverse situation.”
–Michel Feaster, CEO and Co-Founder of Usermind
25. “What company would you love to work for? Have you applied there?”
“If they have not applied, it is never a good sign.”
–Benjamin D. Silbert, Esq., VP of Sales, Bar & Club Stats
26. “What do you think your last/current manager would say are your opportunities for improvement or areas to work on?”
“This tends to get the candidate to open up about their true weaknesses and is usually very insightful. Often it’s something that you might have suspected during the interview, but sometimes something new crops up and gives you a much more complete picture of what it would be like to have this person on your team.”
–Fiona Adler, Founder, Actioned
27. “From all things you achieved in your career so far, which stands out as the most significant accomplishment?”
“As a startup and employer, the most important thing in hiring is the performance of the potential candidate. You must know who you hire and if he is able to deliver great results, as every wrong hire will have a huge impact, especially as your team is rather small in the beginning – there aren’t many others that can compensate for a bad candidate.”
–Philipp Wolf, CEO and Founder, Custify
28. ”Your supervisor and CEO tell you two different ways they’d like to approach a task – how do you solve this situation/conflict?”
“I like this question because it is such a true life startup situation with a simple answer. We get all kinds of creative answers about finishing both scenarios and pitching them Shark Tank-style and seeing what wins, but in real life taking one minute and grabbing them both together is usually the best and easiest solution. In our minds, we see the CEO as this untouchable unicorn but really in a startup world, he’s usually no more than 100 feet away at any given time. Grab them both, tell them they’ve given you different instructions, and let them work it out right in front of you.”
–Greg Kuchcik, VP of Human Resources, Zeeto
29. “How do you stay on task when you’re busy?”
“Startups are typically run on the lean side and employees have to be able (and willing!) to wear many hats that extend beyond their job description. I like to hear about the techniques that candidates use to stay strategically organized and focused in order to get the assignment completed as it gives me a better idea of how they lay out the groundwork for their daily workloads.”
–Deborah Sweeney, CEO, MyCorporation.com
30. “Tell me about a time where you did something big that wasn’t your responsibility. What motivated you to do it?”
“Roles at startups change frequently because so do the needs of the new business. Employees that are willing to take on new responsibilities and actively solve current problems thrive at startups. They do what needs to be done each day instead of relying solely on a job description.”
–Josh Braaten, CEO and Co-Founder, Brandish Insights
Do they know your company? And are they a good fit?
31. “What do you want to know about our company, our product, our culture or this role?”
“In my experience, people who are very interested in joining a company have done their homework. They typically have several detailed questions, and those questions reveal a lot of things those people find important in their job. It also demonstrates their willingness to do their research and know their prospect — in this case, the hiring manager considering offering them a position.”
–Mikko Honkanen, Co-Founder, Vainu
32. “What would discourage you from working here?”
“It’s interesting to know what candidates are worried about, what we can do to prevent them from thinking about the next job.”
–Maxim Godin, CMO and Co-Founder, CrazyLister
33. “Have you worked in a distributed team before? What challenges did you face?”
“I always ask whether a candidate has worked in distributed teams and what challenges she or he has dealt with in doing so. I ask this because remote workers are common for us and working with a distributed team has many challenges, so it’s important for me to know if and how the candidate has dealt with these obstacles in the past.”
–Marcus Harjani, Co-Founder and COO, FameMoose
34. “What aspects of your work environment did you like from your previous job? What didn’t you like?”
“Go beyond asking about their previous day-to-day and ask about how they fit at their old job. Ask ‘How did you find the dynamic at your previous environment?’ or ‘What aspects of your work environment did you like from your previous job? What didn’t you like?’ You can also ask ‘What is your ideal work environment?’ Based on their responses, you’ll be able to understand whether the candidate will be a good fit for your company. Ask about their ideal work environment. ‘In what environment are you most productive and happy?’ When they respond, watch for their reactions to see what gets them most excited.”
–Dan Sines, CEO and Co-Founder, Traitify
35. ”Walk me through what you perceive to be the typical 9 AM – 5 PM workday at our company.”
“Even though the candidate doesn’t completely know their role and responsibility, this question gives you amazing insight into how knowledgeable the candidate is on what the position entails. You can tell if they’ve had experience doing this before. You also learn about the candidates spontaneity, if they can answer this question on the spot. It is also informative if the candidate has a desire to work with other people, as they will often mention ‘collaborating with others.’”
–Stefanie Rosenfield, Co-Founder, Cleveland Marketing King
Do they know your industry?
36. “Who are our five biggest competitors?”
“This one is to check if they’ve done their homework, not only on us, but also our industry. Great answers prove that they can hit the ground running.”
–Martin Welker, Founder, Zenkit
37. “Tell me something that interests you about our industry.”
“It gives us a good indication whether the candidate spent time looking at what we do, our industry. If someone really wants the job, he will prepare accordingly and those are the people we want.”
–Maxim Godin, CMO and Co-Founder, CrazyLister
38. “Where do you see our industry going in the next few years?”
“This indicates how well that candidate has done their research, understands the context of the business, and therefore might see the potential paths to growth.”
–James Rice, Head of SEO for Picked
And, of course, the fun startup interview questions.
39. “Would you rather fight 10 duck sized bears, or a bear sized duck?”
“Whilst it sounds facetious, I find it’s a good way to gauge a candidate’s reaction to the unexpected (a key startup ability to have), as well as how they problem solve. Whether they inject humor, or take the answer seriously also tells me a lot about them and how they’ll fit into the business culture. When hiring for a startup, it’s often gut-feeling that dictates which of the similarly-qualified candidates is the best fit and I rely on this question to come to my conclusion.”
–Rob Mead, Head of Marketing, Gnatta
40. “How would you growth hack a city?”
“I took this one from Nick Soman (formerly of Gusto) and I love it! It provides us with great insight into the candidate’s mindset, we are looking for startup minded people who can think outside the box and come up with new ideas.”
–Maxim Godin, CMO and Co-Founder, CrazyLister
41. “Pretend I’ve never heard of the internet and explain how you use a website to help you pursue one of your hobbies.”
“At the end of every interview I’ve conducted I find out the candidate’s hobbies, pick one, and ask which sites they use to research, discuss, or fulfill that hobby. Then I ask them to pretend I’ve never heard of the Internet and ask them to explain how to use that site for this hobby. This tells me how they critically think. The most interesting part is the first step. Do they explain what a computer is or where to use one assuming if one hasn’t heard of the internet, one likely doesn’t have a computer? Do they ask if I have a computer and which type? Do they just skip straight to “open a web browser”? This question is my favorite interview question; it requires no experience, just critical-thinking.”
–Mikhail Shvartsman, Esq., Director of Marketing, USB Memory Direct
42. “You have to finish a job that will take you one month but you ONLY have 72 hours. You MUST convince three people to work with you. Who would you choose?”
“I love this question because it helps me to know who this person prefers to work with, that is, he prefer to be with programmers or designers better than him? Equal? Or worse? Always remember: A quality player always look for A + quality partners, while those of quality B, always look for fellow quality C! With this question and in less than three minutes you can get to know your candidate perfectly. It is the key to a successful find A players for your startup!”
–Cristian Rennella, CEO and Co-Founder, elMejorTrato.com
43. “What superpower would help this company the most?”
“By asking out-of-the-box questions you can see how quickly they think on their feet. By making it about the company, you’re getting practical answers.”
–Kevin Conner, Founder and CEO, BroadbandSearch
44. ”How would you describe the color red to a blind person?”
“When I look for a potential candidate to include in my team, I like to ask brain teaser questions. specifically ‘How would you describe the color red to a blind person?’ Based on their answers, I pick who answered smartly and was able to deliver their answers with confidence.”
–Alex Roher, Medical Director, San Diego Botox
45. ”I’m not sure if you’re the perfect fit for this role. I’m curious to hear why you think you’d be a great candidate.”
“This is a great question because it’s an objection. I want to see how they handle objections like they would from a potential client or from a co-worker with a contrarian opinion. It’s also a way for me to see if they’ve done their homework on my company and their depth of understanding for what it would take to be successful in this role.”
–Jordan Wan, Founder and CEO, CloserIQ
46. ”A hammer and a nail cost $1.10 together, and the hammer costs one dollar more than the nail. How much does the nail cost?”
“I ask this question to see how someone works through it. I don’t do it in a mean or harsh way to fluster someone, but just to get a feel for how people solve something they weren’t thinking about. It’s a very simple fifth grade math question, but on the spot, it gets very tough. Almost everyone gets it wrong, but everyone handles it differently which is what I’m looking at.”
–Greg Kuchcik, VP of Human Resources, Zeeto
Also worth a read:
- Level Up Your Interviewing Skills
- Don’t Suck As An Interviewer — Interviewer Tips and Tricks
- The Deal With Team Diversity: Building a Diverse Team
- Managing Insane Growth: Master class by Matt Mullenweg
- Team & Culture: Master class by Dave Kashen
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