interview questions

Top Interview Questions – 150+ Startups Share their Most Important Question

Top Interview Questions from Startups

You may already know that tech giants like Google and Apple have their own “outside the box” hiring process.

And a big part of that hiring process is the interview questions they ask potential hires.

The question is:

How do you know if the questions you are asking are helping you figure out whether to hire the candidate or not?

To address this problem, we asked hundreds of technology startups the following question:

If you could only ask a person one question during an interview, what question would that be?

The quality and range of responses we received was absolutely amazing.

In total, we received 194 responses. We compiled these responses to create a comprehensive list of the top startup interview questions. Then we organized the questions into categories based on the type of question asked and grouped together similar questions.

The top 5 most asked questions were:

  • Why should I hire you vs the next person (or robot) to walk through the door? (Asked 11 times)
  • Why do you want to work for _____? (Asked 9 times)
  • What gets your fired up and leaping out of bed in the morning? ( Asked 8 times)
  • What’s the job you want two jobs from now, and how does this role help you get there? (Asked 7 times)
  • What are you most proud of? (Asked 6 times)

Bonus: Download the FREE ebook with all the responses.

  • Why do you want to work for a startup when you could get a job at a larger company, make more money and have a better work/life balance?
    Asked by Soha Systems
  • What does culture mean to you?
    Asked by Choozle
  • Why do you want to work for _____?
    Asked by Bridgefy, Ambassador, ViaHero, Installments, YouMail, GitLab, Phone2Action, HelpSocial and Bizible
  • What does your ideal work day look like?
    Asked by Pay By Group
  • What environment do you thrive in the most and what drives your passion?
    Asked by Vbout
  • As you look to make your next career move, I expect you’ve spent a fair amount of time thinking about what’s important to you. I’m interested in hearing what those things are. Describe for me your perfect job, company, work environment, etc. Whatever factors are most important to you.
    Asked by Wealthminder,, and Hypr
  • What are your personal values? And if you believe that your personal values are aligned with the company’s values, please describe why.
    Asked by Verlocal
  • Let’s suppose that you found your dream job with your ideal company that pays you well and has a great career path, title, benefits and perks. You have to start in 2 days and all you have to do is tell your boss what you’d want to do at this dream job and you can have it – just like that. What would you say that you’d like to do?
    Asked by Beamm
  • Are you the type to check your inbox on vacation?
    Asked by SupportYourApp
  • If you were starting a company from scratch, what would you want your company’s culture to be?
    Asked by Paubox
  • What do you see as your biggest contribution to the world in 30 years?
    Asked by SaneBox
  • In your opinion, what is leadership?
    Asked by Unleashed
  • Are you incredibly passionate about solving the problem that we are solving. Do you dream about it? Do you spend free time on it?
    Asked by Littlstar
  • What do you want from working at Wedgies? How can we help you accomplish that in this role?
    Asked by Wedgies
  • What keeps you awake at night?
    Asked by Unmetric
  • What are you passionate about outside of work?
    Asked by BetterCompany
  • What would you fire a person for?
    Asked by SEMrush
  • What other commitments do you have in your life … i.e. other jobs, school, family, community?
    Asked by Winning Email
  • Do heroes make moments or do moments make heroes?
    Asked by ReachInfluence
  • What is your leadership style?
    Asked by Peerspace
  • Put the following 3 values in the order of priority: Freedom to create, decent salary, and company equity.
    Asked by Bizmo
  • Consider three things – Humility, Hunger and Smarts. You may relate to one or all of these. Please tell me what you are the ‘most-of’ and what you are the ‘least-of’?
    Asked by Tize
  • Fast, Good, and Cheap. Which two would you pick?
    Asked by EquityZen
  • What specifically would you contribute to Wordzen during your first week of employment?
    Asked by Wordzen
  • Pick two of our company cultural values and provide an example for each where you’ve exemplified the value, preferably from your previous employment.
    Asked by TINYpulse
  • What do you do for fun and what hobbies do you partake in when you are not at work?
    Asked by Simple Night, Readz, Genius Monkey, and Vengo
  • Identify a project or task that you would be the most proud of and would consider your most significant accomplishment in your career to date and describe the circumstances. How you got involved, your contributions and participation along with your reasoning on why this is the one you picked?
    Asked by HireIQ, and Appbase
  • Based on all the facets of our company (big data, unconscious bias, diversity, analytics, mobile apps, etc) what relevant work have you done OUTSIDE OF WORK?
    Asked by Blendoor
  • Have you ever created any side-projects or organized any community events?
    Asked by Cloudpeeps
  • Tell me about something you’ve worked on recently outside of school or your job that helped you build new skills.
    Asked by Tailwind
  • Describe the last book you read and why/why not you think I should read it as well.
    Asked by Social123, and Serps
  • What was the last book you read, and what did you learn from it?
    Asked by Company Folders
  • What did you do in college aside from going to school?
    Asked by OwnLocal
  • What’s next on your bucket list and why?
    Asked by BoatBound
  • What are the three most interesting just-for-fun projects you’ve built?
    Asked by Gigster
  • Have you ever played a team sport?
    Asked by SPLT

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  • When you look back in a year from now and I bump into you at our holiday party, how you will have known that working here was a good decision and what would you tell me?
    Asked by Spendsetter
  • If your memory was wiped and you had to read one book to regain your perspective, which would it be?
    Asked by Estate
  • If we hire you right now, what are you doing at our company tomorrow, and what will you be doing at our company one year from now?
    Asked by Rollio
  • Who is someone you aspire to be like, and why?
    Asked by LogCheck
  • What is your current life goal is and where do you want to end up?
    Asked by Hawke Media
  • What do you want to do?
    Asked by Markodojo, and Avanoo
  • What’s the job you want two jobs from now, and how does this role help you get there?
    Asked by Chewse, Aha!, SkySpecs, Seniorly, Panjo, Opiatalk, and Tome
  • What are you looking for in your next position that you don’t have where you are currently working?
    Asked by CoachMarket
  • What do you want to be known for?
    Asked by Calendly, and Indigenous
  • What gets your fired up and leaping out of bed in the morning?
    Asked by Venzee, Delivra, Razuna, SherpaDesk, Visage Payroll, Thanx, TravelTag, and Ursus
  • When was the last time you had to work hard to accomplish something seemingly insurmountable where the odds were stacked against you?
    Asked by Lingo Live
  • If you woke up tomorrow a billionaire and never had to work another day for the rest of your life, what would you do?
    Asked by BuddyTruk, Everlance, Crowdcast, and SpeakUp
  • What makes you excited to go to work, and why?
    Asked by Healey Engineering, and Snappii
  • What’s your favorite thing about marketing? And why do you love it?
    Asked by LinkCaffeine
  • What’s the ONE thing you need for your next position to be the best job experience of your life?
    Asked by Knack
  • How do you stay up to date in your skills? Give me examples.
    Asked by Mariposa Interactive
  • What is your personal mission, and how does this job description align with that mission?
    Asked by Mazlo
  • In 2026, how do you envision Personal Data Fusion making you smarter?
    Asked by ModuleQ
  • Finishing up your Junior summer, heading into your senior year, what were you thinking about plans for after graduation?
    Asked by Crayon
  • Which one of the following three things motivates you most: sense of ownership, intellectual curiosity, or collaborating with peers?
    Asked by HEDVIG
  • What do you want to be most remembered for when you move on from this role?
    Asked by Opening
  • Tell me something which you know very well and you are sure that I or most of the people here have no clue about it.
    Asked by Applozic
  • Who are you going to call to tell about our (amazing new) product, and what will you ask them?
    Asked by Woxxer
  • Where everyone sees a problem, what do you see?
    Asked by SafeBeyond
  • If you had $100,000 to build your own business, what would you do and why?
    Asked by Honey, and Help Scout
  • You earn your first 100 dollars. What would you do with the first 10% of that.
    Asked by Howler
  • If you were to build a product that addresses the problem we are trying to solve, what would it look like?
    Asked by Mathx
  • Estimate the number of cabs in NYC.
    Asked by Fractl
  • We ask candidates to write a rebuttal to an article from a major publication that relied on shoddy statistical methods to reach its conclusions.
    Asked by Baydin
  • Teach me something.
    Asked by Kahoots, and ReviewTrackers
  • Can you tell me what your understanding of what our company does?
    Asked by
  • Teach me about something you’ve mastered. I’ll give you 5 minutes to prepare, and then lets take 15 minutes and talk it through.
    Asked by Hirabl
  • If you had to automate the job for which you are applying, how would you do it?
    Asked by WriteLab
  • I would ask a real world problem question that I’m currently facing in the area of the candidates expertise, and ask them how they would solve it.
    Asked by Speechpad
  • Why would clients and prospects want to use our product/ service?
    Asked by WiO
  • Walk me through how you fold a load of laundry.
    Asked by Braidio
  • Tell them my biggest challenge as a company (for their department). Then I would just ask how they’d go about solving it if they were hired.
    Asked by Globevestor
  • We don’t ask trick questions, we ask them to work with us on a project or homework piece.
    Asked by Popular Pays
  • Tell me about some typical activities that you completed in your last job that made you feel excited, were in your flow and, afterwards, made you feel emotionally stronger?
    Asked by PreScouter
  • What important truth do very few people agree with you on?
    Asked by Startup Documents
  • If you could design a business to disrupt ours, what would that business look like?
    Asked by PivotDesk
  • What is my company doing wrong and how would you fix it?
    Asked by Tenon
  • What changes should be made to enterprise software solutions to make it a SaaS solution?
    Asked by AMODIT
  • If you were the CEO of your last company, what are 3 things you would of changed?
    Asked by iDoneThis
  • You are interviewing for job X … suppose we instead offered you job Y (unrelated to current area of proficiency), what are the first 3 things you would do to ensure your success in that role?
    Asked by Myagi
  • You’re in the airport about to board a plane to go to Singapore and you realize that you lost the contact information of the person you were going to visit and don’t have enough money to stay in a hotel or get another airplane ticket—what’s your plan?
    Asked by Renegade
  • Describe the most challenging situation you had experienced in your last job and how did you overcome it?
    Asked by Codeproof, and Peer5
  • Relate a classic novel to a contemporary social issue.
    Asked by Trendify
  • Beatles or Stones? And why?
    Asked by Lately
  • What questions do you have for me?
    Asked by
  • If I talked to your current/past manager and asked them to describe you, what would they say?
    Asked by Spotio, Social Fulcrum, and Comnio
  • How do you and know each other?
    Asked by My Digital Shield
  • Can you provide 2-3 references that we could shoot a quick email to that would be ok sharing their experiences of working with you?
    Asked by Hubstaff
  • Who are your mentors and why?
    Asked by LT & Co
  • What’s your story?
    Asked by Tattle, MetaCert, Nuvi, and UpKeep
  • Tell me where you’re from.
    Asked by Lootsie
  • Tell me about a time when you were working on a team and you disagreed with someone about how to do something. Tell me the whole story and how it was resolved.
    Asked by Binti
  • Tell me about three major life decisions that had you arrive here.
    Asked by Archively
  • Can you tell me the story of your prior success, challenges, and major responsibilities?
    Asked by Camp Nativem, and Deepsense
  • How has your birth order made you who you are?
    Asked by
  • Which superhero powers do you value most?
    Asked by Winly
  • Why should I hire you vs the next person (or robot) to walk through the door?
    Asked by AstilLink, Adchemix, Edgar, Packlane, CloserIQ, Sightly, Crewspark, Maz, Nomad, VentureFund, and Thirstie
  • What are you good at, and what do you WANT to do?
    Asked by FounderSuite, and SalesWise
  • Do you have a chip on your shoulder?
    Asked by Visibl
  • How do you get out of your confort zone in your life?
    Asked by Trackin
  • What’s the hardest thing you’ve ever done?
    Asked by Tribe
  • Tell me about one of the more challenging projects you’ve done in your career. What was the goal, and how did you achieve it?
  • What does a day at work look like where at the end you look back and I think to yourself: this is so much fun, they wouldn’t even have to pay me!
    Asked by Immediately
  • At our company, we believe we can do anything. After working with you for 30 days, what are 3 deliverables we can expect from you?
    Asked by INTURN
  • In your professional career, what is the one thing you are most proud of, and likewise, what’s the one thing you are least proud of?
    Asked by Genoo
  • What makes you lose track of time and want to work nonstop? Where do you find yourself in ‘the flow’?
    Asked by Apptentive
  • What are you most proud of?
    Asked by Jebbit, Bizyhood, Quietkit, NuoDB, ExpertKnowledge, and JotForm
  • What do you want to be the best in the world at doing, and why do you want to be known for that?
    Asked by VoiceKick, and Praxis
  • How will you contribute with your work and skills to make our company reach a specific revenue increase in 3 years?
    Asked by Shazura
  • What is the one word that best describes you?
    Asked by Unigma
  • Tell me about your most embarrassing hidden talent.
    Asked by BounceExchange
  • I would ask a candidate about their former managers’ strengths and weaknesses.
    Asked by Justworks
  • Why shouldn’t I hire you?
    Asked by Rainforest, and Ninja Outreach
  • How would you do better?
    Asked by Indepayment
  • If you wouldn’t have learned the biggest lesson you have learned last year, how different your career would be today?
    Asked by Pyrus
  • Can you please describe a situation in which you had to overcome some serious obstacles or make some considerable sacrifices to achieve your goal?
    Asked by Waggl
  • Describe a skill you had to acquire on your own in a previous job. How did you approach it?
    Asked by Zety – Your Resume Builder
  • The one single question that I keep asking to detect BS: How did you do it?
    Asked by Synthesio
  • Tell me about something you have built from scratch.
    Asked by Duubl, Red Canary, and Thimble
  • What is something that you accomplished in the last 2 years that required a high amount of grit?
    Asked by Growth Geeks
  • Tell me a time you hustled to get something of importance done. A key customer deal, a partnership, getting a feature out quicker.
    Asked by TalentIQ
  • We like to hire leaders who excel in their current role and show thought leadership outside of their role, so give me an example how you have done that in your current role/company.
    Asked by ClientSuccess
  • I’d ask them to walk me through a significant project they’ve worked on. I look for passion, great communication skills, intelligence, and raw technical ability. There’s a potential fit if they can impress me with their personal contributions and higher-level insights.
    Asked by Canviz


Thank you to everyone that helped contribute to this massive post. Please share if you think it was useful.

As a quick recap, here’s the 5 most popular questions.

  • Why should I hire you vs the next person (or robot) to walk through the door? (Asked 11 times)
  • Why do you want to work for _____? (Asked 9 times)
  • What gets your fired up and leaping out of bed in the morning? ( Asked 8 times)
  • What’s the job you want two jobs from now, and how does this role help you get there? (Asked 7 times)
  • What are you most proud of? (Asked 6 times)

And our personal favorite, asked by Lingo Live:

When was the last time you had to work hard to accomplish something seemingly insurmountable where the odds were stacked against you?

Please leave a comment below and let us know how you would answer this question: If you could only ask a person one question during an interview, what question would that be?


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startup interview questions


Sean Falconer

Sean Falconer is Founder and CTO of Proven. He is a proud Canadian and reformed academic. He is passionate about making hiring for small business simple, streamlined and frictionless.

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