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10 common startup interview questions (and how to answer them)

Shaun Gold

Entrepreneur / Author / Speaker
Working for a startup will be an experience that will be anything but conventional. The same can be said for the interview process. By preparing yourself for the interview, you will be in a much better position to get hired.

University is coming to an end. You don’t have to go home but you can’t stay here. The time has come to get a job. But not just any job, a job at a startup. Something that offers you room to grow as well as career-defining success. After all, startups are always hiring.

But before you update your LinkedIn and head to the nearest coworking spot, you need to understand that startup interviews are difficult. They ask a variety of questions that will put your knowledge and skills to the test.

Fortunately, we have prepared the following article to help you ace that interview.

So take a deep breath, trust yourself, and get ready to dive into the interview questions.

Here we go! First interview question…

1. Why us?

Variations of this question: 

  • Why do you want to work at a startup as opposed to a much larger and established corporation?
  • How do you align with our corporate culture?
  • Why this company/vertical? What is it about this industry that makes you want to work in it?
  • What are you passionate about in regard to our offering?

Why do startups ask this?

Company culture is integral to a startup. As they have limited resources to deploy, they need to make sure that the person they hire is a fit for their culture. Early hires help shape the overall culture and direction of the company, and disproportionately so. In large corporations, if someone doesn’t fit in, that won’t have a major effect on the overall culture of the company. However, at an early-stage startup, if four people out of a team of ten are not a culture fit, it could prove disastrous as the company grows. Thus, you can expect questions about cultural fit to pop up and be a big focus in the interview. Furthermore, this question is asked to test the applicant’s motivation as well as their dedication to not only the role but the company itself. While employee churn may be expected at an established corporation, startups cannot afford to hire someone and have them leave within a month. Not only would this restart the entire process but delay the startup from hitting essential growth milestones required for capital raising etc.

How to answer.

First, you should have a general idea if the startup is the right fit for you. The unlimited vacation policy shouldn’t be the only reason you want to work at that startup. Instead, you should be excited and passionate about contributing to their product offering in that industry as well as seeing yourself grow into a position of leadership at a company whose cultural values reflect your own. Furthermore, you should have a clear understanding of the startup's mission and core values. For example, here at Prosple, our mission is to help every student get the best possible start to their career. Our six core values are judgement, impact, ownership, honesty, kindness, and courage. If you were interviewing with us, we would expect you to know our mission and values. We also want to see how you resonate with them. Why do they excite and motivate you?

“Your remote-first policy and emphasis on personal independence is great, but what really excites me is your mission and values. The job market is daunting and is something that gives anxiety to not only myself but my classmates. The fact that a company exists whose mission is to help us not just find jobs, but start actual careers is something that I feel is truly needed. I really want to play a role in helping my friends and peers in their transition from university to the workforce. The values that you exemplify also resonate with me. ‘Ownership’ and ‘impact’ in particular. I want to be in a role where I can take ownership of real problems, and know I’m doing work that is valuable and has a real impact. Ownership of decisions and actions is how I operate. I feel like Prosple’s mission and values speak to me on a deeply personal level.” 

2. What do you think of [X]? What could we be doing better?

Variations of this question:

  • How would you envision this product a year from now?
  • What features are we missing?

Why do startups ask this?

The product offerings of startup companies are user driven. Feedback is essential for new versions. The startup wants to know that you not only understand their product but may have even used it in the past. Additionally, the startup wants to understand if you are capable of not only being knowledgeable and having sound judgement but also if you can be honest and even blunt with your answers.

How to answer.

Avoid a patronising answer. In your haste to get the job offer and appear liked, you may want to claim that the product is perfect in every shape and form. Refrain from doing this as it not only shows you are unprepared but that you have no original ideas to offer. In many startup roles, the employees are the first to not only brainstorm new features and ideas but to test them out. You don’t want to be the only silent person in the room.

“The product is fine but there are many key features that I think are missing. Now, these are just my opinion as a user, but I believe that it should integrate with Snapchat as well as offer more ways to access the community of users. Google Sheets are fine but if I were hired, I would want to be the face of the brand when it comes to user feedback and community outreach.”

3. What would you do in the first 30 days on the job?

Variations of this question:

  • What changes would you implement on the first day of work?

Why do startups ask this?

Unlike more traditional roles where you may find yourself in a training program, enjoying the welcome week with the other hires, and participating in whatever fun event human resources has planned, startups expect you to hit the ground running. You should be contributing on day one. Those ideas you mention regarding the product offering? Congratulations, you are now in charge of making them a reality. As previously mentioned, startups move fast and have a timetable so they want to make sure that their hires understand what is expected of them.

Another reason for this question is that it tests the acumen of the hire. If they lack an understanding of the role, this will be evident in their answers.

How to answer.

Provide examples of what you think you would do in your role and how it would benefit the startup. Don’t be unrealistic and avoid coming off as overconfident or cocky. You should mention your willingness to go the extra mile, putting in extra effort and time so that you understand the company and the obstacles. More importantly, demonstrate that you would be open to learning whatever would give you an advantage in achieving the goals associated with your role. If you need more information, just be honest and open. State what you need, why you need it, how you would obtain it, and how it would benefit the company. Maybe you require access to user analytics to see their behaviour and click rates. Perhaps you want to use a Google survey to ask questions to further ideate your plans. Mention all of this. Startups want hires who can learn and grow with the company. It isn’t uncommon for the early-stage hire in marketing to grow into a CMO role after a long period of employment with the company.

“I would begin work on the slack integration project as soon as possible. I really think this would have a significant impact on user engagement. As of now, I believe this could be achieved within four weeks or so. I would have to conduct user research, check our data, and talk with the lead product manager to understand where it fits within the product roadmap. I am more than happy to do this. I also don't think this feature will require much in the way of resources but it could have a major impact on the company's mission. In other words, it won’t cost but it will pay.”

4. How will you manage working remotely?

Variations of this question:

  • Are you able to work in a remote setting? Have you done it before?
  • Have you worked with small teams? Are you comfortable working independently? 
  • Are you comfortable with Slack? Jira? Notion? Airtable? (mandatory tools for every remote position)

Why do startups ask this?

Working for a startup offers a great deal of independence and very little oversight. In fact, many startups are known as remote-first companies, which means remote work is the main option for the majority of employees. This is due to the fact that startups often have smaller teams and flexible work environments. If you are going to be a hire, the company needs to know that you will be able to handle the workload and responsibilities. Essentially, you will need to be your own boss, managing yourself and your deliverables. You will need to know how to work with the suite of remote tools that they provide, show up to every virtual meeting (Zoom is your friend), collaborate with the other remote members of your team, stay organized, and hit all KPIs, all while your nearest co-worker could be two time zones away.

How to answer.

If you have experience working remotely, this is the time to mention it. Be sure to mention your role, the company, your previous responsibilities, and how you added value. If you don’t have remote work experience, you can mention your personal qualities that would make you stand out. For example, perhaps you were able to work on a major paper while your roommates were partying or you were able to tune out distractions while attending a virtual lecture. Ultimately, working remotely means that you need to be reliable no matter where you are based. Startups want an employee who can focus on the task at hand and not the countless notifications that may beckon them. Show them that you can be that employee.

“During Covid, I was able to not only achieve high marks in all my classes which were remote but also ran my university social clubs completely online. I am not only familiar with Zoom and Meet for communicating, but I also have mastered many of the productivity hacks of Slack and Notion to cut out distractions and focus on the task at hand.”

5. Describe your ideal role

Why do startups ask this?

Startups are different from the classroom and different from the traditional office. In fact, they may be different from anything you have ever experienced from any of your previous work experience. Startups want to understand if you know what you really want and if it is a fit for what startup life entails. This also tests your honesty and your courage, allowing you to describe your own position without any constraints. After all, you may actually create your ideal position within the startup, which is something that never happens in a more traditional company.

How to answer.

Honestly. You don’t want to lie or come off as insincere. For example, don’t say that this position is already ideal and that you wouldn’t change a thing, because that is silly. Startups want to understand if the role offered is the right fit or if they could alter it so that it is the right fit for the right candidate. You also want to avoid being too ambitious, stating that ideally there should be a massive stipend for travel and a two-year paid sabbatical. Describe your strengths and what would make you happy to come to work every day.

“I love setting large and difficult goals and working hard to achieve them. To me, obstacles are just things to be overcome. Ideally, I want to be known as the go-to person within the company that everyone can count on for help, resources, and even mentorship. At the present moment, I know that I am not there yet. However, I am not above rolling up my sleeves and doing whatever it takes to get the job done. My ideal role (and the reason I want to work at a startup) is one where I am given responsibility and challenges where I can have a real impact. I never wanted to be a “stuck in the cubicle employee” who sticks to whatever their title says. I am a believer in my own abilities and I hope that your startup can be a believer in me.”

6. Tell me about a time you failed?

Why do startups ask this?

Are you comfortable with failure?

Startups are inherently risky. More often than not, they will fail. In fact, there is even a website dedicated to failed startups. Even successful startups have failed products (anyone remember Google Glasses?). Failure is such a common occurrence in startups that they refer to it as a “pivot.” If you are going to work and even thrive in a startup, you need to be comfortable with failure. Failure of products, features, services, and more. So startups want to know if you are capable of not only failing but if you have the courage to take ownership of this failure and move forward.

How to answer.

Whatever you do, don’t ever say you never experienced failure. Everyone has failed at some point in their lives, whether this be personal or professional. You may have failed a test, a class, a project, or even achieved a personal goal. By saying you are undefeated, it shows that you are incapable of the courage to talk about your failures, but also your inability to learn from those failures. Be honest with your failures and the lessons learned. How did those lessons inspire your future actions? What was the result? Don’t be afraid to share personal details to demonstrate what happened and how it helped you grow as a person.

“I failed European history while at university. I first thought it was because the subject matter didn’t click with me. But what I later learned was that it was my studying habits. Rather than attempting to know every piece of knowledge about a specific era, I focused on key events and figures, even learning more about them than what was covered in the class. Once I was able to adjust my studying habits, I was able to not only pass the class, but achieved higher marks across all of my classes.”

7. Tell me about the last time you disagreed with someone in a position of authority?

Variations of this question:

  • How do you handle conflict?
  • Have you ever had a conflict with a coworker and resolved it?
  • Have you disagreed with someone in your group?

Why do startups ask this?

Conformity and a herd mentality are the antithesis of what startups stand for. Startups are often made of misfits, contrarians, mavericks, oddballs, and people that just generally don’t fit the corporate mould. They aren’t looking to hire people that are happy with the status quo. On the contrary, they want people who want to break the status quo and who have a conviction behind their beliefs. They want people who can disagree with authority, even when it is uncomfortable to do so. In other words, startups want to know if you have the courage to say no when everyone around you is in a rush to say yes.

How to answer.

Once again, honesty plays a major role in your answer to this question. What was the nature of the disagreement? Was it on a personal or professional level? How was it handled? What was the result? Was there even a result? Showcase your problem-solving and relationship skills in your answer. Even if you never disagreed with someone in a position of authority, you may have been tempted to do so. Mention your experience and thoughts behind it. Don’t be afraid to mention if your disagreement was with senior authority figures and if it was contentious. Startups want to see that you’ve handled real conflict with grace, civility, and professionalism. 

“In a group project in one of my classes, our team leader wanted everyone to turn in their portions by a specific deadline. As we all had other classes and responsibilities, this clearly wasn’t possible. Rather than whisper behind his back, I approached him and told him that it wasn’t feasible as we had other responsibilities. We worked together to find a compromise and, even though we disagreed, we were able to finish the project on time and receive an A.”

8. What important truth do very few people agree with you on?

Why do startups ask this?

Peter Thiel, the serial entrepreneur, and venture capitalist, originally asked this question (what is a heretical view you have?). This is a very difficult question to answer, especially as a fresh graduate. Why? Because your degree is the result of answering questions on exams that everyone has agreed is the correct answer. Much like the earlier question about disagreeing with authority, this question tests if you are capable of independent thinking and going against the status quo. Additionally, it is also a test of your courage and character.

How to answer.

There is no easy answer to this question. Why is this the case? Because everyone is different and has different beliefs. Ultimately, you need to demonstrate the ability to provide an answer that isn’t conventional and boring while being able to genuinely think for yourself. More importantly, do you have the courage to defend your position no matter how unpopular it may be? You need to be able to not only provide a challenging viewpoint but defend and debate it with confidence. The interviewer doesn’t want some boring and safe answer that everyone can agree on. They want an answer that is truly unique and shows off your uniqueness. You aren’t a drone so here is your chance to prove it! 

“My personal view, and one which I always catch a lot of grief for, is that I believe that all recreational drugs should be legalized. The war on drugs is a waste. Just like the war on terror or the war on poverty, it can’t be won. All it has done is prop up narcostates and resulted in suffering and squandered resources. While governments pour money, men, and material into fighting an unwinnable war, alcohol and tobacco remain legal and widely available (each causing harmful effects to their users as they are extremely addictive). Meanwhile, recreational drugs such as mushrooms and marijuana, which have beneficial effects on their users, remain illegal or restricted (depending on the local laws). By legalizing recreational drugs, not only could it help many people who suffer from a variety of ailments, but it can provide legal business opportunities for aspiring entrepreneurs, increased tax revenue for governments (which also provide regulation), and reduce the amount of street crime as well as lower the prison population. It also will help the addicts themselves. Studies have shown that decriminalisation results in better outcomes for addicts via better education around dosages and health risks, better treatment, and better regulation of ingredients. I also believe that legalization will reduce the stigma surrounding addiction as it brings everything to the surface. People need to understand that drug use is often the result of personal pain and suffering. Until you can cure that, there will always be a need for drugs. It is far better to legally provide for that need.”  

9. What was the last interesting thing you learned? Explain it to me.

Variations of this question:

  • What was the last book you read? Tell me about it.
  • What was the last course you took? Tell me more.

Why do startups ask this?

More often than not, startups don’t have large training budgets or multi-month onboarding programs. If you are hired, the most you may receive is a monthly stipend for books or a knowledge-based course. You can expect little in the way of formal training. So startups want hires who are naturally curious and can often be found researching on their own, not for career progression but rather for knowledge. Startups want to know that you are capable of and willing to learn new skills while working. Self-taught and self-driven hires are better able to handle the demands of a startup rather than hires who need a formal mentor, learning structure, and required reading materials.

How to answer.

You can simply reflect on your latest learning experience. What was the latest book you read? Why did you read it? What did you learn from it? Even if the knowledge gained isn’t career-oriented, share it. In a world of memes, tweets, and short-form content, startups will be impressed that you can focus, take in information, and even use that information to better yourself and perhaps even the company.

“I read one of Seth Godin’s old books, Purple Cow. I learned that in order to be a successful and buzzworthy brand, you need to be unique. His analogy of a purple cow as something that stands out and is truly unique has helped shape not only how I market myself, but how I intend to market whatever brand or company I work with.”

10. What are your compensation expectations?

Why do startups ask this?

Startups lack many things that their corporate counterparts have. This includes a clear hierarchy, a well-defined career progression, and importantly, locked-in-stone salary brackets. Unlike many large and established companies that have fixed salaries for new hires, it isn’t uncommon for startups to have a back-and-forth discussion regarding starting salaries with their possible hires. Hence be prepared to answer this question in an interview. 

Also, keep in mind; it is no secret that startups have limited capital. In fact, some may only have enough money in the bank to remain in business for eighteen months or less (this is known as a runway). If you are looking for the biggest paycheck possible with all the benefits of a Fortune 100 company, then startups will probably pass on hiring you. More often than not, hires are often given a salary that is lower than the industry standard as well as providing equity that vests over a period of time (usually over four years). This is done to keep employees loyal and committed to the startup. While this may not be the ideal situation for fresh grads looking to enter the workforce, it does give them some leverage. It allows room to negotiate with the startup. 

How to answer.

Before accepting the interview, take some time to research the company, its industry, and how employees in similar roles at other companies are compensated. It also pays to understand the entire offer, not just the salary and benefits. Above all, don’t be afraid to provide a salary range as well as negotiate to something that not only works out for you but for the company itself. After all, you may be the key hire that allows them to grow and scale.

“My salary expectations are in the 40,000 to 60,000 range along with a fair amount of equity that comes with the role. This is lower than the industry standard and I understand you are at the early stages so I wanted to see what we could do to work together. Not only can I add value at the present moment, but I believe I could grow with the company and really deliver on the expectations of the role.”

For more on negotiating salary as a fresh grad, we have you covered.


Working for a startup will be an experience that will be anything but conventional. The same can be said for the interview process. By understanding these questions and answers as well as preparing yourself for the interview, you will be in a much better position to get hired.