Want to Work for a Startup? 10 Questions to Ask Your Interviewer


In startups especially, job interviews are just as much for the interviewee as they are for the interviewer. Because there is often a lot at stake for a new company, it’s wise to ask where you will fit in among founders and first hires — and how you can make a direct impact on the company’s success.

That’s why I asked 10 entrepreneurs from the Young Entrepreneur Council (YEC) what questions they would pose for an interviewer at a startup. Here’s what they had to say:

1. What one thing must be done?

I would ask what one thing must be accomplished for the startup to succeed. There are two reasons to ask this: It will determine if they have a clear, focused vision, and it will give you a sense of how your job should be aligned with that goal.

2. When is your next funding round?

It’s a huge risk to begin work at a startup within months of an upcoming funding round. At that point, you’ve had very little time to influence the company’s viability, so you’d basically be left crossing your fingers and hoping that they’ve been doing well without the extra manpower, innovation, skill and insight that now makes you so in demand. Investing time and energy to build a startup is a calculated risk to begin with, but putting yourself in a position where your job security rests exclusively on the efforts of your predecessors is an even bigger gamble. Proceed — if at all — with extreme due diligence and caution. Whatever answer they give, deduct two to four months in case they’ve underestimated their expenses — it happens.

3. What’s your runway?

Startups are almost always on the verge of running out of money. They are dependent on their next funding round or their next big client. You should ask how many months of runway they have left, so you know what you’re getting into. You could be out of a job in three to six months after joining.

4. How does your product apply to my role?

Startups need people who love to explore and are curious. Do your homework before the interview by signing up for a free trail of the startup’s product. Make a list of all the different questions you have about the product based on your experience. Try to tie the best questions back to the role you’re applying for, and think of possible solutions to make the experience better. During the interview, bring up the question you had from your experience. This shows the interviewer you care, you’re analytical and will respectfully challenge the startup to be better.

5. What are your founders’ goals?

If interviewing with a founder, I’d ask what the founder hoped to gain from the venture. Do they want to create a world-famous product, take the company public or make as much money as possible? Although there isn’t necessarily a right answer, the interviewee should be looking for some consistency among the founders. In addition, the prospective employee can decide if his or her goals align with theirs.

6. What’s your exit strategy?

Candidates are often so excited about working for a hot, new startup they don’t think about their own long-term potential. Before accepting an offer with a startup, ask what their exit strategy is, and make sure you’re on board. If they’re all about acquisition, ask about time frame goals. If it’s not about exit, dig into specific growth plans for the years to come. They may not have exact answers, but you’ll get insight into how strong their vision is and how much foresight they have to consider these things.

7. What is the sales strategy?

Startups are often focused on product and user traction first, but it’s critical for the company to eventually monetize. While some startups keep operations running from proceeds of fundraising, it’s important to understand — before you join the company — how the startup intends to make money from customers or users. Having an intimate understanding of the sales strategy will help you gauge the likelihood that the company will succeed and can be your best position when you’re interviewing for a job at the firm because you’ll have a great strategic focus.

8. What’s the focus for the next three months?

This question is a shortcut way to learn about what your job experience is going to be like. For example, if the startup says it plans to launch two new tech features for its product and you’re applying to be an engineer, you’ll likely have a great first three months. You’ll know that you have the opportunity to show your skills and your contributions will be noticed. On the other hand, if you’re applying for sales, the startup’s plan to focus on product features might mean you’re selling a product that might be outdated soon.

9. What is the culture and work environment like?

Culture fit is very important at a startup for both the employer and employee. Each startup is unique, and the work environments can range from wacky to stuffy. Because you are going to be working closely with a small team for long hours, it is imperative the company fits you as much as you fit the company.

10. What is the problem you’re solving?

The most important question to ask the interviewer is about understanding the problem the company is solving. If the answer the interviewer gives doesn’t excite you and isn’t something you’d work on in your free time, then keep looking. It is crucial to find a startup that’s solving a problem you feel incredibly passionate about fixing.