5 Interview Questions Every Startup Needs To Ask Job Candidates

The typical interview questions don’t always address qualities startups need at different stages in their growth. These can help.

5 Interview Questions Every Startup Needs To Ask Job Candidates
[Photo: Calum MacAulay via Unsplash]

I’ve been both an interviewer and an interviewee in the startup world. In my early days, I had to quickly learn how to handle multiple roles that changed pretty much daily. And while the job came with flexible hours, it took me a while to get used to late nights, missed meals, and weekend work.


That experience, among others, impacts the way I interview job candidates. The standard interview questions don’t always cut it when it comes to identifying the personalities that will thrive in a startup environment–or weeding out those that might not.

Here are some of the questions I pose to candidates and why I ask them.

1. Where Do You See The Industry Going?

When I first started, I honestly didn’t know much about the industry my company was in. Fortunately for me, the founder wasn’t concerned that I didn’t have that knowledge. It took me some time to get up to speed, but looking back, I realized how much better it would have been for me (and for the company) had I come in with a stronger base of understanding.

While that’s not to say a candidate has to be the expert on what we do, it’s true that hiring somebody who’s observant enough to spot broad trends, keen enough to learn more about how we might impact our sector, and forthright enough to continue looking at future changes could set our startup apart. That’s why I ask this question–to find out how well a job candidate already knows how they can help us grow–starting on day one.

2. Would You Rather Be Good At A Lot Of Things Or An Expert At Just One?

Some people are like Swiss army knives–always handy to have around in any situation, and adept at figuring out any problem. They’re the full-stack developers, practical for any occasion, who can see you through to a final product. They are productive, work well with others, and are ready to add to their broad base of knowledge whenever it’s necessary.

Then there are those who stay in their corner with their master’s degree and seven years of experience in machine learning. I see both types of candidates as having potential for a startup, but the company’s current stage of development is usually what determines which personality type I hire.


It’s good to know where someone stands in order to select the right type of personality for that period of time. For example, at an early stage, it’s good to have someone who’s good at a lot of things and save the real experts for when you can hire for permanent, more specialized positions.

3. What’s Your Dream Job?

Asking someone to share their “dream job” can tell you where they see themselves headed. And especially in the early stages, I understand that not many people would be likely to say our startup was their dream job–but that’s not what I’m looking for. It’s helpful to know if the person wants to be a founder themselves or whether they want to take on a leadership role later on. Your potential new hire’s best-projected future for themselves is a picture of what kind of learning experience they want and offers you a sense of their ambition level.

4. What Do You Like To Do Outside Of Work?

This question isn’t too uncommon, but it can be particularly useful for hiring managers at startups. Understanding your candidate’s interests and hobbies can help you imagine how they’ll fit into your culture. It also provides a glimpse into their personality and motivations, and can even reveal some marketable skills that a startup could leverage.

For example, I recently interviewed someone who dabbled in photography and ended up providing us with some extraordinary visuals for our marketing and social media strategies, not to mention some pretty cool artwork for our office. If I hadn’t asked this interview question, we might have never benefitted from this additional skill that our new hire saw only as a hobby.

5. Where Do You See The Company In Five Years, And What Would Help Us Get There?

While this question is similar to one an interviewer at an established company might ask, it’s critical because a lot can happen in that five-year period. In fact, just in the year that I was hired, we went from building to launching to expanding. The dramatic change can impact some potential hires enormously. They can either contribute a lot, or the rapid transformation can turn them into a deer in the headlights.

Some of the answers I’ve heard helped me determine if a person is really excited about that potential for dramatic change, or looking for a little more stability. Plus, by asking a candidate to offer some of their own ideas that could lead to the startup’s growth or future success, I can determine how well they know what we’re trying to accomplish, what their motives are in working here, and their willingness to jump in with their sleeves rolled up.


These questions have helped me find more of the right candidates because they’re better than the usual interview fodder at addressing startups’ unique working environments. They’ve also helped me understand the type of candidates we need at different times, and what sorts of personalities we’re attracting to help us. Done right, the interview process can be a revealing experience–not just for job candidates, but for startup leaders, too.

Angela Ruth is the cofounder of Palo Alto, California-based eCash, a payments company specializing in helping businesses get paid quicker. She is a member of the Young Entrepreneur Council (YEC), an invite-only organization comprised of the world’s most promising young entrepreneurs.