11 Offbeat And Revealing Interview Questions

Struggling to find the right candidates for your high-intensity startup? You might not be asking them what you really need to know.

11 Offbeat And Revealing Interview Questions
[Photo: Flickr user Neil Conway]

Working for an early-stage startup can be hard. New companies need teams that are agile and active, resilient in the face of setbacks, and cool under pressure. Startup employees wear many hats and need to be dynamic enough to fit wherever they’re needed. At the same time, they need to be fearless and opinionated, capable of working on a small team while willing to challenge the status quo.


Needless to say, it isn’t easy to hire people who fit that bill. Not only are the right candidates hard to find, the standard interview questions aren’t very effective at helping you find them. These 11 questions can help you dig deeper to see whether a candidate is the right fit for a fast-paced startup environment where culture is so crucial. Of course, they might not be as applicable everywhere, so adjust your questions or look for different answers depending on your own work culture.

1. What Did You Like And Dislike About Your Latest Boss?

I prefer to open with a question that forces the candidate to be thoughtful and opinionated. I’m not looking for them to slander their last or current employer, but I want to find out what the candidate values in a work culture. If the candidate complains about his or her supervisor’s micromanaging, for instance, that sends up a red flag for me. In my experience, micromanaging usually happens when employees require it. Startups are intimate environments, but that’s all the more reason I need to trust my team’s autonomy.

2. Do You Work During Your Commute?

This question might seem like a a preemptive assault on a candidate’s work ethic, but I’m less interested in whether they’re a workaholic. I’m more curious about their passion for their job and desire to be prompt and responsive. Since startup hours can stretch long after normal quitting time, an employee whose passion keeps them on the ball is critical.


3. Would You Rather Tackle One Task At A Time Or Juggle Several?

You can learn a lot about a candidate from this one. Single-track minds tend to be more focused, but they can get bogged down in details. At a young startup, a team’s needs can change on a dime, so I prefer employees who thrive on transitioning quickly between tasks–developing, communicating, innovating, doing–all while keeping up a standard of excellence.

4. How Would You Respond If You Had To Start Over After Getting 90% Done With A Project?

This question measure how a person reacts to a sudden change in direction after putting in an enormous amount of effort. Do they see the new challenge as a fresh battle to wage or get frustrated and shut down? Or do they take a middle path, learn from what they’ve already done, and bring as much of it as they can to bear on the latest undertaking?

5. Do You Keep Your Work Email On Your Personal Phone?

This is a tough question for candidates to answer, and that’s why it’s so important to ask. I’m worried less about the “yes” or “no” than the “why.” A candidate who says they don’t do so isn’t immediately disqualified as long as they offer a confident, convincing reason for it. By the same token, if someone says they do check work email on their own device, but then explain they only do that because they’re too disorganized to also manage a company phone during working hours, that could be a problem. The point is that I’m looking for an employee who’s easy to reach, even if just to bounce an idea off of them now and then–and I care less about how they keep the channel of communication open.

6. How Long Do You Like To Go On Vacation?

Many startups don’t have a set vacation policy and tend to encourage staff to take the time they need. Still, I’m interested in learning how long candidates feel comfortable spending time away from the office. It can also be helpful to learn whether they tend to vacation for pleasure, for education, for personal growth, etc. Which leads to the next question…

7. Do You Check Your Email On Vacation?

People don’t join startups because they just need a job–they join startups because they’re excited to create something from the ground up. That, of course, means all hands on deck. Every opinion matters. So if an employee takes too much time off, there typically isn’t someone else who can take over their workload or match their expertise. By all means, I want a candidate who feels comfortable stepping back and recharging. But even if it’s just for an hour each morning during vacation, a willingness to check in and stay involved shows me an employee is committed to pulling their weight.


8. What Are You Really Great At?

This is a more direct way of asking someone to describe their strengths and weaknesses. Do they emphasize hard or soft skills? And how long do they take to respond? A quick answer might indicate more confidence, someone who chooses a path and blazes it. Slower answers hint at someone who’s thoughtful and deliberate, but also maybe a little deferential.

9. Where Do You Struggle?

The answer to this question should always be longer than the previous one. Startups need employees who are confident of their strengths but equally aware of areas where they can grow and improve. The ideal candidate doesn’t hesitate to let you know how eager they are to hone existing skills and build new ones.

10. What Do You Hate About The Workplace?

No working environment is all rainbows and butterflies. Startup workplaces can be especially intense, and some employees might resent the pressure. I want to know what kinds of things a candidate doesn’t deal well with. Do they hate being micromanaged? Can’t stand loud colleagues or a strict dress code? No one gets eliminated based on this question, but it does help me get a fuller picture of a candidate’s preferences–and maybe even help improve our office environment.


11. Do You Generally Prefer Strict Structure Or Full Creative Autonomy?

This question presents the two ends of a very broad spectrum. I’m not looking for a candidate who operates at one extreme or the other but one who’s malleable enough to succeed in either. Startup workplaces are fluid. Employees might work in complete isolation while designing an app, for instance, only to spend the next day breaking it apart during a marathon brainstorming session. Being able to adapt matters most.

Asking the right questions during the interview process can not only help you better understand potential candidates, it can also help your candidates understand you. However you adjust these questions to suit your own company’s needs, keep in mind that a finding a culture fit is about striking that balance. Each question should say as much about you as the responses do about the candidates answering them.

Yarden Tadmor is the CEO of Switch, a job-matchmaking app created to disrupt the job search and hiring space. Yarden has nearly two decades of experience launching and building a variety of technology startups.