4 Curveball Interview Questions

Interviewing as an entrepreneur can be tricky for several reasons.

First, the kinds of employees that thrive at big corporations don’t always do well at small businesses and start-ups and vice versa, so cultural fit is often as important as skills. At the same time, your team is small, making it even more important to get every hire right. And to top it all off, you may not even have a dedicated HR person to help you through the process.

Take these facts together and you can see why hiring for your small business can be incredibly difficult. Thankfully, there’s plenty of advice out there to help you out, including common mistakes to avoid and tips round ups that stress everything from writing solid job descriptions to trial periods and making a safe space for dissenting voices.

But at the end of the day, much of your decision about who to hire will often come down to the interview. So how can you get at not only whether a candidate is good at their gig but also is a good fit for a small business environment? OnStartups recently offered a dozen suggested questions to ask. Some of these ideas you’ve probably heard before (such as “tell me about a tough decision you had to make”) but others are both fresh and practical, including:

 “What concerns do you have about our company?”

The candidates you want to hire don’t think your company is perfect; they’ve done sufficient research to know that while yours is not the perfect company and the job is not the perfect job, yours is a company they want to work for because they can thrive, make a difference, develop and learn and grow and achieve… and be a key part of taking your company to even greater heights. And as a result they’re willing to honestly share their concerns.

 “Tell me about a time when you had to slog your way through a ton of work. How did you get through it?”

The candidates you want to hire can take on a boring task, find the meaning in that task, and turn it into something they want to do. Great employees turn the outer-directed into the self-directed - and in the process, perform at a much higher level. And gain a greater sense of fulfillment.

 “What were you doing the last time you looked at a clock and realized you had lost all track of time?”

We do our best when a task doesn’t feel like work but feels like what we are meant to do. I have never met an exceptional candidate that didn't at one point have this feeling where time didn't matter. Call it being “in the zone” or “flow” or whatever you want--all great people experience it.

 “What book do you think everyone on the team should read?”

If the person can't think of a single book that they'd recommend to others, that's a warning sign... Curiosity is a wonderful indicator of intellect and, oddly enough, modesty, because curious people are willing to admit they don’t know and are then willing to work to learn what they don’t know.