As I’ve mentioned in just about every blog post I’ve written, we’re winging this thing. One of my favorite things about our trajectory as business owners is that you can count our business degrees on zero hands. We’re building a company primarily on intuition and luck. A big part of our growth has to be attributed to the team we’ve put together. Perfect Strangers. We seem to attract great talent with one thing in common. They all take their work seriously, but not themselves. How did we do that?

Maybe it has something to do with our interview process? That would be interesting considering I have even less HR experience. I like to keep interviews pretty casual. For a while, I was breaking the ice by challenging the candidates to a game of Connect 4 before a single question was asked. And no, you don’t have to lose to me on purpose to get a job. Just ask Amanda.

My guess is that I’ve conducted around 150 interviews over the past 10 years. And, I’ve been asking a handful of the same questions almost every time. When I think about it, they’ve been pretty good at successfully identifying a “Weird / Smart” type of person. In no particular order…

1. Have you ever had a roommate?

This is one of my favorites. First off, if you have NEVER had a roommate, joining our company is going to be a RUDE awakening. We’ve described our culture as brothers and sisters (no kidding, the girls have a clothing swap about every other month). Bad at sharing? Not a fit. Need a ton of personal space? That’s gonna be tough for you (although, we are doubling our space with the new office opening this Summer). And if you’ve never had a bad roommate, you ARE the bad roommate. Most def not a fit.


2. When do you pick up the phone?

It’s a little weird but it’s awfully telling. Truth be told, I have some room to improve on this one. This question is all about understanding whether or not the candidate is willing to pick up the phone and solve (or explain) a problem in-person, over the phone. It’s VERY easy to write an email a mile long that explains a problem or complicated situation. I promise the client doesn’t want to read it. They want to know the problem is getting solved. That’s best communicated over the phone. And, it gives you the opportunity to use your charming personality to your advantage, right? Tell a joke, fall on the sword, whatever. Just let the client know we’re on it. Calling is scary. Get over it.

In fact, I like to make this question interactive. Say “stop” when an email gets long enough and you pick up the phone instead…


3. What questions do you have for me?

Flip it around. After all, you’re interviewing US too. A company needs to be a fit for you just as much as you are a fit for them. Get creative. Get weird. Ask me what type of kitchen utensil I’d be, or whatever (butter knife, by the way… juuuuust sharp enough).


4. Is this interview going the way you expected?

I love asking this question for 2 reasons. One, it breaks the tension. I typically ask this around halfway through the interview. Almost always, it’s the most well received question to that point. You can visibly see them relax. It’s easy to answer. There is no wrong answer.  And right about this time, you get a glimpse of their “real” personality and not whatever they put on just to get through the interview. Second, it allows the candidate to backtrack and answer something again if they want. It’s kind of like a do-over. I would appreciate that if I was on the other side of the desk.


5. What’s more important? Winning or Losing?

I’ll probably have to quit asking this just in case you’ve read this blog. But, it’s a trick. I like to win. It’s just about my favorite thing. But it’s not as important as losing. You don’t learn as much from winning. Winning tries to make you comfortable. Winning wants you to relax. Losing stokes the fire. Losing reminds you that you can (and will) lose. On rare occasion, this gets answered perfectly. Sometimes a candidate will tell me about something they lost and why they wouldn’t go back and change it if they could.

Queue my story about senior year region finals…