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How to Conduct an Interview: Asking Powerful Questions

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When you ask people questions that have been curated just for them, you give them the power to step into their own space and express themselves. You’re also saying to them: “hey, I really give a shit.” This is a pure form of hospitality.

We’ve noticed that because we spend our time catering to folks in an industry that we grew up in, there is a lot of animated and impassioned discourse that I don’t think we would find if we were interviewing, say, tech nerds. This is powerful. It tells us that we need to keep poking this particular box because it lights people up.

We consider it part of our service that we get our clients thinking about their business and humanity in ways that perhaps they hadn’t considered before. This means that sometimes we’re asking questions that are a bit deeper. If an interviewee doesn’t stand to learn as much from thinking about the question they’re asked, as we do from hearing their answer, then we haven’t done our job.

I’ve noticed from the interviews we’ve done so far that the three of us at the Nimble Bar Company are attracted to asking questions that tease out different kinds of answers.

Questions that connect you to humanity:

  1. As you know, this industry isn’t always easy. Who are the people that inspire you to soldier on?
  2. You have fostered some long-standing and solid relationships, you’ve also built some great teams. In an industry that is often seen as transient, how can people build great teams that are meant to last?

Questions that connect you to your product and environment:

  1. Mezcal and Mexicania have become very trendy in the last few years. Why do you think this is and where do you think this trend will be in 5-10 years?
  2. You’ve had a tough night. What’s your after work medicine?

Questions that yield actionable tactics:

  1. Why are we so far away from great service in so many establishments? Why is it that your establishment has succeeded at great service and what is the one thing you would recommend others adopt?
  2. As an owner/manager, what is your biggest pain point? In an ideal world, how would that be taken care of?

Conducting a great interview is about touching all the bases that effect the interviewee’s business. From day-to-day minutiae, to the pivotal moments of success that have been worked toward for years, and as much as possible in between.

What questions do you suggest we ask our interviewees in the future?

Kyle Guilfoyle

Kyle Guilfoyle

Kyle is co-founder and CVO of the Nimble Bar Co, where he helps bars and bartenders create theater so that they can be more profitable and have more fun.

Let us know what you think!

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