I’ve been told my interview style is “different.” But after interviewing dozens of candidates a week for years, I’ve learned a few things I hope will help other entrepreneurs trying to hire in this tough market. In a start-up like mine, hiring is ultra-binary: bringing on the wrong person sucks precious time and energy away from your most pressing opportunities, but hiring the right person can give your company the fuel it needs to accelerate.
Unfortunately, when faced with several candidates with impressive resumes, many entrepreneurs spend too much time "selling" their companies and not enough time transparently sharing their challenges. At the end of the interview, you have zero visibility into whether this candidate is a fit. All too often, entrepreneurs don’t ask the single most important question that can help them identify the best candidate: How would you solve our biggest business challenge? This challenge can be anything and changes over time. For example, your biggest challenge might be customer acquisition, and three months down the road, it might be fundraising.
Asking every interview candidate to solve your toughest business problem may seem like a hefty task, but I’ve found that being vulnerable and exposing your deepest, darkest challenge provides several important insights into the candidate. First, you'll find out if the candidate is the kind of person who is energized by a challenge or overwhelmed and scared by it. No matter how good the resume and pedigree, if the candidate is someone whose shoulders slump when presented with a gory mess, they’re probably not the right fit for a start-up. It's better to know that upfront. Problem-solvers who excel in the start-up environment physically lean-in, perk up, and are visibly energized when you share your deepest, darkest challenge. And those are the people you want to grab, hold onto, and never let go of.
Another benefit? When you noodle over a problem with people, you can tell pretty quickly how thoroughly they think through problems, and, as a result, how likely they will be to succesfully execute a plan. I look for people who think deeply enough to anticipate the hairy issues their proposed solution might raise, take these issues seriously, and naturally engage in planning for how to overcome them.
Finally, by batting around potential solutions to a tough problem, I can see if a candidate is genuinely collaborative. Everyone claims to be collaborative, but few people actually are. Luckily, this is a trait that’s remarkably easy to test for in an interview. True collaboration means having a willingness to discuss your problem-solving process with someone else and inviting them to provide their own solutions. Just listening doesn’t equal collaboration. And just ceding control isn’t collaboration either. You have to have the confidence to set the direction, but also the insight to be genuinely open to modifying your course based on other people’s ideas. There’s no better way to test whether someone is actually collaborative than to attempt to solve a problem together.
The other big advantage to asking this one question in every interview is that it actually “hooks” the right people. Candidates who are the right fit for the job won’t be able to get your problem out of their heads, because it’s real, and they’re itching to make a difference. To find people who will help you solve your deepest, darkest challenges, invite them to collaborate from the get-go.