By Sean Harper, CEO and co-founder at Kin Insurance

For startups, a successful hire is as much about fit as it is about skillset. You don’t just need someone who knows Ruby; you need someone who knows Ruby, is self-directed and is comfortable learning on the go and living with uncertainty. Candidates with a track record of startup success are a natural fit, but I’ve also found that a certain breed of “corporate misfit” can make a great addition to a startup team. These hard workers often apply to startups because they want to spread their creative wings. They feel limited by the rigidity at their current organizations -- and they often have invaluable industry insight.

But startups aren’t all brainstorming and ping pong. To figure out if your startup is the right place for corporate misfits, I recommend asking the candidate three questions during the hiring process: Could you, should you and would you work at a startup (and, specifically, at your startup?). Here’s a look at why these questions are so valuable.

‘Could You?’: Look for experience with failure.

The goal of the “could you?” question is to determine whether a candidate with a corporate background could succeed in a startup environment.

To tackle it, flip it on its head: What would prevent the candidate from succeeding at a startup? For one thing, discomfort with failure: During the hiring process at Kin, we ask questions about failure and experiences that didn’t go as planned. We want to know how candidates have handled past failures and look for those who are open to the idea of seeing failures as learning opportunities.

Another essential “could you?” question: Are you comfortable in a less structured work environment? Startups typically build products, not structure. Candidates need to be independent and self-directed. They may be given a “what,” but have to figure out a “how.”

We also ask about stress: Is the candidate equipped to handle stress? Specifically, will the unique stressors of the startup environment (limited resources, long odds, unproven methods) clash with their personality or max out their tolerance for uncertainty? Can they handle seeing the end of their runway two months away?

‘Should You?’: Assess long-term goals.

Startups typically don’t offer clear promotion paths, but they do provide opportunities to innovate, experiment and gain a broader experience than would be possible in a corporate setting.

“Should you?” questions seek to determine whether the position at your startup really aligns with the candidate’s long-term goals. If a candidate is looking for a clearly defined career path with a fixed bonus structure, a startup is probably not a good fit. If they’re looking to develop a variety of competencies (for a generalist role) or dig into really gnarly problems (for a specialist role), then your startup may be an excellent fit.

‘Would You?’: Get into details.

Assuming a candidate could and should work at a startup, it’s time to assess whether they would actually accept an offer if you made one. The goal of “would you?” questions is to make sure the candidate understands what they’re getting into at your company specifically.

Many jobs seem exciting and fun during the interview process, but in reality, all jobs have ups and downs. Given this candidate’s goals and background, would they feel frustrated after three months? Would they crave better organization? A clearer salary structure? Different opportunities?

Another important component of “would you?” questions is whether the candidate has what I call “startup scars.” Have they worked in a dysfunctional startup in the past? Have they worked at a typical startup and found they disliked parts of the experience that they’d have to deal with at your company?

Startup scars don’t mean a candidate is a bad fit -- but they are important to address, especially if working for your company is likely to reopen them and make for a bad experience for all parties.

Look for self-awareness in the interview process.

Whatever versions of these questions you include in your interview process, I recommend paying careful attention to the answers. Whether they come from a corporate background or not, candidates tend to be most successful in startups when they’re self-aware, inquisitive and comfortable thinking about both details (like whether they have the skills to do the job in question) and the big picture (like whether they’ll work well within your organization).

These are the clear-eyed, self-motivated workers who have both the technical chops and the emotional maturity to get the job done -- even without a road map.

Sean Harper is CEO and co-founder at Kin Insurance.

Published on: Jun 20, 2019
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