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Four Questions This Founder Asks Himself After Interviewing Job Candidates

No two job candidates are the same, so this startup founder came up with a mental debrief for assessing their relative strengths after each interview wraps.

Four Questions This Founder Asks Himself After Interviewing Job Candidates
[Photo: JESHOOTS.COM]

Ever since I was hit in the face by a pitch playing baseball, my flinch reflex became embarrassing. I was always freaked out by pitchers who threw really hard–not a good trait in a batter.

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I was reminded of that the other day tossing a ball to my toddler (yes, him). He dove away from the ball after being bonked on the head one too many times, and something dawned on me: Everyone’s afraid of the ball, just at different speeds.

As a startup founder, I’ve realized it’s much the same with the level of uncertainty people can handle–one key trait among several that I’m always looking for in job candidates. No doubt everyone deals with some degree of uncertainty at work, but it’s much more intense when a company is young. The business model, target customers, financing, and everything else are chaotic at the beginning. As things solidify over time, the level of uncertainty goes from scary levels back to something more normal.

So while there are lots of great questions a hiring manager can ask to determine whether somebody will thrive at their early-stage startup, I’ve also found it helpful to run through a mental checklist after finishing up each interview. This helps me step back and assess what I’ve learned about job candidates based on common criteria–all with an eye to the uncertainty they’ll inevitably face once they come on board.


Related: The 7 Questions Recruiters At Companies Like Amazon And Spotify With You Would Ask Them


1. How Fast Are They Ready To Move?

All companies are tinkering with aspects of their business, but startups are often tinkering with their very foundations, and often at a rapid clip. Some people love that; others find it frustrating and jarring.

The trouble is, laying the foundation often sounds great to people who may not understand what it actually entails. Worse still is that lots of people think they’re supposed to want to do it, which leads them to take startup jobs that aren’t good fits for their personality. So I ask myself this question in order to reflect on how quickly someone may be able to adapt to continuous change.

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What I’m looking for:  Most people don’t think about the fact that being nimble means quickly stopping things, not just launching experiments all the time. Task switching isn’t just a productivity drain; it can drain your energy and enthusiasm for the work itself.

During the interview, I like to ask candidates to describe a time they’ve had priorities shift suddenly on them and had to go full-speed in a new direction. Afterward, I ask myself what their answer might reveal about how they’d handle similar scenarios here: Did they abandon good habits and behaviors when they had to move in another direction, or did they refocus and keep doing things the right way? If people can’t stay productive as the floor shifts beneath their feet a bit, it could be a bad fit.

2. Are They Comfortable With Big, Unanswered Questions?

The ability to influence big decisions is one of the best things about working at a startup. In the right circumstances, that creates an infectious energy on the team. But being unsure of critical things like who the ideal customer is or what the right product for them might be can feel unsettling, too. Some see opportunity there while others see risk–and they’re both right.

What I’m looking for: While interviewing, I ask job seekers to describe a project at work that’s forced them to answer big, open questions. I prod for details about how they figured it out, which mistakes they made, how their team responded, what the pressure was like, and how they ultimately dealt with it. While debriefing afterward, I ask myself whether the experience they shared with me suggests that they’re good at confronting challenges of this scope. You want people who are eager to solve problems and answer questions, and who can roll with the punches as they figure things out.

3. Can They Let Things Go?

Throwing away work sucks, but it’s part of startup life. You have to act fast when opportunities arise, and that sometimes means shelving yesterday’s priorities. Startups need to hire people who’ll be okay with that if it’s good for the business, rather than resent not being able to finish something they’ve worked hard on.

What I’m looking for: I play back in my head how they’ve described a time when they had to switch gears, and how it affected them personally. It’s okay if they grumbled a bit about whether the decision was the right call for the business. If they mostly grumbled about the inconvenience for themselves, though, that’s a potential red flag.

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4. How Will They Feel When Growth Stalls?

Most startups don’t launch and suddenly take off at breakneck speed. They slog on for years before they make it (or they don’t). The paradox of startups is that the chance to build something means that what you build may not survive for long. It takes fortitude and optimism (and sometimes blind faith) to stay focused when you’re searching for product-market fit. The so-called “valley of death” that many startups fall into, when they’re cash-strapped and waiting for revenue to start coming in, is unavoidable. So after meeting with job candidates, I try to consider how each of the people I’ve interviewed will respond in that environment.

What I’m looking for: I’ll typically ask candidates about the lowest point they’ve had on a project or in a job. What caused it, and how did they get through it? Did it change, or did they leave? Every situation is different, but when comparing candidates’ responses after the fact, what I’m looking for is someone who doesn’t run at the first sign of trouble and wants to see things through. Trouble will inevitably come, after all.

Aside from compensation changes, the biggest risk of taking a startup job for most people is the opportunity cost of pouring their heart and soul into something that doesn’t pan out. Since every candidate has had unique experiences and will describe their work history differently, it’s helpful to review each of their responses based on these five fundamental questions. That usually helps me determine just how much uncertainty a candidate can stomach–and whether they’re the right person for our business right now.

About the author

Christian Bonilla is the founder of UserMuse, which curates market research panels for enterprise software companies. He posts frequently on UserMuse's blog.

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