What is the story you tell yourself about your career?

This is the question I begin every job interview with.

The question manages to cover a few bases at once. It puts the candidate at ease by letting them tell a story on their own terms. It gives the interviewer the chance to quickly understand the progression that can otherwise be hidden inside a resume. It allows the interviewer, as a future colleague or manager, to gather information about how to put the candidate in a position to be successful. And it allows the interviewer to test for softer skills around communication, leadership, and dealing with uncertainty.

It’s also a question that reflects my own understanding of my growth at Squarespace as the company grew from fewer than 70 people to 1,200. Along the way, all sorts of things went wrong. Every detail changed. That rate of change made many people deeply uncomfortable. Internal storytelling is what allowed me to cope — I worked hard to find meaning in opportunity in each crisis, each colleague’s departure, each mistake I made. I look for candidates who are able to exhibit the same flexibility and optimism

Here’s what I’m looking for as I listen and dig in with follow-up questions:

The basics

Do they communicate clearly and succinctly? It’s shocking to me how many people will run on, uninterrupted, for well over ten minutes in response to this question. This generalizes to their ability to lead teams and sway others.

Do they have a good sense of what is important and what is not? When candidates focus excessively on the details here, it’s a flag that usually shows up again later in the interview.

Do they think critically about their own strengths and weaknesses? This makes me more confident in their ability to gravitate toward the right work and responsibilities.

The downside

Do they tend toward negative interpretations of their circumstances? Bad things happen. But it’s not always someone’s fault, and it’s not always permanent. The ability to stay optimistic itself makes success more likely.

Do they go out of their way to bad-mouth others? A surprisingly large number of people will talk about how their boss or colleague was a jerk or an idiot or acted in bad faith. That’s poison.

Do they exhibit an unhealthy relationship with ambiguity? Some candidates gravitate to ambiguity like a pig to shit; this is not a recipe for organizational clarity. Others run from it, screaming; this aversion is likely to produce conflict and reduce risk-taking. I’m looking for a healthy balance: No instinctive fear of uncertainty, but also an understanding that uncertainty should be contained and minimized where possible.

The upside

Do they own their choices and mistakes? Ownership builds trust with others, and suggests the candidate can learn quickly.

Do they appreciate the impact that environment and luck have had in their own development? No one got here alone, and no one should be judged in isolation. I trust that candidates who exhibit this understanding make better managers and more empathetic colleagues.

Are they able to construct meaning from seemingly meaningless events? In many ways, this is a test of resilience. Candidates who are able to tell themselves a story about where they’re headed are more likely to roll with changes, and to know how to update their own story to account for those changes. This deep storytelling ability serves as ballast in rough seas.