Hiring for Adaptability: Why Most Interviews Get It Wrong

In all my years of interviewing, I’ve never been asked how I approach adaptability. Sure, I’ve been asked plenty of indirect questions about how I handle changing situations, but no one has ever asked about my overall philosophy on adaptability. And yet, I’d argue it’s one of the most important characteristics a person can have at work and in life.

My theory? Most interviewers focus so much on whether a candidate can do the job today that they overlook whether they’ll thrive as the job evolves. That might be a broad generalization, but in my experience, it holds a lot of truth.
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When I was managing project-based consulting practices, I struggled to find people who could truly succeed in that space. Every project, every client, and every problem was different from the last. People who weren’t adaptable at their core, no matter how smart or skilled they were, simply couldn’t succeed. Eventually, I developed an interview technique that, once refined, completely eliminated unsuccessful hires. I’ve used it for over a decade.

Hank’s Sandwich Shop

Anyone who has worked with me over the last decade probably knows about Hank, the sandwich shop owner.

The scenario is simple: Hank has been running a sandwich shop for decades in the same location. He is very much a Luddite. But in the last few years, a technology park has sprung up around him. His customers love his sandwiches and desperately want to order online. Eventually, he gives in and asks for help. That’s where the interviewee comes in.

I’d set the stage and say:
"Hi, I’m Hank. So, now what?"

This wasn’t a theoretical discussion. I became Hank. The interviewee had to role-play, speaking to me as if I were the small business owner asking for help.

This exercise was invaluable. Unlike standard interview questions, this method got to the real person, not the polished, rehearsed version. You can’t fake adaptability in a live interaction. If a candidate made assumptions, Hank had no idea what they were talking about. If they threw out jargon, Hank pushed back. Sometimes, Hank was a bit skeptical. After all, the person on the other side of the desk didn’t know anything about sandwiches. Within minutes, I could tell whether they were truly adaptable or just good at giving prepared answers.
I wasn’t just looking for technical skills. I wanted to see how they reacted when their initial approach didn’t work.

The second part of this technique was even more revealing. Right after the role-play, I gave the candidate direct feedback, as if I were their manager reviewing their work. Did they get defensive? Did they listen, process, and adjust? Could they reflect on what they’d do differently next time?

I’m not exaggerating when I say that after implementing this technique, I never made another misaligned hire.

One of the most memorable responses? A candidate started with:
"You should just sign up for Uber Eats."

It was so brilliantly simple it caught me off guard. I hired them.

​Why Does No One Interview Like This?

I have a couple of dozen articles I plan to write before I leave this mortal coil, but this one felt particularly important this week.

I’ve been actively job searching for a year now, and I’ve never had an interview like this. In an industry addicted to accelerating change, why is adaptability never the focus?

Companies, Microsoft in particular, love to talk about the importance of a growth mindset. For the record, I love that book, that philosophy, and try to live by it. But to me, you can have adaptability without a growth mindset. Adaptability feels like a more fundamental, elemental trait. It is something you need regardless of whether you’re actively seeking growth.

I asked ChatGPT why interviewers tend to zoom in on isolated examples of adaptability rather than assessing it as a broader characteristic. The response?

Interviewers structure interviews around their own perspective, biases, and what they think they need for the role.

And I have to agree.
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Making an unsuccessful hire reflects poorly on the hiring manager. So, the instinct is to control as many variables as possible to minimize risk. But in doing so, they end up chasing a fear of failure instead of pursuing the possibility of success. (I know that last sentence feels like a cliché, but I couldn’t help myself.)

​The Trigger for This Article? My Own Career Path.

On my morning run, I was thinking about the roles I’ve held over the past twenty years. It should be obvious that I’m highly adaptable. I’ve succeeded at every level, in every environment and those successes were anything but linear.

But there’s a bias that cuts both ways:

• "You’ve never worked at this level before, so you couldn’t possibly do it."
• "You’ve worked at a much higher level than this. Why would you want to do something different?"

In my case, sometimes my role changed by choice. Many times, it didn’t. And yet, every time, I adapted and (eventually) thrived.
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One of the most profound experiences of my career was transitioning back to managing an engineering team at Bluetooth SIG. I wasn’t sure I was up for it as it had been well over 15 years since I had written any code. In the end, it turned out to be one of the most fulfilling jobs of my life. I watched my team embrace adaptability—not just as a necessity but as a strength. I know the organization was stronger because of it. That experience is what started me writing about my philosophy of management: https://www.syme.info/writings/cultivating-self-managing-teams.

​What Should Hiring Managers Do?

If you’re a hiring manager staring at a stack of resumes, take a second to think about who might actually help Hank the most.

Don’t just ask for a single example of adaptability. Find out how they think about it. Because the best hires aren’t just good at handling change when it happens.
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They expect it.
They embrace it.
And, when the time comes, they drive it.