The biggest hiring mistake I’ve ever made is allowing executives to skip skills tests

What went wrong? We didn’t actually interview Tim (not his real name). We did a lot of chit-chatting, selling, and reference checking, and we even took him and his wife out to dinner.

But we did little to actually assess whether he’d be good at the job.

With two decades of experience at highly respected tech companies, Tim looked like the perfect exec to lead an important team. Six months after we hired him, we both realized we made a very avoidable mistake and parted ways.

Thumbtack, where I was the VP of product at the time, was several-hundred people strong when we met Tim. It had a highly structured hiring process that relied heavily on in-person, exercise-based interviews: whiteboard coding and pair-programing for engineers, consulting-style case interviews and wire-framing design challenges for product managers.

Yet with Tim-and several other execs that also didn’t last a year-we didn’t do any of that. The more critical the hire was, the less rigorous our interview process tended to be.

We assumed that people with 20-plus years of experience were so awesome at their jobs that we didn’t need to verify it. We feared that having a group of no-name, barely 30-somethings put these more senior candidates through exercises was arrogant and pedantic. We were wrong. Execs should absolutely be tested before they are offered a job.

The candidates I want don’t scoff at doing exercises, they relish them. The people who succeeded at places like Thumbtack love solving hard problems and have fun doing them in an interview.

Hard interviews are even part of a good sales pitch. Great people want to work with great people, and hard interviews help demonstrate the bar is high.

It takes a lot more work to design a great exercise-based interview than one comprised of “tell me about a time when” questions, but it’s worth it. If you really don’t have the competency in the building to asses an exec’s skill set, lean on advisors. With executive hires, I now design exercises that test both for how they tackle a broad problem and how they handle problems down in the weeds.

A successful exec interview process doesn’t just prove to one or two decision makers that the candidate is great but also a broader team. Getting a new boss is scary, and I want a team that is getting a new leader to have confidence in him or her. There’s no better way to do that then to show them that an exec can solve these hard interview puzzles.

Failing to put Tim through a set of exercise-based interviews was one of my biggest unforced errors at Thumbtack. As I start building my new company, I’m not doing the same thing again.

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