Todd Humphrey | Crain's Portland

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Todd Humphrey


Launched in 2014, League is a tech company that simplifies and modernizes the benefits experience for employers and workers alike with a platform that connects them to a more comprehensive network of health services and benefits. The Toronto-based company recently raised $25 million for expansion. Todd Humphrey, co-founder and chief commercial officer of the company, is based in Seattle.

The Mistake:

I was running a startup about 10 years ago, and hired a VP from a big tech company for a role that I thought he was going to excel at. I did so primarily on reputation, as he was a pretty renowned salesperson.

I really didn’t do enough digging on him, in terms of whether he was the right person for our early-stage company, because he was coming from a completely different environment. I think it ultimately cost us a few months – and probably a lot of opportunities – revenue-wise, which is a lot when you’re an early-stage company. It was then that I thought, “I’ve got to readjust the way that I hire people, and what my decision-making criteria really are.”

To hire the right person, you have to look beyond the resume.

The Lesson:

To hire the right person, you have to look beyond the resume. People can go online and create an amazing description of who they are via the written word on their resumes, LinkedIn, and introductory letters to hiring managers. So when I interview people now, I don’t just ask questions like, “What have you done in the past? What are you doing today? How do you imagine your career evolving with us?” I want to talk a little more holistically with them.

I’ll ask questions that put them on their heels to see how quickly they think on their feet. Some of those random questions I might ask are, for example, “If you were in a band, what instrument would you play?” Not everyone needs to be a lead singer; I just want to understand who they see themselves being in a small group situation like that.

I’ll also ask some other questions involving team-like scenarios, like, “If you were on a football team, what position would you play?” Moving away from the work environment, I’ll ask a question like “How would your best friend describe you in three sentences or less?” I want to peel back the layers of the individual to get a sense of who they are and how they do things on their feet.

I always give people about a minute to answer this one: “If I was to give you a million dollars to start your own company, what would your idea be? What would you start tomorrow?” Some people are just dumbfounded. Some of the people you don’t expect come up with amazing answers. If they’ve never thought about it, I kind of question whether or not they could work with me, because I think a lot about those kinds of things. But f they can come up with a good answer – even if they’ve never thought about it before – I’m impressed.

Follow League on Twitter at: @JoinLeague

Pictured: Todd Humphrey | Photo courtesy of League

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