Thomas Hansen | Crain's Philadelphia

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

Thomas Hansen


Dropbox is a technology company that provides secure online file-sharing services and storage solutions to customers.

The Mistake:

As context, I was born and raised in Denmark. I grew up, not in a strict environment, but in a disciplined environment where you respect your parents, grandparents, teachers. So, super early in my career, my mid-20s, I’m working for a U.S. PC manufacturer in South Africa. It’s my first job as a people manager, a sales manager. I’m out hiring, and I had this notion that you hire seniority, people with experience, and they’ll get the job done because they know how to do it. So I hired a bunch of people and some turned out really well—then there was one that probably is the worst hire of my career. Within two months I knew he had to be exited out of the organization. We had complaints from female staff, from customers around his conduct. 

I came to learn that he had a nasty streak. And one of the things that is similar between South Africa and the U.S. is there’s access to guns. We knew this gentleman was carrying. So it really came down to, who’s going to pick the short straw and have to sit down with this gentleman and inform him, “Buddy, you’re fired and you need to leave.” 

We sat him down and offered him an unusually high amount of money simply to get out. I remember sitting with him, and I was internally shaken, but on the surface probably steady. I offered him X dollars, and he looked me straight in the eyes and asked for 2X. I said, "Done." After a few months at a competitor, he got fired for the same reason.  

When you hire ... attitude makes up for a great deal.

The Lesson: 

One thing it taught me was, don’t hire for experience only. Don’t make assumptions that you should respect someone because they have a certain set of experiences or are senior to you. As always, when you hire, it’s a blend of attitude, aptitude, skills, capabilities, competence and experiences. And the core lesson I learned from this is that attitude makes up for a great deal. In hiring I started to pivot more to what is it that we’re trying to solve for in the role, versus a set of experiences. 

Soon after, I was looking for an account manager. Jonathan had never worked in IT. He had never been a seller before. Jonathan was a priest. He could relate to people. He had the right attitude and the right hunger for why he wanted to come into IT and sell. And he became one of the most successful account managers I’ve ever hired in terms of building customer loyalty.  

That earlier bad hire also shaped something else in me. I mentioned that I grew up in an environment that put me in a place where, as an individual, I probably had a bit too much respect for those around me: authorities, elders, and also, say, my manager or manager’s manager. Earlier in my career I had a certain amount of, not even respect, but fear. It caused me to behave in unnatural ways where I wouldn’t be myself, wouldn’t take the risks, and wouldn’t bring the best out of myself.  

I had an aha moment, years back, where I met a very senior person, three layers above me in the organization I was working for at the time. This individual had a reputation for being very tough, very demanding and so forth. I walked into the meeting fearful, expecting to see this machine who just wanted to drive for the hard, cold numbers. And 45 minutes later I came out with a feeling of relief, excitement, and almost shock. The person I had built up in my mind was exactly the opposite, a person who had empathy and wanted to engage. 

It set me free and made me realize, it’s pointless to have fears. What’s the worst thing that could happen in your career? That you get fired? So what? The alternative to having fear is, if you take some risks, and if you fail, you learn fast, sell fast and hopefully not repeat the same mistakes too many times, and you have amazing things you can accomplish. In the 15-plus years since I’ve made that decision, I’ve taken risks that have accelerated my career and the impact of the work that I’ve done. 

If it doesn’t kill you, it makes you stronger, and in that first case, it certainly was true. 

Find Dropbox on Twitter at @Dropbox

Pictured: Thomas Hansen. | Photo courtesy of Dropbox/Thomas Hansen.

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