Dick Morgan | Crain's Denver

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

Dick Morgan


Rocket Software is based outside Boston and has 31 offices around the world, dedicated to improving software infrastructure for businesses large and small.

The Mistake:

There's definitely one early-career "aha" moment that kind of occurred to me later. It was around the idea of it being possible to establish a really strong partnership with your boss without always seeing eye-to-eye on decisions or on business approaches.

I've been in HR for quite a while. I've worked for CEOs, really, for the past 20 years. Earlier in my career what I thought was the right job or the best job for me was one where I was working for someone who I thought I saw eye-to-eye on with everything. There were a couple of jobs that I walked away from—that I really regret walking away from—because I felt at the time that without having that strong connection with my boss, it wasn't going to be a good job for me. But what I've come to realize later in my career is that part of any good relationship with your boss is you're going to have situations where you don't see eye-to-eye and that's perfectly OK.

For example, I worked for a big, publicly traded but family-run business in which the father was the chairman, and the son was the CEO. I had a good relationship with the son, but the father chairman and I didn't necessarily see eye-to-eye. Oftentimes, being in HR, it was people decisions—hiring and firing decisions.

And I ended up leaving sooner than I should have. I decided to leave and I walked away from a really, really good job. What I would say 20 years later is that I could have made that work, and I could have made it work well.

Have confidence in your ability to improve the relationship.

The Lesson:

It was a retail consumer products company. Most of my career has been in high-tech, so this was my one foray outside of high-tech, and I was uncomfortable with it because of that lack of connection with the chairman. But as I look back on that I realize you can actually influence executives' viewpoints over time by building trust and working on that relationship.

A lot of times you hear about people who stay too long. You don't hear a lot about people who leave too soon, but I do think part of what experience brings is the confidence that comes with knowing how to ride out the ups and the downs. I'm definitely not as easily rattled as I might have been in my 30s. The other side of the coin, I think,  is that people who stay too long in jobs get too complacent.

Finding that middle ground where you're challenged, and it's not always comfortable—that's kind of my lesson learned.

I think another lesson is to have confidence in your ability to improve the relationship. Be comfortable with the tension that comes with that, and be confident that even in that kind of situation you can still be successful and things can improve. I think that's especially true today given how politically charged our country is in general. It's a great quality to be able to work with people who you aren't perfectly aligned with on every single topic.

Follow Rocket Software on Twitter at @Rocket.

Photo courtesy of Rocket Software.