Jill Hamilton Buss | Crain's Orlando

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

Jill Hamilton Buss


Healthy Central Florida is a community-based partnership established by Florida Hospital and the Winter Park Health Foundation to create healthier options in communities with high rates of obesity, inactivity, smoking and mental health challenges.

The Mistake:

When I was working at my first job out of college I was very idealistic and a little bit self-righteous. I thought that the owner of the company should have been doing things a certain way and treating people a certain way. I just knew everything, and he didn’t know anything, kind of. And I was frustrated a lot because [I thought], “You should be this and you should be that.”

And I remember going to lunch with an older friend, a professional colleague who’s been around the block and there I was complaining, and he said, “Let me give you some advice.”

He took out a napkin and he drew a little diagram and said, basically: “Here’s the company owner’s position right here, and here’s your position down here. And here’s the door over there. It’s his company. and if you don’t like it, you can go start your own company and run it the way you think everything should be run. It’s really that simple."

But then he said, “Rather than being frustrated, figure out how to sell him on how to do [something] better or the benefit in doing it the way you want to do it.” 

It was just an illuminating conversation, for a person early in their career. It didn’t occur to me to leave – I loved my job. I was young and freshly out of school and hadn’t figured out how to sell the boss on a better way. It was easier, frankly, to complain. I hadn’t realized that I kind of had the power to have him do things differently through building a good case and a good argument.

I was young and freshly out of school and hadn’t figured out how to sell the boss on a better way.

The Lesson:

I went at [my job] in a much different way so it reduced my stress. It made me enjoy my job more. It made me have more respect for the owner and what he had built.

I save everything, and I have a file of magazines from those early days, and I have found so many memos I wrote – after that conversation –that were rationales on how to or why to do XYZ. Recently, I ran across one of the memos, and I was like, “Wow!” It was thoughtful … If I were him, I would have done what I recommended.

I just think that it was a good reminder always to remember that – good, bad or indifferent – they are the boss, and you always have options. You may not be able to sell someone on your ideas. You may ultimately decide that they aren’t the right fit for you or the company’s not the right fit for you. But while you’re there, you can also change things. And you’re only going to change things with good data and arguments and strategies that show there’s a better way. 

Follow Healthy Central Florida on Twitter at @HealthyCentralF.

Pictured: Jill Hamilton. / Photo courtesy of Jill Hamilton.

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