When I think of leadership, I think of how much a great boss can make the work experience fantastic and even give your personal life a lift. By contrast, a lousy boss can make life feel miserable. 

Even for myself, I think of one of the first bosses I had when I was an intern at Chrysler. His name was Billy Brickels, and he was an ex-military guy. 

I was in the first weeks of my internship and I was so nervous; I was trying to do everything right. I wanted to make sure that Chrysler wanted to hire me back full-time. 

Billy had given me an assignment to update my internal calendar and make sure it followed his preferred protocol. So I sat down at my desk, updated my calendar with all the meetings I was supposed to have, and ensured that it followed precisely the template he gave me. Then, I sent him an email and said, “Hey, Billy, can you take a look at my calendar? I’ve updated it per your request.” 

To that, he sent me a one-liner back that said, “Don’t give me assignments.”

I remember being absolutely floored. I walked away from my desk and power walked to the nearest bathroom. My eyes filled with tears. As I tried not to smear my makeup I thought “Oh my God, I’ve already blown it. I’ve only been here one week on the job, and I’ve already completely blown it. How could I have blown it already?” 

After I pulled myself together, I headed to my team members desk. I pull a trusted member over and mentioned what happened (attempting not to show how shook I was). 

“Oh yeah, that’s his style. What he really wants you to do is for you to take leadership and independently go figure things out and work independently to get things done. As you make progress, he wants you to share back to him and let him cross-check your work if it’s off track.” 

I quickly learned that it was better to go ahead and do the task, and then shoot him a note when it was complete as an FYI. And from there, if he wanted to coach me, he’d reach out. Otherwise, move forward. 

Billy had a particular style of working. He also wanted me to go to my team and ask my team questions so that we would gain a really tight working capability and keep him out of all the details.

So this was his way of teaching us how to work independently and NOT need him for everything. This gave him control to make sure that he can provide direction and steer us when things were off course. 

The whole experience was terrific because, by the end of the internship, I learned this rhythm of working with him where I would go ahead and take initiative and say, “Hey, Billy, I went ahead and I did the project this way, and I made the decision to do this. Just an FYI.” And then he would only follow back with me if I was off course. He would coach me when I was off course, and if I was on course, he would say, “Great job. Keep going.” Boom. That would be the end of it. 

It was an ice-cold start to the relationship but my last day on the job was so memorable. Billy arranged to borrow a Viper and take the team out for some test drives. And Billy gave me a five-star review! I just remember him being incredibly supportive and saying he was impressed by how much I could accomplish under his leadership. I think he was right. 

Billy’s style was unique, but it instilled confidence in me and changed how I thought of letting people run with the ball throughout my career.

When you think of your Best Boss, who comes to mind?

For more inspiring stories on some of the Best Bosses Ever, check out my podcast on Spotify or Apple.

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