Be the Person Who Believes in the Dumbass
The best leaders don't just build successful organizations. They build better people.
I was recently asked if I would be willing to give a speech at my boss's retirement dinner. My answer was, "Does a bear shit in the woods?" I dunno why I love that saying so much. I guess because I like bears. Yes, bears shit in the woods.
It wasn't until I sat down in front of my laptop a few nights later that I realized what I had signed up for. It wasn't because I didn’t have shit to say. It was because I had too damn much, as usual. How do you summarize almost a decade of someone's influence in five minutes? Do you talk about programs we built together? The promotions? The awards? None of it felt right.
Success Looks Different at Forty Than It Did at Twenty-Five
When I was younger, success was easy to define. Get promoted. Make hella money. Earn another title. Repeat until you retire. Honestly, I mean I still want those things. I'm pretty ambitious, and I don't think ambition is a bad thing. But, like with everything else, becoming a husband and a dad changed my perspective.
I still care about climbing the ladder, but I also find myself thinking about what happens after the ladder ends. Nobody stands up at a retirement dinner talking about quarterly reports or budget spreadsheets. Nobody says, "Remember that incredible strategic plan from 2018?"
The Best Leaders Give You Opportunities Before You Think You're Ready
My boss trusted me with projects that I wasn’t comfortable with, meetings I sure as hell wasn’t qualified to be in, and responsibilities that forced me to grow and learn fast. Looking back, I wasn't always ready for those opportunities, but that's exactly why he was a good boss.
One of the proudest moments of my career happened during one of his speeches when he recognized me in front of a room full of people. A room full of very important people. I wrote about that here: Facts vs. Truths: Why Truths Matter More... Usually. It's amazing how a few sincere words from someone you respect can stay with you longer than a raise or a good job review.
The Best Leadership Lessons Had Nothing to Do With Work
I kept thinking back to the most important conversations we'd had over the years, and barely any of them were about my actual job. The ones I remembered most were about my wife, my kids, and trying to find some kind of balance between building a career and building a family.
Here I was trying to write about someone's professional legacy, but the memories that I kept thinking about were not about actual work. They were conversations about being present, remembering that careers come and go, and understanding that success at work doesn't mean shit if everything at home is falling apart.
I think that's what separated him from a lot of bosses I've worked with over the years. He understood that people don't leave their personal lives in the parking lot when they come to work. Every employee is also someone's spouse, parent, son, or daughter. They bring their entire lives with them, whether we like it or not. I know people always say “leave your baggage at the door” but that is just not reality.
Leadership isn't just about setting goals, managing budgets, or making difficult decisions. Like, no shit, those things matter, but they're only part of the job. The leaders people remember are the ones who genuinely care about their team, not just the position they happen to hold. To me, leadership starts with caring about people first. This was taken directly from my speech.
Understanding Doesn't Always Mean Agreement
I want to be clear, I didn't always agree with his decisions. If you've worked somewhere for years, that's impossible. There were meetings where I walked out thinking, "Are you fucking kidding me?"
The difference is I understood why.
I was fortunate enough to have a seat at the table where decisions were explained instead of simply barked at us. That changed everything. I still disagreed sometimes, but it never turned into resentment because I understood the context.
Guys, that’s important. When you explain a decision, it doesn't always become a decision people agree with, but it will be easier for people to accept. Context creates understanding.
Help People Become Better
Writing the speech made me think a lot about my own career and life.
I hope my kids remember that I showed up. I hope my wife remembers that I never let work or anything for that matter become more important than our family. I hope some dumbass I worked with says I believed in them before they believed in themselves.
Eventually every title disappears and someone else gets your office.
So that’s the theme I went with in my speech. It wasn’t about all the cool shit he accomplished. I talked about all the people he helped become better.
Thank You
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