Over time, leadership simplifies. Not because it gets easier—but because the lessons get clearer—especially when facing change.
Here are a few truisms about change that have stuck with me over my years of coaching successful leaders.
1. Don’t Expect “You” from Anyone Else
When you’re choosing a successor—or evaluating anyone coming behind you—remember this: They are not you. Founders and early leaders often build something through sheer force of will—guided by grit, instinct, hustle, disruption, and a relentless drive to win. That’s what it took to get the business off the ground.
But version 2.0 isn’t about force. It’s about scale, systems, process and repeatability. You simply can’t scale tenacity. And you shouldn’t expect the next leader to lead the way you did. If you do, you’ll either frustrate them—or miss the value they actually bring to the job.
2. Everything Takes Three Times Longer Than You Think
This one is simple and painful. Strategy. Change. Hiring. Culture shifts. Turnarounds. All of it takes longer than you want—and longer than you’ll plan for.
You can fight that reality … or you can lead with it in mind. The leaders who last are the ones who adjust their expectations without lowering their standards.
3. If You’re the “Change Agent,” Prepare for the Fight
If you’ve been hired to drive change, don’t confuse alignment at the top with readiness in the system. The board may want change, but, chances are, the rest of the company does not. Not really. Not at all.
Change is disruptive. It threatens identity, power, comfort, and history. And even when people say they’re ready—they aren’t. Not until they have to be.
This job will be lonely, slower than expected, and way more exhausting than advertised. So, before you step into that role, ask yourself one honest question: “Am I up for the fight?” Because it will be a fight—a very long, hard, and lonely fight.
4. Act Sooner Than You Want To
A wise leader once told me: “The first time you think about terminating someone is when you should terminate them.” I’ve never forgotten that. Letting someone go is serious business so we wait, we hope, and we rationalize.
But deep down, we usually know what we need to do. And delaying the decision doesn’t help the person, the team, or the business. It just drags out what already needs to happen.
A Few More Bits of Leadership Wisdom That Haven’t Failed Me
- Loyalty is earned.
- Trust is earned, also.
- If things are going badly, you don’t have to fire everyone—just one. The message spreads.
- Play the long game.
- And one fun one that I still remember from an old Dilbert t-shirt: “Change is good … you go first.”
The Closing Truth
Change isn’t an initiative, it is not a program, it is not something you launch to check off. Change is the job. And the longer you lead, the more you realize you can’t control change, you can’t speed it up, and you can’t escape it. You just decide how you’re going to show up inside it.
My advice is to show up strong, clear, and on time when it matters. Because, in the end, leading through change isn’t about being right or being fast. It’s about being true long enough for the right things to take hold.