Every Leadership Interaction Leaves a Legacy

A boat moving through water leaves a wake, and the wake reaches the shore long after the boat has gone. Leaders do the same thing. Every conversation, decision and reaction leaves something behind in the people who were there. Add those moments together and you have your leadership legacy. It is written one interaction at a time, mostly on days you will not remember.

So the second question I ask leaders is this: do you leave a positive wake?

Every experience is emotionally framed

We have a visceral reaction to whatever happens to us. Your team may forget the third bullet on your slide, but they know how they felt when the meeting ended. People walk away from you stronger or smaller, trusted or questioned, energized or depleted. In every encounter your life leaves an impact, and it is either positive or negative.

I think of it as the difference between being a wellspring of life and being a drain. We all know people who make us want to duck and cover when we see them coming, because we know how the conversation will go. The weather is terrible. My kids don’t love me. My bunions are killing me. Can you believe what they’re asking me to do now? They are the Eeyores of life. You remember Eeyore from Winnie the Pooh: life is full of thistles, so you may as well be sour about it.

It is easy to name the Eeyores you work with. It is harder to ask which one you are.

Why your wake shows up in performance

One of the ways I define culture is people’s emotional attachment to the work experience. By that measure, a lot of cultures are in trouble. Gallup reported that in 2024 only 31% of U.S. employees were engaged at work, the lowest level in a decade, and 17% were actively disengaged. That leaves about half the workforce showing up, doing what is required and living for the weekend.

Picture what would change if your leadership moved some of those people from the middle group into the top one, without changing anything else about the business. That opportunity sits in front of every leader, and it starts with the wake you leave.

Sometimes, as leaders, we don’t slow down long enough to smell our own exhaust. We need to.

The hugs matter more than the food

I like to show audiences a short film about Tim Harris, who owned a restaurant called Tim’s Place. Tim has Down syndrome, and he greeted the people who came through his door with a hug. In the film he says his restaurant serves breakfast, lunch and hugs, and that the hugs are the best part. “The food is food,” he says.

I love that, because it applies well beyond restaurants. Whatever you sell, at the end of the day it is just the food. The hugs are what make you special: how people feel after they have dealt with you. (Before your HR director calls me, I mean that as a metaphor.) Find a way to make someone’s day, every day.

The good things are a byproduct

There is a principle underneath this that I call the maxim of positivity: all the good things you want in life are a byproduct of creating value for others.

Take happiness. Everybody wants it, and it is not something you can chase and grab. Ask people what one thing would make them happy and most will say more money. Give them that amount and they want more. They are chasing the wind. Sir John Templeton observed that happiness pursued eludes us, while happiness given returns. I am happiest as a husband when my wife is happy, and happiest as a team member when my team is happy. Happiness is something you create, which is the subject of my book Fireproof Happiness.

It works the same way in business. Chick-fil-A, an organization I have had the privilege of working with, says it wants to be the world’s most caring company. What does that have to do with selling chicken? Nothing, and everything. When you care for customers, they become raving fans, and raving fans tell other people.

How to check your wake

You cannot see your own wake from the driver’s seat. Somebody on the shore has to tell you. So ask, and then listen, which leaders rarely do. Here is the question, if you are bold enough to use it:

What is it like for you to be on the other side of me?

Ask it of your spouse, listen intently, and your spouse will tell you everything they need to thrive. Ask it of your kids and they will tell you what you need to know to be a great parent. Ask your clients a version of it: what is it like to have me serving your account, and what could I do better? Then resist the urge to explain yourself. The lost art of leadership is asking good questions before you jump to conclusions.

Two smaller habits help between those conversations:

• After an interaction, ask yourself what kind of wake you left.
• At the end of the day, ask whether your presence made the people and situations around you better.

A positive wake is the second of three questions I teach. The first is whether you create more value than you take, and the third is whether you solve problems or assign blame. If you want your leaders to work through all three together, that is what The Remarkable Leader keynote is for.