Published in Leadership

Jonathan

The Effective Project Manager

June 30, 2025

What Makes a Leader Worth Remembering?

A reflection on leadership, connection, and missed opportunities. This personal essay explores what makes someone worth celebrating and how thinking about what was missing can reveal what great leaders do differently.

I begrudgingly went to a farewell for a senior leader at my company. Someone I directly reported to for five years. I really didn’t want to go. I was thinking about the reasons why I didn’t want to go and why it frustrated me.

Why didn’t I want to celebrate them at their farewell? It’s not because I hate them or because I think they’re a bad person. It’s just because they did nothing for me.

It’s not part of the job title to do good things for people. It’s not a requirement to lead them, try hard for them, or teach them.

But it would have been nice.

The more I thought about it, the more I realized this is how you reverse-engineer a leader. You think about the things they didn’t do, and wish they had.

I don’t remember him ever telling me, “Good job.” Maybe he did once or twice in the last five years, but I don’t think so. I don’t think he ever praised my abilities. I don’t recall a single teachable moment. I don’t think he ever said, “This is what I learned from my experience, and here’s how you can apply it to yours.”

He never gave me any heuristics, shortcuts, or tips and tricks. He never reviewed my work and said, “This is good, and this is bad.” Very, very occasionally, he gave feedback. And by very occasionally, I mean once every few months. When he did, it was clinical and to the point.

I don’t think he ever showed empathy. Maybe once, when I told him about something difficult happening in my life, he expressed a bit of it. But other than that, no.

I remember one difficult situation with him. He thought I wasn’t completing my work properly, and he let it boil over. He spoke about it in vague terms, without being direct. Then one day, he just exploded with rage, which brought me to tears in front of him and another senior leader. That was one of the low points of my career under him.

How to be a good leader

When I think about how to be a good leader, someone people celebrate, I don’t think it’s that difficult.

  • You need to put effort into people.

  • You need to encourage them.

  • You need to empathize with them.

  • You need to share a bit of your own life, thoughts, and feelings.

  • You need to encourage them to share a bit of theirs.

I realize this is easier with people you like, and harder with people you don’t. I find that in my own work too.

With people I like, I naturally do those things. With people I don’t like, I naturally don’t.

So perhaps he was a good leader to others. People he liked more. People who connected with him and his style. But I think part of being a good leader is making an effort.

You’re not going to connect with everyone in the same way. But everyone you are called to lead should feel some connection to you.

That’s what I take away as my own leadership goal. I’m going to try to connect more with the people I don’t naturally connect with on a personal level.

It’s sad when someone leaves and you don’t want to celebrate them. But that happens to all of us. We need to examine why that is, and try to improve.

If I left, would anyone cry? I really hope not. But would anyone be a bit sad that I was leaving? I think a few people would. And I should try to do more to make sure more people feel that way. Not because I want to be celebrated, but because I believe it’s a sign that I’ve done a good job.

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