What’s next for Leading Like You

Hey, everyone. It’s been a couple of months since you heard from me, and that’s because I’ve been working on what’s next for Leading Like You. Today, I’m excited to share it with you.

Before we get into that, I just want to celebrate what has happened so far. I wrote the first newsletter in June of 2022, more than two years ago. In it, I shared a painful story from my career that illustrates why I care so much about challenging the popular conceptions of leadership. Here’s an excerpt:

Vol 12: Leading while loving yourself

Have you ever dealt with someone who seems overly confident? Some of my most difficult work situations involve people who are incredibly sure of themselves, as if they can't make mistakes. These folks seem unable to hear about new evidence or change their minds. Conversations with them can be draining and demoralizing.

Once, I was trying to convince a person like this that we shouldn't build a software feature they were requesting. I thought it was going to be an easy conversation. I had evidence that our users didn't need it, data showing how it wouldn't help our business, and rationale showing how much time and money it would waste. I was so surprised when that person, despite hearing all this, insisted that we would be doing it anyway. "Wow," I thought to myself, "I wish I had that much self-esteem."

Vol 11: Leading with acceptance

It’s been about a year since I started noticing strange things happening with my heart. Not the metaphorical center of my emotions—the muscle in the middle of my body. Is it wise to write about a health problem on the internet? I guess I’m about to find out.

It started with my heart racing when it shouldn’t have, like when I was just sitting around or standing. I also began to notice my heart pounding, along with chest pain. I went to the emergency room twice, because all the guidance out there around chest pains is basically “it could be nothing, or you could be dying, so go to a hospital.”

Vol 11: Leading with understanding

Have you ever found yourself thinking about someone else and saying "I really like them... They get me." It's something we say all the time, but what does it really mean? What's the other person doing that gives you that feeling?

When someone gets me, it feels amazing. They make me feel safe and appreciated. There's no need to change who I am or act differently around them.

Vol 10: Leading with encouragement

We all know it feels good when someone encourages you.

Or do we?

Finding ways to be free

It’s time for reflection again.

First off, thank you to everyone reading this. It’s been over a year since I start writing publicly about leadership and sharing perspectives from leaders I admire. Since then, more than a thousand of you have signed up to hear more, dozens of you have attended workshops or talks I’ve put on, and I’ve heard from more people than I can count who feel energized by the idea that leadership isn’t the same as management or hierarchy. That’s amazing, and I’m celebrating that today.

Vol 9: Leading with endurance

Some years back, I had a rough experience starting a new job.

New jobs are strange, right? There's so much joy and excitement from going through that journey, interviewing, and finally finding one. I was excited. It included a pay raise, and the project sounded exciting.

Vol 8: Leading by making it through

Recently, we’ve been hosting community dinners at our home. We invite people over to enjoy some food and build connection with each other. It’s a time of peace and spiritual exploration. One of the things that came up last night is the idea that often, we have such high standards for ourselves, that we expend absurd amounts of mental energy on feeling like we aren’t doing things well enough.

One person mentioned something he keeps in mind: The idea that just making it through a situation is something to celebrate. That’s success.

Vol 7: Leading with honesty

One of my first lessons about honesty in the workplace came when I was working at a tire shop after college. The manager was running a sale where customers could buy three tires, then get the fourth one for free. I remember it because he asked me to put plastic letters that wrote “BUY 3 TIRES GET 1 FREE” up on both sides of the sign in front.

The first time I sold a customer this deal, I added four tires to their order, then zeroed out one of them. They loved the price and left happy. Then, the manager saw the invoice. His reaction was strong. “Why would you do this? You can’t just give tires away!” he asked, as if I had just tried to make coffee in a washing machine. I told him I was just following the deal on the sign. He told me the way this deal worked was that we had to increase the price of the other three tires a bit to cover the cost of the fourth. This is when I learned that most deals are artificial. Capitalism isn’t just going to give things away, it will protect its costs. It felt like a lie. Maybe it was, even if the customers were seeing the increased costs of the other three tires up front and agreeing to them.

Vol 6: Leading with compassion

Maybe the industry I work in is a weird one (well actually, I’m fairly certain it is) but we talk about empathy all the time. Empathy for each other and empathy for the people we’re designing for. It’s not a bad thing in itself, but it’s to the point where many people are more interested in being seen as empathetic than in actually doing anything different. It’s a bit of a trap.

That’s why I prefer to focus on compassion. To me, compassion is about action. A compassionate person sees what people around them need, then does something about it.

Vol 5: Leading by living

Have you ever heard of Fat Bear Week? It’s an incredible, March Madness-style tournament designed to find the fattest brown bear in Katmai National Park, Alaska. It’s a showndown between once-scrawny bears who have been hard at work eating enough to sustain them through winter hibernation, and the public votes to decide the champion.

I found out about Fat Bear Week from a former co-worker, Haley. She was part of a team I managed, and she got us all hyped up to participate and vote. We had Slack threads filled with bear banter and incredibly polite trash talk. Each day she’d give us an update, and her excitement was contagious.

We’re approaching 6 months of this newsletter project, and I’ve gotta say, I’m so grateful for all of you. Lots of people have written back, sharing their own stories and what resonates with them. Others have mentioned it when they see me in person, talking about the encouragement they’ve found. If you are one of those people, thank you. It means so much, and it shows me that this idea of leadership being more than a job title or a slot in the corporate hierarchy is worth exploring.

I’m taking a break from the usual format this month to share something I’ve been thinking about. Recently, I got to give a keynote on leadership at a conference called Button in Seattle. An example I gave in the talk was how at one point in my career, I had to work with a really tough person who was senior to me and often just ran right over my ideas. It felt like nothing I could say would get through to him.

I was at this job for two years. I tried a lot things, made a lot of progress, but still never felt like I really got through to this person. Then, six months after I left the job, he sent me a text message. In it, he said that he used to resent me, but that now he sees that what I was doing made sense, and that he champions the values I was advocating for every day.

Vol 4: Leading with thoughtfulness

A few years ago, if you would have asked me if I’m a thoughtful person, I would have said yes. I’m someone who wants to think things through and understand them. I enjoy researching new topics. I love solving problems. So yeah, I thought I was thoughtful.

Then I met Daniel, someone who redefined what thoughtfulness means to me.

Vol 3: Leading with generosity

One of my first jobs after college was working for my father-in-law, Jose, as a salesperson. He owned an auto repair and tire shop at the corner of 45th and Ashland on Chicago’s south side. It wasn’t what I expected to be doing, but it was a tough job market (especially for folks in creative fields like me), so I was grateful to have a job at all. I learned about sales techniques, practiced customer service, and got to know every corner of the city as I drove around picking up parts for our customers’ cars.

I also got to spend more time with Jose, and I learned about who he is and the way he leads. One of my earliest memories is how he treated people who stood at intersections and walked down the rows of cars when they were stopped, asking for money. He kept a stash of bills above his visor so that he was always ready to help them out, and he never hesitated. It’s been thirteen years since then, and I’ve seen him continue to give to people in need any chance he gets.

Vol 2: More than telling people what to do

In a culture that glorifies hierarchy (like the one I grew up in here in the United States), one of the worst things people are taught about leadership is that it’s same thing as authority.

This gets into our heads at an early age. When I was out to breakfast with my two children recently (ages 9 and 11), they asked what I was doing the rest of the day, and I said I was working on this newsletter about leadership. I asked what they thought it means to be a leader.