Leading like you

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A little humanity

A black and white photo of a commuter train.

Last year, I started doing something unexpected at work: Hosting a weekly tea time.

A fair number of us come into the office regularly, but don’t actually work on the same projects. We sit near each other, sure, but just end up joining different Zoom calls with colleagues in other parts of the world.

I wanted to start tea time as a way to build community. We step away from the work and talk with each other. I make tea for anyone who wants it, but people who don’t drink tea come just to spend time with everyone.

#18
February 18, 2025
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The human need to be heard

Season 2, volume 1: Teaching by listening

This newsletter kicks off our new season on teaching. Each volume, we'll explore new skills and ideas to help you create great learning experiences for other people.

Let's talk about what it means to listen when you're teaching. From the student's perspective, this is about being heard. But what does it mean to be heard? What does it feel like when someone hears you?

#17
December 5, 2024
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What do you want to teach other people?

A pattern of wood in a sculpture in Lincoln Park, Chicago.

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:

#16
July 11, 2024
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Finding joy in who you are

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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."

#15
March 5, 2024
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The muscle in the middle of my body

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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.”

#14
January 23, 2024
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You get me

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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.

#13
November 30, 2023
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It's OK to say something nice

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Vol 10: Leading with encouragement

We all know it feels good when someone encourages you.

Or do we?

#12
October 26, 2023
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There’s no shortage of great leaders

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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.

#11
September 20, 2023
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Sometimes waiting is the hardest part

A pier with chains around it sit in a shaft of light in the Chicago river.

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.

#10
May 30, 2023
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Telling the truth about how you feel

A person sitting next to their bike in the park, looking into the distance.

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.

#9
April 30, 2023
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Telling the truth about how you feel

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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.

#8
March 14, 2023
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Acting on what you see

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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.

#7
February 7, 2023
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Ever heard of Fat Bear Week?

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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.

#1
December 28, 2022
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Being proud of who you are

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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.

#2
October 31, 2022
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Taking time to think

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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.

#3
September 30, 2022
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It's hard not to notice someone who gives

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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.

#4
August 24, 2022
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More than telling people what to do

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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.

#5
July 20, 2022
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Strong leaders? How about caring leaders

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Vol 1: Leading is for everyone

Hi, all. I’m starting this newsletter to explore leadership, but I never expected to. For me, the idea of being a leader used to bring up images of cheesy seminars and shallow airport books written by rich people.

If you’ve ever felt that way, I want you to know this is different. I’m here to empower you and change your perspective. And folks, our perspective really needs to change.

There’s a pervasive view that being a leader is about hierarchy. It’s grounded in the corporate world, which conflates leadership with management. The higher you make it, the more of a leader you are.

When I got my first job in tech, I was so excited. A few years out of college, I was making enough money to cover rent, food, and the things our newborn daughter needed. People talked about the “leaders” (managers) in the company with such awe. Co-workers said they were so smart, and that we were really lucky to hear their thoughts—especially the CEO.

I clearly remember an interaction with him that changed everything. This guy had a reputation for relying on fear and power dynamics to control his employees. Teams would review their work with him, and he would regularly lose his temper—screaming at the people presenting. No one wanted to be on their other end, but somehow, it just kept happening. We all needed to keep our jobs, right?

One afternoon, it was my turn. I’m a writer, and we were looking at some messages I’d come up with for new features. He found one he didn’t like.

“This doesn’t make any sense! What were you thinking?!”

As I stumbled over my words trying to explain why I’d written it that way, he found a mistake I’d made, where I said “less” instead of “fewer.” I should have caught it before, but there it was. He began yelling even louder.

“Who are you? How did you get a job here? You’re an idiot. Where’s the other writer?”

I honestly don’t remember much after that. I couldn’t think straight. Here’s what I know: None of the other 20 people in that meeting called out his behavior. They just listened. My manager told him I’d work on some revisions, but didn’t stand up for me in the face of all that verbal abuse.

I hung up the call, then cried for the next 30 minutes while I walked around my neighborhood.

When we think of leadership as a hierarchy, we end up approving of these people, implicitly or explicitly. We end up excusing abusive behavior. And we end up with way too many White men occupying our mental images of leadership—a group I’m part of, but certainly not proud of. No wonder the topic of leadership can feel so uninspiring.

This unhealthy view of what a leader is hurts everyone. It causes us to celebrate LinkedIn profiles and profitable companies, when we should really be celebrating character, thoughtfulness, and kindness.

Real leadership would have been for someone else in that meeting to stand up for me. It would have meant ignoring the power dynamics and telling this CEO that what he did was wrong. To use the phrase Brene Brown made popular, it would have meant choosing courage over comfort. One of the leaders I look up to most, Vivianne Castillo, uses these words all the time.

Leading is for everyone. It has nothing to do with a job title or role. You don’t need a promotion to be a leader. In fact, you might already be one to the people in your life. It’s a skill that helps you bring others together and accomplish amazing things. But you get to choose how you do it. You can lead with love, humility, kindness, hope, humor, generosity, and so many other things.

Each month, we’ll explore how to find a way to lead that reflects who you are and how you want to show up in the world. I'll share different methods you can try and perspectives from leaders I admire, so we can all expand our view.

Anyone can be a leader. No one can lead like you.

Real leaders: O. Hanna Badmus

A photo of O. Hanna Badmus.
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Each month, I ask a leader in my own life to share who they are and what leadership means to them.

Hanna describes herself as an advocate and advisor. A daughter, sister, and friend.

Here’s how Hanna thinks about leadership, in her own words:

I am a firm believer in leading by example; I would not ask my team to do something that I wouldn’t or haven’t done. I believe as a leader you must be approachable and vulnerable because to me, that creates a trusting relationship which allows folks to be creative without fearing judgment. Last, while the work we do as leaders is really important, it is important to understand the people you are working with. What motivates them? What is their why? When you know this, you can speak in the language they will respond to. You’ll also be speaking to the whole person versus the outcome you hope to achieve.

Many thanks to Hanna for sharing her story and perspective.

#6
June 14, 2022
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