You Can’t Win Everyone Over

On criticism, ego, and the conversations that come too late.

Note: All of these are real events and conversations, so names have been changed for privacy.

Los Olivos, CA. Photo Credit: Colin Black

What do you do when one of your employees tells you they’re unhappy and want to quit?

Do you get defensive?

Do you listen to them and try to change?

Do you accept that they might never be happy and just let them leave?

Do you blame yourself? Do you blame them?

Or, do you accept that the truth probably lies somewhere in the middle?

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Back in 2016, I was managing an online high school program. We were sort of a startup and sort of a spinoff of a larger education-focused law firm.

Somehow, by some miracle of networking powers I didn’t know I had, I managed to arrange a two-week trip out to California to go to a conference and meet some of the 80–90 teachers we had working remotely.

At the time, I was in the middle of trying to build a high school curriculum from scratch.

To accomplish this goal, I had a giant spreadsheet of every teacher, listing all the courses they’d previously taught.

The reason?

I had hired some people for one job, hoping to train them and get them to take other jobs 2–3 years later. For example, I hired several people to teach English 1 and 2. But some of them had previously taught multiple higher-level history and English classes.

So, the goal was simple: hire them to teach a lower level class and then ask them to develop or teach the higher level classes once they knew how our company worked.

None of the teachers knew about this spreadsheet. That’s probably a good thing.

Why does this matter?

Well, when I went to California, I had to meet with one teacher named Laura who we’d hired to teach English 1. What I wanted her to do was develop and lead English 2 and 3 courses. She had great camera presence, strong leadership skills, and detailed knowledge of all the relevant subject material.

Plus, I thought we got along really well.

We met for dinner with her husband in Los Olivos, California. I remember the air was cool and the sunlight was hitting the olive trees and oak trees just right. Somehow, even though we weren’t that far from L.A., the town reminded me of a wild west town.

It was picturesque. I wasn’t ready for a difficult conversation.

Sometime about 20 minutes into dinner, Laura told me she wanted to quit.

Cue the gut punch.

She was unhappy with the technology, unhappy with the pay, unhappy with my leadership, and burned out.

Now, obviously, I could have developed the classes without her. I had a pretty deep bench of teachers to choose from.

But she was one of the best.

I had a plan. And this was messing up the plan.

Even worse, I hate people being unhappy with me.

I remember feeling out of my element.

I was 23 years old, managing nearly 100 people. And I felt like I had no idea what I was doing.

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Los Olivos, CA. Photo Credit: Colin Black

Before I resolve that story, I want to share one more similar scenario.

I had another employee, Julie, in the office. I think this was a few years later in early 2018, before I started grad school that August.

Like I said, we had about 90ish teachers who worked remotely, and we had a team of 7 or so in the office, where we worked alongside our parent organization.

When we hired Julie, everyone really liked her. She was fun, smart, and easy to get along with. She ended up working on teacher support projects, like reviewing curriculum, dealing with student discipline issues, and organizing content in our online learning management system.

The year Julie joined was a rough year.

It was my last year in the office, because I was going to grad school. My first hire and right-hand guy, James, was also leaving that year. So we were about to lose a ton of institutional knowledge.

In the meantime, we were trying to develop 10 new courses that year, redesign the website, hire a huge number of teachers, and migrate to a new learning platform.

The issue? Our old learning platform was so antiquated, it had no API plugin to migrate everything automatically to the new platform.

This meant every single quiz question, PDF, video, and link had to be moved by hand. We’re talking thousands and thousands of pieces of content.

It took about 8 or 10 months, while the whole team also worked on everything else involved in running a school.

I remember one of the breaking points.

I asked Julie to review the recordings of our live class sessions and try to find 5 min. clips from each of our main course categories (literature, math, science, etc.) to use on our website as samples.

The idea was that putting more free content online would save us from dozens of repetitive phone calls and emails asking to see examples.

For Julie, this meant spending about an entire week or two watching hours of classes trying to find good clips.

As I’m writing this, I’m painfully aware that now this could be done in minutes or seconds by AI.

But this was back in 2018. AI wasn’t an option.

I remember her asking me if she really had to do this project, and I told her that it would really help the team. I encouraged her to do it in small chunks, take breaks to work on other projects, and do fun things like going on walks to give her brain a rest.

Even so, I could tell she was getting frustrated.

I honestly couldn’t tell you if it was this week, or some other time when the incident happened. But I know if it wasn’t that week, it was definitely sometime around then.

Her boyfriend, who worked on the other side of the building as a legal assistant, came into my office and started chewing me out.

Not quite yelling, but pretty close.

The issue was that Julie was burned out and hated her job, but she didn’t have the heart to tell me. So he took it upon himself to tell me for her.

I remember being pretty concerned but also having a hard time not laughing, just because the situation was so ridiculous and unprofessional.

Some moments are so bizarre, they don’t feel like real life.

I ended up telling him that we’d have this argument in front of HR. (Ah, the benefits of working in a small office). Thankfully, HR took my side and he backed down.

But when I talked to Julie, I learned the truth.

She absolutely hated her job. She thought I was a bad boss, and she was planning to leave in about a month or two.

I asked her if she’d had any intention of telling me how upset she was before she left, and she said no. She was just planning to coast and get by for the next month and never tell me.

I remember saying, “You know, if you’d told me how upset you were months ago, I probably could have changed something to make things better.”

She said she knew that, and she didn’t really know why she didn’t say anything.

I guess she was too scared to have that conversation.

Ugh. Another gut punch.

No matter how many books you read on leadership, some lessons you only learn by living them.

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Solvang, CA. Photo Credit: Colin Black

So, what happened in the end with Julie and Laura?

Well, Julie stayed true to her word. She left soon after that incident, got married to her boyfriend, and they became farmers. Sounds odd, but that’s what really happened.

Laura stayed.

In fact, she actually stayed about 4 or 5 more years, even after I left. She built English 2 and 3, joined a special committee to choose a new tech platform, and led her teams like a champ.

Same company. Same boss. Different outcomes.

So what was different?

Part of it was timing. Julie told me too late for me to do anything. Laura didn’t.

Part of it was the willingness to communicate. Julie avoided conflict. Laura wanted to have a dialogue.

Part of it was clarity. Julie gave me a general sense of being unhappy. Laura gave me a list of specific things I could fix.

Part of it was the environment. Julie worked with me in the office and saw me every day. Laura worked 3,000 miles away from me. Sometimes distance makes things easier.

Part of it was my leadership.

With Laura, I ate some humble pie, accepted her feedback, and tried hard to change things.

With Julie, it was different.

In the office, she’d seen a year of me being stressed, tense, and defensive.

I was stressed about giving up control and going to grad school.

I was overwhelmed with developing 10 new classes, migrating platforms, redesigning our website, and interviewing 300 potential teachers.

I was anxious about multiple people telling me my program should be cut to save money.

I was young, and I was still learning how to lead.

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When you compare how I handled things with Julie and Laura, nearly a decade later, I still don’t know exactly what went wrong or how I could have brought about a different outcome.

I may have simply burned Julie out by assigning too many boring projects that year.

Even though I tried to encourage Julie, and I tried to include her in important conversations about teacher performance and curriculum design, I’m not sure I made her feel enough like an owner.

Looking back, I think the key here is that I didn’t just present a solution to Laura.

I invited her to help build the solution.

I tried to do the same thing with Julie, but somehow it didn’t resonate with her the same way.

Maybe it came too late. Or maybe it just felt like more work, not something meaningful to her.

I still think there’s something to this.

You can’t just make someone feel welcome. You have to make them feel important.

And one of the best ways to do that is by inviting them to build something the company really needs.

But even that doesn’t always work.

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Huntington Beach Pier, CA. Photo Credit: Colin Black

I wish I could tell you I was a great boss. I don’t know.

Some people cried when I left. Others just tried to wait me out.

But some people stayed at that company almost 20 years, joining long before me, and staying long after. That gives me hope.

And in the end, we turned around a company making a 10% annual deficit for 6 years and brought it up to a 12% annual profit.

A group of 20-year-olds essentially built a school from scratch.

I’m still proud of that.

All I know is this: the hardest part of being a leader isn’t building a product, a brand, or a business.

It’s building a team.

Sometimes you turn a critic into an ally.

Sometimes you get yelled at by someone’s boyfriend in your office.

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Want to read more like this?

Here’s one of my favorites:

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