Welcome back, visionaries. Today, I’m going to share a different kind of story…not a story of success, but one of failure and lesson-learning. Let’s talk about why building a team is the most difficult thing you’ll ever learn to do.

The Learning Curve of Building a Team

I wish all the time that my dad—who was also an entrepreneur—was still around when I first started building a team. I had no idea what the hell I was doing; I had no idea how to be a boss, period, much less a good one. 

When I first started, I dreamed of having those late-night conversations at the kitchen table back, sharing a bottle of wine like we used to do when I was in high school. (Don’t panic—I’m from Switzerland, and it’s totally allowed there.) When I first started building my business and my team, I wanted so badly to ask him how to handle all the flat-out crazy things that happened with my team early on.

I could really have used some real-life advice on building a team: what to say, what policies to put in place, and how to respond to things rather than react.

I was 29 years old, a budding entrepreneur with a very fast-growing company, and my dad had been gone for eight years already. Like so many CEOs, I learned about building a team and how to CEO on my own from failure after failure. Leading a team—and doing it well—has by far been my steepest learning curve in business.

Building a team and learning to be a good boss was far more challenging than getting clear on my messaging, creating an awesome offer, or learning how to bring in clients, market my business, and deliver amazing results to our clients. None of that even vaguely measured up to the learning curve that came with building a team. 

Thinking back to some of those early floundering decisions makes me literally cringe to this day. But truth be told, I just didn’t know what I didn’t know. I did the best I knew how to do.

Though I support my clients through some pretty hairy situations today while they’re building a team, it’s all done behind closed doors, so all of you out there don’t get to see much of that process. Honestly, we don’t talk about this stuff enough, or give each other enough support around the crazy, wild ride that becoming the boss can be. 

None of us are trained on how to become a boss, how to be a leader, or how to support and manage and lead a team. 

I’ve been thinking about this a lot lately, because I’m watching my clients going through some pretty wild situations right now, and it’s making me think back to my old way of building a team and how challenging it was.

All that to say, I believe it’s about time that we start talking about our failures, challenges, blunders, nightmares, whatever you want to call them…and I am happy to go first. 

The Day I Fired My Whole Team

There was a time when I fired my whole team on the same day.

Yes, you read that correctly: my whole team, all at once.

It all started with my team coming in on a Monday morning giggling and gossiping about one of our clients that had attended our live, in-person event that past weekend.

So it turns out that after I went home on Saturday, one of our clients—a married guy with a couple of kids and a wife at home who had traveled up to our area and stayed in a hotel—had invited one of my team members out for drinks. All three of them ended up going with him; drinks led to dinner, and dinner led to heading back for a swim in the pool at the hotel where he was staying.

But before the swim, they decided to party it up even more when one of my team members pulled out a joint. 

Yes, again, you read that correctly. Even in the early 2000s, California was very 4/20 friendly.

To top it all off, before the night was over, my team had playfully—or so they said—pushed my fully-clothed client into the pool.

My three twenty-something-year-old team members, all women, thought the whole thing was hilarious. But the more of the story I heard, the more uncomfortable I got. 

It wasn’t like they were trying not to tell me. They were just gossiping among girls. But as an inexperienced boss, I wasn’t sure what to do. I ended up playing along in the friendly chatter, even as the pit of my stomach was churning. 

Later that day, I went out to my car and called my mentor to ask him what I should do.

The whole thing had made me think about the comment my mentor had made the month before, after I’d brought my whole team to one of his events. I had excitedly asked him, “What do you think of my team? Aren’t they great?” And his response was, “You sure seem to be having a good time together.”

As I was sitting there in my car, I suddenly understood why he hadn’t gushed all over my team or given me the good-job pat on my shoulder that I had been after. My mentor had seen something that I, in my inexperience, just couldn’t see. I was way too friendly with my team. I had traded being their boss for being the cool boss, the friendly boss, the boss everyone loved. 

So the next day, I pulled my team leader aside for a sit-down, letting her know that smoking weed with clients was not something we did, nor was pushing our clients into pools fully clothed. I remember looking at her and asking, “What were you thinking?”

Instead of apologizing, she started talking really fast, explaining it all away as fun among adults with a slightly annoyed tone. She was very dismissive. “It was non-company time. We can do whatever we want in our free time. He had such a good time with us. He was the one that wanted to smoke.”

That was when I finally realized it was game over. My team had lost all respect for me. 

What Next?

Now, this little incident was not the only thing that showed me their lack of respect. There had been many signs along the way: showing up late, missing deadlines, ghosting the weekly team meetings, handing in sloppy work, calling in sick on a Friday…the list went on. 

But this conversation with my team lead was when I finally got it, and I knew what I had to do. 

I went back to my car, called my payroll service, got the final paycheck for all three of them, wrote up the checks, and handed them out at the end of the day with a “See you later, alligator.” And then I sat down at my desk in a very quiet, very empty office, and wondered…what now?

This was part one of this series all about building a team and learning how to be a boss. I’m going to continue sharing the lessons I’ve learned about building a team with you over these next couple weeks, so stay tuned for that. But for today, I want you to start by sitting down and really asking yourself, are you actually in charge of your team? Or have you been trading in your authority in order to be the “cool boss?”

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