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Mistakes I made as a Manager

Manager Mistakes
Manager Mistakes

For most of my career, I was in a technical role—the go-to person for solving tough problems. That all changed when I was given the opportunity to build a new department and lead a small group of technical staff that eventually grew into nearly 40 people across three separate specialized teams. Transitioning from being the hands-on expert to stepping back and leading others wasn’t easy. It’s a shift in mindset, and one of the hardest parts is setting the boundaries that come with leadership.

I definitely stumbled a bit early on. I made some mistakes, but I learned from them—and I want to share a few of those lessons with you.

Be friendly, not friends

When I first stepped into a leadership role, it was a bit tough. The people I was now managing had been my peers, and I figured, “Hey, we’re friends—this should be easy.” But it didn’t quite work out that way. Being friends with the people you lead can blur the lines. You need clear boundaries, and friendships can make that tricky.

I had one employee I’d worked with for years as a peer. At first, it felt great—we kept things friendly even though I was now his manager. But I made the mistake of not setting clear boundaries or redefining our relationship early on. When I eventually had to step in and actually manage him, things got increasingly difficult. It turned into a months-long situation that could’ve been avoided if I’d handled it differently from the start. That may not be your experience, but I was lucky to learn that lesson early on with a relatively small team—and I’ve never let it happen again.

Another thing to keep in mind is how things look to others. If you’re close with some team members and not others, even if you’re being totally fair, it can come across as favoritism. That perception alone can cause problems and disturb team dynamics.

At the end of the day, your team doesn’t need you to be their buddy. They need you to be steady, empathetic, and willing to make the tough calls when it counts.

Step Back

Transitioning from a purely technical role into a leadership position means stepping back from what you know and diving headfirst into something completely unfamiliar—at least, that’s how it felt for me. Instead of just managing myself, I now had to lead others. And like many people, I found myself constantly drifting back to what was familiar. In my case, that meant still working on designs, reviewing technical specs, and staying deep in the weeds.

But if you keep doing that, you won’t have the time or space to focus on what your team actually needs from you—things like building the department’s brand, showcasing the team’s success to executives, developing strategies for growth, building the necessary structure and processes, and so on. Sure, there will be times when you need to jump back into the technical details, and that’s okay. But if it becomes a habit, the people you hired to do the work won’t feel empowered to own it. And without that sense of ownership, the trust between you and your team won’t have a chance to grow.

Avoiding the hard conversations

It’s never fun when someone on your team isn’t meeting expectations—whether it’s performance, behavior, or anything in between. The natural tendency for many leaders is to ignore it or avoid addressing it directly, hoping it’ll just work itself out. But that approach only plants the seeds of chaos in the department. When issues go unchecked, it undermines morale and creates confusion about what’s acceptable.

I’ve always felt uncomfortable having those tough conversations, but I’ve seen firsthand what happens when they’re avoided—team dysfunction, frustration, and a breakdown in trust. So I made the decision to face it head-on. It wasn’t easy, but it was necessary. And over time, I’ve learned that dealing with problems early and directly is one of the most important things you can do to protect your team’s health and culture.

Leadership’s a journey, and these were some of my first steps. Thanks for walking through them with me. Until next time!