Neither Friends nor Servants: Lessons About Building Teams from a Young Agency Owner

I started my first agency at 26. By 28, I had fifteen employees, a handful of significant clients, and absolutely no idea what I was doing as a leader. I knew how to do the work — that’s how I’d gotten here. But managing people? Building a team? I was making it up as I went, and the lessons I learned cost me relationships, sleep, and in some cases, good people who deserved better.

This is a collection of those lessons. They’re not comfortable, and some of them still sting. But they’re true, and I wish someone had told me earlier.

Lesson 1: Your employees are not your friends

This is the hardest lesson for young leaders, and the one I got most wrong. When you build a company from scratch, the first hires feel like co-conspirators. You’re in the trenches together. You share meals, share frustrations, share the intoxicating feeling of building something from nothing.

But there’s a power dynamic that friendship can’t erase. You sign their paychecks. You decide their raises. You can end their employment. No amount of casual Friday energy changes that fundamental asymmetry.

I learned this when I had to let go of someone I considered a close friend. The conversation was devastating — not because of the business decision, which was clear, but because we’d both pretended the dynamic was something it wasn’t. The betrayal they felt wasn’t about losing a job. It was about losing what they thought was a friendship.

The lesson: You can be warm, genuine, caring, and deeply invested in your people’s success. But you are not their friend — you are their leader. These are different relationships with different obligations. Conflating them serves no one.

Lesson 2: Your employees are not your servants

The flip side is equally dangerous. Some leaders, having learned that employees aren’t friends, overcorrect into treating them as resources to be optimized. Headcount. FTEs. Human capital.

I watched myself do this during a particularly stressful growth phase. I stopped seeing people and started seeing capacity. Could this person handle one more client? Could that team work weekends to hit a deadline? The language of agency life made it worse — we talked about “utilization rates” and “billable hours” as if people were machines with a measurable throughput.

The human cost was real. Burnout. Turnover. A growing sense among the team that they were valued for their output, not their judgment. The best people — the ones with options — left first.

The lesson: People are not instruments of your ambition. They’re collaborators who have chosen to invest their time and talent in your vision. That choice is voluntary, and the moment they feel used rather than valued, the best ones will un-choose you.

Lesson 3: Clarity is kindness

In my early days, I thought being a good leader meant being nice. Avoiding confrontation. Softening feedback. Giving people the benefit of the doubt long past the point where doubt was warranted.

I once spent six months “coaching” an underperformer when what they actually needed was a direct conversation in month one: “This isn’t working. Here’s specifically what needs to change. Here’s the timeline.” Instead, I hedged, hinted, and hoped. By the time I finally had the honest conversation, they were blindsided — because my “kindness” had been lying to them for half a year.

Vague feedback is not kind. It’s cowardly. It protects the leader from discomfort at the expense of the employee’s growth.

The lesson: The kindest thing you can do for someone is tell them the truth clearly, early, and with enough specificity that they can act on it. Difficult conversations are a feature of good leadership, not a failure of it.

Lesson 4: Culture is what you tolerate

I used to think culture was about values on a wall, team outings, and the vibe of the office. It’s not. Culture is the set of behaviors that are tolerated and rewarded in practice, regardless of what’s written in the handbook.

I had a brilliant creative director who was also, privately, a bully. They delivered exceptional work and terrorized junior staff. I knew about it. I told myself it was “just their style” and that the work quality justified the behavior. It didn’t. By the time I finally addressed it, three good people had already quit — not because of the bully, but because of me, for allowing it.

The lesson: Every time you tolerate a behavior, you’re endorsing it. Your team is watching what you accept, what you ignore, and what you reward. That — not your mission statement — is your culture.

Lesson 5: Hire for the team, not the role

Early on, I hired for skills. Could this person design? Could they code? Could they write? I assembled a collection of talented individuals who happened to work in the same office. It wasn’t a team — it was a talent show.

The shift came when I started hiring for how someone would change the dynamics of the group. Would they elevate the people around them? Would they challenge ideas constructively? Would they share credit and absorb blame? Skills can be developed. Character is largely fixed.

The lesson: The best teams aren’t collections of the best individuals. They’re groups of good people who make each other better. Hire for the effect someone will have on the team, not just the work they’ll produce.

Lesson 6: Your job changes, and you have to let it

The thing that got you here — your ability to do the work — becomes increasingly irrelevant as you grow. At five people, you’re a player-coach. At fifteen, you should be a coach. At fifty, you should be designing the playbook and letting others run it.

I resisted this violently. I was good at the work. I liked doing the work. Letting go of it felt like losing my identity. So I held on — reviewing every design, rewriting copy, sitting in on client calls that didn’t need me. I was a bottleneck disguised as a quality standard.

The lesson: Leadership requires letting go of the thing you’re best at to focus on the thing only you can do. For me, that was setting direction, building the team, and maintaining the client relationships that kept us alive. For you, it’ll be something else. But the pattern is the same: your job changes, and the ones who can’t evolve with it plateau.

The synthesis

Years later, I can see the thread connecting all of these lessons: leadership is fundamentally about managing the distance between yourself and the people you lead. Too close (friends), and you lose the ability to make hard decisions. Too far (servants), and you lose the trust that makes good work possible.

The right distance is professional respect infused with genuine care. It’s honest, boundaried, and consistent. It’s saying “I’m invested in your success” while also being willing to say “this isn’t working.” It’s neither friendship nor servitude — it’s stewardship.

I wish I’d understood this at 26. But some lessons only land after you’ve made the mistakes. The best I can do now is share them with someone who might be about to make the same ones.