Lessons From Three Bosses

The boss you have reveals the future you’re building.

I’ve worked for three different bosses. Each one taught me something different about what I was willing to tolerate, what I was capable of, and where I needed to go next. If you’re trying to figure out whether to stay or leave, start here: which boss do you have?

Boss #1: The Chaotic Manipulator

Disorganized. Motivational when it served them. Talented at creating revenue.

But here’s the problem: they had a low lid of leadership.

They couldn’t train more than a few people to do what they did. The skill was personal, not transferable. So instead of building a self growing team, they led through manipulation and control. The environment became toxic fast. You either left, or you went blind to it. Or worse—you became it.

If this is your boss: You’re not learning. You’re surviving. And survival isn’t a strategy. Leave.

Boss #2: The Money Servant

The second type serves the investors. Every decision filters through one question: What does the person who who writes everyones checks want?

This creates a different kind of lid. No matter how talented or creative you are, no matter what value you bring, no matter what ethics or morality you operate with—you will be squashed by the person at the top and their love of money.

Here’s what’s interesting: what they love, they also fear.

They’re terrified of making a mistake. So they’ll rarely try a new idea, even a modern one that is proven to work. If someone in the organization speaks truth or offers wisdom about solving a real problem, they’ll crush it. Creative people get fired. Passive compliers get promoted.

You’ll be paid decently but never what you’re worth. And that’s how they keep control.

" When your boss serves money or self instead of mission, creativity becomes a liability. "

Boss #3: The Team Builder

The third type sees complete value in the people around them. They rely on the team to get the job done. They give you agency, free will, room to think and grow.

This creates reciprocity. The team values the boss. Everyone protects the organization and the leader. It’s probably the best type of boss there is.

But some have a blind spot.

They’re so involved in building the team horizontally that they have no time to build vertically. That creates a lid, a leadership ceiling that limits the growth of the organization.

But when talented people find this boss, they stick around. Because they’re giving them the runway to use their gifts.

What This Means for You

The Bible is full of leaders: some who manipulated, some who hoarded, and some who served their people well but still had limits.

If you’re working for Boss #2, you’re watching this play out in real time. The love of money doesn’t just hurt the leader, it pierces everyone around them. Creativity dies. Truth gets punished. You get paid just enough to stay quiet.

God didn’t wire you to be quiet. You have a voice. He gave you gifts to use, not suppress.

“Each of you should use whatever gift you have received to serve others, as faithful stewards of God’s grace in its various forms.” — 1 Peter 4:10

If your boss won’t let you steward your gifts well, you’re not in the wrong when they hold you back. You’re simply in the wrong place.

The team-builder boss? That’s closer to what leadership should look like. But even they need accountability, vision, and someone pushing them to think beyond the team they’re building today. They need to focus on who they will server tomorrow.

Your job isn’t to fix your boss. Your job is to use your gifts well, work with integrity, and know when the environment you’re in is limiting what God put in you.

Further Learning

• The Law of the Lid (John Maxwell) →