Hero-Led or System-Led

Make My Mess My Message · Issue 18 · 9 October 2026

I expected a report card. What came back was an inventory.


In 2021 I handed my company to the leadership team and left for a year.

I expected a report card. What came back was an inventory.

Not a sabbatical. I was still the owner, still in the building some of the time. But the running of it was theirs, and I wanted to see what I had actually built.

What came back sorted into three piles.

The first was everything that simply ran. Prepared, understood, nobody needing me.

It was the smallest pile. That still stings.

The second was the fires. The things that went wrong loudly, where somebody came to me and said this is broken and we are going to die.

That was the pile I had braced for, and it turned out to be the safest of the three. Every item in it had already been seen and understood by the person raising it. A problem a team can describe is a problem that team will solve, usually faster than I would have.

The noise was a sign of health.

The third pile was silent.

These were fundamental things that were not in place at all, and nobody in the room knew they were missing. No alarm went off, because an absence does not set off an alarm.

Here is what was on it. This is the useful part and the embarrassing part.

How to hold a meeting.

How to decide without waiting for consensus.

How to set a long-term goal and work backwards from it, instead of running at whatever was burning that morning.

How to hire. How to fire. How to grow somebody who is already good.

How to reward people for the right thing, which I wrote about last month and which was one line on a longer list.

Not one of those is advanced. There is no MBA anywhere in that list.

And not one of them was something the team had failed to learn. Every one was something I had never installed.

Underneath all of it sat the thing I had never said out loud.

I had never explained what the job is.

Running a company is not getting through today.

Think of an accordion.

You pull it open and you find room. Opportunity, movement, new people, new ideas. You also get chaos and stress and pain, because open is where things break.

So you close it again. Order, process, stability, everything back in its place. Close it too far and the music stops.

There is no correct setting. There never was. The job is the pulling and the closing, over and over, and knowing which one this year needs.

Nobody had ever told them that. So they did the only job they had been handed. They took care of the day. The orders, the fires, the customer on the phone. They were good at it, and they spent that year looking at their feet instead of at where we were going, because nobody had told them to lift their eyes.

The other thing I never built was the part where everybody pulls the same way.

I thought that was a matter of telling people. Here is the plan, here is where we are going. I said it clearly, more than once, and I assumed clear was the same as shared.

It is not. People carry a goal they helped build. They carry out a goal they were handed, and that one does not survive the first hard week.

Three Fridays ago I named three habits that got me here. Hiring for the job in front of me. Training people only for the job they held. Deciding everything myself.

Reading them back, two of those are too tidy. I did hire for the next role, often. I did hand over real responsibility, and plenty of it worked.

The third one was true, and it is the only one that matters.

I was in the room too often. I decided too fast.

Now the part that will annoy some of you, and it should.

That worked. For years.

A founder in the middle of everything is the fastest way a small company will ever decide anything. No meeting, no slides. You see it, you call it, it moves. In the early years that is not a flaw, it is the reason you are still here while better-funded people were consulting each other.

I would do it again. I think you have to.

Hero-led or system-led is the question everybody asks, and everybody answers system, because nobody wants to be the hero. Founder on a horse, cape, the whole picture.

It is the wrong question. Both are right, at different times. All of the difficulty is in the crossing.

Because getting out of the middle is not the next step up. It is not the same job done better. It is a pivot. A different job, with different skills, started from zero, in front of people who watched you be good at the old one.

And it is just as hard for them as it is for you.

You see it most clearly in sales. Somebody is brilliant at closing. Give them a team and everyone expects the skill to scale. It does not, because the job changed. Plenty never make the switch, and a few answer the pressure by closing even harder, becoming the hero twice over while the people behind them learn nothing.

That is what I did for seventeen years, with a company instead of a territory.

In July a reader asked me how a coach corrects course without becoming the bottleneck. I wrote back that I had dropped ownership on people without the tools, context or confidence to carry it. You cannot shock anyone into initiative. The silence I got was my failure, not theirs.

They were not refusing to step up. They were being asked, with no warning, to do a job nobody had ever described.

There is an honest edge against my own side of this. A system grows its own hero too. Write enough down and the process becomes the authority, nobody moves on anything outside the manual, and the speed you were proud of is gone. I have seen that in companies far larger than mine.

The goal was never procedure. The goal is that a capable adult can act without me and knows what good looks like.

So here is the test, and it costs you nothing but honesty.

Pick a week in the next two months and go away properly. No calls. No approving things from your phone. No quick question on the way out of the door.

When you come back, do not ask how it went. Sort it into the three piles.

What ran. What broke loudly. And then the hard one, the one nobody will bring you. What decisions never got made. What nobody started. What people waited on, and why waiting felt like the right call.

If the first pile is smaller than you expected, you have the same answer I got.

It took eighteen months and outside help to work through that list. Not a workshop. Eighteen months, with how to hold a meeting at the top of it.

The things that came closest to costing me the company were never the fires. They were the items nobody was shouting about, because nobody knew they were absent.

That was not the team’s gap.

It was the bill for seventeen years of being the fastest man in the room.

w. 🌊


Make My Mess My Message is a book written in public, one Friday at a time. Every issue lives here.

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