“You can go your own way…”
— Fleetwood Mac, “Go Your Own Way”
Most companies don’t fail from a single dramatic blow. They fail from drift a thousand small misalignments nobody noticed because nobody was looking. Buildings don’t wait until the roof caves in to be maintained, and neither should companies, but most of them do exactly that. If your quarterly reviews feel more like archaeology than leadership, and you keep discovering problems that have clearly been there for months, the issue may not be your team’s attention. It may be the complete absence of preventative maintenance.
What Preventative Maintenance Actually Is
A well-run building has a schedule the occupants never see. HVAC filters get changed on a calendar, not a complaint. Elevator cables get inspected before they fray. Roof membranes get checked every spring, whether or not they leaked last winter. Sealant gets replaced before the water finds its way in.
The entire point is to catch problems while they are still cheap, quiet, and small.
A reactive building maintenance program is not a program. It’s a sequence of emergencies dressed up in work orders. By the time something is obvious enough to demand attention, it is already expensive. The job of maintenance is not to respond to failure it is to prevent it from ever arriving.
The Leadership Parallel
Companies drift. It’s the most ordinary thing in the world, and the most dangerous.
Strategy drifts from where you said you were going. People drift from the roles they started in. Systems drift from the assumptions that built them. Culture drifts from the values on the wall. None of it happens loudly. It happens a quarter at a time, a hire at a time, a shortcut at a time, a compromise at a time.
Here is what an unmaintained company looks like:
- Priorities from two quarters ago are still quietly shaping calendars today
- Role descriptions no longer match what people actually do
- Metrics are being measured but no longer being acted on
- Decisions made in a Tuesday meeting six months ago are still in force and nobody remembers why
- Onboarding teaches new hires a version of the company that no longer exists
- The founder’s biggest frustrations are the same ones from last year, just louder
None of these require a crisis to emerge. They emerge on their own, slowly, the moment you stop looking.
Why It Gets Worse at Scale
At small scale, drift is visible. You see every hire, every meeting, every process, and you can course-correct on instinct. The whole company fits inside the founder’s peripheral vision.
Scale removes that.
At a hundred people, you are no longer seeing the company you are seeing reports about the company. At three hundred, you are seeing reports about reports. Every layer between you and the work introduces a little more distortion, and distortion is the perfect environment for drift. Things don’t have to go wrong for you to lose the thread. They only have to go slightly off, in small increments, while you’re busy.
This is why so many growing companies feel suddenly “off” without being able to name why. Nothing broke. Everything just quietly moved.
What Healthy Preventative Maintenance Looks Like
Preventative maintenance in leadership is not a vibe. It’s a calendar.
Healthy companies build inspection into the rhythm of leadership the same way a facilities team builds it into the rhythm of a building:
- Strategy is re-read and re-tested quarterly, not framed and forgotten
- Roles are reviewed on a schedule, not just when someone’s unhappy
- Metrics that no longer drive decisions are retired, not kept out of habit
- Values are audited against actual behaviour, not against the website
- The founder takes dedicated “inspection” time — blocks specifically for asking “is this still the right shape?”
- Skip-levels are routine, not a red flag
- Hard conversations happen early, while they are still small
- Every system in the company has a stated owner and a review date
Maintenance is not glamorous. It is not what people brag about at conferences. It is, however, the single clearest signal of leadership maturity I know.
The immature leader waits for breakdown. The mature leader schedules inspection.
The Rebuild (A Personal Note)
Here is something the accident taught me that I still use every day.
After you rebuild a body the surgeries, the rehab, the relearning you don’t just get to walk away and resume your life. The work is never actually finished. There are muscles that compensate for muscles that don’t work the way they used to. There are joints that will lock up if I stop paying attention. There are habits of movement I have to check, quietly, every week, for the rest of my life.
I don’t love this. Nobody loves this. But I have learned that the alternative assuming the rebuild is permanent and moving on is how people end up back in the hospital.
I watch CEOs make the same mistake with their companies. They go through a hard rebuild a reorg, a strategy pivot, a painful hire or fire and then they exhale and move on. They stop inspecting. They mistake the moment of the rebuild for the end of the work.
It isn’t. The rebuild is the start of the maintenance. Every strong structure I’ve ever seen, in a body or a business, stayed strong because someone kept looking at it. Not anxiously. Not constantly. Just faithfully.
You can, as Lindsey Buckingham put it, go your own way but the structure you leave behind you will still need someone to walk its halls and listen for the creaks. If that isn’t you, it needs to be someone, on a schedule you can name out loud.
Final Thought
The best leaders I know are not the ones with the most impressive rebuilds. They are the ones with the most boring maintenance schedules.
They catch the misalignment in week three, not quarter three. They have the awkward conversation at 10% drift, not 40%. They treat their company the way a good engineer treats a bridge with respect, with schedule, with the humility to assume something is always, somewhere, quietly moving out of place.
You don’t lead a company once. You lead it in small, repeated acts of inspection, correction, and re-alignment. That’s the whole job. That’s the whole discipline.
Stop waiting for the crack. Walk the building. Do it this week. Do it next week. Do it when nothing seems wrong, especially then.
—
Architect Series • Issue 10
“I rebuilt myself. Now I design companies that can survive anything.”
