~by Haley Lynn Gray~
I’ve made a great many leadership mistakes. Two of them taught me more than the rest put together, and they turn out to be the same mistake wearing different clothes.
The company car
At one of my businesses, we had a company car. It was there for our nurse administrator to use for client assessments — a clear, specific purpose.
I handed over responsibility for it and didn’t think much more about it.
What actually happened was this. The nurse administrator gave the car to another employee who didn’t have one. That employee kept it at home and used it for everything. And the nurse administrator, now without the car she was supposed to be using, was charging me mileage for driving her own.
So I was paying for a company car and paying mileage on top — for a car being used as someone’s personal vehicle.
I don’t think anyone set out to take advantage. The nurse administrator was probably trying to help a colleague who had no transport. She simply didn’t understand the implications of what she was doing, because I’d never explained them.
That was my mistake, not hers. I’d handed over a task without the purpose behind it. And then I never asked how it was going.
Too many people
The second mistake was hiring too many people.
It felt like progress. More staff, more capacity, a business that looked like it was growing. What I actually got was people who kept themselves busy — pushing peas around the plate — while the real productivity was nowhere near what the business needed to be profitable.
Nobody was lazy. That’s the part worth understanding. People don’t sit idle when there isn’t enough real work. They find work. They make tasks larger, add steps, attend more meetings, polish things that didn’t need polishing. From the outside it looks exactly like a busy, functioning team.
And my profit went straight down the drain paying for it.
There’s a name for this. In 1955 the historian C. Northcote Parkinson wrote an essay for The Economist observing that work expands to fill the time available for its completion. It’s now known as Parkinson’s Law, and I learned it the expensive way.
Why they’re the same mistake
Both came from the same place: I wasn’t looking closely at what was actually happening.
With the car, I delegated and walked away. With the hiring, I measured activity instead of results. In both cases the business looked fine from where I was standing, and in both cases it was quietly costing me money.
Busy people and a delegated task both feel like things are handled. Busy isn’t the same as productive, and handed over isn’t the same as handled.
What I do differently now
I delegate the purpose, not just the task. “Look after the company car” is a task. “The car exists so the nurse administrator can do assessments without mileage costs” is a purpose. If I’d said the second, the problem almost certainly wouldn’t have happened, because anyone who understood the purpose could see that handing the car away defeated it.
I ask how things are being done. Not in a suspicious way — just regularly and specifically. “Walk me through how the car’s being used.” Andy Grove’s advice to check early, at the point where problems are cheapest to fix, would have caught this in the first week instead of months later.
I look at output, not activity. Before hiring, I ask what specific results the new person will produce and how I’ll know. If I can’t answer that clearly, the role isn’t ready to exist yet.
I hire slower than feels comfortable. When the team is stretched, I first ask whether the work that’s stretching them is genuinely necessary. Often a good part of it isn’t — and hiring someone to do unnecessary work just makes the unnecessary work permanent.
And I read the numbers. Both problems showed up in the books long before I noticed them. Mileage claims for a car we owned. Payroll rising faster than revenue. Looking at the numbers regularly would have flagged both.
The lesson underneath
Most leadership mistakes aren’t dramatic. They’re small gaps between what you assume is happening and what actually is — left open long enough to become expensive.
Closing them doesn’t require distrust. It requires curiosity: asking how things are going, looking at what’s actually being produced, and explaining the why behind what you hand over.
I’ve written about the financial mistakes I’ve made elsewhere. These are the leadership ones. Both cost me real money, and both could have been prevented by a few good questions asked early.
