One of our operators was telling me about a conversation with the COO of a payments company. The COO was in the office 60 or 70 hours a week. Finding time to speak with him meant booking a call in the evening.
He had a team. He had technical people. He had hired a project manager.
And he was still personally dragging the work forward.
Underwriting was taking too long. He was worried about losing partners and merchants. He was showing people what he wanted, issuing directives, and getting frustrated when the organization couldn't keep up.
The project manager could chase tasks. But the COO still had to explain why the work mattered, how the business worked, and what needed to happen.
As the operator told me the story, one thing became obvious: this guy needed somebody to take some of the thinking off his shoulders.
Having people doesn't automatically give you relief
The operator had deep experience in payments. He could understand the business context and translate it into execution.
That mattered in this conversation. The COO was describing technical discussions where he still had to explain how payments worked. He was doing the translating himself.
Then he started imagining what life would look like if our operator took over parts of that work. Maybe he could manage the project manager. Maybe he could take the meetings. Maybe the COO wouldn't have to be the person pushing everything through.
That's where the conversation got interesting to me. There were real things this person wanted off his plate.
If you're a business owner and that sounds familiar, look at what still comes back to you. Are you explaining the problem? Designing the solution? Coordinating the people? Making sure somebody actually follows through?
Those are the things I wanted our operator to put into the proposal. The actual work the COO had already said he needed handled.
Start with the work you want off your plate
They had started getting into hours, titles, payroll, and compensation. My advice was to get clear on the work first.
I told the operator to put together a simple document. The top half would lay out the problems the COO had described and what the operator would take responsibility for.
Before discussing the terms, walk through that part together. Is this right? Is this the work you need done? Would having somebody handle these things make your life easier?
The COO was already making decisions all day. I didn't want this engagement to become another thing he had to build from scratch.
I wanted the operator to go first. Put pen to paper. Give him something clear to react to. Take some of that weight away before the relationship even starts.
The words I wanted him to use were simple: let's talk about what this looks like for me to just handle it, so you don't have to mess with it anymore.
More profitability. Less complexity.
In a separate Loom, I was helping another operator think through a proposal. I told him there were two things the owner needed to see: a positive financial impact and less complexity in the business.
I put it this way: I want to know I'm not wasting money, and I don't want my life to get harder. I want my life to get easier.
That's what I want our operators to deliver. More profitability. Less stress. Hours back in the owner's life.
So when you're considering executive help, get specific about what somebody will take over. Ask them to describe the work, the problems it solves, and what you will be able to stop doing.
A clear proposal should let you picture that change. You should be able to look at it and think: yes, those are the things I keep carrying. Yes, I want somebody who understands this to handle them.
That's the feeling I was trying to create in that conversation. A big sigh of relief because somebody else had done the thinking and was ready to take responsibility.