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Behind the System 001 · September 1, 2026 · 4 min read

The $100,000 bid that sat for months


Hey,

I’ve been working with a concrete contractor who has been in business for more than 20 years.

And this man knows concrete. Square footage. Linear footage. Labor. Materials. Risk. What questions to ask. What makes the price move.

You put a project in front of him and he can start making sense of it almost immediately.

That wasn’t the problem.

The problem started after he knew the answer.

And that’s what caught my attention.


The System

For a residential job, he’d meet with the customer, walk the project, ask his questions, and figure out what needed to happen.

Most of that information went to one place:

His head.

Then he’d go home. His wife helps him with proposals and some of the administrative side of the business, so he’d basically have to explain the job all over again. What the customer wanted. What he saw. What needed to be done. What could change the price. What needed to go into the proposal.

So if you followed the information, it looked something like this:

Field Note #001: I followed the information. It kept coming back to him.

That’s when I started thinking:

Wait a minute. The company already has the information. Why does it need him to recreate it before somebody else can use it?

And we’re not talking about one conversation. He might have ten of these in a day.


Then We Got to the Commercial Work

This is where it got really interesting.

Commercial opportunities would come through email with blueprints. He’d have to find the email. Find the plans. Open everything. Figure out what they were asking him to price. Start working through the project.

Then sometimes, after spending all that time on it, he’d realize:

I’m missing something.

Now he’s going back to the contractor asking another question before he can keep moving.

One of those opportunities had been sitting there for months. While we were talking, he reached back out. Basically: Y’all still need this?

Yep. They did.

And they needed the proposal Monday.

It was Friday. 😂

You already know where his mind went.

Well… there goes my weekend.

And here’s the thing: it wasn’t because he didn’t know how to price the job. He’s been doing this for more than 20 years.

He was about to lose his weekend because every time he opened one of these opportunities, he had to rebuild the thinking around it.

That’s a completely different problem.


So Before We Built Anything…

It would’ve been really easy to look at this and say: “You need better estimating software.”

Maybe. But software wasn’t my first question. I wanted to know: how does this man actually think?

Field Note #002: I followed his thinking. That’s where the real system was hiding.
  • What services does he provide?
  • What’s the starting price?
  • What moves the number?
  • What information does he need before he can price something?
  • What creates additional risk?
  • What makes him stop and ask another question?
  • What does he see after 20 years that somebody newer probably wouldn’t see?

Because that’s the good stuff. And he already knew all of it.

We weren’t trying to teach him how to estimate concrete. We were trying to stop making the company rent his brain every single time it needed that knowledge.

Once we started getting that thinking out of his head and into something the company could actually use, something interesting happened.

That proposal he thought might eat up his weekend? We worked through it in less than an hour.

And he won it. About $100,000.


But That’s Not Actually My Favorite Part

Listen, winning a $100,000 bid makes the story better. I’m not going to act like it doesn’t. 😂

But that’s not the part I’ve kept thinking about.

It’s this: his experience finally had somewhere to go.

For years, keeping everything in his head was probably one of his greatest strengths. He remembered the conversations. Remembered the prices. Remembered the relationships. Remembered what happened last time. Remembered what needed to happen next.

And when a company is small enough, that can work really well.

Until one day the thing that made you valuable becomes the thing the company can’t operate without.

That’s a strange transition. Especially when you’re starting to think about eventually leaving the business.

Because the trucks can stay. The equipment can stay. The crews can stay. The customers can stay.

But if the knowledge required to turn an opportunity into revenue walks out with you… how much of the business actually stayed?


The Thinking Worth Stealing

If the company keeps coming back to someone to remember what happened, the information never really became the company’s.

I’m not saying turn everything in somebody’s head into a 97-page SOP nobody is going to read. Please don’t do that.

And I’m definitely not saying technology should replace 20 years of judgment. It can’t.

But you can give that judgment somewhere to live.

Sometimes the first move is much simpler: find where somebody already knows the answer, but the company keeps making them repeat it.

That’s worth following.


Try This

You probably have somebody in your company who gets described like this: “Just ask them. They know.”

Cool. Go find one piece of work that reaches that person. Then follow it.

  • How many times do they have to remember something?
  • Repeat something?
  • Explain something again?
  • Find something nobody else can find?
  • Tell somebody what happens next?

Because you might not have a people problem. You might have a business that hasn’t learned how to keep what its people already know.

—
Touré


P.S. Who’s the “just ask them, they know” person in your company?

If somebody came to mind while you were reading this, hit reply and tell me who it is and what everybody depends on them to know.

I read the replies. And honestly, that’s usually where some of the most interesting systems are hiding.

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