On my first job as a PM in Maryland, I was scared of giving the owner’s rep bad news.

When things went sideways I'd sit on it. Try to fix it quietly. Hope the problem disappeared before anyone noticed. I wanted us to look perfect in their eyes.

What I didn't understand was that they already knew. They always know. They have a finely tuned radar for guys managing perception instead of managing work.

At the end of that job I got rated "average" in the post-project survey.

That stung. It should have.

Before anything else - do this one thing.

Get in a truck with the owner's rep before the first blade of dirt moves. Ask two questions:

"What would make this a successful job in your eyes?"

"What are you most worried about?"

Then shut up and listen.

You'll learn more in that 30-minute ride than in three months of meetings. Now you know what winning looks like to them. Go win at that.

What trust actually means in construction

Trust means: I know you will do right by this project whether I am watching or not.

That's it. That's the whole definition.

When an owner believes that about you, everything changes. Change orders move faster. Disputes get resolved with a phone call instead of lawyers. The inspector gives you the benefit of the doubt. Pay apps don't sit on desks for 45 days.

When they don't believe it — every single one of those things goes the other way. And in a business running 5% net, that's not a relationship problem. That's a margin problem. The most profitable contractors I've known all have one thing in common: they earn trust that money can't buy.

I ran a job once where the owner hated us. Eighteen months of grinding through daily inspections, disputed quantities, slow pay, adversarial meetings. Painful every single day to walk into that trailer. It never got better.

Because we didn't trust them and they didn't trust us — and neither side ever had the guts to sit down and fix it.

When we closed it out, that broken relationship had cost us north of $400K. Lost margin on disputed change orders, claims, and a good manager who quit mid-job because they were tired of the war. Replacing them cost us time and money we didn't have.

It didn't have to be that way.

Trust → fewer disputes → faster payment → happier people → stronger margins. It compounds. A good owner relationship is worth hundreds of thousands of dollars over the life of a job. A bad one costs just as much.

15 things I've learned about earning it:

1. Trust yields profit. It's built through consistency and doing exactly what you said you'd do.

2. Undercommit. Overdeliver. Never promise what you can't control. Promise what you know you'll hit, then beat it. Execution of safe quality work on time never goes out of style.

3. Owners hate surprises. They have bosses too. The worst day in a bureaucrat's life is when their boss finds out about a problem before they do.

4. Deliver bad news early. Every time. Bad news is like fish — after a few days, it starts to stink.

5. When you mess up, own it and fix it immediately. The longer you wait, the worse it gets. That moment handled right is worth more than six months of smooth sailing.

6. Know the plans, specs, and contract better than anyone in the room — including the engineer. Make their job easier and they'll fight for you when it matters.

7. Be yourself. Get to know them as a person. There are no awards for keeping things to yourself.

8. Phone call beats email. Every time. The second you sense tension — call. Not text. Not email.

9. Don't nickel and dime. You're not working for free. But you're also not a lawyer looking for billable hours on every gray-area item. Be reasonable.

10. You have leverage too. They need you as much as you need them. Never forget that.

11. Don't brag. Let the work speak for itself.

12. Don't go over someone's head unless you absolutely have to.

13. If it gets nasty — don't lose your composure. Document well. Use your superior knowledge of the plans, specs, and money to win.

14. Be ethical always and never ask for special treatment.

15. The construction world is small. People talk. Owners included.

What happens when trust erodes

You'll feel it before you can name it. The pay app that takes 45 days instead of 20. The inspector who now finds something wrong on every daily. The change order that sits on someone's desk for six weeks.

The fix is uncomfortable but simple: sit down face to face and talk about it.

Jerry Seinfeld ran one of the most successful shows in TV history for nine seasons — four lead actors, dozens of writers, hundreds of episodes — with virtually no drama. Tim Ferriss asked him how. His answer:

"I don't like discord. I don't like it, and I am fearless in rooting it out and solving it. And if anyone's having a problem, I'm going to walk right up to them and go, 'Is there a problem? Let's talk about this.'‘

When pushed on where that came from, Seinfeld said: "If you break the human struggle down to one word, it's confront."

The contractor who is fearless about walking into an uncomfortable conversation will always outperform the one who avoids it. Always.

Your move this week

You've got a job starting soon.

Before the first truck rolls - get in a truck with the owner's rep. Drive the job. Ask them what success looks like. Ask them what keeps them up at night. Then shut up and listen.

That one conversation, done right, is worth more than anything else in this newsletter.

In Case You Missed It:

Intelligent Bidding

Just Be a Good Human Being Who Pays Attention

What’s In Your Control?

Enjoyed this newsletter? Forward it to a friend and have them sign up here!

About the Author

Tristan Wilson is the CEO and Founder of Edgevanta. We make AI agents for civil estimating. He is a 4th Generation Contractor, construction enthusiast, ultra runner, and bidding nerd. He worked his way up the ladder at Allan Myers in the Mid-Atlantic and his family’s former business Barriere Construction before starting Edgevanta in Nashville, where the company is based. Reach out to him at [email protected]