Not on purpose. But that's how it went.

He was your most reliable climber. Fast in the tree. Customers loved him. Showed up on time, didn't cause drama, and you could trust him with the keys to the truck.

So you made him a crew lead.

And you handed him a crew and a schedule, and said something like, "You got this," or "just run it like I would." Maybe a small raise. Maybe the promise of more later.

Six months in, the wheels are coming off. His crew isn't producing. He's frustrated. He's either micromanaging everything or he's checked out and letting the crew run itself. The other guys on his team don't respect his authority because yesterday, he was their equal.

Sound familiar?

Here's the part nobody wants to hear: this isn't a "him" problem. This is a "you didn't train him" problem.

Being great with a chainsaw and being great at managing people are two completely different skill sets. And in most tree services, the promotion from climber to crew lead comes with a title change, a small pay bump, and absolutely zero support.

Then we blame the guy when it doesn't work out.

The companies that grow past $5M have figured out something the rest haven't: crew lead development isn't optional. It's the bottleneck. You can have all the equipment, all the customers, and all the work you want. If you can't develop leaders who run jobs without you, you're stuck.

Here's what a structured crew lead development path looks like. It's a framework built around the three skill gaps that trip up new crew leads the most.

Your new crew lead knows trees. He doesn't know how to tell a 35-year-old guy to pick up the pace, or how to handle the employee who does good work but has an attitude, or what to do when two guys on his crew can't stand each other.

During the first month, your crew lead needs to learn three specific things:

Do you currently have a standard for any of those three things? Or does every crew lead just figure it out on their own?

This is where your crew lead learns to think about the whole job, not just his part of it. That means understanding how long a job should take, how to sequence the work, how to keep the crew moving between tasks without dead time, and how to handle on-site scope changes.

The biggest mistake new crew leads make is jumping in and doing the work themselves instead of directing their crew. They default to being the best worker rather than the manager.

During weeks 5-8, pull your crew leads off the saw for at least two days a week. Have him manage from the ground. Watch what happens. It will feel wrong to him. That's the point.

This one gets overlooked the most. Your crew lead needs to know how to communicate with you (or your ops manager) in a way that's useful. Not a phone call at 4:30 with a list of problems. Not silent until something blows up.

What does a good end-of-day report look like from a crew lead? Can your crew leads give you a 60-second summary of the day that tells you what got done, what didn't, and what you need to know?

If they can't, they're managing by reaction. And so are you.

How many of those have you actually said out loud to your crew leads?

Have conversation #1 from the list above with every current crew lead. Even the ones who've been doing it for years. You might be surprised by what they don't know you expect. (15 min per person)

Here's what frustrates me about how this industry handles promotions.

We take the person who's best at the technical work, and we "reward" them by giving them a job they've never been trained for. Then we're confused when they struggle.

Think about it from his side. Last month, he showed up, did great work, and went home. He knew exactly what was expected. Now he's responsible for three other people's output, he's dealing with scheduling conflicts, customer complaints, equipment problems, and interpersonal garbage. And nobody gave him a single tool to handle any of it.

That's not a promotion. That's a setup.

The owners who build real companies (the ones that run without them in the truck every morning) have figured out that developing crew leads is the single highest-return investment in the business. Not equipment. Not marketing. Not a new CRM. People.

One last question: if you got hurt tomorrow and couldn't go to a single job site for 90 days, would your crew leads keep things running? Or would the whole thing start sliding?

Your answer to that question tells you exactly how much work you have to do here.

If you've promoted someone recently and it's not going the way you hoped (or you're about to promote someone and want to do it right), hit reply and tell me:

I'll send you back a specific suggestion based on what I'm seeing work in other tree services of your size.

Talk to you all next week!

-Jacob