Coaching for leaders who run teams
Stay clear-headed when the team around you is not.
I coach leaders and managers who carry the pressure for a team. You will leave each session with a clear next move and a calmer way to make it.
Book a free consultThirty minutes. Free. No pressure.
- ICF Associate Certified Coach (ACC)
- Coaching since April 2022, with 150+ clients, including business owners
- 2,600+ coaching sessions
What you carry
You work hard. The same problems keep coming back.
You run a team. Deadlines, moods and mistakes all land on your desk. You answer every one of them.
You push harder. A month later, the same problem is back, in a new way, and you are more tired.
More effort rarely fixes a problem that lives in the structure around you. You do not cross a canyon by jumping harder. You find the route.
That is the work I do with you, as your guide and navigator.
What changes
After we work together
- You know what you want, and what you need to change to get it.
- You stay steady in tense meetings and hard conversations.
- You are clear about who you are as a leader, and more people follow you.
- You see the pattern behind a problem that keeps returning, and you change the pattern.
- Your team owns more, because you hold your own position.
How I work
I look at your team, and the people around you, as a system
A system is a group of people who react to each other all day. When one person gets tense, the others feel it. When you can see that, you have more choices.
Stay calm and connected
Bowen family systems
You hold your position while the people around you are anxious. You stay close to them without being pulled into their pressure.
Find the loop
Cybernetics
Every team runs on feedback. A late report results in a sharp email. The sharp email leads to a quiet week. We will find the loop that keeps your problem in place.
Change the structure
Second-order change
When effort does not fix it, we change the setup around it: Who decides. How work moves. What gets said, and when.
In a session, we work on a real situation from your week. You leave with one clear next step.
About me
Caleb Grimes
ICF Associate Certified Coach (ACC), earned in 2025
I started coaching in April 2022. Since then I have coached 150+ clients and led more than 2,600 coaching sessions.
Before that, I spent over ten years at Chick-fil-A. I started as a trainer and grew to become a general manager, and learned about what it means to be with people while doing everything in between.
From 2021 to 2022, I helped open a restaurant in Hollywood in the middle of the Covid pandemic. Then I ran back-of-house teams for two stores while running a ghost kitchen at the same time. I know how it feels to lead people when the pressure is on and the orders keep coming.
Those years taught me that most team problems come from structure, and from how people react to each other. Effort alone rarely fixes them. That is why I coach the way I do.
How it works
Three steps. The first one is free.
A free 30-minute consult
You tell me what you are dealing with and what you want to change. You see how I work. If coaching is not the right fit, I say so.
A coaching agreement
If we both want to go ahead, we sign a simple agreement. It sets the goals, the schedule and the ground rules.
Regular sessions
We meet on a set schedule and work on real situations from your job or your life. Each session ends with a clear next step.
Bring one problem. We will look at it together.
Thirty minutes, free. Pick a time that works for you.
Book a free consultPrefer email? Write to caleb@crossingcanyons.com.