About
Caleb Grimes
I help leaders see the system they work in and change it. More and more, that system includes AI.
I started coaching in April 2022. Since then I've spent more than 3,000 hours coaching leaders and owners.
Before that, I spent ten years leading restaurant teams, from trainer to operations director. I built a coaching process for more than 180 team members, so everyone got regular feedback and room to grow. I helped open a new restaurant in 2020, just before Covid. Then I ran the back of house for two locations while I ran a ghost kitchen.
That season was the hardest of my leadership. I was a fixer, and it stopped working. I learned to sit with people in hard moments and to listen to understand. My faith and my values shape how I show up.
Coaching gave me systems thinking. Team problems usually come from structure, and from how people react to each other, so effort alone rarely fixes them.
AI is the newest part of the system. I build with it every day, from agents that work like a small team to a loop that learns from its own mistakes. I help leaders use it the way I coach: they see the whole system first, then change one piece at a time.
ICF Associate Certified Coach (ACC). Master of Social Work student at Arizona State University. BA, Providence Christian College.
Now · November 2026
What I'm working on
- Building this site, and the 3D map of my work on the home page.
- Shaping my AI work for leaders and small teams.
- Studying for my Master of Social Work at Arizona State University.
- Coaching leaders and owners every week.
Work with me
Two ways to work together
CoachingOne-on-one coaching for executives and leaders who carry the pressure for a team. Team sessions when the whole group needs to see the same system.
AI for leaders and small teamsWe find where AI fits in how your team already works, set it up together, and you learn to run it. The goal is that you don't need me.
Writing
Latest on Substack
- My best solutions are often my worst problemsMay 15, 2026
Newsletter
Get new posts by email.
Contact