Jesse James Garrett

What does a leadership coach do anyway?

When people ask me what my private leadership coaching looks like, it can be hard to provide an answer—because there’s no such thing as typical in my work. There’s no formula, no programmed series of steps to follow. The work is highly personalized, bespoke to the individual and the moment, and never looks the same way twice. That’s part of what I love about it—the neverending challenge of recognizing what’s needed most and responding in kind.

Sometimes I’m in the role of strategic advisor, offering perspectives based on what I’ve witnessed over my career.

Sometimes I’m a relationship counselor, unpacking messy interpersonal dynamics.

Sometimes I’m an industry analyst, synthesizing the broad trends unfolding across the industry.

Sometimes I’m a personal growth coach, helping people overcome the inner obstacles to being their best selves.

Sometimes I’m a political consultant, advising on executive communications strategies and messaging campaigns.

Sometimes I’m a brainstorming partner, a creative counterpart to help you think your way out of a jam or imagine something entirely new.

And sometimes the most important thing I can be is an empathetic voice in the darkness of uncertainty, someone who can be with you in the mess without judgment or apology.

If you could use one or more (or all!) of the above, I hope you’ll reach out. I’m not the right coach for everybody, but for some people I can help create change they never thought possible.

Why I Coach

I’m not a leadership coach because leadership has come easily, naturally, or instinctively for me. I’m a leadership coach because my journey into leadership was difficult, painful, and filled with setbacks. I was wrong about important things, over and over again.

But I learned. I grew. I became someone new.

I can’t claim to have it all figured out. Leadership takes too many forms in too many contexts for anyone to have all the answers. But I do know first-hand what it means to take that journey—to ask yourself if there’s something more you could become that could enable you to create more for others.

But for too many years, I had allowed my leadership to be shaped by the demands placed upon me, rather than by my own intentions. Eventually I came to realize that by taking this reactive stance, I had effectively abdicated responsibility for my own growth. I was taking the question of who I was becoming through this work out of my hands, and putting it into the hands of whoever was screaming the loudest about who they thought I ought to be.

I realized that I needed to be as intentional in my approach to leadership as I had been in developing my craft as a designer. That meant asking myself what kind of leader I wanted to be, and what steps it would take to get there.

My leadership journey was largely self-directed, but looking back on it I saw that it didn’t have to be. When I discovered coaching, I realized that I could effectively become the kind of support that I never had in my own development as a leader—someone who knew from their own experience that change was possible, and could map the ways to get there.

I truly believe that empowered, intentional leadership activates the potential of creative teams in a way that nothing else can. I love being able to help more leaders find their own way to make that potential real.

You can find out more about my executive leadership skills development work and read client testimonials. The first step on your journey is my free 1-hour introductory session, which you can book right now.