Why I founded a leadership development company

Photo by Noah Silliman on Unsplash

Photo by Noah Silliman on Unsplash

I didn’t sign up for this. 

I remember saying that to myself the moment I realized I’d failed to lead my team—the Detroit branch of a Chicago media company—to success. Our problems were many, and I just couldn’t make heads or tails of it. Surely it was a fluke. We closed the office and I moved on. After all, I hadn’t signed up for the mess I’d inherited. 

Turns out I didn’t sign up for the next one, either. It was a high-fly and fast-growing real estate consultancy. The hours were long. The pace was crazy. My life was out of balance. I was burned out and had lost sight of my values. The worst of me was getting the better of the best of me, and I moved on, yet again, for my own sanity. 

The next gig would make sense. Or so I thought. But the economic downturn, and my inability to navigate it, out-jousted me. The economic downturn was very real—for millions of people all over the country—but again, that familiar refrain rang out louder than logic. I didn’t sign up for this. I was sure of it.

My next assignment was completely different in every way: new industry, new role, new company structure. I did some good things there, but wasn’t wildly successful. Most importantly, as an executive leader, I couldn’t get my peers—let alone the organization—rowing in the same direction. We were flat as a pancake: neither a complete failure, nor stewards of the success we all desired. The success we could have had. 

After 15 years, it finally came to me. Maybe it wasn’t my boss, the market, the product, my team, or any of the things “I didn’t sign up for”. Maybe the problem was ... me? 

I “quit” leadership and returned to sales. Humbled by my trail of shortcomings, I decided it was time to learn. I immersed myself in the literature and language of leadership. In my desert wandering, I was fortunate to find some fellow travelers who’d been on the journey much longer than I. They encouraged and equipped me. Their wisdom and approach was simple and bold. It clearly wasn’t easy, but it made sense to me. And it seemed doable. Most importantly, I resonated with what I discovered: a thoroughly holistic approach to leader development. It made me feel empowered and capable. I even found healing. 

I’m thrilled to say that in quitting leadership, I found it. I came to deeply love the way leader development was modeled for me, and I finally found myself thinking if there was a way I could pay it forward.

Farmers designate trees of exceptional fruitfulness as “rootstock”. These resilient progenitors become the primary source from which future plantings are grafted, thus multiplying the desired traits for improved yield. It took me years in business chasing short-term crops until I finally discovered something was happening in the dirt. I am convinced that a unique fruitfulness lies somewhere beneath the surface of every leader and organization—a rootstock as it were—that is waiting to be put to good use.

At Rootstock, we’re called to help leaders thrive in change. We’re out to model the leadership principles we’ve discovered, and share them with our clients when they need it most. I believe in giving what I once lacked: clear guidance and versatile tools for the journey. 

I definitely signed up for this!

Tony Woodall