"From Coach to CEO and Back" at WBECS Summit

2 September 2020

Very few of us follow a linear journey that we imagine when we are schoolchildren. Our careers are a series of decisions that we make based on the information we have at the time, and one decision leads to the next. This is how I came to find myself co-leading the Scrum Alliance, walking a tightrope between Coach and CEO.   My official title is Chief ScrumMaster. A ScrumMaster is a coach who serves the team by ensuring that its needs are being met, by looking for ways to enable change and improve performance, and by removing impediments to success. As Chief ScrumMaster, I do this at scale--for the entire organization. I am also a co-CEO, which is an interesting combination. 

Two Conflicting Roles

I did not realize when I accepted this job how frequently my two roles would be in conflict. As coaches, we are trained to help our clients and teams find the answer inside themselves. As leaders, we are expected to provide the answers. It took some time for me to balance those two things, establishing clarity and context, and then coaching the team to find the answers in that context.  

Walking a Mile in New Shoes

I have been a coach for quite a while now, so I know how challenging it can feel to always be on the outside with little to no authority. I’ve now been a CEO for long enough to know that leadership comes with its own challenges. I have plenty of authority, but it’s just as lonely and a whole lot heavier.

This experience has created a lot of empathy in me for both roles.

I look back at my experiences as a coach, and I can remember times where I was lacking patience (if only in my head) for the leader I was coaching. We could both see the path forward so clearly, and could not understand why they didn’t “just do it.” I’d never verbalized it, of course, but the thoughts were there. What I did not recognize was the many layers of burden and care that were invisible to my coaching eye, the incredible responsibility, and the need for nuance that comes with that leadership title.

As a leader, I often have this “You don’t understand” sense about me, as do many leaders that I know. I am constantly balancing the needs and priorities of many people, knowing I can never make them all happy. And I’m not always able to share all of the reasons for my decisions. I also cannot always be Socratic. Leaders must lead.

A Journey to Empathy

So how does one blend the “Just do it!” with “You don’t understand!”? For me personally, it started with the recognition of those two narratives in my head. When I learned how to acknowledge the leader’s fears and burden while channeling the coach’s optimism, I began the dance of balancing stability and rationality with innovation and high-quality risk. I learned how to create a solid, safe foundation for our team to find new and exciting solutions to problems. There’s a whole lot more to this story, and I’m excited to have the opportunity to share it at the WBECS Summit on September 10, 2020. Scrum Alliance Community members can watch it for free here. I hope to see you there.