Becoming an Executive Head Coach

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The other day I was meeting with a fellow executive coach for the first time. Our meeting had been suggested to us through a mutual colleague’s virtual introduction. We were in the midst of that typical first meeting exchange when he asked me to tell him about my current work. I said that I am primarily working with CEOs and their teams/direct reports. His verbal and non-verbal reaction had him showing both displeasure and discomfort. He then said, “I have always tried to avoid doing that kind of work. It seems like it would be too messy.” His response caught me a bit off guard and I inquired as to why he thought that. He mentioned that doing executive coaching one on one was his preference and he was not sure if it was a good idea to coach both the leader and the team members because of confidentiality and other potential issues. I could see his point and agreed that it may not be for every executive coach.

The gift of that conversation was that it prompted me to think of another way to speak about coaching CEOs and their teams. If you have been familiarized with executive coaching over the last decade or so, you have probably heard it referenced with an analogy to sports coaching. “Even ____ (you fill in the professional sports figure) has a coach. Why wouldn’t an executive also have a coach?!” If the professional journey is about continuous improvement as a leader, in both your doing and your being, then having an executive coach can be a very helpful. However, most of the analogies to sports coaching have been focused on individual performers like golfers, tennis players, track athletes, etc… Team coaching is, pardon the pun, a whole different ballgame.

Earlier in my conversation with the other executive coach, I had made a reference to Phil Jackson and his new book, Eleven Rings. For me it was a good read on both a sports level and from a spiritual/psychological perspective. Phil’s greatest success was not as an individual player, it was as a head coach. Then it hit me. Even though I have primarily been an individual executive coach, what I do now is more akin to head coaching. I had become an executive head coach.

As an executive head coach, I have individual and collective relationships with all the players/ members of the team/c-suite. When Phil was head coach of my/the Lakers, he did not only have a relationship with just the team captain(s), he also had a coaching relationship with each player. Those relationships were all different. And he leveraged those individual relationships to co-create/ develop NBA teams to become championship teams. In the opening chapter of Eleven Rings, he says, “… the art of transforming a group of young, ambitious individuals into an integrated championship team is not a mechanistic process.

It’s a mysterious juggling act that requires not only a thorough knowledge of the time-honored laws of the game but also an open heart, a clear mind, and a deep curiosity about the ways of the human spirit.”

In my work as a head coach for CEOs and their teams, I would concur with Phil that transforming a group of individuals into an integrated team is not a mechanistic process. It is a mystery. And I believe it is a mystery worth exploring – together.

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