My Favorite Mistake

E. Ann Hollier, Ph.D.Strategic Intuition

Newsweek Magazine runs a brilliant column titled “My Favorite Mistake.” Each week a different person describes something stupid they did earlier in their career that helped to define who they are today. When captains of industry, well-known politicians, and prominent celebrities ‘fess up to their most egregious blunders, you quickly realize: Nobody’s perfect. Nobody. What distinguishes our cultural leaders is that they invariably mine their tragedies and bone-headed mistakes for lessons, pick themselves up, and go on to do better.

I have always been a strategy consultant, but a few years ago I added executive coaching to my toolkit. My favorite mistake came early in my training as an executive coach. As a subcontractor to another firm, I worked with national and international corporate clients. Some projects I led myself, but as part of my induction I was sometimes paired with a more senior consultant. One of the latter was a particularly spectacular failure.

In preparation for a workshop, I emailed members of the senior management team requesting information I and my project lead would need. Big mistake. Actually, several big mistakes. First, I had violated the chain of command, on both ends. Consultants are compulsively careful to maintain a single point of contact with clients, ensuring consistent communication. I bypassed my project lead. Compounding my error, I wasn’t aware that several directors had administrative assistants who were the appropriate recipients of the request. My project lead got several complaints saying basically, “Who is this idiot and why is she writing to me?” To make matters even worse, what I asked for wasn’t quite what she thought we needed.

In an effort to be helpful I had ruffled feathers and created a huge kerfuffle that, in a highly protocol-conscious environment, took my project lead a while to unwind. Boy did it sting when she said to me, “It’ll be a long time before I work with you again.” Ouch, ouch, ouch!

Another mentor, knowing I often turn to dreams for business insights, suggested I ask for clarification on where I had gone wrong. That night I received the following dream:

Beginner’s Mind

I am an 8 year-old girl in a remote village in China. The village elders have summoned me, and I am standing alone in front of half a dozen grey-headed, stooped grandfathers and grannies as they decide my fate. We are in a one-room hut with a packed earth floor and the grainy sensation of the dirt against my toes – the only thing I allow to squirm in my discomfort – is an intense and welcome distraction.

They announce my apprenticeship to the village’s Wise Old Woman, a healer and shaman, someone revered and somewhat feared by the other villagers. I am honored – and utterly intimidated. Using a long, finely made silk scarf they tether us together at the ankle. Until my apprenticeship ends, I will never be more than ten feet from her. She doesn’t intend to actually instruct me in anything. She will teach me by keeping me in her presence to watch, listen, assist, and ask questions.

This dream taught me I had to give up thinking I knew anything and return to an attitude of beginner’s mind. As a consultant, I had been paid to have the right answers. As an executive coach, though my consulting expertise had value, it was often more useful to listen, observe, and then ask the right questions leading clients to their own answers. As a seasoned consultant, I was used to being a star performer, running my own show and leading my own team. As a newly-minted coach, I was a student again instead of a master, and I had overlooked the art of invisibly supporting someone else, of being the team.

Most important, I was reminded once again that real learning always happens outside our comfort zone — a humbling place where success isn’t certain. One sign that I am daring enough and stretching toward the highest expression of my calling arrives when I experience that same mixture of awe and delicious terror I felt as a young village girl with knobby knees and dirty feet, meeting my teacher for the first time.

If you or your team are recovering from a particularly painful misstep, contact me to discuss how to turn that event into a powerful learning experience, one you can build on for future success.

E. Ann Hollier, Ph.D.

E. Ann Hollier, Ph.D.
Managing Partner
The Cogent Executive LLC

Ann Hollier provides strategic consulting and performance coaching to high achieving senior executives and management teams. She specializes in change management, strategic planning and implementation, leadership development, and building world-class collaborative teams. Learn more at


E. Ann Hollier, Ph.D.My Favorite Mistake