His problem wasn’t unique.
Each of my Do What You Want books I open by telling a story about two business leaders, Gary Cohn and Jeff Bezos, at similar crossroads.
Bezos was at DE Shaw, wondering do I leave this great job to build the everything store. Cohn had been sitting as president of Goldman Sachs with his eye on the CEO seat, thinking about how to ascend or make a move.
The executive sitting next to me on the plane was in the same bind.
From the ground level he’s climbed his way to the near top of a towering company, where he sits an arms-length from the corner office.
Unclear of how long it will be before the CEO retires, and facing plenty of internal competition for the top job, constantly he’s asking himself…
Do I Stay Or Do I Go?
For most of the flight we were busy being anti-social on a plane, but as the flight attendants began preparing the cabin to land at Newark, we started talking.
“So, what do you do?” he asked.
“I do what I want” is my playful answer, but wanting to avoid all that I dodged his question, “I’m a consultant. How about you?”
Like most top executives, unsatisfied with my evasive answer he went deeper, “What type of consulting?”
“Our consulting firm is focused on systematic winning in your business, but my work is far more personal, working with leaders in getting what they want.”
“I’m a leader, I want to get what I want,” he half-joked, “I wonder if you’ve had any experience with this type of problem I’m facing…”
Game On…
Often when people present problems to me they’ve spent so much time wrapping themselves around the axle that they think their problem is super complicated and unique.
Vista Equity Partners crushes it because they figured out that the types of companies they buy can be optimized the same way, and our problems are much the same.
Sitting back and taking a big sigh, he told me how much he loved his job, how his career had been a rocket ship, but, now, he found himself stuck at a crossroad…
Like an actor taking a gulp of air before delivering his big line, slowing his voice and looking me deep in the eyes, he said, “I just don’t know if I should stay in my job or leave to start this new venture…”
Within 15 seconds I could see exactly where he was stuck.