Skip to content

The Leader as Chief Skeptic

Luther Bruce wasn’t necessarily a skeptic.  But he asked hard questions that no one really wanted to hear. So he sometimes came across as one. And early in my career, I learned that “The Leader as Chief Skeptic” isn’t a bad thing.

My first corporate position was as the Director of Development for a private school – I was in charge of fundraising for a school where I had taught and coached for a number of years.  The prior development officer had moved on, it was time for a change, I was ready to move out of the classroom, one thing led to another, and I went from coaching football to sitting in board meetings, listening to boring reports.

The highlight of many of these board meetings, at least for me, was when Luther, one of the school’s board members, started asking questions.  His questions didn’t usually come early in the meeting, and they weren’t ever vindictive or accusatory. They were just hard.  It was very evident to me that he had been listening to the various reports, processing the discussions and decisions, and looking for the holes in the decisions that would expose the school to risk.

At times I suspect Luther was not overly popular.  Just when everyone thought the meeting was wrapping up and they were going to be able to call it an early meeting, he raised his hand. Many times his questions led to lengthy discussions and decision reversals.

And most importantly, his questions led to better decisions.  Decisions that were more future-oriented and future-proofed.  Decisions that were in the students’ best interests.  Decisions that kept the school on a strong financial and accreditation basis.

Good decisions came from hard questions.  Luther didn’t intend to be a skeptic.  He just wanted to have us think thoroughly through our actions.

That’s where you and I come in, leader.  Increasingly I find myself being skeptical.  I’m skeptical of promises. I’m skeptical of vendors. I’m skeptical of contracts and agreements.  I’m skeptical of research. I’m skeptical of new initiatives.  Sometimes I’m just plain skeptical.

I don’t mean to be a skeptic, but I think I come across that way.  Recently I was at the global owners’ forum for the franchises my wife and I own.  The master franchisor was presenting some of the new initiatives that had been rolled out recently and would be rolled out in the near future.   I raised my hand.  I had some questions.  I was skeptical about some of these initiatives.  And once I started asking questions, it became evident that I wasn’t the only one who had concerns. There was a chorus of questions and comments that came out from other owners.  We ended up having a much richer conversation, and the master franchisor had a much better sense of the concerns we all had.

Tomorrow I’m heading into a meeting with a number of our subordinate leaders. They will be presenting ideas for upcoming marketing and customer engagement activities.  I’ll find myself asking a lot of questions.  I hope I don’t come across as a skeptic.  But that’s my job.