Best Leader. Worst Leader. What Did You Learn and How Do You Lead?

A few days ago, I delivered a workshop (virtually) for a Vistage Chief Executive Group in Colorado Springs. Randy Welsch, the Vistage Chair who led the group, started the meeting with a short inclusion exercise. He broke everyone into small groups to answer four questions:

1. Who was the best leader you ever worked for?
2. Who was the worst?
3. What did you learn from both experiences?
4. How do these experiences influence the way you lead today?

Even though I was the guest speaker, Randy was kind enough to approve my request to participate so I could build rapport with the members before my presentation.

I found the exercise extremely enlightening, as it helped me reflect on my experiences and also opened a window into the members’ leadership journeys. I found it so compelling that I want to share it here and suggest you try it yourself and perhaps introduce it to your group or team.  Here were my answers to the four questions.

Who Was the Best Leader You Ever Worked For?

It was Joe Grimaldi, former CEO of Mullen (now MullenLowe), a Boston-based advertising agency. Here’s just one story to paint the picture. I participated in a new business pitch to a major prospective client in New York. Grimaldi, himself, was part of the presentation team from the get-go. We all saw him as a part of the team, never apart from it. His active involvement in the presentation demonstrated to the prospect that its business mattered to the agency.

Later Grimaldi would show us that his team was important to him, too. After the presentation, he received an urgent call that took him out of the room as we were packing up before flying back to Boston. None of us gave it a second thought until we got home that night. Before going to bed, I checked my email. I discovered a note from the CEO that he sent to everyone on the team apologizing for being pulled away, explaining that he failed us as “Chief Encouragement Officer.”  He applauded everyone’s collective effort and stated that regardless of the outcome, we have every reason to celebrate the work we did together. Since we eventually won the business, it meant we celebrated twice.

Who Was the Worst?

Between my college graduation and the start of a job I had accepted with US Senator Paul Tsongas’ re-election campaign, I needed to make some money and find a car to drive. Selling cars at a local Ford Dealership would help me achieve both. I could make decent money after a 30-day trial period and drive a brand-new automobile. While this may sound ideal, it would come at a price. The sales manager, Roy, was a chain-smoking tyrant, and he was the one running the show on the sales floor.

For example, anyone exhibiting even a hint of inactivity in their eyes would get a phonebook thrown in their face, upon which Roy would scream, “Call 20 landscapers and sell one of them a truck!”  He terrorized customers and employees alike.  You’ll find specific stories of Roy’s behavior in my most recent book.  That said, and in fairness to Roy, he was like a turtle.  Hard on the outside, soft on the inside. When he cared to show it, he had a big heart. Roy didn’t lead people the way he did to be cruel; it was the only way he knew how.  I don’t have the luxury of that excuse because he taught me how to lead by showing me precisely what NOT to do.

What Did I Learn from Both Experiences?

Joe Grimaldi was masterful at achieving the delicate balance of challenging people to achieve their potential and supporting them every step of the way. We were all in it together.  He didn’t light a fire under people like Roy; he did what The Leadership Challenge authors Jim Kouzes and Barry Posner described as one who lights the fire within. Grimaldi inspired everyone who worked for him. Roy showed me that yelling and screaming were not prerequisites for leadership. They both helped me learn that leaders who prize clarity and transparency, care about relationships over transactions, favor inspiration over motivation, and lead by serving others are the types of leaders most people will follow to the ends of the earth.

How Do These Experiences Influence the Way I Lead Today?

Because of what I’ve experienced about leadership from Joe, Roy, and from the many books I’ve read by Kouzes and Posner, I don’t teach during my workshops; I create conditions for learning – this has become my brand of leadership.  Through this practice, I’ve discovered the value of Kahlil Gibran’s magnificent quote: “If he is indeed wise he does not bid you enter the house of his wisdom, but rather leads you to the threshold of your own mind.”  I have Joe, Roy, Jim, and Barry to thank for bringing me to my leadership threshold.

How about you?  How would you answer these four questions?

Written by Leo Bottary. Have you read?
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