Leadership: Chess, Not Checkers - Geoff Stewart's Leadership 30

About this episode

Chris Workman discusses leadership principles with Geoff Stewart, emphasizing the importance of culture and long-term thinking in leadership.

♟️ Are you playing chess or checkers? If you are an aspiring leader—or even a seasoned one—you need to stop what you're doing and listen to this. I just sat down with an online audience and Chris Workman, Chief of Police at the Cheswold Police Department, for our latest Leadership 30 session. Chris brings a raw, authentic style that cuts through the noise and hits home. The core message? Culture doesn't live on this 40-minute deep dive, Chris challenges the "checking the box" mentality and explores what it actually takes to play the long game. We covered some heavy hitters that every leader should keep on their desk: 🔹 Compliance is not culture. Activity is not progress. Completion is not transformation. 🔹 Watch what you tolerate. People don’t just listen to what you say; they watch what you allow. 🔹 The true measure of leadership. It’s not about how indispensable you are, but how prepared others become because of you. After listening to this, you’ll be asking yourself: Am I a checkers player, or a chess player?

People in this episode

Host: Chris Workman

Guest: Geoff Stewart

Topics covered

• leadership
• organizational culture
• personal development
• long-term strategy
• compliance vs culture

Keywords

• leadership
• culture
• checkers
• chess
• transformation
• progress
• compliance
• mentorship

Mentioned in this episode

Organizations: Cheswold Police Department