We recently launched our new podcast, Leading Edge, and I had the pleasure of interviewing our very first guest, Jeff Sesol. Jeff is a coach, entrepreneur, and the author of The New Leadership Landscape. We covered a lot of ground in our conversation, but there were a few themes that stuck with me long after the recording ended.
The first was Jeff’s perspective on what it actually means to lead today. He shared that 75% of the workforce is now made up of millennials, and many of them have been promoted into leadership roles without the tools or preparation to thrive. They were strong individual contributors, but when it comes to managing people—it’s a different skill set altogether. This resonated deeply. At Fairwinds, we see it all the time: well-meaning leaders who are overwhelmed, unsure how to build trust, or stuck in the trap of “it’s just easier to do it myself.” These aren’t bad leaders. They’re just new to leadership in an era where what worked 10 or 20 years ago doesn’t work anymore. Jeff used a great metaphor that I haven’t stopped thinking about. He described going skydiving for his 40th birthday, and how everything felt out of control until he “pulled the chute” at 5,500 feet. Suddenly, he could breathe. He could see. He knew where he was and where he was going. That image has stuck with me. How many leaders feel like they’re in free fall every day? Pulled in a dozen directions, unsure what to focus on, reactive instead of intentional. Jeff challenges leaders to “pull the chute” once a week—pause, breathe, and work on the business instead of just in it. That kind of reflective time is often seen as a luxury. In reality, it might be the difference between burnout and clarity. Another part of our conversation that hit home was about trust. Jeff pointed out how many workplaces still lack psychological safety. People are afraid to speak up in meetings. Leaders feel pressure to have all the answers. But that approach is outdated. Today’s strongest leaders admit when they don’t know something. They ask questions. They invite ideas from the people closest to the work. In Jeff’s words: leadership is no longer about having all the answers—it’s about creating space for others to bring theirs forward. We also touched on emotional intelligence—a topic I’m personally passionate about. Jeff made a powerful point: when something happens at work, the immediate emotional reaction we have is often about us. But leadership isn’t about us. It’s about the people we serve. Great leaders know how to take a beat, check their emotions, and respond in a way that supports—not derails—the people around them. This isn’t easy work. As Jeff reminded me, delegation takes time. Building trust takes intention. And slowing down to speed up feels counterintuitive in a world that celebrates busy. But if we want to lead people well—not just manage results—we have to make room for that kind of leadership. I’m grateful to Jeff for kicking off our podcast with such honesty and clarity. If you’re feeling the pull of the old leadership playbook but know it’s not working anymore, you’re not alone. This is the work. And we need more leaders willing to do it.