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Leadership lessons from real, live leaders

4 min read


In leadership and management, we love to look at best practices. In leadership literature, we love to look at the people themselves for insights into what makes a great leader. People are so interesting!

Here are my top-line take-aways from some interviews I’ve done recently with a diverse group of leaders including a newly minted chief operating officer, the president of a boutique ad agency, an Air Force lieutenant general and the chief of security for Microsoft. Despite the differences in their responsibilities, their wisdom boils down to similarities we can all learn from.

Leaders are problem solvers. Leaders speak more frequently about their challenges and how they overcame them than the average employee, in my experience. They’re more conscious of the problems because they’re intensely aware that it’s their job to fix them, and when they succeed, they take pride in a problem well-solved. Patricia Koopersmith, COO at The Clearing, described her strategy for seeing possibilities in every problem this way: “I’ve learned to ask ‘why not’ instead of always asking ‘why.’ ”

Leaders master many styles. Leaders know that different situations require different reactions from them and so they become intentionally adept at learning to respond in the most useful way to any given situation. They’ve learned that their effectiveness isn’t always about what they want or like to do, but how well they read and react to the reality at hand. This requires them to go outside their comfort zone and learn new ways of being. And their comfort zones aren’t always what you’d expect. In my interviews, it was the ad agency president who admitted to being a naturally command-and-control type and the Air Force general who acknowledged that her starting point was collaboration. Karen Riorden, president at Smith Gifford, said she found her success in “flexing my leadership style back and forth all day long. [I like] being the bad cop like in the financial contract conversation I’ll have this afternoon, and then sitting down to do a six-month review and mentoring session with a junior account person.”

Leaders care, genuinely and passionately, for others. Every leader I spoke to spent a good portion of the conversation talking about how much he or she enjoyed mentoring and developing talent. From recruiting trips to interviews, to informal mentoring, each of them saw themselves in an ongoing chain of human capital. They each acknowledged gratitude for those who’d helped them and expressed a deep commitment for helping pull up the next generation of leaders and high-performers. Mike Howard, Microsoft chief of security and ex-CIA agent, took to heart the wisdom of one of his mentors and internalized this truth: “Once you’re in a position of authority, you become more selfless than selfish. You need to take care of people.”

Leaders are on an inner journey. More than most, leaders have a meaningful view of themselves over time and in relation to others. They self-reflect easily and openly, and acknowledge failure and weakness as important stepping stones on their path to success. This ability to take responsibility for their choices and let go of excuses is a skill that must be developed consciously. These leaders I spoke to reached a point in their career where they could not rely on mentors and superiors to smooth the way, and that is when they took ownership of their journey. A case in point is Air Force Lt. Gen. Judith Fedder, who discovered that even when she has stars on her shoulders, she would be confronted with difficulties that required her to stretch beyond the rule sets and priorities and people she was used to. Reflecting on these trying times, she summed up how she viewed her inner challenges this way: “Some things have to be hard to be worthwhile.”

I’m very grateful to these four amazing people for sharing their wisdom so I could pass it on to you. It is my hope that if you are reading this, their stories give you courage to stay on the difficult, but rewarding, path of leadership. I’m always looking for new interview subjects to profile. If you have an important leadership story to tell, contact me. Maybe your story is next.