Thoughtful Leadership
Summary: It’s easy to look at the world right now and only see division. Political polarization. Wars. Cultural battles. Anxiety about artificial intelligence. Generations arguing over what matters most. People choosing sides before they’ve even finished listening to each other. We keep asking, “How did things get this bad?” I wonder if there is another…
Summary: What do you do when no choice feels comfortable? Ed Sheeran found out very publicly. Read on for my thoughts on what to do when you’re caught between a rock and a hard place. Dear Dr. Sylvia, There is so much polarization in our world right now; we can’t even go to a concert…
Summary: What if meaningful organizational change begins not with a grand strategy, but with a leader who notices what others may have overlooked? Hanneke Faber’s leadership offers a powerful example of how curiosity, adaptability, and a willingness to challenge the familiar can create meaningful transformation. Some leaders enter an organization with a five-year plan already…
Summary: What if the employee who keeps reverting to old behaviors isn’t failing to change, but is actually showing the first signs of transformation? Discover how recognizing the small GLIMMERS of progress can help leaders balance accountability with patience, avoid triggering old patterns, and allow space for meaningful growth to take hold. Dear Dr. Sylvia,…
Summary: What if the things that bother you most are actually trying to get your attention? Gloria Steinem’s life offers a powerful reminder that change often begins with a GLIMMER—a question, contradiction, or moment that makes you stop and wonder why things are the way they are. Discover what happens when you pay attention to…
Summary: Your team may look terrific when everything is going well. People collaborate. Meetings are cordial. Deadlines are met. Everyone talks about trust, transparency, and “being one team.” Then the pressure hits. A major client threatens to leave. Revenue falls short. AI changes someone’s role. Instead of doom and gloom, here is a better way…
Summary: What happens to leadership when artificial intelligence can analyze faster, process more information, and produce answers in seconds? Perhaps the answer is surprisingly simple: We have to become more human, not less. Microsoft’s CEO has something to teach us about empathy, self-awareness, and human leadership in the age of AI. Satya Nadella, Chairman and…
Summary: There’s a sentence I’ve heard in executive team meetings, family businesses, and coaching conversations for decades: “That’s just how I am.” That sentence is almost guaranteed to shut down conversation and creativity for good. Here is another way to think and respond. Dear Dr. Sylvia, My leadership team is stuck in an “either/or” argument…
Summary: Dolly Parton has spent a lifetime covered in rhinestones. Yet somehow, she has never appeared to hide behind them. That may be one of the most remarkable things about her. In a culture fascinated by status, image, followers, titles, money, and the carefully polished version of ourselves we present to the world, Dolly Parton…
Summary: What if one of the worst moments in your career actually pointed you toward the work you were meant to do? Long before Oprah Winfrey became Oprah, she was a 22-year-old television journalist who moved to Baltimore to co-anchor the evening news at WJZ-TV. Oprah has written and spoken openly about those early years.…