We live in a world increasingly characterized as full of wicked problems, which are highly complex, ambiguous, and divergent problems that can never be completely solved. Moreover, the paradigm of complexity has begun to challenge the enduring mechanistic worldview. While there seems to be a sort of general agreement that such a paradigm shift is both important and well-founded, this article cautions against its premature wide-scale application in leadership education. Instead of a purely theoretical approach, we give a voice to three leaders who our earlier research led us to categorize as Chaos Pilots. They all share three characteristics. Each holds a senior leadership position. Each has a deep understanding of chaos theory, complexity thinking, or the concept of wicked problems and, most importantly, each has used that understanding to develop their leadership style. Our aim is not to offer any definitive lists of bullet points for resolution, but to draw from the experiences of these real leaders. We are especially interested in how such leaders who share a worldview of complexity sciences and have a highly attuned understanding of the nature of wicked problems actually go about transforming their leadership style.