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.
I present a model of ’engagement’ to explain how strategic decision makers use different concepts simultaneously to tame wicked problems in a modern business environment. Attention is placed on ’framing’ and ’reframing’ and how this can lead to the resolution of complex problems. I analyze a longitudinal case study of a transport logistics company, where a complex problem was framed through one set of concepts, reframed by another, and eventually tamed. I argue that strategic problem solving involves an engagement of different ideas and a process of reframing to tame wicked problems. Particular attention is paid to how the key actors interacted and how these interactions influenced ’engagement’. I conclude by relating this to modern European managers and the emergent problems they face.