Brooke Taylor spent more than a decade inside high-performance environments, including leadership roles at Google, before turning her attention to a question that many accomplished professionals quietly wrestle with: why does achievement so often fail to produce a lasting sense of fulfillment? In this conversation, she examines what she calls the “success wound” — the tendency to attach self-worth to performance, recognition, and external measures of success. Drawing from her own experience with burnout, addiction recovery, career advancement, and entrepreneurship, she explains how these patterns develop and why they continue to shape behavior long after professional success has been achieved.…

In this conversation with Cheryl Strauss Einhorn, the discussion examines what happens to judgment and critical thinking as AI becomes embedded in daily decision-making. Drawing on her background as an investigative journalist at Barron's, Einhorn explains how questioning assumptions and searching for disconfirming evidence shaped the development of her AREA Method for decision-making. She argues that AI should not be treated as an authority, but as a tool that requires active scrutiny and human judgment. Several points throughout the discussion: Use AI to challenge assumptions, not simply confirm them Ask for opposing viewpoints and missing evidence when using AI Verify…

Fredric Marshall spent decades helping companies including Apple, Pfizer, and Genentech solve problems in sales effectiveness, product launches, and organizational change. In this discussion, he explains why he views sales and leadership primarily as change management challenges: helping people move from where they are to where they want to be. The conversation centers on several practical ideas that shape long-term performance. Marshall argues that strong systems reduce stress because “the system is carrying the load, not you as a person or the team.” He explains why high-performing people consistently invest in infrastructure, technology, and environments that remove friction and preserve…

Kristy Ellmer has spent her career leading large-scale transformations across industries, countries, and operating environments. In this conversation, she explains why most change efforts fail — not because of bad strategy, but because organizations underestimate the human side of execution. A central idea from the discussion is the imbalance between the “what” and the “how” of transformation. Leaders spend enormous energy defining strategy, targets, and operating levers, but far less time on the behaviors and systems required for adoption. As Ellmer explains, “transformations or change are failing… on the elements of the how. It’s not because there was bad strategy.”…

Philip Jameson discusses why most organizational transformations fail despite strong strategic intent, significant investment, and broad awareness that change is necessary. Drawing on his work at Boston Consulting Group and the research behind How Change Really Works, Jameson argues that the core problem is often not strategy itself, but a poor understanding of “how humans behave during periods of change.” The conversation begins with Jameson’s unusual path into consulting through classical music and leadership at the Sydney Symphony Orchestra. He reflects on the orchestra’s temporary departure from the Sydney Opera House during its renovation and why the experience fundamentally shaped…

Management advisor and author Joe Pine explores a question that sits beneath most business strategy discussions but is rarely addressed directly: what business is ultimately for. Drawing on decades of work spanning mass customization, the experience economy, and his latest research on transformation, Pine argues that many companies misunderstand the real value customers seek and therefore stop too early in how they create value. The conversation begins with the progression from goods and services to experiences and transformations. Pine explains that transformations differ from experiences in one critical way: they must endure through time. “Memories of experiences fade over time,”…

Marc Canal, a partner at the McKinsey Global Institute, examines how long-term economic progress is built and what current shifts in AI, demographics, and productivity mean for senior leaders. He explains that consulting is less about analysis than it appears and more about trust, judgment, and the ability to frame relevant questions. Building a small number of strong relationships is more valuable than broad exposure, particularly when developing a client base. Organizations, he notes, are inherently messy. What appears structured from the outside is the result of distributed decisions and constant adjustment. The role of leadership is not to eliminate…

Amy Leneker, a former C-suite executive and advisor to Fortune 100 leaders, examines a common assumption in corporate life: that stress is an unavoidable cost of success. She argues that this belief is flawed, noting that when leaders feel disconnected from their values and priorities, “it doesn’t feel like you’re succeeding.” The discussion centers on how stress operates at three levels: individual, relational, and systemic, and why each requires a different response. At the individual level, Leneker highlights the role of unexamined “stress stories.” These are internal narratives that shape behavior without conscious choice. By repeatedly asking “why,” leaders can…

Jason Wild discusses the discipline of building and scaling businesses through careful capital allocation, operational focus, and a clear understanding of risk. He explains how leaders often misjudge growth by pursuing expansion without fully understanding the underlying economics, noting that “growth only creates value when the returns exceed the cost of capital.” He emphasizes the importance of distinguishing between revenue growth and value creation, and why many organizations confuse activity with progress. In his view, strong operators develop a detailed understanding of where value is truly generated and concentrate resources there rather than spreading them thinly. A central theme in…