Jeroen De Flander: common pitfalls in strategy execution

In this episode, Roemer Visser speaks with Jeroen De Flander, strategist and Managing Director of the Performance Factory, about why so many strategies fail. Not in design, but in execution. As De Flander explains, the focus of most organizations is in the wrong place: “All the energy and focus has been going to strategy formulation.” His research shows that the real challenge lies in behavior and leadership: “Forty to sixty percent of the strategy gets lost during execution.”

De Flander describes a major mismatch between where leadership attention goes and where the real pain is in organizations. Strategy often looks strong on paper, but translating it into daily decisions is where it breaks down.

The curse of knowledge

One of the most striking ideas De Flander discusses is the curse of knowledge: the tendency of leaders to assume that others understand their message in the same way they do. When you don’t see this gap in understanding, repeating a message multiple times will not help it stick. That gap in understanding, he says, is pervasive in organizations. “Repeating doesn’t work in communication,” De Flander warns.

On securing buy-in

De Flander challenges a common assumption about strategy: that buy-in is something to create afterward. “Buy-in needs to happen in the strategy process at the beginning by involving them,” he says. “If you have to sell the strategy after you’ve made it, you’re already a few steps behind.”

Habits, not willpower

The conversation turns to what actually drives consistent execution. De Flander shares research showing that lasting change doesn’t come from effort alone: “The core of strategy execution is helping people make small choices in line with the big choice.” When that happens repeatedly, habits form. “Culture is nothing more than shared automated decisions,” he explains.

Curiosity in leadership

Asked what distinguishes great leaders, De Flander answers: “The first one that comes to mind is curiosity,” he says. “Senior leaders need to be aware that things are changing a lot. So staying curious and challenging themselves is an important one.”
Curious about how to bridge the gap between strategy and action?
Listen to the full conversation on Spotify, Apple Podcasts, or YouTube.

About Jeroen De Flander

Jeroen De Flander is an internationally recognized expert on strategy execution and AI strategy. He is a sought-after keynote speaker, and the author of several books, including his latest: Strategy Shortcut, released in July 2025. He is Managing Director of the Performance Factory, a boutique training and consulting firm in strategy execution and AI strategy. He is also the Academic Director of the Strategy Execution and AI Strategy program at TIAS School for Business and Society. 

About Roemer Visser

Host Roemer Visser is an expert on the human side of organizations and is Executive Professor and Academic Director of the Executive MBA at TIAS.

About the Rethinking Leadership podcast

Deep conversations, fresh insights—leadership, re-examined.
In the Rethinking Leadership podcast, we dive into the complexity of leadership. Whether you’re working to earn trust, to grant trust, or to inspire others with your stories, leadership is always a challenge. Guided by Executive Professor Roemer Visser, we explore new perspectives and deeper insights. Listen to inspiring conversations with thought leaders and discover surprising approaches to leadership challenges.

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