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Leading from Fertile Doubt

por Alfredo Carrasquillo

The times we are living in are not times for illusions or certainties. We may even feel nostalgic for periods when it was enough to manage risks—to have scenarios ready to respond to the emergence of what was already known. Today, however, what truly matters in the practice of leadership is not risk management, but the management of uncertainty; that is, of what is largely unprecedented and unknown.

The problem is that when we allow ourselves to be trapped by the search for impossible certainties and guarantees, we inevitably choose too late—and therefore poorly. This is the gravity of a familiar practice: analysis paralysis, overwhelmed by anxiety and obsessive doubt.

Yet the opposite is equally risky. Confusing haste with agility and clinging to solutions that worked in the past—believing that we have already been there and that we possess a clear map to move forward—also exposes us to significant missteps.

In harsh and unfamiliar times like those we are experiencing, which demand that many lead teams and people under complex conditions, I am convinced that the key lies in leading from fertile doubt. By this, I mean an openness to inquiry that does not rush toward fabricated certainties, but instead honors the necessary pause for rigorous reflection, strategic analysis, scenario planning, and critical thinking. The latter has become almost a cliché in leadership discourse yet remains no less indispensable in this historical juncture.

That said, fertile doubt does not emerge from solitary or monastic reflection. It is an invitation for leaders to adopt a style centered on facilitating critical conversations and deep dialogue; to encourage a clash of ideas that does not fear disagreement or difference but rather recognizes in them the potential to activate collective genius, to generate distinctions capable of transforming our structures of interpretation, and to open unprecedented paths for shared action.

In this way, the commitment to fertile doubt that fuels productive conversations, not only fosters innovation—at a time when repeating the same approaches is no longer sufficient—but also nourishes the construction of a more robust we. As I argue in my book Equipo en construcción, perdonen las molestias, this strengthens a sense of belonging and commitment to the shared pursuit of solutions.

Leaders who seek to sell—and become trapped in the narcissistic performance of—the idea that they know everything and have all the answers deprive themselves of the richness that can only emerge from collective intelligence.

Hence my invitation is clear: leading from fertile doubt is not a sign of weakness or insecurity. On the contrary, it is a commitment to shared responsibility—to navigating uncertainty with greater clarity, articulating possible futures, and, in the process, building a we capable of sustaining them.