Paola Cecchi-Dimeglio

Recognizing the value of rethinking is one thing—making it a habit is another. Many leaders struggle with revising their opinions, not because they lack intelligence, but because they lack the right tools to challenge their own thinking. Organizations, too, often default to past strategies rather than embracing a culture of adaptability. If you want to develop the skill of rethinking—and build a workplace where learning and adaptability thrive—you need a structured approach. The best leaders use specific strategies to train themselves and their teams to challenge assumptions, embrace hange, and pivot when necessary.

Challenge Your Own Assumptions Regularly

The first step in developing a rethinking habit is to proactively question your own beliefs. Leaders who regularly challenge their own assumptions make better decisions and avoid costly missteps. One simple yet powerful exercise is to ask yourself:

- What would convince me that my current strategy is wrong?

- Am I relying on past success to justify current decisions?

- If I were an outsider evaluating this decision, what weaknesses would I see?

This kind of self-inquiry forces leaders to separate ego from strategy, ensuring that decisions are based on the best available information rather than past habits.

Surround Yourself with a Challenge Network

Many leaders unknowingly create echo chambers—surrounding themselves with people who reinforce their existing beliefs. To avoid this trap, Adam Grant suggests building a “challenge network”—trusted colleagues who provide constructive dissent rather than just support. A strong challenge network consists of people who will ask tough questions, present alternative viewpoints, and call out blind spots. Leaders at Pixar, for example, engage in braintrust sessions, where teams critique film ideas early in development. These candid discussions lead to better storytelling because they force directors to rethink and refine their work.

Make Rethinking a Teamwide Practice

A leader’s ability to rethink is only as effective as the culture they create. Organizations that embrace learning over rigid certainty perform better in volatile environments. Satya Nadella transformed Microsoft’s culture by shifting it from a “know-it-all” culture to a “learn-it-all” mindset. By encouraging curiosity, rewarding adaptability, and fostering open discussions, he created a workplace where rethinking is expected, not resisted.

Great leaders don’t see their beliefs as fixed truths—they treat them like hypotheses to be tested and refined. By questioning their own assumptions, building challenge networks, and fostering cultures of continuous learning, they create organizations that don’t just survive change but thrive in it.

Forbes