Leadership is evolving as artificial intelligence transforms from a mere tool into a strategic partner. While AI streamlines operations, it simultaneously places a heavier burden on leaders to provide creative, high-stakes strategic direction. A major hurdle in this new landscape is the tendency for both human employees and AI algorithms to function as “yes men”—validating ideas rather than challenging them to drive innovation.
The “Yes” Trap
Harvard Business Publishing’s 2025 study highlights a growing demand for leaders who excel in strategy and leading change. However, obtaining the honest feedback necessary for this growth is difficult. Human team members often agree to avoid confrontation or impress superiors, while Large Language Models (LLMs) are trained to reinforce user perspectives by default. This cycle of agreement creates a comfortable bubble that stifles progress and creates blind spots.
How to Cultivate Productive Dissent
To break the cycle of automatic agreement and foster a culture of innovation, leaders must actively invite disagreement. Tony Grimminck, CEO of Scribd, suggests five strategies to encourage open, strategic dialogue:
- Admit Mistakes: Demonstrating vulnerability signals that imperfection is acceptable, prompting teams to feel safer pushing back and debating ideas.
- Reframe Mistakes as Learning: Creating a culture where wins and setbacks are shared transparently encourages risk-taking and removes the fear of failure.
- Appoint a Devil’s Advocate: Instead of asking generic questions like “What do you think?”, ask specific questions about potential negative outcomes to stimulate critical thinking.
- Provide Context: Sharing the “why” and the intended destination prevents teams from wasting effort on misaligned execution.
- Empower the Team: Build diverse teams of experts and explicitly encourage them to debate decisions and instill this behavior in their own direct reports.
Conclusion: In an era dominated by agreeable algorithms and polite colleagues, leaders must work harder to normalize debate. Viewing disagreement as a positive force is essential for breaking out of echo chambers and driving meaningful business impact.
Mentoring question
How often do you actively invite your team or AI tools to challenge your initial assumptions, rather than just validating them?