Power has a peculiar effect on judgment. The higher you climb, the quieter dissent becomes.
Your board might nod. Your team might smile. Your family might defer. But who actually stops you when you’re about to make a costly mistake?
Consider Theranos. Elizabeth Holmes surrounded herself with impressive board members—Henry Kissinger, George Shultz, James Mattis. Yet none of them had the technical knowledge or courage to challenge the fundamental premise of her company. They were ornamental, not operational.
Or take WeWork’s Adam Neumann, whose board enabled increasingly erratic behavior until investors finally said enough. By then, billions in value had evaporated.
The pattern repeats across industries. Leaders ascend, feedback diminishes, and blind spots expand.
The Isolation Trap
Success breeds isolation. People tell you what they think you want to hear. Criticism gets filtered through layers of management. Bad news arrives late, softened, or not at all.
Jim Collins found that great companies have leaders who create a “culture of discipline” where truth-telling is rewarded, not punished. But discipline starts with structure.
Building Your System
Every leader needs three types of challengers:
Someone with domain expertise who can question your technical assumptions. Someone with financial acumen who can challenge your numbers. Someone with moral courage who can question your character.
These aren’t yes-people or devil’s advocates playing theater. They’re individuals with skin in the game who genuinely care about outcomes over feelings.
The best leaders don’t just tolerate dissent—they systematically create conditions for it. They reward the messenger, even when the message stings.
Your success depends not on being right, but on being corrected quickly when you’re wrong.
