356. The Leadership Skill Nobody Trains You For

Key Takeaways

• Leaders don’t actually struggle with risk — they struggle with uncertainty.
• Risk can be measured and defended; uncertainty cannot.
• Delaying decisions often feels strategic, but it’s usually fear in disguise.
• Waiting doesn’t reduce uncertainty — it postpones accountability.
• AI increases uncertainty by accelerating change, not by creating clarity.
• Leadership success depends on discomfort tolerance, not information volume.

Actionable Insights

• Stop waiting for “enough data” — clarity rarely arrives in uncertain environments.
• Make smaller, reversible decisions instead of big, irreversible bets.
• Shorten feedback loops to learn faster instead of planning longer.
• Communicate direction instead of certainty.
• Shift from prediction-based leadership to learning-based leadership.
• Normalize “we don’t know yet” as a leadership strength, not a weakness.

Leadership Challenge