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