How to Stop Overthinking Decisions as a Leader
By Cristina Stensvaag, Co-Founder of LeaderReps.
Some decisions deserve deep thought. Most do not, and treating every call like a life-or-death choice is exhausting and slow. If you find yourself circling the same decision for days, the problem is usually not the decision. It is how you are sizing it.
The short answer
Sort the decision by impact and how reversible it is. If it is small and reversible, decide quickly and move on, since overthinking it costs more than getting it slightly wrong. Save your deliberation for the calls that are genuinely big and hard to undo.
Most overthinking is a sizing error
Overthinkers treat a reversible, low-stakes choice with the same weight as a permanent, high-stakes one. But a decision you can undo tomorrow does not deserve a week of agonizing. The cost of deliberating often exceeds the cost of being a little wrong. Ask two quick questions. How big is the impact, and can I reverse it? If it is small and reversible, just decide.
Cut the noise
Overthinking also comes from piling on factors until the choice disappears under complexity. The fix is to strip the decision to its core. What is the one thing that matters here. Clarity beats complexity, which is the whole point of Clarity Wins, Complexity Doesn't. A simpler frame is usually a clearer decision.
The real block is often self-trust
Frequently, overthinking is not about missing information. It is second-guessing, a reluctance to commit because you might be wrong. But leadership means deciding with incomplete data and standing behind it. Building that muscle is the subject of Trust Yourself to Decide. At some point the input stops and the choice is yours. Make it.
Read next
For the full framework, see how to make better decisions as a leader.
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