Many leaders don’t actually struggle to find the right decision: they struggle to execute it. In coaching sessions, executives often present me with a dilemma, outline the options, and then admit: “I already know what I should do. I’m just not sure I can go through with it.”
This hesitation rarely comes from lack of intelligence or analysis. It comes from fear: fear of making a mistake, of being blamed, of losing status or credibility. Left unchecked, that fear becomes a brake on action. Decisions drag out, opportunities pass, and uncertainty spreads to the team.
The good news is that fear of being wrong can be managed. Confidence isn’t a personality trait you’re born with; it’s a skill you can build. Here’s how.
Reframe mistakes as information, not identity
Fear thrives on the idea that “if I’m wrong, it means I’m incompetent.” Flip that script:
- A wrong decision ≠ a wrong leader.
- Every decision produces data about your assumptions, processes, and environment.
Make this explicit to yourself and your team: “We’re running an experiment based on our best information. If it’s off, we’ll adjust.” This removes the shame element and turns learning into an asset.
Use “pre-mortems” to defang fear
A pre-mortem is a simple exercise: before acting, imagine the decision failed. Ask, “What would have caused that?” List the risks. Then ask, “What can we do now to prevent or mitigate them?”
This practice doesn’t just reduce blind spots. It also quiets the inner critic: you’ve already surfaced the worst-case scenario and built a plan for it.
Shrink the decision into a test
When a choice feels huge, break it into a smaller, lower-risk step. Instead of a full rollout, run a pilot. Instead of committing to a 12-month contract, start with 3 months. Success in small steps builds experiential confidence: one of the fastest ways to erode fear.
Normalise rapid feedback loops
Confidence grows from action + feedback. The more frequently you act, learn, and adjust, the less any single decision feels existential. Build mechanisms to check outcomes quickly (dashboards, short debriefs, client feedback). You’ll stop fearing mistakes because you’ll catch and correct them early.
Practice “fear exposure” in low-stakes contexts
Just like athletes build skill under pressure, leaders can build “decision muscle” by deliberately making and owning decisions in safe environments:
- Choose the restaurant for a team lunch without overthinking.
- Make a small budget call without extra approvals.
- Publicly state a position on a minor issue.
Each rep teaches your nervous system: “I can decide, handle the consequences, and recover.” Over time, this spills into high-stakes contexts.
Separate analysis from approval-seeking
Many leaders extend analysis not because they lack data, but because they’re hoping someone will absolve them of the risk. Recognise when your “research” is really a search for permission. Name it and decide.
From knowing to doing
Confidence is not the absence of fear; it’s the willingness to act despite it. By reframing mistakes, using pre-mortems, shrinking decisions into tests, building feedback loops, and practicing low-stakes reps, you convert fear into competence.
In my own journey from CTO to Executive Clarity Coach, I’ve seen this pattern repeatedly: once leaders stop waiting for perfect certainty and start acting with disciplined experimentation, their teams follow suit. Decisions speed up. Energy returns. Fear loses its grip.
Raido Kivikangur is an Executive Clarity Coach and former CTO (€3B+ infrastructure programmes) who helps tech and infrastructure leaders cut through decision fatigue and lead with calm authority.
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