Breaking Through Perfectionism: Coaching Leaders to Embrace Calculated Risk
As leaders, we often place bets on promising talent – individuals who show potential but need to grow into roles that stretch their capabilities. Recently, I've been working with a manager who exemplifies both the promise and challenges of this approach.
The Situation
This leader has done well in many respects. He's organized his team effectively, and they're delivering meaningful value to the organization. From most external measures, things are progressing adequately. Yet I can see he's capable of much more – if only he could break through a particular mental barrier.
His challenge? Perfectionism.
He has a strong tendency to want to understand all variables before making decisions. He seeks complete information and certainty before taking action, even when the stakes are relatively low. While thoroughness is valuable, this pattern means he frequently misses opportunities that require timely action.
The Perfection Paradox
This pattern represents what I call the "perfection paradox" – when a strength becomes a limitation. The very qualities that make someone reliable and thorough can, when overextended, create unnecessary constraints.
In our case, his methodical approach means:
Decisions that should take days stretch into weeks
Team members wait for direction when they could be moving forward
Innovation opportunities pass by while analysis continues
His growth as a leader plateaus as he avoids the uncomfortable learning that comes from calculated risk-taking
The Coaching Conversation
I recently had a direct conversation with him that addressed this dynamic. I acknowledged his strengths while highlighting the opportunity for growth:
"You're doing a good job. Your team is taking shape and responding well to your leadership. I can see that they respect your guidance and direction. But I also know you have more to offer than what we're currently seeing. Your tendency toward perfectionism is holding you back from making your full impact."
We discussed specific situations where he already possessed sufficient information to make decisions that fell squarely within his authority. I emphasized that the work in question wouldn't sink the business if it wasn't executed flawlessly – making it an ideal opportunity for calculated risk-taking.
His response was encouraging. He appreciated the feedback and expressed willingness to work on this limitation. But I recognized something important: awareness alone wouldn't be enough. He's too deeply embedded in his current thinking patterns to make this shift independently.
Beyond Feedback: Creating a Development Partnership
This situation highlights an important truth about leadership development: meaningful change rarely happens through feedback alone. When someone has operated successfully using certain patterns for years, those patterns become deeply ingrained. Shifting them requires more than intellectual understanding – it requires structured support and partnership.
So where do we go from here? Several approaches can help leaders in this situation:
1. Create graduated risk opportunities
Identify decisions with progressively increasing stakes but still within a "safe to fail" zone. Start with low-consequence decisions where the leader can practice making calls with incomplete information, then gradually increase complexity.
2. Establish reflection structures
Schedule regular debrief sessions to examine decisions – both those made and those delayed. Help the leader recognize patterns in their thinking and evaluate actual (not imagined) consequences of different approaches.
3. Shadow decision-making
Initially, walk through the decision-making process together. Verbalize your thinking to demonstrate how you assess information sufficiency and risk tolerance for different scenarios.
4. Develop decision frameworks
Help the leader create personal heuristics for determining when they have "enough" information. Different decision types require different thresholds of certainty.
5. Celebrate productive failure
When the leader takes appropriate risks that don't yield perfect outcomes, celebrate the attempt and learning rather than focusing exclusively on results.
The Bigger Picture
This situation represents a common challenge in leadership development. The transitions between leadership levels often require abandoning or modifying the very behaviors that created success at previous levels.
In this case, the methodical, detail-oriented approach that likely made this individual successful as an individual contributor now limits his effectiveness as a leader of others. His growth depends on developing new mental models about risk, delegation, and decision-making under uncertainty.
As his coach and leader, my responsibility goes beyond simply providing feedback. It extends to creating the conditions that make transformation possible – providing both challenge and support in the right measures.
The journey continues, but I'm optimistic.
— Casey
