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Working through Your Leadership Vulnerability

Hello Reader

Leaders who seek my help aren’t struggling with skills. They deal with personal challenges. They handle vulnerability, accept uncertainty, and make choices when the path isn’t clear.

These leaders are CEOs, chief people officers, chief marketing officers, and chief learning officers. They hold top positions in their organizations and excel in their fields. They intuitively sense when something is wrong.

They lead discussions well with their teams. They mentor effectively, knowing when someone should advance or move on. Their insights run deep. Yet, they often grapple with one key question:

"What do I do in moments of uncertainty?"

Working with these leaders requires patience. The urge may be to rush in with solutions. However, that approach often doesn’t serve them well.

The goal is to highlight multiple paths and allow space for exploration. Leaders have strong pattern-matching skills. They don’t need answers handed to them; they need clarity to see their way forward.

Leaders make decisions confidently every day. Their uncertainty arises from the bigger picture—questions that extend beyond quarterly goals. They ponder: Where does my career go from here? What legacy do I want to leave? Who do I want to be as a leader? What truly matters in this next chapter?

These questions are vulnerable because there's no clear path, no playbook, no best practices, and certainly no five-step guide.

This is where even the most capable leaders struggle. If you see yourself in the words above, practice small moments of vulnerability.

Perhaps the most important leadership skill isn’t having all the answers. It’s having the courage to embrace uncertainty, explore it, and trust that clarity will come from genuine inquiry.

So, how do leaders work with vulnerability? It’s practical and requires practice.

It begins with creating time for reflection. Regularly stepping away from urgent decisions, even for 30 minutes a week, allows space for unresolved questions. This isn’t about finding solutions; it’s about being present and becoming comfortable with uncertainty.

• Choosing the right sounding board is crucial. A coach, mentor, or peer should help explore what you are facing without rushing to fix things. Someone who can hold space for uncertainty is invaluable.
• Naming uncertainty aloud has power. Sharing with trusted colleagues, "I’m not sure which way to go," is often better than pretending to know. It gives others permission to be human too.
• Practice smaller vulnerabilities first. Admitting not knowing something in low-stakes situations builds resilience for bigger challenges. Vulnerability strengthens with use.

Another key practice is separating decisions from identity.

• Uncertainty about a path forward doesn’t reflect your competence. The best leaders can hold both feelings: uncertainty and capability.
• Curiosity about resistance is essential. When you feel that knot of uncertainty, ask, “What am I terrified of?” Often, it’s not the decision itself, but what it means for your legacy, relationships, or growth.
• Lastly, give yourself permission to evolve. What worked in past roles may not fit anymore. That’s growth, not failure. Who you were five years ago doesn’t have to define who you are today.

This is where true work happens. This is where transformation begins.

Yours,

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