A Tale of Two Leaders: Readiness to Grow

Last week, I had two very different coaching conversations. Both were with experienced and capable business owners and leaders. And yet, their relationship to growth, vulnerability, and self-reflection couldn’t have been more different.

One leader wasn’t ready. The other was already walking the path.

These conversations reminded me that coaching isn’t about asking powerful questions or guiding someone to an "aha" moment. It’s about honouring where someone truly is and helping them feel safe enough to meet themselves there.

When Reflection Feels Like a Threat

The first leader was visibly uncomfortable. As I asked questions—gently, with care—they began to shut down. At first, I thought I could keep going. I trusted the process. But something felt off. My intuition saw it before my mind did: a wall was going up with each question I asked.

Eventually, I had to pause the conversation altogether. I said something like,
“Let’s take a moment. I sense that this might feel like too much right now.”

To their credit, the leader was honest. They said they didn’t know what they needed. They were beginning to recognize that something emotional was happening, but they couldn’t quite put their finger on it yet.

That’s when I realized what they needed wasn’t insight or reflection. They needed psychological safety. My curiosity, while well-intentioned, had landed as a threat. And their wall? It wasn’t resistance for the sake of being difficult. It was self-protection.

And I had to respect that.

When the Door is Already Open

Later that week, I met with another leader. This person was leaning into the discomfort, asking themselves thoughtful questions, and showing compassion not only to others but also to themselves.

They said things like:

• “I felt triggered when that feedback landed. Why?”

• “How might I create more openness in my team?”

• “Where can I take responsibility without beating myself up?”
  

Their body language softened. Their self-awareness grew. They weren’t just open to growth. They were actively reaching for it.

The Limiting Story We All Carry

Both experiences reminded me of something I read from Ken Neilson:

“Transformation is the process of getting to know your default story and loosening your grip… You begin to see the limitations of any story and find the courage to step out of habitual ways of interpreting experience.”

That’s the real work. Not changing who we are, but loosening our grip on the stories we believe we have to be.

One leader was still holding tightly to their default story.
The other had started to notice theirs and gently peel it back.
The first leader wasn’t behind. They were just in a different place on the path.

Checking in With Myself, Too

After the first session, I felt frustrated. I wanted to help. I care deeply about what I do. But I had to be honest. I was also disappointed, not in the leader, but in myself.

I had to remind myself that coaching is never about forcing transformation. It’s about creating the conditions where it might arise. When I set aside my desire to be effective, I was able to reconnect with what that leader truly needed: space, care, and presence.

After the second session, I felt energized. But I held that feeling lightly, too. It’s not about me. It’s about where each person is willing or ready to go.

The Bigger Invitation

Not everyone is ready to transform, and that’s okay. What matters is creating a safe enough space for someone to start exploring.

Sometimes the bravest thing we can do is pause. Hold back. Let someone breathe.
Because when they feel safe enough to loosen their grip on that default story, that’s when growth begins.

And for us, as coaches, leaders, and humans, the invitation is the same:

• Be curious, but not forceful.

• Be present, not attached.

• Be brave enough to pause, and soft enough to stay.

Coming Next: Part 2 – Owning the Story

What happens when leaders face the hard truths about their identity and step into personal responsibility?

This piece will be Part 2 of a 5-part series: “A Tale of Two Leaders,” reflections from real coaching moments that explore contrast, growth, and the human side of leadership.

About the Author
Karas Wright is the founder of Wright Step Coaching and Certification Manager at Level 52. She helps business owners, leaders, and high-performing professionals navigate change, reconnect with clarity, and lead with courage.