There are moments in leadership development where something shifts from concept to lived experience. At our Vistage meeting a few months ago, I witnessed one of those moments – and it challenged how I think about growth, problem-solving, and what it really takes to lead. It started with courage.
The Moment of Choice
At that meeting, Mark Altman introduced his Courageous Conversations method to the group.
None of us had experienced it before.
One of my members volunteered to apply it to a real and sensitive issue inside her organization – something involving tension with another member of her executive leadership team.
You could see the hesitation. She paused. She glanced around the room.
We all looked back – not pushing, not pulling – just present. There was an unspoken recognition: this is real.
What held her back wasn’t logic. She knew there was something to gain.
What held her back was fear – because the risks were real:
- It could expose a blind spot in her leadership
- It could become emotional
- It could surface tension in front of her peers
Most executives don’t go there – especially not in a group setting, but she did. And that decision mattered more than any technique that followed. Our group meeting isn’t like most boardrooms. It’s safe because there’s real love in the room, empathy, and shared understanding.
The Real Issue Beneath the Surface
The challenge our member brought wasn’t simple.
She was navigating a growing disconnect with a member of her executive leadership team – someone she didn’t naturally relate to.
There were expectations around how leadership roles would contribute to the organization’s growth and culture. But instead of alignment, something else had emerged.
Functions that had once been collaborative were becoming more isolated.
What replaced collaboration wasn’t clarity – it was silence.
A kind of silence that spreads.
Long-tenured team members began to feel uncertain. People who had invested deeply in the company started to question where things were heading. Over the years, the culture began shifting – not abruptly, but subtly – from something connected and entrepreneurial…toward something more rigid.
At the leadership level, roles were becoming more clearly defined. But instead of increasing alignment, it created distance.
Our group member didn’t come in with a clear answer. Instead, she said something far more honest:
She didn’t know if she actually disagreed with her colleague. She just felt a chasm.
And she didn’t know how to bridge it.
When Authenticity Replaces Expertise
In most executive settings, this is where the advice would begin.
Someone would share a similar experience. Another would suggest a different structure. Someone else would offer a tactic that worked in their company.
And we would all leave feeling helpful, but not necessarily more understanding. This moment went a different direction.
She didn’t present a polished perspective. She didn’t try to control the narrative. She named it for what it was: a quandary.
We could feel her frustration — but even more, we could feel her uncertainty.
And then something shifted.
When Mark asked if she’d be willing to role-play the situation, she paused again…. But this time, she leaned in.
And you could visibly see the transition.
She moved from being the expert – explaining the issue – to becoming a participant in the process.
She let go.
What Resilience Actually Looks Like
As she stepped into the perspective of the other executive, something remarkable happened.
This wasn’t analysis anymore. It was immersion.
As Mark asked her questions from that perspective, you could see emotions move through her in real time – almost like waves. Introspection. Moments of clarity. Uncertainty. Fear. And then courage again.
The questions were simple. The answers were not. They required her to go deeper than most executive conversations ever allow. And what stood out most to me was this:
Mark didn’t push. He paused repeatedly and asked her:
“Do you want to go deeper? Are you willing to stay with this?”
And each time, she chose to continue. That’s what resilience looked like in that moment. Not powering through. Not performing. Choosing – again and again – to stay present in discomfort long enough for something real to emerge. I saw courage.
Meanwhile, the rest of the room was completely still. No one interrupting. No one offering advice. Just full attention – watching someone do the real work of leadership in real time.
The Shift That Changes Everything
And then… something changed.
Through that process, she began to see something she hadn’t seen before. Not just behavior, but perspective.
She started to recognize the fear, uncertainty, and pressure the other executive might have been experiencing:
- Stepping into a new role
- Being asked to formalize areas that hadn’t been clearly defined before
- Coming from a different organizational background
- Trying to establish credibility while navigating unfamiliar dynamics
What had previously looked like disconnect…started to look like orientation. What felt like resistance…could be part of someone trying to define their role.
That shift created something that hadn’t been there before: Empathy.
From Frustration to Possibility
She didn’t leave with a perfectly solved problem. She left with something more important: perspective.
Instead of feeling stuck, she saw new angles:
- Better questions she could ask
- Ways to reopen dialogue
- Opportunities to share insight without creating conflict
And most importantly: She left with hope!
Where there had been frustration and isolation, there was now a path forward.
What This Changed for Me
As a Chair, this experience shifted something for me as well. It reinforced a simple but profound truth:
Advice doesn’t create understanding.
Understanding creates change.
And real understanding doesn’t come from faster thinking or better frameworks.
It comes from:
- Courage to step into uncertainty
- Humility to admit what we don’t know
- Resilience to stay in discomfort
- And space – real space – to explore what’s actually happening beneath the surface
That’s what leadership development looks like when it’s real.
Not controlled. Not optimized.
But alive.
This article was first published in my LinkedIn newsletter, Feeding the Flame. Read the original.