Michael came to me in the middle of a transition.
His business had scaled to $20M.
He’d installed new leaders, pulled back from some day-to-day functions, and was starting to breathe again. Then things started to wobble.
Sales felt soft. A $1.5M project evaporated overnight. The team wasn’t moving with urgency.
And suddenly, the space he had fought so hard to create felt unsafe.
So the question became:
Had he let go too soon? Or not soon enough?
At First, He Brought Business Problems to Our Conversations
Hiring.
Estimating software.
Sales accountability.
Cash pressure.
All real, all urgent.
But it didn’t take long for the real work to emerge—because what’s “urgent” in a founder’s world is almost always entangled with something deeper:
A belief.
A fear.
A mental model that once worked—and now doesn’t.
Things Started To Shift, Because He Started to Shift
Michael has gone through several shifts in our work together so far.
Shift #1: From “Problem Solver” to “System Designer”
Michael’s instinct was to jump in and fix things.
If something was behind—jump in.
If someone underperformed—step back in.
If cash got tight—grab the wheel.
But as we worked together, he saw something quietly profound:
“The system is working perfectly… to keep pulling me back in.”
He wasn’t just reacting to problems.
He was reinforcing them.
The way the company operated—its language, habits, bottlenecks—depended on his involvement.
And that system was working exactly as designed.
When he saw that, he could begin to change it.
Shift #2: From “It Has to Be Right” to “We Learn By Doing”
One day, mid-session, we were talking about rolling out a new sales process.
Michael hesitated.
“I just don’t want to roll this out until we’ve got it right.”
He caught himself—his pattern. Then he paused, smiled, and said:
“Wait… so we can actually learn by implementing? That’s wild.”
It sounds simple. But for a founder who’s used to being the expert, it was a major shift.
We’re trained to think that leadership means having the answer.
But what Michael saw was that progress doesn’t come from perfect planning.
It comes from thoughtful implementation—with feedback, iteration, and team buy-in.
So we built the habit:
Build → Implement → Learn → Refine.
That rhythm became his leadership operating system. And he continues to refine it today.
Shift #3: From “I’m the One They Follow” to “We’re Building This Together”
As we talked over our first four months, Michael often said:
“I’m good at sales. I can close the big deals. But I can’t seem to teach it.”
He carried the weight of being the charismatic founder.
The closer.
The one who couldn’t be replaced.
But in that model, his team was always a step behind.
They weren’t co-creators—they were followers.
As he shifted, we explored a new frame:
What if your team doesn’t need another version of you? What if they need a system they can shape with you?
That meant giving them ownership—not just instructions. Letting them try, miss, adapt.
And trusting that leadership is less about being copied—and more about creating capacity.
Shift #4: From Reactive Urgency to Constructive Clarity
Michael had what I call “cash fear.”
It’s not uncommon for founder-CEOs. When cash dips, the old wiring kicks in:
This is mine to fix. Get involved. Hustle harder. Do more.
But that wiring—once a superpower—isn’t built for scale.
So we looked underneath it. Where did the fear come from? How could he trust the system and still lead with intention?
We didn’t eliminate urgency. But we gave it structure.
Michael began naming what was real, and what was reactive. And acting accordingly.
That changed everything.
The Language Shift: From Describing to Creating
One of the most powerful shifts in our work was how Michael began to hear his own language differently.
“I’m trying to get over the hump.”
“I’ve hit a ceiling.”
“We’re in chaos.”
These sound like observations.
But they’re actually creations.
The metaphors we use don’t just describe reality—they shape it.
As Michael started to notice the metaphors he leaned on, he began to choose new ones:
- From “ceiling” → to “threshold”
- From “chaos” → to “friction with purpose”
- From “problem” → to “signal”
That shift in language reflected something deeper:
He wasn’t just reacting to what was happening.
He was taking authorship of it. And choosing to create it differently.
Coaching Isn’t About Tactics. It’s About Transformation.
In four months, Michael didn’t just put better systems in place.
He saw himself differently.
He led differently.
And most importantly—he started designing a company that didn’t need him to hold it together.
That’s the real work.
Not fixing more things.
But letting go of the identity that says you must.
Because as a leader, the most important systems you’ll ever design are the ones inside yourself.
It Started With Two Days
Are you ready to begin this journey for yourself?
Michael and I started with two days together. Two days that created the foundation for profound transformation in his leadership.
For a select group of leaders, I am creating an event in Denver on October 20-21 to do the same.
Would you like to be considered? DM me and I can tell you more.