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.

It’s a familiar scene in many growing companies:

The leadership team retreats for a couple of days, digs deep, crafts a compelling vision, maybe even a new set of values—and then rolls it out with great fanfare in a company-wide meeting.

There’s a well-designed PowerPoint. Possibly a video. Maybe even branded mugs.

But here’s the question:

How much of it truly sticks?

Not just as slogans on the wall, but as the driver of the company?

Culture Isn’t What You Say. It’s What People Feel.

Culture isn’t installed. It’s not a software update.

It’s an ongoing co-creation of meaning—shaped every day by how people show up, how they make decisions, and what they believe they’re building together.

And that’s the key word: together.

The most enduring cultures aren’t handed down from the top. They’re built from the inside out.

From Rollout to Invitation

A founder I coach had this insight recently. He and his leadership team were circling around a unifying “why”—something beyond revenue targets, something they could all rally behind. And they were excited about sharing it with the team.

But instead of presenting it fully formed, we explored a different path:

What if the team helped shape it?

What if, at the next quarterly meeting, they posed a question instead of presenting a statement?

• “Why are we here?”
• “What kind of experience do we want to create for our customers?”
• “What do we want to feel when we go home at the end of the day?”

These aren’t fluffy prompts. They’re questions that create culture-shaping conversations. And they reveal what already matters to people—what’s already in the DNA of the company that’s waiting to be brought out in to the open.

You Don’t Need a Big Offsite—You Can Just Start

The right culture isn’t created. It emerges.

It’s coaxed from what already is happening when people are at their best.

Here’s what defining a culture can look like in practice:

• A lunch meeting where field staff and office staff share stories of when the company was at its best.
• A whiteboard in the break room with the question: “What’s one thing we’re proud of this quarter?”
• A 15-minute all-hands session where each team shares what they stand for—not what they do, but why they care.

These are simple moves. But they create buy-in because people see themselves in the answers. And they want to be more like the stories they are hearing. They want to be one of the people in the stories.

And when your team helps build the “why,” they don’t need to be reminded of it. They live it—because they made it.

Culture Is a Feeling, Not a File

The best company cultures aren’t designed. They’re discovered.

They live in hallway conversations, the tone of your emails, how you handle pressure, how you celebrate wins—and how you treat each other when you’re not winning.

So if you’re a leader thinking about how to shape culture as you grow:

Try less rollout. More invitation.

The PowerPoint can wait.

Start with a question. And let your people surprise you.

What I am about to share with you might be the most powerful tool I have found in leadership.

Like many of the best coaching tools that I know, I first learned of this one from Steve Chandler.

A large part of the leaders role is to get people to follow, without having to micromanage.

Delegation is an important part of this. But most people who delegate set themselves up for failure.

How?

One Leader’s Attempt to Delegate

One of my clients took particular pride in is willingness to delegate. To hire someone and let them run.

But he wasn’t getting the results that he wanted. And he came to me asking why.

He told me about his most recent hire and all the things that the person was not doing. How he was frustrated, but he didn’t want to tell the person how to do his job.

I asked him if he was familiar with the distinction between expectations and agreements.

Expectations and Agreements, Compared

In almost any area of our lives, when we have a frustration with someone, it is often because they have violated one of our expectations.

The issue is that most of the time, it is an expectation we have never communicated.

Remember that we are all living in separate, internal, worlds?

How would someone else know what we are thinking, unless we have told them?

Just seeing this is a major “aha” for most people.

But there’s more.

Know Your Own Expectations First

My client was hiring people expecting that they would know what to do in their role without much guidance from him. And they did, but they were doing different things than my client expected.

My client didn’t know that he had these expectations—they were not explicit for him—until the new person started doing his or her job differently.

So the first step for my client was observing and documenting these expectations.

Problem solved, right?

Not so fast.

Explicit Expectations are Still Expectations

Even if you get really clear on what you expect from someone, and you document it, you don’t actually have an agreement.

Agreements are based on conversation. Agreements result in buy-in from both parties.

Without buy-in, greater detail on expectations really doesn’t help.

What Are Agreements?

Agreements look something like this—

CEO: “Our investors expect sales to grow 50 percent this year, and I am counting on you and your team to deliver that.”

CRO: “I’d like to talk about that. We don’t have the bandwidth to build the pipeline and have all the meetings that would be necessary to close that kind of business.”

CEO: “Hmm. Tell me more. What would you need from me to be able to commit to that kind of increase?”

CRO: “I have some ideas. One would be another senior sales resource. Another would be…”

CEO: So if I were to give you those resources, you would be willing to commit to a 50 percent increase?”

CRO: “Absolutely.”

Now this is a much longer conversation, but you get the idea.

And sometimes the leader will require her team to stretch, without all the requested resources.

But the key thing is that everyone feels heard. Everyone feels included. And everyone is, to a much greater degree, committed to delivering a result.

This does not happen when the leader simply declares.

When possible, agreements are set in writing, with specific timing and deliverables, and both parties are involved in creating the document.

This is what means to “give ownership.” You AGREE both to the terms and the deliverables. And if you do it right, the person you have given the ownership to is as excited to take it on as you are.

Want to Know More?

Getting clear agreements is one of the things that will make the most dramatic different in your results as a leader.

If you’d like to dive deeper, I will be spending two days with a group of leaders in Denver on October 20-21.

The event is filling up fast. DM me if you are interested in hearing more.

I talked last week about the distinction between behaving like a victim and having like an owner.

I think it was Steve Chandler who showed me this distinction, and it changed a lot for me.

I saw how often my instinct was to blame others, to not take responsibility.

But when I saw that I could take ownership, I noticed some resistance to it after awhile.

Why?

While I understood that being an Owner is much more powerful than being a Victim, I kept thinking that there might be something more.

Something beyond my own personal interests.

I kept wondering about what it would be like to have life happening “Through Me,” to use Michael Beckwith’s framework.

The Nobility of a Just Cause

If you are familiar with Simon Sinek‘s work, you know “Start With Why.”

You know that purpose is a more powerful driver than what you actually do.

And in his later book, “The Infinite Game,” Sinek expands on this idea with what he calls a Just Cause. Something long term, beyond ourselves, that we would be willing to give our entire lives to pursuing.

When I worked for Fidelity Investments, I was in the part of the business that was about tax incentives for employee savings, both through 401(k) plans and health savings accounts.

Our focus was on getting as many working class people to save for their retirements as possible. True, that benefited our business, but that wasn’t what was important to me. It was that in some way, what I did every day made it possible for millions of people to save for and have retirements for themselves and resources to provide for their families.

And I had done the same thing with health care benefits, helping employers provide affordable benefits for millions of employees.

The thing was, no one at any of my employers told me this “why.” It was something that emerged in me.

I was a Steward.

Beyond Owner and Victim

Last week I talked about owner and victim, and the power of taking control of our lives, even as we recognize that we are not ever fully in control of anything.

But that shift is just one of the possible shifts.

As Michael Beckwith wrote, we each operate as if life is happening To Me, By Me, Through Me, or As Me.

Steve Chandler taught me about Victim, and Owner, which I equate to the “To Me” and “By Me” perspectives that Beckwith talks about.

I’ve never seen anyone equate a noun to the “Through Me” perspective, but I’m going to propose Steward.

The Power of Being a Steward

A Steward lives for and from a bigger purpose. A Just Cause, in Simon Sinek’s words.

It can be something that the person creates, or that the person chooses. But the most important thing is that it is beyond an individual. It’s something bigger. And often, it is something that you could work your entire life to achieve.

Martin Luther King was as Steward of a cause much greater than himself. He gave his life for that cause.

Your Just Cause may not feel quite as big, but I assure you it’s just as important.

When you are a Steward, in service of whatever your Just Cause is, you are much more likely to feel fulfillment, purpose, meaning.

And, in my experience, you are much more likely to feel a high level of satisfaction from what you do in the world, even when it is hard.

Part of my Just Cause is helping others identify theirs. Because the world is better off when we are all part of something bigger than ourselves.

What Just Cause have you created, or declared?

And how many people are you leading toward creating it?