Don’t Just Coach—Cultivate: The Real Work of Executive Leadership
There’s a word that’s become trendy in leadership circles. Coaching.
Now, I’m someone who offers executive coaching so I’ve got skin in the game. But I’ll tell you right now: coaching isn’t the finish line. It’s the starting soil.
Because real leadership—the kind that transforms teams and builds legacy organizations—isn’t just about giving better feedback or guiding people toward goals. It’s about cultivation.
Coaching is the spark. Cultivation is the garden.
When I sit down with a CEO or senior leader, I’m not just looking to help them become more effective. I’m looking to help them create an ecosystem. One where their people are growing in capacity, clarity, and cohesion—even when no one’s watching.
So if you’re serious about scaling your leadership impact, start thinking like a cultivator. Here’s what that looks like.
1. Cultivation Starts with the Soil
Not long ago, I worked with a founder based just outside Denver. He was frustrated. “My exec team isn’t stepping up,” he told me. “I keep coaching them, encouraging them, even incentivizing them—but they won’t take initiative.”
So I asked him: “What’s the soil like?”
He blinked. “What do you mean?”
I meant the conditions they were working in. The culture. The trust levels. The clarity (or lack thereof). The psychological safety. Because leadership doesn’t happen in a vacuum—it grows in soil.
If your team is playing it safe, shrinking back, or second-guessing you, it’s not a personal flaw. It’s a signal from the system. Maybe your expectations aren’t clear. Maybe there’s a fear of failure. Maybe feedback feels like punishment instead of partnership.
When we started tending to the cultural conditions—realigning roles, clarifying priorities, resetting norms—it was like the lights came on. Within weeks, the same leaders were pitching new ideas, initiating hard conversations, and owning outcomes.
Coaching didn’t fail. But cultivation made it stick.
2. You Don’t Have to Be the Water
This one’s for my fellow overfunctioners.
Many of the leaders I support through executive coaching share a common pattern: they believe they need to be the energy source in every room. The idea person. The motivator. The fixer.
It’s heroic. It’s also unsustainable.
Here’s the shift: stop trying to be the water. Start building the irrigation.
When you cultivate, you’re designing a system where energy, clarity, and initiative flow naturally—not just from you, but across the team. That might look like:
Designing meetings that prompt ownership, not passive updates
Creating rituals that reward vulnerability and learning
Delegating not just tasks, but authority
Publicly recognizing behaviors you want repeated
One Denver-based COO I worked with made this shift beautifully. She went from being her team’s “emotional engine” to being its “pattern noticer.” Instead of injecting energy into every meeting, she started asking sharper questions, setting clearer expectations, and stepping back. The result? Her team became more creative, more accountable—and she stopped burning out.
You don’t need to water every plant. You need to shape an environment where the watering happens naturally.
3. Growth Requires Pruning
Cultivation isn’t just gentle. It’s also firm. And sometimes, it’s surgical.
Growth requires pruning.
Outdated processes
Misaligned roles
Beloved but ineffective habits
Even high-performing individuals who are no longer a fit
This is the part most leaders resist. Because pruning feels like loss. Like giving up. Like conflict.
But here’s what I’ve learned in the trenches of executive coaching: every team has baggage. And what you choose to tolerate becomes your culture.
One CEO I worked with was avoiding a tough conversation with a co-founder who’d outgrown the role. They had history. Loyalty. Friendship. But it was clear that the business had outpaced his capacity.
After months of dancing around it, they finally sat down. It wasn’t easy. But it was honest. And ultimately, they found a new role that better suited the co-founder’s strengths—and opened space for the team to level up.
Pruning isn’t about cutting people down. It’s about making room for what’s next.
4. Culture Is Grown, Not Declared
Let’s talk about culture.
You can have all the right words on the wall—transparency, collaboration, innovation—but if your exec team whispers their real concerns in parking lots and slack threads, you don’t have culture. You have theater.
Real culture is practiced, not printed.
And it starts with the small stuff:
Who gets rewarded?
What gets tolerated?
What happens after someone makes a mistake?
Who speaks up—and who stays silent?
As part of my work in executive coaching, I’ve helped leadership teams design rituals that reinforce the culture they claim to want. One team added a “culture checkpoint” to their weekly huddle. One simple question: “What did someone do this week that reflects who we want to be?”
That question alone began to rewire how the team saw each other. What they noticed. What they valued. And slowly, the culture moved from words to habits.
You don’t build culture in a day. But you shape it with every choice.
Here’s the Shift That Matters Most
Imagine your next leadership offsite.
Instead of talking in circles about “accountability” or “vision,” you’re in a room where people challenge each other with care. Where hard truths are welcomed. Where laughter and disagreement can co-exist.
Where the team feels alive.
That’s what happens when you stop trying to fix your team—and start cultivating your team.
Coaching is powerful. I do it every day. But if you want lasting change, you’ve got to tend to the system. To the soil. To the unseen forces that shape how your leaders lead.
If your team has been coached but still feels stuck, I’d love to help you shift the focus.
Because you don’t need to push harder. You need to grow smarter.
Let’s tend to the soil.
