Last week, while running a two-day leadership intensive with a group of senior leaders, something familiar hit me in a completely new way. I’ve always known it, but this time it landed deeper:
Great leadership requires you to hold your plans both tight and loose.
Most leaders cling to planning like a life raft. We organize, structure, anticipate, forecast, and map things out with impressive detail. And look, these plans matter. They give us direction. They create clarity. They serve as scaffolding.
But the truth is, leadership doesn’t live in the plan.
It lives in the moments you couldn’t plan for.
When I reflected on the experience, I realized how essential it is for leaders to “dance with the moment.” That’s what separates rigid leadership from creative leadership, and creative leadership is where real transformation happens.
Here’s what I mean.
When you’re leading people — not tasks, not projects, but people — you can’t perfectly predict what will unfold. Someone will say something unexpected. An assumption you thought everyone shared will be challenged. A discussion won’t land the way you hoped. A plan that made perfect sense on paper suddenly feels mismatched to the room you’re standing in.
And just when you think something is falling flat, a quiet question from the corner will spark an entirely new insight. Someone will make a side comment that opens the door to a deeper truth. The group’s energy will shift into something you couldn’t have scripted but is precisely what was needed.
So here is what I mean by “the dance”.
The best leaders don’t try to force reality to match the plan.
They adjust the plan to meet the moment.
That requires presence, awareness, humility to let go of control, and the courage to step into uncertainty without losing the thread of where you’re trying to go.
Here’s the subtle shift in assumptions we need to adopt:
The plan is only the starting point.
The moment is the teacher.
Leadership is the dance between the two.
When leaders cling too tightly to their plans, they miss what is actually happening in front of them. They miss opportunities to respond, redirect, or deepen the conversation. They miss the emotional currents in the room. They miss the very insights that could create the breakthrough they hoped the plan would produce.
But when leaders hold the plan lightly, they become available to the moment. They notice what the team needs, sense when energy is rising or dropping, and hear what’s not being said. They follow the thread of curiosity instead of forcing the script.
And that’s when they shine as a leader!
So here’s something to try this week:
Take one meeting or one conversation you’re preparing for, and build your plan like you normally would. Make your notes, define your outcomes, and now your structure.
But when the moment arrives, loosen your grip. Notice what’s unfolding, and let the experience teach you something.
That’s where the real magic happens.
