My daughter is a Girl Scout.
And if you've watched a child move through that organization — the badges, the friendships, the cookie tables outside grocery stores, the slow building of confidence and civic identity — you know there is something quietly extraordinary about an institution that has endured for over a century and still manages to be genuinely relevant to the lives of young girls today.
That doesn't happen by accident. It doesn't happen because of a good founding idea, or even a good program model. It happens because of leadership. Specifically, the kind of leadership that Frances Hesselbein brought to the Girl Scouts when she became CEO in 1976, at what was arguably the most perilous moment in the organization's then 64-year history.
Hesselbein believed that leadership is fundamentally a question of how to be, not how to do it. Not a basket of skills or strategies you pull out when needed. Something deeper, rooted in character, in values, in genuine presence to the moment in front of you.
I've been sitting with that idea for a long time. The more I do, the more I think it points directly at the skill I find hardest to develop in myself, and most consequential when I get it right.
Knowing when to hold. And when to move.
I'll be honest: I haven't mastered this. I'm not sure anyone fully does.
But I've become convinced it's the right question to keep asking, and that the asking itself is a form of leadership practice.
Here's what I mean.
I'm wired to act. Personality assessments over the years have confirmed what I already suspected: I have a strong bias toward progress over perfection. I get restless when work becomes routine. I'm energized by complexity and novelty, and I tend to find inaction more uncomfortable than the risk of moving in the wrong direction.
In startup environments, that wiring is an asset. When you're building from scratch, the ability to make a decision with incomplete information and keep moving is essential. Momentum is the thing you're protecting.
But that same wiring can become a liability in other contexts. In a mature organization navigating a sensitive transition, the instinct to act can close off options that needed more time to develop. In a complex multi-stakeholder negotiation, moving too quickly can signal impatience that erodes trust. In a team going through a hard moment, the impulse to solve the problem can get in the way of the more important work of simply being present for it.
I've made all of those mistakes. Some of them more than once.
What Hesselbein modeled across 13 years leading the Girl Scouts — and decades of leadership work beyond it — was something different from either always holding or always moving. I'd call it conscious presence: the discipline of reading what a specific moment actually requires, rather than defaulting to a pattern.
She was known for her circular management philosophy, the idea that the leader sits at the center of concentric rings rather than at the top of a hierarchy, with information and decision-making flowing in all directions. That structure is only possible if the leader is genuinely paying attention to what's happening around them. Not executing a predetermined playbook, but responding to the actual situation in front of them.
The Girl Scouts under her leadership didn't just survive. It was transformed, and built into something durable enough to still be shaping young women's lives nearly 50 years later. My daughter is one of them.
That's not a small thing. That's what it looks like when a leader gets the question right consistently enough, over a long enough period of time, that the answer becomes embedded in the institution itself.
The question I'm trying to ask more consistently in my own work is a simple one:
Not: what am I comfortable with? Not: what has worked before? Not: what would move things forward fastest?
What does this moment, with this team, in this organization, actually require right now?
Sometimes the answer is decisive action. Sometimes it's patience. Sometimes it's a hard conversation that's been deferred too long. Sometimes it's the discipline to stop solving and start listening.
The leaders I've watched struggle most are the ones who never ask the question. Who always move because they're wired to, or always hold because change feels risky, and who have mistaken their default for their judgment.
Real judgment, I've come to believe, is what happens when you interrupt the default long enough to actually look at what's in front of you.
Hesselbein also believed in questioning everything: every assumption, every policy, every practice. Not out of skepticism, but out of genuine curiosity about whether what you're doing still fits the reality you're in.
That practice — of regularly asking whether the approach still fits the moment — is the foundation of knowing when to hold and when to move. You can't make that call well if you're not paying close attention. And you can't pay close attention if you're on autopilot.
I don't have a formula for this. I'm not sure one exists. What I have is a growing conviction that the willingness to keep asking the question, even when your instincts are telling you they already know the answer, is itself a form of operational excellence.
Maybe the most important one.