The Desperate How vs. The Curious How: A Leadership Distinction That Changes Everything
"How are we going to fix what's not working?"
The question came mid-way through a leadership session I was facilitating with SME’s across a global function. It’s a seemingly simple question, yet how you approach it can change everything.
Around the table sat seven senior leaders—each a key stakeholder in a set of 24/7 operations with 1000’s of employees. This wasn’t our first meeting.
In fact, I had met one-on-one with each of them beforehand, asking a different set of simple questions—this is how we establish the baseline.
What’s happening right now (in your department, your function, your leadership)?
What’s working? AND, what’s not working?
It’s what I often refer to as Island A—our starting point. And the reason I like to call it an island is that it's an actual territory we’re standing in. It's the place we’re coming from. “A” stands for accurate—our “as is reality”, the territory we live in. Not what we hope or assume, but what’s actually happening.
When we gathered together in the room, we spent the first part of our session deepening that collective understanding—getting grounded in Island A.
We then began articulating Island B—you can’t go somewhere unless you know where you begin. “B” is for a better state, and for who you want to be in this better state.
And then came the seemingly simple question,
“How are we going to fix what’s broken to get to Island B?”
Again, this is a reasonable question. Yet the way the question came out, I would have put money on the fact that it would never get answered. You see, the question didn't come from a curious, inquisitive place, rather its origins were desperate, already predetermined and full of despair — as if her hands were being thrown to the heavens, “hooooow?!”, like a howl.
The Desperate How vs. The Curious How
There are two kinds of “how” I often see in leadership conversations.
The “desperate how”—arms in the air, energy spiraling, looking to the sky.
This “how” holds a hidden desire for someone else to come in and provide the answers—a kind of unintentional victimhood.
The “curious how” has a sense of wonder to it—like that of solving a puzzle or playing a game.
“How will we begin to solve what’s not working?”
“What is going on here anyway?”
“What do we need to look at together?”
This kind of “how” takes ownership. It recognizes that the answer doesn’t exist out there—it’s something we create and discover. It’s grounded in responsibility and possibility.
It’s also generative. Not because it guarantees an immediate solution, but because it opens the space for leadership to emerge.
A Leadership Shift
So I put the question back in their hands:
“There are 7 senior leaders at this table. How will you fix what’s not working in service to what’s next for you?”
This, to me, is leadership. It’s the subtle but powerful move from helplessness to authorship. From wanting someone else to fix it—to stepping up and saying, this is our work to do. Let’s roll our sleeves up and begin.
Dear reader, which “how” do you practice most? And how might this distinction refine your leadership today? Will you share?
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