Behind the Scenes: Where "What you lose when you lead" fits my thinking
Over the past few years, I’ve been circling a set of questions about what it really means to manage and lead people, not from a business school perspective, not through the usual lists of best practices, but from the ground level. From the quiet, often messy, always human experience of the people doing the work.
My recent piece, What you lose when you lead, came out of that ongoing reflection. It looks at the identity crisis that so often accompanies the move from individual contributor to manager. Not just a change in duties, but something deeper: a disruption in how we understand ourselves. What it means to contribute.
As I was writing it, I kept hearing echoes from other things I’ve been working on. This wasn’t a new insight so much as a convergence. Threads I’ve been pulling at for a while now were coming together. So I wanted to step back and show how this piece fits into the larger pattern of my thinking.
A foundation: Management as craft
When I first started thinking of management as a craft, not just a role, something clicked. I wrote then about how every craft has its own materials—wood, metal, clay—and how in management, the material is human nature.
That shift in framing helped me understand why technical excellence alone doesn’t prepare someone to manage. But this new piece took me somewhere more personal: what happens when someone who's mastered one craft (engineering, finance, design) is suddenly asked to switch materials and identities. That disorientation isn’t just about skill. It’s about self.
I've seen it again and again. Someone who used to feel confident and clear becomes unsure of their value almost overnight. The rules are different, and so is the work. But the harder part is that their old sense of worth no longer fits.
From prose to poetry
This connects to an idea I keep returning to: that managing is prose, but leading is poetry.
New managers often try to lead like they used to work: with structure, logic, and precision. But what this new role asks for is something less linear. It’s relational, interpretive, often ambiguous. They’re speaking prose when the situation requires poetry.
In writing What you lose when you lead, I found myself thinking about that awkward middle place—where you’ve lost the fluency of your old language but haven’t yet learned the rhythm of the new one. It really does feel like phantom limb syndrome. You keep reaching for a way of contributing that no longer exists.
When good intentions backfire
One of the patterns I’ve seen—managers reverting to individual contributor work—isn’t just tactical. It’s existential. They’re trying to feel useful again. So they jump in. They fix things. They work late.
And I get it. I’ve done it. It’s satisfying, familiar, and immediately rewarding. But as I’ve written elsewhere, that instinct often leads to the exemplarity trap: trying to model the behavior you want to see, hoping others will copy it.
The problem is that management isn't about creating copies. It's about helping people become originals.
Reconstructing satisfaction
This part feels especially close to the bone. A lot of what I do in my coaching work is helping managers rediscover what satisfaction looks like now.
I’ve spent time thinking and writing about motivation (how it works, what drives us) and what I’ve learned is that new managers often lose their most familiar source of satisfaction (technical mastery) before they’ve found a new one. There’s a void.
Some mourn that loss quietly for years.
But there’s another kind of satisfaction that can emerge. Less immediate, but deeper. The quiet power of enabling others to rise. The long arc of shaping not just outputs, but people. You don’t get applause for it. But if you can shift your motives, it starts to feel meaningful in a very different way.
A practice of honesty
That shift doesn’t happen automatically. It takes reflection and often, community. That’s where the idea of the Manager’s README came from.
The README is a tool, yes. But more than that, it’s a way of practicing radical honesty with yourself and your team. Writing one forces you to confront the distance between what you intend and how you act. And I’ve found that kind of honesty to be a turning point for a lot of people going through this transition.
The change is real. Pretending it isn’t doesn’t help anyone.
Working with rather than against
If there’s a deeper thread running through all of this, it’s probably this: learning to work with rather than against.
That shows up in lots of places in my writing:
In embracing chaos instead of trying to eliminate it
In letting time do its work rather than trying to squeeze more out of every hour
In recognizing human motives instead of trying to manipulate them
And it’s right there in the identity crisis that new managers face. Individual contributors succeed by controlling variables. Managers succeed by surrendering control and learning to work with what’s alive in other people.
That’s not a minor change. It’s a whole new way of relating to the world.
What it might mean for how we develop leaders
This brings me to the question that’s been tugging at me most:
So where does all this lead?
To me, What you lose when you lead marks something of a pivot. It brings together many threads I’ve been following—craft, poetry, exemplarity, motivation, honest self-reflection—but applies them to one of the most common, misunderstood, and under-supported transitions in working life.
But it also leaves me with questions I don’t yet have answers to.
How do we support people in this shift, beyond giving them tools and tips? What kind of development experiences could help them not just cope with the loss, but grow into the possibilities? How can we allow people to grieve what they’re leaving behind and still see what they’re stepping into?
I’m still working on those questions. And I’m open to being surprised.
This is the first of a series I’m calling “Behind the scenes.” A place for me to connect the dots between pieces, share what’s unfolding in my thinking, and invite you into the process. If you’re going through this transition yourself, or helping others through it, I’d love to hear what’s helped, what’s been hard, or what you’re still figuring out.
This isn’t a finished framework. It’s a conversation I hope we can keep having.