The Work Most Leaders Never Get To Do — And How I Came To Do It

There's a kind of work organizations need but rarely hold whole

If you scan the senior-leadership roles being hired for right now, there's a pattern that looks like a market mistake. It isn't.

There's a kind of work that organizations need but rarely know how to hold whole.

It's the work of aligning strategy, structure, culture, talent, and operating model so they compose into something instead of pulling against each other. The work of designing how people work together, not just what they work on. The work that decides whether your strategy lands in the day-to-day or stays in a deck. The work that determines whether your organization can actually innovate, collaborate, change, and adapt to whatever comes next. These are the capabilities every leadership team is trying to develop, and very few seem able to install.

Ralph Lauren is recruiting a Director-level Organizational Design Lead. Gartner is hiring a Senior Director Analyst for Organizational Design. Lockheed Martin is looking for an Organizational Design Subject Matter Expert. Harrods is hiring an Organisation Design Manager. IDEO is hiring an Organizational Design Lead. McKinsey, BCG, Bain, Deloitte, and PwC all run Organization or People & Organization practices. Boutique firms like The Ready, August Public, Median, frog, and Fjord exist to do this work for clients who can't do it internally.

A reader could be forgiven for thinking this is a well-defined profession.

It isn't. The same work goes by Organizational Design, Organizational Development, Change Management, Transformation Consulting, Culture Consulting, Strategic Operations, Chief of Staff, People & Culture, Executive Coaching. Inside companies, it's distributed across at least six named senior roles: Chief of Staff, Chief People & Culture Officer, Chief Operating Officer, Chief Strategy Officer, Head of Organizational Design, Head of Talent. Rarely is it owned end-to-end by any of them. The work is holistic by nature. The structures designed to hold it are fragmented by default.

That fragmentation is the problem these organizations are paying firms to solve.

It's a leadership development problem, not a hiring problem

There's a deeper problem inside that fragmentation. When organizations decide they want the integrating work inside their teams, they hire for it the same way they hire for everything else. As a domain expert. As a craft expert. As an individual contributor. They post a role, get applications from people who hold deep expertise in some slice of organizational work, hire the strongest one, and place them somewhere on the org chart.

It doesn't work. The reason it doesn't work is that the problem isn't a domain problem or a craft problem. It's a systems problem and a leadership development problem at once. It's a problem about how the senior team thinks, decides, and grows the capacity to hold what specialists can't hold for them. They hire for subject-matter expertise when they should be building capability. Hiring a domain expert to solve it is like hiring a better mechanic to redesign the car.

The mismatch is structural. It's downstream of how most organizations were built to think about work in the first place. Most organizations are still running, in their bones, on a framework Frederick Winslow Taylor published in 1911 about how to manage a factory.

Even Jack Welch — whose 1981 shareholder-value speech became the modern continuation of Taylor's framework, and who was lauded as the management exemplar of his era — publicly disavowed his own thesis in 2009, calling shareholder-value-as-strategy "the dumbest idea in the world." Most management training today still operates on the playbook he wrote before he changed his mind. The framework persists past its own author's reversal.

David Epstein, in Range, names the consequence at the hiring layer: generalists triumph in specialized worlds, but specialized worlds penalize range as "not a specialist." Integrators get filtered out at the first hiring panel screen.

There's an architectural framing for what's actually at stake. Nassim Taleb made the distinction between systems that are robust and systems that are antifragile. Robust systems survive shocks by absorbing them; antifragile systems get stronger from disorder. Most organizations are built to be robust. Innovation, collaboration, change agility, adaptability — these aren't domains you can specialize someone into. They're properties of the whole system's posture toward change. You can't hire your way to antifragility by adding more domain experts who keep the existing structure intact.

The holistic work that solves fragmentation gets fragmented by the structures it's trying to fix.

That recursion is the structural diagnosis. The work won't be solved by hiring better specialists. It will be solved when senior leadership teams develop the capacity to hold it themselves. That's a leadership development problem, not a hiring problem.

I came to this work through a microscope, a knitting mill, and a marriage that crossed class boundaries

Some people develop the capacity to hold this work whole. Not many. Not most. Almost none of them through the canonical professional training tracks for organizational design or change management or leadership coaching, because those tracks all teach one slice of the work at a time. The integrating capacity tends to develop somewhere upstream of any single discipline, in a person whose career composition was atypical enough that nothing along the way insisted they specialize.

I'm one of them. Not because there's anything unusual about me. Because the composition of my background and the influences I absorbed are specific enough to be illuminating. I've spent fifteen years doing this work for organizations across multiple stages and shapes.

This article is about where the capacity to do the work came from. The honest answer requires going back further than my career — to a microbiologist, an electron microscopist, a draftsperson at a Detroit auto studio, a knitting mill in a Michigan town, and a marriage that crossed classes. Each one taught me something I now use every day.

My father, Dr. Douglas E. Caldwell, was a microbiologist at the University of Saskatchewan. By the time I was eight, his research career was well into its arc. My mother was an electron and confocal microscopist — the resolving power that made his theories visible. They worked together. They talked about the work at the dinner table.

I remember sitting in the living room or at dinner, between the ages of eight and ten, trying to follow what my dad was saying. He would talk about balanced proliferation and nested propagules. About biology's calculative units. About what evolution looks like when the unit isn't the organism but the community. The language was beyond me; the felt-shape of what he was saying wasn't, quite. I knew, in the way a kid knows things without having words for them, that there was something different about how he thought. He wasn't talking about animals. He was talking about how reality is organized.

The published version of that conversation, decades later, would call it the calculative nature of microbial biofilms. Calculative units consisting of two proliferating structures, one nested within the other, each undergoing changes in structural geometry that affect the proliferation rate of the other. Communities, he was arguing, are units of evolution. The individual is downstream of the community, not upstream. Bill Costerton, his close collaborator and the field's founding figure, agreed.

That was one half of my father's side. The other was my paternal grandfather, a draftsperson who in the early 1960s sat at a drafting table at Chrysler in Highland Park, Michigan, and helped translate the design of the only jet-turbine-powered passenger car America would ever produce in series. He sat at the boundary of automotive design and aerospace propulsion, and made both sides cohere on paper.

He kept a drafting table in his basement. I would visit as a kid and sit at it, drawing and designing things on the same kind of surface he had used for the work in Highland Park. The lineage of design was literal: a draftsman's table, two generations of people who used it to think with their hands.

At the dinner table, listening. At the drafting table, drawing.

My mother's side was quieter. The history wasn't talked about the way my father's research was. It was just there, unmentioned.

The two sides of my family had come from very different places. The Caldwells had started in poverty four generations back, working their way up through skilled trades and into academia by my father's generation. The Chapmans, on my mother's side, had built and held industrial wealth for generations. My great-grandfather William Clark Chapman and his brother organized Western Knitting Mills in Detroit in 1891 and moved the operation to Rochester, Michigan a few years later. The factory grew to employ five hundred workers and became the second-largest knitting mill in the country; by 1917 it was running government contracts for millions of pairs of army gloves. The family chose to stay rooted in Rochester rather than chase the auto fortunes of Detroit. The Chapman House, built in 1916, stayed in the family until 1973. My mother, Sarah, grew up there. My parents got married there.

The marriage happened in a particular American moment. The post-war middle class had been built out across the country, and the educational system had opened up alongside it. My parents met during their undergrad. University was one of the first places where traditionally separate parts of American society could meet each other directly.

The marriage between my parents was its own integration — two backgrounds that hadn't been built to meet, meeting anyway. My paternal grandfather, who had lived the working-class side of the family more directly than my father did, told my mother he didn't think the marriage would work. He said it the first time he saw the Chapman House.

He was wrong. They've been married for over fifty-two years.

But it worked at a cost my mother carried.

She had been on track to become a doctor. She took classes at Harvard back when Harvard was still segregated between men and women, navigating institutions that had not yet been built to admit her. When she married my father, she stepped off the doctor's track. Academic postings were few and far between, and the convention of the era was that the woman followed the man's career. My father chose between Tennessee and Saskatchewan; he chose Saskatchewan. We moved to Canada when I was four. My mother became an electron microscopist, the resolving power that made my father's theories visible. The partnership was still a partnership. It just wasn't the partnership she had been preparing for.

She wasn't the first woman in my mother's line to navigate institutions not built for her. My great-grandmother died in the 1918 flu pandemic. My grandmother, Wilma, worked as an interior designer and contributed to the design of Grumman aircraft during World War II. Three generations on my mother's side. None of them got to be quite who they had set out to be. All of them built something anyway.

I learned most of this slowly, in pieces, over decades. The class history surfaced in conversations over the years, many of them during a period when I was helping my mother provide care for my father.

I didn't grow up knowing any of this. The shape of it was already in me by then.

The way through, for me, was design

My family was shaped by a particular power structure. My father was at the top of it. His career choices determined where we lived, when we moved, and what was discussed as serious work at the dinner table. My mother had stepped off the doctor's track to follow him. The household register was science.

My rebellion took a specific form. I dropped biology and took art class. It looked like a small choice at the time. It was the first time I chose for myself, and it would matter more than I could imagine. The science register was the family's. The art register was mine.

What I didn't see at the time was that the rebellion wasn't a departure from the lineage. It was the lineage finding a different way to express itself. The integrating capacity I had absorbed wasn't going to disappear because I stopped studying biology. It was going to find a different way through. The way through, for me, was design.

By design I don't mean aesthetics. I mean a methodology for problem-solving and solution-finding that puts people at the heart of value creation, at the same level as the scientific method and the strategy model. Paired with systems thinking, design applies that judgment to systems themselves, not just the products inside them.

My first professional work as a designer was at a small studio building interactive educational software for the Alberta learning community. The software taught spectral reading and the Doppler effect — optical concepts you could see and touch on a screen. The vocabulary I still use for thinking about how teams and organizations work traces directly to that period. Frequency. Resolving power. Spectral analysis. I was building tools that made the invisible visible at scale, in the same instrument-design tradition my mother had used at the microscope and my father had relied on at his desk.

The thread through everything that followed was small teams. I ran a small design and software company of my own. Later I joined a digital studio under twenty people, headed by a world-renowned technical founder, to build a design team, culture, and practice inside what had been a developer-only environment. In every one of those settings the work meant wearing all the hats, crossing all the boundaries, doing all the things, whether I was the business owner, the leader of a department, or a member of a leadership team.

The work itself was services and bespoke software, often involving emerging technologies as they came to market. Across those years I worked across global brands, platform teams, enterprise-scale clients, and leadership teams at companies navigating the kinds of structural and cultural challenges most organizations haven't built the capacity for.

Throughout, my parents kept giving me books. My father's gift was Neal Stephenson, science fiction whose science was really philosophy of how systems and cultures work. My mother's was Asimov, where the diagnostic move was always to find the hidden belief that explained the erratic behavior of thinking machines. Before I had any vocabulary for organizational diagnostics, I had Asimov teaching me to look for root causes. The science register I had rebelled against was still trying to give me tools, in the form it knew.

What followed wasn't just reading. It was self-directed education at depth. Richard Rumelt's Good Strategy Bad Strategy took me six months to absorb. Not six months of reading — six months of applying the Kernel of Strategy in live work, integrating what worked, and trying it again until the framework was integrated, not just understood. IDEO's Leading for Creativity course was the catalyst that connected everything into a single applicable system. Before it, the references were individual frameworks. After, they were a connected operating system for the work I had been doing for years without language for it.

This mirrors agile product development. And it points at a belief I hold about leadership: your practice is something you can design and improve, the same way a business iterates on what customers actually need.

The work is what I'm offering

What I described at the start of this article is happening inside most organizations right now. Including, very likely, yours.

The integrating work that organizations need fragments across specialist roles. Strategies don't reach the day-to-day. Team dynamics break under the pressure they were built to handle. Operating systems get inherited rather than designed. Most leaders feel the friction but can't quite name what's structural about it.

What gets lost when factory-era management dominates isn't abstract. It's joy in the work. Room to lean into human strengths — creativity, intuition, social attunement, adaptive sense-making. Strengths the factory model labels as inefficiencies. The ability to feel purpose and stay connected to what we're building, and to the people we're building it with.

What we could gain by moving beyond it is everything that's been waiting for us to design new systems instead of inheriting the last significant innovation from 1911. Organizations that compound joy rather than burning it. Teams that adapt because they were built to. Leaders who can be human at work instead of leaving most of who they are at the door.

I've spoken to hundreds of people in this work — leaders, employees, individual contributors. They've shown me what the post-factory era of leadership and management actually provides. It doesn't replace what we've gained. It enriches it. It extends it. It fills gaps that couldn't be filled under the old way of thinking. This isn't either/or. It's also/and.

The work I'm offering is partly about getting these things back.

Caldwell Leadership is where that work gets done. Leadership development at the senior team level. Team dynamics that hold under pressure. Organizational and systems design that produces effectiveness rather than just efficiency. The integrating capacity I've described in this article is what I now bring to other organizations.

This is the work my family taught me how to do — at a microscope, at a drafting table, at a kitchen table where the women in my line built things inside institutions that hadn't been built for them. They showed me, in pieces, over decades. The window in which it matters is open and not infinite. The organizations that develop this capacity will define what the post-factory era looks like; the ones that don't will spend the next decade running harder against a structure designed to slow them down.

If any of this resonates with what you're seeing in your work, reach out and start a conversation.

The lineage in this article isn't the credential. The work is. And the work is what I'm offering.