Why borrowing the right strategies still leaves most organizations stuck
Randal Evans | randalevans.com/writing
A few weeks ago I came across a post that stopped me mid-scroll. A senior leader at a regional health system was describing the rollout of a new care coordination platform. Years in development, significant investment, genuine clinical promise. The technology worked. The outcomes data were encouraging. And then, in the final line, almost as an aside: The hardest part, as always, is the people side. You just can’t scale culture.
The post had dozens of reactions. The comments were full of knowing agreement. So true. It’s always the people. I kept returning to it over the following days, not because the observation was wrong exactly, but because of what it did. It closed a door. It took a structural question, why do organizations with real potential and genuine commitment keep hitting the same ceiling?, and converted it into a verdict about human nature. Culture can’t scale. Leadership can’t be replicated. You find the right person, you build around them, and when they leave, you hope for the best.
I have been sitting across from that verdict for most of my professional life, in boardrooms and planning retreats and strategic planning conversations, and I have watched it do its quiet damage. But I have also seen the other thing: organizations that seem to operate by a different set of assumptions entirely, where the ceiling keeps moving, where what got built doesn’t depend entirely on who built it.
The difference, when I look closely, is almost never what I expected to find. It is not the leader’s personality, or the quality of the strategy document, or the sophistication of the tools. It is something prior to and more fundamental than all of those. It is what the organization, and the people leading it, assumed to be true before any of the strategies were chosen.
The CEO Who Didn’t Know He Had a Leadership Philosophy
Consider a CEO who came to his role through a door most executive search committees wouldn’t think to open. His training was in applied behavior analysis, a discipline built on a deceptively simple premise: define precisely what you are trying to change, measure it honestly, test your intervention, and adjust based on what the data actually show rather than what you hoped they would. He spent years doing this with children and families navigating autism spectrum disorder, working at the intersection of behavioral science and the kind of slow, incremental progress that only becomes visible when you’re measuring carefully.
When he moved into organizational leadership, he did not arrive with a management philosophy. He arrived with a set of habits. Measure what matters. Start before you have everything figured out. Let the evidence tell you when you’re wrong. Treat every initiative as an experiment whose results you are genuinely curious about rather than an investment whose outcome you need to defend.
What he built over the following decade is worth examining in some detail, because the surface features are easy to mistake for the cause. His organization developed a planned giving program from nothing. No infrastructure, no dedicated staff, no established donor pipeline. In less than a decade, the organization had a functioning, self-reinforcing system with nearly a hundred documented legacy commitments, a professional advisory council of estate attorneys and financial planners who actively refer donors, and an engaged governing board that took seriously its duty to ensure for the organization’s financial wellbeing. Every board meeting included reporting on development metrics and discussions around the board’s involvement with the fund development strategy. Realized gifts approached two million dollars. Deferred commitments exceeded five million. A charitable lead trust generated reliable annual revenue. All of this from an organization whose CEO, by his own account, knew almost nothing about fundraising when he started.
But the specific outcomes, and the specific actions that led to them, are not the point. What is worth attention is how each of those things came to exist. The CEO joined the newly-formed legacy giving circle personally, and made sure his development director did the same, before asking anyone else to consider it. When he hired that development director—young, without extensive sector experience, but sharp and genuinely committed—he made the organization’s investment in planned giving a condition of the role, not a future possibility. He embedded specific annual goals into the strategic plan rather than aspirational language. When the governing board needed to hear the case for planned giving, he brought in an outside voice. Not because the CEO lacked credibility, but because he understood that some messages land differently depending on who is carrying them. He committed the organization to completing a structured endowment-building program, and asked which graduates of the program had seen the most success and what made the difference. He then acted on the answer: the organizations that dedicated a specific person to planned giving consistently outperformed those that treated it as a side responsibility. He hired someone for this position within the same planning cycle.
In the moment, none of this reads like visionary leadership. It reads like someone who asks good questions, acts on the answers, and does not require certainty before beginning. What he did not do is equally telling. He did not commission a consultant to design the optimal planned giving program architecture before launching. He did not wait for the governing board to reach consensus about strategic priorities. He did not spend the first year building the case. He got started, measured what happened, and built from there.
It is only in retrospect that this looks like a philosophy. At the time, it was just how he worked.
The CEO Who Was the Strategy
Now consider a different organization, and a different kind of leader. He is, by any reasonable measure, accomplished. He came up through the operational and financial side of the organization. Nearly two decades managing budgets, contracts, and revenue systems before stepping into the top role after a series of leadership transitions that the board never quite managed to resolve. When he took over, the organization was financially precarious: inconsistent revenue, deferred maintenance, contracts going uncollected. Within several years, he had stabilized spending, diversified revenue sources, and built the financial systems that turned a fragile organization into one with a credible balance sheet. The board, which had weathered years of uncertainty, was grateful. Over time, that gratitude became deference.
The board itself was large and structurally complex, its composition shaped by overlapping requirements from multiple funding sources, each with its own governance mandates. On paper, this should have produced a board with diverse perspectives and strong accountability to the communities the organization served. In practice, it produced something closer to the opposite. The CEO managed the board not by engaging its full composition but by cultivating a small inner circle—a loyal board chair, two senior staff members, and a handful of longtime outside advisors—who effectively made the decisions that the full board would later ratify. New board members were recruited not through a matrix of skills and community connections that might strengthen governance, but through personal networks: people the CEO knew, people who had relationships with the inner circle, people whose temperament suggested they would be cooperative rather than challenging. The board met regularly, as required by funder mandates. It did not, in practice, govern. It confirmed.
This is not a story about bad faith. The CEO was genuinely committed to the mission. His financial turnaround was real and consequential. The people around him were, for the most part, competent and well-intentioned. But the architecture he had built, reflecting the same instinct for control and systematization that had rescued the organization’s finances, had produced an institution that could not function without him at the center. When a funder asked a question, the honest answer was that he was the answer. When a staff concern escalated, it landed on his desk regardless of the organizational chart. His calendar was a continuous rotation of individual conversations, with board members, staff, funders, community partners, most of them requiring something from him specifically.
When the organization decided to expand, opening additional facilities in surrounding communities (leveraging its now-strong financial position to secure outside funding), the surface metrics looked encouraging. New locations opened. Revenue grew. But the expansion amplified something the CEO had not accounted for: the conditions that had made the original site work were not embedded in systems or processes. They were embedded in him. Staff at new locations struggled with morale and engagement. Community relationships that had taken years to build at the original site did not transfer. Online reviews turned negative. Internal disengagement became chronic. The CEO’s diagnosis was consistent: people were the “problem.” Managers who couldn’t execute. Staff who didn’t understand the vision. He needed better people.
To find them, he turned to psychometric testing. Not to a single instrument, but to several, accumulated over years in the same spirit of genuine problem-solving that had driven his financial work. The assessments were meant to identify top performers, understand team dynamics, surface the traits that made certain people effective. The goal, stated plainly, was to find the profile of the people who worked well and then recruit more of them. Clone the best. Replace the rest.The result was an even higher turnover rate and lingering issues with disengagement and low morale.
The CEO had also been thinking seriously about his own succession for years. He was not far from retirement, and the organization’s dependence on him was something he could name even if he could not quite resolve. The succession conversation, in every form it took, circled back to the same question: where do you find someone who could do what he does?
When he encountered organizations like the one in the previous section (and he did, because he was curious and well-networked and genuinely looking for models), what he saw was a leader with particular traits. Data-driven. Decisive. Disciplined. He took notes. He identified the practices he might adopt: a legacy giving circle, a professional advisory council, a structured development hire. These are good observations. The practices are genuinely worth examining. But the adoption that followed was additive. New items on an already overloaded agenda. New frameworks layered over an unchanged underlying structure. The development initiative launched, but it required his personal involvement to maintain momentum. The advisory council formed, but the relationships lived in his calendar rather than in the institution. The strategic plan was updated to include planned giving language, but without the prior shifts that would make that language generative rather than aspirational.
The ceiling didn’t move. And the conclusion he and his team quietly reached, because it is the conclusion the available frameworks tend to produce, was that he hadn’t yet found the right person, or the right tool, or the right approach. And, that if he kept looking, he would.
What the Two Stories Share
It would be easy to read these two composites as a contrast between a better leader and a lesser one. That reading would be both understandable and wrong. And the fact that it’s the most available reading is itself part of the argument.
The CEO in the second story is not failing because of who he is. He is operating, with considerable skill and genuine commitment, inside a set of structural conditions that make the ceiling he keeps hitting almost inevitable. The complex board wasn’t assembled carelessly; it reflects real governance requirements and years of institutional history. The inner circle that effectively runs decisions isn’t a power grab; it is what the architecture makes nearly necessary when a large, structurally complex board lacks the conditions for genuine deliberation. The individual conversations that consume his calendar aren’t a personal habit he could simply decide to change; they are what the architecture requires. The psychometric inventory isn’t vanity; it is a reasonable response to a genuine problem, pursued with the tools the professional culture made available.
What those tools share (and this is the structural observation worth sitting with) is that they all point toward persons. Toward traits, styles, types, and individual capacities. They rest on an assumption so deeply embedded in twentieth-century institutional thinking that it rarely gets examined: that the relevant features of a person—their intelligence, their leadership capacity, their temperamental orientation—are essentially fixed, and that the work of management is to identify, sort, and deploy those fixed qualities effectively. Three decades of research in neuroscience, cognitive development, and organizational behavior have substantially complicated that assumption. But the tools built on it remain the default vocabulary of leadership and governance. They are frameworks for classifying people rather than frameworks for examining what conditions have been built and what those conditions reliably produce.
I want to be careful here, because I have participated in these conversations. I have sat across from leaders like him and helped them look for better people, better assessments, better frameworks for understanding the individuals in the room. It took me longer than I’d like to admit to recognize that I was helping with the wrong question. Not because the question was unintelligent, but because the institutional vocabulary available to both of us kept pointing in the same direction. Toward persons. Toward character. Away from structure.
And even now, having named this pattern clearly enough to write about it, I notice that my own thinking still defaults to the same orientation. When I sit with a leader who is stuck, my first instinct is to diagnose what they are not seeing, which is itself a person-centered move. The structural questions—What conditions is the structure of this conversation creating? What do those conditions make possible or foreclose?—these still come second, if at all. For too long (and still too often, if I’m totally transparent), I saw this as a personal failing. I think it is what the available professional frameworks produce. Coaching, consulting, mediation, organizational psychology, leadership development; nearly every discipline that puts advisors in the room with leaders orient us toward the personal: the individual across the table; my personal experience, knowledge, training, and role as an advisor; the people who need to be “on the bus” before we can decide where the bus needs to go.
The pull is structural. Recognizing it does not make you immune to it. It does, though, mean you can sometimes catch yourself mid-default, and ask a different question.
The CEO in the first story did not escape this pull because he was wiser or more self-aware. He escaped it, largely without knowing he was escaping it, because his prior training had given him a different default orientation. Not toward who people are, but toward what conditions produce what behaviors. Not toward finding the right person, but toward building the environment in which the right behaviors become more likely. That is a different question. It produces different organizations.
This is what the LinkedIn post and comments get wrong when they conclude that culture can’t scale, that leadership can’t be replicated, that the “people side” is always the limiting factor. And… It’s worth pausing on the word “culture” for a moment, because it may be doing more harm than good here. The word, like so many managerial abstractions we’ve inherited, functions as a catch-all that collapses specific, observable things into a single concept that then feels either inevitable or impossible to change. What researchers who study organizational behavior most reliably find is not that “culture” drives outcomes, but that specific, measurable conditions do. The behavioral norms that govern how disagreement is handled in a meeting. The decision-making practices that determine who gets consulted and when. The communication habits that signal whether speaking up is genuinely safe or merely officially permitted. And the governance structures that distribute accountability rather than concentrating it in one indispensable person. These are not cultural abstractions. They are practices. They can be named, examined, and deliberately built. And unlike a personality, they can outlast the person who first embodied them.
What doesn’t scale is the illusion that an organization is its leader. Or that “culture” is simply leadership personality writ large, rather than a set of conditions that can be deliberately built. What does scale, and what the first CEO built (largely without naming it as such), is the architecture that makes leadership itself a shared, distributed function rather than a solo performance.
What Would It Take to See This Clearly?
The two composites in this article are not meant as a verdict. They are meant as a mirror. One that most of us, if we’re honest, can find ourselves in at least partially, at least some of the time. I have been in both rooms. I have been the advisor who helped someone look for a better person when the more useful question was about the architecture we were both working inside. And I have watched my own thinking default to the person-centered frame even after learning to name the structural one. That recognition didn’t come quickly, and it didn’t come from a framework or an assessment. It came from sitting with a kind of productive discomfort long enough to ask a different question.
What follows are not recommendations. They are invitations into the conversations that, in my experience, tend to open something up, in leaders, in boards, in teams, and in the advisors and partners who work alongside them.
These are worth sitting with slowly, and worth having with others rather than alone.
- When your organization faces a significant decision (a strategic shift, a leadership transition, a funding challenge) where does the thinking actually happen? In what room, with whom, and under what conditions? And how does that compare with where it’s supposed to happen? Or where it would be most effective in the long-run?
- If your most effective leader stepped away tomorrow, which parts of what he or she does would continue (because they are embedded in structures, practices, and shared commitments) and which parts would walk out the door? What does your honest answer tell you about what you have actually built?
- Think about the last time your organization added a new initiative, framework, or strategic priority. What, if anything, was examined, renegotiated, or set aside to make room for it? If the answer is nothing, what does that suggest about the underlying architecture rather than the quality of the new initiative itself?
- Where in your organization do people say what they actually think? And where do they say what is expected or safe? What specific conditions produce each of those environments? And who, if anyone, is responsible for examining that difference?
- What would it mean to build something that outlasts you? Not as a legacy project or a succession plan, but as the ordinary, daily work of distributing the capacity to lead, decide, and hold the organization’s purpose? What would you have to stop doing for that to become possible?
Randal Evans is a philanthropic and legal counselor, strategic advisor, and Chartered Advisor in Philanthropy® (CAP®) based in Scottsdale, Arizona. He works with families, foundations, and mission-driven organizations on charitable planning, governance, and leadership. More at randalevans.com.