If you want to know whether a strategy is actually working, who do you ask?
Most leaders ask the people closest to the work. It feels like the right instinct — get out of the C-suite, talk to the managers actually running programs day to day. My own research, and my own years sitting in that exact seat, point to something every executive should sit with before treating that feedback as the full picture: the answer you get depends entirely on where the person you’re asking sits in the organization, and that gap is wider, and more consequential, than most leadership teams realize.
The View From the Middle
I spent years as a director at a Fortune 10 health care company, in the layer of the organization that sits between strategy and execution — close enough to the work to feel every resourcing gap, far removed enough from the C-suite that I rarely had visibility into why those gaps existed. What reached me were the announcements: a new strategic pillar, a new executive hire, a renewed sense that the organization was finally paying attention to an issue I cared about. What didn’t reach me, most of the time, were the budget conversations, the political resistance, or the quiet deprioritization happening one or two floors up. I had every reason to be encouraged. I just didn’t have the full picture.
That experience is what sent me looking for the pattern formally.
What the Research Confirmed
I studied two groups inside the same kinds of organizations: senior executives charged with building health equity strategy from scratch, and the middle managers responsible for carrying that strategy out. I expected their views of organizational progress to roughly align. They didn’t — not even close.
The executives, almost without exception, described frustration: insufficient budget, unclear mandates, leadership that wasn’t ready to engage with hard truths. The middle managers, working inside the very same systems, were largely optimistic. Many pointed to their leadership with real confidence — “we have a new Chief Diversity Officer who’s changing how we do business,” one told me — genuinely encouraged by signs of progress that, from one level up, looked more like the opening move in a fight than evidence of one being won.
Two Worlds, One Building
Neither group was wrong. They were looking at different parts of the same building. Middle managers typically don’t sit in the rooms where budgets get fought over or priorities get quietly shelved. What reaches them is the announcement, the new title, the renewed sense that someone is paying attention — genuinely meaningful information, just incomplete. Executives see the resourcing fights and the resistance up close, which gives them a more critical, and usually more accurate, read on how much has actually changed.
This is a hierarchy problem, not a people problem. It’s also not unique to health equity work — it’s a structural feature of how information moves, or fails to move, through any large organization.
Why This Should Concern Leadership
If leadership only checks in with the layer closest to execution, they will consistently get a rosier picture than the data warrants — not because anyone is misrepresenting reality, but because nobody in that conversation has visibility into the whole system. Optimism from the middle of your company is not the same as proof that your strategy is working, and treating it as confirmation is one of the easier ways for a leadership team to mistake activity for progress.
There’s a cost on the other side of this gap, too. The managers I studied, and the one I once was, had on-the-ground instincts that would have meaningfully sharpened the strategy — if anyone had asked before the rollout instead of after. Organizations that only use the middle layer to confirm what they already believe are leaving real strategic input on the table.
What Leaders Should Do Differently
Closing this gap doesn’t require another listening session. It requires building real lines of sight in both directions:
- Don’t mistake departmental optimism for system-level proof. Pair frontline sentiment with a direct, honest account from the people closest to the resourcing decisions — they’re rarely describing the same reality.
- Pull middle managers into strategy formation, not just rollout. The people executing the work often have the clearest read on what will and won’t function in practice, but only if they’re consulted before the plan is finalized.
- Give the middle layer enough context to see the whole system, not just their piece of it. Information flowing only downward as announcements, with none of the surrounding reality, produces confidence that isn’t actually earned.
That’s the actual work: an organization built to hear itself clearly, top to bottom — not one that mistakes the most reassuring answer for the truest one.
