The Legibility Gap: Why Systems Ignore Transformative Success

This is Week 2 in a 12 Week Series on Systems-based Leadership.

Many leaders often operate under the delusion that evaluation systems are neutral mirrors reflecting organizational health. In my analysis of institutional behavior, I have found that metrics are rarely objective; they are encoded definitions of success inherited from the past. Evaluation frameworks—often categorized as Key Performance Indicators (KPIs)—act as the political architecture of the status quo. They privilege continuity over transformation because they were built to optimize the very structures that “innovation” seeks to disrupt.

When an executive confuses measurement with truth, they cede their agency to the legacy algorithm. This creates a dangerous feedback loop where only familiar outcomes are rewarded. If we define “production” only through the lens of historical metrics, we inadvertently stifle any outcome that doesn’t immediately translate into old forms of currency. This is how organizations become “efficient” at producing results that are increasingly irrelevant to the flourishing they claim to seek.

“I have found that metrics are rarely objective; they are encoded definitions of success inherited from the past.”

I am the former, Founder and Executive Director of Prep School for Global Leadership. It was a school that lived out the full life of its contract.  But, in the backdrop of almost 10 schools facing closure, I was the only one to not seek a renewal. I knew in my spirit that there was more that I wanted my school to do and I wanted a different contractual relationship that would allow it.

In the landscape of school reform, my school was designed for the “disposable”—a school specifically populated by students whom traditional districts had expelled through expulsion or chronic exclusion. These were children carrying the heavy weight of academic trauma, behavioral disruption, and a profound, earned distrust of the institutional gaze. Within eighteen months, the environment underwent a visible chemical shift. Attendance stabilized not through mandate, but through belonging; behavioral incidents plummeted; and for the first time in their lives, students’ “Hope Scores”—a validated metric of psychological agency—ascended significantly. We were witnessing a fundamental change in the students’ relationship to learning itself.

Yet, as the executive lead, I watched a secondary and more clinical reality unfold simultaneously. The authorizers and traditional funders who held the school’s life in their hands wanted the traditional currency of standardized growth percentiles and credit acquisition rates—metrics that are often lagging indicators for a population in the midst of a foundational identity shift. The system was presented with a miracle of human transformation, but because that transformation did not use the vocabulary of the existing spreadsheet, it was treated as an anecdotal bonus– but not the work itself.

So I chose not to fight for a renewal.  My refusal to fight was not a surrender; it was a diagnostic conclusion. I realized that the school was not being judged on a failure, but on my unwillingness to prioritize only what the authorizer could measure. It’s ‘illegibility.’ We were producing a version of success that the system’s sensors were literally incapable of protecting. 

“The system was presented with a miracle of human transformation, but because that transformation did not use the vocabulary of the existing spreadsheet, it was treated as an anecdotal bonus– but not the work itself.”

That experience taught me that resistance to new outcomes is rarely a matter of individual malice; it is a matter of systemic homeostasis. Systems are designed to preserve their current state. Whether in healthcare, government, or the nonprofit sector, I have observed how risk aversion and validation cycles create a structural gravity that pulls initiatives back toward the center. Funding incentives are almost always tied to “proven” models—a coded term for models that do not challenge the underlying distribution of power or the existing metrics of success.

This preservation logic ensures that the system rewards familiar outputs even when superior outcomes are present. To a governing body, a predictable “average” result is often safer than an exceptional result that requires a new way of counting. We must acknowledge that systems prioritize institutional safety over transformative risk. When progress feels stagnant despite high activity, the culprit is usually the validation cycle that demands we prove our worth using the tools built to limit our scope.

“Systems are designed to preserve their current state. Whether in healthcare, government, or the nonprofit sector, I have observed how risk aversion and validation cycles create a structural gravity that pulls initiatives back toward the center.”

From the executive seat, this creates a profound dilemma: one can produce genuine transformation and be structurally punished for it. This is not a failure of character, but a collision with “institutional legibility.” The leader is forced to choose between designing for real, material flourishing or designing for the metrics the system is currently capable of recognizing. To choose the former risks the survival of the entity; to choose the latter risks the integrity of the mission.

My work has taught me that this is the primary site of systemic failure. Visionary leaders often break here because they find themselves managing a “double bottom line” where human success is disconnected from institutional data. We must stop framing this as a moral choice and start seeing it as a design problem. The executive’s role is not just to produce the result, but to labor over the translation—to build the bridges between “new production” and “old systems” until the architecture can be re-engineered to recognize the change.

“The leader is forced to choose between designing for real, material flourishing or designing for the metrics the system is currently capable of recognizing. To choose the former risks the survival of the entity; to choose the latter risks the integrity of the mission.”

This invisibility is a universal constant for leaders in any sector—districts, foundations, or startups—who are moving beyond the status quo. You likely feel the exhaustion of seeing progress that “doesn’t count.” You are told your results are exceptional but “unreliable” because they do not fit the current evaluative syntax. You find yourself chasing metrics that distort your mission simply to maintain institutional standing, all while watching lives change in ways the data will never capture.

As a systems theorist, my diagnosis is clear: The problem is not your lack of results, but the misalignment of the engine of evaluation. The question is rarely, “Are we changing lives?” The question is, “Is our system built to recognize the change we say we want?” If the architecture is designed to hide your progress, then your most important act of leadership is not more activity, but a radical ownership of the evaluation itself. 

“If the architecture is designed to hide your progress, then your most important act of leadership is not more activity, but a radical ownership of the evaluation itself.”

We must own the architecture of how we are seen, or we will continue to be erased by the very systems we are trying to evolve.