Unlearning Success: Why organizations need mirrors, not manuals

Every organization claims to value learning. Yet most only value it in hindsight, when things go wrong. We launch post-mortems, conduct root-cause analyses, and tweak processes. But rarely do we pause to ask the deeper question: Why did our way of thinking make that error possible in the first place?

Chris Argyris called this the difference between single-loop and double-loop learning — the act of not just correcting mistakes but questioning the underlying assumptions that created them. His insight remains one of the most radical in modern management thinking, precisely because it demands that we turn the mirror inward.

The problem with success

Argyris observed that the most accomplished people often struggle the most with learning. They’ve been rewarded for having answers, not for asking better questions. Inside many organizations today, this same logic is institutionalized. Success metrics, performance ratings, and board dashboards all reinforce a culture of knowing. Reflection, doubt, or vulnerability are treated as inefficiencies.

And so, we build systems that optimize for control — not curiosity. We hire people to think critically, yet penalize them when they question the logic of the system itself. We celebrate agility, but reward predictability. The result? Organizational brittleness masked as brilliance.

Single-loop learning feels productive — it’s fast, visible, and linear. Something breaks, we fix it. A customer complaint, we train our service team. When a product flops, we adjust the feature. Yet each of these responses stays within the same mental model that produced the issue. The loop stays closed.

Double-loop learning, by contrast, demands humility. It begins with the sentence every leader resists most: Maybe the way we define success is part of the problem. This kind of inquiry slows us down at first, but over time it builds resilience. The ability to adapt not just to changing conditions but to our own blind spots.

In most companies, defensive reasoning isn’t an individual quirk — it’s a cultural artifact. We avoid uncomfortable truths under the banner of professionalism. We equate composure with competence. We mistake politeness for trust. Over time, this creates what Argyris called skilled incompetence: teams that are brilliant at avoiding the very conversations that would help them grow.

Breaking this pattern requires psychological safety, yes — but more importantly, cognitive safety. People must feel safe not just to speak, but to think differently. The work is not to make everyone comfortable; it’s to make learning inevitable.

Learning as collective intervention

In a systems-thinking frame, learning is not an event; it’s a field phenomenon. The intelligence of an organization emerges from the quality of its relationships, not the IQ of its leaders. When we introduce reflection loops — spaces where people can safely surface assumptions, test beliefs, and examine decisions — the organization itself becomes more conscious.

This is where Argyris’s work meets the frontier of systems leadership. Single-loop learning changes outcomes. Double-loop learning changes beliefs. But there is a third loop that some organizations are now daring to enter: generative learning — where people not only question assumptions, but collectively redesign the very systems that shape them.

The purpose of double-loop learning is not self-critique for its own sake. It is to restore coherence between what we say we value and how we actually behave. Every leadership team that commits to this practice begins to sense a quiet shift: from reactivity to responsiveness, from fear to inquiry, from fragmentation to flow.

Learning, then, is not a skill to be taught. It is a field to be tended. And like any living system, it grows in the presence of truth. The leaders of the future will not be those who know the most, but those who can stay most open — especially when they’re right.