Why Retreats Don’t Work

There is a version of this problem you have probably lived through. A leadership team spends three days off-site. The conversations are good — honest, even. People say things they don’t usually say. Something shifts. They return on Monday with renewed purpose, a shared vocabulary, and a list of commitments. By the following Friday, the meetings run the same way they always ran. The language fades. The commitments become agenda items, then history.

This is not a failure of sincerity. The people in that room meant what they said. It is a failure of formation theory — a misunderstanding, usually unexamined, of how human beings actually change.

Insight is not enough

Aristotle’s claim is precise and still underappreciated: character is not chosen, it is formed through repeated action. We become just by doing just things, courageous by doing courageous things. The retreat model inverts this. It treats insight as the agent of change — as though understanding something differently is sufficient to become someone different. Aristotle knew better. Insight without practice is inert. What changes a person is not what they come to believe but what they do, repeatedly, in conditions that make that practice possible.

John Dewey followed this argument to its institutional implications. Experience, for Dewey, is educative only when it is structured to produce growth. The structure is not incidental. It is what forms. An organization that wants to form people in a particular direction has to ask: what does daily life here actually practice? What habits does the rhythm of this place reinforce — not in theory, but in the aggregate of ten thousand small interactions over time? Dewey would not have been surprised by the Monday return. The structures were unchanged. Of course the people reverted. They were still being formed by the same environment that formed them before they left.

The environment is never neutral

James Gibson was thinking about perception, not character. But his concept of affordances carries direct implications for how we think about formation. An affordance is a possibility for action offered by an environment to an organism capable of taking it up. The environment is not neutral. It actively shapes what is perceived as possible, what is reached for, what is ignored. A well-designed environment makes certain actions easy, natural, almost inevitable. A poorly designed one makes them effortful, unlikely, or invisible.

Organizations are environments. They afford certain behaviors and inhibit others — not through policy alone, but through architecture, rhythm, proximity, incentive, habit, and the subtle grammar of who gets listened to in which rooms. When the structure of a place affords defensiveness, people will be defensive, even people who have just committed, in a mountain lodge, to something better. The affordances win. They always win.

This is why formation is a design problem. If you want people to act with integrity, build structures that make integrity the easier path. If you want genuine accountability, design conditions where accountability is practiced repeatedly, not invoked once a year in a review cycle. The retreat cannot do this because it does not touch the affordances. It changes what people believe, for a moment, without changing what the environment makes available.

The question organizations aren’t asking

The practical implication is uncomfortable: most of what organizations spend on leadership development is spent in the wrong place. Not because the content is wrong. Often it is excellent. But content delivered outside the forming environment cannot form. It can inform, inspire, even move — and then the Monday structures reassert themselves, and the forming continues exactly as before, by default rather than design.

Formation by design means asking a different set of questions. Not: what should people know or believe? But: what does this place practice? What do our rhythms reward? What do our structures make easy, and what do they make nearly impossible? Who is actually being formed here, into what, and is that what we intend?

The gap between what an organization claims to value and what it actually produces in people is rarely the result of bad intentions. It is almost always the result of design that was never pointed at formation in the first place.

Aristotle would have recognized the problem immediately. Gibson would have told you where to look. Dewey would have told you what to do about it.

The retreat was never going to be enough. The question is what comes next.


Brian Jenkin, PhD — Principal & Founder, VIA Forma