On The Balcony

Some challenges don't fail because we lack intelligence, expertise, or good intentions. They fail because the systems meant to hold them — the structures, relationships, and shared stories — aren't strong enough to carry the weight. In this episode of On the Balcony, Michael Koehler sits down with Tim O'Brien to explore one of the most quietly powerful ideas in Adaptive Leadership: the holding environment. At the center of the conversation is a real public case — Gina Raimondo's leadership of pension reform in Rhode Island — where the technical problem was solvable, but the adaptive challenge was immense. Retirements, livelihoods, and deeply held beliefs were at stake. Data alone couldn't move the system. Logic was not enough for people to absorb the loss. What made progress possible was the deliberate construction of a holding environment — one capable of containing fear, grief, anger, and conflict long enough for new meaning to emerge. Tim and Michael use this case to unpack what holding environments really are — not abstract "safe spaces," but designed conditions that help people stay in hard conversations without fleeing, fixing, or polarizing. What You'll Explore in This EpisodeWhat a holding environment actually is. Holding environments are the structures, relationships, and shared stories that make it possible for people to engage adaptive challenges without becoming too overwhelmed. As Tim describes it, a holding environment is not about removing distress — it's about recognizing and legitimizing what people are already carrying. The three components of a holding environment. The conversation explores structures and boundaries (time limits, spatial design, process clarity, and role boundaries all matter — from how long a meeting lasts, to who holds the microphone, to how a forum is framed); relationships both horizontal and vertical (holding environments depend on the quality of relationships among peers and the relationship between people and authority — trust, legitimacy, and containment travel through these relational channels); and story, meaning, and purpose (facts matter, but they must be held within a shared narrative — in Rhode Island, Raimondo's "Truth in Numbers" report didn't just inform, it created a common reality people could argue within, rather than argue about). The Rhode Island pension reform case. The episode walks through how Raimondo resisted the pressure to act as a technical savior and instead orchestrated a process where loss could be named, anger expressed, and responsibility shared. Public forums, clear data, and repeated engagement weren't accidental — they were elements of a holding environment intentionally designed to stretch the system's capacity. Why some systems collapse under pressure. Many organizations already have holding environments — but not ones strong enough for the challenges they're facing. When the heat exceeds the container, people disengage, scapegoat, or polarize. Exercising leadership often means strengthening the container rather than supplying answers. Holding environments vs. psychological safety. The conversation distinguishes between team-level psychological safety and the broader, more demanding work of holding environments — especially in public or cross-boundary systems where authority is diffuse and stakes are high. Quotes from This Episode"A holding environment might be a place where one's inner world is recognized, legitimized, or validated." — Tim O'Brien "She creates a space where cognitive and emotional turmoil could give way to meaning. People are upset, angry, full of rage — but something has to be done." — Tim O'Brien "They're not forging lifelong relationships, but on this particular issue they're meeting the other people who are implicated —...