Scaling Up Business with Bill Gallagher · 2026-06-17 · 14 min
Every CEO story gets told from the leader’s chair. Episode seven of the Busy Is Broken series flips the camera. Bill walks through four composite vignettes - anonymized but visceral - drawn from real teams he’s coached. Each one shows what a leader’s patterns look like from the other side of the table. If you manage people, those people have a version of one of these stories. They’ve probably stopped trying to tell you. The Chaotic Team: a chief of staff opens her phone at 5:30 AM to find 3 AM messages rearranging tomorrow’s priorities. Operational meddling and strategic absence at the same time - the leader is everywhere on detail and nowhere on direction. The Unsafe Team: meetings opened with problems, never connection. Every new book the CEO read triggered a new system. People tapped out alongside a leader who slept two hours a night. They were tired of sprinting after gusts of wind. The Resigned Team: “This is how it is.” They’d moved past hoping things would change. No one was angry anymore. That’s worse than anger. The Frozen Team: everything waited on the founder. A gentle, patient, permanent freeze. Lovely people making a lovely product. But they were helpers, not leaders.
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