CEO Replaces Annual Strategy Offsite With a 1,842-Word Prompt

At 8:07 a.m. Monday, the CEO canceled the company’s annual strategy offsite after the resort had placed fruit beside the conference-room water glasses. In its place, the executive team received a 1,842-word prompt requesting a multi-horizon strategy, a concise leader post, and a list of decisions requiring no further discussion. The resort released the room to a wedding party.

The first dispute began before lunch. The CFO argued that “think deeply” had to appear before “be concise,” since the company could not compress an idea before producing one. The COO put “be concise” first to prevent the resulting answer from becoming 90 pages. The disagreement concerned precedence, not meaning: whether concision should limit thought or thought should expand until concision became an aspiration. The CEO returned both drafts with one instruction: make the prompt resolve the disagreement.

Legal joined on the second day after an executive asked whether the prompt’s instructions applied to one another. Counsel logged 86 tracked changes, including a proposal to define “deeply” in a footnote and a counterproposal to remove the footnote for length. A new change asked who would determine when enough thinking had occurred.

By the third day, no product, hiring, or market decision had been approved. The CEO called the unresolved order a useful strategic signal and moved the competing versions into the board packet as the company’s primary strategy deliverable. The final prompt instructed the eventual response to synthesize the discussion, identify unresolved disagreements, and state which decisions required no further discussion. At 4:12 p.m., the concise leader post went out with the two instructions on separate lines and the cursor blinking between them.