The CTO Transition
A transition is usually counted from the first working day. For a CTO that is late: by then the company, the task and the people are already chosen. The four phases are linked — weak research weakens the contract, a weak contract hampers diagnosis, and rushed diagnosis leads to the wrong changes.
−30 — researching the market, the business model and the map of tensions, where interviews work as a mutual check. 00 — the commit point where expectations become a mutual contract. 30 — diagnosis: one question yields four versions of the company, so the map is built by triangulation. 90 — one or two systemic bets and a first result that earns trust.
The model has two milestone artifacts: a company map by day 30 (people, money, flow, risks, hypotheses, questions) and an updated contract by day 90 (diagnosis, the year ahead, changes, cadence, metrics, team). Red flags are not a separate final phase — they run through the entire transition. A first result is due by day 90 because decision-makers cannot observe the quality of your learning; they can observe whether the company has become clearer.
Start the clock a month before day one: study the business model, external technical signals and the power map while you can still walk away.
At the commit point fix a mutual contract: outcomes, authority, resources, constraints and success criteria.
Deliver a company map by day 30 and an updated contract by day 90, and handle red flags as they appear rather than at the end.