Fractional CTO Starter Checklist

The question companies forget to ask before hiring a fractional CTO is not "do we need one?" — it is "what will success look like in ninety days?" Without a written answer to that question, the engagement drifts into vague technical advisory that produces no accountability. This checklist lives on the company side: the setup work before the CTO''s first day so their time is spent on technical decisions, not organizational politics. Key pre-engagement work includes defining the technical metrics that matter most (sprint velocity, incident frequency, deployment cadence), identifying the architectural decisions that have been deferred and are now creating risk, and getting leadership alignment on what the CTO owns and how they interact with the engineering team. Also establish before day one: what access does the CTO need on day one (read access to all repos, monitoring tools, project management), which meetings should they attend (weekly leadership, sprint ceremonies, board calls if needed), who do they escalate technical decisions to when rapid resolution is needed, and what is the expected response time for questions from the engineering team. A CTO who arrives with clear success criteria and stakeholder alignment produces their first meaningful deliverable in weeks — not months. The companies that get the most from their fractional CTO arrive with a written problem statement, alignment on what the CTO owns and does not own, and a clear answer to the question "what does success look like at 90 days?"