Coming into a new engineering org as a fractional CTO means earning trust fast. This checklist covers what to gather, what to ask, and what to produce in the first two weeks to establish authority.
Week 1 — Access & Discovery
- Get GitHub / GitLab org access and clone main repos
- Review last 6 months of incident reports and postmortems
- Map the current infrastructure and hosting stack
- Interview each engineering team lead (30 min each)
- Review open engineering headcount and active job reqs
Week 1 — Key Questions
- What is the biggest technical risk to the business right now?
- Where does engineering consistently slow the product team down?
- What has been tried and abandoned in the last 12 months and why?
- What does the board / CEO think engineering should prioritize?
- What does the engineering team think leadership misunderstands?
Week 2 — First Deliverable
- Produce a 2-page technical health scorecard
- Flag the 3 highest-severity risks with remediation estimates
- Identify 2-3 quick wins executable in 30 days
- Propose a communication cadence with leadership
- Set explicit expectations around decision authority
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