Technology Expert Hiring Checklist

Define whether you need strategy (architecture, decisions) or execution (building)

These require completely different profiles and should rarely be the same person.

List your current tech stack and identify the constraints

A good technical advisor must understand your starting point before recommending changes.

Identify the immediate problems (scale, security, speed, technical debt, team)

Specific problems surface whether you need a generalist CTO or a specialist.

Clarify your team size and their seniority

A technical leader for a 2-person team vs. a 20-person team is a very different role.

Determine the decision-making authority they'll have

Advisors without authority often create more friction than value.

Ask about experience at your company stage (pre-seed, Series A, enterprise)

Technical challenges and leadership needs differ dramatically by stage.

Request examples of technical architecture decisions they've owned

Decision ownership (not just advice) indicates hands-on experience.

Ask how they've handled technical debt and legacy system migrations

Most real-world technical work involves constraints, not greenfield builds.

Evaluate communication quality — can they explain technical concepts to non-technical stakeholders?

A CTO who can't translate technical reality to founders creates dangerous information gaps.

Document all architectural decisions with rationale (Architecture Decision Records)

Decisions without context are impossible to revisit or reverse intelligently.

Schedule regular demos or reviews of work in progress

Technology work becomes invisible without structured checkpoints.

Ensure the advisor works alongside your team, not around them

Good fractional CTOs mentor and build team capability, not create dependency.

Set security and compliance checkpoints as milestones

Security is easier to build in than bolt on — verify it doesn't slip.

Establish coding standards and documentation expectations upfront

Ensure all code is in version control and ownership is transferred

You should own all code produced during the engagement.

Request a system documentation handoff (architecture diagram, runbooks)

Undocumented systems become critical liabilities when key people leave.

Audit all credentials, secrets, and access before offboarding

Security hygiene at offboarding prevents future unauthorized access.

Capture open technical decisions and known risks in a shared document

Future hires need to know what tradeoffs were made and why.