12 Questions to Ask Before Hiring a Fractional CTO

Why the questions matter

A fractional CTO gets deep access to your product, team, vendors, and investors. The title is used loosely, so the interview should establish what this person has actually done, how they will work with you, and whether their incentives match yours.

Experience

Listen for specific stories with trade-offs and mistakes. A list of technologies tells you very little.

• Which products have you led technically, and what was your exact role?
• Have you led engineering teams of the size we will need in the next year?
• Have you worked at our stage before (pre-MVP, first release, or scaling)?
• Can I speak with a founder or CEO you have worked with?

Independence and incentives

Your fractional CTO should be on your side of every vendor negotiation.

• Do you receive any commission or ownership from development vendors you might recommend?
• Are you part of an agency that would want to do the build?
• Who will own our code, cloud accounts, and documentation?

Working model

A good answer includes a concrete first-month plan: discovery, a written assessment, and the first decisions.

• How many days or hours per week, and how are urgent issues handled?
• What will you deliver in the first 30, 60, and 90 days?
• How do you report progress to me and, if needed, to the board?

The end of the engagement

A fractional CTO should plan to make themselves less necessary over time: documented decisions, a capable team, and a smooth handover when a full-time leader arrives.

• How will we know when it is time to hire a full-time CTO, and will you help us hire them?