Questions to ask a fractional CTO

How to use these questions

You do not need to ask all of them. Pick the groups that match your worries, ask every candidate the same ones, and write down what each person says. Comparing answers side by side after the calls is far more useful than relying on how each conversation felt.

Bring something real. If your biggest question is whether to replace MyCase or keep it and add integrations, say so and ask how they would decide. A candidate's reasoning about your actual situation tells you more than their résumé. If you are comparing a scoped provider such as InTheory against a broader fractional CTO, the same questions work for both.

Experience and fit

Listen for named systems and concrete outcomes. A good answer to the second question sounds like: we moved a 20-person firm off a legacy system, cleaned up duplicate contacts first, and ran both systems for two weeks. A weak answer is a list of logos.

If the candidate has no experience in your exact field, that is not disqualifying. Ask how they would get up to speed, which people they would talk to first, and what they would read. A thoughtful plan for learning your business is worth more than a claimed specialty.

• Which businesses similar to ours in size and type have you worked with recently?
• What systems in our field have you set up or migrated, for example Clio, Dentrix, ServiceTitan or Karbon?
• Tell me about a recommendation you made that the client did not take. What happened?
• Tell me about a time you advised a client not to buy or build something.
• Who would actually do the work: you, a junior colleague, or a development partner?

Approach and method

The answer you want for the first question includes talking to the people doing the work, timing the current process and reviewing what you already pay for. If a candidate proposes a platform before understanding the workflow, that is a warning sign.

Ask a follow-up on prioritization as well: if we could fix only one thing this quarter, how would you choose? Good answers weigh frequency, cost, risk and how ready the team is to change, and they admit that the first choice may be a small one chosen because it is likely to work.

• What would you do in the first 30 days?
• How do you choose which problem to work on first?
• What would you measure before changing anything?
• How do you write acceptance criteria, and who signs them off?
• Where in this workflow would a person need to review or approve output?

Money and incentives

Referral relationships are not automatically bad, but they must be disclosed. The best answers on cost include running costs after launch, not just the build. Published benchmarks put fractional CTOs at roughly $150 to $250 an hour, so ask how hours translate into deliverables.

Follow up on running costs with one concrete request: estimate our total monthly software spend a year from now if we follow your plan. A candidate who has thought it through will give a range and explain what drives it, such as added seats, automation volume or AI usage. One who has not will change the subject back to their own fee.

• What exactly is included in the monthly fee, and what is quoted separately?
• Do you earn margins, referral fees or commissions on any software or services you recommend?
• Do you have a development team or agency you would route build work to?
• What do you expect our software and usage costs to be after launch?
• How would we know, in numbers, whether this engagement was worth the fee?

Data, security and compliance

For a dental practice the last answer should mention HIPAA. For a law firm, confidentiality and ABA Formal Opinion 512. For an accounting firm, the FTC Safeguards Rule. The candidate should raise these questions without claiming to give legal advice.

Ask one more practical question: what would you never put into an AI tool? A careful candidate will name specific data, such as social security numbers, privileged communications or patient records, and explain the controls they would want first.

• Which AI services would you use with our data, and do they train on it?
• Will all accounts and credentials be in our company's name?
• How do you handle access for yourself and anyone working with you?
• What would you check before turning on an AI assistant across our email and files?
• Which regulations would you expect our counsel to review for this work?

Questions a good candidate will ask you

Pay as much attention to what the candidate asks as to what they answer. Strong fractional leaders interview the business. Expect questions like these, and be wary if you hear none of them.

If a candidate asks about your clients, your margins and your staff before they ask about your software, that is usually a good sign. Technology choices in a service business follow from how the business earns money, and the best leaders start there.

• Which workflow costs you the most time or money today, and how do you know?
• What have you bought in the last two years that did not work out, and why?
• Who on your team would own this work between our meetings?
• What does a good outcome look like to you in 90 days, in numbers?
• Which decisions do you want to keep for yourself?
• Are there client contracts, insurance requirements or regulations that limit what we can do with data?

Adoption, exit and fit

A candidate who has never thought about adoption has probably delivered tools that sat unused. Good answers mention training the people who do the work, an internal owner for each tool, and retiring the old way of doing things so staff are not running two processes. On exit, a strong answer is a living document of systems, decisions, access and open risks kept current throughout, which is something InTheory treats as a standard deliverable.

• How do you get staff to use a new tool once it is live?
• What usage numbers would you review after 30 days?
• What does your handover document include if we part ways?
• What notice period do you need, and what happens to work in progress?
• How many clients do you work with at once, and how quickly do you reply?