What to ask before signing a fractional CTO contract.
Eleven questions a founder should put to a fractional CTO operator before signing the retainer. Asked in the last 15 minutes of the discovery call, they cut a wrong-fit retainer in 30 minutes instead of 3 months. Each question lists what a real answer sounds like and what a hand-wave answer sounds like.
TLDR
The discovery call is your last cheap moment to discover that the fit is wrong. Ask these eleven questions; if more than two get hand-wave answers, walk. The cost of cancelling a retainer in month four is roughly the cost of three months of retainer plus the opportunity cost of those three months, which is materially worse than a discovery call that goes nowhere.
Most founders treat the fractional CTO discovery call as a sales call where they are the buyer being sold to. That framing produces wrong-fit retainers because the founder asks soft questions ("what's your background", "what kinds of companies have you worked with") that any operator can answer well regardless of fit.
The framing that produces right-fit retainers is the opposite. The founder asks operational questions that are hard to bullshit. The operator's answers tell you whether they have actually held the seat before. Eleven questions, in roughly the order they should come up.
The eleven questions.
What's NOT included in the retainer?
Real fractional CTOs have a clear list of things they will not do (line management, daily standups, IC code authorship). Hand-wavers say "we figure it out as we go."
How many other retainers are you holding right now?
Real operators have a hard cap (usually 2-3 retainers). If they say "depends on the client" or "I am very flexible," they are stretched thin and your retainer will get the leftover hours.
What does a typical week look like?
If they cannot describe the rhythm in specific time chunks, they have not held the seat consistently. Listen for "weekly 1:1, agenda set the day before, async between for non-urgent items, two-hour response window during business hours for urgent items."
How do you handle senior engineering hires we want to make this year?
The right answer covers job description draft, technical screen design, panel interview, offer calibration, reference checks. The wrong answer is "I will jump in if needed."
Can I talk to two of your current or past retainer clients?
Real fractional CTOs have references that will pick up the phone within 48 hours. If they hesitate, ask why. Common honest reason is "yes but the engagement is under NDA on specifics; my reference can speak to working style." Acceptable. Unacceptable is "let me think about who to put you in touch with."
Is there a pilot, and what does walking away look like for both sides?
The 4-week pilot is industry standard for fractional CTO engagements. Either side can walk after. If the operator does not offer one, that is a flag.
How does this engagement end well?
Most fractional CTO retainers should end at 12-18 months when the company outgrows the shape. Asking the operator how they think about ending the engagement reveals whether they think long-term or whether they are trying to lock you in indefinitely.
What does the IP assignment look like, and are there exclusivity clauses?
Standard fractional retainers have work-for-hire on deliverables (architecture documents, hiring materials) but no broad IP assignment. Exclusivity is by industry, not by client; operators who promise exclusivity to every client are lying to one of you.
Tell me about a retainer that did NOT work out.
Every senior fractional CTO has had at least one engagement that ended badly. If they cannot describe one in specific terms, they are either lying or they have not done this enough. The story should include what they would do differently.
What happens if you are sick, unavailable, or sign your next client?
For solo operators or small studios, continuity needs a plan that is not "best efforts." Listen for named peers who can pick up the work, written documentation of decisions throughout the engagement, and a notice period.
What does the price not cover, and what triggers an uplift?
The retainer price covers the steady-state operating rhythm. Specific events (founder's investor diligence, an acquisition, a regulator audit) often trigger uplifts. The operator should be able to list the events that trigger them.
How to use the list.
Print or paste these eleven questions into the agenda for the last 15-20 minutes of your discovery call. Tell the operator at the start of the call: "I would like to spend the last 15 minutes on a list of specific questions. They are designed to surface fit fast."
The operator's reaction to that framing is itself a signal. A real operator says "good, that's how I would do it too." A hand-waver pushes back or tries to reframe the call back to general chemistry.
If more than two of the eleven get hand-wave answers, walk. The cost of walking after a 60-minute discovery call is 60 minutes. The cost of walking from a wrong-fit retainer in month four is three months of retainer plus the opportunity cost of those three months not having had the right operator in the seat. The asymmetry is severe.
Want to test these on a call?
QuantaLynk runs fractional CTO retainers from €8K per month, six month minimum after a four week pilot. Bring the list above to the discovery call; honest answers to all eleven are how the studio operates. First call is 30 minutes.
Read the retainer detail →