Most non-technical founders hire their first technical leader and find out — too late — that the person they picked won't actually be there in six months. These ten questions filter the reliable ones from the rest. Use them on the first call.
Why this list exists
I've watched founders go through 2–3 fractional CTOs in a year before finding someone who stuck. Every story has the same shape: the first CTO sounded great in the sales call, then went quiet somewhere around month two.
These questions exist to surface the difference between a sales pitch and a working partnership. They don't require you to be technical. They just require you to listen for vague answers.
Use them on the next intro call. Take notes. If you get vague on three or more — keep looking.
Fractional means split attention. 2–3 is sustainable. 5+ means you'll be in the queue every time something breaks.
Green flag
A specific number, with what each one gets in hours per week.
Red flag
Vague answer, “as many as fit”, or 6+ active retainers.
A good fractional CTO plans for their own departure. A bad one makes themselves indispensable, and you can't leave without breaking the product.
Green flag
Documentation standards, named successor, knowledge transfer scheduled.
Red flag
“We'll figure that out later” or no clear thought.
Best filter of all. Anyone who refuses or stalls — has a reason.
Green flag
Yes, with one or two intros within a week.
Red flag
“They're all under NDA” with no exception. Clients can usually vouch — name + two sentences is fine.
Some CTOs stopped coding years ago. That's fine — but you should know which kind you're hiring. If they claim to ship and lead, ask for both.
Green flag
Real repos, even small ones. Diffs they wrote, not just reviewed.
Red flag
Everything under NDA with no exception, or hand-waving about “high-level direction”.
This separates “I have a process” from “I'll figure it out as we go.” You want a process.
Green flag
Specific phases — discovery, audit, plan, first deliverable — with rough week-by-week.
Red flag
Generic “I'll get up to speed” with no structure.
A solo fractional CTO scales to one project. Yours might need more — design, infra, mobile, QA. “I do everything myself” means you'll hit a ceiling fast.
Green flag
A small network of people they've shipped with before. Names, roles, how vetting works.
Red flag
“I do everything myself” or “I'd hire from Upwork as needed”.
Everyone has one. People without an answer are either inexperienced or hiding something. People with a thoughtful answer have learned from it.
Green flag
Specific story, what went wrong, what they'd do differently.
Red flag
“Never had that happen” or excessive blame on client/team.
Filters equal quality. A CTO who takes everything is a mercenary, not a partner. They should have opinions about where they don't belong.
Green flag
Specific filters — industry, stage, founder type, tech stack.
Red flag
“I work on anything” or “I take what pays”.
You will disagree. Method matters. A good CTO pushes back on the call, then commits. A bad one either rolls over or fights for weeks.
Green flag
“I disagree on the call, write up my reasoning if it's serious, then commit to your decision.”
Red flag
Stories of long arguments, going around founders, or never disagreeing with anyone.
Hours on paper ≠ hours of attention. Get specifics about response time, deep work blocks, meeting cadence.
Green flag
Specific schedule — deep work blocks, async by default, response within X hours.
Red flag
“It depends” or “whenever you need me” without structure.
Free 15-minute intro call. No deck, no pitch. Bring this list, ask whichever ones you want, and decide if I'm worth a second conversation. If not — at least you now know the questions for the next one.
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