10 Questions to Ask Before Hiring a Fractional CTO

"He seemed great on the call. Very confident. Said all the right things."

Last quarter, a SaaS founder reached out to me. She'd hired a fractional CTO three months earlier — someone she'd found through a referral — paid $12,000 a month for 12 weeks, and had almost nothing to show for it. No architecture plan. No hires made. No real technical decisions. Just a lot of Slack messages and one strategy doc that looked like it was written in an afternoon.

She'd burned $36,000 and three months of runway on someone who turned out to be a great talker but a mediocre executor. And the worst part? She didn't know what to look for in the first place. She'd never hired a fractional CTO before. Neither had anyone on her team.

This happens more than I'd like to admit. The fractional CTO market is growing fast, and not everyone in it is good. Some are incredible — exactly what early-stage founders need. Others are consultants who've rebranded themselves as "fractional executives" and are coasting on vague deliverables and monthly retainers.

So here's what I tell founders before they sign anything: ask these 10 questions. Push for specific answers. And pay close attention to the ones who hedge.

The 10 Questions — And What Good Answers Actually Look Like

These aren't gotcha questions. They're diagnostic. The right fractional CTO will answer them confidently, with specifics. The wrong one will give you generalities and pivots. Let's go through them.

Question 1: What startup stage do you specialise in?

This is the most important question and most founders skip it entirely. A fractional CTO who's great at taking a Series B company from 30 to 100 engineers is a completely different person to someone who helps pre-seed founders get their first MVP live on a $50K budget.

Good answer: "I work primarily with pre-seed and seed-stage startups. My sweet spot is the first 12-18 months — getting an MVP to market, helping founders make their first technical hires, and building the right foundation before scale becomes a problem."

Red flag answer: "I work with companies at all stages." That's either untrue or means they don't have a real specialisation. Generalists at this level are rarely great at any specific thing.

Question 2: How many clients are you working with right now?

A fractional CTO can realistically serve 2-4 clients well. Any more than that and you're getting scraps of attention. This isn't theoretical — I've heard founders complain that their fractional CTO takes 3 days to respond to a critical technical question because they're juggling six other retainers.

Good answer: "Right now I'm working with two other companies — one at pre-seed, one at seed. My cap is three clients so I can be genuinely available when you need me."

Red flag answer: "I have several clients across different industries." Vague. Push them for a number.

Question 3: Can you show me startups you've taken from idea to launch?

Anyone can write a strategy doc. Fewer people have actually shepherded a product from zero to live users. Ask for specific examples — company names (or anonymised if needed), what the product was, what their role was, and what happened after launch.

Good answer: "I worked with a fintech startup in 2024 — I helped them scope the MVP, chose their stack, ran the first sprint planning, and hired their lead developer. They went live in 14 weeks on a $60K build budget and closed their seed round six months later."

Red flag answer: "I've been involved in many early-stage projects across various sectors." No specifics = no evidence.

Question 4: What does your weekly engagement look like — hours, availability, communication?

You need to know exactly what you're buying. "Fractional" means part-time, but part-time means different things to different people. Some fractional CTOs commit 10 hours a week. Some commit 20. Some are available on Slack daily; others check in once a week.

Good answer: "I commit to 12 hours a week with your team — two focused work blocks plus a weekly leadership sync. I'm on Slack during business hours and I'll always respond to critical issues within a few hours."

Red flag answer: "I'm flexible and adapt to each client's needs." That's not an answer. Push for a number. If they won't give you one, that tells you something.

Question 5: How do you handle technical decisions when you're not in the room?

This is a leadership question, not a technical one. A good fractional CTO builds systems and creates decision-making clarity so the team doesn't grind to a halt every time they're not available. A weak one creates dependency — everything flows through them, which is unsustainable at part-time hours.

Good answer: "In the first month I establish decision frameworks with the team — what can developers decide themselves, what needs tech lead sign-off, what needs me. I document these and revisit them quarterly. My goal is to make myself less necessary over time, not more."

Red flag answer: "I stay closely involved and make sure I'm across everything." That's a bottleneck waiting to happen.

Question 6: What's your approach to technical debt vs moving fast?

There's no single right answer to this — but there's definitely a wrong one, and it's "avoid technical debt at all costs." At pre-seed, you need to move. At Series A, debt becomes a real problem. A great fractional CTO knows when to accept it, when to manage it, and when to fix it.

Good answer: "At your stage, some technical debt is appropriate — you're proving a hypothesis, not building a ten-year platform. I help founders understand which shortcuts are acceptable now and which ones will bite you later. We document the debt as we create it and plan to address it when you hit scale."

Red flag answer: "I always advocate for clean, well-structured code from day one." Sounds great. Will cost you four extra months and $80K in runway you don't have.

Question 7: How do you handle hiring — can you help me find and evaluate engineers?

For most non-technical founders, this is one of the highest-value things a fractional CTO can do. Writing job specs, reviewing resumes, running technical interviews, evaluating take-home assessments — most founders have no idea how to do any of this. If your fractional CTO can own it, that's massive.

Good answer: "I'll write the job specs, screen resumes, run the technical interview rounds, and make a recommendation. I've hired for X types of roles before and I know what good looks like. I typically charge $5K for a managed hire engagement if that's the focus."

Red flag answer: "I can advise on the process but the actual hiring is up to you." So you're still doing it alone. Not much value there.

Question 8: What happens if it's not working out — what's the exit process?

This is the question nobody wants to ask and everyone should. What's the notice period? What happens to IP and documentation? Who owns the relationships with contractors or vendors they've managed? Good fractional CTOs think about offboarding from day one — not because they expect to fail, but because they're professional.

Good answer: "We work on 30-day rolling terms. If either of us decides it's not the right fit, 30 days notice. During that period I'll document everything, hand over vendor relationships, and make sure your team isn't left hanging. All IP stays with you from day one."

Red flag answer: Hesitation, vagueness, or a long lock-in with no exit clause. If they're confident in their work, they don't need you locked in for six months.

Question 9: Do you have equity expectations, or is it fee-only?

Both models exist and both can be fair — but you need to know upfront. Some fractional CTOs charge a lower monthly fee in exchange for 0.5-2% equity. Others charge full market rate ($10K-15K/month) with no equity. At ShipSixty, we work on a fee-plus-equity model, which aligns our incentives with yours. Just make sure you understand what you're agreeing to before you sign.

Good answer: Any clear, specific answer that explains the model and what they get. "I charge $8K/month plus 1% equity vesting over two years" is clear. "It depends on the engagement" without further detail is not.

Red flag answer: Bringing up equity for the first time after you've already started working together. That conversation should happen on the first call, not month three.

Question 10: Can I speak to a founder you've worked with in the last 6 months?

This is the closer. Every credible fractional CTO should be able to point you to at least one founder who'll take a 20-minute call and say good things about them. "I'd need to check if they're comfortable with that" is a yellow flag. Not being able to produce anyone is a red flag. Ask for a recent reference, not a curated one from three years ago.

Good answer: "Of course — let me introduce you to two founders I've worked with in the last year. I'll email them now and you can reach out directly."

Red flag answer: Stalling, excessive caveats, or offering a reference from 2022. Recency matters. Their best recent work is what you're hiring.

The Red Flags That Cost Founders Real Money

I've watched founders ignore warning signs in the hiring process and pay for it. Here's what I see most often — and what it ends up costing.

Red Flag #1: They can't name a specific deliverable for month one. If you ask "what will I have at the end of our first 30 days together?" and they say "it depends on where you are," that's a problem. A good fractional CTO can tell you exactly: a tech stack decision, a product scope document, a developer shortlist, a hiring plan. If they can't name it, you'll end up paying $10K-15K for a month of meetings and a vague strategy deck.

Red Flag #2: They talk about their background more than your problems. I've heard founders describe first calls where the fractional CTO spent 45 minutes talking about their own experience and only five minutes asking about the startup. That's a consulting mindset, not an operator mindset. Your fractional CTO should be curious about your business, your users, your constraints. If they're still pitching at the end of call one, they're not listening.

Red Flag #3: They can't explain their approach to a non-technical founder. This is a dealbreaker for me. If you don't have a technical background and your fractional CTO can't explain what they're doing in plain language, you've lost oversight of your own product. I've seen this cost founders $30K+ in misdirected builds because they couldn't follow what was happening and didn't feel comfortable asking. Your fractional CTO's job includes making the technical accessible to you. If they can't, find someone who can.

What a Great Fractional CTO Actually Sounds Like

Here's what I want you to walk away from a first call feeling: like you just talked to someone who genuinely understands your situation and has clear ideas about how to help. Not someone who impressed you with jargon. Not someone who sold you on their resume. Someone who asked good questions, gave you specific answers, and made the technical feel manageable.

A great fractional CTO candidate will:

• Tell you what stage they're best at — and be honest if you're not quite their fit
• Give you a clear picture of what month one looks like, with actual deliverables
• Show you recent examples, not just credentials
• Talk about your business more than their background
• Explain technical concepts in terms you understand — without being condescending
• Be transparent about pricing, equity, and availability before you have to ask
• Offer references without hesitation

And they'll be comfortable saying "I don't know, but here's how I'd find out" — because that's what good technical leadership actually looks like. Not omniscience. Rigour.

One More Thing Before You Sign

Don't let a great first impression shortcut your due diligence. The founder I mentioned at the start of this article — the one who lost $36K and three months — told me the fractional CTO was "incredibly impressive in the first meeting." He had a polished deck, strong references from years ago, and confident answers to every question.

She just didn't know which questions to ask.

Now you do. Take this list into your next conversation. Ask for specifics every time you get a general answer. And trust your gut when something feels evasive — it usually is.

If you want to compare notes on what you're hearing, or you're open to seeing what ShipSixty would look like for your stage, come have a conversation. I'll tell you the truth about whether we're the right fit or not. That's what the first call is for.

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About ShipSixty: I'm a fractional CTO working with Australian startups from pre-seed to Series A. I help non-technical founders build MVPs, hire technical teams, and make smart technology decisions. Based in Sydney, working with teams across Australia and remote. Learn more about how we work →