You've decided a fractional CTO is what your business needs: C-suite level technology leadership without the $200K+ salary. But how do you find the right one and make sure they're actually good?

Many fractional CTOs are consultants who parachute in, give you a 50-page report, and disappear. Others are former CTOs who don't have real-world implementation experience. A few are excellent—they understand your business, help you think strategically, and actually solve problems.

The difference comes down to asking the right questions before you hire.

Here are the 10 questions that separate great fractional CTOs from the rest.

Question 1: "Tell Me About Three Clients You've Worked With—What Was the Business Outcome?"

Why this matters: You want to understand their track record, not just their credentials.

What to listen for:

  • Specific, measurable results (revenue growth, cost savings, efficiency gains)
  • Understanding of the business, not just the technology
  • Names, situations, and outcomes they can describe in detail

Red flags:

  • Vague answers ("They were happy")
  • Only technical descriptions (what systems they built, not what it meant for the business)
  • Can't name any clients or reference them
  • Stories that don't feel real

Good answer: "I worked with a construction company doing $15M annual revenue. Their problem was that project managers couldn't see real-time jobsite status. We built a data dashboard pulling from their existing systems—no new software needed. This reduced admin overhead by 8 hours/week and helped them identify operational inefficiencies. They ended up improving project margins by 2% annually, which added $300K to the bottom line."

This tells you: they understand the business problem, they deliver measurable value, and they focus on outcomes.

Question 2: "What's Your Philosophy on Technology Decisions?"

Why this matters: This reveals whether they'll recommend technology for the right reasons (business value) or wrong reasons (trendy, cool, or commission).

What to listen for:

  • Emphasis on business goals before technology
  • Pragmatism (use best tools, not bleeding-edge)
  • Restraint (willing to use existing systems if they work)
  • Evidence-based decisions

Red flags:

  • Pushing specific technologies hard without understanding your business
  • Enthusiasm for shiny, new tech
  • Dismissing your existing systems without evaluation
  • More excited about the technology than the business outcome

Good answer: "I start with understanding your business problem and constraints—budget, timeline, team skills, integration needs. Then I recommend the best tool for that specific situation. Sometimes that's enterprise software, sometimes it's a scrappy solution that solves the problem 80% as well for 20% of the cost. I'm not attached to any particular technology; I'm attached to solving your problem well."

This tells you: they prioritize business value, they're pragmatic, and they're not selling you on tools.

Question 3: "What's an Example Where You Recommended AGAINST Spending Money?"

Why this matters: A good fractional CTO prevents waste. They should be as proud of money saved as money invested.

What to listen for:

  • Specific example of recommending restraint
  • Client listened (they have credibility to push back)
  • Good business reason for the recommendation

Red flags:

  • Can't give an example
  • Sounds like they recommend everything they suggest
  • Weak reasons for the recommendation

Good answer: "A client wanted to implement a $50K ERP system. Before I said yes, I asked: what problem are you solving? What will you measure to know if it works? Turned out their real problem was poor data visibility in one department, not a company-wide system issue. We spent $3K on a reporting tool that solved it in 30 days. They were planning to spend $50K on implementation, change management, and training. We saved them $47K and they got results faster."

This tells you: they think like a CFO, not a vendor.

Question 4: "How Do You Stay Current with Technology?"

Why this matters: Technology changes constantly. You need someone who's learning continuously, not resting on old credentials.

What to listen for:

  • Specific way they learn (conferences, certifications, side projects, reading)
  • How they balance learning with delivery
  • Examples of recent learning applied to client work

Red flags:

  • Vague answer ("I read blogs")
  • Defensive tone (imply they already know everything)
  • Last certification was 5+ years ago

Good answer: "I invest 5-10 hours per week in learning. I follow industry blogs and newsletters, take online courses in areas relevant to my clients, and I work on small projects outside my consulting to stay hands-on. Last quarter I studied AI/ML because several clients are asking about it. I'm not building AI systems, but I understand the landscape well enough to advise if it makes sense for their business."

This tells you: they're intellectually curious and invest in staying sharp.

Question 5: "How Do You Measure Your Own Success?"

Why this matters: This reveals whether they care about business outcomes or just deliverables.

What to listen for:

  • Metrics tied to business impact (revenue, efficiency, risk reduction)
  • Long-term thinking (not just completing projects)
  • Client satisfaction and outcomes

Red flags:

  • Measuring hours worked or features delivered
  • Doesn't mention client outcomes
  • Only process-oriented metrics

Good answer: "I measure success by whether my recommendations actually improve the business. Did we reduce costs? Improve efficiency? Increase revenue? Reduce security risk? I check in quarterly with clients on actual outcomes—not just did we implement something, but did it deliver the business value we expected? If it didn't, we adjust. I'm not successful until the client is seeing results."

This tells you: they're accountable for actual outcomes.

Question 6: "Tell Me About a Time You Disagreed with a Client's Technology Decision. What Happened?"

Why this matters: You need someone who'll push back when necessary, not just agree with whatever you say.

What to listen for:

  • Specific situation where they had a different perspective
  • How they handled the disagreement (diplomatically, with data)
  • Client listened and/or learned something

Red flags:

  • Never disagrees with clients
  • Sounds like they were dismissive of the client's perspective
  • Didn't present data to support their view
  • Got overruled and bitter about it

Good answer: "A client was considering moving to a hosted cloud environment they thought was more secure than their on-premise servers. I agreed more security was the goal, but recommended we upgrade their on-premise security instead because they had specialized software that didn't work well in the cloud. The switch would've cost $60K and caused two months of disruption. Better security via upgrades cost $10K. I presented a security analysis showing why both approaches could work, but the on-premise approach better for them. They listened, we did the upgrade, and they're better off."

This tells you: they think independently, present data to support their view, and prioritize the client's best interest.

Question 7: "What Kind of Clients and Situations Are You Best For?"

Why this matters: You want to know if they're a good fit for your business, and if they're honest about their limitations.

What to listen for:

  • Clear understanding of their sweet spot
  • Honest about what they're not good at
  • Questions about your business to assess fit

Red flags:

  • Claims to be perfect for every situation
  • Can't articulate where they add the most value
  • Doesn't ask questions about your specific situation

Good answer: "I'm best for 20-150 person companies with $5M-$100M revenue that are growing and realizing technology is crucial but don't have internal expertise. I'm good at strategy, vendor management, helping you think through major decisions, and bridging the gap between business and technology. I'm not good for companies that need deep implementation work (systems administration, coding) or that already have strong in-house tech teams. I'm also not the right fit if you need a hands-on person who can drop everything to fight fires."

This tells you: they're self-aware and honest about fit.

Question 8: "How Many Clients Do You Usually Work With, and How Many Hours Per Week?"

Why this matters: You need to know if they have actual availability and aren't overextended.

What to listen for:

  • Usually 5-8 clients max (more is too many)
  • 10-30 hours per week per client (15 is typical)
  • Structured schedule you can rely on

Red flags:

  • 15+ clients (they're spread too thin)
  • No structured hours (you'll get sporadic attention)
  • "I fit you in as needed" (means you're not a priority)

Good answer: "I typically work with 5-6 clients simultaneously, 15-20 hours per week each. So I'm full, but not overextended. For each client, I reserve a specific day or two per week. That way you know when to expect me and we have continuity. I don't do drop-in fractional work; I commit to regular engagement so I understand your business and can be effective."

This tells you: they're deliberate about workload and committed to clients.

Question 9: "What's Your Onboarding Process?"

Why this matters: Good fractional CTOs have a structured way to understand your business before recommending anything.

What to listen for:

  • Several weeks of discovery before big recommendations
  • Specific process for auditing and understanding current state
  • Conversations with key stakeholders
  • Written assessment before recommendations

Red flags:

  • "I'll start making recommendations immediately"
  • No structured discovery process
  • Doesn't want to talk to your team

Good answer: "Month one is discovery. I'll meet with you, your leadership team, and key technical staff. We audit your current systems, understand your business goals for the next 2-3 years, and identify pain points. I review documentation and sometimes do external audits. By end of month one, I have a written assessment of where you are, risks I see, and recommendations for the quarter. We prioritize together, and then we execute on priorities."

This tells you: they're thorough and don't jump to conclusions.

Question 10: "How Do You Handle Conflicts of Interest?"

Why this matters: Some fractional CTOs get commissions from vendors, which biases their recommendations.

What to listen for:

  • Clear disclosure of any vendor relationships
  • Commitment that recommendations are unbiased
  • Willingness to use best-of-breed vendors even if not their usual partners

Red flags:

  • Evasive answer
  • Undisclosed vendor relationships
  • Always recommends the same vendors
  • Defensive about the question

Good answer: "I'm transparent about any vendor relationships. I don't take commissions—I charge a flat fee for my work. I also don't have a preferred vendor list that I always recommend. Each client's situation is different, so I recommend what's best for them, which might be different from what I recommended to another client. I want you to be confident my recommendations are unbiased."

This tells you: they're ethical and not incentivized to sell you specific tools.

Red Flags That Disqualify Someone

Don't hire if:

  • They can't articulate specific outcomes from past work
  • They push their own company's services/products
  • They claim to be expert in everything
  • They don't ask questions about your business
  • They've never worked in your industry (sometimes okay, but they should be humble about it)
  • They're inconsistent on availability
  • They won't sign a contract specifying their role and commitment

The Right Questions Reveal Everything

These 10 questions separate mediocre fractional CTOs from great ones. A great fractional CTO will:

  • Answer with specific examples and stories
  • Demonstrate business thinking, not just technical thinking
  • Show intellectual curiosity and humility
  • Understand your business situation before prescribing solutions
  • Have clear values about how they work

Don't just check boxes. Pay attention to how they answer. Do they seem like someone who'll understand your business and advocate for you? Or do they seem like someone who'll recommend stuff regardless of whether it helps?

The best fractional CTO is the one who makes you feel like you're thinking about technology differently—not because they're imposing their view, but because they're helping you see your business more clearly.

Ready to Find Your Fractional CTO?

Sandbar Systems provides fractional CTO services to growing businesses. We start with a deep discovery process, provide transparent recommendations, and commit to your success.

If you're interviewing fractional CTO candidates, or if you want to explore working with us, we're happy to talk.

Schedule Your Free Consultation

Call us: (804) 510-9224 Email: info@sandbarsys.com

Ask us these same 10 questions. We're confident in our answers.