How to Hire a Technology Expert

1.What have you personally built or shipped in the past two years, and how is that relevant to what we're trying to do?

Why it matters: Technology evolves at a pace that makes experience from five years ago partially obsolete in many domains. Recent hands-on experience is the best evidence that an advisor's knowledge of the current technology landscape is current — not based on what the stack looked like in 2020. This question distinguishes advisors who are current practitioners from those who transitioned primarily to advisory roles based on older experience.

2.Have you worked with companies at our stage and with a similar technical challenge — and what decisions do you wish you'd made differently?

Why it matters: Stage-relevant experience is as important as technical depth. The decisions that matter at MVP stage — speed to ship, avoiding over-engineering, choosing flexible primitives — are different from those that matter at scale. An advisor who has navigated your specific stage has made the relevant mistakes already and can help you avoid them. Asking what they wish they'd done differently surfaces intellectual honesty and the kind of pattern recognition that only comes from living through the consequences of decisions.

3.Looking at our current architecture and approach, what would you change and what would you leave alone?

Why it matters: This question tests whether the advisor can deliver independent technical judgment rather than validation. Strong technology advisors will identify specific things they would approach differently — database choices, service boundaries, infrastructure setup, testing coverage, deployment practices — and explain why. Advisors who find nothing to change either have limited exposure to your specific context or are defaulting to agreement to preserve the relationship.

4.How do you think about the build-versus-buy decision, and can you give me an example of a time you talked a client out of building something custom?

Why it matters: Build-versus-buy is one of the most consequential recurring decisions in technology, and the right answer depends on a combination of factors — team capacity, maintenance burden, vendor risk, core differentiator potential, and total cost of ownership. Advisors who have a clear, nuanced framework for this decision and can point to a specific case where they recommended against building are demonstrating both intellectual rigor and the willingness to challenge the instinct to build everything in-house.

5.What do you see as the most significant technical risks in our current situation, and what would you prioritize addressing first?

Why it matters: Risk identification is where a strong technology advisor creates some of their most immediate value. An advisor who can quickly identify the most significant technical vulnerabilities — security exposure, scaling bottlenecks, single points of failure, compliance gaps, dependency risks — and prioritize them by business impact is doing exactly what a good CTO would do. The quality and specificity of their risk assessment is a direct signal of the depth and currency of their technical judgment.

6.How do you communicate technical decisions and their business implications to non-technical co-founders, boards, or investors?

Why it matters: Many technical advisors are excellent engineers but poor communicators to non-technical stakeholders. For a fractional CTO or technical advisor working alongside a non-technical leadership team, the ability to translate technical decisions into business consequences — cost, timeline, risk, opportunity cost — is a core part of the value they provide. Asking for a concrete example of how they've done this in a past engagement reveals whether they have this capability at a high level.

7.What do you see as the most important technical decisions we'll need to make in the next six to twelve months?

Why it matters: Strategic technical foresight — anticipating the decisions that will matter before they become urgent — is one of the highest-value things a CTO brings. Advisors who can articulate a clear view of the decisions on your horizon, why they'll matter, and how to think about them before they're forced reveal both their understanding of your situation and the quality of their strategic technical thinking. Advisors who can't answer this question at a reasonable level of specificity may not have the strategic depth the role requires.

8.What does the engagement look like in practice — how involved will you be, and what does a productive working relationship with you require from our team?

Why it matters: Many fractional technical engagements underdeliver because the expectations on both sides were poorly defined at the start. Understanding specifically how involved the advisor will be — hours per week, types of decisions they'll weigh in on, their response time for urgent questions, what they need from your team to do their best work — sets the foundation for a productive engagement. Misaligned expectations about availability and scope are the most common source of dissatisfaction in fractional technical relationships.