7 questions your CTO hopes you will never ask (but you should)
Value Creation Plan Newsletter #111
Most investors and board members nod along when “digital transformation” or “agentic AI” gets presented by the CTO, but few dig deeper. The result? Millions spent on projects that look great in slides but flop in practice.
Board members don’t need to become CTOs, but they do need to ask sharper questions that cut through the noise and reveal whether a strategy will actually create value or just fund another expensive R&D project.
When a Board nods silently to a Technology presentation or gets lost in the buzzwords flying they are not doing their jobs properly. We can all do better.
It is better to be the Board Director who risks looking foolish by asking one “stupid question” to the CTO than the one who pays for a very expensive answer.
Based on past experience from being in the CTO seat, here are 7 questions every board member should be asking about a technology strategy, but often don’t:
1. What problem are we really solving?
What is the critical problem the CTO is trying to crack, and how do we all know whether these are actually the right problems to solve?
A good strategy starts with an impact metric that truly matters. Are you solving for something critical like revenue, margins, customer retention… or tinkering on side projects that just look good on paper and are fun to do R&D on?
2. What is your definition of done?
Perfection is expensive, and so is failure. What level of error or downtime is tolerable for this project? At what point does the error rate force a rethink of the approach? Too often, goalposts shift mid-project. Boards should insist on honesty and commitment on a definition of done upfront so they don’t get played later.
3. Who are you building this for… and are they onboard?
If the technology strategy is designed for generic “users” or “clients” who don’t exist in the real world, you’re setting yourself up for a big expensive headache.
Instead, insist on having a key sponsor outside the Technology team accountable for the impact metric who will be involved in discovery, testing, and rollout. The hero of the story should not be the CTO.
4. What are the buy vs. build vs. borrow trade-offs?
Every architecture choice (off-the-shelf SaaS, tightly integrated systems, or bespoke build) has implications for cost, risk, and future flexibility. Don’t just ask what is being built, but why this route was chosen.
5. What’s experimental vs. proven?
Boards should be allergic to brochureware. Ask for first-hand references, not consultant case studies. For traditional tech, demand evidence of previous rollouts at similar companies and lessons learned. For AI, push for transparency on training data, testing, and safeguards.
6. What happens if we’re very wrong—or very right?
Too often, boards only hear the promise of the upside. But reputational risks, customer backlash, or unexpected scaling challenges need equal weight. The best boards foster a safe space where companies can experiment responsibly while holding technology projects to tougher scrutiny around data usage, cybersecurity and worst-case scenarios.
7. What is the fully costed version of this?
Technology isn’t just software licenses and cloud credits. Make sure the true cost includes all the plumbing, the talent, the vendors and the ongoing maintenance costs. Ask for the “all-in” number upfront—better a realistic figure today than a series of budget surprises tomorrow.
Why this matters now
In today’s private equity environment (where exits are delayed but every portfolio company needs to be exit ready) technology is no longer a “support function.” It’s a lever of value creation, margin protection, and differentiation.
But only if boards ask the right questions. Otherwise, you risk funding mediocre ideas or falling for the hype cycle to play catch up.
So, next time a CTO discussion comes up at the board table, don’t nod politely and do ask these difficult questions.
The uncomfortable questions are the ones worth asking,
Juan