Going Deeper: 7 Questions for CIOs
Those Who Run Technology Aren't Always Those Who Decide About It


Joseph Teperman | Paulo Aziz Nader | Amrop Brazil
We have spent more than 50 years, combined, working with technology companies. We started inside them, early in our careers. Then we moved to the other side of the table – as consultants, headhunters, mentors, and advisors.
Even after all that time, one thing still stands out: most interviews for technology leadership roles remain shallow.
Looking beyond the surface
Most of these interviews are shallow, in the most dangerous sense. Full of jargon, buzzwords, and rehearsed answers. Solutions that look great on a slide, then break the moment they meet real operations, real culture, and the real world.
Here's the paradox: technology itself has become a commodity. Tools can be bought. Platforms can be licensed. A stack can be assembled in weeks. None of that has ever been easier.
What doesn't come in the package is something else entirely – architectural clarity, execution discipline, and a practical view of the future. No CIO or CTO comes with those guaranteed. They never did.
That's probably why the same question keeps surfacing in boardrooms: do we have someone who simply runs technology, or someone who carries the company's strategy, operations, and digital future forward?
Much of the problem starts before the hire is even made. Few people know how to properly interview a technology leader. In practice, many don't even know where to begin evaluating whether they're in front of the right person.
Failing to define, up front, the skills, behaviors, experiences, and competencies that actually matter for the company's specific context – something that sounds obvious – tends to produce bad decisions. Especially in a world saturated with hype, buzzwords, and well-rehearsed answers.
Real maturity tends to show up somewhere else entirely: in hard choices, in trade-offs, in the ability to think before configuring anything.
We're no longer looking for someone who knows what to install. We're looking for someone who knows how to decide.
A good CIO doesn't just deliver systems that work. They make the rest of the company think more simply, operate more intelligently, and decide faster. At the core, they're the guardian of digital coherence — the link between what strategy aims for, what operations can support, and what technology can actually carry.
Digital transformation isn't written in PowerPoint. It shows up in daily life – in how people work, integrate, automate, prioritize, and learn. The invisible architecture (processes, teams, integrations, governance) usually says far more about a CIO than any polished innovation case study.
That experience led us to a set of questions that changes the tone of the conversation entirely. These aren't questions designed to test technical repertoire or listen for well-pronounced buzzwords. They're designed to reveal judgment, maturity, and a way of thinking.
The 7 Questions
1. What technology did you choose not to adopt — and why?
2. When did you manage to turn "digital transformation" into everyday behavior?
3. What kind of technical decision have you gotten wrong — even with good arguments at the time?
4. What held you back most when scaling a technology? What helped you most?
5. Which initiative you led had the greatest business impact? Why?
6. What was the most complex incident you had to resolve — and how did you structure your team to handle it?
7. When is it time to rebuild — not just patch?
Looking beyond the surface
These questions aren't meant to catch anyone in a contradiction. They're meant to cut through the noise, expose the essence, and measure real maturity — to understand whether we're in front of someone who leads through reflection, or through whatever's trending.
You don't need to use all seven. Sometimes one or two are enough to completely change the quality of the conversation. Use them as a starting point. Adapt them. Build your own.
And don't skip competency-based interviewing. It won't solve everything, but it helps more than most people expect.
In the end, the idea is simple: go beyond the what, and get to the who.