Doug’s Friday Feature: Teach Curiosity, Not Certainty, for AI Readiness

To our community of data leaders and learners,

Everywhere I look, leaders are wrestling with the same question: how do we keep up with the pace of AI? New tools appear daily, promising faster insights and endless efficiency. But beneath the excitement is a quieter challenge, the need to help people stay curious in the face of change, because curiosity is now a core driver of true AI readiness.

Curiosity is now one of the most valuable traits in any organization. It’s what allows us to adapt when technology evolves faster than our playbooks. It’s what keeps teams learning and building instead of fearing what comes next. The companies that will thrive aren’t chasing every new model or tool. They’re creating a culture where curiosity is a habit, not an accident.

We often talk about “future-proofing” skills, but no one can predict what jobs will exist three years from now. The only way to prepare people for the unknown is to help them develop the mindset to explore it. As I said in a recent conversation, leaders need to teach their people how to be curious, because their people may actually invent the next role or process that transforms the business.

Across industries, we’re already seeing this happen. In finance, analysts are moving beyond spreadsheets into predictive modeling. In marketing, creatives are blending storytelling with AI-generated insight. In healthcare, clinicians are using data tools to identify new treatment paths. Every one of those shifts began because someone asked a better question.

Curiosity doesn’t flourish on its own. It needs structure, time, and leaders who give people permission to explore without fear of being wrong. When executives model that behavior by admitting they don’t have all the answers or asking “why” before “how,” they send a powerful signal that learning is part of the work, not something extra.

Too often, organizations treat upskilling as a line item or one-time training. Real readiness takes more than resources; it takes mindset. It means creating a culture where continuous learning feels normal, where experimentation is rewarded, and where growth is expected. That kind of culture doesn’t come from technology. It comes from leadership.

I think a lot about how we measure success in this environment. Titles and org charts still matter, but I believe we’re moving toward what I call a “competency ladder” instead of a title ladder. The question isn’t, “What’s your position?” It’s, “What have you mastered, and how are you using it to create value?” When people are measured on curiosity, adaptability, and the ability to connect ideas across disciplines, organizations get smarter, not just faster.

The irony of this AI moment is that the more advanced our systems become, the more important our human skills will be. Communication, critical thinking, and empathy aren’t “soft” skills, they’re survival skills. AI can generate language, but it can’t generate understanding. It can analyze data, but it can’t decide what matters. We’ve taught computers to think, but we haven’t taught them to care, and that’s still our job.

That’s why I tell students and early-career professionals that if you’re studying AI or data science, spend as much time learning to write, to question, and to listen. The tools will handle the calculations. What they can’t handle is meaning. And meaning is what moves organizations forward.

At Data Society, The Data Lodge, and CDO Magazine, we see this dynamic every day. The most successful organizations aren’t just the ones deploying AI. They’re aligning leadership, literacy, and learning to build shared understanding. They’re turning data fluency into a common language that connects teams, creating space for experimentation, and letting curiosity lead to innovation.

As we head into 2026, this will define leadership maturity, not how quickly you can adopt technology, but how effectively you help your people adapt alongside it. Progress will come from those who balance clarity with openness, who can say, “Here’s where we’re going,” while asking, “What might we be missing?”

As you plan your next chapter, remember this: the best thing you can teach isn’t certainty, it’s curiosity. Certainty closes doors. Curiosity opens them. Certainty leads to compliance. Curiosity leads to discovery.

The future belongs to those who keep asking questions.

Teach curiosity, not certainty.
Doug Llewellyn 

Check out our previous Friday Feature: The Power of Real Conversation in an AI World