Jay Kiew challenges leaders to build futures rooted in curiosity, not certainty
Jay Kiew didn’t plan to build a life around navigating disruption. But disruption found him anyway.
As a baby in Singapore, his aunt was snapping photos on a film camera when she noticed a strange red dot appearing in his eye in every image. It sparked a question, and it wasn’t long before doctors discovered cancer in his left eye. Fourteen tumours later, the eye was removed and replaced with a prosthetic.
That diagnosis could have defined him. Instead, it became his first lesson in adapting.
“My parents were radio DJs,” he says. “We moved a lot — eight times before I was 12. At that point, I was like, ‘This is normal.’ I had loved change so much that I became used to it. I decided to make a career out of it.”
That career has taken shape in many ways, including being a keynote speaker, transformation advisor, leadership strategist, and CEO of Citizencentric.
Kiew spends up to 40 weeks a year on the road speaking at conferences, including the CIO Peer Forum this week. The Peer Forum is an annual national gathering of the CIO Association of Canada, where IT leaders from across the country meet to discuss strategy, share lessons, and connect on the evolving role of technology in business.
The rest of his time is spent helping organizations (from public agencies to private firms) get comfortable with change, especially as artificial intelligence starts reshaping work.
When technology isn’t the real problem
Kiew says it’s important to lead with people ahead of tech.
“We don’t have a technology problem. We have a people opportunity,” he told Digital Journal. “The latest technology is at our fingertips at a fraction of what it would have cost a year ago — and that’s really exciting.”
But excitement alone doesn’t drive transformation.
In his work with organizations, Kiew sees the same barriers showing up again and again. He calls them the five chains of change: clutter and chaos, comfort with the status quo, competing interests, constraints like time or budget, and apathy.
They’re the things that slow teams down, stretch them thin, or stop momentum before it starts. And most of them have nothing to do with the technology itself.
The real challenge, in Kiew’s view, is whether people are actually able (or even willing) to use them well. Technology can scale, automate, and accelerate, sure.
What it can’t do is align teams, cut through internal noise, or fix a broken culture.
These chains aren’t abstract, either. They show up in meetings, roadmaps, and the decisions people make every day. And according to Kiew, they’re a big reason why digital transformation efforts stall out.
What real innovation looks like
For Kiew, innovation begins with your mindset.
And in a moment when CIOs are being asked to lead through near-constant disruption (while juggling limited resources, shifting priorities, and rising expectations), he believes that how leaders show up matters more than ever.
In his upcoming book, Change Fluency, Kiew lays out nine principles for leading through uncertainty. Built around curiosity, experimentation, and actually getting things done, three of the ideas he comes back to often are zoom out to zoom in, leverage your limits, and work in wonder.
The first — zoom out to zoom in — asks leaders to resist the urge to rush into problem-solving mode. Instead of going straight to the most obvious answer, Kiew wants leaders to widen their view and consider possibilities beyond their immediate environment.
“Oftentimes we defer to our own critical thinking and jump straight to the solution,” he says. “Zooming out to zoom in requires that you navigate the noise to get to the signal.”
The second idea, leverage your limits, calls for a shift in how organizations think about constraints. Most CIOs are no strangers to being asked to do more with less. But Kiew frames that not as a hindrance, but as a creative advantage.
“Every organization has limits — time, people, money, resources,” he says. “The differentiator is how well they’re able to leverage those limits, because we all have them.”
Finally, work in wonder is an invitation to shift from predictability to possibility. Our day-to-day worlds are obsessed with certainty, dashboards, and forecasts, but Kiew argues that curiosity might be the most valuable leadership trait of all.
“Design for the best, then disrupt with better,” he says. “The need for working in wonder is actually shifting from working in certainty to working in curiosity.”
Rather than building innovation around control, these ideas ask CIOs to lean into complexity, stay open to learning, and reimagine how their teams adapt to change.
At the 2025 CIOCAN Peer Forum, Kiew delivered the closing keynote on May 29, where he expanded on these principles by challenging CIOs to rethink how they approach decision-making in fast-changing environments.
“Zooming out to zoom in requires that you navigate the noise to get to the signal,” he said.
Whether addressing constraints or designing new strategies, he encouraged the audience to treat curiosity as a core leadership skill and that the ability to innovate starts with asking better questions.
“The need for working in wonder is actually shifting from working in certainty to working in curiosity,” he told the room.
The human side of transformation
Kiew’s approach to transformation puts experimentation in the hands of the people doing the work.
With many of his clients, he organizes monthly community of practice calls where different departments take turns sharing how they’re using AI. Some teams present small wins. Others talk openly about their discomfort or uncertainty. What matters is that the learning is shared across the organization, and the teams, not outside consultants, are the ones leading the conversation.
“Some are sharing how uncomfortable they are,” he says. “But what they did despite the discomfort.”
And that’s the point, isn’t it? Change might feel like a directive, but it’s actually an invitation.
Kiew says this human-centred approach didn’t fully click until he led strategy at Telus Health.
While leading strategy and transformation, he was responsible for a portfolio of about 40 digital health products. On paper, some of the tools checked all the right boxes. But in practice, they didn’t land.
“The ones that had the biggest usage were the ones where we were doing ethnographic research,” he says. “We were sitting down with people who were using the apps and watching what they were doing.”
What worked wasn’t a better interface or more features. It was empathy.
The teams that spent time with users — watching how they actually navigated the tools — were the ones who built something useful.
He says it taught him something that’s stayed with him ever since: don’t design for users, design with them. That philosophy runs through all his work, and it’s at the heart of his message for CIOs.
Why this moment matters
As the pace of change accelerates, Kiew suggests that leaders stop obsessing over predictions. What matters isn’t what’s coming in 2030. What matters is what we do right now.
“It’s less about predicting the future. I think it’s more about, ‘How do we propel the present?’” he says. “To build the future, we have to deeply understand what’s going on today.”
For young or emerging CIOs, his advice is to stop waiting for permission and start leading by example.
“Ignore most hierarchies,” he says. “I don’t care what your title is. What I trust are the leaders who are able to provide insights that are most contextual and relevant — now, in the moment.”
By focusing on the now, he says it’s not about being certain, but being willing to explore.
That mindset was shaped long before he wrote a book or led a strategy team. It goes back to the boy with the prosthetic eye and the long list of past addresses, who was waiting for the next adventure.
“Discomfort begets comfort with the uncomfortable,” he says. “And every time I’ve taken a risk, it’s just been sort of friggin’ sweet.”
Digital Journal is the official media partner of the CIO Association of Canada.
