Bytes of Experience : CIOs Unplugged

In this episode of Bytes of Experience, Bo and Dana sit down with Dr. Jeff Gardiner, a cybersecurity leader whose recent doctoral research tackles one of the most persistent mysteries in the field: why do well‑funded, well‑staffed, highly trained cybersecurity teams still experience breaches that seem preventable? Drawing on analyses of major incidents like Target, Equifax, and Change Healthcare, Jeff argues that the problem isn’t people or tools — it’s structural. Cybersecurity professionals routinely use the language of risk, but aren’t actually taught risk management, and leaders assume those skills exist without verifying them.

Jeff walks us through his  dissertation, including natural language processing of the NIST NICE framework, competency comparisons between cybersecurity and non‑cyber professionals, and interviews with CISOs and senior leaders. His findings reveal “epistemic compression,” where four distinct risk skills collapse into a single undifferentiated sense of “knowing risk,” leaving teams confident but not equipped to prioritize, quantify, or communicate risk effectively.

We explore what CIOs and aspiring leaders should do differently, why CISOs may belong in enterprise risk rather than IT, and how organizations can rebuild risk reasoning from the ground up. Jeff also previews his new book,  A Knowledge Theory of Capital: The Value of Natural and Artificial Intelligence, Volume 1  which reframes knowledge — human and artificial — as a form of capital that organizations must invest in and protect.

This is one of the clearest, most accessible explanations of why cybersecurity decision‑making breaks down, and what leaders can do on Monday morning to fix it.

 

Book Recomendation:

How to Measure Anything in Cybersecurity Risk  by Hubbard and Seiersen

In this episode, Bo and Dana talk with Jill Kowalchuk, Director of Research Computing and Investment Office, University of Calgary, about the evolving intersection of technology, research, and people. Jill shares insights from her work with WestGrid, Compute Canada, CanSOC, and CIRA, exploring how collaboration and leadership shape national research infrastructure. She discusses the challenges of bridging IT and research, scaling operations, managing risk, and balancing institutional priorities — from cybersecurity frameworks like NIST 800‑171 to the realities of funding and resource constraints. It’s a candid look at how Canadian universities are redefining research support, security, and trust across campus.

 

Book Reccomendations:

 Radical Candor by Kim Scott

This Is How They Tell Me The World Ends by Nicole Perlroth

 

 

 

Season two of Bytes of Experience kicks off with a quick preview of what’s ahead. After a summer pause, Bo and Dana return energized and ready to dive into another year of honest, thoughtful conversations about leadership, technology, governance, and the realities facing higher education today.

They reflect on the start of the academic year — and talk about the themes shaping their thinking as they plan season two. From the financial pressures facing institutions, to the messy human side of leadership, to the accelerating impact of AI on campuses, to cybersecurity and the emerging conversation around sovereign cloud, they outline the topics they’re eager to explore with guests who are living these challenges firsthand.

This short intro sets the stage for a season focused on real stories, real constraints, and real leadership — the kind that happens when things aren’t simple. As Dana puts it, they’re ready to talk about “the messy parts… the human parts” of leadership and shine a light on what’s actually happening behind the scenes.

Season two is coming soon — with new tools, new guests, and the same unfiltered insights you’ve come to expect.

Season 1 of Bytes of Experience began as a simple idea: two retired CIOs talking shop over coffee. But after more than thirty conversations with leaders across higher ed, government, healthcare, and industry, Bo and Dana discovered something unexpected — the real story was never about technology. It was about people.

In this Season 1 wrap‑up, Bo and Dana look back on the themes that surfaced again and again: trust before tools, influence without authority, the messy reality of governance, the human side of crisis leadership, and why security is ultimately a cultural challenge, not a software problem. They revisit the moments that surprised them, the lessons that stuck, and the insights that kept showing up no matter who they were talking to.

Most of all, they reflect on the generosity of their guests — leaders who showed up with honesty, vulnerability, humour, and a willingness to talk about the parts of leadership that never make it into conference keynotes. Season 1 taught them more than they expected, and they had far more fun than they ever imagined.

As they close out the season, Bo and Dana share their gratitude, their reflections, and a glimpse of what’s coming next. Season 2 is already taking shape — with new guests, new stories, and more candid conversations about the real work of IT leadership.

Stepping into the CIO role is one of the most complex leadership transitions in any organization — and yet most new CIOs receive little structured support. In this episode, Bo and Dana sit down with Deloitte’s Mark DiNello and Manj Kanwal to explore the CIO Transition Lab, a program designed to help new technology executives map out their first 180 days and beyond.

Drawing on years of experience working with CIOs across higher ed, government, healthcare, and industry, Mark and Manj unpack why the early months matter so much, why CIO transitions are uniquely challenging, and how leaders can balance listening, credibility‑building, and the urgent need to deliver results. They discuss the “four faces of the CIO,” the importance of assessing inherited teams, and the tension between keeping the lights on and driving transformation.

From navigating unknown unknowns to building critical relationships with CFOs, CHROs, and registrars, this conversation offers practical insights for anyone stepping into — or supporting — senior technology leadership.

Whether you’re a new CIO, an aspiring leader, or simply curious about what the first six months really look like, this episode delivers candid stories, useful frameworks, and hard‑earned lessons from the front lines of executive transition.

Reading recommendations

Deloitte Top Tech Trends 2026

Deloitte 2026 Global Human Capital Trends

In this episode of Bytes of Experience, Bo and Dana sit down with Axel Schulz, Director of Cybersecurity Operations at CANARIE, to explore how shared cybersecurity services are evolving across Canada’s research and education network. Axel traces his unconventional path from philosophy to SOC leadership, reflects on what makes cybersecurity in higher ed uniquely challenging, and explains why collaboration—not centralization—is the sector’s real superpower.

The conversation digs into five strategic pillars, including national cybersecurity assessments, threat intelligence, the federated SOC, resource‑sharing initiatives, and community engagement. Axel highlights the rapid growth in sector‑wide participation, the cultural shift toward open incident sharing, and how higher ed institutions are building collective resilience in the face of rising threats and AI‑driven complexity.

Book References: 

Chip War - The Fight for the World's Most Critical Technology by Chris Miller

Fish In a Tree by Lynda Mullaly Hunt

Invisible Women - Data Bias in a World Designed for Men by Caroline Criado Perez

 

A grounded, optimistic look at how Canada’s research and education community is strengthening cybersecurity—together.

In this episode of Bytes of Experience, Bo and Dana sit down with Darren Schell,  Associate VP Information Technology (a.k.a. CIO) at the University of Lethbridge and a graduate of the CUCCIO Leadership Development Program (LDP). Darren brings a grounded, practical perspective shaped by 24 years at a midsize university — from his early days in the Registrar’s Office to becoming Associate VP Information Technology.

We explore Darren’s leadership journey, what drew him to the LDP, and the lessons that reshaped how he leads. Darren reflects on the realities of influence in higher ed, the power of storytelling, the challenge of simplifying complexity, and the importance of understanding how people actually use technology — not how IT assumes they do.

He also shares candid insights about collegial governance, ERP modernization, and the unique leadership demands of smaller institutions.

Book Recommendation:

Turn the Ship Around: A True Story of Turning Followers into Leaders by David Marquet 

 

In this episode of Bytes of Experience, Bo and Dana sit down with one of Ontario’s most respected registrars: Ray Darling, University Registrar at the University of Windsor. Ray’s path is anything but typical — from varsity basketball point guard to leading registrarial teams at four universities. His story offers a rare, panoramic view of how the academic enterprise really works.

Together, we explore the Registrar–CIO partnership: why it matters, how it succeeds, and what happens when alignment breaks down. Ray shares candid insights on data stewardship, the realities of registration stress, cloud SIS transitions, and the art of building trust between business and IT teams.

We also dig into the future of registrarial work — from AI to student‑centred design — and reflect on the leadership lessons Ray has carried across institutions.

Topics include: • What a modern Registrar actually does — and why it matters • The Registrar–CIO relationship as a shared product partnership • Data ownership vs. data stewardship in higher ed • Registration stress, cloud SIS risks, and operational resilience • How to co‑design with faculty, not just support them • Building collaborative business–IT cultures • The next five years in registrarial work • Ray’s leadership lessons from four institutions