What Leading at City Scale Taught Me About Executive Clarity

I spent the better part of a decade as the Chief Information Officer for the City of Edmonton — responsible for over 450 staff, a $70 million annual operating budget, and the technology infrastructure that kept a city of 854,000 people running around the clock.

People sometimes assume that a role like that is primarily a technology role. It is not. It is a leadership role that happens to involve technology. The distinction matters more than most people realize — and understanding it took me longer than I would like to admit.

The Scale Problem Is Not What You Think

When you are accountable for 12,000 city employees, hundreds of business applications, and a 24/7 operation that cannot go down, the instinct is to manage the complexity. To build systems, processes, and governance structures that give you visibility and control.

That instinct is not wrong. But it is incomplete.

The real challenge at that scale is not managing complexity. It is maintaining clarity about what actually matters — and having the courage to act on that clarity when the organization's inertia is pulling in a different direction.

At Edmonton, I inherited an IT branch that had drifted from its purpose. The technical capability was there. What was missing was a shared sense of direction, a culture that empowered people to do their best work, and a relationship with the rest of the organization built on genuine trust rather than transactional compliance.

Rebuilding that took time. It required a different kind of leadership than I had practiced before — less about having the right answers and more about creating the conditions for the right questions to surface.

What Political Environments Teach You About Influence

Working in municipal government is a masterclass in operating without formal authority.

As a CIO reporting to the General Manager Corporate Services, accountable to elected officials, and dependent on the cooperation of department heads who had their own mandates and their own pressures, I quickly learned that the traditional levers of executive influence — hierarchy, budget control, positional authority — were necessary but not sufficient.

What actually moved things was relationship. Not the transactional kind — not the relationship of someone who shows up when they need something. The kind built through consistent presence, genuine curiosity about other people's problems, and a demonstrated willingness to subordinate your own agenda to the larger organizational goal.

I spent my first months at Edmonton in conversations. Not presenting. Not proposing. Listening. Trying to understand what the city's department heads actually needed from technology — not what they said they needed, but what the underlying problem was that they were trying to solve.

That investment paid dividends for years. When I needed to make a difficult case to council, I had allies who understood what I was trying to do and why. When I needed to move quickly on something that cut across departmental boundaries, I had relationships that made that possible.

The lesson I took from that experience: influence at the executive level is almost entirely a function of the trust you have built before you need it.

The Moment I Understood Transformation

In 2010, Edmonton became the first city in Canada to hold an open data apps competition. We launched an open data strategy — the fourth city in the country to do so — and invited developers, citizens, and entrepreneurs to build on the city's data.

At the time, this was genuinely novel. There was no playbook. There were skeptics inside the organization who questioned whether it was appropriate to make city data publicly available, and skeptics outside who doubted whether anyone would care.

What I remember most about that period is not the initiative itself. It is what it required of me as a leader.

It required me to hold a clear vision of where we were going while remaining genuinely open to how we would get there. To make the case for something that had no precedent in our context, using evidence from other jurisdictions and a clear articulation of the underlying logic. To bring people along who were uncertain — not by overriding their concerns, but by taking those concerns seriously and addressing them directly.

And it required me to be comfortable with the discomfort of being early. Of doing something before the consensus had formed. Of accepting that some people would not come along, and that was acceptable.

That experience shaped my understanding of what transformation actually requires. It is not primarily a technical or operational challenge. It is a human one. The question is never whether the technology works. The question is whether the people who need to change their behaviour are willing to do so — and whether you have done the work to earn that willingness.

What Consulting Taught Me That the C-Suite Did Not

After leaving Edmonton, I spent nearly a decade as a consultant — working with organizations ranging from CIBC and TMX Group to regional municipalities and technology startups.

The shift from operator to advisor was disorienting at first. As a CIO, I had authority. As a consultant, I had only perspective and the ability to ask good questions.

What I discovered was that the constraint was also a gift.

Without the ability to simply decide, I had to become much more precise about what I was actually trying to help a client see. I had to develop the discipline of separating what I observed from what I concluded, and what I concluded from what I recommended. I had to learn to hold my own expertise lightly enough that I could genuinely hear what was different about each client's situation.

The executives I worked with during that period were, almost without exception, highly capable people who were stuck — not because they lacked intelligence or experience, but because they were too close to their own problems to see them clearly. They needed distance. They needed someone who could reflect back what they were saying without the organizational filters that distorted every internal conversation.

That is a different kind of value than the value a CIO provides. And it is, I have come to believe, one of the most important things one executive can offer another.

The Thread That Connects It All

Looking back across a career that has moved between large public institutions, private sector transformation, and executive advisory work, I can see a thread that connects it all.

The problems that matter most — the ones that determine whether an organization thrives or stagnates, whether a leader grows or plateaus — are almost never the problems that appear on the surface.

The technology problem is usually a governance problem. The governance problem is usually a trust problem. The trust problem is usually a clarity problem — someone, somewhere, is not being honest about what they actually believe, what they actually need, or what they are actually afraid of.

My work has always been about getting to that level. About creating the conditions — through relationship, through the right questions, through the kind of environment that makes honesty feel safe — where the real problem can finally be named.

That is what I believe executive development, at its best, is for. Not the transfer of frameworks or the accumulation of credentials. The cultivation of the clarity, the courage, and the relationships that allow a leader to see what is actually happening — and act on it.

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Chris Moore is the co-founder of Waypoint Collective and the founder and past President and CEO of Anchoram Canada. He has served as Chief Information Officer for the City of Edmonton and the City of Brampton, and has advised organizations ranging from CIBC and TMX Group to regional municipalities and technology startups.