Seen & Heard: CCI’s Chief of Staff Accelerator in Ottawa

Participants from across the public, private, and non-profit sectors gathered in Ottawa on April 16 for CCI's Chief of Staff Accelerator, a full-day leadership workshop. The event brought together aspiring and current Chiefs of Staff for a day of candid conversation, hands-on learning, and peer community building, all grounded in the real-world challenges that define the role.

Here are some of the key takeaways from the day.

The Many Models of the Chief of Staff Role

The day opened with a panel featuring four Chiefs of Staff representing different organizational contexts: William Stockdale (CoS at ANVIL), Morgan Bello (VP, Strategy and CoS at YMCA of the National Capital Region), Jennifer Henderson (CoS and Corporate Secretary, Women and Gender Equality Canada), and Kendra Wilcox (CoS to the Minister of Women and Gender Equality and Secretary of State for Small Business and Tourism), moderated by Gabriella Boulos.

A common thread emerged immediately: almost no one in the room had a job description waiting for them when they arrived. Most wrote it themselves. The panel surfaced just how differently the role operates across sectors; in government, where authority and defensibility matter most; in the non-profit world, where resource constraints shape every decision; and in tech and scale-ups, where speed is the dominant pressure.

One theme that resonated across all four panelists was the principal relationship. Building trust with a principal, they agreed, is less about proximity and more about demonstrated judgment over time, particularly in organizations where the CoS was brought in through an existing relationship rather than a formal hiring process.

Breakout Streams: Getting In and Moving Up

Clara Ma, founder of Ask a Chief of Staff, and Lianne Vineberg, founder of T6 Talent Partners, split the room by experience level, but their messages converged on the same core idea: specificity is a superpower.

For aspiring CoS professionals, Clara pushed back on the instinct to stay broad. Narrowing your focus by company scale, industry, and the type of principal you'd work best alongside opens more doors than "I'm open to anything" ever will. For current CoS professionals, Lianne made the same case about influence: before trust exists, reframe problems, pre-wire stakeholders, and ask for small moves. After trust exists, shift to shared metrics and joint accountability. Influence gets the work started. Partnership keeps it going.

Hands-On Workshop: Real-World Case Scenarios

Clara Ma returned after lunch to facilitate a peer problem-solving session structured around a simple but powerful premise: nobody knows everything, but everyone knows something.

Participants broke into small groups to work through their own real challenges framed not as tool recommendations, but as genuine organizational problems. The exercise was governed by Chatham House Rules and a set of community agreements designed to mirror the confidentiality and discretion that the CoS role itself demands. Groups were asked to share experience, not advice, a distinction that made the conversations noticeably more candid.

Navigating Power and Politics: Performing Under Pressure

The afternoon session with Lianne Vineberg drew on two breakout case scenarios, one on prioritizing twelve competing strategic initiatives with a stretched CEO and another on leading an AI mandate.

Vineberg also shared her Pocket Guide to CoS as a practical reference for participants. She grounded the role in a “CoS Resilience Stack” built around focus, influence, composure, decisiveness, energy management, and a clear sense of forward direction.

She also introduced a simple way to cut through noise in high-pressure moments. If something does not affect revenue, risk, or strategic momentum, and will not matter in 90 days, it should not be the priority right now.

Takeaway

From morning to afternoon, a consistent theme ran through every session: the Chief of Staff role is not defined by how much you carry, but by how clearly work moves without you holding it.

The best Chiefs of Staff in the room weren't the busiest. They were the most deliberate about what they owned, what they delegated, and what they stopped.

Thank you to Ask a Chief of Staff for joining as a content partner for this accelerator in Ottawa.

If you would like to participate in a future Chief of Staff workshop or learn more about CCI's events and programming offerings, contact Gabriella Boulos at gboulos@canadianinnovators.org.
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About the Council of Canadian Innovators

The Council of Canadian Innovators represents more than 170 of Canada’s fastest-growing technology companies. Founded in 2015, CCI advocates for policies that help Canadian innovators scale globally, create prosperity at home, and strengthen Canada’s economic sovereignty.