Seen & Heard at CCI’s Chief of Staff Leadership Workshop

By: Gabriella Boulos
CCI Director of Programs & Events

Sixty senior leaders gathered in downtown Toronto on February 27 for CCI’s Chief of Staff Accelerator, a new leadership workshop from the team behind the Innovation Governance Program (iGP) and The AI GUIDE. Building on CCI’s track record of supporting scale-up executives, the event provided strategic insights for professionals navigating one of the most complex roles in modern business. Discussions focused on decision-making, prioritization, and leadership dynamics, equipping Chiefs of Staff with the tools to enhance their strategic influence.

Here are a few of the key takeaways from half-day session.

Decision-Making Under Pressure

The first panel, Essential Skill Sets for Chiefs of Staff, featured Clara Ma, founder of Ask a Chief of Staff, Karmen Lee, Chief of Staff to Michele Romanow, and Michelle L. Christian, Chief of Staff at the Canadian Mental Health Association (CMHA) Toronto. Discussions centred on how Chiefs of Staff balance strategic oversight with operational execution.

A key takeaway was the idea that Chiefs of Staff are not copilots, but air traffic controllers—responsible for ensuring alignment and efficiency across an organization rather than simply executing a CEO’s vision. Effective decision-making, panelists noted, hinges on distinguishing between choices that are easily reversible and those that are not. In fast-moving environments, speed is often more valuable than perfection, with the best CoS professionals focusing on ensuring that bad decisions can be undone rather than obsessing over getting every decision right from the outset.

Filtering the Noise

The second panel, Navigating Leadership & Workplace Dynamics, was moderated by Allyssa Keep, Chief of Staff to retired BlackBerry Chairman and co-CEO Jim Balsillie, and featured Garry Keller, Vice President at StrategyCorp Inc., Lee Pham, Executive Partner at Teleiosis Consulting, and Mel Wright, Vice President of Communications at Intact Financial Corporation. Panelists underscored the importance of protecting a CEO’s focus—not by making decisions for them, but by ensuring that only the most essential matters reach their desk.

“CEOs rarely struggle with making decisions—they struggle with the sheer volume of them,” one speaker noted. A Chief of Staff’s job is to shield leaders from distractions, acting as a filter that keeps non-essential priorities from derailing an organization’s focus. One practical strategy is the “Parking Lot” approach: when a new idea or issue arises, evaluate whether it aligns with core business priorities. If not, table it for later.

The ‘Village Idiot’ Principle

Another insight that resonated was the idea that 80% of a Chief of Staff’s job is unwritten—requiring constant learning and adaptation. Embracing what one speaker called the “village idiot” mindset can be an asset: asking seemingly obvious questions early on can accelerate the learning curve and establish credibility faster. One recommended approach for new Chiefs of Staff is to conduct a listening tour within their first 30 days, meeting with key stakeholders to build a deep understanding of organizational dynamics.

Culture, Operations, and Strategy

Clara Ma, a leading expert on the Chief of Staff function, outlined three foundational pillars of the role: Culture, Operations, and Strategy. Culture, she explained, is more than a company’s mission statement—it’s the behaviours and structures that define how work gets done. Operations ensure that an organization functions effectively, while strategy provides long-term alignment with business goals. Chiefs of Staff, she argued, must navigate all three seamlessly to maximize their impact.

Mastering Prioritization

In a high-pressure breakout session, Lianne Vineberg, founder of T6 Talent Partners, walked participants through prioritization strategies under pressure. The most effective leaders, she emphasized, define their top priority at any given moment—because “if everything is a priority, nothing is.”

To separate urgency from importance, she advised using structured frameworks such as RICE Scoring, Impact vs. Effort, or Weighted Prioritization Models. These tools help leaders focus on the initiatives that drive revenue, mitigate risk, or advance strategic objectives, rather than reacting to the loudest demands in the room.

The Takeaway: Clarity Over Busyness

A closing insight summed up the workshop’s key theme:

“The best leaders aren’t the busiest—they’re the clearest on what moves the business forward.”

For Chiefs of Staff, success is not measured by workload but by ensuring that the right things get done.

If you would like to participate in a future Chief of Staff workshop, or learn more about our events and programming offerings, contact Gabriella Boulos at gboulos@canadianinnovators.org.