For many business owners, transition has traditionally been something left for later, tied to succession or a future moment when the timing felt right. That approach is shifting.

Some businesses are built in environments where conditions are predictable. Others are built where conditions are constantly shifting. For Geoff Gay, leading Athabasca Basin Development has meant operating in the latter. Northern geography, resource cycles and global forces all shape the outcome, often in ways that’re outside any single company’s control.

Leadership is often associated with control, decisiveness and having all the answers. Phil Jewell sees it differently. From leading soldiers early in his career to building leadership programs across North America, his perspective has been shaped by environments where clarity, trust and accountability aren’t optional.

Many business owners spend years waiting for the “right time” to make a major decision about their company. Whether that means investing further, bringing in partners or preparing for a sale, the instinct is often to wait for clearer market conditions. Christine Pound believes that moment rarely arrives.

For many prairie business owners, global instability can feel distant. Tariffs, geopolitical tensions, supply chain disruptions and social media activism can often seem like issues for multinational corporations, not local SMEs. Grant Kook sees it differently. As Founder, President, Chief Executive Officer, and Chair of Westcap Mgt. Ltd., and now Chair of BTF Saskatoon, Grant brings a broad perspective to prairie business.

Many owners spend years building a business, only to discover late in the process that deals don’t fall apart on price alone. They unravel on terms, trust and expectations that were never fully negotiated in the first place. That reality came through clearly in our conversation with William M. Donnellan, President and CEO of IRL Group of Companies.

For many Alberta business owners, the challenge right now isn’t opportunity. It’s uncertainty.Geopolitical pressures, shifting trade relationships, labour constraints, and rising operating costs are creating decisions that feel harder to time and riskier to make. As Todd Millar, President and CEO of TEC Canada and Chair of BTF Alberta 2026, put it, owners are dealing with forces that sit well beyond tariffs alone.

When George Armoyan, Executive Chairman of G2S2 Capital, sat down with Christine Pound for a BTF keynote conversation, he spoke less about growth curves and more about judgment. It was less about timing exits and more about surviving cycles. From immigrating to Canada as a teenager to building one of the country’s largest private investment companies, George’s perspective has been shaped by volatility.

Some enduring businesses are built far from the usual centres of capital and attention. They take shape in environments where resources are constrained, execution matters and results speak louder than reputation. That perspective came through clearly during a conversation at BTF Winnipeg with Joshua Simair, Co-Founder and former CEO of SkipTheDishes.