If you’ve ever been told to “just add AI,” this conversation will change the way you lead. We sit down with five-time founder Sean Lagon to unpack the uncomfortable truth: technology changes nothing until people do. From media and clean tech to industrial logistics and now AI-powered outsourcing, Sean shares the patterns that actually move a P&L—behavior-led change, precise partner selection, and a sober approach to risk that executives can live with.
We trace Sean’s journey from building a Calgary logistics platform to launching Outforce.ai, a data-driven way to cut through the noise of 79,000 outsourcing firms and match companies with the right agency by domain expertise, stack depth, and culture fit. Sean explains why referrals fall short, how industry constraints like HIPAA and finance compliance reshape requirements, and what due diligence prevents painful misses. Along the way, he revisits a pivotal lesson from his media-tech days: pivoting from disruption to enablement because decision-makers won’t trade vendor risk for career risk.
The heart of the episode is a practical blueprint for enterprise AI adoption. Start with a process audit, not a tool wishlist. Define behaviors first, then introduce software that makes the winning behavior easier. Measure impact in cycle time, error rate, and EBITDA—not demos and dashboards. We get into curiosity and critical thinking as the meta-skills of this era, from prompt design to human-in-the-loop governance, and why the most curious ICs often become cross-functional AI project leaders. We also tackle scaling teams through the “square” stages—3, 9, 27, 81—and making the hard calls when a brilliant builder isn’t the right executive to run the next chapter.
If you’re a founder, operator, or exec wrestling with AI strategy, outsourcing selection, or org design at scale, you’ll leave with a clearer map and practical next steps. Subscribe, share this episode with your team, and leave a review telling us the one process you’re most eager to automate next.