The Succession Conversation Most Business Owners Avoid | Mike Mack, X5 Management

The Succession Conversation Most Business Owners Avoid | Mike Mack, X5 Management

Most owners know succession planning matters. Almost none of them actually do it. In this episode of McStay on What Matters, Sean McStay sits down with Mike Mack, founder and president of X5 Management and author of the new book Succession, to unpack the conversation most founders avoid: what happens to the business when you are no longer the one holding it together. They get into why succession is really about making yourself replaceable, why your replacement should not be a copy of you, how a clear plan retains your best people instead of losing them, and the gap between intending to plan and actually doing it. Candid and practical, built for owners and leaders of small and mid-sized companies. What you’ll learn: * Why avoiding the succession conversation is what costs owners the most * How planning your succession makes you more valuable, not less * The three questions that reveal a real successor: do they get it, want it, and have the capacity * Why a clear path forward, even without guarantees, is your best retention tool * The difference between thinking about a plan and actually having one Chapters:00:00 Welcome, and Mike’s new book Succession01:07 Who Mike Mack is and what X5 Management does02:18 How X5 evolved from the original idea05:25 When to make your first hire07:59 Why slow and steady beats hiring to fix a problem08:38 The discovery process: where are you in three years?12:04 Succession: the gap between intention and action15:26 Making yourself replaceable, and the ego problem18:35 Why your replacement should not be another you21:23 Succession as a retention strategy, and timing25:31 Clarity over guarantees28:35 How to start the conversation at your own company33:27 “What if we train them and they leave?”36:23 The one thing every owner should do next38:57 Where to find Mike and the book About Mike Mack:Mike Mack is the founder and president of X5 Management in Edmonton, celebrating 20 years in 2026. X5 is in the people business: strategic planning, succession planning, leadership and team development, and executive coaching. Mike is the author of several books, most recently Succession. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.seanmcstay.com [https://www.seanmcstay.com?utm_medium=podcast&utm_campaign=CTA_1]

You Don't Matter Unless You Matter to Me - With Tony Chapman

Tony Chapman is a Marketing Hall of Legends inductee, entrepreneur, and host of Chatter That Matters. In this conversation we get into what it actually takes to earn attention in a world drowning in noise, why "too big to fail" has become "too slow to react," and how AI is reshaping who thrives and who gets replaced. Tony shares his head, heart, and hands framework for decision-making, why curiosity beats killer talking points, and the difference between using AI to do your work and using it to transform your work. If you're building a brand, leading a team, or trying to figure out what matters next, this one is worth your time. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.seanmcstay.com [https://www.seanmcstay.com?utm_medium=podcast&utm_campaign=CTA_1]

You Cannot Recruit Your Way Out of a Skills Crisis

Steve Cadigan, former Chief HR Officer at LinkedIn and author of Workquake, joins me to talk about what leaders are getting wrong about talent, development, and the future of work. We discuss why one-size-fits-all talent strategies are failing, why people are increasingly loyal to learning and growth rather than companies, and why organizations will not be able to recruit their way out of the accelerating need for new skills. Steve also shares lessons from LinkedIn’s rapid growth, his own transition after leaving the company, and why careers are built on trust more than hard work. This conversation is about development, but not in the classroom sense. It is about how leaders create the conditions for people to keep growing while the world around them changes. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.seanmcstay.com [https://www.seanmcstay.com?utm_medium=podcast&utm_campaign=CTA_1]

McStay on What Matters - 003 - Glenn Lesko and Judgement in leadership

In the third episode of McStay on What Matters, Sean sits down with Glenn Lesko, a partner at Pender and Howe and executive recruitment specialist with nearly three decades of experience finding and assessing senior leaders, to talk about judgment. What does it actually mean to use good judgment, and how do leaders develop it over time? Glenn shares how understanding an organization goes far deeper than a job description, why the gap between what companies say they need and what they actually need is where the real work begins, and how the best decisions in hiring and in leadership come from staying human in a process that often tries to be anything but. Glenn: https://penderhowe.com/en/ [https://penderhowe.com/en/] McStay on What Matters is a biweekly podcast about the decisions leaders carry alone and how they navigate them. YouTube Link: https://www.youtube.com/@SeanMcStay [https://www.youtube.com/@SeanMcStay] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.seanmcstay.com [https://www.seanmcstay.com?utm_medium=podcast&utm_campaign=CTA_1]

McStay on What Matters - 002 - Jason Donkersgoed and Reality in Leadership

In the second episode of McStay on What Matters, Sean sits down with Jason Donkersgoed, a leadership coach and consultant with over 30 years of experience leading teams across retail, finance, and higher education, to talk about reality in leadership. What happens when leaders avoid naming what everyone already sees? Jason shares what he has learned about surfacing difficult truths, building the trust required for honest conversation, and why the clearest thing a leader can do is often the kindest. McStay on What Matters is a biweekly podcast about the decisions leaders carry alone and how they navigate them. YouTube Link: https://www.youtube.com/@SeanMcStay [https://www.youtube.com/@SeanMcStay] Jason: https://www.linkedin.com/in/jason-donkersgoed/ [https://www.linkedin.com/in/jason-donkersgoed/] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.seanmcstay.com [https://www.seanmcstay.com?utm_medium=podcast&utm_campaign=CTA_1]