TLP505: Why Leadership Coaching So Often Fails

Will Linssen is the CEO of Global Coach Group, and the author of "Triple Win Leadership Coaching: The Coach's Guide to More Impact, More Coaching, and More Clients." In this conversation, Will challenges the traditional model of leadership coaching. Too often, coaching focuses on the leader while leaving the team out of the equation—one reason why team satisfaction frequently remains low even when leaders feel they've made progress. Will explains how great coaches assess coachability before the work even begins, why ego is often the biggest barrier to meaningful change, and what leaders in global, multicultural environments consistently misunderstand about communication and feedback. We also explore the impact of AI on leadership. Will argues that decades of accumulated expertise are losing their advantage. The leaders who will thrive going forward aren't the ones with all the answers—they're the ones who know how to ask the right questions. If you've ever wondered why leadership development often fails to stick inside organizations, this conversation offers a candid look at what's missing—and what needs to change. Find episode 505 on The Leadership Podcast, YouTube, or wherever you get your podcasts! Watch this Episode on YouTube | Will Linssen on Why Leadership Coaching So Often Fails https://bit.ly/TLP-505 Key Takeaways [03:26] Will reveals why traditional coaching fails: coworkers are left out, so their satisfaction with the leader's growth drops to as low as 18%. [05:23] Will reframes leadership development from "project me" to "project we" — and why that single shift drives real momentum. [10:30] Will explains how quarterly co-worker feedback keeps both the leader and the team mutually accountable for results. [12:01] Will names the two biggest predictors that a leader won't change: ego and job insecurity. [17:03] Will shares what 100,000+ leaders across six continents have in common — and where culture changes the game. [21:37] Will makes the case for leading with questions in high-hierarchy cultures as the fastest way to unlock smart, silent people. [26:20] Will reveals the belief about leadership he changed his mind about most after 30 years: outside-in behavioral change beats inside-out every time. [28:13] Will walks through the Triple Win business case that connects leader behavior to team behavior to measurable numbers. [35:50] Will warns that AI is depreciating your leadership experience premium fast — and what that means for your role. [39:16] Will's single action item for every leader in 2026: ask your team what advice they have for you, pick one thing, and go. [40:29] And remember..."A life is not important except in the impact it has on other lives." - Jackie Robinson Quotable Quotes "Leadership is not about the leader. It's about the people the leader is leading." "You need to change the leader's system, not just the leader." "The more you make leadership about "we" and the less you make it about "me" — realizing that "we" includes "me" — the more it makes total sense." "Leadership is co-creating change with coworkers." "Ego is total poison for coaching." "If adults don't want to change, they will not change." "We're not perfect people every day, but we can commit to being better every day." "We don't focus on those who need our help the most. We focus on those who want our help the most." "Don't ask closed questions. Ask the how question — that's where execution breaks down." "The moment you start making leadership about yourself, you're already making the first misstep." "Leaders only change when the new outcome is important enough to them." "As human beings, we have more in common than our passports divide us." "Smart people with AI can out-leader you very quickly. Be ready for that." "The leader is like a symphony orchestra conductor — the one who makes everything work together without playing an instrument." These are the books mentioned in this episode Resources Mentioned The Leadership Podcast | theleadershippodcast.com Sponsored by | www.darley.com Rafti Advisors. LLC | www.raftiadvisors.com Self-Reliant Leadership. LLC | selfreliantleadership.com Will Linssen | www.facebook.com/coachlinssen Will Linsse LinkedIn | www.linkedin.com/in/wlinssen Global Coach Group Website | globalcoachgroup.com