When Leaders Struggle: Stephen Moss on Career Setbacks, Mentorship, and Finding Your Way Forward

<p>What happens when a career that looks successful from the outside takes an unexpected turn? And how do you find a new sense of purpose when your professional identity no longer fits?</p><p><br></p><p>On this episode of Telling My Story, host Henry Chiwetelu welcomes Stephen Moss, founder and president of Executive Springboard, an organization that helps leaders navigate pivotal career moments through mentorship from experienced corporate executives.</p><p><br></p><p>Stephen’s journey includes serving as a Chief Marketing Officer four times. But his fourth experience lasted only 18 months and left him questioning what had gone wrong. Rather than ignoring the experience, he researched why executives struggle when entering new roles and used what he learned to build Executive Springboard.</p><p><br></p><p>Today, the organization has more than 100 mentors across 14 countries, helping leaders navigate promotions, executive transitions, leadership development, succession planning, and career endings.</p><p><br></p><p>In this conversation, Stephen opens up about professional setbacks, the value of learning from people who have walked the same path, and why even experienced leaders need guidance during moments of change.</p><p><br></p><p>In this episode, we explore:</p><p>● What Stephen learned from his own difficult executive transition.</p><p>● Why talented leaders sometimes struggle in new roles.</p><p>● The difference between mentorship and coaching.</p><p>● How the right mentor can help leaders navigate uncertainty.</p><p>● Why the first months in a new leadership position matter.</p><p>● Common mistakes organizations make in succession planning.</p><p>● How to handle career setbacks and rebuild professional confidence.</p><p>● Why career endings can become opportunities for a new beginning.</p><p><br></p><p>Connect with Stephen Moss on:</p><p>https://execspringboard.com/</p><p><br></p><p>Whether you&#39;re an aspiring leader, an experienced professional, a business owner, or someone facing an unexpected career transition, this conversation offers practical insights into leadership, resilience, and the importance of learning from other people&#39;s experiences.</p>