In the world of leadership and development (L&D), playing it safe often leads to stagnation. That’s one of the key insights shared by Sean Conley, Global Learning and Development Leader at in a recent episode of Skilled. With over 35 years of experience across industries and continents, Sean’s approach to leadership challenges the status quo, focusing on the importance of embracing failure to drive meaningful change.
Failure: A Pathway to Success
Sean recalls a defining moment when he led a session on change management that was labeled an “epic failure” by a senior executive. Instead of following the expected path, Sean invited a panel of unconventional speakers—a Buddhist monk, a street performer, and an author—to discuss how change impacts people on a deeper, more personal level.
The result? A senior leader declared the session a failure. But for Sean, it was a powerful success. “My job was to push buttons… sometimes people need to hear a message they don’t want to hear, and in that message comes their greatest growth,” Sean explained. This moment became a key lesson for him—and for anyone in leadership: real growth often comes from pushing boundaries and challenging comfort zones.
Easy, Engaging, Impactful: Sean’s Approach to L&D
Sean’s leadership philosophy is built on three core pillars: easy, engaging, and impactful. In his view, learning should be simple enough for anyone to understand, engaging enough to captivate learners, and impactful enough to drive lasting change. “If it’s not easy, people won’t ask questions… and if they don’t get it, you’ve wasted their time,” Sean pointed out.
This focus on human-centered learning emphasizes the importance of creating an environment where learners feel safe to engage, ask questions, and take risks—all while pushing the boundaries of traditional L&D practices.
Be Bold, Take Risks
Sean’s key message for L&D leaders is clear: don’t be afraid to take risks. Whether it’s trying something unconventional in a learning session or challenging people with uncomfortable truths, real progress requires courage. “If you want to do something interesting… be bold, dare,” he advises.
For leaders looking to make a lasting impact, Sean’s story serves as a reminder that failure is often the foundation for success. By embracing discomfort and pushing through perceived failures, you can create learning environments that foster true growth and development.
For a deeper dive into the conversation, watch the full episode here:
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