Building Leadership That Lasts

Why Leadership Development Fails—and How to Fix It

Claire Monroe: Hey everyone—welcome back to The Science of Leading! I’m Claire Monroe, joined as always by Edwin Carrington. Today, we’re diving into one of those topics that sounds straightforward, but… honestly, so many organizations just get wrong: leadership development. Edwin, it feels like everywhere you look, someone’s hosting another “leadership essentials” workshop, but the needle barely moves. Why is that?

Edwin Carrington: You’re absolutely right, Claire. It’s a trap I’ve seen for decades. Too often, leadership development becomes a checkbox—send your managers to a weekend workshop, hand out a few binders, then expect some sort of transformation. The reality is, most of those efforts don’t translate into true behavioral change—certainly not the kind that drives engagement or performance. If anything, they breed cynicism—people see straight through “flavor of the month” solutions.

Claire Monroe: Yeah, and I… I remember at a previous company, we had these all-day seminars—lots of leadership theories, group exercises, mountains of notes. But after a few weeks, everyone just slipped back into old patterns. The tools were there, I guess, but… nothing stuck. Why do you think that happens? Is it just the format?

Edwin Carrington: Format matters, but it’s deeper than that. Leadership is highly situational. Generic, one-size-fits-all training fails because it ignores context—your culture, your business strategy, the unique pressure points leaders face. If development isn’t tailored, and if it isn’t part of a sustained journey, people revert to what’s familiar. And another piece—many programs overemphasize theory at the expense of practice. Leaders might “know about” coaching or decision making, but unless they’re actually doing it, the lessons fade away.

Claire Monroe: That rings true. It’s like running drills in sports but never scrimmaging. And it feels like leadership development just gets treated as an event—a “one and done”—instead of, you know, a journey.

Edwin Carrington: That’s exactly it. Lasting leadership growth needs long-term reinforcement, coaching, real opportunities to struggle and apply new skills—not just a seminar and a handout. Organizations that approach development as an ongoing process, with real support systems in place, see much stronger results. And the companies that do treat leadership like a backbone rather than a perk? They’re the ones who actually move the needle on engagement, retention, all those things that really drive the business.

Claire Monroe: So, just to put a bow on it—it’s not that leadership workshops or theory are useless. The issue is treating them as a quick fix rather than a step in a longer, more personalized journey. And that’s where most programs break down. I guess that’s where we go next—how you build real growth into these programs?

From Goals to Real-World Growth

Edwin Carrington: Let’s start with this: leadership development without clear goals is directionless. If you don’t know what you’re trying to accomplish—or how it supports business strategy—it just becomes noise. The strongest programs are laser-focused. They define the “why”: are you trying to improve team decision making? Build stronger succession pipelines? Reduce turnover? Those outcomes need to be clear and measurable—not just “let’s make everyone a better leader.”

Claire Monroe: Right, it’s like—without those north star metrics, you’re just sort of… wandering. And that alignment to business strategy and culture—it’s not optional? You need those leadership qualities that actually move the company forward, not just ones that check the “nice-to-have” box.

Edwin Carrington: Absolutely. You build from there with four core ingredients: practical learning, experiential training, consistent feedback and coaching, and support systems for long-term change. Each of those matters. Learning only works if leaders see the direct relevance—you’re solving real workplace challenges, not memorizing frameworks for a test. Experiential training? That’s where growth really happens. Give leaders stretch assignments—say, leading a cross-functional team, where failure’s a possibility, but support is built in. You don’t just grow by reading about it.

Claire Monroe: I love that example—seeing a new manager struggle through their first complex project. I mean, I’ve gone through it. You’re awkward, you stumble, but you learn ten times faster when the stakes are real. It’s so much different than, say, a simulation or case study on its own.

Edwin Carrington: Exactly, Claire. And when you combine those experiences with ongoing feedback—360 reviews, regular coaching check-ins—you help people build self-awareness, spot blind spots, and actually change behavior. I’ve mentored plenty of new leaders through that “identity shift.” Going from “I do the work” to “I help others succeed”—that’s a step no seminar can replicate. But with structured feedback and support, you watch their confidence and impact grow over time.

Claire Monroe: So, just to recap—you’ve got to have clear, business-aligned goals, but then you back that up with relevant learning, real stretch experiences, a lot of feedback, and structural support. That’s how you get the skills to actually stick and show up in day-to-day decisions, not just in a final exam or a dreaded role play.

Edwin Carrington: And you need all four ingredients—miss any one, and growth stalls. The remarkable thing is, when organizations do this well, you don’t just see individual improvements. You see systemic change—higher engagement, more agile teams, and much better succession planning down the road.

Claire Monroe: And that kind of transitions us… into what it really takes to make leadership development a permanent fixture in company culture—not just a project you launch when engagement dips.

Making Leadership a Cultural Constant

Claire Monroe: Okay, so let’s go even bigger picture: How do companies actually turn leadership development into part of their DNA, not just something HR launches every couple of years? What’s different about organizations where leadership growth feels like a “constant” instead of a campaign?

Edwin Carrington: You’re touching on the heart of it, Claire. The organizations that get this right see leadership development as woven into the fabric of daily operations. It isn’t a “program”—it’s how things are done. Senior leaders don’t just sponsor initiatives; they model the behaviors. Systems—from performance reviews to promotions—reflect both technical results and, just as importantly, how people grow and coach others. Over time, this creates a self-sustaining pipeline of leaders at every level.

Claire Monroe: It’s like, uh, the Navy SEALs. They don’t talk about culture in the classroom, they build it in the field, and test it under real pressure. And as Warren Buffett says, “culture eats strategy for breakfast.” The point being: If leadership’s part of how you operate every day, it gets reinforced in all the little moments—not just in big, lofty mission statements.

Edwin Carrington: Well said. And if I may, culture isn’t static. You reinforce it with data and accountability. That’s where metrics matter. If you want to prove that leadership development delivers real ROI, track engagement scores, retention, promotion rates, even customer satisfaction. Don’t measure activity—measure outcomes, over months and years. OAD’s experience shows that when you match leaders to roles that fit their behavioral strengths, performance compounds. But only if you keep tracking—not just after the first quarter, but long after the training ends.

Claire Monroe: So true. And I think that’s a gap a lot of organizations fall into—they track happy sheets after a program, but forget to check if people actually changed their day-to-day behaviors a year or two later. It’s not just about initial satisfaction; it’s about impact over time. And that’s how leadership becomes a real differentiator.

Edwin Carrington: And it’s also about building resilience for the future. The strongest organizations blend science and adaptability. When your leaders are constantly learning, practicing, and getting feedback, you’re not only future-proofing your talent—you’re building a culture that can adapt to whatever comes next.

Claire Monroe: Couldn’t have said it better. So for our listeners—if leadership development still feels like a “nice to have” or something to do just when it’s budget season, maybe it’s time to shift that mindset. Make it part of your culture’s backbone, and you’ll see the returns, even if they aren’t always immediate. Edwin, thanks as always for grounding us with perspective.

Edwin Carrington: Thank you, Claire. Always a pleasure—and for everyone listening, keep asking those tough leadership questions. That’s how it starts.

Claire Monroe: Alright, that’s it for today. We’ll be back in the next episode to unpack more of the science—and the real-world stories—behind better people decisions. Thanks for listening to The Science of Leading!

Edwin Carrington: Goodbye, Claire. Goodbye, everyone.