What Most Organizations Get Wrong About Developing Leaders
Every year, U.S. companies spend over $370 billion on leadership development. And yet, the majority of leaders—at every level—say their organizations have a leadership problem.
That gap should give you pause.
I’ve spent the better part of two decades working with organizations across industries, and I’ve seen this pattern play out more times than I can count. Companies invest in training. They send people to workshops, bring in speakers, buy assessments. And then six months later, nothing has changed. The same decisions get made the same way. The same conflicts resurface. The same people leave.
The problem isn’t a lack of investment. It’s a lack of understanding about what leadership development actually is—and what it isn’t.
Leadership Development Is Not a Training Event
Let me be direct: a two-day offsite doesn’t develop leaders. Neither does a Harvard executive program, a 360-degree feedback report that sits in a drawer, or a series of lunch-and-learns. These things can be useful inputs. But they are not leadership development.
Leadership development is the sustained, intentional process of building an organization’s capacity to produce leaders who can execute strategy, build high-performing teams, and navigate complexity. It’s a system—not an event.
That distinction matters because organizations that treat leadership development as an event get event-level results: a short-term lift in enthusiasm, followed by a return to baseline.
Organizations that treat it as a system—where development is embedded in how work happens, how feedback flows, and how people are promoted—see compounding returns over time.
Why Most Leadership Development Programs Fail
In my experience, leadership development programs fail for four predictable reasons.
They’re disconnected from real work. The best learning happens in context—when a leader has to make an actual decision, navigate an actual conflict, or lead an actual team through an actual challenge. Programs that pull people out of work and put them in a classroom or retreat setting are working against this. The content doesn’t stick because it’s not anchored to anything real.
They focus on individual leaders, not leadership systems. Most programs develop individual leaders in isolation. But leaders don’t operate in isolation. They operate inside systems—reporting structures, incentive systems, decision-making norms—that either reinforce or undermine the behaviors you’re trying to develop. If your leadership program teaches people to empower their teams, but your organization rewards leaders who control and micromanage, the system wins every time.
Senior leaders aren’t involved. I’ve watched countless organizations send their mid-level managers to leadership programs while the senior team does something else. The message that sends is unmistakable: this is for them, not us. Effective leadership development is visible at the top. Senior leaders model the behaviors, participate in the process, and create psychological safety for others to do the same.
There’s no accountability for application. What happens after the program ends? In most organizations: nothing. People go back to their jobs, their old habits reassert themselves, and the training becomes a line item on a resume rather than a shift in how they lead. Effective programs build in structured follow-through—peer accountability groups, manager check-ins, visible commitments.
The Foundations of Effective Leadership Development
So what does effective leadership development look like? In my experience, it shares four characteristics.
It starts with a clear picture of what leadership needs to look like in your organization. Generic leadership competencies—”communicates effectively,” “drives results”—aren’t useful. They’re too abstract to change behavior, and they don’t reflect what leadership actually needs to accomplish in your specific context. Before you design any development experience, you need to answer: what do leaders in this organization need to do, in service of this strategy, to produce this result?
It develops self-awareness as a foundation. Most leadership problems I’ve seen—at the individual level—trace back to a gap in self-awareness. Leaders who don’t know how they come across can’t change how they come across. Assessment tools (360 feedback, behavioral interviews, structured observation) are valuable not as endpoints, but as starting points for honest conversations about how a leader’s impact matches their intentions.
It creates conditions for practice and feedback. Real development requires real reps. Stretch assignments, action learning projects, cross-functional roles, and coaching relationships all create the conditions for leaders to practice new behaviors in relatively lower-stakes environments—and get real feedback about what’s working and what isn’t.
It’s sustained over time. Leadership development is not a sprint. The organizations that produce the most effective leaders treat development as a multi-year commitment, not a quarterly initiative. They build feedback into the normal rhythms of work. They track leadership behavior the same way they track operational metrics. They make development a management responsibility, not an HR program.
Building a Leadership Pipeline: Where to Start
One of the most common questions I get is: where do we start? Especially in organizations where leadership development has been inconsistent or absent, the prospect of building something systematic can feel overwhelming.
Here’s where I’d start.
Get clear on your current state. Before you can close a gap, you need to understand where you are. Who are your high-potential leaders? What capabilities do they currently have? What capabilities does your strategy require? Where’s the gap? This diagnosis doesn’t have to be elaborate—but it has to be honest.
Identify your critical leadership levels. Not all levels of leadership require the same development focus. A first-time manager needs fundamentally different capabilities than a VP leading a business unit, who needs different things than a C-suite executive navigating enterprise strategy. Map your critical levels, and design development experiences appropriate to each.
Make development part of the manager’s job. One of the most underused leadership development levers in most organizations is the manager-direct report relationship. When managers are expected—and equipped—to develop their people through regular coaching conversations, feedback, and stretch assignments, development becomes part of how work happens rather than a separate activity.
Build accountability into the system. Development goals that live only in an HR system will never move the needle. Connect development to performance management, to succession planning, to promotion criteria. When leaders know that their investment in developing their people has real consequences for their own advancement, the calculus changes.
The Leadership Behaviors That Matter Most
Across the organizations I’ve worked with, certain leadership behaviors consistently separate effective leaders from ineffective ones—regardless of industry or function.
Clarity. Effective leaders create clarity—about priorities, about expectations, about what success looks like. Ambiguity is expensive. It creates misalignment, duplicated effort, and disengagement. Leaders who can distill complexity into clear direction are disproportionately valuable.
Accountability without blame. The organizations with the strongest cultures hold people accountable while maintaining psychological safety. These two things are not in conflict—but leaders who haven’t developed this skill often treat them as if they are. They either avoid accountability or use it as a club. Neither works.
Developing others. The best leaders I’ve worked with are deeply invested in the development of the people around them. Not in a performative way—but in a real, practical way. They notice when someone is ready for more. They create stretch opportunities. They give feedback that’s honest and useful. They see their job as multiplying capability, not hoarding it.
Adapting under pressure. Most leadership development happens in normal conditions. But leadership is tested under pressure—in ambiguity, in conflict, in crisis. Leaders who can regulate their own emotional responses, maintain perspective, and make sound decisions when things are hard are significantly more effective than those who can only perform in favorable conditions.
The Organizational Culture Connection
I can’t write about leadership development without mentioning culture, because the two are inseparable.
Your culture—the actual values, behaviors, and norms that govern how work gets done—is the environment in which leaders operate and develop. A culture that rewards short-term results over people investment will undermine even the best leadership development program. A culture that treats feedback as a threat will make honest development conversations rare and performative.
The leaders in your organization are also the primary drivers of culture. Their behaviors—what they reward, what they ignore, what they model—send constant signals about what’s really valued. Developing leaders and developing culture are the same work, approached from different angles.
If your leadership development program isn’t explicitly connected to your culture work—or if you’re doing one without the other—you’re leaving a significant part of the system on the table.
What to Expect—and What Not to Expect
I want to be honest about timelines, because unrealistic expectations are one of the reasons leadership development programs get abandoned before they produce results.
You will not transform your leadership bench in six months. You might see some early indicators—changes in how meetings run, a shift in feedback quality, a few individual leaders visibly stepping into their development. But systemic change takes longer.
What you should expect in the first year: increased clarity about what good leadership looks like in your organization, more intentional feedback conversations, and a baseline measurement of where your leadership capabilities currently sit.
What you should expect in years two and three: measurable shifts in how decisions get made, improved employee engagement in teams with strong leadership, and a deeper pipeline of leaders ready for expanded roles.
That’s not a slow return on investment. That’s how organizations build durable capability.
Working with gothamCulture
At gothamCulture, we work with organizations that take leadership development seriously—and want to build it as a system, not a series of events. We bring together leadership assessment, culture diagnosis, targeted development experiences, and coaching to help organizations understand where they are, where they need to go, and how to build the leadership capability to get there.
If your organization is trying to figure out where the real gaps are, we can help you run the diagnosis. If you’re further along and need to design or refine a development architecture, we can work alongside your internal team to build something that actually holds up over time.
Let’s talk about what leadership development could look like in your organization.
