Leadership Development Is the Answer to a Question You Haven't Asked Yet
I know that sounds like a riddle.
It's not.
It's the pattern I see play out every single time.
I've worked with dozens of organizations over the past seven years, across industries, across sizes, across missions. And one thing stays consistent: organizations pursue leadership development without clarifying the problem they're actually trying to solve.
Now, that sounds obvious on the surface. "We want to develop our leaders. That's why we want leadership development."
OK. But why? What's actually happening in your organization that made you pick up the phone?
The Real Problems Hiding Behind "We Need Leadership Development"
When I push on this question, a few things typically surface:
Our leaders aren't actually leading
Our leadership team isn't on the same page
Our managers don't see themselves as leaders
Employee engagement is dropping and we don't know why
Here's what's important about that list: those aren't skill problems. Those are identity problems. They go well beyond what traditional leadership development is designed to address.
Traditional leadership development focuses on skills. Tips and tricks. The mechanics of leadership.
And there's nothing wrong with skills training. But if the real issue is that your managers don't see themselves as leaders, no amount of communication workshops will fix that. If your leadership team isn't aligned on where you're headed, a seminar on delegation isn't going to close that gap.
This is exactly why traditional leadership development typically fails. We're deploying a solution without connecting it back to the specific organizational challenge it's supposed to solve.
We're answering a question we never actually asked.
The Goal Isn't Leadership Scholars
Here's the thing you have to understand: the goal of leadership development is not to make your people smarter about leadership.
It would be great if they became more knowledgeable. But knowledge doesn't matter until it turns into action. And action doesn't matter unless it's aimed at the right target.
The real goal is getting your leaders leading in a way that overcomes your unique organizational challenge.
That's a very different bar than "we did a leadership training."
Get Clear on the Question First
Before you pursue leadership development, you have to get honest about what you're actually trying to solve. Not the generic version. Your version.
Are you asking:
How do we get our leaders on the same page?
How do we get managers to step into a leadership identity?
How do we boost employee engagement?
How do we build a culture that retains our best people?
Each of those questions leads to a fundamentally different solution. Treating them all with the same generic training is how organizations end up with decent but ultimately unhelpful programs that check a box and change nothing.
Why This Matters Even More for Mission-Driven Organizations
For the nonprofits and mission-driven organizations I work with, the stakes here are even higher. You don't have the budget or the bandwidth to experiment with solutions that don't work the first time. Every dollar you spend on leadership development that doesn't connect back to a real organizational challenge is a dollar that didn't go to your mission.
You can't afford to experiment with a generic solution. You need something that works.
And that means getting really clear, up front, on the real problem you're solving.
A Different Approach
When an organization comes to me wanting leadership development, I always stop the conversation. Before we talk about programs or timelines or content, we go back to one question: What impact does the solution need to make?
What's the actual problem we're trying to solve? What does success look like for your organization specifically?
Once we're clear on that, then we build the right solution. Not a generic one. The right one.
Your Diagnostic Questions
Before investing in any leadership development, ask yourself:
What specific organizational challenge prompted this need? (Not "we should develop leaders" but the actual problem you're experiencing)
What would success look like? (Concrete, measurable outcomes specific to your organization)
Is this a skill problem or an identity problem? (Most are identity problems that require different solutions)
How will we know if it worked? (Beyond "leaders learned things")
Ready to Ask the Right Question First?
If you're seeing patterns across your leadership team but aren't sure what problem you're actually trying to solve, contact me to discuss your situation. We can spend time diagnosing what's actually stuck in your organization and whether your current approach to leadership development is aimed at the right target.
Because if your organization has invested in leadership development before and it didn't stick, there's a good chance the problem wasn't the training—it was the diagnosis.