“It’s complicated and it depends”: Why embracing complexity makes us better at evaluating Leadership Development
Leadership development is full of good intentions, but not always easy answers As someone who works at the intersection of coaching, research and organisational change, I’m often asked: “How do we know if it’s working?”The honest answer? It depends. And that’s not a cop-out, it’s a starting point that opens the door to real learning. Because once we stop looking for simple proof, we can start asking better questions - and that’s where the real transformation begins.
I sometimes quip that it’s easy being a Research Psychologist because the answer to everything is “it’s complicated” or “it depends.”
Perhaps that comment is a little glib, but it’s rooted in the reality of our profession – people and their behaviours rarely fit into neat little boxes. Yet at the same time, we need to make sense of the incredible complexity of people, their organisations, and the context they are operating in. So how do we strike the balance?
Why leadership development is tricky to measure
There’s often a push to demonstrate immediate, measurable outcomes from leadership programmes. It’s understandable - organisations want to see return on investment and we can often be tempted to draw a straight line between A and B (or development program and outcome). We might be able to assess interventions in this way in more controlled environments, like clinical trials, but in the real world, professional development is messy, non-linear and dependent on so many unpredictable factors.
Confidence wavers. Trust builds slowly. Impact sometimes shows up in the quiet shift in how a manager gives feedback, or the conversations that didn’t escalate. And sometime people feel excluded, or disengaged but don’t have a forum to express their concerns. These things don’t usually show up in standard feedback forms or pre/post surveys, where the focus is often based on the learner’s experience, their intentions to implement, and their own self-assessment of competencies gained.
That’s where “it depends” comes in. Because the right evaluation approach depends on the context:
- What’s the culture and climate of this organisation?
- What are leaders actually being asked to lead through right now?
- What does success look like here - and, importantly, to whom?
- Who are the people our leadership development programmes are aiming to impact? And crucially, who’s viewpoint might we be overlooking?
Asking better questions, not just ticking boxes
In my work evaluating leadership development with purpose-led organisations, I focus on asking the right questions before jumping to measures.
For example, in a recent partnership with an international charity, the goal wasn’t just to track whether people completed a leadership development program, or to ask questions about how valuable they found the experience. It was to understand how their leadership culture was shifting over time, and what kind of support helped those changes stick.
This means working closely with their L&D leads and key stakeholders, creating space for reflective conversations, and building an evaluation framework that isn’t just about accountability – it’s heavily focused on learning. When evaluation is co-designed and context-aware, it becomes a tool for insight, not just reporting.
Making peace with complexity (and making better decisions)
I often say that my job is to help people and organisations make sense of complexity. That’s especially true in leadership development. The world leaders are working in is messy and ever-changing. Sometimes we don’t get everything right and are putting too much effort into things that don’t really shift the dial, and sometimes we overlook the small things that are making a bigger difference than we ever imagined. Our evaluation needs to reflect that reality, not shy away from it.
By embracing nuance, we get clearer on what’s working andwhat needs rethinking. We support a culture of reflection, not perfection. And we make better decisions, not because we know everything, but because we’re asking thoughtful questions, to a diverse range of people, and leading with curiosity and openness.
In a world that craves quick answers, holding space for complexity, isn’t always easy but it’s a powerful mindset shift.
What might become possible in your organisation if you stopped asking “Does our leadership development program work?”, and started asking “What does effective leadership really look like here, and what genuinely makes a difference, for whom, and under what conditions?
