Mention evaluation in a room full of leadership development professionals and you can almost feel the energy change.
We know it’s important. Organizations need evidence that their investment in leadership development is making a difference. Yet evaluation is often treated as the administrative task that follows the learning, rather than something that contributes to it.
Perhaps that’s part of the problem.
Organizations invest enormous amounts of time and money developing leaders. Then, when it’s time to determine whether that investment worked, conventional evaluation often begins with familiar questions:
Was the program valuable? Would you recommend it? Did you learn something useful? How would you rate the facilitator?
There’s nothing inherently wrong with those questions. They tell us something about the participant’s experience. They tell us considerably less about whether that person is becoming capable of leading differently.
The moment we decide what to evaluate, we send a signal about what matters.
Even when we move beyond satisfaction to measure knowledge acquisition and observable behavior, we may still be working from an assumption that deserves examination: learning happens first, application happens second, and evaluation happens afterward to determine whether any of it worked.
What if that sequence is limiting what evaluation could contribute?
At Canvas, we’re challenging that assumption.
Evaluation does not simply have to measure development.
Evaluation can cause development.
Every evaluation directs attention
Imagine a leader has just completed an important developmental experience.
Ask her, “How satisfied were you with the program?” and you direct her attention toward the program.
Ask, “What did you learn?” and you direct her attention toward knowledge.
Ask, “What will you do differently?” and you direct her attention toward behavior.
Now ask something different:
What are you seeing differently now that you could not see before?
To answer, the leader must do more than recall information. She has to interpret her experience, examine the assumptions she brought into it, and consider whether something she previously believed has changed.
The question is no longer simply collecting information about development. It is inviting the leader to engage in the very thinking that makes development possible.
Every evaluative question asks us to do something with our experience. We recall what happened, interpret its significance, draw on our assumptions, beliefs and values, and decide what it means. In doing so, we may reinforce the way we already understand the world, or we may encounter something that challenges it.
The questions we ask determine what we invite people to examine. We can ask leaders to report what they learned, what they intend to do, or how effectively they performed. Or we can challenge them to examine the thinking behind their conclusions, recognize the assumptions influencing their choices, and reconsider perspectives they have long taken for granted.
One approach primarily collects evidence of what a leader knows or does. The other can also develop the capacity to question and evolve what drives that knowing and doing.
Why leaders return to familiar patterns
Sustainable leadership growth rarely comes simply from acquiring another technique. A leader can learn a new approach to giving feedback, navigating conflict, or delegating responsibility and still return to familiar patterns when the situation becomes uncomfortable.
The challenge may not be a lack of knowledge or skill. It may be the assumptions and stories shaping how that leader interprets the situation, what they believe is expected of them, and who they believe they need to be.
If development never reaches those underlying patterns, we may be teaching leaders new behaviors without changing what continues to drive the old ones.
Evaluation can help bring those patterns into awareness, creating opportunities for leaders to examine and intentionally evolve them.
What if evaluation is a leadership practice?
This raises a more fundamental question.
What if evaluation isn’t principally something an organization does to a leader?
What if it is also something leaders learn to do for themselves?
Much conventional organizational evaluation is externally oriented. Someone establishes the criteria, observes the behavior, measures the outcome, and determines whether the individual has met the standard.
Those things matter. Organizations need evidence, accountability, and a credible understanding of whether development investments are producing meaningful results.
Yet leadership increasingly takes place in conditions where there may be no established answer against which performance can immediately be evaluated. Complexity, ambiguity, rapid technological change, competing priorities, and decisions whose consequences may not be known for months or years all require something more than the ability to demonstrate a learned behavior.
They require discernment.
A leader must be able to examine what is happening, recognize how their own assumptions are influencing their interpretation, seek perspectives that challenge their thinking, consider the consequences of their choices, and determine whether their response needs to evolve.
That is an evaluative capacity. And it is one of the capacities leadership development should be strengthening.
The goal is not to make leaders independent of external feedback. It is to help them become increasingly capable of evaluating their own thinking and actions while remaining open to evidence and perspectives beyond their own.
When leaders learn to evaluate their own thinking, evaluation becomes more than a measurement activity. It becomes a practice of leadership.
What if evaluation were part of the learning, not the end of it?
If we accept that premise, the familiar end-of-program survey begins to look insufficient.
Development doesn’t occur only at the end of an experience. Why should evaluation?
At Canvas, we’re rebuilding our own approach around the belief that evaluation should be part of the learning, not simply the evaluation of learning.
That means creating intentional opportunities for leaders to examine their experiences before, during, and after formal development. It means paying attention not only to what people know or do, but also to how they are interpreting their experiences, how their thinking is evolving, and what difference that evolution is making for others.
A short reflection after a difficult conversation might reveal an assumption a leader hadn’t previously recognized.
Feedback from a colleague might challenge a familiar interpretation.
A coaching conversation might help someone examine the story they are telling themselves about why a situation feels threatening.
A developmental check-in months later might reveal not only whether a new behavior has endured, but what the leader has learned through attempting to sustain it.
These are opportunities to interrupt autopilot, strengthen awareness, and make development an ongoing practice, while also gathering evidence of how that development is unfolding.
What organizations could see
Consider what organizations could understand if evaluation followed development throughout the journey, rather than concentrating primarily on its outcomes.
They could see where leaders began, how their perspectives evolved, whether those shifts translated into different choices and behaviors, and what impact those changes were beginning to have on others. They could also identify where development had stalled, where organizational conditions were reinforcing old patterns, and where further investment might make the greatest difference.
This would not eliminate the need for conventional measures. It would place them within a richer understanding of development, one that recognizes the difference between acquiring a capability, changing how we think, and sustaining that change in the realities of organizational life.
We are designing our evaluation approach to bring together different forms of evidence across three interconnected dimensions: mindset transformation, behavioral change, and organizational impact.
Each tells us something different. None, on its own, tells us the whole story.
The ambition is not simply to produce more sophisticated reports. It is to create an approach that provides organizations with credible evidence of development while strengthening leaders’ capacity to keep evolving long after the formal experience has ended.
Perhaps we’ve been asking evaluation to do too little
Organizations should expect evidence from leadership development. They should understand whether people are thinking differently, whether that change is influencing how they behave, whether others are experiencing a difference, and whether development is contributing to outcomes that matter.
We should not lower that expectation. We should expand it.
For years, one of the dominant questions in leadership development has been: How do we prove that development worked?
It’s an important question, and one we must continue answering.
Yet there is another question worth asking alongside it:
How might the way we evaluate become part of how leaders develop?
Imagine if evaluation were intentionally designed not only to help organizations understand what had changed, but also to strengthen leaders’ ability to recognize when their own thinking needs to change.
Perhaps the most important outcome of a developmental experience is not simply that leaders can demonstrate what they learned when we ask them. It is that, long after the program is over, they have developed the habit of asking themselves the questions that allow them to keep learning.
Maybe the future of evaluation isn’t simply better measurement of development.
Maybe it is evaluation designed as development.
