Those long family road trips my dad used to take us on felt both exciting and interminable. Somewhere along the way, my sister and I would inevitably pipe up from the back seat: “Are we there yet? How much longer?” We had no way to assess our progress except to pester Dad every twenty minutes.

I thought about that recently at a conference in Canmore, Alberta, with fellow consultants and coaches passionate about building leadership capacity and fostering healthy cultures where people feel respected, heard, and that they matter. One question kept surfacing across different conversations. It wasn’t about the latest frameworks or training plans. It was more fundamental: how do organizations actually know if any development investment is making a measurable impact?

Without a clear way to track progress, you end up in the same position my sister and I were in, hoping you’re heading somewhere worthwhile, with no way to know how close or how far you are.

Most of us have also had the post-workshop experience that makes this personal. You leave feeling fired up and invincible. Then you get back to your desk, the enthusiasm quietly dissipates, and the day-to-day heap takes over. You wanted to do something differently. You just lost the thread of what that could actually look like.

The real gap is behaviour change

With AI at our fingertips, knowledge and content is more accessible than it’s ever been for leaders looking to support their teams. The real gap is behaviour change: what actually helps people adopt the actions and behaviours that move the most important priorities forward. How do you sustain those changes reliably, especially when the pressure and stress is on?

Most development programs aren’t designed to answer that question. They invest in the content and hope the delivery in the room is good enough to make a lasting impact. Success and ROI is “measured” by tools like feedback forms, engagement surveys, and watching over months whether learning and development investment dollars were able to “move the needle” meaningfully going forward. The reality is that these kinds of tools are too slow, highly subjective, and provide you with a retrospective evaluation of whether an initiative to improve performance or culture actually works. The opportunity to course-correct has already passed, so you have to come up with a new intervention.”

People absolutely learn from good coaching and facilitation. Without a real-time feedback loop, though, neither the leader nor the people working with them can see whether that insight is actually translating into different choices. That’s a structural problem, not a content problem.

The missing link: measurement

H. James Harrington put it plainly: “Behaviour change doesn’t happen in a single session. It happens in the ordinary moments between sessions, when no one is watching and the defaults are pulling hard. Consistent practice over time is what builds the new pattern you want to see.”

For leaders, the only question worth asking is whether you are actually making different choices in the moments that matter, and whether you can see that change happening in real time.

Organizations routinely measure the return on financial investments: revenue, cost savings, margin. When it comes to leadership development, measurement often stops at attendance and satisfaction scores. That is the equivalent of measuring a road trip by counting the rest stops. It tells you something happened. It does not tell you whether you arrived.

Behaviour change doesn’t happen in a single session. It happens in the ordinary moments between sessions, when no one is watching and the old defaults are pulling hard. Consistent practice over time is what builds the new pattern.

Whatever program you have, design with the end in mind. Having intentional scaffolding and support that sustains the willingness to adopt the change, and uncover what is still in the way of that which needs to be address, helps to ensure that the initial participant commitment to apply new insights to how people can do their best work needs to extend beyond the session itself. Otherwise those trainings, workshops, coaching sessions, and offsites intended to improve performance and build strong alignment end up being expensive ways to essentially throw spaghetti on the wall and hope it sticks.

It is for this reason that, with my clients, I use a habit builder tool that helps them focus on the one behaviour change that matters most, practise it deliberately, and track their progress in real time. This allows me to then provide real-time feedback to support and accelerate their process.

Information without application isn’t useful. Measurement is what closes the gap between the two. The question worth sitting with, before investing in any program, is a simple one: how will you know when you’re there?