TallSky Executive Coach and HR Associate Meredith Campbell-Jess shares her thoughts on how to make thoughtful, well-designed training stick. You can also follow more of Meredith’s fabulous writing on her Substack.
I spend a lot of time with teams talking about learning and development. Often, the conversation starts in a familiar place. What training do we need? What program should we run? What are other organizations doing? All good questions. And to be clear, I believe in training. I’ve seen how powerful it can be when it’s done well. It builds shared language, strengthens capability, and creates real momentum.
But I’ve also seen something else. Some of the most thoughtful, well-designed training doesn’t always stick. Not because it wasn’t good. But because what happens after matters just as much as what happens in the room.
Training starts it. What happens next determines whether it lasts.
In the organizations where learning actually sticks, there are a few things that feel different.
It shows up in everyday conversations
It’s not just in workshops. I see it in team debriefs that pause to ask, “what did we learn?” not just “what happened?” In check-ins that go beyond tasks and make space for growth. In leaders who ask more questions than they answer. Nothing about this is complicated. But it is consistent.
Leaders don’t feel like they have to have all the answers
This one comes up a lot. In some teams, leaders feel pressure to fix, solve, and move things forward quickly. It makes sense. It’s efficient. It keeps things moving. But over time, it also creates dependence. In the teams that are growing, leaders take a different approach. They slow things down just enough to listen, to explore, to let others think it through. It can feel less efficient in the moment. It is much more effective over time.
Feedback is part of how people work, not something separate
In strong cultures, feedback isn’t saved for performance reviews. It shows up in small, timely ways. Clear. Specific. Useful. People know what’s expected. They know where they’re doing well. They know where they can grow. That clarity changes everything.
The environment actually supports learning
This is the part that often gets missed. I’ve seen organizations invest heavily in training, while at the same time expecting people to move faster, do more, and leave little space to reflect. It’s hard to build a culture of continuous improvement in that kind of environment. In the teams where it works, there is alignment. Leaders are recognized for developing others. Learning is shared. There is space to try, adjust, and improve.
Culture is shaped by what gets supported, not just what gets said.
Keep it human
At the core of all of this, people want to grow. They want to feel capable. They want to contribute in meaningful ways. Training can spark that. But it’s the day-to-day experience of work that determines whether it continues.
Final thought
I don’t think the question is whether training matters. It does. The better question is what happens after. Because a culture of continuous improvement isn’t built in a session. It’s built in conversations, in leadership moments, and in how teams show up every day. That’s where learning becomes part of how work gets done.
How TallSky can support
At TallSky, we spend time on both sides of this. We design and deliver practical, engaging training. And we work alongside leaders and teams to help that learning carry into everyday practice. Because the goal isn’t just to learn something new. It’s to work differently because of it.