We tell leaders to “delegate and elevate” all the time. But when someone is buried in deadlines, doing work only they know how to do, and trying to keep everything moving, that advice isn’t particularly helpful.

In this experience share, I talk about a coaching conversation with an operator who knew she needed to get out of the weeds but couldn’t see how. The answer wasn’t to magically stop doing the work. It was to get practical: handle what had to happen now, identify what could be taught, schedule the time to teach it, and give her the tools to make that transition happen.

Sometimes leadership development is less about telling people what they should do and more about helping them figure out how to actually do it.