One approach I have been experimenting with is copied from surgeons: see one, do one, teach one. We have documents and so on, but for novel Devops-ish rocedure

One approach I have been experimenting with is copied from surgeons: see one, do one, teach one. We have documents and so on, but for novel Devops-ish rocedures, I will document it, but then pick some to watch on screen share, then the next time they will drive, and I will watch their screen share, then the next time they will demo to another person. It is great for tasks in between we do it every day” and “we’ve never done it before”. Also it builds confidence (and often the docs are better after the train gets a good writer as the see one person).