Runbooks, checklists, playbooks, SOPs (standard operating procedures), broadly fall into two categories:
- those that always need to be followed
- those that provide helpful and welcome direction on how to do an unknown or rarely occurring task
It needs to be clear which is which.
An example of one that always needs to be followed is the deployment process. It changes from time to time. The person running it may perfectly remember all the steps from the last time it was run. But this time, a new step may have been added. Reading and following it step by step is critical.
How to keep these up to date? When things break, do a retrospective. Often, the action item required to prevent an issue will require you to update the runbook.
For the runbooks that are "nice to have", you should hear about problems from the people that run them. I regularly hear that such-and-such instructions no longer work, or such-and-such step needs to be changed. People tend to appreciate these types of instructions more as they can see how they make their lives easier. Because of that, they tend to take care of them more.