[kokokokoko]

My rule has always been: "write down the entire manual process". Follow the steps and do a deployment and time it. Do you have that much time? Are you likely to make an error? If not, just do it manually. If so, break out the easiest parts and automate that. Then reassess.

Automation should follow the same rule as other things in a business. Only automate when it becomes painful not to. Or if it is trivially simple to.

[rakoo]

Reminds me of an article I saw sometime back on HN: "Manual work is a bug" (https://queue.acm.org/detail.cfm?id=3197520). Just like you, the author's advice is to go iteratively, with the first step being documentation. As documentation improves you act more as a cpu running instructions, at which points automation becomes clearer, and so on. Not everything can or should be automated, but we definitely could do more.