Why is this hard?

No arguments here. I’m honestly not even convinced there is any “engineering” involved, but we’d probably have to knock a couple of zeros off of our paycheques if we called ourselves “systems artists.”

There is actually a bunch to unpack in the rest of your post which would result in me probably writing a blog-post length of stuff, so I won’t, but:

This is a super important point. Many people get disillusioned by processes because a) at first they don’t work immediately and hinder more than help, and b) many orgs don’t take the time to properly teach their teams how to do this stuff or even understand it themselves (in which case they just continue to not work and be a hinderence).

That link does a good job of explaining, though I think it works extra well with estimates (and is even a bullet point on “A Case Against Estimates” linked above). Perhaps people would feel uncomfortable saying this out loud but it’s “Under promise and always deliver on that under promise.” This manages everyone’s expectations, leaves a lot of room for the unexpected, leaves room for experimentation and tech debt, and generally keeps everyone—including leadership and customers—happy.

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