One thing that I find asking at lot of work is "who is the audience?". I find that it helps to eliminate possibilities for how work can be done. E.g. "let's document something in the issue tracking software so we can easily use it" - that doesn't help if the consumers of the info would never use the issue tracking software (upper mgmt) and they just want an executive summary. Figuring out the output first makes it a lot easier to determine what the input should be.
I found myself making this mistake yesterday with a different kind of situation. We had some family over for a bbq and I decided that we'd serve some watermelon. I tried my hand at trying to carve it like a pretty flower. After watching several demos online and then creating a product that looked like a drunken monkey took a weed whacker to it (but everyone said it was nice), it was put on the table. No one touched it. Not even myself. It could be a case of too much food, but I think that it was just in the wrong format to be eaten at the bbq. I should have just quartered and sliced it. Fancy carving - dinner party. Brunch - melon balls. BBQ - slices.
When making it, I was thinking of first step. I should have thought of the last step and worked backwards. If you don't know where you're going, any path will take you there.
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