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know how much roadmap-project work people can do in a week. commonly it's 40-60% of their time. call that PR (for Project Ratio).
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make a spreadsheet: [Story, Description, People, Weeks, Person-Weeks].
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break the work down into comprehensible pieces, where you feel confident saying things like "this will take 2 people, working full-time, 3 weeks to implement." in particular, break down milestones that deliver value; where, if the business told you to do something else, that would be okay, and the work done wasn't wasted.
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fill in your spreadsheet columns appropriately (say 2 people, 3 weeks, 6 Person-Weeks).
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sum up the Person-Weeks. ("People" and "Weeks" are for later.)
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Person-Weeks ÷ PRgives you the raw number of Person-Weeks involved (call it TPW). this assumes no technological pitfalls, infinitely parallelizable work, -
TPW ÷ # of people on the teamgives you the minimum amount of time the project will take, as you've laid it out. call it TW. -
you know your people, their skills and challenges, and the environment you're working in. think about delays, known and unknown, like:
- integrating with products or projects outside your influence.
- delays in waiting for other teams.
- staff fluctuations (attritions, planned and unplanned leaves of absence, re-orgs).
- hazy or hand-waving areas in the implementation.
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based on your thinking in #8, and being pessimistic, pick a number from 3 to 10, and multiply that by TW.
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there you go.
"How much gets done in a Person-Week?", I hear you ask from the third row. And the answer is:
I don't know. You have to, if you want to succeed.
Go back to #8. If you have a team of 6 junior developers and 1 SRE, they're going to have a very different "velocity"—call it "productivity" if you're squeamish—than your team of 4 Staff Engineers who wrote the initial product a decade ago.
This really is the core of estimating and planning. Absent organizational overrides, don't commit to something you don't understand. Don't commit to something impossible. (I was once ordered to build something that violated the CAP theorem. It was a bad scene.) Bigger, more elaborate methods are, when they work, ways to gather and track the information of #1-#9.