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No that’s the problem. The riskiest bits stay risky forever if you tackle them before you understand how. Junior people or new problem domains require exploratory development before committing to a strategy.

In an 18 month or three year project, it doesn’t affect your deadline much if you do the hardest bits in month one or month four. Except in how much rework you end up doing to those parts that have already started to cement bad habits.

When we have a Rule of Three situation in the product backlog, I usually recommend one of two strategies. Do the hardest one second, or do it third and allocate very little time for the first two - you’re going to rework the whole thing when you get to #3 anyway.

On one project, no matter what order we did them in, the third one took the longest time. Even when we tried to take our time on the second. Took me a year to train them to stop doing that. I’ve never seen a team so sure of their abilities yet with such a low opinion of their product. Big ol’ echo chamber.




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