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Python developers won’t let go of Python 2
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The trick is to assign someone the responsibility of the upgrade and give them the authority to tell the other developers how their newly added code shall look like. This will get you there eventually.
Seen it work on a >1 million SLOC project.
Yeah but that requires good planning and better team structure.
That's low margin and therefore doesn't happen often enough.
Only if you can actually upgrade piece by piece. In a monolith, you often enough can't just upgrade new lines/methods. In those cases, it's halt all development, pull everyone into upgrading and then continue.