You'll have situations like this everywhere. 1) You think that the current system is untenable and the only way forward is to refactor according to your plans.

You'll have situations like this everywhere. 1) You think that the current system is untenable and the only way forward is to refactor according to your plans. 2) Your manager thinks refactoring is going to take a long time or might even break a system that works. This is as much a social problem as a technical one. It's a problem that you aren't going to fix in one meeting. You need to work on getting to the same page. Some possible approaches: - Make your manager aware of the problems that the current build system is causing. Make sure your manager actually knows about it when a dirty build environment causes an issue. - Try to understand why your manager resists the change. Is he afraid that lots of people will need to learn a new system? Does he worry that a new system might break in other ways? Does he think refactoring is wasting time needed for other projects? - Be open about possible solutions. Don't focus on a specific solution like Docker, focus on the problem instead. If the problem is a dirty build environment, maybe a script that cleans up the build environment might have similar benefits, with less risk? - Try to find solutions together instead of choosing between my solution / your solution.