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You should either go for this one first or last. When you do this, you'll get "fired" and your office will be reset, causing you to lose all of your collectibles.*

This is one of the most fun, stress free achievements to get in the game. Keep pressing the bucket machine until you get bloody limbs. Leave buckets everywhere. Get your mop dirty and paint the level with blood. Just have at it, make the biggest mess you possibly can and then exit the level. The game will give you a hilarious "The Union will have my back." option and you'll get a note saying you were fired for doing an abysmal job.

* You can look up where your office files are stored and revert to a pre-failure version of it.