"I have to report to my boss on my work every month."
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Yes, you are right. However, depending on the context/conversation, the sentence becomes less specific.
If the sentence excludes 都, then "every month" is being specified generally. It does not exactly indicate that the subject is doing the job all these times. Otherwise, the subject does the job "every single month".
工作报告 is more like "work report" which is a noun, and so is unlikely to be right. However I believe you can certainly say either ...向我的老板作工作报告, which supposedly means giving a less formal verbal presentation, or ...向我的老板做工作报告, which means going through a more complex process of reporting to the boss.
Yes, I'd agree with Goddewyn. Although you could use 跟, and you'll find results for such a phrase if you search for it, it's more common and correct to say that you're reporting to (向) your boss, nor reporting with (跟) your boss.
For interest, here's an example from a blog post on 大人學 (a professional development company): (I highlighted the relevant words)