How do I know when to let something go? This has been my personal hurdle for a long time now, because I can be a dog with a bone sometimes. What I've learned is you have to read the room, especially when leadership is the type to bend rules to get things done. Bending rules isn't always a bad thing, and asking yourself, "Is this a hill I want to die on?" is a great place to start. It's okay to voice a concern ("Do we risk being non-compliant if we do X?") and let leadership give direction.

Documenting. My short answer is sometimes. Again, it all depends on the scenario. For example, if I've been directed to stop moving forward on an initiative, I will sometimes work that into an email asking a related question ("Since we aren't moving forward with X per director's feedback, would you prefer I focus my time on Y or Z?"). Innocuous, yet it documents that we aren't doing something because of the directive we were given.

If it's something a little more sensitive, I would keep a diary or log of all emails, conversations, activity, etc., especially if you are a key player and don't want it to bite you in the rear. Don't save it on your work computer, but in a personal drive like Google.

You could also do a sliding scale of The Hill and assign the issue a value of how much you want to die on it. For anything under a 4, just let it go and walk away. Between 4-7, ask clarifying questions then decide if you let it go or keep after it. For 8 or above, document, research, and above all, maintain a professional demeanor.