If you're going to have a genuine conversation about how to improve communication and your relationship with your manager and to gain a better understanding of

If you're going to have a genuine conversation about how to improve communication and your relationship with your manager and to gain a better understanding of your working relationship with them, certainly. It's fine and often a good idea to have a chat with your managers manager in the instance it's not about a specific issue, but about a genuine desire to improve the relationship. If you're going to find out "why this director is calling out this bullsh*t", probably not a good idea.