Whatever conversation you want or need to have, it will not happen if the other person isn’t emotionally ready for it.
You may ask the person if he or she is ready for it. Doing so reminds the other that they can choose and, should they have said yes, that they agreed to this conversation. However, it doesn’t guarantee that that person is ready for the specific conversation you had in mind. How could they?
Take a typical situation of someone asking if a personal question is ok. I’ve often confirmed such requests. And yet, without knowing what the question would be, my confirmation was guarded. Rightly so, as I’ve often been astonished by the subject they brought up and how they did so. As a result, I wasn’t always ready or willing to answer their questions.
This doesn’t mean that such a conversation cannot happen. It simply means that entering the conversation needs to be an opportunity for the other to open up. This is even more important if your idea is to share your view of the situation in the hope that you might be heard.
Open conversations require the other, actually all those involved, to be emotionally available to it. Once this is possible, it becomes important to have a space where thinking can be undisturbed. That is, the thinking needs to be accessible to both and allow for both to remain open to it.