Hi Mohamed – thank you for your question. In the advice I provide, I mention that you should address the one issue that matters to you the most. If that issue is that your boss is sharing important information that he shouldn’t be, then yes, speak up about that specifically. The point is not to pile on all these complaints in one conversation. If you’ve waited this long to speak up, then you’ll have to take the path back to resolution slowly. It’s more incentive not to wait to hold Crucial Conversations in the future. But at this point, yes, I recommend starting with one concern and that could certainly be that he must be more discreet in what he shares with others – especially if it’s violating confidences, policies, etc. Hope that helps.