"Uncomfortable conversations" refers to discussions that make us feel uneasy or awkward. These are often chats about sensitive topics or difficult issues that can bring up emotions or challenging discussions. Full definition
That way you can avoid uncomfortable conversations about what you both want when you're sat across from each other! (tdberyoza.ru)
As I have heard said, a person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have. (entrepreneur.com)
Being upfront and clear about cost can avoid uncomfortable conversations later on. (businessinsider.com)