So many of my clients ask me what they should do with difficult conversations they are putting off.
The first thing, should be obvious. Stop putting them off, it's not helping.
From there, they tend to feel woefully unprepared. Which is weird. These are incredibly smart people, capable of doing things that others find impossible and yet they are worried they can't have a conversation? No. The reality is they are afraid of something else. Ruining a relationship, losing an employee or client, or just afraid of the fact that they don't know how the other person will react.
Here's a hint: Their reaction is not your responsibility. You are responsible for communicating your needs clearly and politely, but if they can't converse back, that is not your problem to fix. Stop trying to control what you cannot control. Sure, have an idea of the few options where they might go so you can be prepared, but in the moment, make sure to listen and respond to what they actually say or ask, not what you thought they would say.
Honesty is always the best policy. Are you two on different pages? Say that. Does it feel like they don't understand what you are asking them for? Say that. Are you both in an impossible situation? Admit it. Only by agreeing on the problem, can the conversation actually move towards productively finding a common solution that will work for both of you.
So stop hesitating and get to talking, now.