"This is not going to be a fun conversation."

This is how I had to start a conversation today. Bah Humbug!

It was a conversation I didn't want to have, I had to take a position I didn't necessarily agree with (but could see the reasoning) a conversation I had fought against having to have (I lost), but a conversation I had to have nonetheless.

There was a business decision made by the business which I had to carry out.

It was probably easier for me than the person I had to talk to. It wasn't fun for anyone.

So, would you prefer to hold this conversation before or after the holiday season? Allow someone to waltz through without a concern (and potentially over spend) or lower the boom before it? Thoughts?