Here's a conundrumyou might relate to:
1) You have hard feedback to give to a co-worker
2) You keep waiting for the "right time," which never rolls around
3) You don't want to schedule a negative appointment and leave them worrying for the next week
First of all, if this describes you, give yourself a pat on the back for the courage and honesty it takes to give hard feedback and the fact you're willing to do it. That's half the battle.
And it's true--the right time will likely never present itself. Someone else might be around, or you can tell your co-worker's already had a bad day. Or maybe you're having a bad day, and you don't trust yourself to be at your best.
Here's what I do:
Me: Dan, are you available to talk for a few minutes right now? [This is the best option]
Dan: No, I'm just headed into a meeting.
Me: Okay. I'd like to find some time to talk as soon as possible.
Dan: What's up?
Me: Dan, I don't want you to worry, but I've been thinking about what how our meeting went last week, and I have some more thoughts about it. I think our conversation might be a little hard, but it's important to me that we have it. When can we meet?
Giving a quick "heads-up" like this certainly doesn't prevent me or Dan from worrying about the upcoming conversation, but at least he'll have some idea what it's about when he's lying in bed scripting it. If you don't tell people what the story is, they'll make one up, and usually it's the worst version.
How to actually have the hard conversation is a topic for many more blog entries. Stay tuned!