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Yea, this one is difficult. I have the same problem when I need to discuss the same issue with two different people. The way I usually solve this problem is that I just assign the context that's further up in the hierarchy (doesn't work if they're not in same part of hierarchy). So if I'm going to two different meetings, I'll just assign the context as "meetings". I know this could get unwieldy if you have lots of meetings.

The other way to think about it is why you're bringing up the task/project in both meetings. Is it really for the exact same purpose? Does one for instance precede the other? Or do you use information from one for the other? In that case, they really are separate tasks.