An exchange might go like this:

1. Alice e-mails Bob to ask for a meeting to discuss project Foo.
2. Bob's virtual secretary grabs the message and E-mails Bob. The virtual secretary appends information about his schedule and project Foo for Bob's reference. The secretary includes a list of ten times that might work.
3. Bob lists two of the suggested times, a third time, but only if Charlie cancels his meeting, and a fourth which will work but requires cancelling the meeting with Dave.
4. Bob's virtual secretary suggests the first two times to Alice.
5. Alice rejects both.
6. The secretary knows that Charlie's meeting is still on so it suggests the fourth proposed time.
7. Alice accepts the fourth time.
8. Bob's virtual secretary E-mails Dave to cancel and Bob to tell him when he'll be meeting with Alice.

Neil: blatant self promotion is perfectly acceptable if you can solve any part of my time management problem. will certainly give ifreebusy a look.

The desire to meet is usually initiated via an email that proposes the topic/purpose of the meeting and perhaps a suggested time. This triggers the back and forth of arriving at a time that works for everyone. Even assuming the technology is in place, to make the process efficient requires that user take the time to check the schedules of others… this is a change in human behaviour, which is always tougher to achieve than technology changes .

(Warning: blatent self promotion ahead) I ran into the same issues that initiated this blog and setup a simple service for myself and my contacts to use. It hosts .ics and .vfb files and converts between the two formats, allowing Outlook and other client tools to at least have some interoperability. It will also convert .ics/.vfb into a visual representation of your schedule that you can send to others… i.e. "let's meet to discuss this topic, you can see my available time at http://ifreebusy.com/neiljensen/freebusy" It's not a true solution to the calendaring problem; but it is somewhat workable.