I found this on Computerworld's Shark Tank and thought about the old "Who's on First?" bit. It's also a great example of trying to understand the users' true needs and expectations of software.
"He (Big Boss) wanted me to help him understand how Microsoft Outlook calendar appointments work with changing time zones," says fish. "I updated the online docs, then walked down the hall for the explanation to the big boss."
But as soon as the big guy hears the explanation -- how Outlook will automatically reflect the time-zone shift when the clock is changed -- he tells fish, "No, that's not what I need. I need to be able to set an appointment up for a certain time slot in the other time zone for next week, but then appear in the same time slot when I look at it with my PC set to my current time zone, this week.
"If I set it for 2 p.m. there, then it needs to show up as 2 p.m. on my calendar when I look at it from here, but for next week.
"And I want everyone else invited to the meeting to see it correctly when viewing both here and in the other time zone. And, oh yeah, it needs to show the correct time slot on my smartphone calendar, and on all the attendees' smartphones, next week when we're traveling."
Fish scratches his head and then attempts to explain that an appointment set in the other time zone will always appear in a different hour time-slot when viewed from a device set in the current time zone, and that it all depends on the time and time zone set on the device.
Big boss says, "No, you're not getting what I need. I need to be able to set an appointment up for a certain time slot in the other time zone for next week, but then appear in the same time slot when I look at it with my PC set to my current time zone. I can't believe that there isn't a way built into the software to do this!"
Reports fish, "I tried to explain it one more time, but in the end the big boss looked back with glazed-over eyes and said, 'Well, since the technology can't help me, I'm just going to print out my calendar and carry it with me to the other time zone.'
"Then he proceeded to print out next week's calendar on paper."