[al_borland]

>he'll start answering with something like, "There are four things I would..."

I've been know to start off replies like that. It's usually that the question is really long winded, so as they say it the issues start jumping out. Then you just kind of keep track of the count until they're done talking and give some space to answer. The hardest part is remembering all the points. If I was smarter I'd jot down a word or two to jog my memory.

Generally these are situations where I know a system really well and the other person does not. So they are saying something like, "why don't we try X", and I either already tried X and just need to list off all the ways in which it failed, or I thought about trying X before, but didn't because of all the ways I thought about it failing. Other times all the issues just seem really obvious, to the point that I can't believe they are talking without hearing the pitfalls.

I may have been the one to post that the other day, I know I left that video in a comment. Another Jobs story on this topic... I saw an article recently with someone talking about how to debate/argue with Jobs. Sadly I can't remember who it was, some other CEO I think. He would go into meet with Jobs and bring up and issue and Jobs would do what you mentioned and give 5 reasons why his idea sucked. Because Jobs' mind worked so much faster than his (his words), he just had to take it and leave. He'd spend the next week thinking about it and formulating his reply. He walk in again and Jobs would respond back instantly. The guy would leave and take another week to come up with his reply... it would go back and forth like this. Eventually Jobs would either finally get his point and say, "oh, you're right", or he'd give up and just tell him to do whatever.