Questions for Steve Jobs

Matthew JC. Powell
27 April, 2008
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In this week’s bumper edition of the Australian Macworld Weekend Edition Podcast, Keith White interviews Adam Engst — of TidBits and Take Control e-books fame — about how he got his start in computing and when he became a Mac devotee. In amongst the discussion Engst makes an interesting observation: that despite being a Mac community "A-lister" he’s never had an actual discussion with Steve Jobs and, most interestingly, that if he did get the chance he doesn’t know what he would ask.

It’s quite the revelation coming from Engst, who has been reporting on developments in the Mac scene for nearly twenty years. Most of us probably have much the same fear: if we actually found ourselves talking to the CEO of Apple, would we become tongue-tied and not say anything? Would we ask some lame question that makes us look like an idiot (and Jobs does not tolerate idiots)? Or would we come out with a brilliant and insightful observation that earns the immediate respect of the Insanely Great One?

Most of us, of course, aren’t Adam Engst. I would expect Engst to be able to come up with a decent question if he ever met Jobs, and it’s maybe even a little reassuring to me to find that he doesn’t think so.

I’ve met Jobs on two occasions. The first was at a party Microsoft held during the Macworld Expo in San Francisco in 1998. I have a vague recollection it may even have been the launch of Office 98, but I’m not 100 per cent sure. At any rate, I noticed Jobs over at one side of the room and went over to say hello. However, I made trhe mistake of failing to identify myself as a journalist (at the time I was with Australian Reseller News). After a few moments of idle chit-chat about the party and how interesting it was to see him there, he asked me where I was from. At that point I mentioned my profession and he turned on his heels and walked away, without another word. I suspect he thought I’d been trying to trick him into an ad hoc interview. I hadn’t been, but he wasn’t to iknow that.

The second time was at the opening of Apple’s SoHo store in New York in 2002 (again, during the Expo). This time I was wearing my media badge, so there was no mistaking who I was or why I was there. I approached Jobs with Garry Barker from The Age, and Garry asked him if he would mind if we took a photo. He said he was "all photographed out" so we put our cameras away. Then a little small talk about what a cool new store it was, and someone else spotted Jobs and made their way in to have their turn.

Neither of these really counts as the kind of conversation you tell your kids about. My kids are young, so they don’t know the difference, but if I recount the story sometime when they’re too old to be impressed by funny voices, I don’t expect it will hold their interest.

The problem is, on neither occasion did I have anything really "good" prepared. If it had been a proper formal interview I’d have prepared some questions pertinent to whatever occasion had compelled Jobs to give an interview. Bumping into him at a party and in a shop, I was not prepared.

As Engst points out in his interview with Keith, it can be tricky to know what to ask Jobs. On the one hand, he doesn’t like talking about the past, so unless you’re in a very specific pre-ordained setting for doing so (such as his onstage appearance with Walt Mossberg and Bill Gates last year) there’s no point asking him about the good old days with Woz. He’s too focussed on the future.

On the other hand, he doesn’t talk about unannounced products, so the future can be a tricky subject area as well. If you happen to ask him about something that Apple has imminent, you’ll get no answer. If you stumble onto an area in which Apple doesn’t have an imminent product but is making vague plans, you’ll likely get him talking down competitors.

Which leaves really only the present in which you can get a reliable answer out of him. So you talk about how it’s interesting to see him at a Microsoft party, and isn’t this a cool store we’re standing it right now, the two of us, you and me, in the present.

I’m going to throw this one over to you. If you bumped into Steve Jobs in the street, what would you ask him? Would you ask about how to restart your iPod? Where does he get his turtlenecks? Would you ask about upcoming Pixar releases? Or would you have something better to say?

For that matter, what would you tell him. If you had one minute to pass on a bit of information that you thought Jobs ought to know, that might make you stick in his museum of recollections as someone with something interesting to say, what would it be?

I look forward to reading your responses in the forums.

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