Top 10 embarrassing executive mistakes

Mistakes we love to savour in the IT world

Mark Hurd's ignominious departure from HP came too late for a Top 10 list last week, but we hope to make up for it this time around.

We've all had those moments when we suddenly realise that we shouldn't have done that but, if you're the chief executive, the results of such a slip are much more profound.

Gerald Ratner made one of the biggest goofs of the century after describing his own products as "crap", but in the technology sphere we're looking at more geeky mistakes.

There was long discussion about including the AOL/Time Warner merger in the list, but it got excluded because the two chief executives did very well for themselves, even if the shareholding public didn't.

Similarly Intel's reversal on processor identification or floating point errors aren't on the list as some people get the message and learn from their mistakes.

But the mistakes we've included, in fun and seriousness, are those that changed the fortunes of companies and the whole industry.

Honourable Mention: Steve Ballmer's crazy keynotes
Shaun Nichols: Few executives have the penchant for creating YouTube moments like Steve Ballmer. Just about every time he takes to the stage you know someone will walk away with an amusing clip, and almost none of them are good for Microsoft.

One particular problem is that Ballmer is a rather excitable person (to put it mildly). When he gets on the stage he tends to do things like dance or go on verbal tirades. Entertaining, yes. But I'm sure Microsoft executives cringe at the thought of their company being associated with the developers scene.

He has got better in recent years. At the 2010 CES conference Microsoft had several demos in its keynote address fail. While you could almost see the veins popping out on Ballmer's neck, he did a remarkable job of keeping his cool in a very stressful situation.

Iain Thomson: I've a certain fondness for Steve Ballmer. I suspect that he's smarter than he lets on and plays up the manic role because he sees the advantage. Having a boss who reputedly throws chairs around the office can be a sobering experience for staff.

But some of his antics have stretched the bounds of what chief executives should get up to in public. I still regret the failed pact to sing Do the dance! at the Windows XP launch among the UK press corps, but if we had he would have taken it in good spirits.

Steve may have given us some good fun over the years, but it's easy to dismiss him as a used car salesman who got lucky. Ballmer was at Harvard, got convinced by Bill Gates about the computing industry, and then borrowed to the hilt to invest in Microsoft stock.

As a result he's one of the richest men in the world, and I suspect a few million YouTube hits don't bother him that much.

Honourable Mention: Bill Gates and CES crashes
Iain Thomson: Bill Gates gave up his keynotes at CES a couple of years ago and, based on his record there, the move must have been a blessed relief.

Bill's not great at demos. Occasionally he'll pull off a great performance, but usually things go wrong, badly wrong in some places. Many connoisseurs relish his blue screen of death moment in 1998 when he showed the audience just what an irretrievable failure in Windows 98 looked like.

For me, however, the classic moment came at the 2005 demonstration of Media Centre, when not one but two failures kicked in at just at the wrong moment.

Conan O'Brien, who had been hired to show just what a fab and groovy guy Bill really was, started cracking jokes about people at Microsoft getting fired as Bill got increasingly frustrated at the scale of his demo disasters.

Shaun Nichols: A more cynical person would suggest that the apparent failures were in fact just reflections on the quality of the products Microsoft was putting out in those days.

CES keynotes have been something of a curse for Microsoft, and Bill Gates specifically. The company has suffered embarrassing breakdowns of such scale and frequency that one has to wonder whether Steve Jobs isn't hiding in the back of the hall frantically jabbing pins into a voodoo doll.

Part of it is just the chaos of CES. With literally thousands of companies presenting at the show and the biggest names in their industries all giving presentations, things are going to fall through the cracks.

There's also scheduling pressure, as Microsoft often has to push incomplete or untested products in order to be ready for the CES stage.