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Microsoft (MSFT) has been taking some hits lately. Sales of Macs have been going up faster than the sales of PCs as a whole. Vista, Microsoft's latest operating system, has had a host of problems since it was introduced in early 2007.

Not that Microsoft has suddenly turned unprofitable. Last year the Windows group made $13 billion.

But there are those Mac versus PC ads that skewer the giant from Redmond and are fun to watch, not matter what kind of computer you use. Last month Microsoft announced that it was going to fight back with ads of its own.

On August 21, the Wall Street Journal announced that "Microsoft Corp., weary of being cast as a stodgy oldster by Apple Inc.'s advertising, is turning for help to Jerry Seinfeld." Last week the ad debuted. You can see it on YouTube by clicking here.

Microsoft has a problem. This ad campaign is going to cost $300 million, which isn't much of a slice of the $13 billion, but it is a simply awful bit of advertising slop. I've now watched it several times and I haven't got a clue what the message is supposed to be. The word "Vista" is never mentioned.

Microsoft has a problem. If portraying yourself as something besides a stodgy oldster is your goal, this isn't the way to do it. Gates and Seinfeld are in their fifties. Jerry's show has been off the air for a decade. Even that might be OK if the ad was funny. It isn't.

Microsoft has a problem. Jerry Seinfeld the person is mostly identified with Jerry Seinfeld the character. And, according to Todd Bishop who writes the Microsoft blog for the Seattle Post-Intelligencer, "fans of the 'Seinfeld' television show quickly pointed out that Jerry would often have the latest Apple Macintosh in the background of his apartment.

This strikes me as the kind of problem leaders create for themselves when they only talk to each other. I have to wonder if a single Mac user was part of the conversation, or anyone under the age of 30.

Wally's Working Supervisor's Support Kit is a collection of information and tools to help working supervisors do a better job. It's based on what Wally's learned in over twenty years of supervisory skills training. Click here to check it out.

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Wally Bock has helped people learn to be great bosses for more than a quarter century. His latest book, Performance Talk: The One-on-One Part of Leadership, makes learning key leadership principles almost effortless by teaching through a story and providing lists of resources for further growth.

Click here to find out more about Wally's coaching services.

For weekly tips and resources pointers, check our Wally Bock's Three Star Leadership Letter.

Click here to find out more about having Wally speak to your company or convention.