Andy Grove, one of the founders of Intel Corp. (INTC) and its greatest CEO has been gone since 1998. His company has fallen into deep decline as its place as engine of the PC has become irrelevant. John Young, Hewlett-Packard's dominant CEO has been gone as long. None of the people from that generation of HP management would recognize the company today. Nor would the former heads of Intel competitor Advanced Micro Devices Inc. (AMD) or long-gone Compaq or Gateway.
Steve Ballmer of Microsoft was younger than any of these, but he was in "senior management" at Microsoft in the Eighties and Nineties because his place at the top of the software company was cemented well before he was 30. And, of course, the same was true with Bill Gates who has been retired for a generation already, at least in tech years.
All of these departures have left only Ballmer and John Chambers of Cisco Systems Inc. (CSCO) from the time before the tech industry stock boom of 1999 which collapsed and nearly burned the entire industry to the ground. Chambers has reached was could be called retirement age in the traditional sense, and will certainly be gone very soon. (Steve Jobs belongs on the list, too, He was less successful than Gates and Ballmer at first, and more successful later)
Ballmer, therefore, is last in his class, a fact that many employees and investors regret. But, all the regret can be measured against whether Gates of any Microsoft CEO would have seen the rise of devices no larger than a human hand slap down an industry which was as big and as important as any in the 20th Century. Microsoft's decades of success simply blinded it.
Ballmer and Gates fancied themselves as founders of the internet, as well. To the extent that Windows was at the foundation of the computer, and Internet Explorer of access online, that was true. Legal forces in Europe took those tools away to a large extent. And, as per the internet, Microsoft never replaced them
However, Microsoft persisted to be a central force online. It funded MSN, and its own search tools, which went up against AOL (AOL), whose founder Steve Case is long gone. Along with Case was there was Yahoo!"s (YHOO) founder Jerry Yang the off and on leader until his refusal to accept Ballmer's insistent efforts to buy the portal company injured him.
Not a single one of these companies saw Google (GOOG) and Facebook (FB) slip by them. That will be at the core of the blame leveled at Ballmer more than his failures in hardware (accept the remarkably successful XBox which Microsoft could not morph into a next generation online device) By the time search and social media were huge factors, Microsoft and the companies from its generation, which had survived the tech bubble, had been flanked by more popular products.
Ballmer will leave Microsoft, and along with that tech's old guard will be almost gone. He will be several years short of sixty, retired at a time in his life when most CEOs have just been appointed.