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The revolving door in the CIO’s office can’t help Kmart in terms of continuity on its supply-chain projects. At some point, talented people ask themselves if signing on as the sixth CIO in seven years is a wise career move.

“Good candidates will ask what’s wrong with a position that stays unfilled, or turns over often,” says John Koopman, a partner with search firm Heidrick & Struggles in Toronto, in assessing situations similar to that faced by Kmart. “No good executive wants a one-year assignment, even for a lot of money. That doesn’t further anyone’s career.”

The highly regarded CIO of one national retailer is more blunt: “They could certainly find someone in between jobs that would take it, but I doubt that anyone would leave a good job.”

Plus, at Kmart, revolving doors seem to abound. On Nov. 9, Kmart announced that CFO Jeffrey Boyer, brought in from Sears, had resigned after only six months on the job. Earlier this year, chief marketing officer Brent Willis, brought in from Coca-Cola, departed after four months. Andy Giancamilli was appointed president and chief operating officer in July 2000 by CEO Chuck Conaway, and resigned in March 2001.

The current CIO search began when Randy Allen was reassigned from the post in August. Big-time jobs like this one commonly take several months to fill, although two vacancies ago, it took Kmart more than a year to name a new CIO.

Of course, money can talk. Chief operating officer Mark Schwartz, who succeeded Giancamilli and is overseeing some of the IT effort, received almost $4 million in compensation last year. And there also would be the glory of turning around Kmart, after decades of trailing in technology.

One search firm executive says he would recommend going after an experienced CIO who was willing to try for “one last hurrah—five years and take the money.”

CEO Conaway, who received $14.2 million in salary, bonus, and other compensation last year, may be the guy to bring in the talent.

To replace Boyer, he promoted John McDonald, whom Conaway brought over from CVS where the two had success building one of the nation’s top pharmacy chains.

Conaway’s own lack of experience in a chief executive spot reportedly gave pause to some on Kmart’s board, but his strong personality and his track record at CVS—engineering acquisitions that made it the second-largest drugstore chain—won over the skeptics. But success can be fleeting. Disappointing third-quarter numbers at CVS caused its stock to drop 23% in one October day. The company said it will close stores and distribution centers, and improve service.

Conaway makes himself highly visible to his IT staff, frequently appearing at departmental meetings-cum-pep rallies that are held at least once a month. And when he isn’t there, Schwartz is, firing up several hundred people as music blares in an auditorium or cafeteria. “It’s informational and it shows that he truly supports our group,” one Kmart insider says.

Also part of the boss’ modus operandi: Leaving a company-wide voice mail each week to update people on good news and bad.

Conaway, 40, who has regaled the media with tales of bow-hunting exploits in Africa, may lure a CIO through this kind of adeptness in pumping up Kmart’s staff at the same time he shakes up its promote-from-within culture. “He’s a good inspirational leader,” says one IT-department insider at Kmart. “IT is getting more of a focus on having a world-class organization that will be customer-centric, as opposed to a bunch of techies sitting in the basement.”