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Blake Irving at the GeekWire Summit. Photo via Eugene Hsu.

One of the recurring topics at Thursday’s GeekWire Summit was the big challenge that Microsoft, especially Chairman Bill Gates, has in trying to find a new CEO.

None of the folks we quizzed — from GoDaddy CEO Blake Irving to former Expedia CEO and Zillow Chairman Rich Barton — wanted the job.

The common theme: It’s a tough job, which got me wondering if there’s really anyone in the world who can take it on. (I’ve argued that Microsoft should actually be looking for three or four CEOs right now to run three to four independent organizations — essentially breaking up the company).

One thing we’ve heard is that Microsoft co-founder Bill Gates is taking a very active role in the search, looking hard for someone who can lead a complex organization that has fallen behind many of its rivals.

GoDaddy CEO Blake Irving, who was on The Wall Street Journal’s short list of potential candidates, said he laughed out loud when he saw the report.

“I literally guffawed,” said Irving.

“That’s a tough, tough job,” said Irving, who worked as a corporate vice president at Microsoft from 1999 to 2007. “All of the guys that I have a tremendous amount of respect for, whether it is Kevin Johnson or Paul Maritz or Stephen (Elop) — they are all good guys that could do the job. It’s a tough gig.”

I jokingly asked Barton — a consummate entrepreneur — if he’d be in the running (based on a GeekWire reader who keeps floating his name in the comment threads).

“I found out over the years that I give direction, better than I take it,” said Barton, who successfully spun off Expedia from Microsoft in 1990s. “And, I think the next CEO is going to have to be able to do both.”

Silicon Valley venture capitalist Bill Gurley, who joined the stage with Barton, said the Microsoft CEO question was one he kept hearing ever since landing in Seattle.

Rich Barton and Bill Gurley at the GeekWire Summit. Photo: Eugene Hsu.

“I think entrepreneurs … in general don’t pay enough respect to how hard it is to run a really large company,” said Gurley. “It is probably the most difficult thing you can possibly do as an executive. So, when I see things, like what John Donahoe has done at eBay: ‘I am like, wow.’ We should all really praise, because I think it is just that hard. And I think the Microsoft situation will be like that to try and take something that’s in its current state where it has a lot of disruptive competition coming at it — what I once again call orthogonal competition (meaning) they are not playing the game the way you were.”

He then said Microsoft would probably have to buy eBay in order to get Donahoe.

HBO CTO Otto Berkes, who worked on Xbox and Bing during his Microsoft tenure, said he didn’t really have a frontrunner in mind.

“It’s no doubt an incredibly demanding position,” he said. “My personal bias and background would like to see somebody with business acumen, but also very solid foundation in technology and product development.”

Berkes said the Microsoft break-up theory is one idea that has been floated, and he noted that Microsoft could come up with a “number of different arrangements” that could make sense. “I think it is going to depend on who the CEO is, frankly. Because some of the alternate configurations may make sense for one leader, but may not make sense for another.”

Irving also addressed the break up concept, when he was asked by GeekWire’s Todd Bishop what Microsoft should do next.  And he summarized the big challenge in front of Microsoft.

“Oh, my god. Who knows? I think it is easy to malign Steve (Ballmer), and I think there has been a fair amount of that. He’s got a tough job. That is a giant company. He had some decisions to make — whether he splits the company up; whether he keeps it together; does he let businesses run more autonomously; does he become the hub in a hub and spoke model and become the group program manager of the company. He had a lot of different decisions to make, and he decided to do it one particular way. And there’s lots of other ways he could have done it. Who knows if any of them could or could not would work or would change the trajectory that the company is on. The guy has done an amazing job returning earnings. He hasn’t affected stock price, which I think is more of a factor of the hope co-efficient than anything else. Anybody can second guess. It is very easy to do it. But, to actually get a company of that size on a trajectory that changes dramatically the positive slope of that company is going to be pretty difficult. I’d hate to say that I’ve got an answer for you that’s going to do it.”

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