After leaving Microsoft in 2001, Brian MacDonald found it tough to find his second act. He was involved with a few start-ups and arranged some real estate deals in the Seattle area. He even built a boat in China.
But none really offered the challenge he was seeking. So, when he had a meeting in February 2007 with Microsoft search boss Satya Nadella, he was inspired. That night, he went home and cranked out a 10-page paper on the challenges and opportunities he saw for Microsoft in search. It was in Nadella's in-box the next morning.
"I just want to work on the biggest problem in the industry," he said. By April, he was back at a desk in Microsoft's Redmond, Wash., campus.
MacDonald could hardly have found a bigger task than entering the search fray. After three years in the search business, Microsoft had yet to make any significant headway despite having spent billions of dollars.
"Search is kind of the Mount Everest of the industry right now," he said. "That's really the mountain that you want to climb."
He's been back at the company two years now, and Microsoft still finds itself at base camp, struggling to reach double digits in market share and its online business is losing hundreds of millions of dollars per quarter.
But Microsoft hasn't given up on its expedition. This week, it takes an important step. After months of testing within Microsoft's walls, the software maker is publicly detailing its plan to revamp its search engine under the name Bing.
The update consists of a new look, a new name, and new capabilities for the product. And in the process, Microsoft hopes it will also get a fresh start in what has thus far been a painful journey.
Several of the features are things championed by MacDonald. In particular, the new engine has a left-hand navigation pane for moving among different types of searches. Bing also breaks a search query down into a number of possible categories.
When one hovers over a particular result, they get a pop-up window with more information, such as the query terms in context on the page.
In other cases, Microsoft is bringing more information into the results themselves. Type in "Amazon" and one will get not only links to that Web site, but also the company's hard-to-find customer service phone number. A search for UPS will let one track a package directly from Bing.
While potentially useful for customers, it could also be a sticking point among those whose content it is borrowing from so liberally. Product searches, for example, aggregate both user and professional reviews from various sites directly within the Bing result.
"I don't think we are trying to do something unnatural to have the person stay within the site," MacDonald said, adding that in the end the company thinks it will drive more people to the pages it is indexing.
With Bing, Microsoft also makes its interface more similar when one moves among different types of searches, such as photos or news. It's not unlike the way Outlook has some common interface tools that remain consistent even when a user switches from calendar to contacts.
"You get a different tailored experience but you still feel like you have stayed in Outlook," MacDonald said. "That's very much the integration model we have been going after."
Perhaps the biggest thing, though, MacDonald said, was the fact that the new design is opened up to allow more innovation down the road, as opposed to the classic search page with its single page of generic results.
"The 10 blue links alone makes it hard for an engineer to have that brainstorm in the shower," he said. "You need that extra surface area."
In one example, Bing now allows full articles to be shown within the search engine both for Wikipedia articles indexed by Powerset as well as for health topics, using content licensed from the Mayo Clinic.
In choosing MacDonald, Nadella said he admired the way that he could see opportunity where others saw mature markets. His approach with Outlook particularly resonated with Nadella.
"E-mail existed, calendaring existed, and contacts existed," Nadella said. "He changed the way people interacted with those applications."
Tapping MacDonald meant dealing with someone very unlike himself. In contrast with Nadella's neat desk, MacDonald's office is so cluttered his assistant was once asked if it was an office or a store room.
"We're different," Nadella said. "I don't work like Brian."
But creating some difference was an important cultural shift that needed to occur, he said. "Out of that will come the creative breakthroughs," Nadella said.
One of the big debates was on another of MacDonald's ideas - putting a picture in the background of the main search page. Each day, Microsoft has a different photo on its search page. It's designed as the kind of thing to get someone to check back each day, but some inside Microsoft saw it merely as a graphical distraction that slowed page load times.
Bringing back MacDonald was just one part of Nadella's strategy. The other piece was creating a deep science background to replace a culture that had been based on marketing other people's technology. To lead the effort, he convinced Harry Shum, the head of Microsoft research Asia, to join the search effort.
"He brought about that change in our engineering." Nadella said. Early on, the company's ranks were mainly filled by folks from research or other parts of the company. "Lately, of course, the Yahoo parade has been great for us," Nadella said.
As pleased as he is with some of the changes, Nadella's goals appear to be rather modest. If Microsoft were to go from 9 percent share to 11 percent by next year, he would consider that a success.
"I would say those are great gains," he said. "It's not a share battle that is going to go from 8 or 9 (percent share) to 20 in a quarter."
For his part, MacDonald said he wasn't always sure he wanted to go back to work at Microsoft. He said that he had long had thoughts of how the company could win in search, but added "I wasn't always sure the company was ... fully committed."
These days, he is more convinced - sure enough that he sold that boat he built in China.
"It was, literally, a slow boat from China," MacDonald said. "It took days to get anywhere. It wasn't really compatible with the time commitment I need in this job."