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Fulfilling a second major part of its promise to make the internal workings of its Web site more extroverted, Yahoo is opening the interface for its address book for outside use.

The move could mean that Yahoo, struggling under business pressures but still a stronghold of Web activity, could become more tightly tied to others' Web services. For example, a programmer starting up a social networking site could use the interface to send invitations to a member's list of contacts stored at Yahoo.

"Our address book has for a long time been one of the top things developers wanted access to," said Chris Yeh, head of the Yahoo Developer Network. That's because, over the years, Yahoo users have filled it with billions of individual records.

Yahoo users have stored more than 500 million address books, and the service is used by more than 150 million unique users each month, Yeh said. "A lot of our address books (are) constantly being updated. It's one of the biggest sources of contact information on the Web," he said.

Opening the address book API (application programming interface) is the second major step taken so far in executing the Yahoo Open Strategy that Chief Technology Officer Ari Balogh announced in April. The first step, in May, was opening the SearchMonkey project so outside coders could make more creative use of Yahoo search results.

"The address book is the second proof point. This year, we'll show proof point after proof point," Yeh said.

Yahoo Open Strategy is an attempt to link the company more with other Internet activities rather than remain a sealed-off, if sprawling, Internet domain. Through its open strategy, the company envisions outside programmers building Web applications on Yahoo's site, Yahoo services being incorporated into outside applications, and social connection information within Yahoo being used more widely.

Whether Yahoo will succeed in capturing developer attention and becoming a more dynamic part of new developments remains to be seen. A lot of action--some complementary but much of it competitive--also is taking place at rivals such as Facebook, Google, and any number of small Web 2.0 start-ups.

From the outside looking in
The address book move means outside Web sites will be able to read and write address book information--if a user grants permission through a Yahoo authorization process.

A site with a gift registry could piggyback on the address book so that a person could tell contacts about a wish list of presents, for example, Yeh said. Or a site shipping packages to others could auto-complete the address fields on a Web form.

(And something I'd like to see happen: somebody please endow the address book with an interface that doesn't look like it dates from 1998. I have a lot of contacts stored away in the Yahoo address book, and I find it excruciating to update addresses, scrub out obsolete e-mail addresses, or update mailing lists.)

Explicitly opening the service is more secure than one alternative today, in which a third-party site asks a user for Yahoo log-in credentials so it can access the site and scrape the contact information.

"There's no control over what happens after a user gives that (username and password). The third party could use it to log in to mail or any other part of Yahoo," Yeh said. "It's not a real secure method."

Yahoo isn't opening up the interface for an address book creation, though, which means it won't at least for now be usable as a generic back end for a Web site's address book needs.

Social graph theft?
One interesting possibility raised by the openness is whether an outside company might use it to steal, in effect, a user's social graph--the collection of connections each user often must laboriously reproduce as he or she joins a new site. Social graphs are a key asset of Web sites with a social element, in part because it's hard to reproduce them elsewhere. So once a user constructs one, there's a strong incentive to remain loyal to a site.

Yahoo isn't concerned about that, in part because opening the interface will mean other sites will be able not only to extract contact information from Yahoo, but also to synchronize changes on their sites back with Yahoo, Yeh said.

"I don't think we're worried about losing control over our social graph. All the things we're doing now are trying to break down some of the traditional walls Yahoo has had to the outside world," he said. "Yes, absolutely some of our data will get pulled out and be used for benefit of other systems. (But) when people use our system address book APIs, there's just as much a chance somebody will load something back into our network."

One company making use of the Yahoo address book interface is Plaxo, which hosts 40 million users' address books already.

Yahoo itself maintains multiple social graphs--for example, the address book, the Yahoo Messenger buddy lists, and the Flickr lists of contacts, friends, and family.

"Not all this data is combined yet," Yeh said, though one key part of Yahoo Open Strategy is to unify these contact lists and the related user profile pages. "The goal of the next half year is to make sure we bring that together."

The Yahoo address book is the "place we like people to store all their contact information," he said, but it's not a terribly rich social graph. For example, it doesn't currently have a good way to distinguish which contacts would be appropriate to invite to a new social service or to receive gift registry notifications.

"One of the things that we have to do is give users and opportunity to activate their social graph a little bit--essentially, to make sure they can classify the people they're most interested in communicating with on a regular basis so we know how to create a social environment around them," Yeh said.

"Going forward, we'll have to have a better solution for people so we can classify inside our address book who we're closest to and who are at further distance from us," he added. "That's a function of the social work we're doing."

Yahoo on Thursday will take one of its first big steps to make its site a more vital part of the Internet.

The company will offer developer tools to let programmers start using SearchMonkey, technology to make search results more elaborate and, the company hopes, more useful. SearchMonkey lets programmers write applications that can turn dry textual listings in search results into a much more elaborate display, and Yahoo hopes its search business will benefit.

"We want this to be the most productive search experience anywhere," said Amit Kumar, whose title is chief searchmonkey.

In addition to taking the programming tools out of closed testing, Yahoo is opening a "sandbox" where programmers can test their SearchMonkey applications and announcing a contest with $20,000 in prizes to try to jump-start development. Eventually, users will be able to choose the SearchMonkey applications they want from a gallery.

SearchMonkey is interesting, and attracting developers is a time-tested way for technology companies to build stronger, richer technology in years to come. But Yahoo has serious competitive challenges. In search specifically, it continues to lose ground to its top rival, Google, where more than three times as many searches now take place in the United States. According to search market share statistics from HitWise released Wednesday, Google had 67.25 percent share of U.S. searches in April to Yahoo's 20.28 percent, Microsoft's 6.26 percent, and Ask.com's 4.17 percent.

This compares standard and SearchMonkey-enhanced search results.

(Credit: Yahoo)

SearchMonkey isn't the sole part of the Sunnyvale, Calif.-based company's effort to reclaim lost relevance and to placate investors unhappy with the Yahoo's financial performance. SearchMonkey also is the first example of an effort called Yahoo Open Strategy (YOS) to wire the company's many Web properties closer together, expose their features for consumption by outside Web sites, and make them a foundation for programmers who want to build their own applications.

What does SearchMonkey do?
SearchMonkey is an example the latter category, an application foundation. With it, Yahoo lets programmers package some specific search results on Yahoo's site with more sophistication.

For example, a result that lists a local restaurant can feature its phone number, address, and a photo. Or a result with a movie can feature an average reviewer score and nearby theaters.

That's the basic version. Things get a notch fancier with what Kumar calls Infobars, or frames around a result that a user can click for further information. For example, a movie Infobar could expand to show cast and crew information from the Internet Movie Database and a plot summary and movie-ordering button from Netflix.

I see it as similar to building small Web pages into the search results.

Infobars can provide more elaborate information to people who click.

(Credit: Yahoo)

The idea is that publishers will write their own applications that can be added to the search results. They can also promote them to try to get people to install them.

So will your search results become cluttered with results that can look a lot more like flashy ads?

Not if you don't want them to, Kumar said. "Users will quickly be able to remove the apps if they feel they're encroaching into what's supposed to be an ad-free area," Kumar said.

Yahoo might turn some applications on by default, but only if there is strong interest and utility. One candidate is business information from sites such as Yelp or Yahoo Local, he said.

At this stage, Yahoo isn't considering deals by which publishers pay Yahoo to switch on the SearchMonkey applications by default, Kumar said.

"Our first recommendation would be to spread the application virally," he said. "If an application isn't good enough for hundreds of thousands of people to add it, it's not good enough to turn it on."

Monkeying with the Semantic Web
SearchMonkey also is interesting because it fits into the broader sweep of Internet history. Tim Berners-Lee, who initially developed the protocols behind the World Wide Web, has for more than a decade been advocating a move toward a more advanced sequel called the Semantic Web. SearchMonkey specifically takes advantage of Web site features designed to fulfill some of the promise of the Semantic Web.

The Semantic Web is a somewhat counterintuitive concept. Although the Web is geared for human consumption, the Semantic Web seeks to imbue Web pages with meaning that computers can understand. Better computer comprehension, though, will mean better data processing and information presentation for the ultimate benefit of us humans.

Or so the thinking goes. It's been a long, slow shift toward the Semantic Web. But there are real moves under way now, and the promise of more prominent or useful search results at a major site such as Google could further advance the Semantic Web.

The inner workings of the Semantic Web are not simple.

(Credit: Tim Berners-Lee, W3C)

One manifestation of the Semantic Web that's catching on is something called microformats. It's not the full-blown Semantic Web vision (see Berners-Lee's graphic to the right for the whole shebang), but it's a close relative.

Microformats are essentially small labels tucked into Web pages that describe content so that computers can understand the nature of specific bits of data: phone numbers and other contact information, addresses, events, calendar items, for example. In March, Yahoo announced it's begun looking for microformat data as it indexes the Web.

"If there is a structured mark-up you can put on the Web pages, then the machine is going to understand it better," Kumar said. "That's what the Semantic Web is all about."

SearchMonkey is geared to surface micrformat-labeled data, Kumar said. The company hopes developers who build SearchMonkey applications will "help us get the structured data to the users who are going to use it," he said.

One interesting possibility of microformats is that it can take some of the guesswork out of indexing the Web and therefore make accurate search results easier to achieve. Could that help Yahoo catch up to Google?

Possibly. But I suspect there's still plenty of informal information on the Web. And even when microformats provide some structure or guidance, I suspect there's a lot more computer science work to be done in inferring the meaning of Web pages.