Daniel Serfaty had to appreciate the irony. The founder of Aptima, a Woburn, Massachusetts, software developer, Serfaty was working hard to build a new, high-powered social-networking system designed to find connections between people attempting to solve similar problems. Think Facebook, except rather than connecting college students looking to flirt and swap pictures, it would match people who have highly complex technical questions with experts able to answer them. But there was a rub: Serfaty was having trouble finding a development partner who shared his goal--the very sort of problem his system was intended to solve.

But then the Department of Defense--which Serfaty had pitched but hadn't been much interested in funding Aptima--suddenly came calling. Why the change in tune? Two DoD managers who had never collaborated, even though they worked one floor apart, ran into each other at a cocktail party and decided that what the department needed was a system that could help people like them find each other.

Scoring the sort of elusive connection that is normally the domain of plain dumb luck is, of course, the promise of online social networking. But if you've spent any time on social-networking websites, you know it seldom works out that way. That's because most of those sites offer more quantity than quality. Log on to MySpace (NYSE:NWS) or Facebook or even a business-oriented social-networking site like LinkedIn or Spoke, and it won't take much time at all to build a network of thousands of contacts. The problem? Managers of sophisticated, fast-growing companies don't need the world at large to chip in when they have a question. They need input from exactly the right people, and those people are extremely hard to identify and track down.

Fortunately, a new generation of social-networking software is on its way, software that not only lets people build impressive webs of connections but also analyzes those networks to provide all manner of insights to users. Serfaty's software, for example, monitors a network's online communications, such as e-mail and instant messaging, to learn who communicates with whom--and uses keyword analysis to determine what sort of problems and expertise are being tossed back and forth. Aptima's software, which remains in development and is not yet available, will be able to suggest instantly who on the network is the best person to consult when a specific problem comes up. "You leave your footprints everywhere you go in cyberspace," says Serfaty. "The system can pick all these footprints up and deduce from them that you should call John on the fifth floor to get an answer to your problem."

Serfaty's quest is not exactly new. Businesses, mostly large corporations, have been trying for years to get at information about who within an organization talks to whom about what via a technique called organizational network analysis. But such analyses have been cumbersome, expensive, consultant-driven affairs that rely on interviews and surveys and don't keep up with how relationships and topics change--all of which makes it extremely difficult to use such studies to solve problems as they come up. In effect, Aptima is automating the process of organizational network analysis by gleaning it from online activity.

It's not the only company taking that approach, which might be termed "intelligent social networking." Annapolis, Maryland-based eTelemetry already offers a $35,000 self-contained box that can be attached to a corporate network to trace an organization's electronic communications and map out a network analysis chart that shows which individuals in the organization serve as the hubs or linchpins between different groups. It may turn out, for example, that some lowly product development dweeb has somehow become the go-to guy when the marketing folks want to figure out what the R&D people have up their sleeves. Later this year, the system will gain some limited ability to recognize people's areas of interest via their Web-surfing habits, notes the company's CEO, Ermis Sfakiyanudis. "You'll be able to use the information to see who the thought leaders are in an organization and bridge gaps between departments," he says. The American Association of Airport Executives, an 80-person industry group, has begun using eTelemetry to improve informal lines of communication between employees. "If we can see where the bottlenecks are, then we can do things to speed up decision making," says Patrick Osborne, who heads the group's IT efforts. "We might want to give those employees who are at the hubs of information flow larger budgets or more responsibility."

Meanwhile, Visible Path, a Foster City, California-based company, has released a beta version of its e-mail-tracking tool on its website. Like eTelemetry, Visible Path doesn't examine the content of messages; it only notes who sends messages to whom, when they send them, and how frequently. But the company claims it can use this information to derive reliable insights into whether someone has a close working relationship with a contact versus a cursory one. And Illumio, a new product from Tacit Software that is available to individuals for free, pores over the information on the PCs of everyone on a network--it relies on the data indexed by Google's (NASDAQ:GOOG) and Microsoft's desktop search tools--to identify the people most likely to be able to answer a particular question.

Of course, identifying the right person to talk to is only part of the problem, notes Aptima's Serfaty. In addition to being knowledgeable, a good collaborator is someone who's not currently bogged down in other tasks, is willing to be helpful, and works well with people like you. That's why Aptima's tools are being designed to take into account not just the depth of knowledge and experience of the people in the network but also their workload and workstyle. Serfaty's team, which is working with MIT's Media Lab, is even investigating how the system might recognize the ways in which external events can alter connections--as, for example, the way a suicide bombing in the Middle East can affect political, cultural, and religious alliances. In a business context, that might mean recognizing that a big jump in the price of steel strengthens potential ties between small manufacturing companies and plastics distributors. It sounds compelling, but don't reach for your checkbook just yet. Aptima's systems are still in the experimental stage; when they are available, they'll be aimed at government agencies and large companies. Should they prove successful, systems for smaller companies and consumer markets will follow.

Needless to say, monitoring e-mail and other communications poses privacy issues. But as I've argued in this column before, if you give people a benefit in return for giving up some of their online privacy, most will go along with it. In the case of Aptima and eTelemetry, the goal is to get entire organizations to install the software; that will take care of privacy considerations because, in general, companies have the right to subject employees to communications monitoring. That would allow the broad mapping of relationships throughout those organizations and between any organizations that agree to pool their networks.

The drawback is that people outside these organizations won't be able take advantage of the tools, and it's often the case that the person who has the solution to your problem isn't in your company. Visible Path, which has made its software available to the public, hopes to create a mass cross-organization network, but only if it can get enough individuals to sign up to have their e-mail tracked. On the other hand, there's nothing to stop Aptima and eTelemetry from eventually opening up their tools to the public, perhaps by cutting deals with a Web giant such as Yahoo (NASDAQ:YHOO); both companies say that's a possibility. And Visible Path, which has teamed up with business information provider Hoover's (NYSE:DNB), is eager to sign up entire companies as well as individuals.

But even intelligent social-networking tools, no matter how smart they get, will sometimes fail to get a handle on who can solve whose problems. That's because despite all the emphasis we tend to place these days on online activity, many of the most effective people still get a lot of their work done the old-fashioned way, that is, via phone calls or by dragging their butts over to someone's office for a talk, and the substance and even existence of those conversations can't easily be captured. And no matter how capable and all-knowing these systems get, you'll still stumble on the occasional great contact at a cocktail party or trade show or on an airplane flight. Technology can do wonders, but there's no complete replacement for the miracles accomplished every day through plain dumb luck.

Contributing editor David H. Freedman (whatsnext@inc.com) is a Boston-based author of several books about business and technology.