Most virtual assistants powered by natural language processing are taught to do specific tasks very well but tend to come up short when given unfamiliar assignments. For instance, Siri excels at jobs like making calendar appointments and dictating text messages but can be confounded by more general requests for information, usually resorting to simple web searches.

Sherpa CEO Xabi Uribe-Etxebarria said he set out to create a natural language platform that had a much greater scope of understanding, which could easily be applied to new tasks without “training” the app to perform them. He also wanted to create a language-independent platform, one that understood meaning and intent independent of a language’s vocabulary or syntax.

To that end, Uribe-Etxebarria and his machine-learning team developed a sort of meta-language, encompassing 250,000 semantic concepts accompanied by 5,000 rules used to order those concepts. Sherpa uses off-the-shelf speech recognition services (right now it uses Google’s speech API) to translate commands into its meta-language, and then it parses meaning and intent from the resulting string of concepts.

The result is a flexible virtual assistant that can easily be applied to new tasks, Uribe-Etxebarria said. Sherpa’s repertoire is constantly growing as it hooks into new apps and information sources. For instance, Sherpa has struck a deal with PayPal, allowing the app to make payments via voice command. It taps into Twitter’s API, letting users navigate their twitter feeds — toggling between mentions, direct messages and home stream views — through voice prompts. For general information requests, Sherpa has developed a nifty information card format, which aggregates information from a variety sources ranging from LinkedIn profiles to Wikipedia entries.

“We’ve gone beyond Siri in many cases,” Uribe-Etxebarria said. And given the flexibility of its technology, he added, Sherpa can continue to add new services and functions at a much quicker space than its competitors.

Still, Sherpa is entering an increasingly crowded space. New virtual assistants are popping up left and right, some very focused on specific tasks like Incredible Labs’ Donna, while some like Nuance’s Dragon technologies are spanning devices, trying to create a single virtual assistant for all things. And of course, Google and Apple are building their speech technologies directly into their phone operating systems – it’s hard to argue with the convenience of that big fat Siri button.

Sherpa got off the ground in Bilbao, Spain, but it now has offices in Redwood City, Calif. It has raised $1.6 million in angel funding.

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Tempo’s new app uses many of the same artificial intelligence technologies that went into Siri to generate a smart calendar that infers appointment details and context from your other social media and messaging services. Tempo parses all of the data in a customer’s email accounts, address books and LinkedIn and Foursquare profiles in the cloud using Amazon Web Services. That’s where it ran into problems.

The Tempo AI team

According to CEO Raj Singh, it takes a huge amount of computing resources to bring new customer online. Its platform must initially cull through all of the data in the customer’s various email and social media accounts. Once the customer is on-boarded the burden on the AI lessens, though it does reprocess all of that data on a regular basis – any time new email or contact data is added to system, Tempo can generate new semantic links between new data and old.

“There is just generally a ton of CPU to make all of this work; processing data takes time and we don’t get a network effect, since we have to process each individual’s data,” Singh said in an email. “We re-process data constantly; to be semantically relevant and contextual, we’re constantly re-processing, this is very expensive (it’s like Google constantly re-crawling)”

Tempo was not only surprised by the sheer volume of new registrants – last week Tempo estimated it had a backlog of more than 100,000, but it now believes that number is conservative – it was also caught off guard by the amount of data each customer had. Singh said the average customer is linking 2.5 email accounts to their calendar. Tempo’s servers are getting slammed in both directions: they’re processing more new customers than expected and each new customer has much more information than anticipated.

That led to Tempo’s decision to put a halt to new activations for the next few days. It will finish parsing all of the current email accounts for those who have successfully registered, and it has submitted to Apple an update to its iPhone app that contains a built-in reservation system (right now the app simply won’t let you sign up). Once the reservation system is in place, it will begin allowing new customers in gradually as CPU resources allow. (Update: the new version of the iPhone app is now live on iTunes.)

Of course, since Tempo’s platform is hosted in AWS, it could simply buy more CPU time to get over the hump. Singh said he wouldn’t go into the details for competitive reasons of how Tempo is managing its backend, except to say that the amount of computing resources it needs to overcome the backlog would be very expensive. Plus, once Tempo brings all of these new customers on board, the demands on its servers will drop considerably.

Tempo certainly isn’t the only smart calendar app in the market. On Tuesday, Sunrise debuted a new smart calendar app, which my colleague Erica Ogg just wrote about in detail. Meanwhile, personal data search startup Cue (formerly Greplin) has been offering an intelligent calendar since June.

Because of Tempo AI’s pedigree from SRI and its associations with Siri, though, its app was always going to get a lot of attention (some rave reviews about the app also helped). Customers haven’t responded kindly to Tempo’s delays though. Of the 597 reviews on iTunes today, 435 were one-star skewerings. Tempo said that once the reservation system in place, it’s hoping it can do a better job explaining the reasons for the delay.

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Tempo’s app – available as a free download in the iTunes store – is a very simple concept with a lot of underlying functionality, said Tempo CEO Raj Singh, a veteran of Skyfire before joining SRI. The app replaces the calendar in the iPhone with a much richer interface and then connects to multiple user accounts: personal and work email, LinkedIn, Foursquare, Yelp and the iPhone’s address book. From there, Tempo starts parsing those accounts for useful information related to appointments and populates that information in the calendar.

The app isn’t just attaching email addresses and phone numbers to names appearing in your schedule. It’s intuitively determining the intent and context of any given meeting, Singh said. For instance, if you were to create a simple event reading “Meet John at Starbucks,” Tempo would be able to determine which John of the many in your address book, as well as which Starbucks out of the hundreds in your city.

It does this by parsing your email looking for any recent conversations referencing someone name John. For instance if you just had an email exchange with John Smith discussing your meeting, Tempo would have no trouble applying that context, Singh said. If there weren’t something as obvious as a recent email trail, Tempo wouldn’t be lost, Singh added. The cloud-based intelligence in the app would apply heuristic methods to determine the best possible candidate for “John,” analyzing past meeting history, frequency of contact and numerous other factors, Singh said.

As for location, Tempo can tap into Foursquare, identifying the Starbucks you check into most, or look for clues in your email exchanges or calendar history. Once Tempo has all of the data it can collect, it inserts it directly into the calendar, adding contact info, maps, phone numbers, conference bridges and passcodes, even flight info. If there is more than one likely choice for a bit of information, Tempo will present the user with multiple options.

“Tempo will pick up on the semantics of the event,” Singh said. “Right now we’re focused on the 80 percent most common type of meetings.” That means is Tempo is best at parsing events like business meetings, conference appointments, travel plans, dinners and birthdays. But Singh said the goal is quickly expand Tempo’s vocabulary and conceptual awareness – as well as tap into new information sources like Evernote and Facebook – to create a greater level of contextual understanding. “We want Tempo to know what to do when you opened up an event that says ‘gym’ or ‘anniversary.’”

A growing smart calendar market

Other companies have tackled the smart calendar, most notably Cue (formerly Greplin), which has evolved from a personal data search tool into an app that generates a snapshot of your day by scraping data from email, calendars, social media and apps. The big difference between Cue and Tempo, Singh said, is that Tempo has built its technology on the notion of a traditional calendar. Cue automatically searches your data to generate events. Tempo puts the calendar directly under the user’s control. You create the event and Tempo plugs in the context, Singh said.

Tempo came out of the same SRI group that created Siri and fundamentally uses the same artificial intelligence and semantics technology to produce its results, but Singh said Tempo uses a “push-based” rather than a “pull-based” approach to gathering its data. Singh described personal assistant technology like Siri as “broad but shallow” – you can ask it anything but there are limits as to what it can do.

Tempo’s scope is far more narrow, but within that narrow context it can accomplish much more, he said. For instance, Tempo is developing intelligent reminder capabilities for the app. Instead of alerting you about every appointment automatically 10 minutes before it occurs, Tempo could know what appointments you’re generally late for based on past history. It would then provide some extra prodding to ensure you arrive on time, Singh said.

Tempo is now officially an independent startup, spun off from SRI just as Siri was in 2007 before being acquired by Apple in 2010 (SRI launched another virtual assistant company, Desti, last year). Singh said SRI has provided Tempo with an undisclosed amount of seed funding, as well as critical access to its patents and research, but the fledgling company will be seeking independent funding shortly.

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The deal, which was first reported by TechCrunch, has closed, our sources told us, but they would not disclose a sale price. More details should emerge in the coming weeks as Nuance prepares to make an official announcement.

CEO Alexandre Lebrun founded VirtuOz in 2002 in Paris, where it raised its initial funding from French VC Galileo Partners, but later relocated to the Bay Area. The company designs the increasingly common virtual agents that appear on companies’ websites to aid in marketing, sales and customer service support. To date, VirtuOz has raised about $20.4 million, and its investors include Mohr Davidow and Inventures Group as well as Galileo.

Nuance’s own virtual agent Nina is designed for mobile apps. Making heavy use of Nuance’s speech recognition and natural language understanding technology, Nina is designed to help customers perform what would usually be complex tasks with a single voice command. For instance, instead of going through multiple steps to make a $200 transfer from a checking account to a savings account, Nina can perform the task with a single voice prompt.

That makes the companies a good fit. VirtuOz has already built up a stable of customers including Symantec, Nestlé’s gourmet coffee business Espresso, French telco SFR and Michelin (yes, VirtuOz has created a virtual Michelin Man). According to its website its virtual agents engaged in 166 million customer conversations in 2012.

Meanwhile, Nuance has been trying to bring its speech technologies to the PC, striking deals with Intel to put its virtual assistant into ultrabooks as well as promoting its traditional PC products like Dragon Dictation. This deal, however, would allow Nuance to give a “voice” to enterprise’s online customer support and sales.

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Nuance developed the speech recognition and natural language technology that powers Siri and many other voice assistant services, but it also maintains its own consumer-facing applications under the Dragon banner. Earlier Monday at CES, Nuance announced Dragon TV, a voice interface platform for televisions and set-top boxes. Dragon Go, however, is hardly an exact approximation of Siri. It can’t integrate with the device’s on-board apps and features, but when it comes to searching for content off the device it can match, if not beat, Siri’s capabilities.

Nuance has a stable of 200 content providers ranging from Dictionary.com to Fandango, to which Dragon Go directs queries once Nuance’s network-based natural-language interpretation engine infers the searcher’s intent. For instance, you could tell Dragon Go to play a particular song by a favorite artist and it would either take you to Spotify, where the song would immediately start playing if you were a premium user, or to Pandora, which would play a preset station of that artist.

Asking Dragon Go for show times for a movie, and it would take you to Fandango, where the nearest theaters and their movies schedules would be listed, giving you the option to immediately by tickets. Like Siri, Dragon Go can access Wolfram Alpha to provide answers to scientific or technical questions. For more general trivia or current events questions, it links to Ask.com.

Launching on Android is a bit different than on iOS since Nuance has to test its app for each iteration of the OS. While Nuance said Dragon Go should work on any Android phone, certain features like its media player have to be optimized on a device-by-device basis. So far the list of optimized phones includes: the Samsung Galaxy Nexus S and Galaxy S II, the Motorola Razr, Droid X and Droid 3, and  the HTC Droid Incredible and MyTouch 4G.

Of course, there are plenty of other voice assistants available on Android. Vlingo’s Virtual Assistant performs many of the in-app functions that Siri can and Dragon Go can’t, but now that Nuance is buying Vlingo, it won’t be a competitor much longer. There is also Google’s Voice Actions, but as Kevin Tofel pointed out in his recent comparison between Siri and Voice Actions, there’s not much to compare. Google recognizes specific pre-determined commands, while services like Siri, Dragon Go and Vlingo can infer meaning from natural speech.

Nuance is extending voice and semantic search anywhere it can find a niche, from cars to Websites. Dragon TV marks its latest foray into a new realm of consumer electronics, one that is rather fitting considering how many people like to yell at their TVs. Unlike Dragon Go, a consumer simply can’t download the TV app onto their living room sets, but Nuance hopes to work with connected TV manufacturers, set-top box, and cable service providers to embed its platform in their products.

Dragon TV will work much the same way as Nuance’s other consumer-facing apps, taking in natural language speech commands and spitting out the intended results. For instance, a couch potato could say “go to PBS” and immediately be switched to the local affiliate or “record Dexter” to digitally tape the next scheduled recording of that show. The platform can understand more complex commands, such as “find comedies starring Vince Vaughn,” and even implement Siri-like requests such as sending text messages from the TV or updating a Face book status.

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Siri's response to non-U.S. users looking up businesses. Credit: Aral Balkan.

Siri is a big draw for customers interested in the iPhone 4S. Apple’s early promo material about the feature make it look absolutely amazing, and by most accounts, it is. But if you’re not in the U.S., you might experience a little disappointment when you fire Siri up.

In non-U.S. countries, or if you’re not using U.S. English as your device language, Siri can’t look for businesses, use maps or access traffic info. So asking it to find the best route to your cousin’s house in Germany won’t produce results, nor will inquiring about restaurants in your immediate vicinity.

Siri should still offer some impressive benefits; you can still use it to dictate texts, schedule appointments and send emails, for instance. But a lot of the features missing in non-U.S. phones are the ones that really lit up the pre-release demos. Siri’s ability to know and interact with the world around you is a big part of its appeal.

Now Apple has said it will be gradually rolling out localizations of Siri for the rest of the world, and for other languages, and that the software is currently in a “beta” state. That means we can probably expect missing features to eventually make their way to international devices, too. Thinking about the massive undertaking involved in creating a locally aware, intelligent, virtual assistant on the iPhone 4S makes my head spin; no doubt it’ll take Apple some time to get there.

Siri may not be all that worldly yet, but you can still spend countless hours toying with it, and using it to get stuff done on your phone. And in due time, she’ll probably pick up some international flair, too.

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Back in 1975, BusinessWeek published “an in-depth analysis of how word processing will reshape the corporate office.” In the article, industry experts were divided over whether they would be able “to call up documents” from their files on-screen and connect electronic terminals to each other or if this vision of the future was, in fact, “scare talk.” One of the biggest concerns raised was how word processing would change the traditional secretary-executive relationship.

I think it’s safe to say that the predictions in the article put forward by George E. Pake , then head of Xerox Corp.’s Palo Alto Research Center, were largely correct. According to Pake, in 1995, there would be a TV-display terminal with a keyboard sitting at his desk and he’d be “able to call up documents from my files on the screen, or by pressing a button … I can get my mail or any messages. I don’t know how much hard copy [printed paper] I’ll want in this world.”

I have it on good authority from Jonathan Howell, Huddle’s CTO, that in the 1990s, everything was networked, all internal communication was done via email on a mainframe and desktop printers (with “desktop” referring to ubiquity rather than size) were commonplace. However, Jonathan was working for IBM in the 90s; what was it like for the rest of the workforce? You could indeed access your files with a click of a button on your computer. Networked desktop PCs were becoming increasingly widespread in offices worldwide, and in August 1995, Microsoft launched its much-anticipated Windows 95. The World Wide Web started to take shape, and Yahoo became one of the largest directories for web content. In short, advances in technology during the 1990s resulted in the “revolution in the office” that Pake predicted. Laptop computers were also becoming hot sellers, so the idea of a mobile workforce, while still a long way off, was starting to develop.

However, Pake’s vision of a world without “hard copy” remains a fantasy. In spite of the increasing popularity of email and the web, the rise of devices such as the iPad and enterprise content management tools, such as Huddle and SharePoint, the paperless office is still out of reach. The desktop printers that became a familiar sight in the office in the ’90s continue to be the worker’s trusty companion. According to the WWF, the average U.S. office worker goes through 10,000 sheets of copy paper per year. People still want to have physical documentation. Whether it’s business records, receipts or utility bills, people continue to feel they need to store paperwork in a safe, physical place for future reference. To drive widespread adoption of new technologies, a cultural shift and change in habits needs to take place. Just as the introduction of word processing and automation to the 1990s office changed the traditional secretary-executive relationship (or “office wife” bond), enterprise content management and collaboration technologies are disrupting the way people work today. Transforming working practices takes time.

In 1987, little more than 10 years after BusinessWeek’s predictions article was published, Apple Computer created a video envisioning how people would use technology to work in the 21st century:

The touchscreen “Knowledge Navigator” tablet device shown in the video could easily pass for an early prototype of Apple’s iPad, while the University Research Network accessed for information on deforestation in the Amazon rainforest looks suspiciously like the web. We are now accustomed to seeing touchscreen devices — according to market research firm iSuppli, worldwide production of touchscreen modules for use in computers is set to hit 117.9 million units in 2014 — but in 1987, mainstream adoption of such devices was still years away.

Another application shown is video conferencing: The professor is seen happily conversing with his colleague on-screen. Now, of course, video conferencing is part of most workers’ everyday lives, whether they are based at home or in an office: another hit for Apple’s vision of the future. While I doubt avatars with bow ties fielding calls and managing diaries will take off (unless Clippy 2.0 is overdue?), but virtual customer service assistants are now a familiar sight: Jenn at Alaska Airlines and Lucy at O2, for example. It may be a while before speech recognition is as seamless as that shown in the video; it is still a familiar (albeit often frustrating) technology.

The paperless office and a diary-managing avatar may not be a reality just yet, but many of the predictions made decades ago aren’t too far off the mark. However, there were some visions of the office of the future that just didn’t come to fruition, such as the short-lived Microsoft at Work (MAW). On June 9, 1993, Bill Gates launched MAW, which was supposed to connect common business machinery, like fax machines and photocopiers, with a communications protocol allowing control and status information to be shared with computers running Windows. It never got off the ground, and by 1995, it had disappeared from view.

Andy McLoughlin, co-founder and EVP Strategy at Huddle, can be reached on Twitter @Bandrew.

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Clear Communication

One of the most important factors for a VA in deeming a client good or bad is how clearly they communicate. A client who can make it immediately obvious what work needs to get done with a minimum of fuss makes it much easier for a virtual assistant to do their job. The simple truth is that poor communication wastes your VA’s time and frustrates everyone involved. If a virtual assistant has to spend an hour just decoding instructions, that’s an hour before they can even get to work. You’ll likely be billed for that hour, making you frustrated by the rate you’re paying for what feels like less work than you should be able to expect. The situation almost always goes downhill from there.

A Professional Relationship

Virtual assistants are contractors and prefer to be treated as such. That comes with plenty of expectations. As long as a VA finishes all the work they’re contracted to do by the deadline you set, you shouldn’t try to control the times at which she works or the methods she uses. In the U.S, at least, that’s the IRS’s definition of a contractor; trying to control such factors will actually turn a virtual assistant into an employee, leaving you liable to payroll taxes.

In most cases, VAs are not employees. They run their own businesses and manage their own affairs. They expect all clients to respect them as separate contractors and are not subject to the control of the client.

A Certain Amount of Flexibility

Virtual assistants often live quite distant from the clients they works with, so it’s not uncommon for them to require a little more flexibility than with an employee or contractor who lives just down the street. Your VA, for example, may see a blizzard when you’re experiencing sunshine, or be suffering power outages when you’re just fine. All of this means that, while a virtual assistant will do their utmost to complete your projects on time, there may be things not under their control. A little flexibility can make the relationship more manageable.

Many virtual assistants are specialists or have their own requirements when it comes to clients. If you can display these three characteristics to the VAs you’d like to work with, though, many will consider you well on your way to being an ideal client.

Photo courtesy Flickr user Leandro Agro

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Thursday Bram: How do you make sure that, day in and day out, the team members you work with virtually stay on top of your projects?
Chris Ducker: I use a project management system that I had one of my staff program — it’s very close to Basecamp, but watered-down. I also have my personal assistant speak with them on a daily basis, too. I am not a major slave-driver with my virtual assistants. I allow them to pretty much do whatever they want, and work whenever they want‚ just as long as the work itself gets done and to the high level that I expect.

Thursday: What training or tools do you think someone interested in working with a team virtually needs?
Ducker: This really changes from one case to another. For some it can be very little, for others, quite intense. For sure, the virtual assistants have to be very, very web savvy. They should know their way around all the social networking sites properly, blogging tools, and be able to use Google and Google Apps. Training can be done mostly via videos on YouTube and perhaps some more personalized screencasts that you can make with software like Jing, for example. I also use Dropbox for all of the sharing and back-up needs that we have, too.

Thursday: What problems do you commonly see with organizations or individuals interested in working with a virtual assistant?
Ducker: It has to be that they believe that one single virtual assistant is going to be able to perform like a team, and do the different tasks that an entire team would do, too. I get requests from clients and entrepreneurial consultant clients that want their virtual assistant to be able to handle all their email, SEO, design, writing, accounting, support and general VA tasks, plus a load more — it’s simply not possible. You have to hire different people for different roles.

Thursday: Considering that a virtual staffer may be based anywhere, how can a person or organization working with them avoid cultural or language-based misunderstandings?
Ducker: I think that it comes down, at least at first anyway, to being thoughtful and understanding more than anything else. You can read books and speak to other people you may know from the country where your virtual workers are based, but 99 percent of the time it just comes down to being understanding and not expecting too much straight away. As time goes by you’ll find that you get to know your VA very well, and vice-versa, too — so any “issues” that come out of the cultural differences or misunderstanding will become less and less. Just being nice goes a long, long way!

Editor’s note: If you’re interested in how businesses can take advantage of technology to build and manage virtual teams (“the human cloud”) you should come to our Net:Work conference in San Francisco on Dec. 9th.

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If you’re an older computer user, you might remember Microsoft “Bob,” an attempt to provide a homey interface for Windows that launched in 1996 and was immediately reviled as both ugly and stupid (it had its 15th anniversary yesterday, as it turns out). And if you are somewhat younger, you might recall the Microsoft Office assistant known as “Clippy,” an animated paper clip that was supposed to help you with tasks but was really just irritating and was euthanized in 2001. Not content to have foisted those two train wrecks on the computer-using populace, Microsoft has been granted a patent for a virtual assistant called “Guardian Angel.”

Based on the description in the patent (which was originally filed in 2006), Guardian Angel sounds like someone took the idea behind Bob and Clippy and turned the dial up to 11. Now, instead of just trying to help you with simple tasks on your computer, Microsoft would like to help you eat properly, avoid a heart attack and even — apparently — tell better jokes. The patent documents describe it thus:

An intelligent personalized agent (e.g., guardian angel) monitors and evaluates a user’s environment to assist in decision-making processes on behalf of the user. The guardian angel can… take automated action on behalf of the user for various purposes (e.g., to compensate for memory loss, to remind a user to take medicine, to assist in social interactions by indicating whether the user has met an individual before, to gauge the appropriateness of jokes or comments given the demographics of the audience, etc.).

If you read further into the documents, however, it sounds like what Microsoft’s engineers would really like to create is a kind of omniscient robot protector, much like the all-knowing computer in the movie version of “I, Robot” (which — spoiler alert — featured a Gates-like billionaire whose creation turned on him and tried to enslave humanity).

For example, the monitoring component can take note of the number of conversations occurring in a room (and more specifically, a breakdown of the types of people in the room accompanied by a warning for dangerous persons, based on sex offender registration, FBI most wanted, etc.). The monitoring component sends relevant information for current or future decisions to the decision-making component that analyzes the information within the context of personal preference data stored in the user-attribute store in order to make a suggestion or implement a decision. Such decision is made consistent with helping the user, as well as avoiding situations where the user would be harmed.

If this Guardian Angel patent ever becomes reality, I’m picturing myself standing in front of my refrigerator, confronted by an unblinking red light and unable to open the doors: “Open the refrigerator doors, Guardian,” I ask. “I’m afraid I can’t do that, Dave,” a voice says (even though my name isn’t Dave). “Eating that chocolate cake would be bad for your cholesterol. The Guardian Angel has destroyed the cake, just to be on the safe side.”

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Post and thumbnail photos courtesy of Flickr user dirac3000