For a busy C-level executive, finding a good personal assistant to rely on is not just a movie cliché or a creature comfort that comes with the position. It’s often necessary for successfully performing the duties of the job. For the rest of us, companies like Microsoft, Google, and Apple are looking to replace the human personal assistant with a software version. But when it comes to actual practical situations, the products have so far been mostly unrefined prototypes.

For its part, Microsoft is looking to change that by acquiring new technology and the innovators who created it. On August 22, 2016, Microsoft announced that it was acquiring Genee, an AI-powered scheduling service. The deal also includes the hiring of Genee co-founders Ben Cheung and Charles Lee. This is the second announcement in a month of new scheduling technology at Microsoft and it reveals an interesting strategy for the company.

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Education is the key

Let’s face it: While the technology behind products like Cortana and Siri are better than they’ve ever been, those services are still not as useful as they could, and should, be. They are certainly not as useful as a human personal assistant. To put it bluntly, Cortana is an underachiever in need of a proper education.

The team at Genee has developed artificial intelligence software and optimized decision-making algorithms that improve natural language interaction when scheduling appointments. Genee will take what it knows about your schedule, compare it to what it can find out about another person’s schedule, and make informed decisions about when, where, and why to schedule a meeting. Just the sort of education Cortana needs so badly.


As it did with the announcement of Bookings earlier in 2016, Microsoft is looking to solidify its position as the de facto software to use when starting the collaborative process in an enterprise. With the features found in Windows 10, Azure, and Office 365, Microsoft wants to be the go-to collaboration software in the enterprise. With a better, more educated artificial intelligence made possible by Genee, Cortana–in conjunction with Outlook or the Calendar app–could simplify the scheduling process and by extension, enterprise-wide collaboration.

It is an ambitious strategy and there are going to be acquisition missteps, but there is really no other way to approach the problem. A digital personal assistant built with intelligence that actually makes life easier is too alluring to ignore. Whether it is Cortana, Siri, or some other product yet to be created in someone’s garage, the day you can actually talk to your device and have it truly understand what you are saying–not just the words, but also the intent–is evermore possible.

Bottom line

When it comes to the elusive efficient digital personal assistant, Microsoft wants to lead the way. It will get there either with internally developed technology or by acquiring technology developed elsewhere. The acquisition of Genee suggests that the entire digital assistant industry is looking at a marked increase in consolidation through mergers and acquisitions. I would not be surprised to see other small innovative companies in this market snatched up by the bigger players during the next year or so.

So it appears that once again we are going to see a market dominated by a few big technology players. The usual suspects are Microsoft, Google, Amazon, and Apple. Care to lay odds on which digital assistant will end up putting its company on top? At this point, I think it is too early to call.

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Your thoughts

I think digital assistants are still too primitive to be practical, but you may not agree. Do you use Cortana on a regular basis? Share your experiences with fellow TechRepublic members.