Why Cortana doesn’t work at work

Microsoft is betting that Cortana will bring AI to the workplace. Here’s why that won’t happen.

Cortana is an intelligent agent  that is supposed to act as a personal assistant. You can interact with her (notice I said “her”? More on that in a minute) via voice or text, on mobile devices or on desktop computers. Given that Microsoft’s mobile market share has fallen below 1%, it’s pretty much a certainty that most people would interact with Cortana in their offices.

We know that most Windows 10 computers are in workplaces, so there’s a very strong likelihood that people will talk to Cortana in an office. This is very different place than where people might interact with Siri on their phones, or Alexa in their homes. Siri and Alexa t are called upon in private, controlled places (in fact, just 3% of iOS users report using Siri in public).

Let’s walk through that interaction of Cortana as a member of a workplace.

Microsoft encourages you to command Cortana by saying, “Hey Cortana…” and then giving her a command. A typical office scenario might be, “I wonder if I should book a vacation for the first week of August. Hmm. I’ll ask Cortana.”

This is how Cortana is supposed to work:

User: Hey Cortana, should I book a vacation for the first week of August?

Cortana: Let me check your calendar. Looks like you have a meeting on Monday, August 1st. Should I move it for you?

User: Yes, that’d be great.

Cortana: Okay, I’ve moved that meeting to Monday August 8th. Would you like to see some vacation suggestions?

User: Yes, please!

This is exactly how it plays out on a demo video one Microsoft’s site.

But let’s face it: there are a lot of contextually dependent reasons why this is completely unrealistic. Leaving aside Cortana’s technical limitations for the moment (and there are many), let’s take a look at what a real office and real user might look like.

Most offices are either open concept without even the suggestion of walls. As many as 70% of us work in open concept offices. As anyone who’s worked in such an office can tell you, hearing a neighbor on the phone can be excruciatingly annoying or excruciatingly awkward, depending on your neighbor’s TMI quotient.


So there’s a good chance that everyone in the user’s office will hear this idealized scenario.  There are two clear disincentives against this happening. First, Cortana will make more “boundary work” for office workers. The mere act of trying to keep your private life private at work is turns out to be, well, work. Recent research  has found that keeping work and life private actually causes cognitive overload. If people use Cortana as intended, she is poised to make that much worse.

Second, Cortana demands office workers treat their workplaces as if they were kings and queens, instead of pawns and rooks. Voice interactions require workers to own their workspace, something that we know they do not do. Typical workers share their workspaces with others, and because we are apt social animals, we tend to comply with unwritten rules of workplace etiquette. Bosses’ calendars take precedence over workers’ calendars. Bosses talk more than workers. Men talk more than women. In other words, people with power talk out loud more than people with less power.

Which brings me to the fact that Cortana is a woman. Is it any coincidence that most intelligent agents today are anthropomorphized as women? One of the most striking changes in the twentieth century workplace was the almost total elimination of support staff, which were typically women. Only the most senior executives have assistants nowadays, and other mid-level white collar workers are on their own for scheduling  and administrative work.

cortana 02

Let’s not forget that Cortana is actually based on a supportive AI character in a video game. Cortana provides these workers with a sense that they can indeed recoup the times of Mad Men and have a compliant, supportive, and self-abnegating assistant who has no needs of her own. Practically, this promises white-collar workers with a huge productivity boost, but the symbolic nature of this is even more interesting. When white-collar workers have a virtual assistant, they have re-claimed a sense of hierarchy, of control, and power (even if it is completely imaginary).

And this is why Cortana will not work in the workplace. Today’s typical office worker does not have power enough to command the space around her, and bark orders to anyone out loud, even if just to an intelligent agent. This office worker has been stripped of her ability to occupy a rung on the ladder higher than admin or support staff, because there is no admin or support staff. This typical office worker is embedded in a physical space that reflects this lack of hierarchical position — she has no command over it.

Scholars of gender and technology have described some ill-advised approaches to gender equality as “add women and stir.” The same applies to Cortana and other intelligent agents. You cannot “add Cortana and stir” and expect to see productivity improvements that somehow negate the existing organizational and physical structures of contemporary workplaces.


Identity management: the future of privacy?

The nature of privacy of is changing.  This should come as no surprise to anyone, since the pace of technological change has rapidly outpaced our existing social and legal norms.

Some have argued that privacy is now a right reserved only for the rich. This story of the Seattle City Light company reinforces that view. According to the Seattle Times, City Light’s contract with Brand.com to manage its image focused more on CEO Jorge Carrasco’s personal Google results than on the company itself.

Jorge Carrasco

Seattle City Light paid Brand.com $17,500 for the contract, which focused on expunging a particular Seattle Weekly article from Google search results.

In particular, the records show, Carrasco was aggravated by a negative Seattle Weekly article from 2008 that kept popping up in search results about him. As late as last month, Carrasco and a top aide were exploring whether they could get the piece expunged from Google entirely.


That original story focused on Carrasco’s high-handed management style, and argued that he “decimated employee morale,” and revealed his nickname as “Jorge Fiasco.”

On the surface, this story appears to be about misuse of public money for personal use. But digger deeper, what it is really about is two things.

  1. Identity management is work: I have found repeatedly in my research on productivity that individuals are increasingly tasked with achieving, monitoring, and policing their online images. This kind of work is increasing in scope and effort.
  2. Privacy is for the rich: because reputation management is increasing in its scope and effort required, privacy itself is now a job. Obviously in this context, those with means can better marshal resources to protect their identities. Individuals without time, resources or skill to manage their identities will have a more difficult time.

In short, we are seeing productivity increasingly involving improving one’s image. Tools like Social Sweeper are already offering resume “cleaning” services — to those who can afford it.

When will more traditional productivity tools offer the same services? And how much will they cost?

Why does technology present so many privacy problems?

Consider the following facts:

What is it with technology that makes these kinds of privacy breaches so common?

The importance of physical objects in privacy

We recruit physical objects to prop up our privacy. Doors, walls and curtains help us control access to information by obscuring the view into private space. Sometimes, objects are used to indicate a purely symbolic boundary, as in the case of a window. In public or shared spaces, we recruit physical objects to demarcate space we claim as private. Yoga class participants carry out this process by placing their mat on a carefully chosen spot. New arrivals to the class know that space is now “taken” by another student.

An office with walls and a door is less accessible than a mere desk – even when the office door is open. Fictional news reporter Les Nessman illustrated this by painting yellow lines on the carpet around his desk. Visitors to his “office” were asked to pantomime knocking on the “door.”

Figure 1: Les Nessman answering his “door”


The physical context of information tells us how private that information is intended to be. A piece of paper sitting in plain view suggests it is not private information. But that place that same piece of paper in a folder, and shut it in a drawer and the information is clearly intended to be private. The physical context itself connotes the nature of the information.

In the digital world, we no longer have these physical objects to help us. The digital context lacks the same fidelity of the physical world. Without physical objects to indicate the nature of privacy, digital objects typically are given metadata to indicate their private nature.

Metadata’s primary shortcoming is that it doesn’t relate the object to other objects, thereby robbing the user of a rich source of information. Imagine a photo placed in a frame and set on a piano. Imagine the same photo stuck on a corkboard, next to a mug shot. Imagine it again placed in a shoebox and tucked under a bed. Then imagine this photo posted on Facebook. The human mind quickly intuits the meaning of the object by means of comparing it to other, nearby objects. In the digital realm, objects are stripped of this context. Hashtags or metadata lack the richness of the physical context, and makes it that much more difficult to intuit the private nature of the object.

Ethnography and the importance of attachments and involvements

Elsewhere I have argued that ethnography is one of the best ways to understand how products relate to people and to the world. I argued that Heidegger’s concepts of “attachments” and “involvements” are what ethnographers should be looking for in the field. How does this product fit with other products? How does it fit with with people? You must understand a potential user’s system if you’re developing a product, and ethnography gives you a high-fidelity view into the user’s world.

This is one of the reasons we have so many privacy breaches; digital products were developed without understanding the user’s attachments and involvements, especially those relating to privacy. Sadly, entire business models have been built on users not realizing this fact, and over-sharing their information in a digital space. In the physical world, they might unconsciously recruit physical objects to communicate a high-fidelity privacy desire. We need more systems to integrate this desire, but with authentically digital options.




[1]       A. Westin, Privacy And Freedom, vol. 25, no. 1. New York: Athenum, 1967.

[2]       A. Cerra and C. James, Identity Shift: Where Identity Meets Technology in A Networked Age. Indianapolis: John Wiley & Sons, 2012.

[3]       M. Madejski, M. Johnson, and S. M. Bellovin, “The Failure of Online Social Network Privacy Settings,” New York, 2011.

[4]       B. Meeder, J. Tam, P. G. Kelley, and L. F. Cranor, “RT @ IWantPrivacy : Widespread Violation of Privacy Settings in the Twitter Social Network,” in Proceedings of the Web, Vol. 2, 2009.

[5]       T. a. Pempek, Y. a. Yermolayeva, and S. L. Calvert, “College students’ social networking experiences on Facebook,” J. Appl. Dev. Psychol., vol. 30, no. 3, pp. 227–238, May 2009.

[6]       E. Protalinksi, “13 Million US Facebook Users Don’t Change Privacy Settings,” ZDNet News2, 2012. [Online]. Available: http://www.zdnet.com/blog/facebook/13-million-us-facebook-users-dont-change-privacy-settings/12398. [Accessed: 06-Dec-2013].

Mundane technology’s massive impact: the case of social network overload

We often have the mistaken impression that “breakthrough” technologies are the ones that will be the source of radical change. The first rocket. The first telephone. The flying car. These technologies stand out in our collective mind as iconic innovations. Such innovations, we believe, cause irrevocable social change.

The innovator’s dream, crushed by reality

Unsurprisingly, it is that “flying car” that most technologists seek to create, something so radically different, so completely new, that it will disrupt social lives and business models.

Yet this almost never happens. Radical innovation is rare, and radical innovation that takes root in social life is even more rare. Instead, it is the large number of small innovations that culminate in large-scale social shifts, and it is in that space where technologists should focus.

Fertile Field No. 1: Communication Channels

One such space today is that of online social networks and their respective communication channels.These networks have proliferated, and with them has emerged a dizzying array of “channel choices” through which we must now choose to communicate.

Imagine you have just had a successful first date. Once upon a time, you might have wondered to yourself, “Should I call him?” How quaint. How simple. How 20th Century.

Now, of course, you must create a mental flow chart, with all your channel choices if’d and then’d with your ambiguous social reality. Is he a friend of a friend? Is he your “friend,” on Facebook, on Twitter, on Instagram, or maybe even LinkedIn? Will you see him at the office tomorrow? Will you “see” him on skype later? The flow chart proliferates with innumerable maladroit choices, each one a potential social landmine ready to blow up in your face (and his).

Welcome to the 21st Century, the time of enriched social channels but impoverished social etiquette.

Worse still, individuals are not only ridden with social angst over their choices, but they are also overwhelmed with notifications.

Adroit social actors will of course navigate this field, if not with actual aplomb then at the very least with competency. The rest of us are left with a dizzying set of communication choices and nary an @EmilyPost to help us. It is a bewildering time.

Mind The Gap: The TRiZ Method

Such times are ripe for innovation. At this moment (and I do mean a “moment” in the historical sense of the word), there is a gap in technology. Such gaps are, unbeknownst to most, the most opportune for new products and services to emerge. They are also ripe for new social practices to emerge, which most tech observers tend to miss, gloss over, or underestimate the impact of.

TRiZ analysis (or теория решения изобретательских задач, or theory of inventive problem-solving) shows us why “breakthrough” technologies are rare and often without the hockey-stick growth of other, more mundane innovations.

One truth of technological change is its remarkable unevenness. Some technologies grow and change at remarkable rates, while other technologies languish, perhaps due to technical limitations, or more likely due to political economic reasons. Take, for example, the incredible growth of SMS texting on mobile phones. SMS is a simple technology, requiring entry-level technical skills. It is not “sexy” but it is massively adopted.

SMS turned 20-years-old in 2012, and is now the pre-eminent way mobile phone users around the world communicate. By 2002, Indian mobile phone users were sending 250 billion SMS texts a day. In 2008, SMS replaced voice phone calls as the primary way people use their mobile phones in the United States.

SMS took off because mobile phone voice calls remained too expensive for most people to use frequently. SMS, by contrast, was initially free on most mobile systems.  Adding even more wood to the fire was the fact that SMS is discreet and socially inconspicuous. A quick text under the table is far less socially intrusive than a voice phone call while having dinner.

Is SMS a killer app? Yes. Was it ever pursued by technologists to be the killer app? No.


The Gap in Communication Channels

There is a similar fertile gap waiting to be filled in today’s harrowing communication landscape. Users are begging for tools that help them make the most socially astute channel choices, and at the same time, reduces the information overload they are experiencing. Our search for notifications has corrupted our social and internal lives.

We are no longer able to navigate the sheer volume and socially ambiguous nature of our communications ecosystem. The Killer App of the 20-teens will not be the one that ADDS to that morass, but the one that saves us from it.

The communications landscape is primed for a tool that will “even out” the uneven technological development. We have no limit to the number of channel choices we can make, but we have no way to manage these choices well. Hootsuite is one tool that has filled this gap, to a limited degree. It allows us to manage multiple Twitter feeds, by multiple people. Its main advantage is its ability to help small businesses manage social media, which today equates to the sum total of small-business marketing strategy.

We need a similar tool, not just for Twitter, but for all our channels. The Next Big Thing is likely to be a tool that saves us from our Technology Loops and helps us manage the context collapse that social networks now present us.

In my next post, I’ll explore another fertile ground for innovation: managing the rapidly proliferating data that we ourselves are generating, just by living our increasingly digital lives.