Microsoft's Cortana needs be the best enterprise assistant to survive

Cortana and Microsoft logo

Cortana and Microsoft logo (Image credit: Windows Central)

Cortana, Microsoft's beleaguered digital assistant, has gone from what Microsoft said was "the world's most personal digital assistant" to a virtual unknown among consumers.

Contrary to the enterprise-to-consumer dynamic that drove personal computing's early evolution, consumers are now a major industry driver. Consumer-focused smartphones are a nexus and launchpad for today's multifaceted personal computing experiences. Digital assistants, smart homes, augmented reality (AR) platforms, app ecosystems, smart speakers and more are being propelled into the mainstream by mobile platforms.

Without a smartphone, Microsoft is a non-participant in these emerging segments though it has made attempts. Perhaps the lack of a competitive mobile platform, persistent misinterpretation of the consumer market or ineptness in executing its plans, has led to Microsoft's vanishing consumer presence.

Whatever the reason, Cortana, like most of Microsoft's efforts, has been relegated to the enterprise as prospects for her consumer success wane. Today, making "her" the best enterprise assistant may be the only way Microsoft can ensure her survival.

Businesses have their eyes on Cortana

Pindrop, a company founded in 2010 with the goal of bringing "security, identity, and trust to every voice interaction", conducted a study of 500 businesses. The study's results indicate Cortana is the top pick for companies that are planning to implement voice assistants to communicate with customers, beating Amazon's Alexa, Google's Assistant, Apple's Siri and others.

Companies are motivated to embrace voice because they believe it is an important customer satisfaction driver, provides a competitive edge, will improve efficiency and will reduce customer transaction costs. Additionally, two-thirds of businesses plan for digital assistants to manage a majority of customer interactions, while 25 percent will trust them to handle all customer interactions, according to that study. This data reflects a tremendous opportunity for digital assistants in business.

Most companies have historically embraced Microsoft's trusted tools, like Windows and Microsoft 365, as they've considered implementing emerging tech. Thus, long-standing partnerships and the "inertia" of Microsoft-biased business decision-making are likely reflected in companies choosing Cortana over other options.

Cortana, assistant to assistive

I recently wrote about how Microsoft's Corporate Vice President for Cortana, Javier Soltero, said that Microsoft is repositioning Cortana as more of an aim to enhance productivity, rather than a distinct assistant akin to its rivals.

Thus, Microsoft is progressively integrating Cortana throughout its products and services to support facilitating tasks and cross-platform experiences. Consequently, Cortana is becoming more transparent as "part of the process" compared to her highly-visible consumer-focused counterparts.

Still, with limited regional availability and skills outside of the U.S., Cortana's digitally-assistive enterprise focus is Microsoft's attempt to leverage its strengths to save Cortana. Fortunately, Microsoft's decades of enterprise relationships give the company an IT infrastructure advantage over rivals.

Microsoft 365 and Cortana

Thousands of companies use Microsoft 365 products, such as Office and Teams. These tools diligently record who employees are, what they look like, their positions, calendars, locations, individual and group projects and much more. Since Cortana is part of these services, Microsoft's first step in making her the best enterprise assistant is aggressively pushing what she already brings to the table.

For example, Cortana and Microsoft Graph help facilitate cross-device user experiences. And via Timeline, she'll help users pick up where they left across platforms. Microsoft even demonstrated Cortana recognizing and greeting users as they enter a room for a meeting.

Additionally, with intelligent calendar access, she can proactively assist with employee scheduling. She also recognizes when certain files are relevant to a particular context and proactively alerts users to them. This reflects Cortana's knowledge about a user or a team's personal and professional productivity.

Cortana the know-it-all

Cortana can know virtually "everything" about everyone within and between organizations, recognize associations between people and data and know what's relevant in what contexts. This "intelligent omniscience" based on her access to the breadth of Microsoft's tools integrated within businesses will be key to making her the best enterprise assistant.

Finally, Office 365's merged work and personal authentication means the Cortana that knows a user at work is the same Cortana that knows them at home. Thus, if Microsoft makes Cortana the best enterprise assistant, those strengths may ultimately have consumer appeal.

Jason L Ward is a columnist at Windows Central. He provides unique big picture analysis of the complex world of Microsoft. Jason takes the small clues and gives you an insightful big picture perspective through storytelling that you won't find *anywhere* else. Seriously, this dude thinks outside the box. Follow him on Twitter at @JLTechWord. He's doing the "write" thing!

  • I hate to say this, but pathetic... Even when MS has a head start they still drop the ball.
    Luckily there's still 100,000,000,000 years left till the earth implodes on itself for them to get it right🙄
    Any competent company this size shouldn't need advice from "Jason Ward". SMDH (No offense, Jason)
  • That's so obvious, isn't it?
  • Too much stuff is not obvious to MS. Lol
  • I work somewhere that use to be considered a "Microsoft Shop", and now we run from the term. We're already running pilots with Alexa as our enterprise AI. Cortana is never mentioned.
  • Bad "start"...
  • Serious question for you, why does your company need an Enterprise AI? I can't fathom any use for an AI on my laptop at work. I'm just drawing a blank on the whole concept of an Enterprise AI.
  • No one knows for sure; however, they have visions of things like Publicis' Marcel ( and more. Even simple items like, "add a $30 taxi to my expense account for this trip", "or tell Bob I will be 15 minutes late for the meeting today", could be done with an AI assistant. For the talent of the future, "the digital natives", this doesn't sound crazy... or at least those are the thoughts. Here's the weird thing, Marcel was built on Microsoft tech, but it is never mentioned and the video even uses Google (with maps) boldly but doesn't mention Microsoft at all. That's because Microsoft's reputation, even in the enterprise, has taken a huge hit when they gave up on mobile. People just don't want to be associated with the name, or present innovations to leadership with the Microsoft name associated to it. They proudly say Apple does this, Google does that, and now even Amazon does this, but even if you build on Microsoft tech you just keep it quiet. It's weird, but it is a very real fact. I've read the technology trend thoughts on if tech moves from enterprise to consumer (as it was before), or consumer to enterprise (like the iPhone and Android). Were smart phones an exception, or just the direction technology is going to move from now on? Alexa may help answer that question. It is clearly consumer based, and was quickly pushed out before it was even 'ready' at first. However, Amazon just keeps pushing out more and more devices and iterating on Alexa, while Microsoft put out one partner device (Invoke) and plays with stuff behind the scenes waiting to have a perfect device before making a serious move. It is clearly two very different approaches, and one that (so far) makes Microsoft look far behind and moving at a snails pace. Microsoft appears to be betting that a large consumer base for Alexa won't be major impact for enterprise AI decisions, and Amazon believes the opposite. The funny thing is, without Office integration Alexa wouldn't stand a chance, but Microsoft signed away that advantage so Cortana could order you something from Amazon.
  • I would guess that AI would be used, just as one example, to find data or keywords in your emails or on business onedrive a lot more effectively than searches. You could ask Cortana to find your last email from so and so and add them to your calendar etc. instead of manually clicking through multiple apps. I'm sure there are uses for it. We use Office at work and there's no clear central repository of knowledge. If Cortana could be that, even with typing instead of voice, I would use it.
  • Speaking of where I work I have to agree. There's no way I'd run to upper management right now and pitch a Cortana solution. They all have company issued iPhones and iPads and now spend the MAJORITY of their computing day on those devices, relegating their PCs to mostly email, which is often handled by their **human** assistants anyway. We have no digital assistants yet in the office, but most of the execs I know use Siri on their phones, and Alexa at home. That's the world they understand. And they hold the purse strings! With no mobile device on the Consumer front, this gap between Microsoft products and those who control the budget will only get worse in the Enterprise... not better. Microsoft better wise up and soon if they don't want to be permanently relegated to back office products and email. The lines between Consumer/Mobile and Enterprise are forever blurred now. The old world model doesn't work anymore.
  • Totally on point!
  • Cortana has been more useful in Halo. I'm sure she will be removed from Windows in a couple years.
  • Don't worry, Windows altogether will be removed in a few years on this course. Nadella destroys.
  • Lol
  • If I can't use Cortana on a Dutch language Windows I do not care one bit about it, really, I will not make my Windows English (US) just to use Cortana
  • The mythical Cortana in cars which never came about... Whatever happened to the Nissan partnership? How is Microsoft going to get in vehicles when all companies want to do is tell me about Apple and Android Play?
  • Interestingly enough, most of what the in car assistants can do now, Cortana on Windows 8 and 10 Mobile did quite a bit directly from the phone. You could respond to call or texts, using your voice and did everything else that Google and Siri do currently. It was and still is the best in car assistant. Unfortunately, mobile didn't work.
  • Windows 10 Mobile was a terrible experience in the car. Bluetooth and SMS rarely worked, there was no screen mirroring since Microsoft backtracked on the MirrorLink standard. Since I drive long distances for work, I am so much happier with my iPhone and CarPlay.
  • I agree. Others say it was horrible, but not in my experience. Best recognition and accuracy - and I've used them alland am back with Google for text to diction, which is horrible when vompared to Cortana. Cortana is still way better, but MSFT doesn't know how to market and take advantage of their better offering.
  • I develop using bot framework and Luis. We need more straight forwards ways to use this frameworks together with translation apps to augment and customize Cortana experience. We need Microsoft to democratize the local translation app SDK. The local translation quality is not state of art compared to what available online. So give us the local SDK API!
  • What I love about Cortana is her integration with the OS, this symbiosis should progress as MSFT continue to develop Windows 10. Clearly no other AI has one of a kind advantage like this. If MSFT does realize it, how is it that we don't see Cortana come up, again?
  • Cortana is a victim of several Microsoft decisions; 1. Closing down WIndowsphone.
    2. US Only strategy where Cortana has had restricted or no functionality outside the USA
    3. Consumer abandonment strategy If a voice assistant is going to work it has to be where people need it. It has to do something that, for example, keyboards don't do. So it has to be on mobile where you use your voice. It has to be on smart speakers. It has to work with meetings, calendars, diaries, flights, rail journeys. It is literally pointless to have a reminder to do something then when the reminder is due you are using an Android phone with Google Assistant as default.
  • And, we still don't have SMS read over Bluetooth on Android. Did they just give up on this?
  • "Microsoft needs TO be the best enterprise company to survive." There, I fixed your headline for you. Both grammar and content.
  • Cortana is the Microsoft vulnerable backdoor for Google market penetration through Google Assist to Microsoft enterprise safe heaven.
  • I have full faith as per the Microsoft's undeclared motto, they will drop the ball 🏉 as usual
  • Microsoft has to get a move on and get Cortana to more regions with her full feature set not just limited to basic things. I'm working at a company and they solely use Google for almost everything. The next step they are look at is Google assistant incorporation compared to others and it will most likely be my job to find practical reasons to do so. I'm not going to let my feelings towards Google get in the way of my assessment. There is one coworker who uses a Surface and since everyone use google apps, the office is considering using chromebooks. Chromebooks! Not Surface devices, macs but friggin Chromebooks. Microsoft's diabolical track record with reliability with Windows 10 updates are not helping. They need to rehire Quality Assurance testers and programmatic testers. The developers do not have enough time in the day to design, develop, test, reiterate, test. This snail pace and US centric focus is not helping at all. As I'm not the only person stuck in this situation where they are being forced into Google's ecosystem because of Microsoft's short sightedness.
  • Could u easily bring out a series of YouTube videos supporting your case for Cortana instead of Google assist? Why not? Shouldn't Microsoft fload the social media with that, survival of the desperate! Google assist could be the key way to replace enterprise dependency on both Win10 hardware and software
  • @GeorgeOnArm.
    I could but what would I talk about?
    All the awesome skills and features are not available to people in the UK. It's locked to the US. I can only affirm what I have tested and seen myself.
  • Most of the apps we develop in the Enterprise these days are web based apps... HTML5, jQuery, CSS. Either that or they're publicly facing iOS/Android apps. I can't tell you the last time anyone built a Windows app where I work. So yeah, there's every reason why Chromebooks would work splendidly in the enterprise. For the handful of **legacy** apps remaining that run only on a Windows platform, they can easily be virtualized and run in a Chrome browser. Nadella's retreat from Mobile has done nothing but confirm the notion in people's minds that Microsoft is a fat aging dinosaur, completely out of step with today's world... a MOBILE world... less and less used in the home, in schools, and no longer **necessary** in our work places. Of course Nadella's retreat from Mobile and Consumer has served him splendidly in the short term... he's a Wall Street darling because of it. But once the "I'm not Ballmer" effect wears off... and it will wear off... and the business world realizes that the emperor has no clothes, the MS board will be asking itself why they ever let that crackpot out of the backoffice and into the head office.
  • I wouldn't agree on calling Satya Nadella as a crackpot but he is very, very short sighted never the less. Then again most people see beyond one step. I agree with the rest of your points. As long Microsoft pigeon holes itself as US only. Google is has reached it's tentacles into the enterprise sector and is drastically shifting the conversation towards their products. Google has put alot of thought in this ahead of time. They've played the game and turned it into their favour.
  • Let me stupid this Oh my keyboard and not direct any word... He'll if Microsoft can't even get keyboard working correctly, then what chance do they have with Clive seems
  • To sum it up and this applies to many Microsoft efforts, intentional or unintentional (via the 80/20 Rule effect), half assed.
  • I've said it before but realistically Cortana voice commands will be a nightmare for anyone working in an office with multiple people. I can't imagine how annoying it would be in our office of 30 people all saying 'email Dave" "open excel" "what's my next appointment" etc. Too many Cortanas close by would probably get confused too about which one was being talked too even if they were trained on your voice.
  • Na bro it'll totally work in the toilet. Cortana, flush... "ding dung derp... Opening solitaire". While the next stall flushes with some idiot still sitting there trying to complete his massive dump, splashing hepatitis infested toilet water onto his anus. Cortana will totally work for the enterprise. Have faith.
  • You could call AI assistant the next OS, with visuals as output if desired. Google's(maybe even other's) regional voice recognition,... is way better.
    Before being the best, it needs to be on the same level at least.
  • As I said elsewhere, live 2D/3D/AR Cortana interface, for usage with screen content(shown data or text input/output) and visual input/output(mimics) is as well important.
    Its so hard to use anyway, wish AI could learn from people, like a kid or at least dog learns, it would made it better by millions.
  • Sure, theoretically that sounds good. But in reality it omits a key factor, bias. Everyone has an element of bias and not everyone can fully address that bias. Impartiality is a skill that requires understanding ones own temperment, emotions, actions, reactions and thought processes. But even then there is always that little element of bias but we call that morality. The basic understanding what is right and wrong. Real world examples about that - what is happening at the US border. If everyone deemed it was wrong then it wouldn't be happening.
  • I think the open-source solution Roamit is better and provides many more options such as copying the clipboard including images and files. It also has special handling of URLs and can open them on the remote device. There are also extensions for Chrome and Firefox to automate the process even further.
  • I would change the title of this article: "Microsoft's Cortana needs to be on her own mobile platform to survive". No enterprise user will install a secondary assistant in a mobile device with its own/native assistant.
  • Cortana will only have appeal if it supports more languages and regions. Being a smart AI and knowing what people is not enough. If there is no basis with Cortana, which is communiction, Cortana can be smart, but there is no dialogue, no communication, if you don't understand the same language. As long as microsoft does not adress this Cortana will still be at the same place it was 5 years ago, despite improved AI.
  • I think it needs to master one language first. There are probably different skill sets that could be implemented broader than others but if you haven't mastered one language what's the point? Mark Twain said: "It's better to keep your mouth shut and appear stupid than open it and remove all doubt” Implementing a half assed solution across multiple languages would remove all doubt. There is in every opportunity a window (time period) to succeed. The window may already be closed. The breadth of skills available may be analogous to the app gap on mobile. Microsoft seems to have missed on the skills acquisition window and is still bumbling the basics.
  • When your comments HERE get replies, do u get notifications? Why not??? Will the notifications engage u more to discussions??
  • Microsoft should focus on making Cortana universally available. As a UK based Windows Windows fan, Cortana has gone from exciting, to ok, to appalling. Wtf Microsoft
  • It is sad, that Cortana even though that had so much of potential from the start, its development began to stagnate for so long. And now it is the assistant with the worst localisation and you have to change your location to use Cortana. :(
    I changed my location and I am using Cortana every day. I can definitely say, that she is much better than Siry. We did some comparison, and for most of the things Siri did not know or could not do it and Cortana had answers or could do what I asked for. But still, Siry is avalible worldwide even in a few avalible languages.
  • No, they need to make it speak more language, make it good, and tell people about it. As everything else MS in consumer space....
  • Yes, I'd love to buy books, movies, use Cortana and much more they are blocking for many countries.