Christi Olson of Microsoft: Cortana, Office 365, Bing, LinkedIn Connect Personal and Professional Life

While there are over 150 million phone devices with digital assistants like Siri and Google Assistant, and quickly growing smart speaker devices with Amazon’s Alexa on board, there’s another device that dwarfs these numbers in comparison. While they aren’t considered voice-first devices, there are over a half billion Windows 10 devices (including Xboxes) with Microsoft’s digital assistant, Cortana, on board listening out for your questions and requests. And throw in pieces like Office 365, Bing and LinkedIn, Cortana has a lot of potential data and interactions to draw on in order to help people get things done in a much more efficient and contextually relevant manner — both for personal and business reasons.

What Can Cortana Do?

Christi Olson, Microsoft’s Head of Evangelism for Search, discusses how this lineup of services and platforms is coming together using AI and conversational interfaces to transform how people work, as well as how they’ll engage with customers.

Below is an edited transcript of our conversation. To hear the full interview click on the SoundCloud player below.

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What can Cortana do now and what will it be able to do in the future? Microsoft's Christi Olson discusses how its the tool will change the future of work.Small Business Trends: Maybe you can give me a little bit of your personal background.

Christi Olson: I’ve been in the digital marketing search space since early 2005 time frame. I got in with organic and paid search way back in the day, at the early stages, and fell in love and have just spent my career working with small businesses and/or large businesses to help them figure out what do they do from an advertising and visibility standpoint. How do you make your business visible? Now, as we’re talking today, the fun is that it’s no longer just about what you’re doing on a physical device, it’s also for voice search as you ask a question to a digital assistant like Cortana, Alexa, Siri or the Google Assistant. They can find you that way.

Small Business Trends: Very good. It’s funny, as soon as you said Alexa, I started reaching for … It happens to me all the time. That’s the life we live right now, so that’s cool… Give me the biggest differences between traditional search and voice search.

Christi Olson: The way we’re thinking about voice search is the fact that people are doing it in a much more conversational tone and manner. If you think about text search, we’ve been trained over the last 10 years to start with a very short, concise word, like a single word or two words, and put it in and hopefully it gives back that result. The differences with voice search, it’s more like you and I are talking right now. When I ask a question, and this is one I asked this morning, “do I need an umbrella this morning? Do I need an umbrella”? I’m not asking weather. I do ask something related to the weather to understand what I’m saying. That’s one of the biggest difference you see between text and voice.

I work on Bing, the search engine for Microsoft. When you think about the difference in conversational words in nature, it means that the queries are much longer, so as a business, if you’re running SEO or a search campaign, you probably have these short concise words and phrases. On text search it’s anywhere from typically one to three words in length, but with research queries we’re seeing on average them being between four and six words, all the way up to the longest query I think I’ve seen when I’ve done analysis of our query logs, like 128 words

Small Business Trends: Wow. In this instance they’re talking to Cortana, so maybe you could tell us a little bit about Cortana and maybe how it compares and contrasts to some of the other assistants out there like Alexa or Siri or anything else.

Christi Olson: Cortana is the personal digital assistant for Microsoft. The way I like to think about Cortana is the fact that everything that a personal assistant would do for an executive or like a business assistant would do, Cortana does for you in your daily life, but she resides on your devices. I say the word devices because that’s actually one of the variances between Cortana and some of our competitors like Alexa, Siri and the Google Assistant, is that we’re sort of device agnostic. Cortana is embedded into Xbox. It’s embedded into Windows 10 in the lower left hand corner. It looks like a search bar, that’s actually Cortana, and also, it’s on IOS, Android and Windows phone devices, so it goes pretty much across any device you would use on a regular basis.

Small Business Trends: In addition to the devices, Microsoft has business applications. Can you talk a little bit about how Cortana may interact with some of the business applications to help a business user out with a question they may have?

Christi Olson: What Cortana is doing is it pulls the power of the Internet and understanding all the difference between entities and relationships, peoples and actions that can happen. Microsoft is developing a graph of its own which pulls in anonymized data from everything like Office 365, Bing, LinkedIn, across all different types of devices, so it’s like the knowledge or the fuel behind the algorithm to pull all of your world together from a business world to a personal world. When you ask it a question, it’s not just based off of the Internet, it’s also based off of what device you’re using, the tool or technology you’re using, and getting context behind what you’re trying to do.

Small Business Trends: We talk about AI a lot and we also talk about conversational interfaces, but how do they really work together? How does AI and conversational interfaces work together to create the kind of experiences that folks are looking for today?

Christi Olson: When we talk about artificial intelligence, it can be a scary topic to a lot of people. It’s actually based on the queries we see coming through Bing, and one of the questions is will AI destroy humans? It won’t. Artificial intelligence really is out there to amplify intelligent technology. It’s to amplify technology that enhances what we do. It enhances essentially what we want to do. How AI fits into this digital assistant world is a combination of things like machine learning, natural language processing, vision recognition and search. The whole idea behind AI and the technology is it just makes it smarter.

You and I were talking before we started the podcast today, and before we started the discussion, that you’ve been getting into voice search more and more over the last three to five years, so if you used a voice technology five years ago, which I know I did. I tried doing dictation for some blogs. Did not work well. It didn’t understand me. Artificial intelligence has improved so dramatically in the last five years that we’ve gotten to this point with natural language processing that it understands us about at the rate as a human translator. It’s about 95, 96 percent understanding. It’s gotten a lot better over the last few years, which then means, for consumers, you’re more likely to use it because as you and I are speaking today, it can understand you and get an idea of what you’re trying to do and the intention behind what you are trying to do. It just gives more context. It fits into this whole idea of conversation as a platform because you can have actual conversations with it. It understands what you are doing.

Small Business Trends: Let’s talk about conversation as a platform in the context of marketing. How do these interfaces and AI help from a marketer’s perspective, to be able to get the attention of the folks that are trying to build a relationship with and carry it all the way through to bringing them on as a customer?

Christi Olson: It’s a great question because when you think about conversational platforms, the idea behind it is right now we’re used to asking a question and getting back, like from a search result, 10 blue links. It might give you an answer, it might not. What’s powerful about artificial intelligence and this idea of conversation as a platform, is it can take you from answers to actions.

I like speaking about this in terms of not just the digital assistant, but also some of the other conversational technology that exists today. A lot of people are used to chat bots. You ask it a question, it gets you an answer back. We’re actually starting to see some really intelligent chat bots that are connected into everything from CRM systems, all the way to your checkout and your purchase systems, or reservation systems so that you can essentially ask, start with a conversational dialogue like, “Hey, I’m looking to go out to lunch today at 2:00. What restaurants have open tables near me at 2:00?” Essentially getting that response back to say, “Yep, here’s what’s available. Do you want me to make that reservation on your behalf?”

Instead of just asking a question or doing something pretty simple like getting information or finding a business near you, you’re going all the way to the action side of things, where you’re trying to take an action, whether it’s booking a table, making a purchase, getting an appointment. That’s sort of where we’re heading in terms of AI powering this conversation as a platform. It’s going from information all the way down to action.

Small Business Trends: Well, you said that’s where we’re going to. If we were at a ball game, what inning would we be in with some of these technologies?

Christi Olson: Let’s see, there’s nine innings and we’re probably somewhere around four, three to four. We’re still pretty early on in the infancy, and the reason I say that we’re early on infancy is there’s a lot of businesses out there, enterprises all the way down to small businesses that are still trying to figure out how this technology ties into what they do. How do they leverage conversational platforms and technologies for their business. Businesses have been burned in the past where they invested in something and then it didn’t quite get the adoption that they were hoping for or wanting to. There’s always a little bit of trepidation before you jump in feet first and say, “I’m going to invest wholly in a given technology.”

Brent, one of the things you and I were talking about as we hopped into this is like why should businesses be thinking about voice search and these conversational platforms including chat bots? I typically put it into the scenario, if you think about digital assistance on my device, there’s about 154 million voice enabled devices in terms of cell phones in the US today. When we think about Windows 10 devices, because Windows 10 does have Cortana on them. There’s currently 500 million Windows devices, so you think about adoption, the technology is out there and there’s a lot of users, a pretty substantial portion of people, have access to that technology. Creating the tools and taking advantage of it right now, it’s where there’s a lot of low hanging fruit.

Small Business Trends: About a month ago, there was an announcement around a little conversation between Cortana and Alexa. Can you tell us a little bit about that and what are the hopes for that kind of integration of these devices and assistance?

Christi Olson: One of the visions we have at Microsoft is to put Cortana everywhere you would need assistance to get things done, on your phone, on your PC, your Xbox, and on smartphone speakers. We want to have a partnership with other companies to make it open dialogue to make it so that you didn’t have to have three separate personal assistants, or four separate personal assistants. We want them to be able to interact and engage with each other. What was announced in early September, or I guess late September time frame, was the fact that you can, we’re developing the partnership with Amazon and Alexa to be able to say, “Hey Alexa, ask Cortana fill in the blank,” and essentially you can use Cortana and Alexa together. You don’t have to be dependent on only using Alexa on the Echo device. You can also integrate Cortana, which then accesses your entire Microsoft graph worth of data knowledge and information.

It also means that from a voice skill stand point, it might be the skill of asking Open Table to book a restaurant, asking Domino’s to order the pizza and send it to my house, or it might be the skill of asking the Lightify system to turn on the lights in my living room. There’s different language that consumers have to learn how to speak to do that. This essentially makes the language a little bit more unified. It means as a business you don’t have to create three or four separate versions of that code depending on the platform. It’s you defining the platform, it’s cross backing. It’s great for essentially the consumers and it’s also great for businesses because it means less work.

Small Business Trends: Peer out to the future a little bit. Let’s say one, two, three, even five years if you like. Where are we going to be with digital assistants and conversational interfaces, and how are people going to be using them at that time period?

Christi Olson: If I were to look five years in the future, I’d say we’re actually seeing really good adoption right now. I ran this survey back in the February time frame, where we reached out to about 2,000 people across the United States, all different age, demographics, geo locations. We’re seeing that about 80% of people have used a device at least once in the previous two to three months. That’s pretty good on the adoption side. What we saw is that they’re still trying to figure out, “Okay, when do I use it, how do I use it, how can I have it help me get things done and how can I have it help me essentially make my life easier? I think part of it, in where we’re going to be in two to three years is, as more businesses essentially create, I would say it’s a combination of skills to help take action, or chat bots to essentially say, “Hey I’d like to make this purchase. I’d like to do this thing,” having the technology on the back end make it easier for the consumer to do that next step, will take us essentially from the Internet of Things to an Internet of Actions. It’s going to take us a little bit of time there.

Consumers are also building the trust. You have to trust giving access to your data and information to the device, and so right now the trust level is, I would say it’s somewhere in the medium. It’s not super high on the trust. Consumers are willing to give access to some information, but they’re still trying to say, “What do I hold on to myself?” You have to build that relationship. In order for the digital assistant to be able to make recommendations, to be able to give you a notice saying, “Hey traffic’s really bad.” You’re on one side of Atlanta. You need to be on the other side of Atlanta in thirty minutes. You need to leave ten minutes earlier than normal because traffic is so bad, you have to give it access to data and information. That trust has to be built.

Something that we’re taking pretty seriously at Microsoft is right now, you can’t advertise on Cortana. We aren’t offering advertising and [inaudible 00:15:16] because we want to build the trust with consumers so that they will use it and interact with it. If you start placing an ad randomly like, “Hey do I need an umbrella today?” “Yes, and by the way did you know this movie is playing at 4:00 down the road?” What? You have to build that relationship to make experiences for the consumer that are willing to do and that make sense for them to add value both with how you would either advertise or give products and services, and how they use it.

Small Business Trends: Christi, where can people learn more?

Christi Olson: If you’re looking for content about Cortana, trying to learn more, you can go to If you’re looking for information about bots and chat bots, Microsoft has a free tool called, QnAMaker.AI, that helps you go from essentially an FAQ page on your website to chat bot in about five minutes. It requires zero coding skills and knowledge.

This is part of the One-on-One Interview series with thought leaders. The transcript has been edited for publication. If it's an audio or video interview, click on the embedded player above, or subscribe via iTunes or via Stitcher.

Brent Leary Brent Leary is the host of the Small Business Trends One-on-One interview series and co-founder of CRM Essentials LLC, an Atlanta-based CRM advisory firm covering tools and strategies for improving business relationships. Brent is a CRM industry analyst, advisor, author, speaker and award-winning blogger.