Episode 5: Karen Kesler and Jonathan Foster, Microsoft - Building Content Teams

May 16, 2018

Kristina speaks with Karen Kesler and Jonathan Foster, both from Microsoft, about their experience creating content for an enterprise technology company and leading large content teams, particularly the teams responsible for Windows and Cortana.

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About this week’s guests

Karen Kesler

Karen Kesler manages the Content Experience organization in the Windows Devices Group at Microsoft. The org creates content experiences focused on engaging customers, developers, and partners to do more with Windows devices and find delight in those experiences. She’s passionate about the way a friendly, human voice and tone makes every digital experience better, and has brought a fresh approach to the user interface in Windows, Xbox, and Surface devices. She and her team are leading content innovation in the emerging realm of digital assistants and bots, where “personality” plays a huge role in how customers interact with these virtual agents and how bots interact with each other. Follow her on Twitter at @krkesler.

Jonathan Foster

Jonathan Foster leads Windows & Devices Group’s Content Intelligence team at Microsoft. Their work includes defining content experiences powered by and instantiated in AI, writing conversational interactions for the virtual agent bot on support.microsoft.com, as well as Microsoft’s digital assistant Cortana in the US and international markets. He and his team are responsible for the continued development of Cortana’s personality, crafting fun, personal, and culturally relevant experiences across the globe, as well as building an ML-powered conversational layer to support Cortana interaction. Follow him on Twitter at @jonathanbfoster.



Episode transcript

Kristina: Hello again, welcome to The Content Strategy Podcast. I’m your host, Kristina Halvorson. This podcast is brought to you by ContentStrategy.com and Brain Traffic, a content strategy consultancy. Find out more about Brain Traffic at BrainTraffic.com.


Welcome back, friends, and neighbors. It’s Kristina. I have some very, very special guests with me today. They are friends from Microsoft. I have Karen Kesler and Jonathan Foster, from the Cortana team. Karen, tell me a little bit about your role.

Karen: You bet. So, we are—

Kristina: Good job. Off to a good start.

Karen: We collectively are part of a content team here at Microsoft in the Windows Devices Group. We provide content for all of our customers on how to use our devices and Windows and our services. And so, we provide good content for consumers and developers and IT admins. A whole variety of people that use technology at home and at work. I lead that team, and it’s a bunch of fun.

Kristina: Oh, so you have all the content.

Karen: Yeah. That’s why I say we.

Kristina: Yeah, right. Now you’re in charge. You’re in charge. Jonathan, whose content do you have?

Jonathan: I have a certain group of content. My team is called the Content Intelligence, and that covers a lot of things. It covers anything from the way that we can leverage artificial intelligence to serve up content. A good example of that would be understanding the context of user in any given state in a flow, and then being able to pop a message or something that we do, as writers, at the right place in the right time.

And then also, on the other end of the spectrum is probably most easily expressed as conversational design and conversational writing. That is for bots and specifically one of the big bots Cortana. We have people on my team have been creating and designing the experience of Cortana since before it was launched back in 2014. But we also do support bots and that kind of thing, where conversational design principles are in play for writers.

Kristina: So, I’m an idiot because I started off with you guys do Cortana, and then you are instead all the content. In my defense, the reason I said that is that you are coming to speak about content and IA at Confab this year.

Jonathan: Yes.

Kristina: And so, that, of course, is my narrow focus because it all comes back to Confab. That’s not true, but right now at this time of year, it’s all Confab all the time.

Karen: May first.

Kristina: Yes. Join us, won’t you? Excellent. Karen, I want to start by having you talk to me a little bit about how your content operations are set up. Can you just talk to me a little bit about structure and process and the primary tools you use? Just anything that would help listeners get a sense of how you manage the content machine.

Karen: So, we have a variety of different types of content that we create. We put stuff on the web, of course. We’ve got a lot of content that’s actually in product. I think for this conversation, it would be most helpful for me to focus on sort of what we call the consumer audience here. But if you think broadly that, that’s me at home and me at work. I’m using a Windows device or Office. I could be using Office on my Android phone, for example. So, we’re really thinking differently at Microsoft about devices. It’s not just Windows devices, but it’s people’s phones as well.

That’s a big change for us in a big shift. But some, more specifically to the mechanics on the consumer side, we have really invested deeply in the last few years in creative writing talent. That’s a different type of skill set that people often think about technical writing when you think of software companies. And so, the idea that we have creative writers that are writing in product UI text, and the words that we’re using now our UX writing. Which is a popular term in industry today. If you look at publications like Medium or blogs, you’ll see people talk more about UX writing. Which is partly the words that are in the software, but also the narrative and the storytelling around a customer’s journey through our products.

So, it’s a paradigm shift in how we think about product design. Writers are a key component of the teams that are creating all of this software. When you think of Windows, Office, Xbox, our Surface devices, we have writers that are part of the feature teams that are creating the software. And, in some cases, the hardware for those products. They’re informing the narrative of those customer journeys, as well as the actual words that customers engage with and interact with in the products. And then, of course, once you’re using the product, we’re there for you along the way with helpful tips or little pieces of information as Jonathan described in his introduction.

From a process point of view, you could imagine, let’s just call it a feature crew that’s composed of software engineers, designers, writers, researchers, and those people are all working together to create the experiences that we’re going to put in the products and give to our customers. There’s a lot of iteration on those experiences, and then there’s a lot of building the software itself. Some of that’s a strictly engineering process of course, as you might think of software development. Some of it is content tools and then content publishing, depending on what the end point is for that content.

But our organization is part of the Windows engineering team, which is an important point. Because if you look at historically, the placement of content teams in organizations of large tech companies, for example, you’ll see sometimes content teams that are organized sometimes closely aligned with support, sometimes closely aligned with marketing, and then you’ll find other organizations where it’s actually embedded into the products’ creation. That’s the case here at Microsoft. That’s been an evolution over the years from sort of around the product to in the product. Being part of that engineering team is a critical component to how we work, and how we ensure success with what we actually deliver to customers.

Kristina: Just quickly to clarify, because I’m seeing this more and more where writers instead of just being like a little pocket of writers, that things get thrown over the wall and then they have to fil in the lorem ipsum or the blanks or whatever or write this interface copy after the whole thing’s already been developed. From a functional standpoint, are writers co-locating with those teams? Do they report into those teams, specifically? Are they assigned to sprints? How does that work? Who do they report in to?

Karen: We are a central team. So, everyone is organized. If you think of organizational hierarchy, I’m the leader of, we’ve got about 150 people crossing all audiences, and then our content team is organized within our design team. So, we have a large design team and research team. We call that organization, Experiences and Insights, because we deliver experiences to customers, which include visuals that our designers create, words that come from the writers. And then we have insights, customer insights that come from our research team. That’s been a functional experiment over the last four years here at Microsoft where we have a dedicated team that’s central.

And then we’re not all in one building, but we’re in nearby buildings. But the day to day work using your term, Kristina, of like co-located, those writers actually spend a lot of time in the locations where the engineers are. And so, there’s a lot of, it’s not far walking, like Microsoft’s got a big campus but everybody finds a way to meet together. Sometimes we use Skype, like we are today. But the co-location of the work is a dedicated feature team in which the writers and designers are. Just think of them as embedded, as part of that V team, if you will.

Kristina: Interesting. Got it. Good. Jonathan, how does that play out with your team?

Jonathan: To be clear, I am on Karen’s team. I didn’t state that earlier, but it’s easier to understand. So, I am delivering a certain kind of content in Karen’s larger organization. Just like she said, we have deliverables. We sit together as a team, the writers and some of my team goes over and works on with some of the Shell team, we call them, the Windows team, to find how best to support the needs from the writing perspective.

And then another part of the team goes over and works with engineers on our support bot. Sometimes that’s done remotely, meaning like right here where we all sit together. Sometimes you go not far across campus. It’s not a huge campus but go and sit in meetings and studies and all kinds of stuff, and then the Cortana folks, same kind of thing. We sit together, but then we spend a lot of time with that team as well. Over time, you build deep relationships with these folks. One of the things that I think is really great as many of us sit right here in the same space, different office but same space, with the design team. And so, we’re able to really get in tight partnerships with those folks. I guess one of the key points to what we do is to be able to develop those relationships with our partners deeply, as a centralized team.

Kristina: That’s fantastic. And then I talk about that really regularly in terms of content strategists’ jobs and rules, which is to connect the dots between the designers and the developers and the researchers and so on. Because ultimately, the experience is going to be fueled by that content. So, it sounds like your writers, your UX writers are also playing a real strategic role in terms of how the products are being designed and built.

Jonathan: That’s accurate from our perspective. One thing that I would add is one of the interesting, I guess it’s best to say perspectives that we gain is kind of the overall view of products and how they integrate together. Because we are kind of driving these relationships with partners across products. And so, we have more of a unified perspective of what that flow or that experience would be.

Kristina: Excellent. Karen, you mentioned working with creative writers. Tell me a little bit about the background of some of your team members. You’ve got 150 content folks. Surely, they didn’t major in technical communications.

Karen: That’s a great point, right? I think of, sort of, we could divide it in thirds. We’ve got a couple thirds of the organization that are our developers, as well as writers, right? So, they can actually write code samples for the content that they’re creating.

And then on the areas that we’re talking about here with Jonathan, we’ve specifically focused on people with theater background, fiction, journalism, creative writing, people that have been copywriters sometimes with marketing organizations, people that can be both concise and creative and write, if you think of journalism, catchy headlines, right? The types of things that we all like to click on.

That was a functional change that we’re a few years into, but the return on the investment to the business has been demonstrable. The type of copy that we have in our products, the way of working that these people bring to the conversations as Jonathan, I think used the word, narrative. We’ve been talking a lot about storytelling is really again connecting. And you, Kristina, said connecting the dots, which I was like, “Yes, she said that first.”

Kristina: I say that 10 times a day.

Karen: Okay. We think of that a lot, right? Part of what some of the challenges are with software products are you have siloed features that then we provide the customers and hope they figure out how they all work together. Many companies have gotten better that. Google, Apple, certainly Microsoft made progress there as well.

This capacity and this capability in the role that we bring into those conversations is, one of the biggest things we do is connect those dots. Whether we’re helping feature teams learn what others are doing, it’s sort of the tyranny of the urgent, everyone’s busy every day. So, the content team and the writers specifically sort of serve as an umbrella view that can help connect the engineering teams, the features, the experiences. And then actually create the narrative across those things. Jonathan has a couple of people on his team, maybe might be useful to have him explain a little bit of where they’re actually serving a function that’s somewhat new to the software development phase. Which is embedding with these feature teams and helping them tell the story of the feature that they’re going to build, and sometimes involves creating multimedia along with that storytelling.

Jonathan, you might have a good example of that the talent of those people. I’m thinking of a few people specifically.

Jonathan: Yeah, exactly. As Karen said, we’re calling that internally storytelling. Normally, our focus as writers was always on the customer touch point. But now we’re seeing there’s real value and we can impact this connection of dots and bringing that to the table through internal support. That is starting off with just people having ideas and wanting to push ideas, but how do we articulate that in a way that makes sense both as we go down the path of development, let’s say of before that. But also, then it extends into we can inform the marketing storytelling around the product, once it does reach the customers.

But it starts by really kind of embedding yourself with folks who have these ideas, and working with them on the whiteboard, wherever, and just saying, “Okay, how are we going to express this?” Writers are becoming more and more valuable internally to Microsoft for that function, and it’s exciting.

Kristina: So, the biggest question I get asked is, how do I sell the value of content and content strategy into my organization? Because this point that you make about writers becoming more and more valuable within Microsoft, I’m going to assume that wasn’t always the case. Can you talk a little bit about how that change came about and what kind of, whether it was internal education, or change management opportunities? How is this evolving?

Karen: You’re right. It hasn’t always been that way. I give some of that credit certainly to some of the leaders here at Microsoft. We’ve had some engineering leaders that have leaned into providing design-led experiences. I’m thinking of the customer experiences as opposed to leading with a technology, if that makes sense.

If you look back over 10 or 15 years of technology development, everything we look at ours like everything moves so fast, right? And so, you often have the technology that’s driving the experience. In the past few years, we’ve had some leaders say, “We need to sort of change the conversation, so that we’re thinking more about that customer experience and what that should look like.” And then we’ve had some opportunity where you have writers that are part of the conversation, and it’s a fortuitous relationship where the need is there, the talent is there and open mindedness to thinking differently around how we start the process, move through the process and bring that to the conclusion, that has had the opportunity to sort of change like people think of it here.

To that question that you get asked often, it’s a difficult one, depending on what the environment is. There’s always a change management component that sometimes you bring to the table, and some of it’s just focusing on the work itself. Which seems like an easy answer, and I don’t mean to trivialize it. Yet, offering sometimes like, “Hey, let me take a stab at just writing this story down and putting some craft to it.” And you, you invest your own time, you bring that to the table and then other people see what the value is there. That’s one of my biggest experiences is that work often sells itself, and sometimes you have to muscle in in ways that you don’t usually. Some of that’s by offering to help. Like “Hey, let me just take a stab at this and put it down into words.” People see that creativity in that need and self-select that, “Wow, I can’t do that. You got any more where that came from?”

Kristina: Jonathan, do you find that your team needs to muscle in on stuff? Or people pretty well settled that this is important, we need this, we’re going to lead with this.

Jonathan: It varies. Sometimes we can walk right in early on, other times we have a lot of advocacy ahead of us when we need to start diving in with some partners. It just depends on who they are and what their perspective is. It’s changing though, but still we do have to be advocates on behalf of our own work. From Karen’s team, we do a lot of advocacy for the voice of Microsoft, we call it Voice and Tone, and now we’re adding personality in there for these conversational experiences. And, we continue to go around and preach to the choir where that makes sense for other writers, other designers that agree we need cohesion here at Microsoft. Everything has to reflect that Microsoft brand. But also, to new people, so they can see.

Oftentimes, the advocacy is about just awareness. It’s an awareness move. Some people don’t know that they even have access to writers. When they do, then they brighten up and they think, “Oh, my gosh, we could do all kinds of things.” I would say, one of the things too that I would add to the equation is, we really, we really look for data opportunity to support the work. Whether that’s external or internal, we test our own work and then we bring that to that conversation, saying, “Look at this is how we move the needle by changing the tone of this language.” Or, “By using this kind of voice in a bot, we can see deeper engagement by these numbers.” And numbers of course help and they have to be accurate and genuine.

So, we work hard to find those to measure what we’re doing, of course, and to change what we’re doing if we see an opportunity to create a better customer experience. But also, to keep reminding people that we can add value that is measurable. And then of course, there’s a large conversation going on. Because as I’m thinking that people will be listening to this and saying “Yeah, yeah, this is a tech company.” That’s true, but there’s a larger conversation that’s going on that I like to talk about a lot. Which is as tech continues to just be the next era and technology influences experiences across all businesses, we’re going to see a need for more human centric design and writing and engineering, and that’s of course, we’ve been saying that for years.

But one of the things that folks from the humanities side of the world, and that’s us writers, we can bring the human perspective. I predict, and I’m not the only one, I’m basically capitalizing on many great thinkers, but I predict that that’s going to play more and more of a role. As a result, we’re going to capitalize on that need. That need to bring the human touch to these experiences, as opposed to just ones and zeros. And then that’s something that I’ve discovered is super valuable when we do bring more writing from the artistic side of the discipline.

Kristina: That’s outstanding and exciting. There was an article that I cut out of a magazine back when I used to do those kinds of things, in the early 90s. In the early 90s that sort of said, 10 jobs that will be around in the new millennium. They said, “Oh, everything’s changing, the internet’s going blow things up. Blah blah blah.” But one of those 10 jobs was storyteller. It’s so cool 20 some years later to hear, yeah, this role is continuing to gain prominence and will be ever more important as we continue to elevate conversations amongst each other and with machines. Creepy, but real.

Jonathan: Well, and to keep it from being creepy and to keep it real, we need human contact there. I’m super passionate about that. Actually, you just reminded me of something. I remember reading something that David Mamet had written in a dark moment where he was saying, “I will always have a job. Even if we have some sort of apocalyptic moment we’re all sitting around a fire somewhere camped out, I will still have the job to tell stories.”

Kristina: That’s right. The playwrights among us will survive.

Jonathan: That’s right. Storytellers.

Kristina: Exactly. They’ll be the ones getting to the choice pieces of wild horse that we all end up eating or whatever. God, talk about taking a dark turn. Just leave it to me.

Jonathan: Whoa, whoa, whoa.

Kristina: Yeah, hey now, back it up.

It’s been a long winter. What can I say? I have one other question I wanted to ask around the topic of governance. When you have 150 content people who are crafting content for so many different touch points, both you know internally and externally and across different content media and technologies, how do you maintain consistency in terms of, specifically around that voice and tone structure that you mentioned?

Karen: Another great question, thank you. That one is, governance is a tough word and it’s reemerging here in a couple places at Microsoft. But we’re talking about what we’re trying to accomplish behind that word. I’ll attribute a couple things from the voice and tone personality work that Jonathan mentioned, and some of that we’ll share when we see you at Confab, has made a big difference in helping people ground the thinking about their content really getting the conversation to our organization, and we embrace our own family, right?

So, whether it’s a developer or an IT admin, we talked about how these voice and tone principles are important to creating a personal touch with our customers. Because everybody wants something that’s easy to understand, even if you’re on the more technical side. So, that’s the one piece around the words and the expression of those words, are different writing teams all really lock arms around our voice and tone principles. We embrace the role of leaders at the company, certainly partnering with other content teams at the company. There’s only a couple other large ones like ours.

And so, that’s an important asset that’s both thought leadership and practical application in the products and then in anything that we give to our customers. And even as Jonathan said in those internal communications, we want to walk the talk, right? If we’re really going to be warm and relaxed and friendly with our content, we should be that in our email, we should be that in our personal conversations. So, that’s a big piece. The other thing I’ll add is that being part of the design organization that actually creates the designs for our products, that actually helps us bring cohesion across all of the content experiences as well. Because as we all know, content isn’t simply the craft of great words. It involves, particularly in this day and age, multimedia and infographics and all types of visuals. Videos that people look to when they think about content.

And so, being part of a design organization that is setting the principles for the design language that is in our products and the expression of the visuals in and around our products, helps us also bring cohesion across our content experiences. Ultimately, it’s leaders like Jonathan in those teams that are doing sort of the self-checks. We have a process here that we call CRITs. So, you’ll have a UI CRIT critique, we’ll have a content share out where we’re looking at content and walking through things together, getting feedback from each other, et cetera. That helps also bring some cohesion. So, that process is replicated across various teams as well.

And then it’s about empowering people. It can’t be something that you govern and police every day. It’s got to be a trustful environment in which we trust each other to do our own work and attach that work to these principles that I just spoke about. Like let’s go do great things together, and that’s that culture environment that we treasure and is really important for us to nurture and foster.

Kristina: What’s so interesting is that you totally used the words “govern” and “police” in the same sentence, kind of mean the same thing. That’s very interesting to me because I find that when organizations, the term governance first gets introduced, that’s exactly what people think. They’re like, “Oh, governance. That means people are going to try to govern my work and police it and smack me down. And I don’t want that because nobody understands my content the way that I understand my content, of course.”

When we talk about it, we really talked about governance as providing more of a common foundation for content processes and principles and so on across an organization. And really, that sounds exactly like what you’re talking about, so that it’s a healthier thing that does empower people versus something that polices them.

Karen: Yeah, and I think it’s just words, right? Like we’re all wordsmiths, right? So, we get it. You use a different word and you get a different response. We’ve seen that in spades here at Microsoft. The word “principles” you just used, and I think that’s a good one. Is you start by laying down principles. What I like about that word is, it’s objective. You can say, ”Hey, these are principles that we arrived at.” You can explain the process by which you arrived at them, but there isn’t a huge subjective or opinionated layer to them. Once you get agreement on the principles, then you can all attach them, and you also use the word “foundation,” which is fantastic.

So, yeah, that word governance is a tough one for me. It implies something that feels less positive and ... But principle’s like, “Heck, yeah, let’s attach those and let’s go do great things together, based on those things.”

Jonathan: Just to add on to that, we have the alignment with our fluent design system here. That’s a design system that I encourage anybody that’s listening to go research. In there, is this fundamental principle that it’s not a downward push of, like you say, policing, do these things. But rather, these are our principles, you work with us to see how we can adjust those so that they apply to you, and you can succeed. And then it all feels like it’s all in the same family. It’s that inclusive approach, rather than the policing approach that we really have to be thoughtful about, mindful about, so that we can gain partners.

But I do want to address something too, that we’re very clear about with our writers is, not that this is the wrong thing to do, but if you want to be empowered as a writer, you really need to think about how precious you are about your work. You said, "My content that only I understand," and that’s fine, because we want that kind of ownership and that kind of passion around what we’re doing. But we still need to really express the power of not feeling precious of being flexible. And so, we’re trying to be flexible on both sides.

Kristina: That’s fantastic. I think that that’s a really important skill for any content professional to have. Is do not hold on to the emotions or the politics of content and be able to continually focus on business goals and user needs.

But here’s the question I want to put to you, though. Is that coming back around to this idea of, and if you want to call it policing, that’s fine, but ultimately, what happens when content comes out and it’s crap? I mean who gets to say no, this is not good enough and this is not going out?

Jonathan: I would say, first and foremost, who gets to say it is the customer. That’s what we really want to see how our work resonates with the customer. So, we watch for feedback. And then internally too, all feedback is good feedback. Whether or not it’s crap or not is subject to some deliberation after the fact. Sometimes it’s obvious, sometimes it’s opinion based, right?

Kristina: Is this crap?

Jonathan: Let’s ponder this. It’s crap.

Kristina: Yeah, exactly.

Jonathan: I really like to think that we’re testing our content in the customers’ world. In the world that they are experiencing our words. Just like design. That’s why we work so closely with research here in our organization and across Microsoft.

Karen: I think one of the biggest things I see where we’re continually trying to remind ourselves to pause and improve is particularly when people get so busy, we’re hitting deadlines. We sometimes fall into patterns of sort of formal tech jargon sometimes. It’s that constant check of like I certainly send feedback, or I at least try and ask questions like, "Hey, help me understand how the decision making around some of this content." Or, "Does this reflect our voice and tone principles?"

It’s particularly when we get into trying to describe complex UX flows or technology that we have to again pause and it’s that craft of rewriting. Can I make this simpler and easier to understand? And when you’re in a hurry and you’re moving fast, you sometimes fall back into the easiest patterns. That is a place where I think, from my perspective, I find that we iterate more when we’re saying like, "Whoa, does this sound like what we really want it to sound like, and can a customer understand it?" That’s got to be an iterative thing that we hold ourselves up to.

Jonathan: Also, something that you mentioned, Karen, that I think is important that we learned a lot with the work that we did on Cortana is the necessity to slow down. You really are just champing at the bit to go faster, faster, faster. Get more work done because it’s a mountain ahead of you of what needs to be done. Sometimes you have to look at your priorities and think, "Okay, is this a point where we’re going to slow down?"

And so, when it’s either high customer hit or something that may resonate with certain sensitivities, let’s say, you really have to be willing to slow the process down despite what other people are saying, hurry, hurry, hurry. But you have to be selective too, because no business would be able to support a bunch of writers going slow.

Karen: Exactly. Yeah, you can’t you can’t stop the content train while you think carefully all the time. That’s for sure.

Kristina: Well, you’ve both been really generous with your time. Thank you so much. It sounds like you’re doing just terrific work with your team there. We can’t wait to hear more about it at Confab in May. I really appreciate your time. It’s been a terrific conversation. So, thank you.

Jonathan: Thank you.

Karen: Thank you so much for having us really, really fun.

Jonathan: Can’t wait to be there, too.

Kristina: Yeah.

Jonathan: It’s going to be great.

Karen: Woo-hoo, Confab!

Jonathan: Yay, Confab. Go Confab.

Kristina: That’s right.


You’ve been listening to The Content Strategy Podcast. I’m your host, Kristina Halvorson. This podcast is brought to you by ContentStrategy.com and Brain Traffic, a content strategy consultancy. Find out more about Brain Traffic at, of course, BrainTraffic.com. Thanks, and we’ll see you next time.

About the podcast

The Content Strategy Podcast is a show for people who care about content. Join host Kristina Halvorson and guests for a show dedicated to the practice (and occasional art form) of content strategy. Listen in as they discuss hot topics in digital content and share their expert insight on making content work. Brought to you by Brain Traffic, the world’s leading content strategy agency.

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