‍Larry Swanson: It was so gratifying to see the long list of unanswered questions at Button and I'm really glad we get to come back to them. One of the questions in the queue asks: in cases where you're trying to create a unified content strategy across multiple content teams within an organization,  are there specific tactics that you use? 

Eileen Webb: My general approach to essentially de-siloing is to just invite a lot of people to meetings. See if you can set up a scheme where there are meetings that don't have multiple teams represented and don't have multiple viewpoints represented. Content folks, bless our hearts. We're always talking about … did I get invited to the meeting early enough? Did we start talking about writing early enough? Be the change you want to see. Get the engineers into your planning sessions. Get the content marketing managers and your product marketing folks into your conversations. It’s almost like you want to assume curiosity. We tend to be very curious people. Assume that other people are curious and kind of treat them as if they are, even if they haven't exhibited that yet. And see if you can help prompt that in them. 

Patrick Stafford: I’ve had success with running critique sessions across different departments, which is a great way of bringing people together. It's not the hard strategy of “let's talk about a unified content strategy.” It's a softer way of getting everyone to understand what everyone else is working on. And you'll soon find, I think, if it's done well, that you'll see people beginning to anticipate and accommodate and even match things that are happening in other areas. There are a bunch of large organizations that do that. From what I understood recently, Meta’s critique sessions for their content designers are pretty cross-departmental. Although I think they're a pretty unified content design practice. Anyway, I've certainly seen success in doing that, and it's a good way to get people on the same page before you even start doing some of these larger projects that sets you up for success.

Larry Swanson Similar to what Patrick just said, I stole this idea from Tamara Adlon. I heard a talk about this many years ago. That I never go to a meeting where I don't know the answers to all the questions that I'm going to ask. That you do a lot of one-on-one meetings ahead of time and other research and prep work so that you're prepared. I'm still surprised once in a while, but generally you try to go in with a good understanding. Tamara takes it a step further, and I'm not as good at this as she is, but she'll use that knowledge in sort of assertive ways to really push forward decision making processes. But I think that preparation is really key. We’ve got another question from a Button attendee. Do you find it challenging as a writer to be included in the very early planning discussions? Sometimes that's where the unified content approach starts, ensuring that there's a shared vocabulary long before a single mock up is made or a string of code is written. It kind of goes back to that early on thing that you talked about. 

Eileen Webb: Sometimes in work environments, we can be … the word ruthless just popped into my head, which is maybe a little strong? But we think … is this relationship going to be useful for me? And I think that one of the things that is most helpful if you are trying to work across teams, across departments, across everything, is to cultivate a belief that every relationship is useful and every connection that you make, and I don't mean every business relationship where you know what their job title is. I mean conversations that you have had with this person about their cat who walked in on the Zoom call that you were on. Those kinds of things, that's what makes it so that it’s easier for you to assume the best of people, because you know these people and you think, “she’s not actually a jerk, she must be having a weird day because we had a good conversation before.” It's easier to butt yourself into something in a way that could be awkward and rude if you didn't know the people. But if you know those people, and you know that they will give you the benefit of the doubt because you reinforce that “we’re all friendly here.” But you have to get to the point where you feel like you could interrupt someone and not have them think, “oh, she is being a jerk.” Instead you could interrupt them and they would know that you wouldn't interrupt unless it was like a thing that felt important. Cultivate that level of relationships with people across the organization. That’s not an immediate fix for a project starting. But start that now and it will come to fruition at some project in the future. It's less of a reaction to a current project but more of laying the groundwork for things to be easier for you as you move forward.

Patrick Stafford: I'm going to interpret this question a little broader, because I think what it’s asking is, do you find it challenging to get invited into the early planning discussions? I’m sort of interpreting that literally. Something I hear from a lot of content design managers is that, yes, it is a challenge to get into those early stage meetings, but a lot of the time when content designers get there, they're a little bit like a deer in the headlights. They think: I'm here and I actually don't know what to do. I haven't done this before. We talk so much about getting a seat at the table and getting in the meeting, that sometimes when you finally get there, you don't know how to approach creating something from scratch. Creating that unified strategy with product, with marketing or whatever. There's something to be said for, in that context, understanding the broader context of the company in which you're working and the product that you're working on. So a lot of content designers will be given screens and given flows or in charge of a feature or whatever, and they will do very well. But something I've heard is that 0 to 1, that sort of nothing to creating a feature or creating a flow or creating a strategy is a little bit more difficult. It really starts by understanding what is everyone actually trying to achieve here, which seems like a very obvious question. The answer is not always obvious. So, what is the actual goal that we're trying to achieve? The goal is not to create some awesome content. The goal is we need X% of market share by the end of this quarter. We need to increase our subscription rate by 5%. That anchor will then guide every other decision you make, whether it's content related to what you're doing in specific designs. When you're having conversations with people in other departments, you can always come back to, well, just remember, our goal is we need X% growth by the end of this quarter or by the end of the year. So I think, yes, getting into that meeting is absolutely a challenge. But just be aware that when you're in there, just be focused on trying to understand what's the actual goal? The actual goal is never just creating some great content.

Larry Swanson: Patrick, I love that. I've never thought of that … about us as the dog who finally caught the car, you know? And now we got it. Eileen, I know you've thought a lot about this kind of stuff. Do you have anything to add to that? Other tips or techniques? 

Eileen Webb: Take that idea that Patrick just shared and expand it also to the people. Do you know how your manager is getting rated performance-wise? Do you know what their OKRs are? If you're in an organization that works on Agile and sprints, do you know how many points your engineers need to do in the next sprint? And do you know what you are asking of them when you ask them to shift their process, or when you're asking them to include you in a review cycle? Patrick spoke about asking: what is the business doing? But that same level of introspection of … what is this person scared of? What are they trying to prove? What are they trying to demonstrate their skill at? Where can I support them in their goals, that will also help move my goals? If you approach it with creepiness, it's very Machiavellian. But if you approach it from a place of: how can we all win? How can we all succeed here? 

Patrick Stafford: I see it in the same way as playing a video game. So, I play video games with my friends. And a lot of the time in these games, you'll have a daily challenge. You're playing a Rocket League or something and it'll say, get ten goals. And we help each other get through all of our challenges. So I'll say to my friend, what are your challenges today? Okay, let's go. Let's help you get those challenges and let's help you get those challenges, and then they'll help me get mine. I think it's easy to help each other when everyone's goals are just on the table. And I've worked in organizations where everyone knows everyone's OKRs and they're all public, and you can actually see what everyone's individual OKRs are. Other times they're not, and other times they're private. I think to your point, Eileen, just asking people. There's nothing inherently problematic about knowing everyone's goals. I'd say if you're in an organization where knowing that kind of stuff is taboo, then that's probably not a great work environment. I agree with your approach. How can we all help each other succeed? I think that's a great mindset to have.

Larry Swanson: As you're both talking, I'm hearkening back to when you were talking earlier, Eileen, about how ruthless you are about cultivating relationships. And I think relentless is maybe a slightly better word for that? And then, Patrick, to what you're just talking about, it's not like teamwork. It's just knowing what's going on. And that's another kind of high level concept of doing what it takes to set the environment, that permits things like unified content strategy to manifest. Does that resonate with either of you? The notion of stewardship is what I'm thinking about.

Patrick Stafford: Yeah, I think the way you just framed it: it's not teamwork, it's just context. It's the stuff before the teamwork. Right? It's setting the table. I think that enables everyone to just know that they're working on the right things. You can't do anything unless you know all of that.

Larry Swanson: Eileen, does that concept of stewardship underlie any of your thinking? It sounded like it was maybe not difficult for you because you're such a people person, but may be difficult for some people?

Eileen Webb: I do think part of this is figuring out how to make it work for yourself with your own neurology, with your own behavior patterns, which is going to look different for every person, right? Like what makes sense for you? If you're in an organization where OKRs are secret, you could be the person who's like, “let's all share our OKRs!” Or you could be the person who's just like, hey, can you share with me what you're trying to get done by the end of the year? I would love to know the bigger picture. You don't have to use those words if they are going to be stimulating for people. I think there's a fine balance here. If you are a person for whom stewardship of the organization, on a larger level, will be something that helps you as an organizing framing and helps you keep your motivations and your values in alignment, that's great. And also, like Torrey was sharing earlier, from that wonderful talk that Kesavan gave at Button, do you need to disassociate from your work and your outcomes a little bit? That's totally a personal thing for some people. You might need to actually separate yourself from the importance of the outcomes of this work in order to stay healthy. And other people have enough of a boundary that they can also grab on to this work. And both of those are fine, but it's an awareness of self, of what is going to work for me? You can't martyr yourself for the purposes of your unified content strategy or for anything really. Don’t do that. It's not a good choice. And so how do you find a thing that works for you that also is contributing to the larger whole?

Larry Swanson: Is that like putting on your own oxygen mask first?

Eileen Webb: Yeah it is. I also think it's a level of … a decision to do introspection and a decision to understand that there's only … sometimes we talk about “my work self” and “my personal self.” There's only one of you. The idea that you might be able to have some sort of separation or partitioning is a very polite fiction. Maybe sometimes an impolite fiction. And so understanding where it is that you get caught up in things, understanding what your rabbit holes and shiny squirrel things that will distract you from your goals. Understanding where it is that you might, in what context you might, make decisions that are misaligned with your values, so that you can recognize them when they pop up. That feels to me like it's personal work. That also it makes your work better because it makes your life better.

Larry Swanson: You know, Eileen, I met David Allen a couple of years ago, the guy who wrote the book Getting Things Done. And I got surprisingly emotional when I introduced myself to him because I realized in that moment that he had that insight. And I don't know if any of you read this book, but one of the things he talks about in there is like, it all has to get done. You know that you can't separate out the work and the personal column. It all has to get done. Let's go to our next question. How do you deal with stakeholders who are adamant in their views of content or UX writing ideas, but don't seem to listen to overall best content strategy or UX writing best practices?

Eileen Webb: I feel like that ties exactly into what we were just talking about. Why is it so hard for us to hear someone doing something wrong? There are best practices. There are also my favorite practices which are not the same thing. And there are actually very few best practices in every context, in every circumstance. And there are very many things that I like doing this way, I think it’s better this way, and I think it reads better this way. There's a whole aspect of this question that I think is about … how can you find ways to regulate your own nervous system and let this not be so reactive, so that you can be creative in how you talk to this person? I am absolutely confident that we all have the ability to figure out how to reach them and to say there's a disconnect here, how can we find it? How can I find the common ground with … what’s the story or the analogy or the data point or the research or whatever that will help here? But if we're stuck in their wrong and I have the right answer, and it's so frustrating that you're not listening to me, that's seven-year-old you who’s like, “the adults never listen to me,” which was absolutely true and is not the same thing as what's happening now. And we have to learn to separate those things. Otherwise we just get caught up in some kind of attitude.

Patrick Stafford: I'm laughing because … there was a post on the UX writing subreddit the other day, and I thought it was super interesting. It was someone who was saying, and I don't know who this person is, they're anonymous. So they work for a home appliance company. And so they're working on the app. And they said in their post, I'm getting a lot of pressure about changing the voice and tone to make it more fun. They said in the post, well, users haven't complained about it. And actually, users don't want fun language when they're using their appliance. They just want to get it done. And I was just thinking, are you sure about that? Who says? Do the users say? So, I think it’s a good point to start with the idea of, as you put it, what are your favorite practices versus best practices? I also think engaging with people who have some views or some beliefs about our practice that maybe don't line up with our own, asking questions is a great way to really probe and understand how they think. Because when I'm interacting with someone who clearly has very different beliefs than me, I just want to know what's the logic behind what you're doing? And maybe there is no logic. Maybe the source of their frustration or their misunderstanding is rooted in personal experience. One of the best pieces of advice I ever got from a manager was if you're in a frustrating conversation, don't make statements, make questions. So, why is it that you believe that? Where have you seen that before? Have you seen what type of effect there is when we use that type of copy? And doing so, not in an aggressive way where you try to make a point, but really trying to understand where your belief or philosophy of UX comes from. Because it might be rooted in something that they have personally experienced. And then you can point out and say, “Yep, I totally understand why you would think that, given that context. But in our situation, do you think that maybe this is a little different?” You don't have to win. You don't have to convert people to the church of content design. And maybe you'll find that your beliefs change as well. I think asking questions to understand where people are coming from is the best strategy.

Eileen Webb: If you want a very practical tactical answer here, there are places where you can say let's try it both ways and see which one performs better, whether you have a proper A/B testing setup for whatever your context is. Which one makes more sense when we're doing user testing? Which one leads to more confusion? If there's a way that you can do that and do it genuinely. Like Patrick said, you have to be open to the idea that maybe some people do want a funny dishwasher. Don't doctor the tests. Be genuinely like, alright. Maybe, we can figure this out. I mean, there's a lot to be said for which hill do you want to die on? Do you want to die on the Oxford comma hill? Or do you want to die on some hill that's more useful? It's not objective, right? There is not a “best” content design thing. There is not one right way to write this thing or to do this interface or to put help text on this form. We're all just making stuff up. This industry has only existed for 16 years. It's not real. We're making everything up. And so deciding whether that's where you want to … this sounds like a gross thing to say, but … spend your political capital. Is that the thing you want to fight on today, or is that a place where you're like, you know what, I think this probably doesn't matter, and I think it would be more useful to have this person feel like I am hearing them. Because I know we're going to have a more difficult conversation when it comes to thing X that's coming down the pipeline, and I want to go into that with everyone feeling really good. And that's a strategic choice you can make. That's a meta strategy about your work, not just a strategy about this particular UI.

Patrick Stafford: I think sometimes in UX, we can be bogged down in a particular set of thinking that's rooted in: what’s the problem we’re trying to solve? And that's a great question to ask. I also think we need to think beyond that sometimes, because if we only think about things in terms of problems, we never think about things in terms of opportunities. And content design has a lot of opportunities. Sometimes that might mean flexing our tone a little bit or flexing the way we do content a little bit. And if we only think about things that are explicitly problems, we don't have the opportunity to lead. It's kind of like looking at statistics and doing some polling and seeing that only 45% of people agree with this, so we shouldn't do that. The other way to look at it is, well, only 45% of people agree with this. We have more people to convince. We need to go out and we need to spread our message more. We need to go and lead. So I think there's an opportunity for content designers to to really expand our thinking about what user interface text looks like and how it can act. And really, this is kind of like an offshoot of marketing, right? This is a larger conversation. But I think sometimes we tend to think that, okay, marketing is over here. UX is over here. No, they're part of the same goal. They're part of the same engine. If we think about the way that we do UI text as an opportunity to lead, it can make these conversations a little bit easier to have.

Larry Swanson: I gotta say, I love the little pivots that each of you just made around the kind of pragmatic approaches to this, like seeing opportunities in problems. And Eileen earlier when you talked about the best practices versus my practice and then later proposed a very pragmatic way to incorporate testing. I love that both of you are driven completely by curiosity. Patrick is always asking questions. Eileen is explicitly talking about curiosity. So thanks both for that. Torrey, our lovely Button host, has a question in the chat. She asks, how important are the tools for your unified content strategy? If you have any to recommend, what's your favorite “spreadsheet in a suit” as Jane Ruffino calls it, for promoting and advancing unified content strategy?

Eileen Webb: I'm a consultant, so I work with a zillion different organizations, and my favorite tool is whichever one they like the best, which is in some ways horrible for me because sometimes I'm doing work in OneNote and Teams because the organization is a Microsoft shop. Other times people are all-in on FigJam and other times, it’s Miro. And I’m thinking, I’m good in Mural. You need some sort of way to organize information in a structured way, which is often a spreadsheet. It could also be a database or something. You need something to do visual stuff because no one but us wants to read a spreadsheet. So you need some way to represent it not in a spreadsheet format. And maybe if you're using Airtable or something similar, there are fun little plug-ins that can make a spreadsheet turn into something that is visual and interesting. I work on Zoom, right? We are all remote and distributed. Now, my favorite tool is a whiteboard. I miss the days of standing in a room with someone and doing a crazy drawing on a whiteboard because it was the easiest. No one got confused about the fidelity of my dumb wireframe that I had just sketched on a whiteboard. People gave me feedback about the concepts, not about what color pen I chose. And so I'm always looking for tools … I want the clarity of information behind the scenes, but what's the biggest, best equivalent to a dumb old whiteboard?

Patrick Stafford: You actually can't see it, but off screen I actually have a whiteboard that I bought because there's something useful about standing in front of it and physically writing something out and crossing things out and making connections. I agree. Don't try and force people to change their behavior when it comes to tools. I think there's a larger conversation to be had about the tools that companies use and getting them to move to more affordable options. That's sort of a long-term strategic play that you can make. When it comes to the immediate work, I think about where are people doing their work, where are people living? If there's something to be done that can't be done by an existing tool, I think you have to prioritize accessibility. And obviously, I mean, accessibility in all of its forms. Is it not just easy for everyone to use, but can it be accessed? Do you need accounts? Are there privacy considerations? Anything with the fewest clicks, and anything where you can see everything all at once. The biggest thing is the ability to share it, because things will be shared in documents and emails and so on. So you really just want something where someone can just click a link and just go, “Yep. There it is.” And also the ability to have conversations and comments. So anything that has that sort of element to it, as much as can be contained within the tool itself, anything where you have a conversation that's happening separate to the document is always going to be an issue. Some of the most successful initiatives I've seen have been from companies just using a Confluence page. It's less about the individual tools you use and more about the principles by which you use them.

Larry Swanson: I 1,000% agree with everything you both just said, but I'm going to take this opportunity to revisit a rant from a few years ago, a talk I did here at Button about the lack of content management systems for UX content and design system content. If there's any CMS vendors or entrepreneurs listening, can you get on that, please? Let's go to another question from an attendee. They say: I had a conversation with a senior content designer who drew a clear line between content design and content strategy. I thought content strategy had evolved into content design for the most part. What are y'all's takes?

Eileen Webb: I have none of take. Man, labels? For a profession where I spend a bunch of time being detailed about people's labels, I just can't care. What are you doing in your job? What are the outcomes? I think the thing that gets me is that, whatever label you use in your team and your organization, is not transferable to anyone else's label in any other organization. Because it's all being made up, because this industry is only less than two decades old. What are you doing? Do you enjoy it? Can you explain it to someone who isn't in your space? People sometimes, you know, at completely different organizations or different events will ask me what do you do for work? And I'm like, well, can I think of an analogy that makes sense for this person? And other than that, none of these labels are helpful for me.

Patrick Stafford: Scott Kubie has a good take on this. I can't remember his words exactly, but his approach to labels and titles is that it's all really sort of secondary. I think he even wrote an article about it. So I highly encourage people to Google it. But, yeah, I agree, it is so unique to every organization that it really is not a conversation that you can even have in the abstract. If you were going to push me and make me decide something, I would say that content design is an element of content strategy, but, ultimately, eh. I don't think it matters all that much.

Larry Swanson: I have to chime in on this one because I currently work in the field of semantics and, ironically, both content people and semantics people just have a horrible time coming up with words to describe what they do and agreeing on them. It's lovely how hopeless we are, but how effective we are at the same time. But I also think that kind of gets back to the pragmatism that both of you introduced earlier about talking in people's own terms about how they do things. And that's probably the most useful thing if you can all agree on a concept of what you're going to do or what you're talking about, labels just become secondary. It's almost like a translation and localization task at that point. Let's jump to another question. What does it mean for an org to approach content in the same way? Is this a macro level mindset or how do you decide on it?

Patrick Stafford: One thing I used to hate is, when we're working in a large organization, where every organization will have its values. Right. And they'll usually be quite bad. We're helpful, we're friendly. When I worked at MYOB, we had six values and I can't remember what they were. They had this philosophy or this rule where at the beginning of every departmental get together, you had to explain how you are showing the values. And you could reward people. Yes, it is very corporate. Yes, it is very stilted. But there’s something to be said about deciding on philosophies and just repeating them all the time. And so you eventually get to a point where people could rattle off what those principles are and what those philosophies are. And so I think there is something to be said for deciding on whether it's a phrase or a set of principles or something that people can run with and then just hammering it in all the time. Not to get political, but if anyone has been watching the mayoral election in New York, Zoran Mamdani ran, I think … like we can debate some policies inside his campaign … was really notable for the fact that, every time people would ask him questions, he would always come back to, well, how can we make the city more affordable? How can we make the city more affordable? And they would ask him a question, and he would always try and sort of put it back into that message. And there's something very, very effective about just deciding on something and running with it. So I think if you're going to approach content in the same way, I think it is a macro level mindset, but I think it's about getting everyone to agree on that same set of principles and then infusing them in everything. They're on every document that you create, they're on every sort of deliverable. They're on every presentation. When you're creating UI content, you're making content designers say, okay, how are you supporting the content principles in this content that you're creating? I think that is an effective way to go about it. Obviously, it has to be done the right way.

Eileen Webb: I think one of the side benefits of doing that kind of ever presence is also … There's an event group that I attend regularly. And the person who runs it starts off every session that we have by giving the rules and guidelines, even when it's all people who have been there a bunch of times before. Obviously, when there's new people, it makes sense that he runs through the setup, but sometimes there'll be 18 of us and we're all super regulars. We've been going for years, so there's not really a reason to do it. But there's this interesting side benefit, which is that because he stated them at the beginning, then when someone does something that is ignoring one of the guidelines or has done something that's inappropriate in the context of this particular event, he or anyone can refer back to the guidelines and say, “Remember how we talked about in the beginning that it's really important to listen three times before you begin to sing along?” This is a singing thing that I do. Because it's referring back to a neutral, it doesn't feel like an attack on a person. Instead, you're just bringing them into the room in a way that means that when you reference them, it feels less personal. It feels more like a systemic structure thing. I've noticed the way that it allows us to, if he had not brought them up in the beginning, it would feel very pointed. And instead it doesn't feel like that at all. And I think that's really lovely. One of the other parts of that question was how do you decide on the values and on tools? I think of Margot Bloomstein's message architecture card sort … you can use that structure. You can honestly use her card sort that she details in her book. But you could also take that and adapt it a little bit. But the kinds of things that we do to figure out voice and tone and the kinds of things that we do to to set priorities for … we say all these 19 things are important, but which four are actually important and what order are they prioritized in? You have these skills already. This is just a choice to apply them to a bit of a meta conversation.

Larry Swanson: As we build relationships, how do we reinforce trust through, say, co-building what success looks like?

Eileen Webb: I mean, that's it. That's what you do. You co-build what success looks like. You answered your own question. Good job. Yeah, don't be so isolated. That's the thing I think for most of us in a lot of contexts is don't try to do it all by yourself. It's better when more people are involved. It's better to share the planning. It's better to share the execution. Everything is better when more people feel like they have ownership of a process. More people feel like they got to participate in a full way in whatever that means for their context. Maybe they didn't want to be in every single meeting, but they got called in for the right two. It's almost like you want to design, from the beginning, that the intention is that the team wins, not that you win.

Patrick Stafford: Yes. And, I think something that can come as well, a little bit later and you have to be very careful about this, is embedding the principles or the success state in the individual performance metrics for people. Because sometimes when you all agree about success, but there's no real stakes to it, things can become less important and they're seen as secondary priorities. If you agree on a content strategy and you agree what everyone's achievements and contributions should be, that needs to be codified. And it can't come too early because if you're, if it's coming too early, then you have 1 or 2 people who are just being set up for failure. It has to be across an organization. It can't just be run on vibes. There needs to be some accountability to what you're trying to build as well.

About the speakers

Larry Swanson has 25 years of experience as a content modeler, digital architect, and community builder. He is currently the Community Growth Manager at metaphacts, a leading knowledge-democratization and AI platform. He hosts the Content Strategy Insights and Knowledge Graph Insights podcasts and has co-organized several professional communities and event series.‍

Patrick Stafford is the CEO of UX Content Collective and host of the Writers of Silicon Valley podcast. He helps content designers scale their impact, build influence, and navigate the evolving role of content in tech.

‍Eileen Webb helps content and product teams build trust, improve communication, and make sense of complex systems. She’s an experienced facilitator and information architect with a background in taxonomy, coding, and human-centered process design. Eileen leads workshops and conversations that help teams sort out their structure, language, and shared goals, with an emphasis on practical solutions and long-term sustainability.