Tent Talks Featuring Jonathan McFadden – It’s Okay to Be Inflexible in Content Design

[00:00:36] Chicago Camps: Jonathan, tell us about your background and what you’re doing today.

[00:00:40] Jonathan McFadden: Thanks for asking, Russ. I’m Jonathan McFadden. For those who don’t know me, I’m a senior content designer at Shopify where I work on the Shop app. But before I give more detail about that, I’ll actually answer your question in the order that you structured it and talk a little bit about my background.

[00:00:54] After graduating college, I went into the job market as a newspaper reporter. So I have a journalism background. And I did that for about five years initially covering crime and public safety and breaking news in the court system in a suburb of Charlotte, North Carolina. The city I worked in was actually in South Carolina, so it was a border city.

[00:01:13] Meaning it saw a lot of action. I was always very, very busy. Believe it or not, there was a lot of crime crossing over, a lot of crime happening between Rock Hills, South Carolina and Charlotte, North Carolina. Like I said, very busy. Got really immersed in the world of cops and robbers and police and the criminal justice system and how messed up that is and how complex and systemically awful it can be. And got to learn a lot about it and loved it. I really enjoyed doing that work, but wanted to grow my career and so I ended up getting a job at the Charlotte Observer, the largest newspaper in the Carolinas, where I covered small business and entrepreneurship, and that’s where I started to get immersed into this world of UX and understand that what UX was as a reporter, like as a crime reporter there I wasn’t focused on user experience. My days were spent on murder in mayhem and fires and meth lab busts. That’s what I did every day. And then here I go covering startup culture in Charlotte as it was burgeoning. And so got to learn a lot about app development and talk to people who were really brilliant.

[00:02:19] Not to say that people in the criminal justice system are not brilliant. It’s a different type of brilliance and got to learn a lot about tech. And so I did that for a bit before I covered county government for Mecklenburg County, North Carolina. And then in 2016, I left the news business entirely because it wasn’t filling me in the same way as when I first started.

[00:02:39] Legacy media has gone through a lot and I felt that. I felt it a lot, and so I wanted to find another way to use my reporting and writing chops and research chops bigger.

[00:02:50] Surely there’s something else I can do, and I found that as a marketing copywriter for a little bit. I did that work at a mortgage company of all places. But it was an interesting mortgage company because it had a really interesting mission statement, which said that they existed to love and value people, which isn’t what you would typically find from a mortgage lender. And also, I was working at Charlotte, which I mean is a huge bank town.

[00:03:17] So when the mortgage crisis was rippling across the US it was reverberating from Charlotte. A lot of people focused on New York and maybe San Francisco. Charlotte had like its home base for Bank of America, a huge Wells Fargo operation. There was Wacovia before Wells, and yeah, it’s a big bank town.

[00:03:35] Anyway, so I did copywriting for a little bit, but then I saw a job listing two years later for a content strategist. I had no idea what a content strategist was, but I was interested in it. Read the job description, figured it was something I could do that would gimme an opportunity to really be part of more ideation and not so much feeling like I was part of a service line, so to speak. And so I ended up joining LendingTree, which is FinTech. That’s an online lending marketplace. And so I joined as a content strategist. And what I ended up doing there was essentially what I liked to call hybrid of sorts in terms of job responsibility.

[00:04:11] So I was embedded in the creative team, which was part of the marketing department, but also partnered with ux. So it was all sorts of things. I was doing product work, but also marketing work. So I was at every end of the funnel it seemed, and that’s when I began to realize that the stuff I was doing in the product, in our logged in experience in our app, there was an entire discipline focused on this.

[00:04:38] The words I was writing called a thing called microcopy and there were people who were content strategists and content designers and UX writers who were really proficient in understanding the nuances and the particularities of microcopy and how that works in the brand, in the grander, more grand user experience and ui.

[00:04:58] And I began to learn all those things and go to conferences and meet people in that. And really fell in love with the product work, and so I kept doing that. Finally, I got a job as a senior content designer at a company called Red Ventures. I worked on a product team there for a little bit. That’s when I had a brush with management.

[00:05:14] When I say brush with management, I was a manager, so I took a forte of sorts in management for a little bit and really enjoyed it. But I did not stay at the company very long and eventually made the move Shopify. And so now I work on the Shop app.

[00:05:28] I’m part of the core shopping experience, and so I work with my design partners, research partners, engineering partners, to really build the, I guess you could say, the shopping ecosystem for the app. Traditionally, historically, it is an order tracking app. It has pivoted to an order tracking and shopping app, and I am part of a group of people who’s responsible for creating those experiences.

[00:05:50] So I work on the home feed, for instance, I work on what we call our discovery surfaces, things like search and things like landing experiences in the app. I work on the product display pages and the bag. We call it the bag. It’s really our cart. That’s where I work. That’s what I do. There’s a lot more to it, but I feel like I’ve taken up a lot of time answering that question already.

[00:06:13] Chicago Camps: Your background in journalism is pretty intriguing. Would you share how that has helped your career in content design?

[00:06:20] Jonathan McFadden: I feel like my journalism experience is a lot more commensurate with my UX work today. Journalism was with copywriting, and a lot of people may not naturally think that, right. A lot of people make the leap from reporting to copywriting. That’s a really like natural kind of next thing that you’re looking to get out of the media space.

[00:06:40] I feel like I am a bit of a journalist now in a different way. Sure. I’m positioned very differently and the information that I deal in is very different and very focused, I would say. But yeah, when it comes to research, asking questions, interviewing. I interview stakeholders all the time. We don’t call it interviews, we call it a kickoff meeting, but it’s basically the same thing.

[00:07:03] I’m utilizing the same set of skills when it comes to ensuring that what I’m creating, what I’m designing is brief and succinct and concise. Being a journalist taught me, it taught me how to write short, and I still write short today. Long form doesn’t exist in my world for the most part.

[00:07:18] So it’s really taught me how to think about information like information architecture, like when you’re formatting a story for the newspaper, like you have to think most important thing at the top. There’s hierarchy that you have to consider. So when it comes to things like content modeling or using content hierarchies, or talking about IA work, I’m like, well, yeah, we didn’t call it this when I was a reporter, but I, yeah, I do this all the time.

[00:07:42] So, yeah, I get it. Just make it a little more abstract. Throw some visuals on it and then you go, okay, it’s IA. I don’t mean to diminish that work at all, but the concepts, the practice, the skillset is very much the same.

[00:07:56] Chicago Camps: Invariably, someone will focus on the title more than the intent and context. Share what you mean and what you intend when you say it’s okay to be inflexible in content design.

[00:08:08] Jonathan McFadden: Yeah. So right off the bat I wanna tell people I am not giving you permission to be a jerk. I’m not gonna give you permission to go in knocking down doors and making really strong, I won’t say outrageous, but strong demands and kind of like throwing your weight around and hitting people with an adversarial attitude, like that’s not what I mean at all.

[00:08:31] What I mean is taking a principled stand, because that’s what UX is, right? We are advocating for the people who are using the (apps), and so if we find ourselves perhaps working on a feature or working on a new product launch or whatever the case may be, and there are things about that experience, things in the flow, things that we’ve noticed, things in the content, things in the design that we realize just are harmful, innately.

[00:09:01] Things that will perpetuate harm, things that will discriminate against people, things that feel ableist or racist or sexist, or et cetera. We have a responsibility and a duty as content designers, as UX writers, as UXers to say something. You see something, you say something, and it works that way at work as well.

[00:09:23] And I know that can be really challenging and that can be a really tough thing to do. To actually take that kind of stance because work is not a safe space for so many people. Historically, it has not been a place where you can voice your opinion or you can maybe be the lone voice in the wilderness crying out against something that is inherently harmful or something that’s deceptive or something that you just know is a bad UX.

[00:09:49] Content people. What I want to tell you, what I want to get across is that you do have that power. You do have that voice, and you should feel like you have that level of ownership. You have the vested stake in the user experience, just like the product designer, just like the product manager, just like the development manager or whomever else you’re working with.

[00:10:11] You advocate for the user. So if there’s something that raises some kind of accessibility issue and you realize. Don’t just shrug it off. Don’t just be like, uh, okay, it’s fine. This is what they want, so we’ll do it that way. No, tell people, educate people on why this is something we should not do. It doesn’t mean you’ll win, and it doesn’t mean they’ll listen, but at the very least, you might go to bed easier or sleep better at night knowing that at very least I said something.

[00:10:41] And so that’s what I mean by inflexibility when it comes to certain things, harm. racism Accessibility issues, things like that. Don’t bend, be inflexible.

[00:10:51] Chicago Camps: The way you speak to inflexibility is important. Talk about how being inflexible in content design can actually improve collaboration.

[00:11:01] Jonathan McFadden: Great question. It invites a conversation.

[00:11:04] If you are working on a product team in your, whether it’s a pod or whatever jargon you like your company likes to use to describe your team, but you may find yourself in a situation where you are the person who’s raising a certain issue, you’ve detected something, you’ve identified something, and so you decide that you need to bring this topic up because it’s just not sitting well with you and you know that this isn’t the right thing to do.

[00:11:31] Being inflexible and refusing to budge in the face maybe of a product manager’s demands, or maybe even your own manager’s insistence that, Hey, we need to ship this thing and you can’t be the blocker. This creates an opportunity for you to have the conversation with those stakeholders and explain, listen, I’m not trying to be difficult.

[00:11:54] I don’t wanna block us. I want us to ship, but I want us to ship good stuff. I want us to ship a product that’s humane. I want us to ship a product that people can. And won’t walk away feeling like they’ve been diminished, like they’ve been heckled, like they’ve been manipulated. We should not want to ship those kinds of products.

[00:12:19] Now granted, not every company is the same. Some companies may be okay shipping shoddy products and that’s on them. By and large the people who do this kind of work, whether we’re content designers, product designers, UX managers, whomever, we’re not in this to do shoddy things, and we’re not in this because we don’t care about people.

[00:12:42] Most of us, and this is a universal statement, but I feel comfortable saying that a good number of us really care about what people experience. That’s the whole. We want to make things better for the everyday person because we understand that life is hard and things out there are difficult. And tech can either augment and make things better, or a tech can take away and make you feel like dirt.

[00:13:14] Case in point, point to this example all the time, but facial recognition algorithms that will misidentify people with dark skin hues as monkeys. Nothing about that feels good or may misidentify you or conflate you with someone who’s a criminal, and so you get detained at the airport. This is an example of technology causing harm.

[00:13:39] I don’t want that. I don’t wanna do that. My conscious can’t take that. Most people would agree. We don’t wanna work on technology that creates more harm in the world. Because there’s so much harm already being created all the time we got in this because we wanna mitigate some of that.

[00:13:57] We wanna alleviate some of the harm. And so that’s why I think it’s so important that when we are in the context of our individual jobs, I get that sometimes it’s hard to extract yourself from the minutiae of it all to think about the bigger picture. But you are shaping this tech experience for a person and you hopefully are in it to make their lives a little easier so they can get stuff done.

[00:14:23] And so that’s why you have responsibility I feel like, to say something if you notice something. So have the conversation cuz at the very least you saying that thing, it’s gonna plant a seed or plant an idea in someone’s head.

[00:14:36] They may not agree with you. And again, you may get overruled. Trust me, I’ve been there. It doesn’t feel good, but it’s part of the job. But at the very least, that person you talk to, each one teach one. They get it. They have it in their heads. They can choose to ignore it’s on them. You can’t control how they respond to the information you drop on them, but you can control whether you drop the information.

[00:14:58] Chicago Camps: What do you do if and when inflexibility and content design is met with inflexibility in the organization, and worse, potentially from a position of authority?

[00:15:12] Jonathan McFadden: It’s hard. It absolutely is hard. And here’s one of the reasons I’m so passionate about this topic. I wanna be careful not to make these sweet being universal statements.

[00:15:22] I cannot speak for all content designers on earth. However, I do feel like sometimes given how content designers, UX writers, content people in general are positioned in most organizations. We’re sometimes put in this place where we can take on this bit of an inferiority complex that because our skillset perhaps isn’t as valued as a product designers or as specialized or technical as an engineers, we sometimes get saddled with this feeling like, I don’t have a voice here. I’m not as smart as these people. My work doesn’t really matter that much.

[00:15:59] And so what ends up happening is that we find ourselves maybe sometimes shrinking back because the organization almost validates that, right? I don’t hear from a lot of people who were like, I really felt like I wasn’t fully aligned in the right way of my organization.

[00:16:17] And someone came along and said, no, we absolutely need you. You are an invaluable member of the team. That does happen, but it doesn’t happen a lot. A lot of times content designers, UX writers and the like, are still trying to advocate for themselves and still trying to explain to people and educate people on what we do.

[00:16:35] That does not put you in a very powerful position within the confines of a tech company, especially where people don’t know what you do. They don’t know what value you bring, and so they may treat you as such. And if you are this person who all of a sudden they expect to just do the words in the boxes and you come with this, what you feel like is this really stirring and powerful point of view about, hey, we should not use all caps in our headers, or “white glove” really should never appear in our EY. They may look at you like “and you are…?” You may not get the buy-in that you would hope for, and that could be really tough.

[00:17:16] And then it’s even tougher when you feel like… okay, maybe to overcorrect, I need to just shove my way in there. I need to insert myself in the conversation. I need to forcefully take a seat at the table and I need to just get in there and be as aggressive as I need to be. That also has a very negative effect, right? Because people are suddenly like, oh, so now you’re a jerk. Now you’re combative. Now you’re, you’re not a good team player, and they’ll use those things against you.

[00:17:43] It is a very delicate balance and it’s a fine line we walk a lot of the time. I will say that one of the things we have to be able to do, and I think this goes for anybody at work, is to discern what is a battle worth fighting and what is a battle worth shrugging?

[00:18:04] And I know that can be very difficult. That’s a lot of mental calisthenics. That’s a lot of interrogating yourself internally, doing a lot of that internal mental chatter, which is exhausting. However, it also is survival in the workplace for a lot of us, especially if you are junior in your career. If you are a woman, if you identify as a woman, if you are a member of an underrepresented community. If you’re disabled, neurodivergent… these are the realities that we’re faced with. We oftentimes have to pick our battles, at work today, I have to pick my battles, and so when you are met with resistance and it doesn’t seem like it’s going anywhere, there may be a time where you have to do a self-assessment and be like, okay, fine. This is the decision. It is out of my hands. I did what I could do and I have to be okay with whatever the outcome is because at the end of the day, there’s so much outside of our control.

[00:19:09] Even like you could be the VP of product at a company, and yeah, you could be making all of these important decisions. You could be driving immense impact for the company. You still have a boss who can override you at any moment and tell you, you know what? I don’t like this direction. Do something else. And that will change the course of your entire week or month, depending on what the change is, may change the course of your career.

[00:19:33] I think there is a certain level of embracing how much is out of our control that helps us stay grounded and maneuver the complexity of it all. Because you can easily internalize a lot of this and feel like their refusal to essentially do what I say is a reflection on me. Like I’m the problem. I didn’t, I didn’t articulate this correctly. I didn’t tell a good enough story. I didn’t present myself at all that, no, like I’m sure you did your absolute best. You showed up how you needed to show up, cuz you’re a professional and you get it. A lot of times it has nothing to do with you.

[00:20:12] So many other factors at play. When I initially wrote that whole rant about inflexibility, before I wrote it, I debated whether I wanted to share it, whether it would make sense, whether it would resonate with people. Cuz I was thinking about the economic reality we’re in right now. I don’t know, a single person, another content designer working at a company that hasn’t been touched.

[00:20:32] So telling people, hey, be inflexible, like is this gonna maybe come off a little flat? Is this a time to be spreading this message. There are economic realities at play. It is a very privileged thing to say just don’t work some place. You have bills to pay. You have people to feed. You may have children, you may have a partner, you may be taking care of aging parents.

[00:20:54] There’s so many different things, like I think the reality is, I say this a lot, maybe this isn’t for everybody, but if I didn’t have to work for a living, there’s a maybe 95% likelihood I wouldn’t if money wasn’t a thing. Sometimes, yeah, there are things you may have to choke down that you otherwise, in a different situation or a position you wouldn’t have to or wouldn’t want to.

[00:21:20] And I get it, like there are certain things you should never tolerate – abuse, like you should never tolerate that.

[00:21:25] Chicago Camps: How do you recommend folks approach inflexibility without getting labeled as difficult?

[00:21:33] Jonathan McFadden: I think it’s all in your approaching your delivery. Again, there are some people who are given allowances at work to be very adversarial, to be passionate as they may be called, to be loud and vocal. And then there are many others who are not given that same lattitude. If you are a part of the group that’s not given that same latitude. And I would characterize those people as, like I said before, people who are part of underrepresented communities, people who identify as women, people who were disabled, neurodivergent, I think it is, as much as I hate it, it is, important that we take a deft, delicate touch with these kinds of conversations. That doesn’t mean you censor yourself, but it does mean it’s good practice to learn how to package and to learn how to develop an argument in a way that’s compelling to learn the language your stakeholders are speaking to learn what resonates with people in those positions of power.

[00:22:38] I had to speak their language. I remember when I worked at Lending Tree and we were starting that company’s first diversity and inclusion group. We had two versions of a presentation to pitch this idea. One was for majority employee base where we could be a lot more celebratory and talk about the things that we really wanted to change and some of our aims and our goals, and we had some of that in the presentation for executives.

[00:23:05] We also included a lot more numbers because that is what they respond to. And so we knew that if we wanted to get anywhere, if we wanted to even get in the room and be taken seriously, we couldn’t just come with “this is the right thing to do.” That does not sway the business.

[00:23:24] The business does not care about the right thing to do.

[00:23:29] People within the business do, yes. But the business as an entity is designed and set up to make money. So how is this going to help us make money? That is always the question, how will this boost revenue? How will this increase profit? How will this help conversion? Like those are the things people in the upper echelons of your company’s leadership are thinking of.

[00:23:56] They may be advocates for inclusivity and accessibility and diversity and representation. That is wonderful. But when it comes to their impact, when it comes to how they are assessed by their bosses, when it comes to the people they answer to, I guarantee you. Those are not the things that their overlords are looking at when gauging their impact to the company.

[00:24:20] The same person who might be the executive sponsor for your ERG is the same person who has to give a report quantifying what they’ve done for the company. Speak to them in that language, because that will help them make a better case for you. So when you’re approaching flexible type of conversations, I think again: package. Package that argument in a way that will resonate with the audience you’re giving the argument to.

[00:24:47] I’m not saying that you have to pack some kind of like presentation with a bunch of statistics. It could be a Slack message, it could be a quick call over a Zoom or Google meet.

[00:24:58] Think about it before you go for it.

[00:25:00] Like really think about it and develop strong conviction. People, especially in one-on-one situations are probably more likely to hear you out if they understand just how much: one research you’ve done; two, how much expertise you’re bringing to the table; and three, how strong you feel about it.

[00:25:25] One of Shopify’s values that value systems that they’ve created for. Is to develop these strong opinions, right? Strong opinions held loosely are considered very important, are sacred at the company. And so knowing that, I understand that when I’m having these kind of conversations, I’m not trying to equivocate. I’m not trying to be like, maybe we should consider, or perhaps it would be nice if we could, that’s okay in certain context. But if I’m talking to our product leader, I’m saying we should do this. Here is why. Here’s the outcome and package it that way.

[00:26:05] Chicago Camps: And now we have a question from our live studio audience, Larry asks: if you agree that good writing is good writing, what writing books, articles, et cetera, do you feel do a great job of explaining how to be a better writer.

[00:26:22] Jonathan McFadden: When it comes to a book recommendation, I will give one and it’s a book call, how to Write Short by Roy Peter Clark, and writing short is an art, and it is a skill that needs constant development and constant practice because a lot of people, I think people who are perhaps not writers, have this misconception that being a good writer.

[00:26:53] Means that I can regale you with my expansive vocabulary and with how smart I am, it needs to be long and just full and meaty. This is my magnum opus. It needs to be a Tale of Two Cities. Yes, that’s good writing.

[00:27:09] Okay, good writing is writing that people will read. That’s how I define it. And so in this day and age, it certainly is not a Tale of Two Cities.

[00:27:19] That’s great. You should still read that. That’s literature. That’s important. It’s history. But it really is succinct, it’s concise and it’s packed with meaning. It’s vivid, it’s descriptive, and it’s easy to parse. And I know there are some purists out there who are probably like, how dare he? But when you’re talking again about writing, I think good writing is writing that’s usable is writing that people will read, it’s writing that gives people something, gives them an ROI on their in.

[00:27:50] And writing short is a way to get there. Keep it brief, keep it simple, keep it punchy. To potentially contradict everything I just said. I did finish a manuscript for a novel in December. It is not short. It is currently undergoing editing, so it will probably get shorter, but just because the page count is long doesn’t mean the way I wrote it is long.

[00:28:12] If that makes sense. You can go through a voluminous piece or a meaty piece or book, for instance, a novel that is a page turner. You just go because the writer, the author, has been very intentional about their phraseology, about the punchiness of what they’re writing, about, how they organize and construct paragraphs.

[00:28:36] And so the manuscript I wrote?

[00:28:39] Punchy.

[00:28:41] I love a good one word sentence. I’ll find an opportunity to do that and I found opportunities. Now the editor may be like, this is not how you write a book, but that’s okay. This is how Jonathan writes a book because Jonathan knows what people will read cuz the type of writing I do in my career is always about what people need to be able to digest quickly.

[00:29:02] When it comes to other resources. A news article. Journalists, yes, I’m biased, but journalists are trained and are accustomed to writing again, in a way that’s packed with meaning, informative. It’s full of substance, but it’s also brief. It’s also concise. It’s quick, easy to parse. If you wanna learn the mechanics of being a really good writer, study how journalists write, how they write their stories.

[00:29:31] Learn the nuanced differences between a hard news story and what we used to call a soft news story or a feature story. There are opportunities where the writing is more vivid in a soft news or feature story, and so you get this like it’s magazine style and so you, you’re just immersed in the world that the writer and the author is crafting with words.

[00:29:52] Then there are the stories where da, da, da da, this happened, this happened, this happened the end, and both are really great types of [00:30:00] writing. That I think have made me a stronger writer. When I was at the Charlotte Observer, I came in understanding how to be a reporter. I thought I was a really good writer, but the Charlotte Observer was renowned for its editing chops.

[00:30:16] That’s when I learned how to be a really good writer. There’s a saying, kill your darlings. Kill ’em. You gotta kill ’em. Kill the flow, and the news will teach you. Teach you a lot of other things that are not so great. But in terms of like the mechanics of what good writing looks like and what comprises good writing, I honestly think the news and Agatha Christie novels. Highly recommend.

[00:30:42] I’m a huge Agatha Christie fan, and I think she was an amazing writer as well. Definitely highly recommend. So yeah, I don’t have like the only one of those that’s like academic or prescriptive in nature would be How to Write Short. But everything else, I would say draw inspiration from the things you enjoy reading.