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The day has come — your boss has finally asked for a big digital transformation. What now? In this third installment of Postlight’s Doing More With Less panel series, Postlight’s Associate Director of Digital Strategy, Chappell Ellison, chats with three experts in digital transformation. Leyla Ballantyne, Julia Beizer, and Stephen Tateishi share their digital transformation nightmare stories and tips on how to get back on track when managing unruly projects.  


Julia Beizer: It sucked when I got a new job. 

Chappell Ellison: That’s one way to deal with digital transformation.


Chappell: And we’re back with another episode recorded live at the Postlight offices in New York City. I’m Chapell Ellison, a digital strategist here at Postlight, and you’re about to hear the third installment on our series about doing more with less. You’re about to hear yours truly talk with veteran strategists on all things digital transformation. What it means and how to achieve it when resources are limited. If you’d like to attend a Postlight event in person or remotely, check out for more information. Now, let’s get into it.


Chappell: We’ll do the thing where we do the intros, I promise. But I want to start with a cold open. So it’s gonna be an easy question to start with. Your boss or your client comes to you and they say “We need digital transformation.” In one or two words, what’s your internal gut reaction? No thinking. Go. 

Julia: Pain and suffering.

Chappell: Julia. That’s the job.

Leyla Ballantyne: I like that. 

Chappell: Stephen?

Stephen Tateishi: You’re not ready for personalization. Yeah. 

Chappell: Okay, those are even better than expected. This is why we’re gathered here to talk about the scariest thing, which is digital transformation. My name is Chapell Ellison. I’m a digital strategist here at Postlight. We are a digital agency in New York City, as you might know. You can find out more about us in, and that is the only ad we have today, I promise. So we’ve assembled some friends here of Postlight. They’re all strategists in your own right and they’re gonna help us tackle this really strange, bizarre topic to some, but is very normal to all of us. So I wanna start with intros. Would each of you just say your name and a little bit about. And what you’re up to. Let’s start with Leyla.

Leyla: Hi everyone. I’m Leyla. I am a vice president of strategy at Huge, another digital agency. I live in Houston, Texas now. I used to live in New York, so very, very happy to be back and be with all of you in person. And I’m gonna hand it off to Julia. 

Julia: Hey, Julia. I am Chief Digital Officer at Bloomberg Media. I started my career as the journalist, but kind of slowly edged my way over into product management and digital strategy. I just have to say, you guys are a really good looking crowd. 

Stephen: My name’s Stephen. I have been a freelance content strategist for many years, a decade or so. Started early on. I—I was a copywriter. I mean, was a lot of things. I worked in, non-profits. I burnt out on. I became a copywriter accidentally. I smoked cigarettes outside. I met a bunch of Eastern European developers who were like, “Why are you a copywriter? Everything you talk about is content strategy.” I was like, “Okay, I guess that’s maybe something I should do.” I had some luck with that profession for the last three, four years I was the director and senior director of content strategy at Code and Theory. I left there in June. I meant to be unemployed, but I accidentally picked up a freelance gig, but in theory, I’m taking a little bit of a break from the treadmill.

Chappell: It never Lets go. So I wanna start by honing in on this cuz we kind of skipped over what we should probably do first, which is to define what is this thing? When people say this phrase, digital transformation, what do they mean? Do any of you wanna take a swing at what a client or a boss might mean when they say this?

Leyla: Sure. I’m happy to start. You know, I think it starts with where the organization wants to go from a business perspective. That’s my background. I started in market research, probably should have credentialed myself a little bit so you guys think I’m qualified to talk. But—and then I worked at—at Macy’s for several years including corporate strategies. So, Transformation to me always starts with “where is the business trying to go? What customers are they trying to acquire? What’s their next move in order to differentiate themselves and and get ahead of the market?” And then I think the technology that enables that and all the business processes follow. So I think digital transformation starts with making a clear decision about where you wanna go. That’s a really, really hard thing to do. And then I think the rest comes more natural. So deciding what experiences are gonna enable these business goals and then how does the back end then come to life in order to make the front end a reality?

Chappell: That was very thorough. [laughs] Anyone else wanna add to this? Have you felt, have you experienced anything different in your own definition of digital strategy? 

Stephen: I don’t really think clients know what they mean. Frequently when they say they want digital transformation. They want features. They want flashy experiences. They want something that could be a great headline for an email one year from now to their bosses. But they’re not always really cognizant of really all of the work that you just talked about, which is strategic, which is, you know, driven by business goals, which is driven by data which understands that your product is essentially a system. And that systemic change means kind of thinking of things end to end, and identifying what’s, what the priorities are and the work that’s really needed to get there. And sometimes unpacking that is a difficult conversation to have with clients who are kind of looking more for the effect and not the process, and I think digital transformation is changes in process that then achieve changes in experiences.

Julia: Let me jump in. 

Chappell: Yeah. 

Julia: Cause I think I’m a, I’m the weird one on this panel actually. 

Chappell: You—you are. I mean, I think this is important to say: if—if this terminology is not common to our listeners here, is, you know, you might be what some might say is in house in our world. 

Julia: Yeah. 

Chappell: Someone who is—and whereas we are all in agencies. You’re at an agency. Both Leyla and Steven have worked in agencies. So yes, I would love the in-house perspective. 

Julia: Yeah. I’m an operator. And I’m a intrapreneur. That’s a—they’ve branded us that, it’s great. And my whole career has been in the news. Which like the whole thing has been digital transformation since I got there in 2004 or five, or whenever I started working in the news. Right? And so my perspective on that has been like, you know, that the work of my entire career, right, quote unquote, my life’s work will be digital transformation. Because as businesses are going through these massive changes and like, I don’t think I would make a very good out of house strategist. Like I don’t think I would—I just like doing the stuff. I don’t wanna do the PowerPoints and leave, like I like making things. And so I think that, not to say that’s what I think you are. You know, I—I really like making the things, I like doing that it is hard, brutal, frustrating, emotional labor. Work is what it is actually. But it is so glorious at the end when you move in—you move a huge ship, a couple of degrees, and then a couple degrees more, and a couple degrees more, and then you look back over a course of years and, and you say, “Wow. I remember when we were there.” And so digital transformation to me is the work of our generation of workers. Every company is digitizing in their own way. They all understand it differently. And in the last couple of years I’ve been really reflecting on how that work is more cultural than it is technical. And how it is, you know, thinking about like, Where your customers want versus what you wanna say. And like just it’s mindset shifts left and right and that, that’s my perspective on the term. 

Chappell: All right. Yeah. To follow up on that, these, I think you’re really hitting on something that we forget as jaded agency employees, which is that digital transformation actually can come with a lot of positive intent. You know, we sometimes see the grind side of it that’s not so happy and you know, we deal with some clients maybe unhappy with us. But can you talk more about what you see as that positive intent behind these words? Like that isn’t jargon, that’s the real thing? 

Julia: Yeah, I mean like I’ve been reflecting on this is. I—I don’t know, I’m 41, like when I turned 40 during the pandemic, which is such a drag, but like whatever, and facing my own mortality and like when I was really like young in my career, in some ways I was better cuz I just didn’t even know I was like a child walking into a hornet’s nest. Like. I didn’t know what I was asking for. I was just sort of like, “you guys are dumb and the internet is awesome. Like, I can’t believe you don’t get this,” You know, . Now that I’ve gotten slightly more mature, I’m like, “Oh man, these people are scared.” Or “they don’t see the possibility of this.” Right? Or “they sort of know they need something but would prefer not to spend any money on it,” you know? And so I think that there is certainly, I think, an understanding at any rational company now that like you need to digitize, you need to employ digital people, you need to find digital talent, you need to embrace them. But I think there’s kind of a lack of understanding of what that looks like in practice. And so like a lot of what my work is—is being like, “hey, what are we scared about? What are we scared about in this meeting?” And, “oh, okay. It’s that, All right. All right, let’s work on that.” And that work is slow. Entrepreneurship is a drag. I saw these guys from Cornell Tech who like teach a class in this. One of ’em used to work at Google or whatever and they were like, they wrote a book on this. And they were like, “Cuz nobody ever talks about—they talk about founders in the garages. Nobody ever talks about when Susie nails the big meeting.” And I was—I was like, “Oh, I feel so seen in the—” you know what I mean? Like, it—it’s a grind. But again, this will be the work of our careers. Whether you’re an agency or not, you will work on this problem. And so like, get used to it. There’s no like magical utopia, which I think, I thought when I was younger, wherever I was just gonna like get it like, nope. Like maybe for my kids, but not now. 

Chappell: Well, to make it a little more concrete, cuz we’re—we’re talking, it’s funny how digital transformation, it brings up a lot of big feelings, but to make it more. Could y’all just from your careers, give examples of what a digital transformation might be? They can be very general.

Leyla: Buy online, pickup in store as like unsexy and ubiquitous as that sounds now was like a very hot topic in retail and you still got retailers that are still like, “We should do that. That seems like it makes sense, post pandemic.” I think payments has been huge. I mean that’s—that’s pretty incredible. The transformation, the payment space is, is astounding, like what you’re describing in terms of shifts in culture. How people interact. How we get things done. I think that’s been incredible. Well, we can use Starbucks as an example. Macy’s tried to do some of the same things to a lesser extent, but the fact that Starbucks has as much payments flowing through its systems as it does in their own kind of, you know, currency and the way they reward points and all of it is, is pretty incredible.

Chappell: Stephen, from like the content perspective, what are some really big changes people try to make in the content world to transform their business? 

Stephen: I mean, it doesn’t sound very sexy, but like a lot of the work that I have done over the years involves really sort of creating data structures, thinking of content as structured data. Separating the presentation layer from the content structures in your CMS and—and creating systems that are able to reuse content, deliver content based on rules and things like that. You know, for that, there’s a transformation aspect where your end user is also your content editors. You know, you have these poor people who used to labor doing manual curation of three ups and things like that. It could be a, a massive benefit to organizations when they change sort of the paradigm of how they think about content within systems. Not only to impact their end user, that is the customer but to really improve the lives and the efficiency of their own organization and improve the lives of the people who put so much effort into creating the content and making sure that the content is reaching its proper destination. 

Chappell: So like the problem is, as you just said, not sexy work. And sometimes leadership gets concerned with digital transformation that equals like a big bang, you know? And do y’all have some experience maybe from your past about how you’ve been able to kind of convince someone, either internally at your own organization or a client, I know this isn’t the hot stuff, but it gets you where you need to go.

Stephen: That’s what those shitty powerPoints we make are for. 

Chappell: [laughs] 

Stephen: You know, I—I think that one thing people have really gravitated and started to understand is that data is really important, and there’s a lot of power in data. A lot of the transformation work that isn’t particularly sexy, just if you talk about it technically. What it’s really doing is creating opportunities to see it a—a whole new data layer that you could start gaining information. About your product, about your—the interactions that users have with your product and start creating intelligence. And I think that’s something that people appreciate. They may not necessarily want to hear or they, you know, may they, their eyes may glaze over. If I really go in depth about a content model and, you know, and content strategy is sort of unique-ish, in that it’s really dependent on a lot of other practices in the work they do to gain value or to really sort of bring that value that we talk about. So I think combining it and rolling it into a broader story that really is one about how your system can see data, how we’re not creating taxonomies. Just to be kind of fancy intellectuals, we’re really seeding that events that are gonna have semantic value and meaning for you and is gonna let you grow and understand your product better.

Julia: I—I couldn’t agree more like it is the job of the digital transformationalist—digital transformer? 

Chappell: It is the job! You always be selling, man. It is the job to like actually connect those dots for people. So like we all have to sell at our work a hundred percent, you know. But I also like, I challenge the question a little bit because, you know, like peril to the CEO who doesn’t see that at this. Yeah. You know what I mean? Like that moment’s over.

Leyla: Yeah. I think it’s, and I think it’s a question of—of what direction to go and convincing them that—that this is the right investment or this is right because X, Y, Z, or thinking more about the future and laying the right foundations. I think sometimes, there’s still misunderstanding around technical foundations and why. I have a client now and they’re like one of the biggest, best tech companies on the planet and they’re, you know, be—they’re behind in some ways cuz they don’t know when the right time is. They’re like dragging their feet. They’re like, “Well, we’re really big and we’re really profitable and yeah, we need to change that stuff over there. But it’s scary. We’re gonna have to reorganize. We’re gonna have reinvent. We’re gonna have to scrap, you know, this tech debt and start some stuff over. How do we do that?” Like there’s still, I think, convincing to do in that regard and—and make putting a really firm stake in the ground, it think takes bravery and executives with conviction to really command the room and to—to get momentum for the organization. So I think that’s part of what moves the needle, moves people forward, gets them excited, they feel more confident and their abilities to execute against this vision. 

Chappell: It’s somehow both comforting and disheartening to know the biggest and best technology companies on the planet are struggling with this. Yeah, I mean, you kind of wonder sometimes how we get here to this point because it seems to happen to all companies that your technology is old. At some point. Let’s maybe take it to the dark side a little bit. We’ve been talking about like some positive sides of digital transformation. So because it has this word transformation in it, it requires like big swings, right? It requires a lot, as you say, bravery. And I was reading—doing research for this, so I sounded like I actually knew what I was talking about and I was reading like the common reasons that digital transformation work fails. And something that came up over and over again is misunderstanding or a just lack of understanding of the true business problem. I would love, like, it’d be so great for specific examples. I know we always can’t use names and of clients and things like that, but would any of y’all have a specific example where you had a client who knew they wanted big change, but they were just so off base on what the true question and problem was?

Leyla: Everybody wants “glo yo” now, but they don’t know the difference between young people and a generation. 

Chappell: Everyone wants what?

Leyla: ” Glo yo” equals “global youth.” It’s like the new…

Chappell: Oh my God!

Leyla: The new hot thing, right? It was like millennials and Gen Z. And then they’re like, “you know, Gen Z and glo yo are kind of the same,” and “no one really knows the difference and it’s just a term.” And so I think, I think sometimes people feel like there’s change a-coming and then they’re like, “Well, we don’t really know what it is, but we want this audience and so how do we do it? And TikTok is cool, like, let’s make it like TikTok.” And you’re like, “So what’s the problem?” Like “what? Okay, well, let’s definitely get that. We—yes, we should consider the audience, but why? What about them relates to our brand? What ab—you know, what do they like about us? How do we move forward in that direction? And then look at the gaps and what are we not doing, right?” So I think that there’s some failure and, and sort of rushing that can happen. Really thinking about what it is that your customers want, what future customers would need from you, and then the difference between what like 13 year olds do and a generational insight. You know, like what’s universal to just 13 year olds in general. Like, I don’t know, you’re gonna make all your money off of them? So I, I think that that’s something I see. I hope that was specific enough, but I think you know that there’s a, that’s a real failure to address and, and claim a problem that the organization can rally behind. 

Julia: My industry is on a 18 year roller coaster, and the fundamental journey is, “okay, you know, print dollars are turning into digital dimes are turning into mobile pennies. And it was like, are these audiences even valuable?” And then HuffPo—like Huffington Post showed up and they were like, “Hey, yeah! We don’t even have to invest in content.” Which they later did . They’re like, “We’ll just take your reporting, rewrite it, and then be really good at SEO.” And then, Oooh man Catfish in the pond that got everybody in the publishing space. Like, “Wait, we should do something about digital. Okay, we gotta win digital. We should win digital.” And then over the course of the last couple years, essentially we’ve moved from things that I think many of you are probably not in journalism, but like you’ve even heard about. But it was like, “oh, the search wave. We should all do search and everyone should write a story to say what time is the Super Bowl? And then people search for what time is the Super Bowl? And then you get an ad view.” Okay, Like it like actual business model. And then there was a social wave and it was like, “man, if we just like, like whatever, like he proposed and then you’ll never believe what happened next. Click. Oh my God.” Then you get an ad view. Then there was the pivot to video, which was like, “you know what users like? Users Facebook and Google told us that people like video. Video is really cool.” Massive misreading of the data incidentally by our friends at Facebook and Google. Cause they were like, “You know what, people stay on video for a lot longer.” and I’m like, “Yeah, it’s harder. Read an article? Two seconds. Watching a video? You gotta stay on it till it finishes.” Anyway, whatever. So we all pivoted a video because that’s for the advertisers were gonna show up. And in the meantime, the advertisers actually went to Facebook and Google, who bought a—who built a better product. They built, you know, targeted advertising at scale. So I think where my industry is today is, “Man, we were digitally transforming. We were building new teams and rebuilding processes and turning print people into, you know, Instagram editors and stuff like that, just to catch the next new wave.” And what we missed was “where do you make your money? who is your customer? Do you own them or do they own them?” And I think what you’re seeing in most parts of the premium publishing industry right now is essentially like, “let’s just get back to basics on like how do we make money in this world? Who—who are we for? How do we make money in that model? And then let’s invest there.” and that doesn’t mean we move away from social. And that doesn’t mean, though it may in some cases, and it doesn’t wait—mean we move away from advertising. And though it may in some cases. But just means some more sobering, hand on the rudder of like managing your own business. So in the way, in the pursuit of digital transformation, we were just like, “We’ll just do this. We’re being so digital and cool. We’ll embrace, you know, fail fast, embrace a change.” And it was like, wait a minute. What are we doing? How do we make money?” Lost the ball in the lights. And I think we’re back. 

Chappell: That actually does kind of loop into my next question, kind of going along the dark theme of digital transformation is like, why does it go off the rails? And a lot of this, as I was just saying, you can forget your business goal, but have you ever had experiences where, A big transformation project has gone off the rails. And what did it look like and how did you know those wheels were coming off? 

Leyla: Yeah. I helped launch a—a national loyalty program while I was at Macy’s. It was huge. It’s like with American Express and I think five or six big national partners. And there was tremendous amount of coordination at all levels and our CFO really didn’t like it. Like she was not behind the program. And they—we had a thread bear team. I was on it and there was not internal alignment around the need for the program, what it could do for our business, how it would work. It was a, kind of like, a great opportunity for amex and they—they seem to be behind it, but without consistent partnership—we lost our grocery partner, which I don’t know if you guys are loyalty is like its own animal, but grocery is really important to point programs. Sorry, I’m going deep here. But so you lose grocery, you lose frequency and, and consumers don’t really care anymore cause they’re not earning all the time. So that was also a major strategic loss out the gate and we never really picked up. So the program died. So like two big thing, internal alignment, not there not happening. From the CFO, no less, who has to pay for the program, and then, you know, I think from a like high level program perspective, missing really like the linchpin to success and scale and driving adoption and, and that it was just, It was really hard to recover past that point.

Chappell: I’ll kind of pitch this one over to Stephen. This is part of my memory of a digital transformation horror story and full disclosure, Leyla and I worked together at Huge for a while. And we worked on a, a large beauty retailer, I guess I’d say. So why this might relate to you, Stephen, is like, You signed the contract. Yay. We’re excited. We have a small-ish team and a very large company and we got in there and we thought, this will be fine. We’re gonna just rebuild all your systems. And we just, the more we opened it up, it was like CMS, CMS, CMS. Like all these different content management systems and it’s like, “oh, that one was built in 1998. We haven’t touched it, but we have to use it cuz it integrates with this point of sales structure thing we have..” And that like kind of going. In your experience, like how do you keep going? When you see this kind of thing, when you open up the hood and have you seen these situations where they want transformation but you’re facing a lot of old dusty content management?

Julia: The labyrinth? 

Chappell: Yeah, the labyrinth. 

Stephen: Sorry. We’re still in the dark side? Right?

Chappell: Oh yeah. We’re still there. 

Stephen: Cause this may not have a happy ending. Yeah. I mean this happens a lot. And you know, that’s why it was great for instance, at Code and Theory we had in developers and I was always paired with a technical lead. So when the hood was open, it wasn’t just a bunch of smart strategists and so forth inspecting it, but it was always people with real technical expertise who knew what should be there and, and could analyze these oftentime homegrowns legacy systems. But the truth is, when you start to unpack things, oftentimes that’s where people can start to lose their nerves because they recognize that actually”, This isn’t as simple as we thought. There’s a lot of dependencies upstream and downstream. We have data being stored in a whole bunch of different places that can’t talk to each other.” We can come over with a strategy to jerry-rig and hack the system, or we could tell you what you really need to do. And so there—there, it’s usually above my head a little bit in terms of what our business strategy is for this relationship with this client. But you know, like me and the tech guy are like, “Jesus Christ, just tell ’em what the deal is.” Like, it’s worse, it’s terrible. And sometimes we try to massage things. Sometimes we’d, we’d be quite blunt. But, you know, we had a global news agency where, you know, we had great ideas. It was a great project. I kind of ran a ground because end of day we realized there were just legacy dependencies. That they were completely unable to move—move off. You know, in another instance, a less sexy, I guess dental hygiene equipment player? Yeah. We got in there. They’re like, “Oh, you know, Yeah, we—we’d like to do all this stuff, but by the way, every country uses a different CMS.” and we’re like, “Oh, and are we gonna start with one? Perhaps for instance?” They’re like, “Well, we’d love to do everything.” And we’re like, “Yeah, no, that’s impossible.” so like, that was rather shocking, you know, this is a, you know, multi-billion dollar concern. And they felt it was appropriate to sort of af you know, after kickoff be like, “Yeah, And, and by the way, we’re talking about 35 CMSs. And they don’t talk to each other and they don’t have the same structures and same rules.”

Julia: I got a good one. Along those lines. When I was at HuffPost, it was during the time where we were—HuffPost was part of AOL, which was part of Verizon. Then Verizon bought Yahoo as some sort of wedding present for aol. It was like all very, it was all very messy. But was fun for me as I was one of the product people on the AOL side and essentially like Yahoo won the merger. You know how that happens at companies. And so like the Yahoo, they were all. The PMs versus the GMs, which is something else I’m passionate about and we can talk about later, but like, The PM’s won and I—I was PM on the other side, so that was good for me. And a lot of what we were doing was, of course, trying to cut costs. I often describe this time as essentially like Verizon went shopping and came home and laid a lot of stuff out of the bed and was like, “Oh, I need to return some things.” And so like there was a ton of consolidation. And layoffs and like the real awful part of digital transformation. Anyway, like one project that, from a technical perspective, I had to evaluate with my partner from Yahoo was and are like basically like doppelganger inverses of one another, right? They’re on different coasts, but they serve the same largely old user base that comes to check their mail and clicks on some articles and sees the ads. That’s the model and it was like, wow, wouldn’t we be more efficient and get all of those efficiencies in terms of developers if we put it all in one stack? And like one interpretation of looking at the data was essentially like, how long do we think these cash cows have? Because the actual transformation project was going to take so long, the actual consolidation of those stacks to be able to maintain both of those businesses was gonna say, be so long and there wasn’t—this was preserving revenue, right? This was like a cost cutting project. This wasn’t a grow the business. The business was were instructural decline. So it was like, why would we spend several years consolidating CMSs? Then to even able to allegedly fire people. You know, how long do we think the businesses have? Cause if we think the businesses have five to 10 years, we should do it. If we think the businesses have less than five, we shouldn’t. And that’s a wild way to think about this, cuz because it was a—obviously the right decision in a vacuum. These things should be powered by one CMS. That is the efficient way to do it. But is that effort worth the squeeze? Like is the juice worth the squeeze in the end? 

Chappell: Yeah, I mean, we—we have a current client who we’re helping consolidate maybe 4,000 pages into one CMS. And that alone, it’s like tear your hair out work sometimes. So to think about that many pages, that much volume, and that’s a—that’s a horrifying decision to make to me.

Julia: Yeah. And like by the way, guys like cliff hanger, but like, I don’t know how it ended, like I quit cuz that’s like a… 

Audience Member: [crowd laughs] 

Julia: Like—like total drag of a project, right? Like that was my life for six months was being like, “let me understand this. Why are there a thousand pieces of middleware? Like, who’s gonna win this fight?” You know? And everyone’s feelings are there. And it was like, It’s a lot. 

Chappell: I wanna turn back to the light side. I lo—I mean, I love the horror stories. I bet everyone here—I hope everyone here has like horror stories of digital transformation. I think it’s healthy in some ways? Cause I know I’ve worked with some of you. We’ve been there. I wanna turn back to more of the optimistic side. You know, and also like we’ve been talking about a lot of big companies and things like that. Part of this, this kind of panel discussion is about how to do this work when you don’t have a lot of resources, or maybe you’re a startup may, or like maybe you’re—you’re—or you’re like a three year in company that’s trying to redo a lot of your work. Julia, maybe I’ll start with you on this one. You know, Again, researching for this discussion. So I sounded smart. I read a good phrase. It’s really simple, but it said, it was just the reminder that value can be incremental. You know? And I guess if you were giving advice to, say someone who, a digital team leader who maybe doesn’t have the budget to hire an agency and they have to just bootstrap it—kind of—what advice—where would you tell them to start on their projects so that They feel like they’re getting something from this transformative idea? Maybe what approach can they take? 

Julia: I think teams get a real psychic validation out of shipping. I think where teams really struggle is like these long, long projects where like you don’t really see the value. And so like I think my advice would be like find a foothold and ship something cuz then you kind of like, you get some momentum internally. You have to be really good at bragging about it, which is not my strong suit, but like man, I got the marketing team now and like those guys can brag. So like find one of those. They’re really great, but like just ship something, I guess is my answer to that. 

Chappell: That’s a good one. How, how about Stephen, in terms of content, I have like a thousand ways that I could answer this, but like, what are examples of ways people can like get a radically great outcome without having to rebuild an entire CMS?

Stephen: I mean, one thing they could do is understand their users. Like it’s amazing how little research people invest in on their actual users. I can come up with all sorts of fancy ways to, you know, like deliver content, but towards what end? And are, you know, are these the right kind of data points? Are we, do we really know who we’re talking to? And I’ve heard “right content at the right place at the right time,” so often it makes me want to throw up. 

Audience Member: [crowd laughs.] 

Stephen: I’m like, But hey, you don’t even know. Yeah, you—those three factors depend on actually understanding your audience and what their needs are. I personally think a little user research, like an actual research effort to sort of lay the foundation for the strategies that you’re going to do that can be modest can have huge payoff if it’s really grounded in strong research, and that’s something that I just don’t see enough. And someplace that I think a little investment can really go a long way. 

Leyla: Yeah. So for said large global tech company, they have a one of many B2B properties and we do their, their marketing site optimization. And we were like urging that. We were like, “we should do a site intercept survey and, and qualify the leads.” you know, like we finally did it and we were like, they were like, ah, we didn’t think that’s who I was coming to our site. So, and it’s just like, you know, four questions. Not sexy, not sexy, logic on it, nothing crazy. And it illuminated such a key insight. So I’m with you. I think even for large companies, small or large, I think that understanding your users is, is really critical. And then things are so downstream from there and then you can find the right tests, like what is the right thing we need to get out that’s incremental to where we are today. I don’t even think success needs to be the big giant CMS consolidation or like new, new tech or new shiny object. It can be something small like tweaking the copy on your site to actually align with your audience. 

Chappell: Who’d thunk. 

Leyla: Yeah.

Chappell: Yeah. We talked about this on an episode of the Postlight podcast. We were talking about the—a content management system. We had a—a client who—they think their CMS is terrible, and we went in and we were like, No, it’s just set up bad. And actually if you just reconfigured it, the low time is going to be so much faster. That alone is, actually, could be massive. And it’s just funny what is so overlooked. It doesn’t seem transformative, but it can be, you know?

Stephen: Yeah. I mean we had a financial client. Big, big client on AEM and we’re just like, “Hey, you know, there’s this thing called Target you could be using that you just haven’t connected.” And you know, it’s like the tech teams are inundated with these tickets. And so they’re like, “We don’t want anything else on our table. We can’t do anything.” We’re like, “Yeah, but you’re not gathering the data and storing the data the way you want to. And all of these other things that you want to do ultimately are dependent on—on connecting, you know, like your events with a data repository that—and then we could start segmenting and doing all these things.” so just sometimes those internal resistances, I get it. Like, and I have sympathy for their tech teams. I understand why they don’t want a giant, you know, like anything put on their plate. But, you know, it’s hard in those kind of institutions to get past the—the immediate client to the group, the whole tier of folks who sit at that level to the decision makers. For even something as simple as like, Can you just turn on this thing in your CMS that’s gonna help you a lot? And yes, it’ll take a little work, but it, it’s the investment. So outweighs the cost. 

Chappell: To kind of, Again, go back to our—You said—Well, how did you—did you say were the weird one in the panel, Julia? 

Julia: Yeah.

Chappell: To go to go back to our in-house perspective league. Okay. Let’s say you do manage to get a little budget and you can spend it towards building out some, some sort of transformative project for you, what would be the signs that it’s right to maybe hire out like an agency partner? And what is your advice to someone who, who’s doing that to help them make sure they’re getting the right partner for them? 

Julia: I think I look for partners when I require thinking beyond what I think we can do in house. And that is when your constraints—constraints can be a good thing, but when your constraints will actually constrain the thinking, then it’s all incremental. Right? And so I think that’s my—like Huff Post, we did this big redesign while I was there and like, it was really cool because it was all homegrown except for one piece. And like this poor designer had been like beaten down in all these different ways and she had all these great ideas and I was like, “No, let it all fly. Like do it.” And she did it and she—there were like tears when the thing launched. She was so proud of it, you know. But there was one piece that we knew we couldn’t do and that was the logo. We were like, we’re too close to it. And everyone had feelings about it and it was like, let’s get someone else to just show us some keynotes. Bring us on a journey about this logo, and it was better than anything we had done. And so like for me, it’s about if there’s transformation that I think my team can handle and can do really well and are actually good evangelists for change within the organization and the trust they have by being internal is an asset. And then there are times where them being, you know, on the inside will hamper their creativity and you know, they can be better inputs to someone else who can make a recommendation. And that’s how I think about it. 

Chappell: That’s a—I really like that perspective. It’s almost like kind of shifting away some of the emotional kind of entanglement. I’ve never heard that as a reason to work with a partner, but that’s. That’s so real. I’d say from the other, the other weirdos. You’re all weirdos. Let’s just face it. 

Stephen: Yeah. Come on. [laughs] 

Leyla: No problem. [laughs] 

Chappell: [laughs] for Stephen and Le yla, I hope you’ve had some successful partnerships with clients in doing transformative work. What does that look like? Like what are the qualities that you saw in those client relationships that made you know, this is good and this we are going to help them make a difference? 

Leyla: I think a decisive leader. I think that’s really critical. And then someone who understands their own organization, they know how to navigate, they know how to sell things in, they understand the pitfalls, how to kind of massage the language even in a deck. I think they—they know how to play the politics really. And then they’ve got a good sense of—I think instincts too? Because we’ll present ideas and sometimes we we’re really out there, right? And then sometimes we’re closer in. So I think a really strong sense of what’s gonna work given, you know, they—they just—they’re gonna know their business and—and everything else so much more intimately than we do. So I think it’s really a partnership for us to push and to prod and to—to bring in some outside thinking. A fresh take on the landscape, et cetera. But it’s really a partnership in them and understanding how it’s gonna be absorbed. So, yeah, I think it’s about a decisive leader who can commit and is willing to carry the work forward and kind of deal with their own internal politics.

Stephen: Sort of touching on—on your comment about when to bring in an agency. Sometimes I felt like being at an agency is a little bit—a little bit like being a therapist or something like that. When, when I was saying like psychoanalysis sort of just purely as an intellectual exercise, one thing that was striking was that like the analyst doesn’t know shit. They actually don’t know anything. What they are is sort of, they’re in a symbolic position of knowledge. So the—the analyst thinks that the analyst somehow knows the answer and to solve all of their problems. What that does is it lowers the threshold for—to allow them to speak. So when—as a content strategist, I’ve had a lot of in cases where, like as an agency, someone just believes that we have the ability to—to solve these problems. They’re willing to tell me all about all of the stuff that doesn’t work for them that makes their lives miserable. You know, I used to talk to every person who owned like a page on a website cuz I’m like, You know what? This isn’t a deductive job. This is inductive. I have to proceed without knowing the answer while framing myself as someone who has the solution—can provide the solution. But that kind of ability to come in as an—as a third party outside, to able to have the aura of expertise and hopefully some actual expertise too, and be able to start those conversations even from the ground up, for me was always a good sign that like I was gonna be able to have some impact now. You know, we can talk about how digital transformation is this giant, massive million dollar endeavor can succeed or fail. But I always liked it when I knew that nothing else there were boots on the ground whose livelihood depended on the performance of certain aspects of a website where I got to hear what they needed. I got to understand KPIs in a different way than you know when, when our data analyst comes in and just provides a data layer. You know, like has a slide in one of those keynotes. And was start to able to think about solutions based on what those real problems and—and provide that kind of inductive solutioning along the way. Because you could have a lot of like small wins even if that that giant sort of massive endeavor doesn’t ever reach its complete, you know, state of ideal completion.

Chappell: That’s so true. Like sometimes even if the bigger overarching goal, the big transformation doesn’t happen in full, doesn’t mean it’s a failure. You can still learn a lot and maybe move the needle a tiny bit. 

Stephen: Yeah. So those smaller concrete winds, you know, they add up and they start to help people understand how this process can build over time. We like to sell in those big engagements, but sometimes it’s—it’s about building a relationship that begins with—actually, again, I was sort of talking about user research, in our own ways. You know, like it’s not enough to have colder interviews with a bunch of C-suite folks and think that you understand this product and all of its pain points. It’s really about trying to make real differences in people—in people’s success, in their jobs, and in supporting this product that sometimes can earn you a lot credit along the way and help build up that relationship that could lead to more radical transformation. 

Chappell: This definitely ended up being more like wholesome and heartfelt of a discussion than I thought it might be. I was like, what if it gets too dark and we trash digital transcript? 

Julia: You like studied and everything. This was…

Chappell: I know. I just like, I was gonna play games. I was like gonna, I had no idea. But no, I think that’s a fantastic note to wrap our portion on—is really just this positive side of it making actual change. And so what I would love to do is turn it over. We have time for a couple questions. If anyone would like to ask of these expert slash weirdos as they are now, I will hand you a mic. 

Audience Member: So when Chapell is talking about when you have either a client or in house where you know that what they’re going towards is ultimately the wrong thing they should be going towards, do you have any strategies of how to pivot and realign to get on the right track?

Julia: Like a lot, right? I mean, I think we had there that—Yeah. I don’t know. I mean, there’s like the like—Yeah, take it seriously. That’s one thing. You take it real seriously, you’re like, “mm-hmm.” and you mock it up and you’re like, “We could do this, but we could do this.” Right? So it’s like they know you heard ’em, right? But you’re like, “But I can do it better.” 

Leyla: Yeah. That we’re actively doing that on a project right now. [laughs] I think the first thing is like what is your relationship with the other—the stakeholder client? Inter—internal—I’ve had to give some some brutal feedback. And it just depends on who you’re talking to cuz like that you got a really, really hard charging executive who’s like,” I know I’m right.” But also, “baby, you’re right.” so you know, I think the other one is asking questions—socratic method. Asking questions, having them play out the idea, especially in a group setting, you don’t wanna make anybody look stupid, right? Nobody likes that. And so I think talking it through, getting people to collaborate, driving conversation around something that feels like, you know, it’s not, not quite there. Again, you gotta be really sensitive though, because you don’t want “Emperor wears no clothes” syndrome either, but, But I think that’s another appoach. 

Julia: Yeah. And there’s also a don’t solve it in the room. That’s another one of mine. Which is like when someone’s starting to get like, “Oh no, no, and it should be like this and it should be like this.” you’re like, “mm-hmm . We’ll look into that.” Because the more you let the—if you argue, and the more you let them spin, they’re like, “No, no, no, no. I’m still talking, so I must be right.” And then you can’t get out of that, you know? So that’s one. 

Stephen: It might be a bit different for me cuz I’m not usually leading the product definition and, and that level strategy but you know what I do—am able to do is always show what systems are capable of doing. And so when there are ideas there, I—I think it’s a matter of, you know, sort of playing it back, but al also giving that alternative. And I don’t know how many Strawmen we’ve built that are specifically designed to reflect and, and ultimately turn down a client idea. But, you know, sometimes we’re wrong too. I mean, clients sometimes have ideas that at first we’re like, “Well, that guy’s an idiot,” but later were like, “Oh, he had a point. Like now that we understand certain kind of complexities.” So I, you know, I think that it’s about trying to first find out like, well, is there any scenario where this makes sense? And I can often, you know, in terms of, hey, We could do anything. Well, a lot of things with your content, find ways to sort of satisfy that feature need if we’re at that level while baking it into a different strategy—different product strategy. So I have a little bit more like flexibility in terms of being like, “Well, you say you want it to do this here. Look, this is it doing it, but in a completely different paradigm and achieving different results. But, I didn’t take anything away from you. We’re still saying, Hey, this was Jeff’s idea, and look at how cool it is in this completely different system towards completely different goals with completely different results.”

Julia: Yeah. 

Chappell: Yeah. That’s such a good one though.

Julia: I do that one too. 

Leyla: Yeah. Yeah. It’s like, “it’s no, but yes and.” 

Chappell: It’s—I call it like the wrapping the pill and the cheese, you know, for your dog. 

Julia: Yeah. For your dog. There’s another one, which is very big in my industry because historically publishing has been run by people who sell. Editors who sell big ideas or publishers who sell ads, frankly, right. And so like what talent sounds like in that environment is very confident and dis—It’s just different than digital incrementalism. The digital transformation I have brought to every job I’ve had is I’ve been like, “Why don’t we test it? Believe it or not, guys, we don’t actually have to decide anything in this boardroom today. None of you have to win and none of you have to lose. We can test it.” Now look, that’s expensive and like sometimes ideas are just bad and like you shouldn’t test them and we shouldn’t go through the dev effort of testing it and it’s just drag. But like I think finding a product person by, by training, I think finding that minimum lovable product, if you will, getting out there tested and then you get some data and then you’re like, “Hey, great idea guy. Here’s what we learned. Maybe it doesn’t look like a great idea.” But also I would also say, like, always look for—there’s a Jeff Bezos phrase where he says look for surprises in the data and double down. And I love that because it’s a flip on fail fast. Right? You know, it’s like when you, when you try and experiment and it doesn’t work, there are surprises in the data and figure out what those are, and then you double down. And I think that when you, if you can shift an organization from like, “you must do my big idea to be” like, “Ooh, let’s try a small version of your idea.” And then you can move in in the direction that makes sense. 

Chappell: Yeah. I—I often think it is just as valuable to show a client what they don’t need to waste their time doing and their money doing as it is to show them what they should be doing, because hey, at least we can cross that big idea off your list, you know? Yeah. Other questions. 

Audience Member: So we’ve sort of talked about, or it has been mentioned sort of “glo yo” analytic content strategy and sort of a bunch of other—and pivoted video, of course. How can I forget? I’m curious when you have these, whether they are trends, whether they are, are sort of large waves that seem to be moving through industries, and you’re trying to do things in ship and, and not have the app update, say bug fixes and small changes. How do you balance that with a degree of sort of the yellow brick road? Like that road’s not going anywhere else except for Oz and internally, externally, I’m just curious how you manage that kind of discussion where you sort of have a vision or at least a, a segment of a vision while also trying to balance all these other things that are moving around?

Leyla: Not all companies need to reinvent themselves constantly. So I think sometimes—like I, that’s where my mind goes to start. So sometimes just like the bug fix thing, like if you’re in a good place, you can afford to optimize for a little bit and then learn like what is the right next thing. I think sometimes that is like a bit poo pooed upon, like to—to be in a good place. But I think the, the balance for the other, like where you do need to change, we think, you know, the world around you is, is becoming very different very quickly. It’s a real—it’s really tough to figure out, I think, how to balance spending on the incremental optimizations. I, it just takes, I think, rigorous prioritization and being this is like, like another stupid industry thing, but like ruthless prioritization, but actually being very disciplined and very clear about who the decision makers are and testing, looking at the data, what is really working, what is not, And we need to like quickly make decisions. It’s kind of a cultural thing too. And being comfortable with that and, and moving fast towards the future, but also preserving enough of the status quo. You don’t like lose all your revenue overnight. I mean, I’m thinking of an app business cuz that’s where you’ve got me stuck. . But you know, on a larger scale too, I think there’s big decisions to make that you don’t want those to get in the way of just continuing to make money.

Julia: I get a little fuzzier about the North Star, I think. You know, like journalistic businesses like you, like we are mission driven and so we believe we are—we exist to inform the public. How do we make money off of that? We serve our customers better than anyone else. We serve our clients better than anyone else, right? And so like that doesn’t look like a big compelling product idea, though I have those too. Those may be wrong. Those can change. As long as it’s in pursuit of that North Star goal. And so I think there’s—there’s a certain fluidity around what the what is, as long as the why is—is unchanged. 

Stephen: I don’t have much to say, but you know, I do remember back when…

Leyla: I want to hear what you have to say!

Stephen: …when everyone in my field had to go out and tell everyone that somehow they were a publisher. And, and that was difficult because, you know, that just wasn’t true, to be honest. There were lots of people who weren’t publishers and, and never should have tried to be publishers. 

Chappell: Like the mattress company that like…

Stephen: Yes.

Chappell: ….made a million dollar magazine or something. Like everyone started—we had that period where at agencies, everyone came to us asking for to become a publisher.

Stephen: Yeah. 

Chappell: Which is strange. 

Julia: Publishers didn’t love that me that moment either. 

Chappell: Probably not.

Julia: Wasn’t welcomed. I think consumers, they were more indifferent, I think was the—But yeah, nobody was well served by that moment. I agree. 

Stephen: No, and it was a hard—it was a hard wave to fight and, you know, you couldn’t really do it and, and keep your job. So sometimes, you know, you’d really just kind of beholden to ride something out. Try to make sure that—that what you’re proposing is actually kind of scalable and you’re gonna propose something that’s absurd and then you’re gonna make sure that it could scale and, and have some sort of meaningful value. Yeah, in my experience there are times where you just, you know, have to ride the wave and crash—crash with it to some degree. And there are times where you could really intervene and, and try to make sure that people’s business reflects their DNA. And you know, when you try to change your DNA on the fly that’s usually a losing proposition. Having the folks in the room who understand who this company is, who we fundamentally are, and being able to sort of connect with them at that level, and then sort of branch out from there. Okay, well then if that’s really who you are, this thing you want is—does that connect to you? Or is there somewhere in between that, that maybe makes a little more sense? And I’ve had a lot of conversations of those types, which comes from working with a team who—who’s good enough to really understand the core elements of this business and of the people. And then to find those clients, those folks on the client side who are aligned with that. And aren’t just trying to do something they read in, in, in some fancy tech magazine.

Chappell: The—the tech magazine that might not exist anymore.


Chappell: Well, I wanna thank our in-house audience. This has been awesome to see humans in—in the meat space as we call it. I also wanna thank our—our audience out in TV land. If you are watching this somehow on a cathode ray tube style tv, please take a photo of that and send it to We will have questions and I wanna thank our panelists. 

Leyla: Thank you guys. This is so fun. 

Julia: Thank you. 

Stephen: Thanks.