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Creating a Language We Can Carry Forward: People get really good at bad habits. When we talk about digital transformation–and why it so often fails– we’re interested in more than software and systems . We’re getting at the heart of how people work with software and with each other. This week, Paul Ford and Rich Ziade discuss Upgrade, our new report about how real digital transformation happens, from idea through execution, and how to avoid failure. What are you waiting for? Upgrade is available to download for free here.


Paul Ford [Sings and holds the “a” for four seconds] Upgraaaaade [voice shifts down at the end as though he is shutting down]! [Music plays for 18 seconds, ramps down.] 

Rich Ziade Hey, Paul. 

PF Hey, Rich. 

RZ I wrote a document [mm hmm] that essentially is borne out of our experiences because when people come to us they don’t say, “Uh Rich, Paul, um I’d really love to digitally, you know, do my digital transformation. I’m behind on this shit.” They don’t say that [music fades out]. They say, “I’ve been using 11 CMSs across my 11 brands and it is time.” 

 PF “I—I need to get one thing here and it needs to integrate with this weird funnel system that we’re dah buh buh.” Yeah. 

RZ Exactly. Doesn’t sound as sexy but in effect it is a direct bull’s eye hit of what digital transformation is [ok]. It’s like, “I gotta upgrade. I’ve gotta get there. I’ve gotta find efficiencies and I need to empower users.” 

PF Ok this is a tricky thing, right? We don’t talk about this very much but the actual attractive aspects of this work are down in the weeds. Like that—or down—I dunno, in the weeds, in the ditches. I don’t know. 

RZ Swamp. 

PF [Chuckles] But you get there and it’s hard and it’s thorny and it—you end up drawing a lot of rectangles and boxes and you draw lines between them [yes] and you’re like, “I think if we move in this direction.” Like you can’t set up a piece of software and say, “We solved it.” 

RZ No. 

PF It’s different than that. 

RZ It’s messy. And [yeah] this document is borne out of our experiences in dealing with some of these efforts. 

PF I think this is what’s tricky about this business, right? Is that our marketing we tend to go out and be like, “We’ll stand up a slick, beautiful thing that will work great.” 

RZ Yeah. 

PF But our day to day work is dealing with complicated and messy human interactions that also involve complicated and messy software systems. 

RZ Yes. 


PF And trying to find a rational place—and we’re able to effect change there because we’re a little less invested, frankly [yeah]. We’re able to be like, “Well you want it to do this. It’ll take this and it’ll take amount of time and it’ll cost you some money.” [Mm hmm] And people are like, “Is that all?” [Yeah] And we’re like, “Yeah, actually.” 

RZ Yeah. 

PF Yeah. We can do this.

RZ Right. Right. 

PF So, ok, so you sat down at your keyboard, you put on your green visor and you said, “I’m gonna really make a difference.”

RZ Well I wanted to share some of the insights. 

PF Yeah. 

RZ And maybe provide guidance on how to get there, right? And the document is called Upgrade [good]. And it is a document in traditional form [yup]. Um it will be on—it’s free. It’s on the internet. 

PF It looks good! 

RZ I—I think so too! And—and, you know, it—it’s hard to put this stuff down. 

PF Yeah it is. 

RZ Cuz sometimes you could drift off into your own stories and— 

PF Look I’ve been push— 

RZ—it can be real dry. 

PF I’ve been pushing you to write this and then you were like, “Paul, you need to edit this. You need to take a look at it.” 

RZ And you destroyed it and— 


PF I did—I didn’t. I didn’t have to do that much to it. 

RZ It was great and I’m—I’m—I’m honored. 

PF I see this is like the first big step to us saying, “We will help you solve the—the harder, muddier problems.” [Yes] As a firm. Like the things that run for 18 months, the things that require a couple months to really just get them locked in and in place and there’s a—a [stammers] long period where you’re evaluating different solutions and we’re helping you build your product team. Like it’s just—it—it’s complicated, there’s lots of tracks, it requires a lot of mental and emotional energy to get the work done. 

RZ It’s way, way—and that’s kind of the theme of the whole document. It’s way more than technology. 

PF Alright, so why the word upgrade? First of all. 

RZ Well I—I—it’s—it’s almost always what you’re trying to do. There are—and bless their hearts cuz I find them fascinating—there are businesses out there that it’s like you—let’s say the two—the two doctor clinic. It’s just two doctors. 

PF Oh yeah! 

RZ And they have this system and it’s running on Windows 98 and they have a why bother attitude cuz like, “My patients are in here, I know how to get to them. [Yeah] I’m never gonna change this.” 

PF It’s sort of a pleasing kick in the face, right? 

RZ It’s great! Good for them [cuz they’ve—], man! [They have found] They don’t have to do it. 

PF They found the path and they’re like, “Why would I upgrade?” 

RZ “Why would I upgrade?” But for much of the world, especially businesses that are growing or competing, you have to keep going, you have to continue to find a) your—if you have customers, or even if you have users, even if you’re just running a call center, um the tools they have have to stay ahead of the game. You have to constant—I mean and if there are consumers then it’s a whole other game because consumers went from going to the mall to sitting on their phones and don’t make phone calls anymore. 

PF Right. 


RZ It’s just the new world, right? [Right] Like booking a plane ticket is a whole other world. 

PF Well, or they’ll just stumble over to Amazon. I mean it is—you—you have to—you need— 

RZ You don’t have a choice. 

PF You need an angle. 

RZ You need an angle and you need efficiencies and you need to find ways to get there. 

PF I think for the first like many years of my career the tools that were used in the back office, let’s say in media for the editors or for the people, you know, running the loading dock, or—just whatever it was, whatever the trafficking was of information through the organization, their tools were garbage and people wasted their time. It’s like, “Hey, it’s gonna take you 40 minutes to upload a video. Good luck.” 

RZ Right. 

PF And to me, first of all, I think that’s kind of a crime, that everybody just was like threw their employees under the bus in order to install some piece of software. 

RZ Yeah. 

PF But that’s where the upgrade can make the most difference. You can like sometimes get 20, 30 percent more productivity by, you know, making it less exhausting to move files around. 

RZ It—it is huge. Right? And sometimes it’s not even an upgrade, man, it’s just like, “You know what? We have 11 million users and it’s two websites and they—they kinda have to bridge with each other and the look—they look different [laughing] when they go from one site to the other and—” 

PF But see I feel there’s a— 

RZ It’s like a weird rickety bridge in between and they can’t get the dato—it’s just—it’s—it’s time. 

PF This all used to be all like a secret shame and now people—everybody kinda can talk about it. And I think there’s an understanding maybe because of the fact that like your CTO has been in the business for a while and actually knows how apps work [yup] as opposed to coming out of like pure IT or something like that but there’s this understanding that we just have to make it better. 

RZ Yeah. 


PF Like I can’t have my people burning hours and hours a day [correct] moving one rectangle to another and then it doesn’t work and they have to reset the computer [right] like that’s still going on. 

RZ Yeah. And there’s another key facet to this and that is the way design has matured into a key part of business investment. There was a day when cool, quirky, interesting design was sort of relegated and associated with brand and just look and feel and colors and then at some point, actually it took years to happen, it is understood, even by the biggest of consulting firms and the biggest strategists. The most senior people in big companies have to invest in and recognize the value of the customer experience or the user experience. It is part of business now [you know, I wanna make—]. There are entire departments now, it is absolutely necessary. There was a day when the bank didn’t need it and now every bank needs it. 

PF I wanna make an observation here too which is that the craft of design—I mean I think there’s still like like a lot of thought about brand and logos and type and—and sort of—[sure] like that’s still the core and grid systems and—and all of that. That—and those are the—then there’s the kind of overall look and feel and sort of the aesthetics and just being able to make it beautiful. It’s not just—but there is a—that fundamental aspect of user experience design where you’re thinking about modular sets of components that—that have interrelating qualities or like this is what a dialogue box looks like, this is how it works. You know I’m gonna make— 

RZ Systems. 

PF I’m gonna make one button and it’s gonna have 37 different varieties. 

RZ Right. 

PF Right? [Yeah] But it’s gonna be that one button at the core and if I can help people understand what the button’s for and why it looks like that at the core, I can give them a language and a grammar that they can use to design [right]. Where like—like design is more and more in this world about making a language that other people can take and—and sort of carry forward [right] and I—I feel that, again, like this has been a challenge for us and this is one of the things we’re trying to communicate because it’s not simple, and it’s not a—it’s not a clean, easy story— 

RZ Well the word design is evil at this point [right]. Like if I told my mom and, you know, I’m doing design work— 

PF She’d think you make jewellery. 


RZ Yeah. Exactly. Exactly. She associates it with just pure fashion and aesthetics [right] and not function. What—what happen—what’s happened is it’s arrived in business. It used to be a thing where you had to sell it. Like you should get user—I [stammers] I’m old enough to have gone through that. 

PF That’s right. 

RZ And to—to have seen it, right? 

PF That’s true. You need design as a category. Like just like— 

RZ It is part of budget. 

PF You can’t just buy technology [no]. You have to get design. 

RZ Yes. Exactly. 

PF Yeah. 

RZ So, that is the spirit behind this—this document and what you’ll find is it’s not technical. A lot of it talks about people uh and dealing with people, dealing with challenges you’re going to see, how to manage risk and risk oftentimes isn’t just software. It’s like, “My god, we didn’t get through—we couldn’t crack 72 percent of our tickets this week.” 

PF Mm hmm. 

RZ That’s not risk. That’s very quantifiable. 

PF Mm hmm. 

RZ The real risk comes from, “You know, that new project? It’s been nine months and we haven’t seen anything.” 

PF Right. 

RZ “We should probably ask for a review of where it’s at.” And that kind of risk— 


PF It’s worse too, you might go look at the—[Rich laughing]. Remember you have access to the GitHub, you know, [yeah] and you go in and you’re like, “Huh.” 

RZ Right! You peek in. 

PF “The velocity of—there haven’t been any code check-ins in three months.” [That’s right] And everybody’s working hard [that’s right]. A lot of meetings. 

RZ Right. Um and humans [stammers] the risk humans bring to an effort and we’ve seen this first hand. You—you—really good efforts that are just well meaning and they’re really busting their asses to get it done. They are just under fire. 

PF Yeah. 

RZ Under fire within their own organizations to try to get things done. Oftentimes they come to us and say, “I’m about to get beheaded.” 

PF That’s right. 

RZ “I’ve got 60 days.” 

PF That’s true. We have—we’ve had many existential meetings where they’re like, “I need this solution or I’ll probably need to go get another job.” 

RZ We—we have had that meeting and what that speaks to is the challenges around upgrading, frankly. That project was an upgrade. We’ve—almost all of our projects are upgrades. 

PF They’re upgrade—and they’re not full rebuilds. We’re taking the data, we’re taking constant— 

RZ It’s never that clean. 

PF That’s the thing and there’s a fantasy that you can start over and this is probably where we’re the most valuable, it’s almost like when people come in and say, “Invest in an index fund. Don’t think you’re smart.” You are not smarter than everybody who came before. 

RZ Right. 

PF Your—your job is to leave is better than you found it, not to blow up the world. 

RZ Mm hmm. 

PF For the most part. 

RZ Yes. 


PF Sometimes there’s exceptions but [yes] so our job is to come in and say, “No, there’s actually value here. [Correct] Let’s make it better [correct],” and to not like bring in all the weird corporate dynamics and— 

RZ Well that’s why oftentimes and I talk about this in the doc is people go outside [yeah] is that we do not carry the—the baggage and the politics of what’s inside. The challenge for an advocate that decided to hire out [yeah] is that it’s often read as betrayal. 

PF It’s not just that. Half of the time you and I have been—I’ve been in meetings with you where we’ve turned, both of us, have turned to the stakeholders in the room and said, “Listen,” and people start yelling at us [yeah] because suddenly there’s someone they can finally yell at [yeah] cuz it’s all so frozen up. 

RZ Which is fine. That’s part of our offering, by the way. 

PF It really is because it doesn’t—it doesn’t hurt your feelings. You’re like, “Oh!” I—I—it usually takes—you’re very quick about—it takes me like 30 seconds to be like, “Wait a minute, I’ve never met anybody before. Like I couldn’t have been—” [Rich laughs] You’re immediately like, “Oh come on!” But for me [yeah] I’m like, “Oh it might be my fault.” And then I’m like, “Oh wait a minute, no, no, this is like five years [Rich laughs] of problems that’s not my fault yet.” And um we’ll say in the room, “Look: you guys are yelling at us and you’re frustrated with us for being here but you’re problem’s with each other and so you need to work that out first and then decide if you’re ready to work.” 

RZ That’s right. 

PF And we’ve—I mean I’ve said those words and it sounds like it would be very uncomfortable, it’s actually not because it’s already so tense in the room [yeah] that acknowledging it actually gets everybody to go, “Yeah, I guess we do have some problems.” [Yeah] Because everybody does. So the upgrade, the key thing about the concept of the upgrade is sure, your systems and your software and your design are gonna get upgraded, so are the ways that you interact and build software yourselves in the future. Meaning that the real deliverable in a digital transformation isn’t just the software itself, it’s the way that people work together using that software. 

RZ Sure. 


PF You’re gonna make a system for the back office that allows them to communicate more efficiently. You’re gonna make something for the customer that lets them register their happiness or dissatisfaction more efficiently [yes]. Everything’s gonna speed up. That’s cultural change. 

RZ Yes. 

PF Ok so you’re delivering essentially a kind of management consulting transformation but you’re—instead of doing it through PowerPoint and reorganizing and firing and hiring, you’re saying, “Let’s just get this in place and see what happens.” 

RZ Exactly. 

PF “We’re gonna trust you guys.” 

RZ And that’s a lot of change and change makes people anxious. 

PF I know but there’s another thing. I remember once I was dealing with some bit of technical change and my boss at the time turned to me and said, “Give ‘em a minute. They’re higher primates.” Like— 

RZ Ouch.  

PF No! It wasn’t meant as a—it wasn’t meant as an insult. It was like, “We are tool using monkeys. We are good at figuring things out. Everybody just has to calm down.” 

RZ Yeah. 

PF It’s like don’t—you know, yes, they’re—they’re struggling and they’re saying, “I don’t know if I like this change,” or whatever [right] and it’s like, “Just give ‘em a minute. You know, let them—let them like work out the dynamics and let them play and learn. [Yup] And let’s see where we get.” And of course people—people figure stuff out. I’ve seen people lose their minds at some new product or new thing that gets put in front of them [mm hmm] and then two weeks later they’re like, “I love it! I can’t believe we’re—[yeah it’s an investment] I never wanna go back!’ 

RZ Well I mean this is— 

PF There’s a part in the doc where you talk about incumbents. It’s actually really relevant to this. 

RZ Yes. So uh I have a saying. Uh people get really good at bad habits. 


PF That feels—that feels like a personal attack. 

RZ It’s not meant as one. 

PF Ok. 

RZ If you’ve ever seen a—I think we’ve talked about this once before, I was checking into a hospital and she was using an old command line system to put my name in— 

PF Yeah like at the airport. 

RZ Like at the airport but she is flying. [Right] She is tabbing and typing and flying and when she makes a mistake she somehow navigates the cursor. This isn’t a—this isn’t a graphical interface, dude. This is like brackets everywhere and she is tearing through it to the point where if you came to that person and said, “Look: the 1981 [chuckles] system [yeah], you know, check-in system that you’ve been using as its time, that’s anxiety! That’s not like, ‘Finally! We get to modernize.’” 

PF It’s six months of transition. Like it’s—those— 

RZ It’s resistance and— 

PF I’ve been using the same text—we talked about this on the show—I’ve been using the same text editor for 20 years. 

RZ Yes. 

PF You make me relearn. I’ll do it. I use other text editors and tools but you take that away from me, you actually take away a lot of power and authority I have over my day to day life. 

RZ That’s—you hit it right on the head. It’s power and authority [right] and expertise. That’s their skill. That’s their—that’s their—“You are taking me from expert to novice. It took me 11 years to get here.” 

PF That is a very deep thing and I don’t think—people don’t talk about it seriously enough in our industry. 

RZ No. And what happens is if you are the advocate for this new effort that’s going to modernize that system, you are going to feel that heat. You’re gonna fee—you’re gonna have naysayers. You’re gonna have people questioning the—the value of it. 

PF But, you know what? And it’s not just that person. It’s her boss, it’s the people around who—who are like [oh yeah], “Che—Cheryl has—like she’s a master of that system and it works really well and we haven’t had a security incident in 20 years.”  


RZ Exactly. 

PF “So you’re gonna come in here, you gotta prove to me [yup] that you’re not gonna blow up Cheryl’s world and you’re gonna in—increase the larger risk to this organization which might I remind you is a hospital and anything can fall apart at any moment.” 

RZ And, by the way, which is why she is still on that command line system in 2018. 

PF That’s right. 

RZ I mean it’s real. They usually win those battles. 

PF They do and for good reason, frankly [yeah]. Like we tend to—everybody loves to roll their eyes at like failed IT roll outs but if the system had been better and the education and the change had been there—I remember talking—speaking to hospitals, I remember listening to somebody talk about how long it took to change the signage at Columbia Presbyterian Hospital [hmm] and how long—it was a seven year process to get new designed signage [that’s incredible]. Like, you know, “Here’s the parking garage.” “Here’s a little wayfinding tool.” Cuz it’s a giant labyrinth. Right? 

RZ Yeah, of—of course. 

PF And you had to find buy in and—I mean it’s just such a complicated process [it is] to get that kind of change and—and it’s so easy to roll your eyes. 

RZ Well that champion thinks, “Oh, ok, if I ship this, it’ll all come together.” And the pressures that are gonna come at that person that put their name, essentially, and their career behind [right] an effort like that, usually an effort like that that’s a career making thing. Like you will get that VP role. You brought them there. You modernized and now patients can login from home to check on their blood levels. 

PF It’s so—it’s so complicated, right? 

RZ Or whatever! 

PF So you got one group of people who are like, “If we could just get to this one point of progress, we can do all these other things,” and you have another group of people who are saying, “If you introduce this, you risk what’s here.” And both sides are basically exhausting and horrible after a couple of months of this fight. 

RZ Yes. 


PF Like they’re entrenched and they’re bitter and they’re angry in both directions and someone is about to get forced to do something that they don’t wanna do, either stick with the old system and, you know, start lookin’ for a new job. 

RZ Yup. 

PF Or change the old system and suddenly all sorts of skills and talents are irrelevant. 

RZ Yes. 

PF And that’s—that’s where we usually walk in and we say, “Hi!! [Rich laughs] How you all doin’?!?” 

RZ Well I mean it’s—it’s very hard to hire for stuff like this, right? [Oh god] I mean oftentimes you’re either buying the thing and you’re getting implementation people or you’re just hiring outside pretty much experts to think about this. We are not specialists in a particular domain [yeah], so oftentimes we have to learn the domain but we are experts in building stuff [that’s right] and designing stuff. There are a lot of examples like this and—and—and you—if you skim through the document it’s a lot about people [that’s right] and it’s a lot about how technology has to dance with a lot of the sort of the political dynamics that exist. I mean it’s called Upgrade but you are not upgrading your hard drive here. You are doing something that is going to affect a lot of people, that’s gonna make a lot of people feel inferior, make some people look bad, and it’s—it’s a very challenging, complicated uh path. 

PF That’s the thing: empathy is key. 

RZ Empathy is key. 

PF On both sides and it—it’s [yeah] so easy [music fades in] for it to get weird. 

RZ Yup. Well, Paul, guess what we don’t have to do this podcast? 

PF Promote Postlight. 

RZ [Chuckling] That’s cuz we’ve been doing that for the last two hours [Paul sighs]. Um we learned a lot. We’ve learned a lot in the last few years. Uh not just about technology which is just that’s our love but about how to advance within your business and how to make it happen and how it’s not just about technology, it’s about a lot of other things [that’s right, I think—] and you can get ahead of that. 

PF You know and it’s—when it’s—when this company started that was sort of my thought like, “Well, we’ll just parachute in and build you your software,” but it’s—that’s a lot of trust. 

RZ It is and— 

PF That’s what we’ve learned. We’ve learned to [in low voice] earn that [yes] trust. It takes a minute. 

RZ Yeah. And there are a lot of insights here. So check it out: Uh we’d love to hear what you think! 

PF We really would. We wanna know what you think. 


PF! Let’s get back to work. 

RZ Have a great week. 

PF Bye [music ramps up, plays alone for six seconds, fades out to end].