Digital Transformation: Three Stories
The ingredients for Digital Transformation are institutional pain, inflection points, and tools lying around, but you also have to get the people part right.
Before we get to today's main topic, some miscellaneous goodies and things that deserve your attention…
Help! For a future Dispatch, I'm thinking through different kinds of decisions, and I have two questions. First, what was an important life decision that you knew about ahead of time (e.g., where you were going to school, the person you wanted to marry)? Second, what decision did you only realize was a biggie after the fact? If these questions spark memories, please share them with me.
Nostalgia
H.R. Pufnstuf: On her terrific Instagram, Amy Sedaris surfaced "The Pronoun Song" from H.R. Pufnstuf, the lunatic 1960s kids show by Sid and Marty Krofft, This suggests that thinking about what pronouns we use isn't a new issue. It's amazing that Jack Wild (who played Jimmy) was 17 when this was filmed: he looks 10.
Best Blooper from Carol Burnett: Upworthy shared this pair of videos about a hilarious blooper from the last season of The Carol Burnett Show. (Watch both!)
Sgt. Pepper’s Lonely Hearts Club Band: Just eight years after The Beatles broke up in 1970, a movie retelling of their most-popular album came out starring Peter Frampton, the Bee Gees, Aerosmith, Alice Cooper, Billy Preston, Steve Martin, and more. It was an immense flop. Yahoo! has a retrospective worth reading.
I saw this movie in the theater: it was my first exposure to Beatles music. I can't think of any act today that—if it broke up today—would merit a major motion picture in 2031. Can you?
AI Chronicles
Writers vs. Generative AI: Don't miss the 7/18 episode of The Daily from The New York Times. Michael Barbaro interviews Sheera Frankel about both the Hollywood strikes and a wave of resistance to Generative AI from fan fiction creators.
One of Frankel's most important points is that Generative AI doesn't understand how human thinkers evolve over time:
The whole point of news is that what we’re bringing you is fresh and based on new reporting. So the conclusions we’re drawing for readers are constantly changing.
And AI can’t do that. It can only repeat and regurgitate what’s already been given to it, what’s already in the system. And so whatever answer it gives you might be what Sheera Frenkel thought about something two years ago or five years ago. But it won’t be what the newest idea is or the freshest reporting has brought readers.
This is akin to the distinction between diachrony and synchrony in linguistics. Humans exist and communicate across time (diachronic), but AI, at least for now, flattens that evolution into one single moment (synchronic).
See also Frankel's article with Stuart A. Thompson about this topic.
AI + South Park: I don't yet know what I think or how I feel about a short episode of South Park created by Showrunner AI. Axios has a fascinating article about the process by Ina Fried, who also features as an animated version of herself in the video.
Please follow me on BlueSky, LinkedIn, Post, and now Threads for between-issue insights and updates.
On to our top story...
Digital Transformation: Three Stories
Usually, when we talk about Digital Transformation, we focus on the physical: paper and ink newspapers dissolve and go online; albums become cassettes then CDs then MP3s then streams; physical books vanish into Kindles; videotapes become DVDs then Blu-Rays then streaming services; a taxi service that you call to explain where you are turns into a smartphone app that already knows where you are.
But Digital Transformation is really about people, not things. You can put anything into the Transmogrifier from Calvin and Hobbes, but if you can't change people's behavior then you're just wasting a cardboard box.
A few issues back, I shared three ingredients for Digital Transformation:
An external event or inflection point that allows you to change your standards,
Institutional pain that gives people an incentive to change their behavior, and
Tools lying around that help people do things differently.
My example in that issue was 9/11. At EarthLink (where I was the digital editor), we had a sneak preview of COVID lockdown: after the terrorist attacks, we all went remote.
Here are three more stories about successful Digital Transformation.
2000: From Documents to Wire Frames
This one is also from my EarthLink days. As digital editor, I was part of the group controlling the website, including new sections and special mini-sites. When I arrived at the company (the inflection point), the practice was to draft Microsoft Word documents that described the new web pages and send them to the requesting teams.
The problem with using Word documents to describe webpages was that it was like describing a rainbow to a colorblind person: a lot got lost in translation (the institutional pain).
The teams getting the Word docs didn't understand how the new pages fit together; this slowed everything down.
In my academic days, I'd hand-built small websites for my students at U.C. Berkeley. I knew that I could teach my team HTML, but it would take a while. Then I realized that we all had the full Microsoft Office suite on our computers. At that time, Office included an early WYSIWYG (What You See Is What You Get) web building program called FrontPage (tools lying around part one).
Instead of days to learn HTML, the folks on my team mastered FrontPage in an hour or two. Instead of Word documents, we created wire frames: simple websites with text and links so that the other teams could both read the text and click around to experience how it all hung together.
The challenge was that we didn't have anywhere to hang the wire frames online. Then I realized that every employee at EarthLink got a free account, and that every EarthLink account came with a small amount of web hosting (tools lying around part two). Using my free account, I created a space where my team could hang wireframes that the other teams could explore. It worked beautifully, sped up the whole process, and the other teams all loved it.
Then the Business Information Security team showed up in my office. They wanted me to stop hanging wire frames on my personal web hosting space because they worried that people outside EarthLink would get access to it.
"Can you give me a secure web hosting space that I can use instead?" I asked. They said they couldn't.
"Then no," I said.
"No what?" they asked.
"No, I won't stop hanging wire frames on my personal space. These aren't state secrets: this is marketing copy. If you can help me get a more secure space, then we'll use it. Until then, it stays."
I don't think anybody had ever said no to them before. Confused, they went away and never came back. Eventually, new leadership created a secure test space for us, but that was years later.
2006: Crowdsourcing a Spreadsheet
By this time, I was the Editor in Chief of iMedia Connection, a now-defunct daily trade publication that covered the intersection of digital technologies, media, and advertising. We were ramping up how much content we produced, which meant that tracking what we were doing while also guiding the process was wearing me down (institutional pain part one).
iMedia CEO, Rick Parkhill, told me to hire a Managing Editor to deal with the tracking part so that I could focus on innovating and improving the content.
I hired a guy named Mario. He spent his days lugging his laptop around the office, asking each editor for updates on the articles in process, and then hopping on AOL Instant Messenger to ask our remote editors the same question. He tracked everything on a Microsoft Excel spreadsheet that he emailed to me several times a day—an inefficient process (institutional pain part two).
That's when Google Labs released its version of Spreadsheets (both an inflection point and a new tool lying around), which anybody could access and update from any connected computer. Mario pitched me on converting from Excel to Google, which I thought was a good idea.
It worked! Although at first the editors required prompting to log on and update the spreadsheet, eventually the behavior became habit. Not only did we have a dynamic, always-current content tracker, but we also got about 50% of Mario's time back.
2020: Launching a Pandemic Daily Talk Show—IAB There
I joined the Interactive Advertising Bureau (IAB) as Editor in Chief in March of 2020: days before COVID lockdown sent us all home (inflection point). One job of a trade association like IAB is to connect the community it serves, which was hard when nobody could leave home (institutional pain).
Trade associations usually aren't quick to change, and IAB was typical of the breed. Also, if we had tried to launch a talk show during ordinary times, we would have spent a lot of time dressing it up, figuring out look and feel, creating graphics... perhaps even a set.
But we didn't have time for those high standards because people were lonely and scared. How could we let them know that—even though we couldn't meet in person—life and our industry continued?
We already knew that people could videoconference from home, which meant that they had internet-connected devices with webcams and microphones (tools lying around).
That was all we needed.
On Wednesday, March 18, halfway through my third week on the job, I said, "Let's launch a live-stream daily talk show... and let's do it on Monday." Ripples of panic went through the Zoom.
Somebody asked, "what are we going to call it?"
"IAB There," I replied. (The name is both a command to "be there!" and a Dad joke: it still makes me smile.)
On March 23, we launched with a conversation between me and CEO Randall Rothenberg about how the industry was reacting to the pandemic. The next day, IAB President David Cohen and I talked with journalist Tiffany Hsu of The New York Times about how quality journalism can save lives (a topic about which I'm still passionate.) The following day, EVP of Policy Dave Grimaldi and I talked with Michelle Klein, a VP at Facebook, about how online publishers were responding to COVID.
Because we moved quickly, the industry leaned in and rallied around IAB There as a new touchpoint. We iterated, creating a pre-show video package, organizing an editorial calendar that integrated with the rest of the organization's endeavors, and streamlining processes. We were so successful that IAB There was a positive agenda item for the next board meeting and started generating revenue within months of launch.
Although no longer daily or live, IAB There is still around, which is a happy thing.
Successful Digital Transformation is about people first—about changing behavior and letting organizational culture evolve. The technology part is secondary.
Thanks for reading. See you next Sunday.