UX Had to Beg. AI Didn’t Even Knock

A Long, Long Time Ago

It’s 2013 in beautiful Knoxville, Tennessee and I’ve just been hired by a healthcare software company to build up a UX design team. The focus? Physician-facing and care team facing  applications and workflows. The kind of context where deep knowledge of how clinical users actually think and work isn’t a nice-to-have, it’s a requirement. 

Except that’s not quite what happened. Over the following months, through a series of smaller decisions and quieter conversations, the picture changed. The team never materialized and the role drifted. What they actually needed, it turned out, was someone to evaluate vendors and manage design relationships. An art director, something I had done before, pretty extensively. And yet…

The contextual knowledge that healthcare UX requires, the kind you build through research and iteration and repeated proximity to actual users? It got treated as a secondary consideration. Engineering was the center of gravity. Design just orbited it. I trained my replacement and left exactly one year after I started.

Two years later

At Siemens Healthineers, I’m sitting across from an engineering manager who has politely but clearly already decided this meeting is a formality.

We’re talking about PET scanner workflow software. The screens that a nuclear medicine technician uses to dial in radiation sensitivity, read radiological event data and confirm what’s been captured and what’s still pending. Heady stuff. 

The screens are all in black and white. Dense gray scale without much visual hierarchy. No color cues and no summary of present state. Just numbers and toggles that the technicians had been memorizing for years, because the alternative was slower.

I had some questions, and with tech constraints onboarded, I soon had upgrade proposals:  better resolution, colors to encode and depict radiation sensitivity ranges, a progress summary surfaced where it was actually needed and changes that would reduce the cognitive load in workflows where errors had real consequences.

The engineering manager looked at the mockups, and then at me, then back again at the mockups. “We’ll think about it,” he said.   That quarter, I ate a lot of catered lunches at my own brown bag events talking to engineers, clinicians and physicians as well as product managers, sales and marketing. 

Doing Reps – UX Adoption

Here’s what UX adoption actually looked like in that era, from the inside. 


Perhaps you were in a new practice trying to earn a seat at a table that had been set without you. Engineers and executives didn’t dismiss UX because they had evaluated it and found it wanting, but because it looked decorative. Soft and touchy-feely. The frou-frou department, one executive at another company once called us. (I’m not making that up.)

The resistance lived at the top and in the middle and the people with institutional authority were the skeptics. Which meant that one of the most promising paths forward was bottom-up proof. 

Meaning what? Patient, persistent and high-quality work that kept raising the bar. Usability testing session videos where engineers sat and watched real users struggle with interfaces they had built. HCI fundamentals explained in terms of sensory memory and visual processing, in the language of people who thought in systems. Brown bag lunches and hallway conversations. Prototypes that were better than anything anyone had seen before from a design function.

One full quarter of pursuing this at Siemens Healthineers and then…Then a YES.

Two companies, two shapes

They both circled the same problem: UX climbing uphill against institutional skepticism, converting the powerful through evidence they couldn’t easily dismiss.

There’s a documented failure mode worth naming here, one which Debbie Levitt wrote about in 2022 in UX Magazine: UX practitioners who responded to that skepticism by democratizing their work, running design sprints and workshops that invited everyone to “do UX,” inadvertently taught organizations that UX was something anyone could do. The tactics designed to build buy-in ended up hollowing out the credibility they were meant to establish. 

The ones who navigated it well held the line on expertise while still opening the door. Proof positive rather than participatory theater.

AI arrived differently

It didn’t send a calendar invite. It didn’t ask for a pilot program. The budget showed up first, and then the mandate. Then the all-hands where leadership explained that we were going to be an AI-forward organization, effective immediately, and wasn’t that exciting?

The resistance to this new influence flipped from technical and leadership to creatives and engineers in the trenches. 

We’re talking Design and Development, the people closest to the craft. Everyday users who had been handed tools they didn’t ask for and told to use them. These are the skeptics now. Not the executives, and not much engineering leadership. The people with institutional authority are already sold while the unconvinced are the practitioners.

Same adoption problem, with an opposing polarity.  So what does that reticence actually look like up close? Some of it is displacement anxiety, which is real and reasonable. Some of it is quality concern, also real. Some of it is ethical unease about training data, authorship, environmental cost. Some of it is something harder to name: the feeling that something is being done TO you rather than WITH you. That the conversation started without you and ended before you arrived. That last one sucks, doesn’t it?

Resistance Vectors

Here’s what I keep returning to… That the tactics that worked in 2013 were designed for a specific direction of resistance.

Brown bag lunches work when the VP needs convincing. They don’t work when the VP is already sold and your creative director is the holdout. You can’t mandate your way to bottom-up trust. And you can’t run a workshop that teaches skeptical practitioners that “AI is good, actually” without recreating the exact failure mode Levitt described. You’d be running AI evangelism theater, basically going through motions that signal organizational enthusiasm while building neither genuine capability nor genuine confidence in the people you most need to reach.

So what does the reverse playbook look like? I don’t think we have a settled answer yet, but some hypotheses are worth examining.

Proof by invitation, not assignment. Let skeptics choose their own first use cases rather than handing them one. The brown bag that worked at Siemens wasn’t mandatory. It was catered, which is different. People showed up because they wanted to, and left having seen something they hadn’t expected.

Honest failure visibility. Show where AI breaks, not just where it succeeds. Calibrated trust is more durable than converted enthusiasm. The usability testing videos that moved engineers at Siemens weren’t highlight reels. They were uncomfortable to watch, and that was a big part of the point.

Craft preservation framing over craft replacement framing. What does AI protect practitioners from, rather than what does it take? That reframe isn’t just spin, and more often than not it’s a more accurate description of what’s happening in the workflows where AI is genuinely working well.

Peer signal over executive signal. Who in the skeptic community is actually using these tools well, and are they visible? In 2015, the practitioner who moved me forward with engineering management wasn’t the VP. It was a senior engineer who had sat through a usability session and couldn’t stop talking about it afterward. Credibility traveled laterally before it traveled up.

None of these are prescriptions, and obviously the playbook for these tactics is still being written.

Next Generation Adoption Attitudes

One more layer of this problem is being built right now, and it’s further out than many folks are looking.

On a recent road trip, my teenager told me about AI at school. Compulsory exposure. Tools introduced without much context for why. Classmates who had concluded, from their first extended contact with AI, that it was something to be skeptical of or dismissed. Not because they’d evaluated it carefully, but because their introduction felt like something being done to them.

Sound familiar? The adoption problem isn’t just in current workplaces. It’s being reproduced downstream in a generation whose first impressions are forming right now. That’s a longer conversation and it deserves its own article. But it’s worth naming here: we’re not just behind on the current adoption curve. We may be behind on the next one too.

Wrapping Up

In 2013 the question was: how do you convince the people with power that this practice has value?  Well, we figured that out. Imperfectly and slowly, with more catered lunches than anyone should have to sit through. But we figured it out.

The question now is different. How do you build genuine trust with the people doing the work, when the people with power already believe?

I don’t think we’ve found the answer yet, but I’d love to talk with the bright minds working on it.

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#AIAdoption #AIAdoptionDebt #DesignOps #UX #Leadership #ProductManagement #EngineeringLeadership #FutureOfWork #NextGenerationTalent

Seeking The Real in an Artificial World: A Father, a Daughter, and the Midwest They Almost Forgot

A road trip from Tennessee to the Great Plains — eleven days, eighteen hundred miles, and the slow rediscovery of something you won’t find on screens. 


There is a particular quality of light in northwest Iowa in late May. It falls flat and wide across fields that stretch to the horizon without apology, past farmsteads that have been slowly disappearing for a generation.  The groves of trees that once marked where families lived, the outbuildings and modest houses, mostly replaced now by industrial metal structures and unbroken tillage. It is a landscape that has been rationalizing itself for decades, quietly trading the human scale for the efficient one.

Richard Lee drove through it with his almost-sixteen-year-old daughter Coraline in a 2022 Mustang Mach-E, an electric vehicle that required them to stop every 220  miles or so and wait. 

The waiting, it turned out, was much of the point.


Departure

They left Knoxville, Tennessee on May 22nd with a route planned through Nashville, Indianapolis, and across Iowa.  Ames first, then Alta and Storm Lake and finally up into South Dakota to Brandon. The stated purpose was family: Richard’s father’s side in Ames, his mother’s side scattered across northwest Iowa and the Dakotas. Extended family he hadn’t seen in years. Cousins who had never met Coraline, or had met her only as a small child and remembered nothing.

The secondary purpose was harder to name, but both of them sensed it. Something had shifted in their lives: a job loss, a year of high school and shared organizational chaos before that. A household that had been running on fumes and habits. Richard had been examining his patterns, the things he did on autopilot, asking whether they were actually serving him. The trip was, among other things, an experiment in presence.

What neither of them anticipated was that the most significant conversations would happen not at any destination, but in the car, in the charging stops, in the unhurried hours that an EV road trip imposes on its passengers whether they want them or not.

There is something that happens on a long road trip that is difficult to replicate by other means. The car is a bounded space, and bounded spaces change what people are willing to say. There is no exit. There is no other room to go to. There is only the road ahead, the music, and the person next to you.

They shared music. Coraline exposed Richard to more of Harry Styles than he’d heard before. The first and fourth albums both genuinely good, they both agreed, surprising them a little. Richard introduced her to Depeche Mode’s Violator, The Cure’s Disintegration, Nirvana’s Nevermind, Led Zeppelin II. She listened without irony, which is its own kind of gift from a teenager.

They disagreed, sometimes sharply. They kept talking anyway. True conversation is a lost art, and they practiced it without fanfare.


The AI Conversation

It started somewhere in Indiana, before they even crossed into Illinois. Coraline brought up artificial intelligence, or perhaps Richard did, it’s hard to remember now. Within minutes, the conversation had sharpened into something neither of them had quite said to each other before.

What Richard heard, listening carefully, was that her generation encounters AI almost exclusively through its negative expressions: the environmental cost of data centers, the displacement of workers, the degradation of learning. She had watched her mother struggle to find work for two years. She had watched classmates use AI to complete assignments without understanding what they’d ostensibly written. She had drawn a conclusion, one that was careful, considered, and firm.

“You had your whole life of learning things the old-fashioned way,” she told her father. “I want that too.”

It was hard to argue with. Richard, who has spent his career at the intersection of design, technology, and product, had pivoted through roles in ways that required him to rapidly absorb new domains and build mental models of unfamiliar systems. He had benefited precisely from having had to do the work himself. The pattern recognition, the cross-domain intuition, the ability to walk into a new environment and quickly identify what was the same and what was different: all of that had been earned, not automated.

He didn’t push back. He listened, and then he said: I hear you. And he meant it. Inside, the shockwave of her simple, heartfelt words rocked his world. Outwardly, dust from the cornfields suddenly made his eyes water, despite closed windows and an excellent cabin filter.

The conversation didn’t end there. It reopened later, more gently, after a period of silence in which Coraline put in her AirPods and read. Richard noticed his first instinct had been to take the withdrawal personally. That’s RSD (rejection-sensitive dysphoria) — the ADHD tax on ordinary human withdrawal  — but instead of reacting, he waited. Later, he approached her: I wanted to clear the air. From my perspective, it seemed like you pulled back. But it might also be my RSD talking. What was your take?

She appreciated being asked. They talked again, and somewhere in that exchange, something changed in the timbre of their relationship. In the willingness to name his own cognitive wiring without making it her problem, and to come back with curiosity instead of defensiveness. She was becoming an adult talking to another adult, one that cared deeply. But more importantly, to an adult who was truly paying attention.


Ames: The First Layer

Ames, Iowa is a college town built around Iowa State University, flat and orderly, with a particular Midwestern earnestness about it. Richard was born at Mary Greeley Hospital there, and Coraline had tracked it on the map before they arrived to make sure they passed it. She was right that they would.

They stayed at the house of Tom S. and his wife Erin P., cousins on Richard’s father’s side, who were away camping with neighbor friends for a couple of days. Richard walked through the house noting the accumulated stuff of life: music gear, tech gear, camera gear, books, workout logs, cobbled furniture, board games. The precise texture of a certain kind of mind. He thought: We are so alike in so many ways. I wish we lived closer.

Donna B. was waiting when they arrived. She was one of his father’s side of the family, a woman who volunteers at a local food shelter and knows where everything fits and why. They talked for nearly an hour after she helped carry things in. Richard said afterward that it was the first ‘real talk’ adult conversation he could remember having with her. She told him things about the family he hadn’t known: about his father and mother, about his grandmother, about the texture of relationships that had existed before he was old enough to notice them.

The next day was Memorial Day. Dick and Linda hosted a cookout at their home on the edge of Ames. Anna cooked everything herself and organized the day. Her children Juno, Ren, and Dax were there along with Dylan, Amy’s five-year-old. Along with Dax, he spent much of the afternoon demanding airplane rides from Richard.  Coraline was “kidnapped” by Anna and the kids and didn’t seem to mind at all.

Richard had a meaningful conversation with Anna’s eldest, sharing that he was neurodivergent and that he had come to understand his neurology as differentiation rather than disability. More of a different cognitive architecture with genuine strengths, not just a deficit to be managed. They received this quietly, in the way of someone who has been told many things about themself and are carefully sorting out which ones feel true.

Later, at Amy’s house, while digging in the soon-to-be garden Amy was working on, Richard briefly crossed paths with D, Anna’s husband. He was navigating his own recovery, doing the particular hard work of untangling childhood trauma from the person you’ve become. Richard recognized the territory. Neither said anything about it. Sometimes recognition is enough.

Inside, Coraline and Dylan were finding their home towns on a giant map on the wall as Dylan earnestly fumbled for the words to coordinate their exchange of contact information.


Storm Lake and Alta: The Roots

The day before leaving Ames, Richard stopped in to see Donna at the food kitchen where she volunteers, and a place she clearly belongs, moving through it with the ease of someone who has found a way to make her presence essential. He met her coworkers. He gave one of them a keepsake from the road, the retired gentleman who happened to share his name. There was a brief moment of recognition between two Richards with only the name and a morning spent helping others in common, and both of them appreciated it.

That afternoon, Richard and Coraline joined Dick, Anna, and the kids at Peterson Pitts, an outdoor swimming hole carved from what was once a gravel quarry, with water that reportedly reaches eighty feet deep. They swam, laid out, talked. Eventually the group thinned, and Richard found himself alone with Dick at the edge of something that needed to be said. They talked about Linda. Dick spoke about her dementia as though it were fairly recent. Richard, who knew Linda’s kids had documented signs going back to 2018, said nothing about the gap. Some things you absorb and carry. The afternoon Iowa light and cool winds set the place aglow and hinted at wilder lands.


The northwest Iowa landscape opens further as you head west, getting flatter and more exposed, the sky a larger presence. Storm Lake sits in Buena Vista County, surrounded by farms that have been in families for generations and a few that haven’t managed to stay that way.

Richard’s cousin Kurt E. farms a spread in the area. He’s  younger than Richard by about six years, and carries the particular competence of someone who grew up watching this land worked and then took over the job himself. Heidi, Kurt and Leah’s younger daughter, gave Coraline a tour on a side-by-side utility vehicle with the casual competence of someone who has been doing this since before she could reach the pedals. Later, on a different farm, a five-year-old boy would ferry her around on a four-wheeler with one hand. By the time Richard suggested she take the wheel of the Mach-E on a few miles of gravel road outside Alta, her threshold for what constituted alarming had been substantially recalibrated. If a kindergartner could manage livestock transport on a motorbike, she could manage a quiet stretch of Iowa gravel. She was right, and did fine. Of course she did.

Heidi wants to be a park ranger. Not generally, but very specifically. A particular park, a particular office, a particular desk. She showed Richard her room, which she has filled with Smokey the Bear memorabilia with the completionist’s attention of someone who has decided and committed. Richard was struck by the particularity of it. The clarity. The absence of hedging. Her older sister Hanna has been deep in FFA and 4H for years and is thinking about physical therapy and rehabilitation for children. Two sisters, two fully formed trajectories. Something in the household had given them permission to know what they wanted.

Kurt also solved Richard’s charging problem with the practicality of someone who has been improvising solutions since before machines could learn. After they’d confirmed the 220 solution worked with Richard’s charging hookup, Kurt ran to the machine shop and came back with a 220-volt adapter taking four prongs to three prongs, that fit the nearby original family farm’s existing RV connection at Bruce’s place. By 4 AM that night, the Mach-E was fully charged, plugged into a wood scaffolding between the old grain bins. It drew power from the same farm electrical system that had been running equipment for decades. No dedicated EV charger or subscription fees required. Adapt and proceed. 

The farm tour with Bruce (Richard’s uncle on his mother’s side) covered ground both literal and historical. Bruce has been adding to and modifying his farmstead for decades, designing a home expansion in his head during long bus drives for church groups and youth sports, working out engineering problems over years before putting a single nail in. He built the massive garage-and-great-room addition in stages, tearing out rafters once the plan had grown beyond its original scope, rebuilding ceiling structures on his back with barely enough room to work, adding a pocket door that necessitated a wall extension that necessitated a storage nook that turned out to be exactly right. A pantser, Richard called him. Flying by the seat of his pants.  Bruce laughed. 

Walking through it, Richard kept thinking: this is where I come from. This is where I get it. The perseverance, the patient dreaming of what a thing could become, the willingness to tear out and start again when the plan had grown. All of it recognizable, transposed into a different register of design and technology and product. Midwest farm logic applied to urban problems. It made him feel good to see the source of it. Maybe he understood his current challenges a little better. 

Coraline held a three-week-old piglet on the old family farm. She was glowing, much like Richard and his sister Kirsten once did.

Diane put on a traditional Iowa meal: corn cut fresh from the field and fresh from the freezer, coleslaw, potato salad, bratwurst, pork burgers, watermelon, Jell-O salad. They ate on the back deck in mild weather, talked family history until the sun went down, and called it a night. 


South Dakota: The Furthest Point

Sioux Falls itself, and Brandon, South Dakota (just east of Sioux Falls) sit on the edge of the Great Plains proper. The landscape shifts as you cross the Big Sioux River, with the gentle Iowa roll giving way to something harder-edged, more Rocky, with outcroppings that feel like a preview of the West. Richard woke Coraline up at that crossing. She stayed awake after that. 

Hope, Jenny’s daughter, was visited first, and her house was a genuinely lovely space that could have been featured on HGTV. Her husband Josh is a professional painter whose work was visible in every room, their two boys Parker and Calder providing the particular ambient energy of a two-month-old and a very alert two-and-a-half-year-old. He’d already catalogued the satellites visible above the backyard and corrected his grandfather’s pronunciation of a friend’s name with patient precision. These were the youngest of the 20 cousins Coraline “collected” on the trip.

Jenny D., Richard’s cousin on his mother’s side, lives in Brandon with her husband Neil and their son Griffin, the older kids having already fled the coop.  Richard hadn’t seen her in years. She is one of the people he’s felt most connected to in the family, and the visit reforged that connection. They talked late into the night, first sitting in the Mach-E at a Pilot Flying J charging station while the battery crept up from low, and later on Jenny’s back deck overlooking a sizable creek. They stepped through the things that don’t get said in texts or holiday phone calls: what actually happened those summers long ago when Jenny stayed at the farm, what her childhood had really been like, and what she and Richard had each gotten wrong about the other’s experience. They engaged with each other’s false perceptions and gave them up. It was cathartic, as these conversations tend to be when they finally happen, and worth broaching after years of delay.

Neil shared about his ADHD diagnosis the previous year. These things often come later in life, with the particular reverberating quality of a late diagnosis: everything re-examined through a new lens, years of confusion suddenly making sense. Richard shared he’d be happy to talk about it with him. Neil’s experience as a pastor at his church, a large, conventional congregation that had responded poorly to his diagnosis, was the kind of institutional failure that is hard to describe without sounding like you’re exaggerating. Jenny seemed bitter about it. Richard was not surprised. He’d borne the brunt of coming out to institutions in recent years, and still bore the scars. 

Griffin and Coraline stayed up talking until 1 AM, in the same room, in the same positions Jenny and Richard had left them in, apparently finding in each other some similar frequency. The next morning, the olds regretted the hour slightly, but no one regretted the conversations.

Janet and John came to dinner. Games were played, and there was much laughter. Also ice cream and cake, because “midwest sweet tooth” is a genetic condition. Richard walked them out to their car afterward and they talked about the improvement in a family member’s behavior over the last year and a half: more communicative, more present, more connected to their family. This reminded Richard of Tom discussing having seen signs of his mother’s dementia. The two conversations, days apart, sat in Richard’s mind like photographs taken from different angles of the same subject: distance and its impact. 


Des Moines: The Big City

“AI is like fire,” Richard told his uncle Ed D. during a conversation they had while once again charging the EV in Des Moines.  Their discussion had wound its way from tech support to family history to the future. “It’s an elemental force. It can be an amazing tool but it can also be incredibly destructive. You have to decide which, and work to make that the reality.” Ed agreed, in the pragmatic way of someone who has seen enough of the world to know that elemental forces don’t wait for your opinion. “It’s turtles all the way down,” Richard added. Terry Pratchett. Ed appreciated it. Charge complete, they headed back to the house. They found Coraline and Richard’s aunt Joan going through old family photo albums, two of which made it back to Knoxville. 


That night everyone local met at Christine and Brandon’s place for dinner and a swim in their pool. Izzy (cousin #20 !) and Coraline hit it off, future pen pals most certainly. 

The next morning Ed and Joan fed Richard while Coraline slept in, before packing for the outbound trip began. Joan made espresso and they talked about Steve, their son that died 14 years ago.  The day following our visit was his birthday, and they were having an annual birthday party in his memory – sixty people – classmates, parents of classmates, friends who became friends through grief. A kind of testament to what can grow from loss when people choose to tend it.  Faith, family, friends and the church community are a big part of it for them. 

Richard was grateful they shared the story, and realized that the sharing itself allowed a long-forgotten wound of his own to heal. It shed light on how parents can deal with grief of that magnitude – something he’d struggled with since having kids of his own. 


The Thing About Screens

At some point during the trip, somewhere in South Dakota with good company around and no particular reason to reach for a phone, Richard realized he hadn’t opened his laptop once. He had barely used his phone for anything except navigation and coordinating logistics. This was not a digital detox in the performative sense. It was simply that there was too much else happening. More meaningful stuff. Real stuff. 

The families he was visiting were not living in opposition to technology. They used it, navigated it, struggled with it when it stopped working (Richard spent a notable portion of one afternoon doing tech support on a password recovery issue, his interface-specialist instincts fully engaged). Technology was instrumental there, but in service of lives organized around land and seasons and relationships and the practical accumulation of skill. 

What the trip made visible, by contrast, was how much of ordinary life has become organized around the screen as a destination rather than a tool, the thing you go to when there is nothing else. Increasingly it’s the thing you go to INSTEAD of something else. The data centers are multiplying across Indiana farmland and smaller cities, visible from I-65 and impossible to miss. The scale of them feels wrong in the way that only becomes obvious when you’re driving past at highway speed. They’re simply the infrastructure of that orientation made physical. 

The family in Ames talked about them too, in the abstract: entire sections of land that once held multiple homesteads now holding monolithic industrial structures and nothing else.


What Comes Back

They drove home through Des Moines, and back through Ames for one more night with Tom and Erin and their kids. There was a workout in the basement, a late night conversation, and Coraline and the kids picked up exactly where they’d left off. 

Indianapolis was a different story. Ford’s navigation system, blissfully unaware of construction that had closed multiple exits and rerouted entire roads, nearly guided them into an accident. Richard pulled off onto side streets and into a mall parking lot, took a beat, spotted a police cruiser, and rolled up slowly with windows down and a friendly wave. The officer helped them find their route to the hotel. Richard gave the cop a blue mug in thanks. He mentioned to Coraline afterward: this is what that interaction looks like from a position of privilege. The acknowledgment mattered. She heard it.

Then south and east through Kentucky instead of Nashville. That shaved an hour or two off the return and offered the particular pleasure of horse and bourbon country in late May.

By the time they got back to Knoxville, something had shifted. Not dramatic, not cinematic. More like a recalibration, and a reminder that the people on the other end of a phone number are living full lives in places with real textures. That texture is only available in person.

Richard came back having not had a drink in eleven days. He wasn’t a problem drinker but he was a regular one, consistent to a fault. He had slept in hotels, in guest rooms in the homes of people who knew him when he was young, and he hadn’t felt the desire at all.  He did wake up with a headache some mornings and figured that was likely related. Those were managed with aspirin and coffee. He took it in stride and noted how he felt more present.

Coraline came back having held a piglet, having driven on a gravel road, having met 20 new cousins who became real to her in a way that photographs on a phone screen had never managed. She came back knowing that her extended family, distributed across Iowa and the Dakotas, living full, strange and interesting lives was worth knowing even more than she had understood.

They did not go to Paris or Patagonia. They drove through Indiana and across the flat spine of the Midwest, stopped at truck stops and Meijers, slept in guest rooms and ate Jell-O salad. They visited people who remembered Richard as a child and met Coraline for the first time. They charged an electric car from a grain bin. They swam in a flooded quarry. They were licked by baby cows and made a fainting goat actually faint. 

And somewhere in all of that, between time in the car, in the kitchens and on the back decks… As the sun went down over fields that have been planted and harvested for hundreds of years, something real happened. The kind of reality that a cruise ship or a European itinerary cannot manufacture. The kind that requires history, and people who share yours, and enough unhurried time to actually say the things you’ve been meaning to say.

There is a persistent cultural myth that the trip which changes you must involve a passport, a long-haul flight, and photographs in front of something ancient or impossibly scenic. That this transformation requires distance in geographical, cultural and linguistic terms. That you have to go far to go deep.

Richard and Coraline drove to Iowa. 

The Long Way Around

On a recent cross country road trip with my daughter to see family in the Midwest US, we had a lot of ‘captive audience’ time to chat.

Lots of breaks too, as we took my EV — and while that’s incidental, I can confirm that experience was very manageable, and less fatiguing by far than similar trips in an ICE vehicle.

In discussing our generational perspectives (dad @ 52, kiddo @ nearly 16) topics came up that included music taste, plans and hopes around driving & cars, having kids of their own, how they’re thinking about college and the career path following… and AI.

I want to zero in on a moment when we had moved to discussing AI in her educational experience — from 3rd grade to being a rising sophomore in high school.

We’d talked a bit about her concerns for her classmates tempted to cheat and take the easy road. About their failure to learn how to think for themselves and learn how to learn well. About whether college will pay off for those that take that path. About whether her parents will find good jobs once more.

She’d gotten quiet after I’d asked how much she knew about the positives, the potential upsides that come up in global AI discussions… and I let the silence continue, giving us both some space. Then she said something that simply floored me with her reflection and wisdom:

“Dad, you had your whole life to learn things the old fashioned way, manually. You got to make mistakes and learn from them. You learned from books and from people and from experience. I want that for myself.”

I felt the earth shake. I may have teared up a little — but that was probably just dust in the air. We were driving through an area with nothing but fields of corn and beans, after all.

“That… makes a lot of sense, kid.”

The 30-Point Sprint: How Leaders Hoard Capability Instead of Building It

A staff engineer at a scaling tech company told me about their managing director — someone with organizational authority, access to the best AI tools, and apparently a lot of enthusiasm for using them. The director had assigned themselves 30 development story points in a single sprint. The rest of the team was carrying 6 to 16 each.

“They vibe code everything,” the engineer said, shaking their head. Their team was left babysitting that output.

I’m not here to cast shade, and I’ve seen enough versions of this pattern to know it’s rarely malice — it’s excitement without governance. Glee without the long view. AI makes execution feel effortless, and when that feeling hits someone with organizational authority, the natural instinct is to run with it and stay in motion.

But I keep thinking about what a different story that could have been.

Imagine the same director, the same tools, and the same gap in formal coding skill. Instead of assigning themselves 30 points, they walk into a team standup and say:

“Here’s the problem I was trying to solve, and this is how I approached it with AI. Show me how you would do it the traditional way — and then show me how you would do it with the AI tooling we’ve implemented. Let’s talk through the strengths, drawbacks, and leverage opportunities for all three approaches.”

How different would that be for the team? For that leader? For the org’s health as a whole?

That’s not a weak play. That’s one of the highest-leverage moves a leader can make — using their own ignorance as an opportunity to build a structured learning platform. The team gets to teach. The leader gets to learn. The org gets a three-way comparison that surfaces assumptions, tradeoffs, and best practices that would otherwise stay locked in individual heads — or leave entirely when those people move on.

It becomes a running growth exercise. It compounds, to the good, for a change.

Instead, the reality

30 story points for someone who should be focused on meta-level engineering concerns. A team stuck babysitting their leader’s output. And an opportunity for something genuinely great quietly wasted.

AI gives leaders without deep technical chops a real reason to lean in — not for the first time, but never has it been so readily accessible. The question is whether they use that access to hoard capability or to build it.

The answer is what separates a manager from a leader.

Originally shared on LinkedIn.

A New Job Is Lurking Inside Your Design/Product Org

AI capability inside a design org doesn’t distribute itself.

Enthusiasts will adopt it, of course. They build their own local workflows and see some gains. They may hoard the knowledge — not out of malice, but because nobody’s asked them to share it around. Everyone else keeps working in more traditional fashion, often quietly ashamed of their (self-diagnosed) ignorance.

This is AI Adoption Debt. And it’s not a training problem. Training can build knowledge, but it doesn’t build systems.

The role that builds those systems is forming right now inside mature design and product organizations. It doesn’t have a consensus title yet, and in most orgs, it doesn’t exist at all. Many don’t even know they need it.

What the role is not

It’s not a prompt engineer. It’s not an AI evangelist. It’s not a design technologist in the traditional sense, and it’s not a product manager for your AI tooling budget. Those roles exist and they matter — but they’re not this.

What the role actually is

The role’s primary responsibility is managing organizational AI adoption infrastructure — ensuring that knowledge compounds across teams rather than concentrating among early adopters. It sits at the intersection of DesignOps, systems-level organizational thinking, change management, and technical depth (without requiring engineering-level skills).

AI doesn’t speed up decision-making. Decision-making is still the bottleneck. This role builds the systems that distribute AI leverage equitably across the org so that the bottleneck doesn’t also become a single point of failure.

Building that infrastructure calls for a specific mix of skills

    • Deep familiarity with design practice
    • Systems-level organizational thinking
    • Change management expertise
    • Technical depth (not engineering-level, but fluent)
    • Accumulated judgment and pattern recognition

The 5th dimension: A foundation of judgment

The first four are table stakes. The fifth — judgment — is what separates someone who can describe this role from someone who can actually do it. It’s the ability to read an organization’s readiness, sequence interventions correctly, and know when to push and when to wait. It accrues slowly, can’t be hired in from scratch, and is what makes this role genuinely hard to fill.

Where the role is “beaming in” right now

It’s appearing most visibly inside organizations that have already built mature DesignOps functions. Those teams have the operational muscle memory. They know how to run programs, own shared infrastructure, and manage change at scale. The AI layer is new; the organizational pattern is not.

It’s also showing up in product orgs — particularly in companies where product operations has developed enough structural maturity to absorb a new domain.

Why it doesn’t yet exist

Because most organizations are still in the tool-buying phase. Leadership approves the budget. Individuals experiment. Ninety days later there are a dozen parallel workflows that don’t talk to each other, and one or two enthusiasts burning out trying to carry everyone else toward the goal post.

Nobody paused to ask: who owns the system?

What to do if you’re building a design or product org right now

    1. Audit honestly. Map who’s using AI tools, how, and what’s been shared beyond their immediate team. The gaps will be obvious.
    2. Assign ownership. Not enthusiast ownership — organizational ownership. Someone with design knowledge, organizational authority, and an operational orientation.
    3. Start with vocabulary. Shared vocabulary is what makes it possible for a new hire to be productive in weeks instead of months. It’s the cheapest, highest-leverage infrastructure investment you can make before building anything else.

The organizations that recognize this structural gap early will have a compounding advantage over those waiting for the formal job title to arrive before they act.

The role is forming. The question is whether it forms intentionally inside your org, or by accident.


Originally published on LinkedIn on June 2, 2026.