Who Moved My Roadmap? Navigating the Unpredictable Future of UX and Product in the Era of AI

Donal O’Mahony has heard the phrase “once in a lifetime shift” so many times that it has lost its meaning. The dot com crash. Flash is dying overnight. A multi-billion-dollar acquisition that rewired a company’s culture. Now, generative AI is arriving with enough speed and noise to make even seasoned leaders feel like their roadmap has been stolen in broad daylight.

Donal steps on stage as Vice President of Experience at Contentful, ending the conference with a deliberately optimistic note. Contentful has a Berlin origin story, he says, and there is something fitting about talking in a cinema, in a city built on reinvention.

The talk title, “Who Moved My Roadmap?”, is a wink at anyone who has heard, “The roadmap has changed again.” In a room full of product and development leaders, that line lands instantly. Donal’s first move is to remove the surprise. Change is always happening. It is always going to happen. If you are waiting for a stable period where priorities settle down for good, you are waiting for something that does not exist.

Instead of treating every reset like a crisis, Donal wants teams to build the muscle to navigate it, without burning themselves out or losing momentum. The goal is not a perfect plan. The goal is direction and the ability to adjust without panic.

The Cheese Is Gone, and People React Exactly as You’d Expect

To explain why change feels so personal, Donal brings in a small book that helped him through upheaval at work and at home. It is called Who Moved My Cheese. He jokes that he is dyslexic and recommends the audiobook, but the point is serious. The story is a parable about four characters who find their cheese in the same place every morning, until one day it is gone.

Some characters return to the empty spot, convinced the cheese will come back if they wait. Some freeze, terrified of the maze. Some nibble the crumbs, trying to pretend that what is left will be enough. And some move, explore, and adapt.

Donal’s reason for sharing it is simple. People are hardwired to respond differently to disruption. When the roadmap shifts, the reactions you see across your team are not random. They are predictable. And the uncomfortable truth is that the response you choose shapes what happens next.

He is also careful to say this is not about forced positivity. He jokes about his hairline as evidence that stress is real. The message is more grounded. These moments will become your portfolio pieces. You want to look back on them with some fondness, not only as periods where you were stressed for longer than you needed to be.

Seismic Shift One: When Flash Died Overnight

Donal’s first story goes back to an era that now feels distant, but at the time felt like the future arriving. He joined an Irish company that was moving through a reverse takeover into Houghton Mifflin Harcourt, with an ambitious mission to digitize educational content for e learning.

Then the world changed in a chain reaction. The iPad arrived and instantly made tablets feel like the obvious platform for learning, especially for young children. The opportunity looked enormous. Interactive textbooks, 3D models, videos, science brought to life, all of it suddenly felt possible at scale.

And then Flash began to die.

Steve Jobs published his thoughts on Flash, calling out issues like security and performance. Whatever was happening between companies behind the scenes, the impact was clear. Flash, which had powered so much interactive content across education and media, was on borrowed time. Boardrooms that had invested heavily in Flash-based content woke up to a new reality. Everything had to be converted. Tools, workflows, and assumptions had to change quickly.

Inside teams, Donal saw the full spectrum of reactions. Some people saw opportunity, a chance to pivot from print into digital design, to build new skills, to shape a new craft. Some mourned the loss of Flash, then later thrived when they moved into newer ecosystems like Unity. Some played the familiar role of the person who lists everything that cannot be done, and why it will never work.

But the group Donal warns against is quieter. It is the people who see the change coming and do nothing. They keep building in the old way after hours. They keep using the old tools out of habit. They wait for the cheese to return.

Donal calls this becoming an OSA team, an “oh shit asteroid” moment, where you can see the comet coming and still carry on as normal. His advice is not to shame anyone for fear. Fear is natural. His advice is to notice it and then choose something else.

He shares a personal tactic. When a negative thought shows up, counter it with several positive ones. It can feel forced, but it stops fear from becoming your default. And he offers a better question than the one many teams use under pressure. Instead of “what’s the worst that could happen?”, try asking, "What’s the best that could happen?”

For Donal, that question led to real outcomes. He built a UX team. The work moved from static content toward user-centered digital experiences. One of the apps connected to the company’s work even landed in Apple’s App Store Hall of Fame. For a parent with young children, that was not just a career milestone. It was meaning.

Seismic Shift Two, A 2.4 Billion Reset

Donal’s second chapter jumps into telematics, joining Fleetmatics, an Irish success story that had floated on the New York Stock Exchange and had serious scale. He saw a mission to build user centricity and grow UX maturity, and he remembers being invited to UXDX around that time to talk about his plans.

Then the story takes a turn that anyone who has lived through an acquisition recognizes instantly. Donal returns from a family holiday and steps off a ferry to find several missed calls from his boss and the founder. No signal for hours. The kind of silence where you rehearse both outcomes before you finally hear the truth.

The company was acquired for 2.4 billion. Competitors were being acquired too. Leadership shifted. Org charts changed. The culture was about to be tested.

Donal describes the reactions as the same maze again. Some people fought the change. Some wanted everything to go back to how it was, the smaller office, the founder led certainty. People resigned. Others waited, anxious about what the new world would reward.

But Donal highlights the person who set the tone: the founder, Peter Mitchell. Donal speaks about him with genuine warmth, describing him as a change agent and a people person, someone who knew names and family stories deep into the company’s growth. That leadership approach mattered because it shaped how others responded.

The best that happened was bigger than the plan Donal originally pitched. Years earlier, he had talked about building a UX team of 25, ambitious for Dublin at the time. After the acquisition, it scaled to around 80 across continents. The company shipped more ambitious work, including safety technology that used AI-driven insights before it became fashionable to label everything as AI.

Donal’s point is not that acquisitions are pleasant. It is that they can unlock scale, investment, and impact, but only if leaders model steadiness and if teams stop treating change as betrayal.

Seismic Shift Three, AI Arrives on Day Thirty

Then Donal lands in the present. He joined Contentful, attracted by an API first, open, future-focused platform. One month in, generative AI arrives with force. He jokes that it felt like being handed dynamite. For some people, it was pure excitement. For others, it was dread.

Donal reframes the moment with a question. What is generative AI generating?

Yes, it is generating content, and he laughs at the timing of joining a company called Contentful right as content generation explodes. But it is also generating fear, anxiety, stress, and uncertainty. It can generate opportunities and innovation, too. The human reaction is part of the output.

So Donal returns again to the choice. You can choose fun, even inside confusion, or you can choose fear. Fear is natural. The work is noticing it and then counterbalancing it, so it does not drive the room.

North Stars, Not Fantasy Plans

When roadmaps feel unstable, Donal suggests a practical anchor: directional North Stars. He references Jared Spool and the idea of “concept cars,” visions that point two to four years ahead. Donal likes them because they create alignment without pretending to know the exact sequence of steps.

In Contentful’s early AI phase, the team created a provocative concept video. It was meant to spark conversation and provide direction, not to claim certainty.

But Donal adds a warning. Future thinking is useless if it is done in a bubble. The concept has to be shaped by the teams closest to customers, research, and delivery. The magic happens in the two-way exchange: strategic direction informed by real user contact, and tactical learning guided by a shared horizon.

Your Mindset Is the Real Portfolio

Donal closes with a reflection that feels almost like advice to his younger self. Enjoy this moment in your career. You will look back and realize these periods of upheaval were the work that shaped you.

Then he leaves the room with a simple truth. Whether you think you can or you think you cannot, you are right.

For Donal, the future of UX and product in the era of AI is not about clinging to a perfect roadmap. It is about building direction, staying close to customers, and choosing a response to change that you will be proud of later.

Want to watch the full talk?

You can find it here on UXDX: https://uxdx.com/session/who-moved-my-roadmap-navigating-the-unpredictable-future-of-ux-and-product-in-the-era-of-ai/

Or explore all the insights in the UXDX USA 2025 Post Show Report: https://uxdx.com/post-show-report