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

Donal O'Mahony at UXDX EMEA. Video: https://youtu.be/VzBoT1YG-lc

Readable transcript: edited from the recording's captions for readability (fillers and false starts removed, punctuation and section headings added). Wording is the speaker's own. Timestamps are positions in the video. Names marked [?] could not be verified against the audio.

Who moved my roadmap?

[00:00:07] Hey everyone, thanks so much, and what an incredible two days. An incredible venue as well. There might be a bit of a cinematic theme to this as well, if you keep an eye out for that. As AJ said, I'm Donal O'Mahony. I am the VP of product experience in a company called Contentful.

[00:00:31] Just to give you a little bit of context on this: a very proud Berlin story, a hugely innovative city, and massively proud, and a shout out to the Contentful team, some of whom are here as well. It's an origin story that's in Berlin. I feel very privileged to be talking to you from that perspective, and also the origin story of UXDX from Dublin.

[00:00:53] A little bit about the company. The company really defined the category of what's termed headless content management systems, and at a point in my career I wanted to move to a company that was API first, very visionary, very future focused, and it was an open platform, so I moved for that reason. Now it's making a strategic move to a digital experience platform and has recently acquired a personalization product as well, again from Berlin, so more on that later. But I want to set the context, and also resisting using two letters, like a lot of people.

[00:01:28] Okay, so the title is kind of tongue in cheek, which is "Who moved my roadmap?" There's been so much disruption, and let's face it, it's mainly product in this room, and we know the feeling of hearing the roadmap has changed again. But I just want to reassure you that this change is always happening and it's always going to happen.

[00:01:47] Any film buffs or Kubrick buffs, the subtitle there is a reference to Dr. Strangelove, but it's basically how to love and embrace the change. And as I was introduced as well, I did play with the idea, potentially, of being told at the time this is a once-in-a-lifetime seismic digital transformation moment. I think as you can tell by the hairline and the hair color, I think I'm on my fourth of these. So I want to end the entire conference with optimism, and please don't waste your career worrying about the now and the future. Try to enjoy the now. The future will sort out itself.

Who Moved My Cheese?

[00:02:29] I'm going to recommend a couple of books, which is funny because I'm dyslexic. Go audio books. But this one kind of changed my life after a massive acquisition in the previous company. The book itself is called Who Moved My Cheese? It's really small. You could read it on a plane journey, a train journey, maybe even a long tram journey. In a way, I'm trying to describe it through... it's a parable, basically. Very, very simple to understand, but it's capturing the fact that people really react to change in different ways. It's the way we're hardwired.

[00:03:06] But to describe it is kind of difficult, to describe a book. So I did ask ChatGPT, in light of the fact we're in a beautiful cinema in Berlin, I asked it to produce a poster for my children to describe the book. Here's what it proposed, and I absolutely loved it.

[00:03:23] What it's describing is four characters always consistently going to the same place in the maze for their cheese every morning, and one day the cheese is gone. I see some smiles of people who've already read the book, and some are, what are we going to do? When is the cheese going to come back to where it was? Nibbling on the crumbs that are left behind. Some kind of sensed there was going to be some movement of cheese, and even other stations they knew around the maze. And then some were just terrified about it ever happening, and then terrified when it did happen.

[00:03:58] It was quite incredible. But when I read this book, I was a father of three children at the time. They were going to be teenagers. Life was happening. Geopolitics was happening. Acquisitions were happening. So it actually was a hugely helpful book for me for dealing with change in every aspect of my life.

[00:04:13] So I did another prompt, as we do, and part therapy as well. Massive shout out to the previous speaker. I asked it to do some variations on the theme, and instantly this is what it presented. My favorite one is the dyslexia in images of ChatGPT. Makes me like it a little bit more, and misspelling, which I do. Tariffs. Who moved my tariffs? And then down the bottom, it's super clever. It said "coming to a market near you," which is kind of fun, and finger on the pulse as well.

[00:04:49] All joking aside, it's a phenomenally powerful book for you to help process change, whether you're an introvert, whether you're fight or flight or fear or freeze. My talk is really about, please, you can be all of those things, but please try and have fun and look back on these massive changes that, let's face it, they're going to be your portfolio pieces. Please look back with fondness. I should get a commission on this book, by the way.

[00:05:14] The main takeaways, or the cheesy summaries as I like to call it: change is inevitable. There will be another one as big as this, probably related to AI, but there will be another one in the order of four, five, six years. Pamela described that really well from SumUp at the opening of day one, which is, these cycles are ultimately tech and economic cycles, and there will be another one. So it's inevitable. So kind of just deal with it. I know it's harsh to say, but different people react to it differently.

[00:05:47] In the three case studies, these are examples from my teams and the teams I've been part of in my career, I want to tease out how some people reacted differently, and then our response to it determines our fate. Whether you're a visionary or whether you're a pragmatist or whether you're "the sky's falling," these are the different people reacting differently. The power of embracing change: I really recommend that. I want to go back to talk to myself ten or fifteen years ago. And then the handwriting on the wall. We're probably seeing the start of the handwriting for the next wave on the wall already, so some people are incredibly plugged into that.

[00:06:25] As it was mentioned there as I walked on, I've been told multiple times this is a once-in-a-generation moment, a generational seismic change. That seems a bit weird, because I think I'm on my fourth one. Started in the dot-com bubble bursting, and I was made redundant three times in two years and went back to be a college lecturer to pay the bills. But what I would say is embrace it, enjoy it, and you're going to be sorted psychologically. You'll be much happier.

Chapter one: Flash, the iPad and Houghton Mifflin Harcourt

[00:06:53] A bit part therapy again, but tell me about your childhood. If it's a time machine now, I'm going to take us back a couple of years. I was a proud father, three young children, wanted to make a difference in the world, and I joined an Irish startup that was moving from what was called Riverdeep to Houghton Mifflin Harcourt, which was a reverse takeover of many publishers in the States, with a vision really to digitize content for e-learning.

[00:07:22] I was exceptionally excited about that. This is the kind of quality content the team there... I haven't worked there in years, so I'm not taking credit for this, but this is the kind of standard content we're all familiar with. A big Irish success story as well, but now a very proud American and global reach.

[00:07:38] But when I joined, it was Flash-based CD-ROM. Flash, Macromedia. Do you remember Macromedia? I was a Flash designer. It was a revolution for creativity. And Director, Lingo, ActionScript, all blown apart now. Thanks for shouting out Director, I love that whole suite. Acquired by Adobe. And then this happened.

[00:08:04] Now, this is hard to describe, the first year, year and a half. So I did this. Let's break this down. In the first year, the iPad came out, and the glaringly obvious use case, and normal for us now, is for e-learning for young children to use it. It was revolutionizing instantly, hugely exciting. And again, ChatGPT can't even do ABC, and I decided not to fix that.

[00:08:33] Now this is getting a bit surreal. Maybe I'm hallucinating. Maybe. But Arnold Schwarzenegger was the governor of California, for anyone from America. I think that was true. And excitedly, and in partnership with Apple, he announced free iPads for a cohort of the school children in California. That was exceptionally good news for companies like ourselves and many edtech companies. So that's incredibly exciting.

[00:09:01] Anyone jumping ahead sees a very sad spoiler alert for Flash designers. Then Steve Jobs wrote a letter which was "Thoughts on Flash," and abysmal security. I don't know what was going on in the background between the companies, etc. But it killed... CPU hog. It killed Flash overnight. It took a year.

[00:09:21] I'm being a little bit cheeky here, but not just HMH, but every corporate headquarters that had Flash-based content, gaming, education, instructional design had all moved to Flash instantly. Remember the whiplash of yesterday? Instantly had to convert all their content to HTML5, convert to Unity, etc. So many boardrooms, many companies were like, WTF is probably the best way to say it.

[00:09:50] And I was kind of excited. Like, I was excited. I really mourned the fact that Flash was gone and the empowerment there, but this was kind of exciting. Then on top of that, there was a contract awarded to many publishers, but we were one of the publishers, to convert all our textbooks to digital for September. That was highly interactive 3D models, bringing to life videos, etc., science books, the whole range.

We have choices

[00:10:17] So we have choices. This is chapter one of three chapters of choices. Another book I recommend is Choice Theory, kind of riffing on the psychology and the therapy earlier. It's an incredibly dense book, but we have choices and how we react to things.

[00:10:35] I was talking to Connor at dinner last night about the fact that when we have a negative thought, we really have to counterbalance it with three or four positive thoughts. It can be a little forced at times, but our default, like the mice in the maze, is to be negative and fearful. But we have choices. Do we embrace the change and at least use our creative brains as engineers, product managers, designers to think of solutions and the opportunities, or do we go straight to fear? Absolute fear.

[00:11:04] As I said, different people react differently. Some folks were like, "This is incredible. I have a huge opportunity to pivot from print design," which I was part of leading with the wider leadership team across the world in that company, "to digital design." That was an amazing opportunity for those folks. Some folks not so happy about moving from Flash, but my God were they happier when they went to a world of Unity, particularly from the gaming perspective. And then the whole print model suddenly coming alive with interactive, etc.

[00:11:40] Some were a little like this guy. I'm dating or aging myself here a little, but if anyone remembers Scotty, it was, "She cannae take it, Captain." Scottish accent. But it's really what we can't do, how it won't work, how it's impossible. That's in every team. I had a tendency myself and I tried to do it less and less.

[00:12:01] Also at the same time, has anyone heard of this term? Let me describe it. I heard it at this time and I don't know, it's very popular at the time, design director, but I did say to the team, look, if we continue on this path, it was a tough meeting, I'll never forget it, we're in danger of becoming a team of designosaurs. So designosaurs see the comet coming and they don't do anything.

[00:12:27] Some kept designing in Flash outside of work. Some were still designing websites in Photoshop. Remember when that happened? That was a thing. And some were, as I mentioned earlier, really going straight over to the new world. So please, and in every profession, don't become a person who sees the comet coming, the writing on the wall, and does nothing.

[00:12:50] Again, that kind of positive... and this isn't, like, I genuinely mean this, this isn't like toxic positivity. As I said, a considerable amount of hair loss has come from me being fearful, from me stressing throughout these times. But now, as I move through my life and I'm a little bit more, I guess, change welcoming, I want to go back, as I said, and instead of "what's the worst that could happen," which is quite an Irish way of saying things, what's the worst that could happen, try and say, what's the best that could happen?

[00:13:21] In that case, I always wanted to get into UX. I was a digital design manager at the time. I left a director of UX. So I built a UX team there. People shifted from print design to being a UX team, and some stayed as amazing specialists in print design as well. And then Apple, and this isn't bragging, it's actually a shout out to an amazing company now, Emmet O'Neill[?] was my boss at the time, from StoryToys. Maybe some of the Irish folks know that company. But one of our first ever apps is in the Apple App Store Hall of Fame. Curious George was one of the properties in that company. So imagine, as a dad of kids under the age of six, I was so proud. It was kind of like a mission or a meaning-based moment for me.

Chapter two: Fleetmatics and the acquisition

[00:14:05] Time machine moment again. It'd be like a dissolve in the movies here. So let's do it. And you've got to love a cat meme as well. Time to move on. I was approached by a company in the area of telematics, and I was like, okay. Irish-based company, I'm a proud Irish person, proud European. They had also just floated on the New York Stock Exchange, a huge... Fleetmatics, they were called. They were a huge success story that people really didn't know about, but they were 400% oversubscribed in their IPO when they launched.

[00:14:39] So I thought, okay, this sounds incredibly exciting. But I saw an opportunity of change. This is what the product looked like when I turned up in the company. This isn't what it looked like when I left, in case anyone is about to leave the room. But it was on the mission really to build out a user-centricity UX team, and I'm hugely nostalgic because I was asked to UXDX at that moment to talk about my plans, etc. So huge nostalgia here as well.

[00:15:06] They were also Google Maps, one of the biggest enterprise users in the world at the time, and again many people didn't know about them. Hugely exciting, massive plans with the founder. And then this happened. Again, massive change, and to Tasha who spoke about acquisitions, this happened.

[00:15:26] I couldn't believe it. I'll take a step back. I got off a plane, or it wasn't a plane, sorry, I got off a ferry with my family camping in France on holidays, and I had four missed calls from my boss and the founder of the company, and there's no coverage for those hours on a ferry. I think it's still the same way. That's either a really good thing or a really bad thing. I just centered myself and I did whatever I could and I rang him back. It was, in my opinion, a really good thing.

[00:15:56] But as you saw in the talk about acquisitions and the change to design, the change to people, to leadership: who moved my CEO, who moved my boss, who moved my cheese? We were acquired for 2.4 billion. And one of our competitors, Telogis[?], on the other side of the world was acquired. And then I think Yahoo and AOL were bought at the same time. Same choice, same moment, of how we react.

[00:16:21] Some did fight the change. Some hemmed and hawed, if you remember the characters in the maze, wished it would go back, wished we could go back to the smaller office with the founder, etc. But one person reacted incredibly well, and that was really the founder. A little bit more on that in a moment, but that really affected the rest of the company, that leadership, that positivity, and that welcoming of change. It led to what I would now say is what is the best that could happen.

[00:16:50] I gave a talk ten years ago, nine years ago, I'm exagg... Irish people tend to exaggerate. Nine years ago at UXDX, excitedly saying I'm going to build a team of 25 people, and it was going to be the biggest UX team, I think it was at the time, in Dublin. Because of that acquisition it became 80 people on many continents, and I was incredibly proud.

[00:17:11] And then the wider team as well from telematics, with an innovation breakthrough from our data science team in Florence at the time, still rocking it, and I know some folks from Verizon Connect are here. They released, way before it was hot and cool, AI dash cams for predictive and preventative safety, etc. So a huge opportunity there. And then 5G launched with Verizon, which was a huge opportunity. By the time I left, this is the kind of products that were being released, the kind of UI and the kind of overall experience that was being released for our customers as well.

[00:17:50] So massively proud of what could be a seismic change of acquisition. People resign, people are frustrated, but because of what I would say is a culture of embracing change and really setting the tone, both myself, I'm proud to say, but I really had an incredible boss, that led to some of this technology as well in that company.

[00:18:14] So, the power of embracing change. I have a note here I'm actually going to read out, because it's from the heart. A shout out to the founder of that company, Peter Mitchell[?]. Founder, change agent and people person. He really embraced that change. I'd say up until the first thousand people in the company he founded, he knew their first name. He knew their family story. He knew their background. And he really cared for people. Still does. As a result, the change, the acquisition, the mergers, all of that were continuing to be massively successful. That is quite inspirational and has an effect on then leaders to model that same behavior.

Chapter three: Contentful and generative AI

[00:18:55] You might guess, in my third chapter of my trilogy, if I want to keep the cinema going: history doesn't repeat itself, but it often rhymes. And yes, let's flash forward. Let's go back to the future. Recent history. I joined Contentful two years ago. You might be guessing what's about to happen. I don't know why this keeps happening to me, but I joined Contentful, one month in, and then this happened. And that's what it felt like.

[00:19:26] Generative AI really landed in my first month, and then the huge impact of it and the strategic disruption and, in my case, huge excitement landed. But for some it felt like that eye turning into a dynamite stick and the robots are coming.

[00:19:42] But I have to ask folks, what do you think generative AI is generating? Shout out if you have the strongest opinion on what it's generating. A lot of... Yes, it's generating. You're all right. Whatever you're thinking, it's generating all of these things. Opportunity, innovation, fear, anxiety, stress. But one thing that it's definitely generating is content.

[00:20:18] And I literally sat there going, I cannot believe the timing of this. I've landed in a company called Contentful that is at the intersection now, potentially, of personalizing content through AI, at a time when we're having, for better or worse, and in my opinion doing the right things with visionaries and design leaders and engineering leaders and product managers that are doing the right thing. We have a huge opportunity. But literally, folks, what are the chances?

[00:20:47] Again, I kind of fell back to that book, Who Moved My Cheese? I thought, right, what are we going to do? It is stressful right now. That's stressful. There's certainly been reprioritization. Certainly was at the time. But we have choices. And I chose, and I hope I inspired the wider team, and I was certainly inspired by folks we work with at all levels, all groups, to embrace the change. And that's it. We can either choose fun, even in all the confusion, or we can choose fear. And fear is natural, but we have to do that. Can we check ourselves and do two or three counterings of it with a more positive attitude?

Concept cars and strategic north stars

[00:21:24] Now, another huge shout out. I don't know if folks are familiar with Jared Spool, but Jared Spool had an amazing series when I was in Fleetmatics Verizon Connect called Leaders of Awesomeness. If you don't know it, please sign up to it, as UX professionals, but everyone. It's really about the power of strategy. We really are visionaries. We can be very strategic as well. Get over your imposter syndrome. Within the area of UX, in the advent of AI, strategy, future thinking, future collaboration with humans is not going to be replaced.

[00:21:58] And he's a huge champion of concept cars. Look into the future two, three years out, maybe four years out. I love that stuff. I love to refresh it with the team every two, three years, but not burden them with it so it becomes like a full-time job. I can't show this whole video, but yes, in those first few months we knocked out a concept car video. And yes, it was classically agentic. But you know what it was? It was provocative.

[00:22:26] As I said, we're going to stop the video before it goes into too much detail. Yes, we're on the road to this in a different direction. Frankly, in a much more exciting way from the teams. But it was provocative. It was a conversation starter and it was directional. So when in doubt, when in confusion, please look at doing what I would describe as strategic directional north stars.

[00:22:47] Now, don't do it in a bubble. Please don't. And I hope, and I apologize to my team if I ever feel I'm distant from the team on some of these concepts, but actually the team were truly informing this. None of that distant kind of future-looking stuff is worth a hill of beans without the team actually delivering their own true vision, their own true strategy. So it's two-way between them and the tactical team-level concepts. That's where the magic happens. That's where the closest user research, customer contact and co-design, frankly, with our customers and our partners happens. And that's where we're at right at the moment.

What the team found in the design sprint

[00:23:25] Speaking of which, I'll just take you... Maybe next year there'll be a talk from the team, not from me. I shouldn't be talking about the work, but on where we are now. Right now, a huge shout out to the team who did, in those early days, a design sprint, and the classic $100 game, if you're familiar with it: if you had $100, where would you put it, on which feature? And there's a huge shopping list, of course. Those design sprints that we love. I know there was some negativity about design sprints yesterday, but I believe they're brilliant, or whatever the flavor, whatever it is.

[00:23:54] The really surprising results were, we want to see these somewhat small use cases rather than the big bang. But they have huge value to these marketing teams, these knowledge-based teams, these e-commerce teams, such as, please translate my content. We're right there now. We're launching it. It's launched. We're also looking at alt text for image generation, automated, that can be automated, and search engine, or GEO even, automation. So these were really valuable.

[00:24:26] And then the team took me aside and spoke to leadership and said, hey, relax, cool your jets, relax the cacks, as we say in Ireland, relax about the whole conversational, please. It's much more, the agentic is much more about actually the contextual helping on an AI level at the feature level for incremental improvements in productivity. That's what really matters to our customers, and eventually we'll get to the promised land.

[00:24:50] And then the team started to produce things that actually proved out in the testing that, on the left of our preview and our UI, that translation in on the field and the text level is so much more important and so much more trustable than on the right, "hey, translate all my content everywhere." We may get there, but right now we're going on the journey with them.

[00:25:13] So our response to change determines our fate. I think our fate is bright in our company. I hope it is in yours as well. Of course there's again that bumpy, lumpy journey stuff going on. But because of that, the attitude now is forming with our users, with our customers, and maturing of our strategy in sync with them. Yes, we'll be doing the concept cars further out, but we are now beginning to deliver and are planning things, of course, around automations, AI actions, looking at the scale and bulk for some of our huge customers. But we're doing them with them, getting to agentic, of course, but one step at a time, one day at a time.

[00:25:52] So, a cheesy summary for all of you, please: just enjoy this moment in your career. Don't look back like I have in some of my chapters going, I missed... It's a bit like parenthood, where you stressed as a young parent and you kind of want to go back and chill out. Do that with your career as well. This is your portfolio piece. I've had three or four of them. I'm lucky enough to be that long in the industry, and had some times where I was out of the industry as well.

[00:26:18] And I'll leave you with this last slide. It could be a great thought leader right now, but it's pretty universal. It's also a bit Yoda, to be honest. But whether you think you can or you think that you can't, you're right. So what you bring to that next meeting, or your next team meeting, or to your family dinner table: just please start to think about how you talk to yourself about it. And that's where the true fun and, dare I say, easiness of your day job, of your life, will start to really creep in. So thank you very much.

Q&A

[00:26:56] Host: Beautiful. Absolutely beautiful. I loved it. What a wonderful, wonderful, uplifting way to finish things. We have a few minutes for questions, and I'm impressed, because yesterday at this time we were more banter in the slides than we were questions. So this is good. Christian, actually, big shout out to Christian. Christian's asked some amazing questions across a few days and popped their name on everything. So thank you very much for that and for engaging us so well. With so many changes, why the roadmap? Is there any point in having a roadmap, or is tomorrow enough?

[00:27:29] Donal: Well, I won't speak on behalf of our CPO or the product management folks. But you need some level of plan. You need something. It is ultimately, at the end of the day, it is investment. There are budgets involved. But I do agree that roadmaps that are out beyond a couple of quarters, that are out into next year, that's bananas, okay?

[00:27:51] Donal: I really recommend that you're much more in the short-term planning of it. And again, back to the teams and the people influencing the triads. They should be influencing, which they do in the triads and quads, and research are heavily embedded as well, or assigned. That's where then the customer feedback shapes the near-term roadmap. I'm big on roadmaps. Again, maybe it's a little bit of scar tissue, but I've also worked in companies with no roadmaps. I don't recommend it.

[00:28:17] Host: And there's that element where obviously the backlog is what we need to do tomorrow, but the roadmap gives us, even if it's hazy, a direction. It doesn't matter if that direction shifts, we can always shift a road, and leadership need to be open to change from what the teams and the customers are saying. But it gives you that horizon to look at, that if it changes then it doesn't really matter. I love that.

[00:28:35] Host: Fab, I love this next question. Are there any recommendations you would give to define the line between a hype bubble, something that's really a disruptor, or is it just hindsight? Will we not know until afterwards?

[00:28:49] Donal: Watch the level of investment is what I would say. The frothiness of investment in AI concerns me, I have to say. Just on a personal level, I'm a bit weird. I did a business degree before I found out what I wanted to be. I think it was a rock-solid decision, to be honest. But then I found out I was a frustrated designer. But I do look at the markets. I do look at the financials. We have a superb CFO. I'm hugely interested in that.

[00:29:19] Donal: So when you watch the frothiness of investment, overinvested, and again Pamela from SumUp did a brilliant job at talking about the cycles. We might not like to hear it, but so many of our tech cycles are based on the market investment interest rate cycles as well. That's the only thing I can say, to predict when it's overly hot and frothy.

[00:29:37] Donal: My bubble detector or radar is high, because the first time I had money left in the bank after excitement, and I was a poor musician before that, was my first job in the dot-com, and then rapidly laid off three, as I said, three times in a row in two years, and it was really hard, really brutal. So I can smell a bubble a mile away. But there is truth and there is longevity to this, these two letters. It's for real, but it's a bit frothy as well.

[00:30:10] Host: That's brilliant. That's a lovely way of putting it. You're still standing with all the optimism. And thank you, whoever put the last comment on. We end with a little bit of banter. What kind of cheese did they move? If Gouda, that's okay. If cheddar, they should leave it and not touch it. I don't think we'll go into your cheese preferences, but if anyone wants to know what Donal's cheese preferences are, then he is around for some questions afterwards.

[00:30:29] Donal: Absolutely.

[00:30:29] Host: What a wonderful way to finish things today. Thank you so much. Wonderful.

[00:30:32] Donal: Thank you.