Host Intro (Gene Kim)

So our next speaker is John Cutler, currently Head of Product at Dotwork. In my opinion, for the last decade, he's been doing the most innovative work advancing the field of product design and how we can co-create outcomes with engineering and everyone around engineering.

In my opinion, he picks up where Alan Cooper, Marty Cagan, Jared Spool, and Heidi Helfand left off in terms of defining how to create great experiences for customers. And it's been my experience that his tweets and LinkedIn posts are some of the most widely shared among this community.

John believes that technology and design are the secret formulas for winning in the marketplace. And like me, he's an avid user of AI and is constantly building tools for himself on both personal and work projects. So I'm so delighted that he's going to share how AI is not just impacting engineering, but beyond the product organization and beyond. So here is John.

John Cutler

Thank you. How's it going?

This talk is called Alice's Adventures in AI-Land. And I'm just going to preface this by saying I'm not representing my company. I probably talked to folks in your company, so this will be the advantage of this talk, because I can talk about anything I want.

So it's 1865, and telegraph cables are spanning continents. You have steam power powering the Industrial Revolution. You have photography. You have Boole with Boolean algebra. You have Galton with correlation and regression. You have Maxwell with electromagnetism. And there's a lot of excitement about technology, but also a lot of fear about technology, and justified fear. There are dehumanizing conditions in factories, child labor, pollution, overcrowding, and it is a challenging time.

And in that context, Charles Lutwidge Dodgson, the pen name Lewis Carroll, pens a book for children and writes a children's story. He is a mathematician, a magician, and actually an Anglican deacon, which I didn't know about before. And when I was looking for metaphors to think of capturing this time, and that's really the goal of this talk, is capturing this moment so we can reflect on it, I couldn't think of a better metaphor. So stick with me on this.

Alice is all of us, right? Tumbling into this strange world, thrilled, bewildered, super big with the Eat Me cake, and very, very small with a Drink Me bottle; at one point completely empowered and then completely humbled and powerless. And the rules of the game seem to change in mid-conversation.

Now, I think that the White Rabbit is best described as the hype cycle, rushing ahead, always one step ahead, chaotic, pushing us to do things maybe we aren't completely proud of. And something's always out of reach.

And the Cheshire Cat is probably AI. The Cheshire Cat leaves behind that enigmatic smile, which is when you're in the zone and then you ask, what the hell am I doing here? And it just smiles back. And it's that disembodied grin with riddles, appears and vanishes, that best describes what people are attempting to get answers out of it too.

And then the Queen of Hearts is the corporate machinations at the moment, playing croquet with live flamingos and hedgehogs, violent, authoritative, at times dominant, very, very impatient. It's the corporate machinations: off with their heads. It's a very, very tough time and a very great time at the same time.

And the Mad Hatter's Tea Party, I think, is an event like this. It's the discourse. It's both structured and disordered. One of the funny things about the Mad Hatter's Tea Party is that they never stop, so the tea cups never get cleaned. It just keeps going. We all have our own rules. We all have our own language around AI. There's a number of contradictions.

The Jabberwocky is all the really terrible, terrible things. The Jabberwocky is this poem within Through the Looking-Glass, but let's just go with it for a second, and this looming fear of where this could all go, which is a justified fear.

And the Caterpillar, I think, is what my talk is today, which is the question, who are you? The Caterpillar asks that, and Alice says, I hardly know, sir, just at present; at least I know who I was when I woke up this morning at the Fontainebleau or flew in at Vegas International, is it called? But I think I've been changed several times today. And so it can feel very bewildering.

So I would say: how do you know I'm mad? You must be, or you wouldn't have come here to Las Vegas to the Fontainebleau. Yeah, I mean, it is kind of a mad place to think about it.

So the goal for this talk is to normalize not knowing. There's a lot at play here: our identities, our jobs. There's a sense of disorientation mixed with curiosity, euphoria, subterfuge, illusion, fear, and any effort to have all the answers and any pressure to have all the answers at the moment will fail.

And one of the goals in my talk today is to share a little bit about my story, about how I use this technology, but also to share with you vignettes, perhaps from your companies. I probably speak to people at many of your companies who are experiencing this moment in very different ways. And that's very important in this situation because we can feel our reality closing in, in this moment. But it is important to see how other people are experiencing it.

And then finally, Alice had to navigate the chaos on her own terms. I think she would ask the cat, what should I do? And we probably end with the quote: well, I don't know, where do you want to go? So there's a lot of introspection that has to happen here.

So I'm going to start with my AI usage, just very, very practical here. I have one monitor. I'm a product manager. I'm a head of product at a company, at a startup. I have one monitor with Cursor, one monitor with ChatGPT, and then my third monitor where I attempt to work that has Slack on it. I spend a lot of time making digital twins of organizations. If you want to drop by the Dotwork booth, I'll tell you all why I'm doing that. I love the little thing, the whoops down there. You can see I got a little out of hand that day: 20 bucks, 20 bucks, 20 bucks, 20 bucks, 20 bucks. It all sort of adds up when you're in the zone.

I do a lot of prototyping. I'll walk through an example of that in a second. I write marketing copy for our company. It's small. And I still write a lot of handwritten notes, but I use AI a lot to organize Cursor projects with a lot of my collected knowledge so I can repurpose that in different ways. And I would say, talking to a lot of product managers, that's fairly typical: a mix of prototyping, creating synthetic data, writing, and organizing notes is a pretty standard product workflow at the moment.

This was my partner Sharon caught this picture. I also walk a ton. I've gotten more steps in in the last year than the... well, now I have a kid, so the steps are hard, right? But this is me. I'm walking, I'm talking, and there's a joke in my company that when you see my brow furrowed, maybe John's got to go for a walk, which basically means that I have to go walk around the block, duke it out. I ask this sort of red-teaming thing, pre-mortems with AI. I walk through scenarios, and then I come back and I write a document. And that's also part of my workflow.

So the quote is: why, sometimes I've believed as many as six impossible things before breakfast. And I think this is one of the seductions of AI, is you have these moments where things come together and then you have to walk yourself back.

So one of those moments for me, just to give you the backstory here: we're a startup, and we had this massive company courting us. They'd given us this RFI, which was generated by ChatGPT. You could tell: all the colons, all the em dashes. It was completely comprehensive. When you get an RFI now, just know that it is created by ChatGPT, and they basically will make it everything, everything.

So we get this thing, and we make the number one mistake in product, which is to do exactly what the customer says. We go through and one by one we demonstrate, we give them a demo of how our product is going to do all the things in the RFI. And a couple weeks later, customers always give you gifts. In this case, the prospect pulls us aside for a meeting. They say, we're having a really hard time demoing the product, not because of your product, but because it's just loaded up with all this stuff. To which we didn't say, but you asked for it.

We took the feedback very deeply and we thought, what do we need to do about it? Let's put our product thinking hat on. And so this was basically the workflow over the weekend. We did a little bit of co-design with the customer in Miro, and then I built up a lot of chops for generating synthetic data. It's a super valuable skill for product management because it helps you work with engineering. I'm not going to do designers' jobs. We have designers who can be great designers, but I can generate business logic and data well.

And so we used that to make 18 prototypes built on top of our platform, which is the good part of this story, and walked into a meeting with them on Monday. We hadn't done any real custom development, but we had reimagined our product, built on our platform with components that actually solved the problems that they had. And they hadn't seen anything like that. This is a SaaS product that turned around three days later with a complete bespoke version of their product that worked. And that was one of those amazing moments.

But things aren't always that amazing. The FOMO is real and the pressure is real. As someone who prides myself on systems thinking and connecting the dots or synthesizing and sensemaking, I'm going to be honest that sometimes I walk into work and think: are any of these skills going to be worth it in this new reality? And then I think, well, maybe they're going to be very valuable in this reality. And I think, well, maybe they're not going to be very valuable in this reality.

The profound fear of my professional future: there's a lot of FOMO to move faster and faster and be ahead of the game, not to miss out. Do I sleep eight hours or do I vibe code for three hours and then sleep for five hours? Do I wear my skeptic hat or optimist's hat on any given day? And then I am a parent and a citizen and a community member. I worry for my son, I worry for my community, and I worry for people I respect professionally who have, in a sense, been gaslit in the current climate and who are having trouble with their careers, having trouble finding jobs. So I wanted to capture what it feels like from one person's perspective.

So let's go into the vignettes now. Hopefully what I want you to do with each one of these is to think about the good, the bad, and maybe what you could take from it or how you could connect to someone in your organization who might be going through these.

The quote: no, no, the adventures first; explanations take such a dreadful time. No, let's go.

This is a story about a UX researcher, the undervalued expert. So Talia is an expert in linguistics, has a background in linguistics, applied research, ethnographic research, a background also in anthropology. Literally one of the smartest people I know. They were drawn to tech because of this interplay of human factors, technology, people. This is exactly the kind of person you want on your team right now to navigate the current landscape.

And they were laid off a month ago because they had a product leader who kept standing up and saying, we can replace research with AI. Now, Talia knew this was wrong because it actually broke every precept of applied research and the science behind what was happening. But they were continually told that this is no longer valid anymore.

So you might want to say, can you make an intro to this person? We want to hire this person. You can't, because they've left tech. They've just gotten sick of it, and they're out. All my other stories have a good and bad side, but this is the one which is really hard at the moment, is that people feel very undervalued in this environment. And people are not picking up on the true systems thinkers and experts in their environments who can help them navigate this situation. Linguistics, ethnography, human factors: these are all the things that you need at the moment to be successful.

At any rate, I'll never go there again, said Alice; it's the stupidest tea party I ever was at in my life.

This is a story about the engineering director turned builder. Are they in the zone? Are they seeking solace? Or both? So in this case, we had a director of engineering smack dab in the middle of the organization, two decades of experience as an IC and a manager. And this is the type of manager that wanted to be the manager you would love to have and brought team members between companies to follow them.

But they started to wonder, as management became more and more of a pressure cooker in this organization, in the current climate, whether there was any future, if they could ever achieve that long-term goal they had had as a manager in their organization.

So they started to notice a change in themself. They started to do AI projects on the weekend, and they started to feel joy. I just remember talking to Gene about it. There's this sense of joy and curiosity, and you feel like you're in the zone. And this person felt like they were in the zone for the first time in years in this environment. In fact, their partner was so worried about them because they hadn't come out of their room and was sleeping a minimal number of hours: are you okay? And he's like, I'm having the most fun of my life right now.

And then it clicked that they didn't want to be part of management anymore, that that felt like that was not the place for them. And they surfed a couple of layoffs in their company to get closer and closer to the work and bringing that experience to the work. And they thought to themself: I'm having fun. I want a safe job. I want to serve my family. And maybe it's time that I focus on this. I'm having fun for a change, and maybe there's a silver lining in this and maybe we're going to turn a corner as an organization. I find that very interesting.

What's the use of a book without pictures or conversation?

This is a fun story. I don't know if any of your teams sent people to this event. It was great. There's an event in Europe called DDD, Domain-Driven Design Europe. It's a wonderful event. A lot of architects go to this.

What I loved about this event is that you took all of these architects and you took them out of their companies into a conference, and hopefully you're feeling like this in the event today. And the quote was: this is the first time in a couple months I can have real talk about AI. Because in my current company, there's a little bit of a purity test, a positivity test when it comes to how AI is working.

And what impressed me is these, again, just like that UX researcher, these are the folks you want around. They think about domains, they think about architecture, and they were incredibly curious about the potential of AI and were doing lots of amazing projects in their company and talking about them. They just didn't feel quite safe enough to be mentioning any skepticism currently in their companies.

And again, the lesson here is: can you foster an environment where people can have those conversations in your company? Or I would recommend take advantage of this situation where you have folks that you can have conversations outside of your company to have real talk about how AI is helpful in your company.

What a curious feeling. I must be shutting up like a telescope. And then, delighted, her face brightened up at the thought that she was now the right size for going through the little door into that lovely garden.

So Sarah is living her absolute best life at the moment. Background: had worked on machine learning teams before and then also had the pleasure of working on chat interfaces. So if you've worked in machine learning and chat interfaces and you're currently working in a company as a product manager, this is a very, very good thing.

And as there were successive layoffs in the company and pressure to AI all the things, Sarah was picked out because of her keen ability to navigate the organization and get things done and move things forward. And she was tasked with leading a key AI initiative in the company.

Now she remarked that it was a good thing because her counterparts and other product managers were still having to sweep up the mess of the last couple years of hypergrowth. But Sarah was having the time of her life. She got what she wanted when she needed it. If there is a tool she needed, fast-tracked through procurement and legal. If there was a meeting she needed, suddenly the meeting happened. If she needed to talk to someone, talking to someone. She was invited to the C-suite offsite to talk about AI. This is amazing stuff.

But again, with each of these stories, there's a little bit of a hard part. So one thing that Sarah asked me to communicate is that she has fellow coworkers who are afraid to even take parental leave in this environment, that are even delaying family plans in this particular environment because of the pressure cooker in their company. She said she's very privileged to be doing what she's doing, but wanted to make note of that.

I don't think they play at all fairly. And they don't seem to have any rules in particular; at least, if there are, nobody attends to them. I don't know if you don't take this too personally if you're in a bank at the moment.

So VP at the bank, the quote is: the last couple years have felt like a whole career. The worlds of private equity and consultancy are filtering down into the playbook. It's either internalize that or not be around: managed by ratios, short tenure, maximize short term, and squeeze value. No time for continuous improvement in this environment. It's only big swings. That's what you're supposed to do.

And this person felt that this was four to five years of careful continuous improvement in building and transforming that organization that felt was under pressure at the moment. And this is just the reality. I'm just relaying the reality in different organizations.

It would be so nice if something made sense for a change. I'll end with a good story, right? This is an adaptive ops team at a company. They're a three-person team. And for them, their company had -- I loved one of the prior talks, as someone was just talking about a culture of continuous improvement, a culture of thriftiness, a culture of not over-hiring on the team, of experimenting with new tools.

And for them, this feels like a playground for disciplined operational excellence: scanning the organization. Where is there friction? Where is there transactional work that is being treated as collaborative? Where can we use AI to supercharge and help our teams?

Very specific example: product managers were filling out almost 20 forms for anything that had to be released. One for customer success, one for the VPs, one for product marketing. Product marketing had multiple forms for the enterprise, SMB, all the segments. And now with the press of the button, AI rewrites the release notes for product marketing into the different voices of the different customers. They get a Slack. It says the release notes are done. Go in, edit it, approve, deploy. Press a button in Slack, deployed.

I love that story. I think it's amazing. Their comment when I was interviewing them was that if it hadn't been for their founders and other folks who were thrifty from the start, who had this culture pre-AI -- this is just like the story we just heard from a Toyota context -- if you had that culture pre-AI, you can bring that same mindset into what's happening now and it can be transformative.

So we'll end with: who are you, said the Caterpillar. I hardly know at the present; at least I know who I was in the morning. But then I think there might have changed several times since then. And this is the sensation I think a lot of people are going through. And I feel that there's an element of embracing the not knowing at the moment as a way to move through this particular time. And I think that's kind of a timeless lesson in Alice in Wonderland.

So to review: normalize not knowing. Anyone who says they're an expert in this -- there might be 5% of anyone talking about this who has been doing this for more than five years. Think of it that way. So the person who's an expert is just as curious and as excited as you. They might have gotten started two years earlier or three years earlier. Most people haven't been doing this for 10 years. I'm sure there are people who have been doing this for 10 years.

The next is that people are experiencing this in vastly different ways at the moment in your companies. Be conscious of when there is this kind of positivity purity test in the environment. Can you reach out to the people who have productive forms of skepticism? Can you harness the people who aren't necessarily going to rah, rah, rah all the things? Can you continue to foster a culture of continuous improvement?

And then finally, there is no map. That's why you're here. Hopefully you're having a good time. And then we can roll off into the cocktail hour.

Which way should you go? That depends a good deal on where you want to get to. Thank you so much.