In short
Cal Thompson (VP Design at Headspace) discusses how AI changes product design strategy, measurement, prototyping, and research—while arguing that designers’ core value (empathy, discernment, accountability, and human intuition) remains essential. He also covers why Headspace hires interns and how design culture/rituals protect creativity.
Guest backgrounds
Cal Thompson leads Headspace design for six years. Previously worked at Fjord (service design and innovation consulting) within a global design community (1100 designers, 29 studios), emphasizing research, empathy, and continuous learning. Rachel (Headspace senior product designer) previously worked at Calendly and other UX/product roles; she experiments with AI tools and treats AI as a “thought collaborator/intern.”
Key claims
AI strengthens designers’ strategic power by enabling faster market/competitor analysis and text synthesis (e.g., NPS/app-store feedback themes). But avoid “AI slop”: don’t replace firsthand observation, and don’t outsource accountability for quality. Culture and rituals (tea time, mindful breaks, “show and tell,” silly WIP meetings) build trust so designers collaborate and make better decisions.
Notable examples
A 2020 Headspace user interview (“a boyfriend who would never let me down… then ditched me”) drove a major strategy project leading to the Ginger merger. Headspace uses AI-assisted synthesis of written user feedback, but designers still re-read raw inputs to catch nuance.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOMeet Cal Thompson
0:45 to 3:18
Discussion on Cal's background and the importance of empathy in design.
“I feel like I don't need to say anything now.”
The Evolving Role of Designers
3:18 to 5:48
Cal shares insights on how AI tools are changing the role of designers.
“Designers as a profession and creatives as a species, we are not going away.”
Empowerment Through AI
5:48 to 7:40
How designers can leverage AI for better decision-making and business case presentations.
“Could this grow revenue, et cetera, if you're working in a business?”
Navigating AI in Design
7:40 to 9:16
Cal discusses the balance between creativity and data-driven decisions in design.
“So instead of going back and forth and hearing noise from other people who say like, well, there's no business case for this, there is no business case for that.”
AI Tools in the Design Process
9:16 to 10:12
Exploration of tools like Figma Make and their use in guiding design roadmaps.
“And actually, I would love to go through a bit of this process together with you to understand where AI is the most helpful versus where AI potentially is very unhelpful.”
Measuring Product Success
10:12 to 14:00
Using AI tools for synthesizing user feedback and improving design.
“So let's start with the first kind of part.”
The Importance of Human Observation in Design
14:00 to 18:23
Learn why direct human observation is crucial for effective design and problem-solving.
“But now I get this, you know, big couple of boiled up themes.”
Synthesis and AI in Design
18:23 to 23:27
Understand the balance between AI synthesis and retaining a designer's perspective.
“synthesize them and kind of themes that people are interested in.”
Prototyping and Collaborative Design
23:27 to 28:00
Discover how collaborative prototyping tools enhance team creativity and problem-solving.
“We don't want to just create for the sake of making, making, making, making.”
AI Tools in Design
28:00 to 29:20
Discussion on how AI tools like Google Deep Research and ChatGPT enhance design.
“these huge clickable prototypes, you know, and now you can do like a coded prototype in a few minutes, which is incredible.”
Show all 29 chapters
The Importance of Design Culture
29:20 to 36:40
Exploration of design culture and its vital role in fostering creativity within teams.
“What is the best design culture for team's creativity?”
Creating Collaborative Environments
36:40 to 42:01
How rituals and structures can enhance collaboration and trust among designers.
“design is a process that is nourished by inspiration.”
The Role of Designers in AI Integration
42:01 to 46:30
Explore how designers should use tools and intuition to make informed decisions.
“I mean, we were learning about computer vision.”
Introducing Rachel: An AI Expert at Headspace
46:31 to 47:59
Meet Rachel, a senior product designer at Headspace with expertise in using AI tools.
“And this is why we wanted to bring Rachel to talk a little bit more about nuanced things that where AI can be helpful and unhelpful.”
Optimizing Design Processes with AI
48:00 to 51:04
Learn how Rachel uses AI to enhance her design workflow and efficiency.
“And there was a mentor who once told me where I was telling them where I wanted to become much more technical as a designer.”
Impact of AI on Design Decisions
51:05 to 56:00
Discover a case study illustrating how AI influenced design decisions at Headspace.
“I think the other half of using it is, for example, I had to synthesize some survey results and then do user interviews for them for a for understanding kind of like why members are starting to drop off therapy.”
The Role of AI in Design Process
56:00 to 57:50
Exploration of how generative AI influences design decisions and processes.
“would not have thought of that the generative AI tool put into that prototype.”
Human-Centric AI Collaboration in Design
57:50 to 59:50
Discussion on balancing human creativity and AI assistance in design.
“And so I, you know, for now, so I think I'm still trying to figure out how I want to let, if I want to let AI be a bigger driver in that, or if I'm still viewing it as the kind of expander, if that makes sense.”
Supporting Junior Designers in an AI World
59:50 to 1:03:36
Importance of mentoring junior designers while integrating AI tools.
“little deep dive into reasoning with ai and thinking where it fits we're now going to a q a part of our conversation.”
Evolving Design Roles and Education
1:03:36 to 1:06:56
How technology shifts the roles of designers and the importance of education.
“So we can't just, you know, I think, you know, Rachel, when you were talking about intern, it's a little different.”
Historical Perspectives on Technology and Art
1:06:56 to 1:10:01
Comparing AI's impact on design with historical art movements and industry shifts.
“And so it was that they were strategically targeting those specific weaving mills that were causing that.”
The Organic Nature of Artistic Movements
1:10:01 to 1:11:41
Explore how creative movements emerge organically through collaboration.
“And, you know, the kind of general consensus, which I will share is like our minds want to forecast what that's going to be, but we actually don't know until we get together as creatives and do it ourselves.”
The Role of Collaboration in Design
1:11:45 to 1:14:20
Discuss the importance of collaboration over solo work in design.
“We actually had in our previous podcast episode, we had Charles Vigas who was talking about how AI right now is very much an ego driven solo person tool of like, I can do multiple things.”
Navigating the Challenges of AI in Design
1:14:22 to 1:16:46
Understand the challenges of using AI tools and the need for diverse perspectives.
“You know, or someone on a team who comes from a different background and they say, I don't, this doesn't, you know, we're not solving this certain problem with this.”
Embracing Uncertainty for Creativity
1:16:46 to 1:22:17
Learn how to cultivate resilience and mindfulness in the face of uncertainty.
“And I think when I was inspecting the reasons behind that, I was talking to one of my mentors and she gave me this quote.”
The Need for Empathy in Today's World
1:22:18 to 1:24:00
Discuss the importance of empathy and compassion in human interactions.
“So that's a really, really good question.”
The Importance of Humanity and Connection
1:24:00 to 1:25:00
Explore the need for empathy, kindness, and collaboration in design.
“is just a little more of that listening in the world.”
Collaboration with Future London Academy
1:25:00 to 1:25:48
Learn about the collaborative efforts in product design and education.
“Follow you, find you, recommend you anything, any ask that you have.”
Engaging with the Audience
1:25:48 to 1:26:25
Discover how listeners can engage and share insights from the podcast.
“And as always, if you find anything insightful, useful, helpful, please share it because we love hearing your insights.”
Transcript
Automatic transcript. May contain errors.0:00Hello everyone, my name is Ekaterina. I'm co-founder of Future London Academy and today we are continuing our incredible conversations about AI, leadership, design, where do we all fit as creatives in this fast changing world of technology, artificial intelligence, where do our human skills go and how does our profession change as these tools evolve. and I'm very excited that today we have a very special guest who probably is the perfect guest for this conversation because they sit in the intersection of humanity and technology. We have amazing, wonderful, fantastic, fascinating Cal Thompson who has been leading Headspace as VP of design for the past six years and for those of you who don't know Headspace it is the the app the number one app for meditation all sorts of things to help your mental health and there are many more new functionalities that Cal has been working on with their team in the past few years so very very exciting space and obviously Cal has been working not just in the world of technology but previously they worked at Fjord which is a service design and innovation consulting so very much rooted in research understanding humans and empathy so I feel like today conversations will be very much rooted in humanity and empathy and all these skills as us creatives and designers are so good at but trying to understand where do these skills fit in the world of AI driven process AI tools the pressure from the world that there is on the value of creativity.
1:55So thank you, Carl, for joining. How are you doing? I'm good. That was an amazing introduction. I feel like I don't need to say anything now. I'm good. We can, you know, but yeah, I'm so happy to be here. You know, maybe one thing fun to add is that, you know, when I worked at Fjord, Fjord was a global design design community. We had 1100 designers around the world, 29 studios. And I think, you know, the reason that I, when, when I was approached by Future London Academy to write this course, the reason I was so excited about it is I think the global design community is a really powerful force.
2:30And when we come together and we learn and we decide what we as designers want to bring to the world, we're incredibly powerful. Like it's a very, it's a positive force on the world because it's a lot of people who are saying, I want to make things and I want to make things that are helpful. And so, you know, and I felt that at Fjord and I felt that at Headspace. And so it's really fun to be here today with you all and talk about like, what can we do as designers with all of the new tools that are available to us to continue being helpful, empathetic, you know, problem solvers, not just kind of, you know, beautification assistants.
3:06How can we be the transformative and thoughtful problem solvers that we all like being. This is a great start of a conversation because this was literally my first question. I suppose good news is design is not going away. Designers as a profession and creatives as a species, we are not going away. So would love to hear a little bit more of your reflection on what changed in the role of a designer, a design leader based on your experience at Headspace, incredibly large team with lots of complex processes, with lots of stakeholders. So where do you feel like your role has changed? And what has stayed the same as a designer?
3:52What's core to our profession? Yeah, I love that question. I think, you know, and maybe you all are feeling this, I think some Some of the strategic powers of design are able to actually get stronger in this moment where we have more AI tools available to us. Whereas before, and I just remember these days at Fjord and it was a little different at Headspace, but before we had to get a business analyst on our projects to kind of validate the business case for something or do the exploratory market research to figure out like is there a market need here? Is there, you know, are there sort of numbers and, you know, what's the addressable market?
4:30What's the TAM of this particular thing that we're trying to build a, you know, a feature for or a full app or a full service for? So we had to like find, you know, a lot of time to do that and to really like carve out, you know, how, how valuable could this, this thing be, or like how many people could this help? Whereas now you could use Google deep research or, you know, different forms of ChatGPT or Claude and really get into like, you know, through these, through these like deeper research and analysis tools, get some of that right away. So for us as designers, it's not so much about just the making, you know, which is the perennial challenge that we deal with of, you know, sort of, are you told what to make or do you tell the business and the service what needs making, you know?
5:16And so if you, if you are able to use these tools, these analysis tools, like pretty early on in projects to say like, hey, yeah, there is actually a market need or, hey, you know, we're seeing that competitors are doing this thing. So we wanted to, you know, analyze like which competitors are doing it. How are they doing it? How many users do they have? You know, how many, you know, what are their, what is their revenue? That's now data that is available to us as designers and design leaders that previously was much harder to access. I mean, you had to have these, like, I don't know if any of you all remember this, like, we had these weird subscriptions to, like, all these research and analysis tools, and now it's, you know, incredibly available on a day-to-day level.
5:59So then for you as a designer, design leader, if you're saying, hey, I see an opportunity based on our user research to do this thing, and I think we could make this feature or this service or this product, this solution, you see that and you can much more quickly find the opportunity size of that, you know, and have in doing so essentially help those colleagues on your team, the product managers, the engineering leaders, who are also seeking that same kind of analysis and also have that same question of, is this going to be valuable? Could this really help people? Could this grow revenue, et cetera, if you're working in a business?
6:41And so it's really powerful, actually. Like we're actually at a moment where these tools are giving designers tools that they previously didn't have access to. So it's a very long answer to your question, but that's what I'm noticing so far. This is a very empowering answer. And I love that you mentioned all the things that AI tools enable is actually the things that design is never necessarily like to do or the business stuff, the numbers stuff. And now you actually don't need to have this complex systems to figure out what is your time. So you can actually ask Chagipiti, Claude or whatever is the tool of your choice.
7:18And then you are more convincing as a designer. you are more, you have a better case for what you want to do when you present something to senior leadership, and you can make better decisions yourself, because again, we all sometimes too rooted in user needs and lose the context of bigger picture. So instead of going back and forth and hearing noise from other people who say like, well, there's no business case for this, there is no business case for that. As you said, we can do our user research, we can identify pain points and user needs but then we can go to the business tools and actually see if there is a business case for it is there enough audience for it is there enough money for it is there enough market for it and use the language that those tools will give us to pitch it back to the senior leadership so this is really good to hear that it's literally makes our life better and easier and I agree I think empathy and and research and everything else, I think very much stays the same.
8:21It was actually interesting that you mentioned that you used to use kind of business consultants and business designers and other kind of people as part of this process. It's actually a big conversation in the industry right now about the role of consultancies and big consultancies that used to be holders of this very unique information that otherwise you wouldn't be able to get. and now the biggest holders of I suppose power are the creatives because information is in abundance you can get it very easily but imagination and breakthrough ideas that's what still very rare and understanding that and coming up with that is what creatives and designers are very uniquely placed to do so in that sense again good news for all of us I suppose from everything you've been doing with AI, you've been working on the process of implementing it.
9:16And actually, I would love to go through a bit of this process together with you to understand where AI is the most helpful versus where AI potentially is very unhelpful. And I even have a slide to share. So I actually did not mention that Cal is the curator of our product design strategy course. So So this is, we've been learning from Cal for many, many, many years now and really excited that the knowledge and wisdom about product design strategy has been shared with our wider community so more designers can be empowered to actually contribute to roadmaps, actually make strategic decisions. But recently we did an update on the course with where does AI sit within the design process.
10:06So I would like to go through this as an easy way to discuss where is it helpful or not. So let's start with the first kind of part. We talked about kind of guiding on the roadmap. And can you tell us about the Figma Make, Clutch, GPT, why do you use them? How do they work there? So if you think of the design process, you know, as a flow, looking at this left to right, When you think about guiding the roadmap and actually deciding as an organization, what are you going to do? Like, what are you going to make? This is an area where you can use tools like Figma Make, you know, Claude has some UI design tools, ChatGPT, basically to start to identify sort of like, I would consider this more like areas that are in other products that are not being well.
11:02you know, that you're not competing with well within your product or areas of kind of unmet general need. And then, and, and really, you know, Chachi Petit is more for that. Claude and, and Claude can give you a little bit of that. Figma Make is really for like creating some prototypes and sharing those around. When you are working on roadmapping, just to get really, really crystal clear and specific, when you're working on roadmapping, sometimes it's too hard for people to actually envision what you're proposing as a designer, as a design leader. You know, a lot of us who are used to making things, we can see things in our heads.
11:39So when we say, oh, I think we need a feature that, you know, allows community members to talk to each other within our app, we're immediately imagining chat bubbles and emoji reactions and, you know, all this fun stuff. And that's all in our head and nobody else can really see that. And what I've done in the past is sketched those things out on little concept cards and put those into the roadmapping process so there's a little bit of a visual. But to be honest, that takes quite a lot of time, and it's not necessarily the most creative or generative or exciting work. So that's where tools like Figma Make can be really useful.
12:15Or Miro has any generative UI tool. Now there's a million. And so I could literally like give you a list of 20 tools here. In fact, we talked about this, but, you know, things that allow you to envision it so that your, you know, colleagues at work, product managers, engineers, data scientists, other folks, they can really see what you're talking about. You know, this sort of high level of like, this is, you know, think of it more like a thumbnail sketch, but they can really see it. They can track with you. You can help move the organization forward towards some of that vision. Measuring your product, just moving over to this little block of chapter two, measuring your product, the part where it's really helpful to use synthesis tools like the AI tools that are in Miro and that are in Figma, like anything that can do text-based synthesis, is if you have any sort of, and I'm sorry for those of you who might not have access to this data, But if you do have access to data from the users of your product or service that is written feedback, let's say App Store reviews, a Headspace, we have an in-app NPS survey, Net Promoter Score survey that has like an open -end question.
13:30I don't know if you all have things like that in your products, but essentially we get written language back from our users. If you have any access to anything like that, you can use either internal AI tools that are already approved by your company, you know, so they're safe and your, you know, InfoSec people have already said, yes, you can use this. Or you can use Miro and Figma, their text-based synthesis tools. Like in FigJam, there's a really great text synthesis tool. you can put in that written feedback from users and then get summary of that and see core themes from that. So these really are areas where you can start to see, oh, okay, like we have an issue, we're seeing this theme in our app store reviews that I wouldn't have as a human been able to synthesize very quickly from just reading them.
14:23But now I get this, you know, big couple of boiled up themes. Now I, as a design leader and a designer, I need to be thinking about how could I solve for those? Like if everyone is saying, Hey, we need more guidance in your product, you know, what are ways that we can solve for that in the, you know, in the user experience? Um, so that's that we're going to kind of like, you know, track through these. I want to pay special attention to chapter three anchor in human stories. And I see you, Katerina smiling and laughing. This is one where I said, avoid AI. And my friends at dscout are going to kill me for saying this because they actually do have some really lovely AI design research features within dscout great user research tool but there is really something powerful about in the field direct human observation and you know I don't know how many of you have gotten the privilege of getting to do like in home interviews or ride-alongs or you know shadowing sessions where you're watching someone work and you're really seeing what the pain points are and what they're doing.
15:23But I have found every design team that I've worked on, we remember those moments more than anything else because they're so direct, they're so human, they're palpable. We remember those interviews. I still remember quotes that users said to me in 2013 in home interviews. That is wild. You know, that to me, the reason that that's really, really important and why I wouldn't outsource any of that to AI tools who can kind of promise like cheap, quick online research is that you get something emotional from hearing that pain point from a person or observing it. You know, if you're observing someone's workflow or you're observing someone's day-to-day life, you get something emotional that is like kind of becomes embedded in you as a designer.
16:12And for those of you who like making tools and solving problems, you want to fix it. You know, it's like seeing someone who has a shoelace untied. You're like, Oh, I just, I don't know if you all have that sensation, but I'm like, I just, your shoelace is untied. Like you want to help. And, and that's really what that does. Um, and, and I, I will say just out of fairness to like our friends at dScout and user testing and user insights, all these online tools, you can get that same emotional visceral memory response from online research as well. You don't have to be in someone's home. But just meaning you as the designer and the maker and the leader really will benefit so much from seeing it firsthand.
16:52So we had, I'll give you a really great specific example. We had a user interview in 2020 with a Headspace user where he said, you know, I feel like this part of the app is this boyfriend who said he would never let me down. And then just when the going got tough, he ditched me. And I just remember Jonathan DeFavre and I, who were running that particular research project, we just never forgot that quote. It made it onto slides that senior, like our CEO saw. We just couldn't get that out of our heads. And that literally led to us doing this huge strategy project that led to the merger with Ginger.
17:35I mean, it was such an impactful, that one interview was so exemplary of all these other things we were hearing, but it was so memorable because it was just us directly talking to this person. I also was just reflecting on a few things that you were saying there and that synthesizing things was a pain. Again, designers never dreamt about doing it. So suddenly when tools enabled us to synthesize things in a faster way, that became such a relief. I can give my personal example of preparing for these interviews. We have hundreds of questions that people submit for each podcast that we record. And it has been a special fun for our team to go through all the questions.
18:18And you read a lot of interesting questions, but it will take a lot of time to kind of synthesize them and kind of themes that people are interested in. Obviously with AI, that takes seconds. Now, what I have to say, I love still going back to the original questions and still spot reading some of them. There is some something special about not trusting what AI synthesized for you as main themes, because some nuance can be kind of misinterpreted. And I kind of have this round circle of looking at the syntheses and then going back to the actual questions and reading them and kind of seeing if there is something more that we can actually chat that maybe is not as obvious and it's just generic.
19:02Yeah, I really, I love that. Yeah, well, it's like, it's sort of the sense of maintaining your own point of view still. And it's kind of like when you have a document you're making and it goes through rounds of edits, like, and you have a friend read it, or you have an editor read it or, you know, it's a similar thing. I feel like it's sort of getting to speed up that process, but you still do need to kind of go back and look at some of those and and get that direct inspiration. I also hear it in a user's voice, you know, or in your case, in the questions. But like, you know, when I've read individual NPS feedback, we have a Slack channel at Headspace that has like the NPS feedback.
19:38When I've read those individual ones, you can, you know, from people's misspellings or their ways of talking, you just get a sense of their humanity and then it becomes clear that you're not making a thing in a vacuum you're making a thing that other humans are using you know and it's just a really nice nice feeling i think it's also the reminder of that again it goes back to all the economical theories that were wrong because they suggested that humans are very much logical agents that will act in mathematical equations and turns out we don't so that's why all lots of economical theories actually were never right because we actually don't do what's right for us so we don't make the decisions that is the most logical we make very much human decisions and that's why I think those user interviews as you mentioned seeing them is one thing to see the synthesis in the data it's another thing to actually observe and understand why something is happening and kind of how a person reacts to certain things.
20:41I think there is a next layer of information that, again, I'm sure I will get at some point, but I feel like it acts as a special mechanism to better ideas. Yeah. Well, and I don't think any of us are out here to replace ourselves with AI. Like it doesn't, I know that's been the big conversation, but that's really our choice. You know, and when I say we, I'm also talking about product managers and engineers because, Because we as designers, we think this is kind of unique to our lived experience. But when I talk to my colleagues who are PMs or engineers, they're experiencing the same thing. I mean, engineers are like, oh, well, shoot, now generative code exists.
21:20And what do you even need me for? But then you hear of companies where they have AI write all of the code. And then it turns out that it's not good or there's something wrong with it. And then there's no one internal who knows good code. So they don't have anyone who can go in and fix it because no one has that skill set. So I think, I mean, design is really similar. Like, yes, you can generate a bunch of, you know, like, yeah, they're fine, you know, wireframes and even, you know, high fidelity UI from some of these generative AI tools. But it really is on the designer and, you know, those of us who have built like 20 year skill sets on this to have discernment and have your own unique point of view and your own taste.
21:59And it's very plural. It's not like there's one taste that's good. You know, it's not like, oh, my taste is good and thus everyone else has to have the same aesthetic point of view as me. That's very different across individuals, across cultures, across countries. countries, you know, we all have our own sort of style, but it really is dependent on us to have that. And that's what we are being asked to do is like have that decision-making skill as creatives to say, this is good. And this is what we want to deliver to our customers. And this is what we as humans will stand behind. And so if I'm, you know, giving something to, you know, my CEO, to a colleague, I'm standing behind that work.
22:42And I'm saying, I'm saying this is good. If they outsource that to AI, they totally can. Who's accountable for that work? Is it the AI? I don't know. And that's really where we have to really think about what are companies and organizations, but just collections of people with a shared goal. We are all trying to solve a problem in the world, create a business around it, et cetera. So you have to have people who are willing to take ownership for the quality of these offerings. And that's really what, you know, yeah, designers, PMs, and engineers are out here doing. And I think actually this goes perfectly into chapter four and five here, but I just want to say this as we kind of move into these really quickly.
23:24There's been a lot of discussion around AI slop and how do we avoid just because there's so many generative tools now just creating a million million things and them not being valuable these the tools to really well the the observational skills to really look at what people need that should be the very beginning of deciding what gets made that you know that and then the the tools to address you know to talk about market sizing like tam and um you know that like okay what's the business opportunity that is really what prevents what you could call like feature slop or product slop or service slop.
24:06We don't want to just create for the sake of making, making, making, making. It's, you know, we're tool builders and solution builders. So I think, you know, just that's maybe my watch out. And then, yeah. Would you like me to, shall we talk about that? Yes. Let's do go through the last two, because I felt like you had such a nice segue about, it's all about creating prototypes, visualizing things. So tell us more, what are you using at making visions tangible? Yeah, I'll give you all an example in case this is useful for you at your organizations. We had this really wonderful offsite this summer at Headspace between product management and design.
24:46And we got together in the Redwoods in Northern California, and And we used a bunch of different AI prototyping tools like Bolt, Lovable, some people were using Cursor, Figma Make. You know, we were just really playing and making a lot of stuff. And we used all of these to take some longstanding user problems that we had seen in the Headspace app for a very long time and come up with tangible solutions for them and make them visible and, you know, show them to each other. So really like get over that hurdle that's, you know, I don't know if for you all, like, you know, for me having worked at Headspace for so long, for six years, there were certain things where it was like, oh, that just feels like this problem that we just haven't yet solved.
25:30And we're all so excited to solve this particular problem. And so it was this fun kind of leapfrogging into the future vision to say, what if we solved all these? You know, this is what it would look like if we had this and this and this and this. and also just some fun, playful features because we get to play sometimes too. We need that as well. But this was a way to bring us all together and make this future vision tangible. So if you all are looking for ways to collaborate more deeply with your product management, engineering, or data science, whoever you collaborate with on a day-to-day level in your kind of like builders team, that's a really fun thing to do, to do a live, you know, we did it, ours was a two-day session, but it was really fun to kind of get all of us in front of these tools and making things together and really feeling that like collaborative and generative and fun spirit.
26:26So that's one thing I'll say. And then another way for those of you who are design leaders who may be in executive conversations where, you know, you're, like I was on the strategic planning committee at Headspace and we'd have certain conversations where it's like, hey, what would it look like if we solved that? It's a really fun design superpower. And I know you all have used it in the past to live sketch what that solution would look like. And even if you're in person, getting up at a whiteboard and sketching it out, that is really fun. And it's a uniquely designed superpower. But what I also found is, especially in the world of any virtual or remote work, to be able to quickly build a Figma Make prototype.
27:09I know I'm using figma make is the example so much there's a lot of other tools like that but to quickly generate a prototype with what you have in mind edit it to like look like the design language of your organization or your product you know using pieces from your design system but so it really looks and feels like something you you and your team would make being able to then send that out to other executive stakeholders is really really powerful because then there's a sense of hey wait oh this thing we've been worrying about or talking about, actually, this is a way we could solve it. And so, you know, it's a way to really just like help everyone take a big step forward and not feel like it's an unsolvable problem.
27:52So that's chapter four, which there's a million ways to make a vision tangible. But I remember times at Fjord where, you know, we had six weeks it would take to build these huge clickable prototypes, you know, and now you can do like a coded prototype in a few minutes, which is incredible. And then the last one on the competing on crowded markets, we actually already talked about that at the beginning, which was Google Deep Research. I'm a big fan. The good thing is Google Deep Research tells you all of its sources. So if there is a source that you don't think is valuable, you can ask it to remove that, or you can actually tell it to just use certain sources.
28:24And I've noticed that in the newer models, ChatGBT is also starting to call that out so that you can say like, yes, use that source, don't use this source so that you know you're really getting data that you feel confident in so that's that lots of tools we discussed before i think we want to focus more on the humanity today and the kind of the role of designer in a bigger sense in the world of ai but uh would love to kind of get the conversation about tools out of our system so we can all have the full list of all ai tools that currently today maybe not tomorrow but definitely today we are using we are happy with and we found helpful and we also have a special guest who will join us for also from the Headspace design team who will talk a little bit more nuanced about how she's using tools specific tools in her process and work so we'll go with nerdy in that conversation in a little bit so now we can actually focus on other things rather than tools because design and design leadership in this fast changing world no matter whether it is AI or something else is much more than just tools and the process that we have and one thing that we felt like was important to discuss is about design culture and the culture of the teams and Headspace I suppose was very unique place I visited Headspace offices with very cute meditation rooms and so many things that are just incredible so what is your take, I suppose, on what design culture, how is it changing?
30:04What is the best design culture for team's creativity? And yeah, how do you think about culture overall for a team? I love that question. I think, you know, I forget what question you were saying earlier that brought this up, but the power of designers is really like the collectiveness, the mass of creativity that happens when you get a lot of creatives together, like the kind of like next leveling of each other's ideas that just happens when you have a bunch of designers, a bunch of creators in the same room. But so team culture is, you know, one that I'm always like, I as a design leader, I'm a big fan of spending time building design team culture.
30:45I think that design is a process and a practice that has to come from inspiration, you know, and there are some designers who are really good at self-inspiring, they're kind of like a self-cleaning machine. You know, they go to museums, they go to concerts, they go to whatever, and they sort of fill their cup of their creativity, and then they're able to then pour that back into the work. And I think that's great and should continue. And it's also really nice when you, as a design leader, are able to bring more of that creative inspiration into the day-to-day work through different team rituals.
31:19So I'll give you all some examples of ones that have worked really well from places I've worked in the past. So I was at this absolutely unhinged and amazing creative technology studio that was called Chaotic Moon Studios. And we had a thing called Show and Tell. And it was, I think it was every two weeks. But people would come in, they would bring in something that they were nerding out on outside of work or a creative project. They were doing like, you know, we had a lot of brand designers who worked there. And so sometimes we'll bring in work that they were doing that was like freelance. It was outside of the studio.
Read the full transcript
31:51But, you know, hey, I'm making this album cover for this musician. I wanted you all to see it. Like, so they show all these cool skills that they have that they're working on outside of work, kind of their nerdy passions. And that was just like really nourishing. And then at Fjord, we had a couple of things, but the things that were probably the most advantageous to team culture, where we had tea time at 4 p.m. in the afternoon, which, you know, To those of you in London, you'll go, yeah, of course. But ours was like a social tea time. So it was like, hey, everybody drop what you're doing. Come to this.
32:23They had this big kind of like tall countertop table and have tea and talk with your colleagues. Like you're all in your weird, you know, workrooms being freaks. Get out of there and talk to each other, you know, like stop obsessing about your project and be a human for a second. And everyone would be like, you know, You see everyone's busy little minds and they're all like, and then they would get together and chat and have little snacks. And it was just really a sweet moment. And you'd often hear someone going around to all the different conference rooms going, tea time, tea time, tea time, to try to coax people out because they were nerding out so hard on their work.
33:00Because I don't know what's with us, but we designers love to hyper-focus. so you know that was a really sweet team culture ritual to just get us out of our our heads for a second and then what I always noticed is that we when the team would come back into our we called them war rooms at the time I think we would all call them project rooms now when you come back into those rooms you'd have a fresh mindset you know you're like your brain would kind of be like a little refreshed you'd have taken a nice break so that's that and then Hedsby's has a million unusual rituals and they've changed over time but we used to have a 10 a.m mindful break and a 3 p.m mindful break and at 3 p.m people would go on a 10 minute walk together in the before times when we were in person and at 10 a.m we would actually meditate together in person and that was incredible because this was pre-pandemic that we would actually be together in person meditating for just 10 minutes my colleague tom freeman would run those but it was just a really like you'd become a real human for a second and then, you know, and pause.
34:04So huge part of, you know, that was even across the whole company's culture. It wasn't even just the design team, but it certainly made us as designers feel more relaxed, more comfortable. Then, you know, fast forward through the years as we went into pandemic and we were all remote. One of my employees, Grant Nickel, who's an amazing designer I've worked with for in many different roles. He brought this absolutely unhinged, silly team meeting that I encourage you all to copy because it was so silly and stupid and fun. Um, that was called the work that's not work dot work in progress. So it was, hold on, I'm going to have to write it in the, the work that's not work WIP.
34:43So it's this whole silly acronym, but, um, but people would bring a topic that they wanted to just kind of do some nerdy research on, bring that, present it to everyone. There'd be like, you know, totally silly responses in the chat, whatever. And they, they had a structure. So it was coulda, coulda, gonna. Grant is from Austin, Texas. So it's got a little Southern flair on it, Southern US flair. So it was, I could have talked to you about this thing that I'm obsessed with, but I'm not going to. I could have talked to you about this other thing I'm also obsessed with right now, but I'm not going to.
35:19I'm gonna talk to you. I'm going to gonna talk to you about this. And then the designer just goes off on this, you know, 15 minute slideshow of, ah, you know, this is how the city of New York worked with this graphic designer to do the I love New York campaign and like a full history. And everyone's like, wow, this is so fascinating. So interesting. So, you know, not only does that build community within the team, but it also, it's this really like kind of fun moment of giving inspiration to the team. Like you get in what you put out. So as a design leader, being able to give inspiration to a team, you get more inspired work back.
35:59And you also get designers who trust each other and they collaborate better together and they like each other. And, you know, they have a sense of, um, Hey, when I'm stuck on a project, I can go to my manager or I can go to Cal or I could go to another designer because I know them now and I'm not intimidated. So, you know, really like that building of culture creates, it dismantles some of the walls between creatives who can get protective of their work or whatever, because you've made a safe space for them to just be humans and to nerd out on things because we're nerds. I mean, you know, cool nerds, but you know what I mean?
36:33Like we have passions, we have interests. So yeah, so that's my long, long, long diatribe. But I do think, you know, because design is a process that is nourished by inspiration. That's team culture is so important to like, as a design leader, I think your main things you need to focus on product strategy, design process and operations and team culture. Those are really, and not necessarily in that order. It's probably team culture first and then operations and then product strategy. This is just, yeah, it's so key. It's so great that you mentioned the importance of culture, because I do believe in this world of technology and things that everywhere, everything is so fast.
37:17Focus recently did change to how can we be faster? How can we be more efficient? What kind of tools can we use? Which is all great questions. They've always been there through history. I think we always try to be more efficient, do everything cheaper, faster. That has always been the conversation. But we all know that for great products, great creative ideas, what really matters is the humans, their culture, how you work with the team and all these things that are not as tangible as the tool that you use, as the process that you have. And they always been very tricky. And there are so many examples of brilliant companies that no one could figure out how they do what they do because it was this special source that they had inside the teams that just gave people better ideas and gave people this extra space to think.
38:15And no way I can figure this out because it is a special source. So I love that you mentioned all these rituals that not efficient, can seem pointless. You can't put a number on it, but they are the ones who probably will make the biggest difference when everyone else, every other company, every other team is trying to operationalize everything out of the process, where everyone is trying to be most effective. And someone will win. Someone will have the cheapest, fastest process and product, but someone will just have a better one. And that's the thing that we can be uniquely good at, building these cultures and bringing a bit more humanity.
38:55What did you feel like that changed? I'm sure you worked in different teams and some had great culture, some maybe didn't have such a good culture. what did you feel like a good culture in those rituals did bring in terms of the real difference in work or in anything else? I mean I think you know a continuation on what I was saying before is like it creates a more collaborative and self-trusting team so then you know because every designer has slightly different skill sets then you have designers who are comfortable working together and giving their you know expertise and knowledge to each other versus I would say the design cultures, and I've really maybe only worked in one that was really not the most trusting, maybe two, but the design cultures where people are competing, where designers are competing, where there's more ego than collaboration, those are the ones that rituals like this can help with.
39:52And I would say like rituals like this ensured that the headspace design team was not like that, You know, that really it was a safe space to be real, to be a real person, to be human, to be flawed at times, to need help, to want help, to want to collaborate, to want to riff. You know, it really, yeah. I mean, I think because design can be a vulnerable process sometimes, you know, you're putting your original ideas out there. You're making a physical artifact that everyone can see. you know, I think that can make some designers more, you know, a little insecure or competitive. And when you can create structures that dismantle that, you know, or structures that build trust, build collective inspiration, build collaboration, then yeah, I mean, the work is better for one, like in a measurable way.
40:48But also for you as a design leader, if you're thinking about resourcing projects, you actually now know that the designers will start to work together. There's not friction. There's not, you know, if you have one designer who's got really great visual design skills and another has great research skills, you can put them together because you know, they'll actually work together versus, you know, oh shoot, they're so different. They're going to compete or be mean to each other, whatever. So yeah. And I think Fjord did that really well too. I think we had a, we had service designers, design researchers, you know, people who largely because of the structures that we had there, we're willing to really collaborate and, you know, the rituals.
41:25I would say Fjord, another thing that's worth mentioning, Fjord had a very good team culture around continuing education. So there was even a team called Fjord Evolution that went around the globe doing in-studio actual training sessions on, you know, ethnographic research, prototyping, usability testing, you know, I mean, just really powerful skill building. Andy Pellain was on that team, Martha Cotton. It was really like kind of an all-star. You're like, well, I'll learn from these folks any day. But that built a culture of continuous learning. And so then that inspiration that you need as a designer was actually being given to you at work.
42:06I mean, we were learning about computer vision. We were learning about autonomous transportation. We were learning about all these things through Accenture and through Fjord in, this was like 2017, 2018. Like we're talking about all of it now, but we were learning about it then. So to go all the way back, actually, Ekaterina, to your question around like consultancies and what's the value of them as the like knowledge holders. It's true that like some of that book knowledge is no longer as, you know, premium, but I would say that access to a creative team that is big and, and can inspire each other is still really valuable, especially if you're a company that may only have a few designers in-house, like if you just have a very, very small design team, having access to these hubs of like big groups of creatives is still really, really valuable.
42:56I think that's where those, you know, still are really huge. What you mentioned also kind of loops back with what we started where you said that designers' role is still to understand the context, to pick the right idea and to make the right decision. Yes, you can use all the tools in the world, have all data in the world, come up with 100 ideas in a world, but the actual role of a designer, and especially of a design data to understand which one is right, which one for this context, which one for this business, which one for this situation, for this user, for all the pieces that we have, which one is right, and which one in general is the best.
43:34And culture and rituals and understanding team and having access to all this extra thing and having trust with everyone that's what contributes to that intuition because i think if even if you are the one with the knowledge and the one with everything if you don't have this great culture where you will be trusted with the best decision where you can discuss with everyone what would be the best decision again you won't make this best decision So I feel like it kind of all links together with what is the future of designers. It is to make the right decisions with the tools or without the tools in whatever combination.
44:16But also that requires a great culture that will enable that. Well, just I love what you that you brought up intuition, because I like talk about designerly intuition a lot. And it's something I probably borrowed from John Colco, who is one of my design teachers earlier on. And there is something about, I'm sure you all feel this, but there is something about certain new designs or certain new features or certain things that you as a designer or design leader may propose that sing. Like you can feel there's something there. This is exciting. It's new. It just sings. You can just feel it. It has energy.
44:57It has momentum. It's really exciting. and um jane kiabyab who's a great designer at headspace principal uh product designer she had a feature that she showed me a few months ago where we just all we were on a zoom and we all what's that you know i was like and you could just feel it had like this magic quality it was new it was something no one had thought of it was so exciting you know we're all just like what tell us more and and i you know for us it's really that is your designerly intuition speaking. And I will say it's really hard for our product colleagues and our engineering colleagues and our CEOs to feel that with us because like we're creatives who just, you know, we've dedicated our lives to creativity and we can kind of feel where something might go.
45:42You know, we just have a different, you know, sense of making and more trust in making. And so I'd say we're just to bring it all the way back to our AI and, you know, synthesis tools. I think what's really cool is that is where you can help. You can build a business case around it. Like, Hey, this is really exciting thing. And here's what it does. And here's how many people it could help. And here's the unmet market need for that. So it really, you know, for those of us who have to really sell in certain ideas to, to get engineering time to build it, um, you know, that's where that happens maybe in a future world.
46:16And we just use cursor to use the, do the code ourselves but yeah anyway i'm personally not on that one yet so we'll see well um i think this is a great point and now we are actually uh have an exciting part of today's conversation because right now we have an extra person who will join us to talk all things ai and humans incredible rachel from headspace design team who previously worked at lots of fantastic companies and now Obviously she's doing incredible work as a senior product designer at Headspace, but before she worked at Calendly and lots of other great companies where has been focusing on UX and product design and now plays around experiments with lots of AI tools and specifically how to use them.
47:07And this is why we wanted to bring Rachel to talk a little bit more about nuanced things that where AI can be helpful and unhelpful. Rachel, how are you doing? Hi, thank you for having me. Well, let's dive straight in because we already have been having a conversation about where tools sit in the process. I suppose, apart from what they do, let's talk about how you use them, because you work with kind of trying to figure out the best process possible every single day. So can you tell a bit more what you found the most helpful in terms of how to use those tools to bring the most value to your design process?
47:48Yeah, so I think the first thing about thinking about how I use AI tools is first understanding where my own design process. So I think as a designer, you need to know your own process first. And there was a mentor who once told me where I was telling them where I wanted to become much more technical as a designer. and this was like five or six years ago. And they basically said, that's not your strength. Like that, like your strength is like in the research and in understanding why, like these different aspects. And they're like, don't fight your strengths. Like don't invest your time in fighting what you're naturally good at.
48:26And I think with AI, that's ever more present, like understanding what you're naturally good at and then using AI to expand that. So I think they're like, It's not that you have not a lot of tools to choose from. There are new tools coming out every day with AI. It's really understanding which of the tools that are out there, experimenting with them, and understanding which ones are really going to expand your reach and impact as a designer. And so that's all to drill down into. I've tried a lot of tools, but I mostly just stick to using Claude in my process. I think Claude has done a really good job of framing their tool as a thought collaborator and being able to enter into that process and think like, I already know a lot of what my like skills are.
49:14And I kind of, I was joking earlier is like, I view AI as my intern and like the tasks that I know that I need to get done, but don't necessarily like, I want to spend my time as the designer in that creative part in, in the, in the work part that like gives me joy and less in what I would view as the labor part, which is the, like the part that is, could be done by something like AI. So, and I think that's A part. B part is understanding what are the strengths of AI and how you can use those to service you. And so, like, a specific example of that would be there was a feature I was designing for like an AI note taker for our therapists.
50:01and in that I had not actually designed AI flows are a little different from more traditional UI flows and I was trying to find a feedback mechanism and I knew I didn't know enough of the interaction patterns for this and so I simply just prompted Claude to be like out of the AI interaction patterns out there like what are the ones applicable to this section to what I'm trying to do for feedback and can you just show me some examples of those that are interactable because I think a lot of times when you're trying to understand things in that section and in that like a specific vein, I'm just trying to play around with different ideas at that point.
50:42And so being able to say, okay, I'm reviewing what's out there of the new interaction patterns. I'm selecting which ones are the ones that are best fitted to this situation. That's my designer taste intuition. And then I'm saying, okay, now that I have a general direction, I can go work on refining that and getting that up to the level of polish I expect from myself and want to deliver and that just helps like it takes some of the like the circularity that you have to do in design and kind of speeds up that area so that you can get to the part where you can deliver impact that is in the more I'm like anyone can stop me at any point if there's a point where you need to drill down But that to me is like a part of how you can use it to like explore some of those unknowns that may be like that bring you up to date to the current state.
51:33I think the other half of using it is, for example, I had to synthesize some survey results and then do user interviews for them for a for understanding kind of like why members are starting to drop off therapy. And I think one of the joys that I have a designer is actually interviewing. And I have a background in co-design, participatory design methods. And I think making sure that your interview is fun for you and the participant is really important. And so I had this vision of creating like a mini member journey map, like a game of life almost, and say like, here's the steps in the process.
52:17Like, where do you fall off? Like, where is this going on? And I had that vision, but I also had like three days to like get it going. I promise I didn't give her that only three days. Yeah. And so, yeah, I think that's the part where I make the work hard for myself, where I'm like, I actually, I could have just done like a more simple one, but I had this vision, right? And so I think in a normal circumstance, I would have been like, I don't have time to execute on that vision. But in the, I was able to just say like, hey, I know that I need four to five points on this journey map. I have this survey data.
53:00I have a vague outline to fact check what the AI outputs are that I know that it needs to be like. I have a set of questions that I have from some of the other researchers that I need to hit at. I was like, can you overlap these, attach the themes, put the questions underneath, and I'll design the journey map, which is the fun part I want to do. And so I think it's like just figuring that out of where you can use it to get to the parts of the work that you want to do. I have this, I mean, I'm sure AI will get past this point at some point, but I kind of view it as a mental calculator. Like you still need basic math skills.
53:38Like you can't just depend on a calculator to do all the things for you. But there are like, to me, where generative AI is right now is at that level of like, it's doing those mental calculations that you know you have to do and require thought processing but are not where the work is so yeah those are just two examples I can go yeah let me know if there's anything else no I love these are great examples and I love that you in your example you shared something that you came up with but didn't have time to do versus I think that's that's again and going back to our conversation that we had, we are still in charge of bringing ideas, coming up with ideas and thinking what's the right idea, but yeah, we can save time and execution, that's for sure.
54:26I have one question for you that actually was coming from our community overall about the role of AI. In your experience at Headspace, where has AI actually changed a design decision rather than just sped up the things? Could you walk through one concrete example where the product experience you shipped would have been meaningfully different if AI had not been involved. Rachel, I have an example if you don't. Okay, yeah, I don't know if I have one off the top of my head. I can give mine and then if you think of one. So Taylor Berg, who's an exceptional PM at Headspace, she noticed that our competitors had a different feature on their websites than we did.
55:09Like we were missing this price calculator piece for insurance. This is for US-based, so sorry for all of our friends in Europe. This is like US health insurance, you know, junk that you have to deal with. But anyway, so she saw this need, but as a PM, you know, doesn't really know how to make things. So she ended up using a generative AI tool to create some kind of like wireframes to say, hey, these are the things that I think we need. And then in a very unusual process for us, but a new one, she gave those to Jonathan's design team. And a designer on his team started looking at that. And what was materially different that wouldn't have happened if Taylor hadn't done that and if this clickable prototype hadn't existed, this coded prototype actually, was that there were certain use cases that the designer and that design team and Taylor would not have thought of that the generative AI tool put into that prototype.
56:07And it was certain like error states, just certain use cases that, you know, eventually the team would have found those once we did like a bunch of technical reviews. And we're like, what happens when? But those were all laid out. You know, imagine like they're just laid out on the table from the get go. And so it was a really, yes, it sped things up because those were already there. But it also it kind of was almost like a not a fact checker because that's wrong, you know, but it was a checker for what was missing that might need to be there. And then the design team took that and went several levels further with it.
56:40Lisa, who's on that design team, did that work. And it really, you know, it basically provided this very kind of more diverse jumping off point than what the team would have naturally started with. Had Taylor just said, hey, we're missing this feature, the team would have done a bunch of like competitive research and they would have found some of that. But it would have taken longer and they might have missed some of those error states or those use cases. So that was cool. It kind of like helped, you know, dot the I's and cross the T's, like just find those extra pieces. So deeper, more information, deeper edge cases.
57:19And yeah, essentially thinking through more rather than what I suppose you would normally do. Great example. And then Lisa got to focus on craft. She got to play and enjoy. And so we can do an illustration here. like she was starting to have a little more fun. Rachel did you think of any example where design decision has been changed like you thought one thing AI thought another thing and one wins or maybe the other way around who knows. I think in Cal's example it's a really good example of how you can use AI to create artifacts that shift decision making and how you can like one of the things that I'm a real big fan of is research through design, which is, you know, the approach of essentially using design artifacts as research.
58:07So I'm not necessarily in, I haven't necessarily used it in that way yet, but I also am still trying to figure out if that's where I want it, where I want to use it and how I want, you know, in terms of a human AI collaborative system, I still view myself, I still view myself on top of that. And so I, you know, for now, so I think I'm still trying to figure out how I want to let, if I want to let AI be a bigger driver in that, or if I'm still viewing it as the kind of expander, if that makes sense. And is there anything you would never do with AI? We spoke about kind of human stories and having that, but any other decisions for ethical, for security reasons, for fun reasons, for any other reasons, anything you wouldn't actually give to AI to do?
59:10i mean i think for especially like right now where in my mind where generative ai specifically is i would not give it a lot of things i think it still needs very much a human in in that loop so to speak to just like verify any of the outputs to understand that system like i know like i'm really big on research and making sure that you get those inputs right and to me ai is the output clarifier and i know that's not exactly answering the question i think it's just a very broad category of what i would not give to ai well thank you so much rachel for joining us for for this little deep dive into reasoning with ai and thinking where it fits we're now going to a q a part of our conversation.
1:00:06We have hundreds and millions of questions that have been summarized by AI, but we do not trust the summaries. So we'd love to hear first from lovely humans. So question number one is, if AI becomes your new intern, how do we support real human interns, be interns? I worry about junior and grad roles struggling to get work. Chris, this is a great question. Thank you. I'm actually really happy that you wrote this in because on the Headspace design team this summer, we hired a couple, you know, junior like entry level designers. And it was really powerful to see what they brought to the team. They were above intern level, but, you know, really kind of new in their careers.
1:00:55So here's what I would say, you know, for those of you, especially who are design leaders, and you're looking at how you staff your teams, I think that there is phenomenal value to be gained from junior talent, you know, from folks who are new in their careers, because they're bringing all of, you know, their experience. And it could be, in the case of one of our designers, they were a career switcher. So it wasn't so much that they were like this right out of college intern, but they were new to design. And where I think AI can actually help those particular designers is some of the analysis and synthesis skills and capabilities that we were talking about earlier.
1:01:37That can actually help them clarify their thinking. they can ask design questions to these tools if they don't feel comfortable asking those to more senior designers you know if they're still in that viewpoint that I certainly was in when I was a brand new fresh designer or like you know I have a question I feel so embarrassed to ask it you know but actually they can now ask you know very complex tools on the internet those questions and get really great answers and then they also can use these tools to create you know the v1 MVP wireframes of their work and then use their own emerging taste and discernment and skills that we've been talking about to build iteratively on those initial wireframes.
1:02:21So, you know, there is, I think these tools can become almost like continuing education tools for those emerging designers. So my ask to fellow design leaders as you're hiring is to continue to hire those, you know, So we call them T1s, but, you know, other places are like junior level, you know, these emerging designers and interns and really allow that skill set to come in and allow those humans who have devoted themselves to this creative practice to join the team and then bring all of their expertise, their ways of thinking, their points of view, you know, all of that into the work and use these tools to actually kind of up level and move forward.
1:03:04their work. So, because I have heard that in a lot of, like, you're like, oh, we're getting rid of all the junior level ones. Like, well, you know, actually I wouldn't do that. We need all these viewpoints on the team and those designers are going to be needed. They need to learn from other human designers by doing, by making, by working shoulder to shoulder with senior designers, with mid-level designers, with leads, et cetera. They need to learn that to be the next generation of designers. We're going to have to mentor folks. So we can't just, you know, I think, you know, Rachel, when you were talking about intern, it's a little different.
1:03:39It's like more of a, it's an assistant in that classical way of assisting the work, you know. I also think the nature of work is changing within this field. And so the things that we would typically think of as intern things are shifting. And so like also that power that you have a designer and how you position yourself I think is ever more important of like how can you take care of that like basic underlying skill set that is enabled by AI to further empower you as the designer and how you are packaging your design skill set so I think you know you know right now in the industry there is that like blurring of terms between like makers builders all of those kinds of stuff.
1:04:30I have my own issues with those terminologies, but I do think they're getting at an underlying fact that the line between like code, no code, like the lines between all of these professions are blurring with the use of AI. And so I think how you tell your story and your narrative as a designer is ever more important. So, and that's where I also think like design education is so important to understand like the depth of research and frameworks and all of this kind of stuff that are already out there to help guide your thinking and kind of set your positioning as a designer maker builder I think these are both great points of view and I also think that maybe the career journeys will be very different from now because I feel like a big part of very traditional even now, but maybe 10, 20 years ago, it's like first you learn the hard skills, the Photoshop, the whatever.
1:05:30Now that you've learned that, now you can do, okay, fun things. Now you know how to use the technology. You can do the fun. Now you learn the fun things, you can do the human things, okay? You can actually interact with people and collaborate. So it's like, it was very much linear and step-by-step process. Before you learned one, you can not move to another one. And then now this first part of learning technology, learning the visual, like it became so much faster that you can get to the point where you collaborate, where you do other things much quicker. And maybe therefore you discover your different career path or different way where you wanna fit in the company much faster, because I felt like that's what took a lot of our careers of like, okay, what do I do?
1:06:13Okay, now I learned this, oh, I learned this, but I don't wanna do it. Can I do something else? And now you can get through this iteration process faster where your career goes. And I think that should be very empowering to junior team members to kind of embrace that. But also, I agree with both of you that we do need more young talent, A, to grow to senior leadership eventually, but B, for ideas and thoughts. We were those people once, once, five minutes ago. Exactly. there's this really great paper that I love it was written a long time ago and I think we like to think like AI is a new technology but there's so much historical precedence for this exact type of technological kind of innovation like when you think back this paper covers it's called art after de-skilling and it talks about the history of portrait painting before the invention of photography so when you think about what portrait painting was originally meant to do there were huge painting workshops you know when you think about like like Botticelli all of them they they were meant to like it was an industry capturing like someone's portrait with the invention of photography it it kind of just like completely flipped that uh career field and so at that same moment you also had impressionism come out of that you had all of these painting movements where essentially a lot of these painters they had a deep skill set but they're freed from that moment of like having to copy reality something else is doing that now and so I think we're at that kind of moment here where I'm it's either trying to figure out do you keep being a portrait painter because there still are portrait painters out there or do you figure out like what's your version of impressionism in this space like what's your version of like cubism whatever you want to go after like there's that opportunity for you i think there's also underlying that the other historical precedent is the luddite movement and the like that movement was originally around like it's essentially workers rights like they were there is not like it wasn't about necessarily and being anti-technology it was that these mechanical machines were replacing like traditional weaving practices and within that they essentially when the companies brought in these larger machines, they use that as a reason to depress wages.
1:08:40And so it was that they were strategically targeting those specific weaving mills that were causing that. And so I think there's this dual tension between like, yeah, I do feel like if I could be replaced by AI right now, my company would try it. You know, I don't think that's like unique to, I think that's the industry right now. It's like trying to figure out like that's tech. So I think there's a divide between like trying to position yourself like to not necessarily view it all as a detraction but to figure out like how do you continue to evolve your skill set to find your own impressionism and like trying to like tee that balance i think is the big question of this transformational period that we're in yeah and what are your thoughts where do we find like both rachel and cal where should we start looking for this new cubism and expressionism and impressionism like in general how do you go about finding your other humans yeah it's good yeah that's exactly what I was gonna say too yeah it's I mean we actually talked about this exact topic at CoLab this year which is dscout's annual conference for design leaders and and literally the painting the portrait painting versus, you know, photography topic came up.
1:10:01And, you know, the kind of general consensus, which I will share is like our minds want to forecast what that's going to be, but we actually don't know until we get together as creatives and do it ourselves. Like we, you know, those movements like impressionism, cubism, you know, pop art later on, it's like those were organic. They came because people started to make things together and then they, you know, they influenced each other And there was this sort of, you know, this cultural, it was very organic, you know, it was like, it wasn't like a critic said, okay, now you're going to do cubism.
1:10:36Okay, guys, go do cubism. You know, it was like, okay, we're doing this thing. And then a critic labeled it cubism. They're like, oh, that's cubism. We're like, oh, okay. You know, but it was really organic. So I am, I think this is going to be the really interesting thing is to see what designers and creatives start to do in this world where like to some of your points, Rachel, or what you were saying, Ekaterina, like certain tasks are either done collaboratively with AI or, or, you know, given to AI to do. like what do we then what are those things that we then have fun doing you know are collectively as designers or there was someone in the chat who said oh this conversation makes me miss working with other designers like maybe some of these tools become a way for us to like if you are a solo designer at a company to not feel alone because you can do some riffing and then you can also talk to friends who are designers and riff with them and you know just like maybe there's a little more time and space for that like creative thinking because some of the things that you didn't really want to do are able to be done more quickly and so you end up with a little time on your hands to play with so those are those are my thoughts.
1:11:45I would also add to that when you were saying about these big movements that were happening and like again if we take painting or anything else in terms of artistic movements you're so right they all were very much about collaboration about communities about um they had studios together again obviously futureland academy is obsessed with bauhaus and what it was at the movement they had a space they were together they they discussed ideas and it was very organic and in that sense again i think we should focus and shift the conversation from the tools to how can we come together how can we enjoy each other's company, how can we discuss ideas and from there the good work will happen.
1:12:28We actually had in our previous podcast episode, we had Charles Vigas who was talking about how AI right now is very much an ego driven solo person tool of like, I can do multiple things. I don't need other people. I can do everything. Well, it's a way to do it, but it's not the only way. and definitely the best ideas come from collaboration, especially in design and creativity. And there is no much emphasis in the tools about collaboration, about bringing people together, about how can we all harness our powers, our skills, our thoughts in a collaborative way with AI still, but how can we come together?
1:13:14And I think that could be potential next shift where we will start actually using these tools less in a singular thing of I can sit on my own in the room and run a company and do everything myself to how can we all come together and come up with something no one thought of before using these new technologies. I love, thank you for bringing that up. And that was such a good conversation that you had with him because I think where he brought up kind of co-design and participatory design and making sure you had other viewpoints in the room, like IDEO was always so good at that. They would hire clinicians and they, you know, you'd have people in there who have like behavioral science backgrounds, they're not even designers, but they're on the project teams because they bring a really important viewpoint.
1:13:54You're so right that like in this era we're in where someone can be alone with an AI tool and create like an entire business, you know, create the app, create the business model, create everything. The kind of missing piece is other viewpoints from other humans, like someone to help not only like prevent them from building something that no one wants and no one will use, you know, which AI can help you kind of hopefully prevent some of that. But you never know. Like sometimes you do need a stern mentor to be like, does anyone need that thing that you're trying to build? You know, or someone on a team who comes from a different background and they say, I don't, this doesn't, you know, we're not solving this certain problem with this.
1:14:35Like the, I think, you know, the hope is the watch out that we should probably name here is that, you know, one person in a room doing the design, development, launch, you know, biz dep, like doing all of it. And not that you can't do it, but just that the risk there is you will miss asking the right questions and building the right things because you may have such a narrow viewpoint, you know, kind of a, you might have blinders on or biases that you're not aware of. And then the tools, you know, they're known for, they love to validate the human's viewpoint, you know, they can be really like congratulatory on your ideas.
1:15:19And so if you don't have people with discernment to really kind of push back and ask questions and add in other ideas that that could be that's probably the watch out that we should name. and that's why participatory design is so helpful which yeah I've done a lot of yeah yeah I think like within that training and I've also done a lot of like futures work in my career as a designer and I one of the reasons that I think participatory design and futures work combined is so powerful and like to pull out some of those design terms like we're in a plural verse like there are like Like you are like if you are like your view of reality is one pinpoint and how it's constructed, you know, so if you are that one person constructing your thing, great.
1:16:05You can hope that you've done something that can connect. But if you're not like being that conduit, if you're not like interacting with others, finding those signals and inputs to create something, then it is very one sided. And that just gets toppled very easily. And so I think that's the power of having multiple viewpoints as you're building something holistic and well-rounded that actually reflects the reality that we live in. And I think there are cases of people who are really good at being that conduit and not necessarily having to do all that, but I think those are much rarer than we want to think that they are.
1:16:45And I also think that one of the things that I have thought about with a lot of these tools and a lot of like how AI is being framed and shaped right now is it does make me uncomfortable. And I think when I was inspecting the reasons behind that, I was talking to one of my mentors and she gave me this quote. I don't know who it's from, but it's essentially like when you feel that discomfort, it's because you're living in someone else's dream of the future. like right now with a lot of these tools there's another quote that it's and I'm going to translate this and then I have to go actually but it's that money is fossilized power and so when you think about where have people who have money who have fossilized their power have put that they've put it into building the technological tools that we're now using it the big VC funds like it's their viewpoint embedded in the technology?
1:17:44And so you have to think about how you are using that, but also subverting it in your usage of it to keep your own self-determination and path that you want to guide it in. Because I think there's a, it's like a dual process, like the tool is shaping you and you also have to shape the tool. And with that, I have to go. No, but that's great. Thank you so much, Rachel. Thank you so much, Rachel. And we'll stay with Kel for a few more minutes to wrap this up. But, Rachel, this was incredible and really, really needed point of view on the future and tools and AI and humans, humans and collaboration that we all need.
1:18:24So thank you so much, Rachel. So, Kel, following from this question, there is one more question that I would like to answer before we start wrapping up, which is around the uncertainty and everything, anxiety that everyone has about AI. So, maybe you have perspective on that. So, Sharon is asking, entering the unknown is uncomfortable, but essential for creativity. How do you cultivate the mental resilience needed to stay in the uncertainty when AI tools constantly push us towards fast, confident answers? oh it's such a good question yeah i think this is where you know you all are gonna be like gosh you're such a stereotype you worked at headspace so i do a lot of mindfulness work outside of headspace and i did it at headspace um the unknown is something that you know our minds are really uncomfortable with like it's you know we want certainty especially in a workplace where you're being paid for your creativity we want our we want that certainty you know we're like oh my god you know, it's so important because it feels like it protects us.
1:19:23But, but I think this is where you as a human, and I actually said this, recently said this at a conference that, you know, you as a human need to nurture yourself outside of work and recognize that like, there is a lot of uncertainty and a lot of newness in all these different tools. And these things were sort of being asked to learn like on the job. Well, you got, you all are doing a cool job of listening to a, you know, joining a Zoom and learning about it outside of work too. So good job. But, but, you know, we're being asked to learn these things while we also have these, you know, what I would call like strong professional identities, you know, like you as a designer are needing to, you know, make work and, you know, kind of be certain and be confident about that work, you know, and so how do you keep that growth mindset and the learning mindset that is required to learn these new tools and to come up with your own fun workflows and processes that work for you with these tools if you want to use them and still confidently deliver the work you're delivering at work.
1:20:31And what I would say is that's where mindfulness comes in. So it's such a predictable answer from someone like me. But this is where really giving yourself time and space outside of work, you know, whether it's a daily meditation practice, whether it's going to therapy, whether it's going on a run, whether it's, you know, hiking in the wilderness, like whatever you need to de-escalate your nervous system to really get to calm down, to really get to feel present, to really get to relax, and then kind of understand what about this, like get really curious with yourself, what about this is making me so uncomfortable?
1:21:10You know, like, is it that I'm afraid of learning or I'm afraid of getting it wrong. Or, you know, we have ideas that like, we'll try something and it'll fail. You know, we have all these different ideas, but just to really give yourself that time and space to reflect so that you are able to kind of what I would call it, like soften the impact of those ideas. Like you're going to still have those ideas about yourself and your world. Some of them you can let go really in a, in a great, you know, if you're doing a particularly awesome mindfulness practice or a great therapy visit or whatever, but to soften the impact of them so that you feel more in command of your own work and you're able to decide and go, okay, here's the tools I want to use.
1:21:54Here's the tools I don't. Here's how I want to work. Here's how I don't. Here's how I want to self-educate, go to a future London academies, you know, however it is, but, you know, kind of finding what's right for you as you navigate that, because it's, yeah, it is a moment of a lot of learning and growth. Most of us learned this stuff when we were in school or, you know, did continuing education. And then now once you're in the workplace, you're expected to just be like, you know, you got it. So, yeah. So that's a really, really good question. Long answer, but that's a really good question. Well, I feel like this was such a nice way to wrap up the conversation about how can we survive in this world that is changing it's all about mindfulness and looking in words but also collaborating and connecting i have one last question left for cal which we ask as you know everyone who comes in our wonderful podcast which is a bit of a philosophical question if you could change one thing in the world what would it be ah i love this question um yeah my answer i hope this doesn't feel like a stereotype too but it would be more empathy and more compassion i think that we're in a moment where a lot of people are fighting over ideas and i would not say that the um i think we all know this that the algorithms are particularly helping us with that especially on social media and um you know we've we've stopped really listening to each other as humans so that's the one thing i would change is really increasing people's ability to listen to each other and have more empathy and compassion and recognize that if someone else has a different point of view than you, it doesn't mean necessarily that they're wrong or you're wrong or you're right and they're wrong or vice versa.
1:23:37It just means it's different. And it doesn't mean they're a bad person. It means they have the information that they have, or they're reading that particular side of, you know, Instagram or any platform, you know, name the platform, but they're reading that particular algorithm's path. And really just to, yeah. So that's the thing I would change is just a little more of that listening in the world. Oh, 100 % agree with you. I do feel like we need more humanity, more way for each of us to connect with people that have different opinions, different views, still human, we're all human and we should find more ways that we can connect, more similarities than differences, more ways that we can talk to each other and inspire each other than argue with each other.
1:24:30So yes to more empathy, more kindness and more collaboration between humans. Thank you so much, Carl. It has been such a pleasure, as always, talking to you, learning from your perspective and wisdoms. And obviously, thank you for bringing Rachel who is our special guest. It has been such a joy hearing different angles of your process, your thinking, your philosophies. And thank you so much for collaborating with Future London Academy on our product design strategy course. I already seen how many incredible lives they changed then helped an empowered designers to be more strategic, to understand more about how they can contribute to the business in a wider way and now with the extra addition of ai and everything else designers can definitely have more influence organizations through the power of creativity and between everything else but understanding the wider context and connecting the business and the user as this magical glue so thank you for everything any last words anywhere people should Good.
1:25:42Follow you, find you, recommend you anything, any ask that you have. I mean, yeah, I mean, I'm on LinkedIn. You can find me there. Thanks, Cal. And as always, if you find anything insightful, useful, helpful, please share it because we love hearing your insights. What changed your mind today? Did you find anything surprising, interesting, fascinating, inspiring? Any quote you would like to share? Please do. It brings me extra joy reading after this podcast, all the LinkedIn comments, all the posts on Instagram that I see from our wonderful community. So please don't be shy, share your knowledge with the world.
1:26:18Thanks everyone for joining and until next time. Bye. Bye everyone. Thank you.
From the publisher
With so many AI tools flying around, it’s easy for creative teams to feel overwhelmed. Which tools actually matter? And more importantly, what stays uniquely human in design leadership as technology evolves?
In this episode of Design Leadership in the Boardroom,Ekaterina sits down with Cal Thompson, VP Design at Headspace and curator of Future London Academy’s Product Design Strategy course. Cal shares how AI is changing the strategic power of design (not replacing it), where these tools genuinely help guiding roadmaps, measuring product signals, prototyping visions, and where they don’t belong at all, especially when it comes to anchoring human stories.
Joining as a special guest, Rachel Arredondo , Senior Product Designer at Headspace, offers a practical, grounded view of AI as a thought collaborator. She shows how she uses Claude to expand her reach without outsourcing judgment, and why designers must shape tools just as much as tools shape us.
Expect a conversation rooted in empathy, culture, and creative responsibility, plus a clear, usable framework for deciding where AI fits in your design process.
What you’ll learn
- Why design’s strategic influence can grow in an AI-enabled world
- Where AI helps most across the process of guiding roadmap, synthesising measurement signals, prototyping future visions, navigating crowded markets
- Why human observation and interviews can’t be replaced by synthesis tools
- How to build a design culture that fuels collaboration, trust, and imagination
- What AI means for junior talent, and how leaders should rethink career pathways
- Why the next “design movement” will be collective, not solo-AI driven
Who this episode is for
Design Leaders · Product Designers · Head of Design · Head of UX / UX Director · Product Design Lead · UX Design Lead / Design Lead · Design Managers & Senior ICs navigating AI adoption · Solo/In-house designers · Creatives and cross-functional partners (PMs, researchers, engineers) shaping AI-enabled products




