
In our conversation, Alison challenges the Silicon Valley orthodoxy of radical candor with her concept of radical humanity. She also explains why designops is fundamentally heart-driven work, and draws unexpected parallels between organizational dynamics and the regenerative systems of Puerto Rico’s El Yunque rainforest.
Loading summary
A
Everything's changing so much right now. Engineers are getting laid off, but are designers going to become even more relevant? I'd like to think so. And so I think that design operations, it's change management, it is human centered, and it is a process that is heart centered. And that's the difference.
B
I've worked alongside people for years only to realize that I know nothing about their personal life and it probably affected our working relationship. Knowing your colleagues as humans reframes inevitable challenges at work. Had I known my colleagues better, would we have worked through disagreements better or found new ways to collaborate? Yeah, we probably would have. Alison Rand, who helped establish the discipline of design operations through her roles at Hot Studio, Frog, Automatic and SAP, explores building relationships at work in her new book Centido. It's a term that encompasses both making sense of things and feeling them deeply.
C
In our conversation, Allison challenges the Silicon Valley orthodoxy of radical candor with her concept of radical humanity. She also explains why Design Ops is fundamentally heart driven work and draws unexpected parallels between organizational dynamics and the regenerative systems of Puerto Rico's El Yunque Rainforest. This is Design Better, where we explore creativity at the intersection of design and technology. I'm Eli Wooltering.
B
And I'm Aaron Walter. At DesignBetter, our primary mission is to produce work that helps people like you refine your craft, improve your collaboration skills, and get inspired by the creative process of others. If you enjoy what we do here, the best way to support us is to become a premium subscriber atdesign better podcast.com subscribe. We'll return to the conversation after this quick break. Design Better is brought to you by WIX Studio, the platform built for all web creators to design, develop and manage exceptional web projects at scale. Learn more@wix.com studio and now back to the show.
C
Allison Rand, welcome to Design Better.
A
Thank you so much. I'm so happy to be here with you both.
C
Well, it's lovely to see you. We go way back to the envision days when we all worked together and we had a chance to see you and interact with you more often. So we miss you and it's great to have you back in our circle.
A
Yeah, it feels like such a perfect, comfortable space to kick all of this off with the two of you.
C
So you have a new book coming out. We're honored to be, I think, among the first folks that you're talking to about it. And it's both part memoir and part guide to being a leader in design and design ops. And it's a very personal story so not to get too, too personal at the start, but we're also kind of at a remembrance or milestone for September 11th just passed yesterday. And you mentioned in the book that was a very seminal part and shift in your career and the way you thought about life in general. Tell us what happened then and your experience around that time.
A
It was a wild time because I had just gotten back from an incredible trip where I spent a month in Greece. And I was sort of, like, floating on that experience. But I was also, for the first time, working as a freelancer. I remember waking up in the morning, the sky was like, the most perfect September blue sky. Every time I see the sky like that in September, I think of that. And I was listening to Howard Stern, which I loved to listen to at the time, and he was freaking out. And I was like, what is going on? And so then I turned on the television and I was like, you know, just completely shocked. It wasn't registering. And I was living in Brooklyn, in Fort Greene, where there's a park that is on a hill. And I couldn't get in touch with anybody, really, except my best friend Norma, who I talk about in the book, and my stepbrother, who was in the city. Norma was in Brooklyn. Jean, my stepbrother, was in the city. And somehow we got in touch with each other, and they both came to my house, and we walked to that hill. And in the process of walking to that hill, it's also part of Flatbush Avenue, where a lot of people were coming the Manhattan Bridge, where a lot of people were coming off soon, coming up Flatbush Avenue. And I had no idea where my husband was. I think at some point we got in touch, and I told him to go to another friend's house in Chelsea because he was working uptown. And I just spent the whole day with my brother and my best friend, just gutted. I grew up with those buildings. You know, my dad worked downtown. We ate at Windows on the World. They were the marker for, like, anybody navigating the city. And yet still to this day, seeing all the photos of it yesterday makes me feel so emotional. As soon as possible, I registered with the Red Cross and I did intake for missing people. And the juxtaposition of that experience is two days later, on September 13th, when I was doing the intake for people in a center, which was gut wrenching. I was, like, eating ridiculous things, you know, And I thought it was just comfort. I was, like, eating a thousand peanut butter and jelly sandwiches and Oreo cookies. And then the next day, I Found out I was pregnant, and my father was stuck in Europe and trying desperately to come back. And I think he came back right around that time. And I was. You know, I just. Like this moment of, like, all of this pain and suffering and absolute devastation. I mean, the city was destroyed. My home, my people. But then I was carrying life for the first time, which really, it's ironic because I feel like there's been many periods in my life where something has been so terrible and so wonderful at the same time. And I can't say that I felt hopeful after September 11th for everything, you know, for the city. But I really do still believe that my daughter Luna, now, who's 23, was a real ray of light through all of that.
B
Were there any philosophical revelations that came out of that experience for you? Being so close to death, being part of response and having life inside of you at the same time? Anything that sort of guides you day to day?
A
All of those things guide me day to day. I lost my mother when I was 16, and I talk about it in the book. And so death has always been been ever present in my life because it was foundational to my childhood. And in this experience, too, like, everything was terrible, you know, for a long, long, long period after that, of course, especially in New York. Couldn't find work, couldn't do anything. You know, everything smelled horrible, this wretched smell across the city. But I was carrying this child inside of me, and I felt so close to her. And so everything that I did to try to help. And I'm not trying to be like, oh, I'm some vessel, but I felt like there was purpose. There was a reason why I was pregnant and a reason why I was not working, which wasn't ideal, but also I was able to help. And so I think that those two things do really guide me. As humans, we often live in contradictory spaces. They're not always so, like, overt, like a terrorist attack and then, like, you find out you're pregnant. But we all go through incredibly difficult times. And, you know, I've been thinking about this a lot, and I said this in the last couple of days. Well, two things in Buddhism, there's this philosophy of, like, hopelessness is where things begin. And that's been something. I really strived to keep feeling that hopelessness during that time and also feeling so hopeful. And then the other thing, because also considering all the terrible news all the time, but particularly this week, is Martin Luther King's. Hate cannot drive out hate. Only love can do that. All of those things are how I try to show up in my life.
B
It's interesting. So your book, Cinto, the approach that you take to it is that it's part memoir and it's part guide, as Eli mentioned here. And this authenticity that's in the book, your personal stories are there. And since we've worked together and we have friends in common, John Maida, who's a multi time guest, I know a little bit about the perception of you from working with you, but also perception from other people who have worked with you. And there's a general sense of authenticity. And I know that's a word that gets a little overused, but it really is true about you, about how you bring your humanity into your work. Can you talk a little bit about the approach to the book, why your personal story is there and then how you think about that, you know, your professional life and your personal life and their relationship.
A
So the book, it's funny. I'll tell a quick story of the genesis of the book and it's in the book. I think it's in the prologue. I talk a little bit about how I was really frustrated at work. I have a very close group of friends that are family that I grew up with, all from New York. All are like multi ethnic, weird families that we just were so tight. Anyway, I was really frustrated at work and I jokingly sent a message in our group chat of like, I'm gonna write a book and it's gonna have these chapters. And it was all ridiculous things that we would say when we were growing up. I can't remember exactly what some of them were, but it was like, why is this guy hitting on me when we're not even in the club? Just this sort of like silliness around. Why does so much of my experiences feel like experiences I had when I was a kid? This navigating of spaces and places I had when I was like 14 or 8 were feeling so relevant in my current spaces. It just had different outfits on, you know, so they were like, you should write that book. And then I tweeted it and then the executive editor from MIT Press got back to me and he was like, if you want to write this book, we'd love to talk to you about it. Which I thought was part of the joke. I was like, this can't be serious. But as we started to talk more about it, I said to him, if you want me to write a book. Because I was definitely not interested in writing a book. But I was like, if you're interested in writing A book with me. I'm interested. But it has to be the story I want to tell. It has to be like that tweet, because I think the authentic word, it's a little like you said, it gets overused. And I think it can be good and bad. Right. Some people don't appreciate my authenticity and some people do. And so I wanted it to feel like me. I needed it to feel like my gritty Puerto Rican self that's grown into this space that is very different from riding the subways in the eighties in New York City and have those two meet. Because it made so much sense to me. You know, sentido, which means to make sense of. It's a multi layered word, has always been the thing that I could see commonalities in. It's like, oh, yeah, this feels exactly like this space. And then I recognize that all of the things that people say about me in terms of authenticity and what I bring is all of the things that I brought as a child, well before I was in spaces where we were talking about these buttoned up processes.
B
I think this is an important thing for listeners to hear because so many of us, we go to work and we feel like, okay, I'm going to put this cloak of professionalism on. I've certainly done that a lot of times. And it can be very powerful to have a boss who can be more vulnerable, a colleague who can be more vulnerable. Colleagues that you work with, that you feel like you can get to know them as human beings instead of like these transactional partners. How do you think about the connection between those?
A
I have multiple opinions about that. I'm not a huge fan of that. Bring your whole self to work. There's parts of it that are really important, but there's also parts of it that are just like over the top. And not everybody should bring them wholesale, you know what I'm saying? Like. Like some of it should be checked at the door.
C
I tried wearing a biking helmet once and it just didn't come across all that well.
A
Some things you just gotta. But when I was thinking about how important it is for us to be whole people when we're at work, I worked on this personal professional mission which helped people think about their strengths and their opportunities and their passions. The big part of this, like revised SWOT analysis was the passion piece, because I believe as a leader and as a human, like, if we think about the things we're passionate about in our personal lives or our professional lives, if you are able to find a way to bring that into your day to day, then you are bringing more of your quote unquote, authentic self. And also I think that it is very difficult for people, especially underrepresented, marginalized, whatever word you want to use to do that. We can't always bring our whole selves to work. My growth and maturity, professional maturity trajectory has been like. I realized that I got to this point where I think it was John Maida who said, the thing about you, Allison, is that when people hit, you hit back. And maybe you should think about that. I was like, that's the part of me that comes from New York and has been feeling like I needed to fight all the time. Not physically fight, but like fight for my space and fight for my place, defend myself. And so what did it mean to balance that part of me in a professional space? Because I didn't want to lose it. In the book, I think I have a section called like, how to professionally read a colleague. Because in the old days, old days, be like, I'm going to read you like, and like, I'm going to tell you, like everything I think about you and it's not going to be pretty. But if you're at work, that truth to me is important to share, but you need to share it in the right way. And I've often found that when you're truthful with kindness with people, and again to your point, you can also show up with vulnerability. It creates so much space for relationships to flourish and for so many other things to grow from that.
C
Alison, you mentioned the title of the book, Sentido, which I think is a lovely title. I speak some Spanish, enough to get by when I'm traveling in Spanish speaking countries. And I've always liked that word. And you mentioned it's multi layered. You know, it means sense or making sense. But there's also an aspect of feeling and it kind of feels like your book wraps those elements in as well. So maybe tell us why you chose that particular word as a title.
A
Yeah, I mean, I've always loved that word because of the complex layered nuance of it. In most languages, there are words that describe things that we would need so many more words to say in English or couldn't even articulate. So Sentiro to me is like, you can have a conversation with somebody that you're just saying, I feel also there's a la brega in Puerto Rico they use that. It means struggle. And also like, struggle is good. So you could be like, work was tough and the day was tough. La brega, la brega, or it's like, you know, you're really feeling like things are terrible and the lights are out, there's no power. And that's like the depths of struggle. So Sentiro to make sense of I feel as a child and having spent so many years in Puerto Rico with a Puerto Rican mother and having lost her, trying to make sense of the world felt impossible. But the fact that that word is so much about feeling. And I think I navigate the world with a lot of feeling, a lot of heart, for better or worse. You know, I'm a super sensitive person and I've always tried to make sense of things through feeling, but also through what is around me. So that's why I chose it. I think it's just a beautiful word that really encapsulates me.
B
You sort of alluded to this phrase, radical candor. You didn't say it, but this is a very popular term in the Silicon Valley set. And it's Kim Scott, who wrote a book about it and has done seminars and so forth, trying to get people to be more candid with one another, to give constructive feedback. I think a lot of times that is sort of like the get out of jail free card for assholes who just want to dump on you. You have this other approach, which is radical humanity. Tell us about your perspective on radical Radical Candor and just how you think about this in communicating with people at work.
A
Well, yeah, I think that there's evidence over time that Radical Candor became problematic, which I think she wrote another book to follow up as to, like, why that might be. I just have a lot of problems with these books written by people who haven't done the work of understanding other people's experiences. And so it's like that book Grit. I think that Radical Candor probably could have been. Well, it was a massive success and everybody loved it, right. That maybe it could have been better if more inputs were given to understand that not everybody can do that. Not everybody has the right to be radically candid. And also it's incredibly top down. That is not a bottoms up kind of thing. No one's going to go to their boss and be like, guess what, Like, I think you're an asshole or whatever. Like, I don't.
B
Like, I have some radical feedback for you.
C
Here's you're radically fired now.
A
So. Yeah, exactly. It's like, I think it actually perpetuates a culture of fear in some ways because there's the feedback fallacy too, where everyone's like, oh, feedback, feedback, feedback. But then all of A sudden you're getting all this feedback all the time. You don't know, like, what you should glean from that feedback because it doesn't feel thoughtful, where you're just moving through these prescribed processes. The radical humanity, which is different from the 2 by 4 I have in the book, which was just sort of a joke on radical candor. This two by four is very much aligned with what I feel is the, like, undercurrent of the experience for a lot of people in the whole radical candor quadrant thing, but also is kind of a fun way to talk about it and to relate to it in this sort of colloquial sense. So in the care personalita challenge directly, I think everyone was like, you're supposed to be on the top. Right. So for real, for real. I'm for real, for real. Being super, like, deadass honest. It's like, okay, you respect it or not. Unsolicited hot takes. You want to be starting something. So it's like no one asked you for that. And clearly it feels like you want to start a fight or like, it's just going to make me feel bad. Right. Bless your heart. Are you in the South, Aaron?
B
I think in Georgia I am, yeah. That is what people say here is bless your heart is how they say you're a knucklehead.
A
Exactly. I mean, I went to college in North Carolina, so I knew, bless your heart. So, yeah, you're a knucklehead. But it's so condescending. Right. And it's patronizing. For me, it's almost the upper left quadrant of all the fields, like, not your emotional labor. I know that also that's the other side of bring your whole self to work is like, let's just talk about all the things that I have problems with you and this whole, like, backlash to wokeism. But I do think that there's something in people being able to say, like, my job is not to do the work of your emotional labor or do the emotional labor work for you. So it was something I had fun with. And as a counterbalance to how I feel about radical candor, I like it.
C
It's a great framework. And I have to admit I never read the Kim Scott book, but I'm wondering if a few things maybe she left out of it. One is just building trust with someone before you maybe challenge them directly. Because if you don't know the person, you don't know how they think, you don't know how they react, you don't know their experiences. If you build that trust, then I think you have more of a chance to be open and honest. I think the other thing and we had on Sarah Seeger, who's a astrophysicist, several years ago, she was diagnosed pretty late in life with autism. She actually made herself like a little rule book for working with non autistic folks because for the way that she thinks challenging somebody directly from the get go is fine because she just wants to be direct. That's the most logical way to interact with somebody. But she actually had to write these rules to say no. You actually have to get to know somebody. There's small talk involved. You got to kind of warm up to something. So people are different, People don't think differently, their brains operate differently. And so I think this radical humanity, it sounds like it takes more of that into account.
A
Yeah, absolutely. I try to have a lot of compassion for the people that I work with. Even in frustrating circumstances. I think I've learned to use that like tactical empathy approach to say like, we know at the end of the day, everybody really cares about how it affects them. And because I do so much work in change management and all this like transformation, transformation, all of the work that I've been doing for years inherently makes people super nervous and uncomfortable. So I'm always the person that people don't wanna like, you know, the arbiter of change. But I have learned over time. Cause I definitely worked in spaces where I came in way too hot, you know, and wasn't doing enough listening and understanding that there is so much about knowing. If you understand that people really do care about how does this affect me, then it's easier to just start there, to build trust, even internally and even as a place to start conversations as groups of people or individuals or whatever. It is like so much of that work, you cannot do any of it if you don't start to build trust.
B
We'll return to the conversation after this quick break. Design Better is supported by Masterclass. Eli and I are lifelong learners. Both of us are always reading, expanding our skills and pursuing new interests. And I have a hunch, as a Design Better listener, you're probably the same. The best way to expand your knowledge is with Masterclass, which lets you learn from the best to become your best. Masterclass is the only streaming platform where you can learn from over 200 plus of the world's best, best and brightest people like David Sedaris, Ryan Holiday, Anna Wintour, Shonda Rhimes, Martin Scorsese and the late Jane Goodall. I learned a ton about Business strategy from Bob Iger's Masterclass. And Eli is a fan of Neil Gaiman's Masterclass on storytelling. Whether you want to learn to write, improve your public speaking, develop a mindfulness practice, enhance your creativity, or become a better cook, Masterclass has in depth expertise you can tap into anytime and any place. You can access Masterclass on your phone, your computer, your smart TV, or even in audio mode. You can just listen to the classes. Right now. Design Better listeners get an additional 15% off any annual membership@masterclass.com designbetter that's 15% off@masterclass.com designbetter and now back to the show. Your career is interesting. You've been a major influence on Design Ops and helping establish that space. You worked at Hot Studio, which if listeners have not heard of Hot Studio, designOps really kind of became a thing from Hot Studio, being ingested by Facebook, now Meta, and then it became kind of program management and so forth. So that was a progenitor of that discipline. You were at Frog Automatic, you were head of Design Ops there, who of course make WordPress, which is about 45% of the web is on WordPress these days. We mentioned earlier you worked with us at InVision and you worked at SAP. So if we were to look at your LinkedIn profile, we'd say like, hey, here's the this kind of movement through agencies into large corporations with lots of operations and organizational prowess, expertise. And then you went independent. What's the story behind that?
A
The story behind that is that I felt like I had reached the pinnacle of my career or what I had been working for when I was brought into SAP with the new Chief Design Officer at the time and spent years building out a team in a center of excellence. And then he left quickly, like within a year, and they brought somebody else in who wanted to bring in his own people and had his own ideas of things to do, et cetera. So it was a Friday that I received notice that I was awarded the contract to write this book. So. So I was feeling again, like high, high, you know, I felt like I had done all of this work to get to this place. And here I am writing a book for MIT Press. Like what? My mom would be beside herself. And then on Monday I got fired, laid off, whatever. My job was redundant, even though it wasn't. So I went into not a good place. You know, I was feeling so successful and so unsuccessful at the same time. And there were so many things that happened through that experience that were unaccept, like not okay I've experienced them so many times. But then again, it's like, is it me? This keeps happening. I don't know. Just so much self doubt. And so I needed to take a step back, which is why, in part, I also left New York City after a lifetime there and moved into the woods and decided to be independent because two things. I needed to write the book from that place that I was at, which actually in a lot of ways is a gift. Because I feel like I was able to write the book that I'm proud of, more so than what I would have written before, which might have just been more of an expected academic approach to operations strategy design. I don't know. But this book just came with so much heart. I think because I was so mired in my own personal work of feeling like my professional life had kind of imploded or exploded. Working independently allows me to come as me. I don't have to play any games really. You know, like, I have to get the work. But oftentimes they come to me because they're looking for me and how I do the work, and then I can choose whether or not I want to do it with them. And so it's been a real evolution of trying to figure out where I want to go next. I was just working on an article and I was thinking about how I think design operations needs a rebrand. It went from like, you know, like everyone was like, design ops. Design ops, design ops. And I still fully believe in it. I just think that it should just be so integrated into the broader environment of this work in the way that everything's changing so much right now. Engineers are getting laid off. But are designers gonna become even more relevant? I'd like to think so. And so I think that design operations, it's change management, it is human centered, and it is a process that is heart centered. And that's the difference because it is design process. Design is also design. But the work that we do is so people centered. It's so human centered in that we really need to do all the things we've been talking about, like gain trust, have compassion, have more understanding, you know, go through the design processes. In my book, it's a different take on this, like, wander, test, explore, emerge. Because I think it leads with so much more curiosity and people are at the heart of it. When I have been building my practices, my last practice at SAP, there was culture and practice and service and enablement. They were two sides of that same coin. That was under strategic operations in the design center of Excellence and the culture and practice part was equally as important as service and enablement, because it was about like, the designer was our customer and their experience. And so what are we doing to ensure that they are feeling supported as people, not just like traditional hr. It's very different. And then infused in that process, which is horizontal, is the enablement and the service. And I heard somebody, I think it was Rachel Deacas, recently wrote something about we should shift the language from communities of practice to communities of service. I really love that lens because the way I've always approached this work is that it is a service organization, but also like servant leadership. Service part. It was never really that popular in organizations for, from my experience, not popular at all. Design ops could never really articulate why we're there. And you would always get the smallest budgets and have the smallest teams and be expected to do so much work. But I believe that all of this work should just be naturally infused into organizations. So it really depends on the people who are leading it. But if you just partition it off, it's not necessarily as impactful.
C
I'm curious a bit about your rainforest metaphor. In the book, you talk about the El Yunque Rape Forest and spending time there. I believe you were a kid in Puerto Rico, is that right? Yeah, I visited my first rainforest in Costa Rica back in the early 2000s, and it just blew me away how much life there was there. Everything is living, everything is lush, there's bird life, reptile life everywhere you look. It's just amazing. The closest thing that I'd seen before that was I'd spent time diving in coral reefs. And there's a similar sense. It's like just explosion of life and ecosystems and these intricate relationships. So tell us a little bit about why you use that metaphor and maybe some of the things like the mutualism and symbiotic relationships that you can kind of relate to workplace culture.
A
I think a lot about living systems in relation to organizations as like organisms of living systems, different but in nature. When you go to these places, I go back to Puerto Rico once or twice a year and I always go to El Yunque. And even after Hurricane Maria, the depth station from Hurricane Maria, if you see the pictures, the rainforest didn't exist anymore. It was gone, completely gone. But it regenerated so quickly. The layers of those forests, I think, have an illustration in the book around layers of living systems. The interdependence of all of it to actually thrive is essential, of course. And the mutualism part is that interdependence we are, because you are. Even in how the trees communicate in their root systems and how every layer of the forest is protecting another layer of the forest, like it's really working together. And then of course, there's the outside things that come in that weren't supposed to be. They're invasive species, and they either work around it or it destroys things. And so I feel like it's so analogous to how we could approach how we work and how we think about our organizations and how we think about just us, society in general. When I was half joking about, like, I'm in my rewilding phase now, because I actually think I am, is because we're so removed from it. And I don't even mean as urban dwellers. I think that we try to remove so much of it. And when you see spaces like, I'm selling my house in Brooklyn now and haven't been there in a while, but somebody took a picture of the backyard and it had been completely taken over by everything that wants to take it over, everything that you try to get rid of. But it all just comes back so strong. In thinking about El Yunques, I'll say specifically, I think about how there's such a beautiful metaphor for coexistence and this mutualistic relationships, it's incredible to see. And how at the same time, something can be so entirely devastated but find its way back to the same. But probably an evolved space, maybe, because maybe it's learned. I don't know, probably. And then the invasive species part is also real. So to me, there's just like direct correlation to how we could. And maybe I'm just being like, way too kumbaya about it all. But I do think the complexity in that thinking is really important for me to apply to my work and say, like, okay, when I take a step back and join an organization or somebody's asking me to look at something, like, what are all the different facets of how this organization is functioning? Is it functioning in silos? Are they saying they're collaborative? Are there just like totally different factions? Is this a garbage can model? Trying to understand from that highest level of what is happening and then begin. And people talk a lot about design systems being a really good place to sort of start that connection point. I get it. I think it can be true because if you have a foundation of which everybody can kind of connect to, they can sort of understand things better and they can move faster and all of those things. But I do think that it's a really important and difficult to help people Understand through my work or through this work, it shouldn't ever be, this is my space, this is my territory, blah, blah, blah, blah. Because if you're working in an organization like at SAP or Envision, whatever, we're all on this ship together. So how can we leverage one another rather than feel threatened by it? To evolve and learn, like, I'll say. Frog was by far the best place I ever worked. I loved it so much and I wouldn't have left if I was ready. It was time, you know, and also I was going to work with John at Automatic, so it felt like the right time. But the amazing thing was that everyone was so different and it felt like a incubator for talent. However, we would put all these different people together and different. And that was my job, is like to identify the different people who needed to solve this problem. And we would all be together in these spaces and we would always leverage each other and each other's skills and learn and grow from each other. And that I did not see enough of when I worked on the inside. It's incredibly powerful to know that all of these different pieces can function together and something beautiful can emerge. So what does it take to do the work to allow that to flourish?
B
Can you articulate that? Because, you know, I can think of various places that I have worked and sometimes the culture doesn't really facilitate that. What are the things that are required and what's the kryptonite to that sort of exchange and support that you just described in a company culture?
A
That's a really difficult question to answer because it's not a one size fits all model. So much of it depends on the culture you're coming into. And there are plenty of times where there is massive org rejection for this type of, of work, like organ rejection. You know, you have to really understand the DNA of the company. Smaller companies, in even bigger companies, so much of that stems from the founder or the culture in which it's grown. You know, like working at SAP a year in, I realized I don't understand German culture. I feel like I'm hitting all these walls because I'm this Latina who like talks like, blah, blah, blah, blah, blah, blah. It's very different from German culture. And so then I started to realize I need to understand this is a German company, it's built in German culture. Like, this is how they function. It's clearer that we're going to have friction points. So it's difficult question to answer because every space is so different. You have to look for Is the soil ripe? Oftentimes you can't figure that out unless you throw a bunch of seeds out there and see what actually takes root. I've been in plenty of positions where I've been led to believe the soil is ripe, but it actually isn't. And so if you can find a way to really understand if there's support from the top, the bottom, and the middle, there's always the base of people who are like, yeah, you're amazing. I'm so excited you're here. But does the top level really believe in the work? And then trying to understand that middle part, what's the taxonomy of the skeptics who are all the people who are going to be in friction with you? Because those people are probably more important. Just to understand. Part of the reason why I also just went back into consulting or working for myself is I like to work in spaces where it feels a little bit riper.
B
I liked what you had to say about intelligence versus street smarts in the book, and I wonder if you could just share with us what your observation is about the two.
A
Yes, that is the core thesis of Sentido is the argument I'm trying to make about organic intelligence versus traditional academia. I come from a family where I was the first woman to graduate from college. You know, my mom didn't go to college. It was the big thing, you know, and I didn't get that much out of it. What I got out of it was going to school in the south and having experiences that I never had when I was growing up in New York. All of a sudden I was like, wow, racism is real. And God forbid you tell anybody you're Jewish. Like, I knew to never say that. And it was more almost this, like, sociological experience for me than feeling like I gained a lot academically. But then I went into spaces where academia was so revered, and I was glad that I went to college and I was able to at least have boom. But it was never enough, you know, Like, I didn't have a master's, I didn't have a PhD. I wasn't doing this. It always felt like it wasn't enough. But then I felt like I wasn't enough. You know, in the book I write about, some of the people who have taught me the most are non traditional thinkers. Like, you know, my best friend Norma, who got her ged. And I think she's one of the smartest people I know, hands down. I mean, we're still besties. And she's taught me from the time I was A child to today about so many different things and so many ways of thinking about things. And I'm sure you have people in your life like that too. And then I had my stepfather who went to City College and is also just a total, incredibly sage human being who gifted me with so much and still does. And I think Obama, I saw Obama saying something like this or whatever, like where he was like, you get to the highest, highest, highest tables and you're like, did you really say that? Did you really say that? Oh, my God. I thought these people were gonna be like wicked smart. So I found myself in these spaces where everybody was touting all of their academic accolades and I didn't find them to be what I considered intelligent. And so this organic intelligence versus academic intelligence. I'm not fighting against academia. I'm just saying that I believe that so much of what we have, if we really look and leverage it, has been baked into us before we go to college or through other experiences, through lived experiences. My oldest daughter, Luna, who is the illustrator in the book, she dropped out of college and she's an artist and she's kind of a polymath. She's scientist and an artist, and it wasn't doing anything for her. And from my own personal journey, I was like, I just wrote this whole book about this and here's happening to me, right? I'm like kind of struggling with it, you know, this feeling like you need, especially as a woman to have this stamp that you're educated. But I also don't believe it, especially right now.
C
Yeah, you know, I spent the last decade plus with part of my career in academia, and I think our program is lucky in that most of the people that teach are actually also practitioners. So we're teaching students, but we're also doing work in the real world. And I think that there's a lot of advantage to that. In fact, David Kelly, who we're celebrating like his 50 year anniversary at Stanford coming up in a few weeks, he's, I think, the only tenured professor at Stanford that does not have a PhD. And the same is true of my old design professor, Matt Kahn, who didn't even graduate from college and taught there for like 60 years. So maybe there's something about design or product design that gives space to folks who want to teach but also have the real experience.
A
And I also just want to add one last thing, is that I think that we've just so deeply undervalued, especially now that I live out here by seaside where everyone sends their kids to Technical schools, and they want them to be fishermen and plumbers and electricians. They're all super psyched about that. I think that we've just undervalued city colleges, community colleges, technical spaces. The way that the ivory tower of our world, academic world, has looked down on that is really. I hope it changes.
C
Well, Alison, what right now is inspiring you? And it doesn't have to be anything work related, but is there anything that you're watching or reading or podcasts you're listening to? Anything along those lines that you're finding bringing you joy or inspiring you?
A
Yeah. Oh my gosh, so much I find myself in this point and like, I'm in midlife and I have insatiable curiosity and I just want to take things in. I started a master's in Strategic Foresight at University of Houston, which has been really fun. And I chose that because I have curiosity for so many things and I feel like I can apply it to so many different things. I've been spending the last couple of years building a platform for women's health, Women in Midlife, 4050, which I have such tremendous passion for around emotion and fact and information and story. Somebody said this to me the other day in my community group. The intimacy economy that really resonates with me, especially in the space I'm trying to build and focus on is spending more time together in more meaningful ways and what that might look like. And I've also started in the last, like year or two doing a lot of sculpting with beeswax and been trying to use a natural material. Cause I was so inspired by all the living systems around me. Just got like a crock pot and a bunch of beeswax and I've been making things and it's been really nice to work with my hands again.
C
Well, Allison, where can folks find your book?
A
Anywhere where books are sold. If you go to MIT Press in Santido, you will find all the different places that sell it. But I like to push people to bookshop since you can buy from your local bookstores. But of course it's an Amazon and Barnes and Noble and all of the places that you would expect it to be. But try and buy from a local bookstore if you can.
B
And you mentioned 40, 50. I just wanted to point out that URL too, because I think that work is really important. 4050CO, right?
A
Yes, 4050CO. And yeah, we have three different parts of that going on right now. A community space that just launched, which is great. A substack I've been running for the last couple of years, which is just my writing and women's stories and the opportunity to submit your own story.
C
That's great.
B
Alison Rand, Such a treat to see you. Thanks for being on the show.
A
Yes, you too. Thank you so much.
B
This episode was produced by Eli Woolery and me, Aaron Walter, with engineering and production support from Brian Paik of Pacific Audio. If you found this episode useful, we hope that you'll leave us a review on Apple Podcasts, Spotify, or wherever you listen to finer shows. Or simply drop a link to the show in your Team Slack Channel designbetterpodcast. Com. It'll really help others discover the show. Until next time.
Date: October 21, 2025
Hosts: Eli Woolery & Aarron Walter (The Curiosity Department)
Guest: Alison Rand
Episode Theme: Exploring leadership in design through the lens of "radical humanity," drawing from Alison Rand's personal journey, her landmark role in Design Operations (DesignOps), and the philosophies underpinning her new book, Sentido.
In this episode, co-hosts Eli Woolery and Aarron Walter engage with Alison Rand—pioneering DesignOps leader and author—to discuss her alternative to Silicon Valley’s ethos of “radical candor”: the practice of “radical humanity.” Rand shares personal stories from 9/11, her multicultural upbringing, and her experiences at the forefront of DesignOps in organizations ranging from Hot Studio to SAP, Frog, and Automatic. Centering her philosophy on empathy, systemic change, and mutual growth, Rand introduces frameworks from her new book Sentido, drawing parallels between living ecosystems and modern organizations.
[03:27 – 08:29]
Alison recounts the emotional chaos following 9/11: returning from Greece, the collapse of the towers, and supporting friends and family while volunteering with the Red Cross.
The profound juxtaposition of personal loss, city-wide trauma, and discovering she was pregnant shaped her core philosophy: life’s constant contradictions and the ever-present dance between hope and despair.
Quote:
“I felt like there was purpose. There was a reason why I was pregnant and a reason why I was not working… As humans, we often live in contradictory spaces.”
— Alison Rand [06:45]
MLK and Buddhist philosophies anchor her approach to adversity—transforming hopelessness into a starting point for renewal.
[08:29 – 11:42]
“I needed it to feel like my gritty Puerto Rican self that's grown into this space that is very different from riding the subways in the eighties in New York City.”
— Alison Rand [09:19]
[11:42 – 14:55]
Alison is skeptical of the corporate “bring your whole self to work” mantra: some personal boundaries are healthy and necessary.
The real value, she argues, comes from connecting personal passions to work and balancing open-heartedness with professionalism and context—especially for marginalized individuals.
Humorous Interlude:
“I tried wearing a biking helmet once and it just didn't come across all that well.”
— Eli Woolery [12:31]
Her professional maturity journey was about transforming the instinct to “hit back” into honest, kind truth-sharing that nurtures relationships.
[14:55 – 16:44]
[16:44 – 22:59]
Alison critiques the “radical candor” model for being too top-down, inflexible, and insensitive to power dynamics and individual backgrounds.
“Radical humanity,” her counter-framework, stresses compassion, mutualism, and the context-dependent nature of feedback:
Quotes:
“Not everybody has the right to be radically candid. And also it's incredibly top down. That is not a bottoms up kind of thing.”
— Alison Rand [17:24]
“I try to have a lot of compassion for the people that I work with. Even in frustrating circumstances. ... There is so much about knowing [that] people really do care about how does this affect me.”
— Alison Rand [21:41]
Building trust is essential before direct challenges or feedback; organizational change relies on trust, empathy, and an understanding of diverse modes of communication.
[25:43 – 30:48]
Career journey from Hot Studio (birthplace of modern DesignOps) through Frog, Automatic (WordPress), InVision, and SAP.
The transformative (and sometimes painful) experience of being laid off at the peak of her professional success led her toward independence and writing.
Independent work has empowered Alison to be “fully herself” in her consulting and creative projects.
The future of DesignOps lies in integrating operational thinking into organizational DNA, emphasizing heart-centered processes and human-centric change, rather than relegating it to a side function.
Quote:
“Design operations, it's change management, it is human centered, and it is a process that is heart centered. And that's the difference because it is design process. … The designer was our customer and their experience.”
— Alison Rand [25:43]
Moves toward “communities of service” rather than just “communities of practice.”
[30:48 – 36:04]
Drawing from experiences in El Yunque rainforest (Puerto Rico), Alison likens organizational health to ecosystems—mutualistic, layered, self-regenerating.
The interdependence found in rainforests serves as a metaphor for leadership, collaboration, and resilience in organizations.
Quote:
“Even after Hurricane Maria…the rainforest didn't exist anymore. But it regenerated so quickly…The interdependence of all of it to actually thrive is essential, of course. And the mutualism part is that interdependence—we are, because you are.”
— Alison Rand [31:30]
Invasive species represent destructive ego or toxic influences; healthy cultures require ongoing adaptation, foundation-building (design systems), and collective evolution.
Alison’s time at Frog is cited as a model for leveraging diversity and mutualistic creativity.
[36:04 – 38:23]
[38:23 – 42:20]
Central argument of Sentido: Organic (street) smarts are as valuable, if not more, than formal credentials, especially in design.
Alison shares personal reflections as a first-generation college graduate and the value of lived experience vs. academic accolades.
Quotes:
“I didn't have a master's, I didn't have a PhD. … But then I felt like I wasn't enough. … Some of the people who have taught me the most are non traditional thinkers.”
— Alison Rand [38:32]
The undervaluing of technical, community, and city colleges is critiqued.
[43:01 – 44:15]
“I just want to take things in… The intimacy economy… spending more time together in more meaningful ways and what that might look like.”
— Alison Rand [43:01]
This enriching conversation unpacks the value of leading with empathy, context, and lived experience—over prescriptive management tactics. Alison Rand’s vision for leadership and organizational design is rooted in complex humanity, resilience, and system thinking. Sentido isn’t just a manual for DesignOps or creative leadership—it’s a call for heart-driven change in work and beyond.