Alison Rand: Leading with radical humanity instead of radical candor

0:01Everything'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.

0:23I'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. Allison 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, Sintido. It's a term that encompasses both making sense of things and feeling them deeply.

1:05In our conversation, Allison 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. This is Design Better, where we explore creativity at the intersection of design and technology. I'm Eli Wildery. And I'm Aaron Walter. At Design Better, 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.

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2:02We'll return to the conversation after this quick break.

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3:03And now, back to the show.

3:10Allison Rand, welcome to Design Better. Thank you so much. I'm so happy to be here with you both. Well, it's lovely to see you. We go way back to the Envision days when we all worked together, and we had the 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. Yeah, it feels like such a perfect, comfortable space to kick all of this off with the two of you. 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.

3:43And it's a very personal story. So not to get too, too personal to 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. 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.

4:24The 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.

5:02Gene, 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 is where a lot of people were coming off, so 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.

5:42You know, my dad worked downtown. We ate at Windows on the World. They were the marker for, like, anybody navigating the city. And, yeah, 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.

6:20And 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 like 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.

6:59But I really do still believe that my daughter, Luna, now who's 23, was a real ray of light through all of that. Were there any philosophical revelations that came out of that experience for you, being so close to death, being part of a response and having life inside of you at the same time? Anything that sort of guides you day to day? 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 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.

7:45Couldn'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 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're pregnant.

8:28But 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.

9:07It's interesting. So your book, Sintido, 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.

9:46Can 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? 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. But anyway, I was really frustrated at work, and I jokingly sent a message in our group chat of like, I'm going to write a book, and it's going to have these chapters.

10:23And 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? And 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.

11:05I 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 80s in New York City.

11:51And have those two meet because it made so much sense to me. You know, sentido, which means to make sense of, it's a multilayered word, has always been the thing that I could see commonalities in. And 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. 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.

12:31I'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? I have multiple opinions about that. I'm not a huge fan of that bring your whole self to work thing. 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?

13:07Like some of it should be checked at the door. I tried wearing a biking helmet once and it just didn't come across all that well. Some things you just got to.

13:21But 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.

14:14We can't always bring our whole selves to work. My growth in 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.

14:55In the book, I think I have a section called like how to professionally read a colleague. Because in the old days, old days, the old days, I'd be like, I'm going to read you. And I'm going to tell you 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.

15:34Allison, 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 multilayered, 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. 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.

16:11So sentido 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 sentido, 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.

16:52But 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. 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.

17:43I 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 candor and just how you think about this in communicating with people at work. 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.

18:21And 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. Like, I don't like... I have some radical feedback for you. Yeah, here's a radical feedback. You're radically fired now.

19:03Yeah, exactly. I think it actually perpetuates a culture of fear in some ways because there's the feedback fallacy too, where everyone was like, oh, feedback, feedback, feedback. But then all of a sudden you're getting all this feedback all the time. You don't know 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 2x4 I have in the book, which was just sort of a joke on radical candor. This 2x4 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.

19:48but 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 personally to 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 dead ass honest. It's like, okay, you can 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? I'm in Georgia.

20:27I am, yeah. That is what people say here is bless your heart is how they say you're a knucklehead. 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.

21:12So it was something I had fun with and as a counterbalance to how I feel about radical candor. I like it. 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've built that trust, then I think you have more of a chance to be open and honest. And I think the other thing, and we had on Sarah Seeger, who's an astrophysicist several years ago, she was diagnosed pretty late in life with autism.

21:50She 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 know, 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.

22:20Yeah, 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 want to like, you know, the arbiter of change. but I have learned over time because 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.

23:38We'll return to the conversation after this quick break.

23:45If you've ever felt like the hardest part of being a leader isn't the work itself, but actually getting everyone to work together, well, we've got something coming up for you. Eli and I have partnered with our friends at September Works on the September Workshop Leadership Excursion. It's a two-day gathering in Sonoma on September 28th and 29th. And let me set the scene. This is wine country at its most beautiful, rolling hills, golden light, the kind of place where you can finally hear yourself think and walk away genuinely inspired. The format is intimate by design. Just 40 leaders are going to be there.