Jasmine Friedl, Senior Design Director at Dropbox, talks to Maze about how to build high-performing teams and cultures where people can succeed and achieve the best results for themselves, the business, and the customers.
The Optimal Path is a podcast about product decision-making from the team at Maze. Each episode brings in a product expert and looks at the stories, ideas, and frameworks they use to achieve better product decision-making—and how you can do the same.
You can connect with Jasmine on Twitter (@jazzy33ca) or check out her website.
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Ash Oliver:
Welcome to The Optimal Path, a podcast about product decision-making brought to you by Maze. I'm your host, Ash Oliver, UX Designer & Design Advocate. Great products are the result of great decisions, decisions that deliver value for customers and the organization. In this podcast, you'll hear from designers, product managers, and researchers about the ideas informing decision-making across all aspects of product development.
Today, I'm joined by Jasmine Friedl. Jasmine has been a senior design leader at Dropbox, Intercom, Udacity, Chan Zuckerberg Initiative, and Facebook. She's currently reading Atomic Habits and Why We Sleep, designing and sewing her own clothes, studying neurodivergence in adult women, baking cakes, and hanging out with her two French bulldogs, Bacon and Meatloaf. A personal design idol and keeper of my all-time favorite bio. Jasmine, thanks so much for being here.
Jasmine Friedl:
Favorite bio, huh? That's pretty cool.
Ash Oliver:
It is actually pretty tempting to just spend the episode talking about the non-design things that you're up to, but I've been really looking forward to our conversation. Our topic is around constructing teams for cultures and products that thrive, which is a pretty big subject, and there's so much that I could ask you about. But it actually struck me while I was preparing for this discussion that there might be an approach here that could ground the conversation and maybe give us a little bit of navigation into some of the core areas of the topic. It's a bit of a metaphor, and it's cake.
Jasmine Friedl:
Oh my gosh. Let's talk about cake. Yes, please.
Ash Oliver:
Oh, yeah, I was thinking maybe we could move through this a little bit like baking, so maybe breaking down building teams and cultures like baking a cake. We've got the ingredients, or the people, talent, culture, maybe as our first topic area, and then maybe the instructions and assembly process. Maybe we can get into some of the systems and processing things in there.
Jasmine Friedl:
Okay, I dig it. I dig it. I mean, who doesn't want to talk about cake, am I right?
Ash Oliver:
Maybe you could talk about some of the ingredients first, as a design leader, what are some of the elements that need to be involved on the people and culture level that make some of the hallmark cakes?
Jasmine Friedl:
Yeah. If I take the baking and the cooking thing, it's like when you're thinking of ideal outcomes in design, it's products that have business results that are great and customer results, both of those things usually have to be in conjunction. That's the finished cake. If we take it back to the ingredients, it's like you get to pick the precise things, or you have to work with what you have. I think the first question is, what do you start with? Thinking about people and teams, do you have the right people? And that could be quantity of people, or it could be types of specialties. Do they have the right skills? Do they have the support, the mentorship? Are they engaged? Do they have the environments that they need to be able to be successful, not just for themselves, but for the business, for the customers?
Do they have the strategy? Do they know which way they're going? Do they know what their goals are? Dropbox had such a wonderful structure for thinking about everything that every practitioner should be in terms of, like, do they drive results? Are they able to set direction? Do they contribute to culture? Do they have a growth mindset? Do they have specific craft skills? Those, to me, are all the ingredients that come together not only to a design team but to an R&D team in order to drive results.
Ash Oliver:
You've had a direct hand in a lot of these things. Can you tell me a little bit about your approach when you did that at Dropbox? What did you assess first?
Jasmine Friedl:
I think this is where the interesting piece comes in. It's rare that you get the full ingredients of the cake, and you're just putting them together, and they're all there. There's usually something that you have to do. In my experiences, I think of actually Intercom, where I came in and I was a smaller team and I had a handful of designers, and one by one, they just made the personal decisions to move on, and they were the right decisions. Everyone that I followed has a great career path and is very happy, and that's all I want for them. But I actually did have to start from zero. It's also rare. It's rare that you start with the cake, but it's also rare that you start with nothing. Most are in the middle, which is where Dropbox was for me, where there were a lot of teammates there and there was organizational structure there.
Just generally, in either situation, I think the things that I tend to assess are we always have to start with the business. We want to be a successful business. Sometimes the business comes before customers, sometimes customers come before the business, but they're inextricably linked. The first thing I usually say for people at least is like, are they aligned with that? Are they aligned with the business goals? Are they aligned with the customer's goals? Because if they're not, that doesn't mean that they're not good people or they're not great designers, but they're probably not the most impactful lever that I could use, but they probably could be impactful somewhere else. When you come into a company, it's just like, let's get a sense of who's really motivated here, who's really impactful here? I think that people thing is a really important analysis.
When I was at Intercom, I co-led the design team with Emmet Connolly, and he's just a fantastic design leader. And we had so much fun building up the team, and we talked about it like our bus, like, "We have the right people on the bus. We might not have everything we need in terms of what we know and what we don't know or what tools we have, but we know that at least we have the team that's going to go together there." There's just a wonderful sense of camaraderie that we had and that I think you need to have, too. It's not just about individuals. You might look at the individuals and say, "Hey, do you have the right people, the right skills, the right mindsets, the right motivation?" And then you actually have to step back and say, "Now, together, what does this give you?"
When I came to Dropbox, we had a reorg within a month that I was there, and I went to my boss, and I mean credit where credit's due, Alastair Simpson, and I asked, "How in this case do you evaluate? How do you make these decisions?" I was such a people-focused leader, and I had this principle of people before product, and he was like, "Well, you can't make decisions based on people. At a big company like this, you have to first set the strategy, you have to design the org around that, and then you have to put the people in the org."
The thing that we learned I think together was then there's that check back to say, "Okay, it's a sort of cascading thing. It's like strategy, org, people." But then, if people are on the bottom, you actually have to go back and say, "Okay, is this person going to be effective in this org? Is this person going to be happy in this org?" Then, "Is this org going to deliver on the strategy?" I found that to be a really powerful sort of checks and balances, where I don't say people before product anymore because I think that's incorrect. This is about the business and this is how we're going to get outcomes, and we're going to set that strategy and we're going to get the right people.
Sometimes, things do change. Sometimes you get rid of entire departments. Sometimes you need to grow things. Sometimes you need new leaders and you enable people to step up into bigger stretch roles. But if you shape around people, you may not get the results that you need. And that was something that poked at my soul a little bit, where I was like, "Oh, if I identify as a people-focused leader, how do I get on board with that?" But it goes back to what I learned at Intercom—if you truly do really care about your people and want the best for them and want them to succeed, sometimes those things don't match up. But then it's just about culture. It's like, do you approach that with honesty? Do you approach that with care? That's the people part. It's not about just giving them what they want. It's about being honest and saying, "Here is what you're going to get. Here's what I can give you. Here's what you may learn, and tell me how you feel about this." And listening.
Ash Oliver:
I want to touch on that framework that you mentioned, the cascading from strategy to org to people, and how this goes up the ladder and down the ladder in that way. I'm thinking, how do you assess individuals for the strategy?
Jasmine Friedl:
When I worked at Intercom, I had two spaces that I was leading. I was leading growth, which is a certain kind of an environment and necessity for the business at the stage Intercom was at—I think we were like 600 people at the time—and then I was leading Messenger, which is sort of their keystone product. Growth is really about B2B, selling to small and medium-sized businesses. Then Messenger is really B2B2C. There's different needs for those things. When I hired a manager for growth and when I hired ICs for the growth team, I really needed people who were interested in small levers. How can we tinker? How can we hypothesize? What's the world of possible? How can we really get to know the customer, deeply get into customer's needs?
Then, before I get to the people, if I think about org, I have to think about what kind of research do we need to get to know the customer? What sort of clarity do we need through content? What kinds of skills do these designers have? If they're huge, big picture, visionary, complex systems, that might not be the right sort of approach or the right sort of skillset. I would say, historically, at least earlier, in the past decade, it's really hard to hire growth people because growth was considered like growth hacking. A lot of designers just weren't motivated by that sort of thing.
I actually hired somebody for growth who really didn't want to do growth, and I just had to tell her, "Hey, this is what it is. The work might not be exactly what you want, but you're going to work on the most amazing team. You're going to work with the best PM. You're going to learn about growing a business, and that is going to be scalable." She signed on, and I actually asked her later if she wanted to move to the flashier Messenger thing, and she said no because she was loving it so much.
Then on the Messenger side, I need somebody who has excellent interaction design and visual design. Identifying the type of work and then saying, "what org do I need?" and then, "what people do I need?" I think, for me, it's going in and saying, "what is the strategy?" I've talked about strategy before actually in one of our New Layer Podcasts, but it's like, what is strategy? It's sort of just the plan. So, what is the plan for the growth team? If the plan for the growth team is experimentation, let's set up that environment, let's set up that culture, let's hire those people. It starts with, "what do we need to achieve? How are we going to do that with an organization? Can I hire the right person where they together are going to become multipliers?"
Ash Oliver:
I really love this example. It also connects to what you were describing with the bus and being honest about the route and where you're headed.
Jasmine Friedl:
One of the most beautiful things at Intercom, one of the things we did that really helped us get to a high-performing organization, was the designers, the product managers, the engineering managers, and our research and content folks all came together, and we did this workshop where we basically said, "What is San Francisco's purpose? What are we here for?" And this really beautiful thing came out of this, where we talked about making ourselves the brightest, smartest, wittiest versions of ourselves, and we make it so we want to come to work every Monday morning or every morning.
We had the most humble group of people, and that was probably actually a criterion for bringing somebody on. Wherever the arrow needed to point, they would say, "Let's get on board." I think that's just such a huge piece of culture. The strategy was there, and then the team was able to shift together. That way, when org changes happened, it was like everybody had a deep desire to contribute to that. That's the kind of camaraderie that starts in the values and the core of the business. And that comes from executives on down.
But it's also then how does that translate to attributes of an org? How does that translate to process and how we work? How does that translate to principles and how we make our decisions? And then people are just the activators of those things. If you get people who believe in the org, believe in the strategy, believe in all those things that culturally craft that strategy and org, then everything that happens in a business—the things that challenge our agility, the things that when we have to take pivots and take directions—when all those changes happen and all that chaos comes, the kinds of teams that I'm talking about are really able to just weather it.
Ash Oliver:
A lot of what you're talking about here is in the bigger values, the bigger principles. Are there any standout principles or values that have helped you navigate the culture in a certain direction or how it's shaped overall?
Jasmine Friedl:
I talk about Intercom because it was a rare and magical experience, and they just still have my heart. I've worked in tons of other environments, too. I think when we're talking about at scale, Dropbox is relative scale. Facebook, I saw it go through incredible scale, 10X scale. I think principles to me are more how you make decisions, but values are who you are, your core beliefs. And you end up being attracted to people in organizations that have the same beliefs. Mine tend to be things like openness. I think about the availability of information. For me, that's really important because my brain works in a way that I need lots of context and lots of information. But my question is, how easy is it to access and how easily do I enable people who work with me to access information? That could be about strategy, it could be about org, but it also could be about people.
The thing I've learned at Dropbox is, really, when you have a big organization leading at scale, there are some things that should not be accessible. If we're doing executive strategy planning, if I leak a bit of that to a teammate in the spirit of openness, that actually can be really destructive if they interpret that as, "There's going to be an org change," or "Wow, I don't see me in that, so therefore the work I do isn't valuable." I have to now interpret my value of openness and say, "Okay, what does that mean at scale?"
Another one is just care and kindness. I do want to think about people as humans. That goes back to the first things we were talking about, how you're honest with people and how you are open with people. I think about lightheartedness, just the idea that we can make fun of ourselves or joke around and be authentic and silly. Another one I think about, too, is forward thinking. How do we create a culture that, when stuff goes wrong, we're able to pick our heads up? Or when we're working on something right now and we want it to be different, how do we track the path to the next version? Those are the kinds of things I want to bring in.
I've developed those from bringing in the wrong things. I've developed those from first looking inward at what I need. Now I tend to look more outward at what the people around me need and the environments and cultures and companies need or might be missing. When you go into an organization and you see what's happening, the first question I ask is, "What is missing?" It could be the opposite of something that's there. Let's say it's too intense and people are burned out. Where is the lightheartedness? Or it could be just the absence of something. When I go in and I see a homogenous design team, how do we change that value and say diversity gives us different approaches, it gives us different experiences, it helps us build better products?
Ash Oliver:
Yeah. That is really interesting. I'm thinking about how this moves into the processes or rituals or the action behind the decisions that get made.
Jasmine Friedl:
It makes me think about roles and responsibilities. When you're building a strategy, that's what we need to get to and how we're going to get there. It also should be what we're not going to do. Then the people are who's going to do what at X level? Who's going to cover for what? Who's going to do the thing that's missing? That goes back to the people thing. It's like, how do I know that my product partner wants to do this? I build a relationship with them. I get to know them. I pay attention to them.
My product partner right now is phenomenal. He is a business person, and so anything, tracking metrics, like, I just let him drive that. He's not a visionary. I drive that. When something comes up, I'm also watching him and saying, "How busy is he? How hard is it for me to get time with him? What's his mood like?" When there are things that I see that I'm like, "I can take that," I'll just say, "I can take that," because I am so connected to him. So, how do you get the pulse of the people around you in order to figure out how to do the tactical things?
Another prioritization framework that I also learned from Alastair was: Do, Delegate, Defer, Delete. So, I think all the things that come in are just how do you respond? That's part of the responsibilities things. You generally have your responsibilities in a role. Not everybody can do all the responsibilities that are given to them. They have to figure out how to prioritize those. But then you also as a group have to prioritize and bind things.
Ash Oliver:
It's a collective process and experience
Jasmine Friedl:
Yeah, absolutely.
Ash Oliver:
If I'm summarizing correctly.
Jasmine Friedl:
Yeah, definitely.
Ash Oliver:
I mean, unlike cake, building products is never done. Building the culture is never done. But if you could describe what that idyllic end result might look like, what do you think is part of the culture and the environment that makes, especially for design organizations, the best possible combination of factors in order to create the best possible outcomes?
Jasmine Friedl:
That's a really good question, I think it goes back to humility. When I think of both people and process and product, it's like, maybe we have to bake the cake again, maybe the first one or the soufflé fell flat or something like that. But it's like, how do you look at everything as a learning opportunity? You have to let go of that preciousness. The idea is that we're all learning as practitioners, that we're all learning as leaders, that we're all learning as product people, and that our product is learning. We're learning about our customers. We're learning about what drives success. I think that sort of humility is just critical. That seems to be one characteristic that supersedes just the idea of people, but also into process and how we work and what we deliver.
Ash Oliver:
I feel like that's so timely and poignant because I also feel like culturally we over-index for assuredness and confidence and knowns, and so much of learning is sitting in the unknown, or at least having the ability to listen, to be able to make a different decision or act in a different way. I'm wondering, just as my last question as I then transition into our hat trick questions, how much of this culture do you think gets into the product and is seen in the product on the outside? Do you think that some of the things that we're talking about actually translate into decisions that you see implemented into the product?
Jasmine Friedl:
Probably not enough. I've been thinking a lot about design ethics and leadership responsibility. Lisa Angela had an article on Medium called Undoing the Toxic Dogmatism of Digital Design. I mean, it's just poignant, and it's talking about getting rid of methods that don't work and losing the safety to explore and fail, and how we don't have ethical standards, and inclusive design and accessibility are afterthoughts. I've just been thinking about what it would mean to incorporate ethics at the front, to incorporate diversity and inclusion at the front of our products, not just our organization and our practice. But we still aren't really addressing a lot of the big things.
Product is still contributing to terribly negative things for humans, for groups of people. That's where I want to see and want to be an advocate for more change in the strategies we write and the people we hire. How do we actually account for what could go wrong? How do we start to think about those things that are missing? When I think about iteration and humility, I think the question that needs to be asked is so much bigger than what we're really focusing on right now. It's for the world, not just for your product. How do you iterate for your product? It's like, how do you iterate for a positive impact on the world?
Ash Oliver:
That's hugely important. I feel like there's more questions than answers.
Jasmine Friedl:
Maybe that's the start. Maybe we ask the questions. Are we even asking the questions? That is probably the thing that we need the most right now in this stage of where we're at.
Ash Oliver:
That's such a great place to end it. I want to transition into our personal questions, questions we ask every guest. The first question I have for you, Jasmine, is, what's one thing that you've done in your career that's helped you succeed that you think few other people do?
Jasmine Friedl:
Quit roles when I know I'm no longer growing, they're not living up to my values, or they need somebody else. I'm proud of myself for that, for saying no because I'm not someone who says no.
Ash Oliver:
Wow, I appreciate that. You mentioned two books that you're currently reading. What is the industry-related book that you've given or recommended the most?
Jasmine Friedl:
Looking at my bookshelf right now, I think it's Just Work by Kim Scott. So Kim Scott wrote Radical Candor—mixed reactions on that. But what I love about Just Work is that she talks about writing it in response to Radical Candor because she realized that Radical Candor was written from a place of privilege, and that the idea of being able to just speak up and have that care, but be bold, is mostly afforded to non people of color and afforded to people in senior positions. She talks about how to create fast and fair environments, and she talks about bullying and aggression. I don't have the framework, but it's basically like, are you a bystander? Are you the victim? Are you the perpetrator? And then in these different... Is it a sort of bias? Is it prejudice? Is it bullying? And in this three-by-three matrix of things, what is your responsibility? And I think it's the only book I've read that sort of addresses what DEI really is head-on.
Ash Oliver:
I love that. I love that recommendation and it relates so much to what you were talking about. I appreciate you bringing that up. My final question for you is, what is an unusual habit or an absurd thing that you love?
Jasmine Friedl:
Every night before I go to bed, I talk to my dogs, and they're sleeping, and they're just such aliens, and I love them so much, but they're usually snoring. I get right up in their faces, and I go nose to nose with them, and I tell them that I love them. And I sit there for five minutes with each of them, just petting them and snuggling with them and holding them. I think it's because Bacon is six and Meatloaf is three, and I'm worried I'm going to lose them, and I just want to cherish every moment, and I want them to know that I love them.
Ash Oliver:
This is the perfect answer to this question. It exemplifies the caretaking and stewarding that you do for all of those around you. I appreciate you inspiring the important questions that we should be asking and remembering the care, attention, and love that we give things around us. This has been a beautiful conversation.
Jasmine Friedl:
This has been fun. Thank you.
Ash Oliver:
The Optimal Path is hosted by Ash Oliver and brought to you by Maze, a product research platform designed for product teams. If you enjoyed this episode, you can find resources linked in the show notes. If you want to hear more, you can subscribe to The Optimal Path by visiting maze.co/podcast. Thanks for listening. And until next time.