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Designing the leading collaboration platform

Fail Faster

Episode 440


36 minutes

Meet Stan Rapp, a name in the design world who transitioned from being a self-taught designer to leading Enterprise Design at Asana.

Before his current role, Stan shaped product design at the Chan Zuckerberg Initiative. On top of his design expertise, he’s a certified coach and a recent graduate of UPenn’s Executive Design Leadership program. Specializing in design strategy and co-creation, he’s particularly interested in designing for emotions and behavior change. A native of Ukraine, now residing in the SF Bay Area, Stan has shared his insights at several notable conferences, including The Next Web and Adobe. He has also won awards from SF Design Week and TechCrunch Disrupt.

Podcast Transcript

Khushi: Hi, Stan, welcome to the Fail Faster podcast. How are you? And how was your weekend?

Stan: Hi, Khushi. Thank you so much for having me. I’m good and very excited to be here. 

Khushi: Same here. I’m excited to be talking to you today, you know, because as a leader of design, you have a lot of experience working with enterprises. I’m sure we’ll get a lot of nuggets on this episode. But before we start, why don’t we kick it off with your background? Tell us where were you born and raised? What was childhood like? And your family dynamics? 

Stan: Yes, absolutely. So I was born and raised in Ukraine in a small town, very small town that it’s very hard to find on the map. And my parents are doctors. And frankly speaking, my childhood was, I don’t want to say it was like easy, it was pretty challenging financial resources of my family were extremely limited. So that being said, my parents did everything to give me good education and answer all of my questions, and also show me as much as possible. And school was basically pretty basic. 

I wasn’t into art at all at that point. I think I was closer to technical mindset, I spent a lot of time digging into basic websites, learning HTML, CSS, basic JavaScript. And then there was a moment for me to pick where to go to university. And I actually decided to focus on something absolutely unrelated to design, I focused my attention on banking and finance. So a lot of people say they have a non-traditional journey into design, I believe I’m one of those. And yeah, in the middle of my study, I just like realized that, okay, maybe I was wrong with this whole banking and finance thing. And I would like to go back to something that brings me joy. 

So I started looking into different job opportunities in the tech sector. And my first job in AT was basically a project manager, I was working for an outsourcing company, and I was responsible for creating a very long product requirement documents, something that we call PRDs nowadays. And it was so captivating. Basically, the whole idea was to talk to the client, understand their needs, document it. And on top of that, just like think about the possible solution in close collaboration with engineers. So at that point, I was totally unaware what design is, or how to design, what’s the design process? What are the goals of design, frankly speaking. 

But one day, I actually surprisingly saw a real designer working with my PRD. And that was like so fascinating, seeing somebody turn in basically a very long document into something that you can see on screen. And I thought that this is like really amazing. I was always curious what was like the next step. But finally, for the very first time, I was able to see that. And I thought that, okay, I really want to do that. So I started learning design. And at that point, in Ukraine, there were not a lot of opportunities to learn digital design. 

The closest thing was probably more traditional architecture, which is definitely not the case. It’s still pretty disconnected from digital design. And I just started learning everything available on the internet. So it was early 2008. But I still consider that I started doing design in 2010. 

Khushi: Wow, yeah. And you know, what a journey, like, especially when your parents were doctors, so they were like, not in this field, not even close to you know, what you’re doing today. And then what fascinated you to get into design. I think that’s an amazing story there. Now, one of the topics that we chose today, like for today’s episode was around growing the talent. So first of all, how does your team approach nurturing and developing design talent within the organization? 

Stan: Currently, I work at a company called Asana. Asana is a collaboration platform. And if you haven’t used it, I definitely want to recommend everyone to give it a try. And at Asana, I’m leading one of the enterprise design teams. Even before joining Asana, I always knew about this company because of their amazing focus on design. Asana was always one of those companies with the strongest design. And I was just admiring how everything was crafted with so much love and attention to detail. 

So that’s why it was like always on my list to work here. And well, actually interviewed here first time in 2019. And it didn’t work out that time. But in 2022, everything was perfect. And I am working there for almost a year at this point. Speaking about design, I believe that our leadership recognizes the importance of design and sees design as one of those business tools that help us accomplish our mission and vision. That’s why design is not like an uphill battle where you need to convince stakeholders. But design, this is an equal partner in conversations with product, engineering and data. 

Everyone understands what the value of design is. And that’s why it’s just like much easier to focus on creating great design. Now about the talent, because we recognize the importance, we also recognize that we need to focus on growing our own talent. That’s why we have multiple programs at Asana where we focus on hiring interns basically every summer. Also, at the same time, we have a program for apprentices. So this is for people with non-traditional backgrounds who are interested in exploring design. 

And at the same time, we are focusing on hiring designers who are relatively early in their career, because we truly believe that we should grow our own talent. And this allows us to basically create diverse teams. Diversity in design leads to best possible solutions. And that’s what we are focusing as design leadership at Asana. 

Khushi: Awesome. And like, what steps have you taken to ensure a diverse and inclusive environment that allows growth and development of a broad range of these design talent? 

Stan: I guess everything starts with the basic definition of diversity and equity. Everything starts with different social demographic factors. And I believe this is like, what most of the companies at least should start doing. So this leads basically to situations where we are looking for people again, not just like an average MIT or Stanford graduate, but people coming from all over the world. Even for example, my best example, I am an immigrant, I am a self-taught designer with a degree, but without a degree in design. And that’s just like one of the very few examples where we’re looking to again, diverse social demographic. 

On top of that, I believe our interview processes build a way to ensure that we are attracting diverse talents and we’re not gatekeeping when we create requirements that only a few people can meet, but we are very open about those. So having all of those programs I mentioned before to hire designers who are relatively advanced in their career, this is another opportunity to ensure that more people can apply and be successful. 

Last but not least, there is a significant effort on Asana’s side, just like to ensure that our interview processes minimize the bias, because there are multiple trainings for every hiring manager just to learn more about biases, conscious and unconscious, and how to deal with those. And on top of that, every design manager, and not just like design manager, every leader at Asana is responsible for hiring the best possible talent and setting them up for success. 

Khushi: Awesome. And you were an individual contributor at some point. So what motivated you transition from an individual contributor role to a people management position in the design field? 

Stan: That’s a great question. And frankly speaking, that’s like one of those advice I would give to everyone who is seriously considering switching to people management. You need to clearly articulate why you’re doing that. Because there are a lot of false, in my opinion, at least I define those as false reasons for switching, for example, or that’s the only one way for me to grow at a company. But again, nowadays, most of the companies they offer something that is called a dual track where you can grow as a C and you can grow as manager. And basically, both of those paths are compensated equally. 

Some people switch because they think they will get more impact. And while on surface, that is true, again, in companies where design is appreciated, individual contributors might have even a bigger impact. So our head of design at Asana, he has a counterpart from AC side. And while that AC designer reports to our head of design, this person basically participates in all of the company critical decisions. 

So here is another example, how AC can create a lot of impact. For me, the reason for switching into people management was at this point, more closer to the unconscious side, I just realized that I really enjoy uncovering people’s potential and basically accomplishing more things together. It’s like you are enabling people’s talent. And it was fascinating, because at the same time, I clearly realized that it’s not just about making people feel good enable them, but it’s also about accomplishing business goals. 

And without again, even proper managerial background was back in 2014, I realized that I really again, I really enjoy supporting people and I really enjoy hitting business goals. And I realized that the best opportunity for me to create impact and scale that impact will be to pursue people management track. And this is what I am doing since 2014. 

Khushi: Yeah, yeah, absolutely. And then on the same lines, because you have like that experience with you as a IC as well. So how do you leverage your previous experience as an IC to better guide and support your team members in their respective roles and projects? 

Stan: Yeah, that will be probably another advice I would like to give to our listeners. When you’re switching to people management, you start focusing on supporting your team. And one of the most common things you’re basically letting go all of your design skills. And I think this is one of the biggest traps for managers who are new to the management. Because in my humble opinion, you should never neglect your craft because this will help you in multiple ways. At the end of the day, you’re still a designer, you’re still responsible for the design team and you need to hone your skills. 

You need to recognize what good design is, how to measure good design, what’s trendy. And that’s why number one advice, never neglect your design skills. Please continue investing into those because otherwise, you will become just a manager, not a design manager. And it will dramatically decrease your chances to effectively support your team and create good design. Second thing, I believe having just a good understanding of design, this is required for you to be an effective coach and mentor for your team. Just because again, you know what’s good, what could be better and sharing your feedback on how to do things differently will be extremely beneficial for your team. 

That being said, very likely, if you’re doing design management for a long period of time, your individual contributors, basically the team you are supporting, they will be more experienced than you are. So this is, I believe, pretty close to my situation where I am managing a very talented, experienced team where average basically years of experience in industry is very close to my years of experience or even more. So in that case, consider that your team is constantly practicing design craft, and they are more skillful in design, how to coach and mentor those. So the answer here is look into sports. 

Basically, for every professional athlete, there is a coach. And let’s be honest, coach is typically not so fast, not so successful at this point, coach is coach. But the value that coach adds is having this bird’s eye view on athlete’s career, what they do right and what could be better. And providing that feedback is extremely important. And in order for you to provide that feedback, you still need to be really good at design. Because again, looking into sports, typically, every coach was an athlete themselves in prior times, but now they’re like, focusing on ensuring that younger generations are succeeded. 

And last but not least, I believe that it just like helps build trust and earn teams respect faster, if you are really good in design. And instead of just like providing general advice, you are focusing on providing specific tailored advice for every designer based on your design knowledge. 

Khushi: Yeah. And while we’re talking about people management, and you know, like your role as an individual contributor in the past, self development is also the key, right Stan? So how do you stay updated with the latest design trends, methodologies, technologies, and how do you integrate this knowledge into your own professional growth? 

Stan: I believe I’m privileged to have this growing mindset where I never stop learning. And I am always looking for some new ways of doing my work more efficiently. I believe this is just a byproduct of me being a self taught designer. Basically, you never stop learning. When I switched into people management, I realized that I opened just like completely new area as well where I don’t have a lot of knowledge, and I started learning even harder. And I believe since that moment, I just like started digesting all of the available material on the internet. 

So nowadays, I think I’m a little bit more strategic in terms of how I approach my professional development. First of all, I spent a lot of time reflecting even where I am good at and what could be better. You’re working in teams, and you should definitely always search for feedback. I absolutely agree that feedback is a gift and you should invest into building a safe culture where your direct reports, your peers and your management can openly provide feedback. And you’re listening to this feedback, because I believe that getting feedback, that’s the first step to just like mapping out your plan of professional development. 

Because again, when you know where to focus on, that’s already like a really good starting point. There is an interesting situation where a lot of people focus on their growth areas, and they like, okay, I got this feedback, I should drop everything else, and I should focus on improving this particular skill. I want to invite people to be mindful about that. Because truth to be told, everything we get in our professional careers, we’re getting not because of our growth areas, but because of our strength. And it makes sense to ensure that you’re continuing investing into your strength. Because again, that’s why we’re having these jobs. 

Nobody decided to hire us just because of our growth areas. And I’ve seen multiple cases where people were good at something really good, but they just switched their focus to their growth areas, and they lost their competitive advantage to some degree. So my advice is to ensure that you have a good ratio between supporting your strength and investing into your growth areas. And then to go back how to stay on trend. 

Lately, I’m looking for inspiration in non-digital design areas, because I believe that at some degree, everything is pretty interconnected. And what’s happening in other industries directly affects what happens in digital design and the opposite. So lately, I am spending more time digging into art, digging into our history of art. I’m also really excited to learn more about architecture and history of architecture, why it’s different geographically and what’s behind. And last but not least, I don’t know, there is also something special in fine dining. Man, just like seeing all of the dishes and also even seeing the processes in the kitchen, I believe there are a lot of interesting things we can learn from that industry as well. 

For example, I really like the idea of chefs, because from one perspective, they are supporting a much bigger team. They define the vision, but at the same time, they have bandwidth to cook from time to time. While in tech, it’s like if you’re switching to people management, you’re expected not to invest into your craft. And again, I believe that’s one of the biggest traps for successful people leaders. That’s why I think there was some definitely some interesting ideas we can bring from other industries. And they just like help you be a well-rounded individual with very diverse skills and perspective. 

Khushi: Awesome. I love that piece. And Stan, how did you come to be at this role at Asana? And how was it like working there? 

Stan: Oh, I can’t stop emphasizing how I enjoy being at Asana. I mentioned before that I interviewed for the first time in 2019. And it didn’t work out. But I thought that this is a great learning opportunity for me. And I appreciated that I received a really good feedback about the things that I can do differently. And just like instead of being angry and like shutting myself to this feedback, I took it close to my heart. And I thought, that’s interesting. I really hope that there will be an opportunity for me to try again. 

Three years after I was interviewing at Asana again, the same person who interviewed me in 2018 interviewed me in 2022. So it was like, fun experience from one perspective. I thought, oh my gosh, I really hope that this person just like simply doesn’t remember me. So there is no bias from previous time, and so on. But no, actually, they were quite good with their memory. So they told me that, oh, yeah, I remember you, I even reviewed a school card from previous time. So but this time, it went very well. And I really enjoy working at Asana. 

As to the company, what makes it so special, I mentioned that for me as a designer and design leader, it is extremely important, just like to know that design is recognized. So I’m starting in a good place instead of like spending my time and effort just like educating people about design. I believe it brings joy to some people. Personally, for me, I decided to skip this step and jump to the process of design creation. So something I really appreciate about Asana, this is our culture. I feel this a lot, like Asana has a great culture. 

Nobody was able to explain it to me. But finally, after basically seeing it in action, I can definitely say that there are a lot of talented individuals everywhere at Asana. And it’s just a joy of co-creating something together with them side by side. I believe everyone is empowered to tackle challenges of any complexity. We have not so many levels of organization. That’s why communication happens and like flows openly within the company. And last but not least, I just admire our products. 

And to some degree, somebody might say that I’m thinking my own collate. But honestly, I can’t imagine going to other company and work there without having Asana as a collaboration platform. The whole idea of Asana is to streamline your work. And when I was basically already accepted enough, and I was like trying to learn more about Asana, I’ve heard this like, hey, we are not using emails and Slack at Asana most of the time. We still have those things, but we are not using them. In the very beginning, I was like, yeah, I kind of don’t trust you. How is it possible not to use Slack or emails. 

But now, after being there for almost one year, I can definitely say that this is true. We are not using emails at all. And the only one use case for me to use emails basically to seek calendar invitations for different meetings. And as to the Slack, basically, we are using it for some immediate messages. But most of the time, just like sending funny GIFs and cat images. And that’s it. Because all of the collaboration happens in Asana. The whole idea of Asana as a product is to clearly identify goals, understand what are the pieces of work that will contribute to that goal, and create transparency and visibility into the process. 

All of that happens pretty naturally. And our goal is to minimize effort of using the tool. We have a concept we call this walkabout walk. This is all of the basic work you’re doing, just like to do your actual work. For example, if you’re a designer, just like thinking about, oh, I need to organize this meeting, I need to go to talk to people, I just want to design, I don’t need any of those. And we clearly recognize the base call for action. That’s why we invest significant effort to ensure that Asana is not an issue. But Asana, this is a multiplier of your success, where you can work efficiently and collaborate efficiently, and with some delight. So that’s our internal guiding principle on how to create software. 

Khushi: Awesome. I love that. And how is it like, what’s the innovation appetite that you see within the senior leadership? And like, do you have personally room to innovate? 

Stan: Absolutely, I believe there is constant push to innovate. And I believe this is what differentiates Asana, because we are always trying and looking for something new that reduces this walkabout work and also multiplies collaboration efforts. So lately, I believe a hot topic is AI, everyone is talking about AI. And what’s amazing about AI that basically almost everyone can see immediate benefit. I believe when there was a rise of crypto, Web 3.0, and so on, a lot of people jumped on this topic, but it was really hard to understand what’s the actual product? What should I do with it? 

With AI, people see immediate benefit, you can go and interact with chat GPT, you can go and interact with different graphic or even audio AI tools nowadays, where you, for example, yesterday, I found this website where you can give it a basic text, and it will write you a song, basically in 10 seconds, and I was completely blown away. And at Asana, we realized the potential of AI and started investing into AI very early. I believe to this day, we have more than 50 different AI related features within Asana. And even if we are not talking about AI, our goal is to ensure that we are checking what’s happening in the industry. 

And we are not just like looking to create new features using existing technologies, we are also looking to identify something new that we can create. Basically, our goal is not just like settle with good enough. Our goal is to constantly push ourselves to search for something else. I mentioned before that at Asana, there is a huge empowerment, and you can tackle challenges of any complexity. And that’s something great. You don’t need to have senior in your title, you don’t need to be a head of department to do something. Every individual is empowered and encouraged to do whatever they want to help the company succeed in its vision. 

Khushi: And what would be one piece of advice you would want to give somebody who’s a aspiring designer, like somebody who wants to start in the field of design? 

Stan: That’s a good one. I will… there are actually a few pieces of advice for those people. I would recommend definitely to start with UI skills and never neglect those. Because I believe that visualizing your book and helping people visualize their ideas, this is a true superpower of every designer. Moving quickly from just like theory to something that you can see on your screen and react to, that’s absolutely amazing skill. That’s why please invest into your UI skills. Don’t worry that AI will replace you. 

Again, I believe that this is a very common understanding nowadays. AI won’t replace you, but people who use AI probably will replace you. That’s why that being said, still you need to focus on your UI skills. That’s like my advice number one. Number two will be invest into your personal brand early. And I’m not saying about, okay, you should definitely start a blog or Instagram. That’s like byproduct of personal brand. But I would love to invite everyone to understand what are the topics that are dear to their heart, that are important to them, and invite them to share those thoughts with the world. Because if you’re curious about something, if you’re interested in something, you need to find people who share the same interests. And it’s extremely impossible if you’re not sharing this with the world. 

Otherwise, it will be just like impossible to find like minded people. So spend some time to pause and reflect what are the most important things to you? What are the topics that inspire you? And please talk about them. I guarantee that your ideas will resonate with other people. And you can learn from those people, you can do something with those people. But none of that will happen if you will just like keep all of your thoughts inside of your head. So invest in your personal brand early. 

And number three will be, I think it’s also extremely important to invest into something that we call soft skills, design, and product development. All of those things heavily rely on collaboration and communication skills. You can clearly learn those you can collaborate and communicate more efficiently, you can provide feedback more efficiently, you can bring people together to work on something more efficiently. That’s why I would love to invite people to invest into collaboration, communication skills. 

Khushi: Awesome. Thank you, Stan. Thank you so much for sharing all these interesting nuggets with our audience and being on the show today. Before I let you go, if people want to reach out to you or know more about the work you are doing, where can they find you online? 

Stan: Oh, the best social network to find me will be LinkedIn. Please search for Stan Rapp. I believe there are not a lot of people with this name and definitely don’t be the one looking at Asana. And that’s the best way to reach out. Everything I learned about design and people management I learned from open sources, basically from internet, from different strangers who volunteered to share their knowledge. And I believe I owe pretty much the same to the community. So if there is something that I can help with, please reach out and I will try to help you. 
Khushi: Thank you so much, Stan. Have a good rest of your day.

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