Vicki Tan: Ask This Book a Question

Vicki Tan is a seasoned product designer whose work spans Lyft, Headspace, & Pinterest. With a background in behavioral psychology, she brings a unique lens to decision-making and design.

Join us as we explore Vicki’s journey, how she turned curiosity into a powerful creative tool, & why her new book "Ask This Book a Question" reimagines cognitive bias as a pathway to insight.

Transcript

Intro: [00:00:00] From Silicon Valley, the heart of startup land, it's Getting2Alpha. The show about creating innovative, compelling experiences that people love. And now, here's your host, game designer, entrepreneur, and startup coach, Amy Jo Jo Kim.

Amy Jo: Vicki Tan is a product designer, researcher, and author with a background in psychology and behavior design.

She's worked at leading tech companies like Google, Lyft, Headspace, Spotify, and Pinterest, where she designs thoughtful human-centered experiences.

In her new book, ask this book a question, Vicki invites leaders on an interactive journey of self-discovery This book is filled with thoughtful prompts to help you slow down, reflect, and connect more deeply with yourself as you ponder life's biggest questions.

Vicki: I think everyone in tech should work outside of tech at least once in their career.

Making decisions still feels hard. And I [00:01:00] felt cognitive biases or behavioral sciencewas this huge evidence-based body of knowledge that people weren't using in their day to day.

When I was born, I was very premature and that's how I got my name, Victoria stands for victory. So I almost didn't make it.

Amy Jo: Join me as we explore Vicki's insights on mindfulness, creativity, and having the courage to take a leap and try something new.

Hey everyone. Welcome, i'm here with Vicki Tan and we're gonna be talking about Vicki's new book, which we'll be diving into in some depth and even showing you pages from the book.

Vicki, I'm so happy that you're here. since we last talked, you've been around the world and you're doing some amazing things at Pinterest now, and you actually published a book. Got it. Done. Yay. 

Vicki: Took a long time. Yes it was short and long at the same time.

Amy Jo: When did you first start working on the book?

How long ago? 

Vicki: I [00:02:00] went back to LA for a wedding last weekend and I reflected that when I quit my job at Headspace in 2018. That was when I had the idea to make something non-digital, to help people learn about cognitive bias 

I think I played around with it for a year or so, maybe a little bit less.

And then the pandemic happened. So I took a pretty long pause. I think the whole world paused a little bit for everything. But I got a job again it felt like it wasn't quite clicking. So I did stop for a couple years and then when I got laid off. It felt like the perfect moment to start it back up.

Amy Jo: So could you tell us a bit about your background? You have an extraordinary background and I think it'll really help people understand how you came to the, frame of mind that was able to produce this book. 

Vicki: Yeah, I'm happy to, 

I always love to start with this. I was born, in New Haven, Connecticut, [00:03:00] like two months or so early, so it was only two pounds.

When I was born, I was very premature and that's how I got my name, which Victoria stands for victory. I almost didn't make it. So it was a victory, I went to school at uc, San Diego, and maybe unlike some designers, I studied behavioral psychology.

And I worked at research labs and hospitals for the first part of my career. And the formative one for me was working at Lucille Packard in pediatric oncology. And it does sound tough to be in like a. A cancer word for kids all day. But I thought it was just like a really lovely place to be.

'cause there was so much care. I think everyone in tech should work outside of tech at least once in their career. But eventually living in the Bay Area in Silicon Valley, I got lured into tech. Doing a type of research. So research was the connective tissue doing that at Google where we were trying to understand, [00:04:00] this was big, if you can remember 15 years ago, like how we hire or like the people science or what makes a good leader and how we should build optimal teams.

And so I transitioned to. Design at Google. Using my 20% time, making this like internal interviewing tool for people to use. And like I quickly wanted more. I think when you're a new designer at a big company, you get to design very little. So I joined a startup, it wasn't hot yet, but it was a startup at the time, the underdog called Lyft.

And it was way back when we still had balloons and tipping and pink mustaches were the next evolution. But yeah, ride sharing, at least between Lyft and Uber was a little more differentiated. And there, one of the big projects I worked on was redesigning the whole passenger ride request flow, which was a, I think really lucky that I got to do such a big project early in my career.

[00:05:00] Then I moved down to la to work at Headspace. And yeah, I spent another couple years there by the beach. Couldn't have asked for a better crew or sort of situation. I really got to make use of my background 'cause there was a behavioral science team. And I worked on things like an emotional check-in as well as redesigning the onboarding for helping people.

Build more of a meditation habit versus just learn the app. Oh, and that's where I really began speaking about design and developing more of a point of view about design. Then I moved to New York to work at Spotify. This was one of the floors that was my favorite. It's like a cloud room where the chairs were like these hanging.

It wasn't great for working. It was good for thinking, but at Spotify I worked on some of these more future facing brand experiences, what could Spotify be if it was more [00:06:00] of a sonic companion or a thing that brands could use to brand themselves sonically? How else could Spotify look as, if it wasn't purely a music streaming platform with regards to audio books and things like that.

And these days, like Amy Jo Jo said, I am at Pinterest. We just recently had a design offsite where I worked with my friend to teach a little graph workshop. It's really fun 'cause Pinterest is very much creativity and DIY stuff. So we have a conference to do that internally.

The surface that I own on Pinterest is called the Closeup, which is just when you tap into a pin, the bigger view of it. And it seems pretty simple, but there's a lot of teams that collaborate on the surface. So I end up being more of just a facilitator of making sure everything is in harmony on this page.

The last thing I've been doing is promoting all the steps of making a book. Which surprisingly, the making of the [00:07:00] book is only half of it. And then talking about it and promoting it and helping people understand what it's about, which is I think a designer's superpower. That's the whole second half of it. 

Amy Jo: So Vicki, one of the things that you say about this book that I just love, 'cause I'm a huge fan of mental models, and you say this book is like a Magic eight ball.

Tell us what you mean by that. 

Vicki: Yeah. And it was a tricky metaphor. I think I went back and forth on it. Because a magic eight ball gives pretty short answers. It's yes, no, maybe I forget the options, like something will be revealed a little bit mystical, but I use that metaphor to help people understand the type of questions that you might come to the book with.

So it's not factual and it's not list out these things so I can make a, travel destination decision. It's a little bit more of the stuff that you've been like pondering or wondering. So I frame the [00:08:00] book as like a different type of magic eight ball that kind of starts with the question you might ask one, and then it takes you on a journey from there.

An infinite magic eight ball. 

Amy Jo: I love it. One of the aspects of the book that makes it feel like a magic eight ball is the way that you chunked the content. 

And I know that you do have a presentation. I. About the book. Perhaps you could share that now. Yes. And we could get into your mindset because as a fellow designer, I was really struck by how well chunked that content was.

And I thought about all the things you've worked on and thought there might be a connection here. 

Vicki: Yes, as I said, I started the book back in 2018 and I think it's super useful for anyone embarking on any bigger ambitious project to know that it takes a while and it's not linear. So I know people say that all the time, but for you all, I think to [00:09:00] see the process, I think really, makes it tangible.

Where I started was that like the insight, when I quit my job, it was okay, making decisions still feels hard and I felt like cognitive biases or behavioral science, just this stuff that I studied was this huge evidence-based body of knowledge that people weren't using in their day to day.

And making decisions still feels hard. So as a designer, I think my question was like, how do I take the things that I know? So behavioral science from a long time ago, but ingrained in me design, which is things I've been doing every day, making stuff easier for people to use. And then I don't know if problem solving is a one-to-one here, but I just filled the last little corner with that.

I wanted to solve the problem of making decisions. I started off by actually redesigning this bias wheel that my friend Buster Benson, who Amy Jo knows as well, like he had this huge categorization of biases. If you look on [00:10:00] Wikipedia, it's cool, but it's hard to use. And so I started off by just I wondered, would it be simpler if I made a wheel that would just show one definition at a time?

This kind of turned into more of a movable, not one-to-one, but this turned into this concept of what if I could take each bias and really had this sort of dreAmy Jo idea that I could reveal the bias before your eyes. Like a very not thinky, but intuitive just seeing the bias revealed.

And when I went to my agent, she really loved the idea of teaching people about cognitive bias in a sort of approachable, not hard way, but she asked if I could make it in a more accessible format with illustrations and words and things like that. And because I wanted to. Preserve some of the interactivity.

It became a choose your [00:11:00] own adventure where the interactivity was within the pages. But yes, I ended up writing a manuscript, much more words than this original version. Some people asked me why I designed the book in this way, and it was truly because the book started off quite differently.

And I tried to preserve some of it. I went through a lot of versions. There was a version where it was all very scribbly back of napkin notebook style, which I think looked cool, but maybe it wasn't as easy for people to dig into. And so this is just me, this was the same exact wall behind me, filled with different pages every month or so.

Some of these visuals just show, like I took a paper engineering class. I was really interested in physically making the paper move. I tried different illustration mediums. I was thinking like a whacked crayon might look really cool. And then here are me trying to draw the covers. I'm not a graphic designer, but some of them gotta do the cover.

We got that one twice. [00:12:00] I was really interested in using those isometric exploded sort of architectural diagrams to show how the book maps to each other. But ultimately it felt like that was too much into the insight of the book. So we took that out. If you'll bear with me, I'll give you a little tour of the actual pages of the book.

And I just wanna share that this is the actual, it doesn't look like 300 pages because I don't know who looks at a book like this in Figma, but this is all 300 pages of the book. And I actually designed the whole thing in Figma, which is such a product designer thing to do. 

Amy Jo: Oh my God, I love that. 

Vicki: The way the book is structured is in three parts, 

Yes, there's an introduction and conclusion and glossary, but the meat of it is these three parts. The whole first part is about your question, the book asks you to come with a question, and then as soon as you do come with it, I lead you on this journey where I ask you to [00:13:00] sit through a few different, you could call them filters or points of view, which are topic, timing, and blockers.

And this is just like a walking along a path, like what strikes your fancy, and if your question happens to be about one of these topics, I hope that you'll go in and first of all, find a page number to go to in the rest of the book. But second of all, I hope that the way that I've visualized the concept or the category helps bring some insight to your understanding of it.

So you know in this one, yes, you're interested in your mental health, but have you considered it in relation to your physical health and your social health? Or, the same thing with relationships. You might be curious about your romantic relationships, but have you considered how the other layers of relationships are adding or affecting that question?

And so I try to teach you as we [00:14:00] go. Very implicitly there's nothing that explicit about it. But we keep going. The next second obvious thing for me at least in this flow was okay, maybe it's not the topic of your question, but it's more of like the timing of your question that makes it hard to answer.

'cause you have to answer it now or it's once in a lifetime and I've just created these little frameworks to help you. It's truly about learning, teaching yourself why you're stuck with this question, which is why you've come to the book in the first place with this. And so we go on this into more and more kind of loose stuff.

Maybe it's just something's in the way your intuition is off or something like that. So all of those pages intend to lead you to either part two or part three. Part two are these stories that are I've been calling them personal fables. Some people have been calling it an untraditional memoir, which I think is really sweet.

But they're stories that I would tell people if they needed. [00:15:00] Over a campfire, but stories I might tell you on a walk. Of how I adopted my dog or something like that. Stories from friends or mentors. And the different part about this versus a different book about cognitive bias that is story-based, is that instead of writing a story about, let's say, attentional bias or writing a story about fundamental attribution error, I've written a story that is supposed to be resonant, and then I've called out the biases as they show up, which I think just makes it much easier for people.

To take the wisdom versus forcing like the education down their throat. But then when you wanna like double tap into this bias, let's say it's the isolated choice effect or a effort justification, you would just go to that page at the very end of the book, which is part three.

And part three is really the meat of the book, but we've not covered, but I've put it at the very [00:16:00] end because I think that is something you might go back and refer to, but it's not necessarily the focus. I didn't wanna be so on the nose of learn cognitive bias.

So the hope is that you'll go and you'll read one of these biases, and you'll notice that I framed it in terms of yes, the shadow, the thing that we're always told to look out for how bias might lead us awry, but also the light, which is Hey, if you understand. These strategies that your brain is taking on your behalf, then what can you do when you lean into them?

Similar to if you understand the shadow side of your personality, anything, your parts work, if you've done any of that. Once you are starting to embrace that it's really, exciting where you can move forward from that. So these pages are trying to rebrand bias a little bit and I'm not saying it's bad or good, but right now it's really branded as something bad.

There's so much more that I think I could talk about forever, but that's a good little [00:17:00] overview of how you might go from part one to part two and then somewhere into part three and you might go to another bias 'cause it's related and it's just supposed to feel very intuitive rather than reading from page one to page, I don't know, however far you make it in, most of us don't finish books.

Yeah, it's supposed to feel intuitive with the navigation. More of a visual mapping in those question pages. Story-driven learning rather than topic driven. And then a modular structure, which is exactly where we started with Amy Jo Jo saying it felt very structured and chunked.

Amy Jo: How did you user test or reader test your book as you were developing it?

How did you incorporate that into the development process and the publishing process? 

Vicki: Yes. As a designer, every step of the way, all those things that you saw, I was just sharing with friends, sharing with design friends, sharing with people online, constantly getting feedback. I think just being a dis leader teaches you to [00:18:00] not be precious and then show the whole thing.

So I think that was a baseline, but the whole thing was pretty, I don't wanna say it was crowdsource, but from the very beginning, I remember I asked people that I knew. Ask people online and I asked strangers, what are the life questions you're thinking of? And I put all of those in. I should have showed that in the process, I put all of those into my very first Notion database, and then I just categorized them. I was just trying to see if I could find it. If you look on my LinkedIn, it's somewhere in there, but I categorized it. To see where are the, questions coalescing and all of those categories that you saw with life, health, relationships, all of those categories came organically from just organizing in my notion database,

it wasn't a comprehensive list that I started with. So I'm sure we're missing some. That was what people were thinking about, two years ago when I collected the questions. But it's very much been like that. I [00:19:00] think even going from the movable book, I would tell people about it and they would be like, wow, I love that concept.

But then I found myself having to explain the bias and so that was a type of user testing to show that while the concept of the book and the concept of movable was cool. It didn't do the job. It didn't solve the need of actually teaching people about the bias.

So little bit peppered throughout the whole way. The curse of the designer, I.

Amy Jo: that's fascinating. So you were doing card sorts? Yeah, I guess so. Yeah. That's so interesting. For those of you who don't know Vicki's been on our channel before, way back in 2019. We talked about how you, the onboarding for Headspace, but there were two themes that emerged out of that conversation.

One was. Cognitive bias and its impact on decision making. And the other was how to [00:20:00] integrate design thinking into wider realms and other areas of life. And I'm noticing how much you're still on those themes and you've developed those themes. 

Vicki: Yeah, that's crazy that back then it was still, yeah.

Amy Jo: Yeah. You said you started in 2018. 

Vicki: Yeah. But your 

Amy Jo: story is so much about if you absorb. Techniques like design thinking and just that point of view of a designer after being at Google and Lyft and Spotify and all these great companies. So a lot of your book I feel that it both explicitly and implicitly really prompts people towards self-discovery.

If, and I'm wondering for you yourself. That's a lot of years working on the book. It's out now. Life moves on, you're promoting it, et cetera. How did this book [00:21:00] play into your own personal journey of self-discovery? What are some of the things now you feel you know about yourself that maybe you didn't know in 2018?

Vicki: Oh yeah. Gosh. Also five years of living happened, I think two other cities happened. One thing I was reflecting on is when you do one big change, like for me it was going from research to being a designer and taking that leap and that requires doing things that make you uncomfortable.

But when you're young is fine. Transitioning to becoming a designer and then becoming decent at it and speaking about it, that already felt like a great milestone and accomplishment. And I think when you do it once you're like, okay, was that a fluke? Was that lucky?

Was it just the right time and place? And I think to then pick something else, not out of left field, but I didn't think I would write a book, but then it just came across my radar. 'cause I had been making those prototypes and Buster was like, Hey, do you wanna talk to my literary agent?

And then to see that through, I think [00:22:00] personally to feel that I could have an idea to. Be or do something and then just do it. I think that's a really satisfying or self-affirming lesson to know, because then now I'm like, what should I do next? I think it does make you feel like the possibilities or there is no limit to what you can do.

In whatever the span of five years or something, if you really want to, and I know that sounds cheesy, but I think just having the perseverance or just the willingness to suck at it in the beginning or to, pick up some other tools and, venture into another industry that makes you uncomfortable?

Yeah, I think I enjoy that. And then it made me realize that I am the person who does really well for committing and then figuring out versus if you ask me to figure it out and then commit, I'll never get there. Like diving into the deep end, if you will.

Which I really love diving, so maybe that's a through line. 

Amy Jo: I [00:23:00] love that. That's so interesting.

So thank you everyone for hanging out with us today. Thank you so much, Vicki. I could listen to your stories all day.

Outro: Thanks for listening to Getting2Alpha with Amy Jo Jo Kim, the shows that help you innovate faster and smarter. Be sure to check out our website, getting2alpha.com. That's getting[number]2alpha.com for more great resources and podcast episodes.