Design Matters with STEPHEN GATES

Published on 2019-07-13
Stephen Gates answering questions from students at the School of Visual Arts Masters in Branding studio in NYC
Stephen Gates answering questions from students at the School of Visual Arts Masters in Branding studio in NYC


“Here’s to the crazy ones. The misfits. The rebels. The troublemakers. The round pegs in the square holes. The ones who see things differently. They’re not fond of rules. And they have no respect for the status quo. You can quote them, disagree with them, glorify or vilify them. About the only thing you can’t do is ignore them. Because they change things. … The people who are crazy enough to think they can change the world, are the ones who do.”

This text comes from Apple’s 1997 landmark commercial for its “Think Different” campaign. And that famous first line—“Here’s to the crazy ones”—can today be found tattooed on Stephen Gates’ arm. He has said that some days it’s an affirmation. Other days it’s a reminder. Regardless, it’s right where it should be 

Born and bred in the Pittsburgh area, Gates’ mother was an artist and his father worked in advertising. As a kid he would write and illustrate his own books, which he printed with his dad on the 3,000-pound letterpress in the basement. (When he got to Kindergarten, he was surprised to discover that his classmates read books written by authors other than themselves.) After an Apple IIGS changed his life, he grew up and found his way to Vertis Communications, where he worked as interactive creative director with some of the world’s top companies; as creative director and designer at TM Advertising; and then as VP of Global Brand Design and Innovation at Starwood Hotels and Resorts Worldwide, where he pioneered apps for the Apple Watch that wound up in one of Tim Cook’s mainstage keynotes. Following a gig at Citi, he now works as head design evangelist at InVision—and in addition to his brilliant speaking engagements around the globe and his podcast series, he’s known for his writings on leadership, design, craft and career.

The following text comes from an article that is a veritable highlight reel of Gates’ wisdoms; he was kind enough to allow us to republish it here to ring in the latest episode of Design Matters.

Here’s to the crazy ones. 


Success is a Choice (and Everything Else I’ve Learned So Far)

As I’ve been searching for the next chapter in my career over the past few weeks, I’ve found myself reflecting on the course my career has taken and thinking a lot about what I did right and what I did wrong. It has been an amazing journey that has let me work on things I never dreamed would be possible, and I want to share some of the things that I’ve learned and have been successful at in the hopes that they might help other people. I think that I’ve been building toward writing this article since I started this blog 12+ years ago, as this piece weaves together a lot of the best articles I have written into one cohesive narrative. My blog has been a critical part of my process in forcing me to constantly evolve as a designer, thinker and leader; since I was sharing the insights I’ve learned along the way, it kept me from resting on past successes. I have broken the article down into the six areas that I think are critical for a successful creative career, and each of those have specifics on how to do them well.

1. Success is a Lot of Hard Work

Over the years the No. 1 question I get from pretty much everyone is, “What’s the secret to your success?” My answer is short, sweet and always the same: “Have great ideas and work your ass off.” I then watch the hopeful, bright-eyed enthusiasm melt off their face as they realize that the secret they are seeking seems to be the two things they apparently want to avoid: time and hard work. The reality is that to be successful takes a lot of time, a lot of hard work and there is just no getting around it. You are going to have to evolve from a designer or copywriter to an associate creative director to a creative director and on and on. Each of those stages will require you to learn new skills and constantly evolve. Here are the two key insights I have learned that have helped me turn all that hard work into success.


One of the most common career mistakes I see are creatives who think that pouring all their hard work into learning how to use applications will make them successful. Don’t misunderstand me, knowing applications is a critical part of any career, but those applications are nothing more than an electronic pencil. Just like a pencil, if you don’t have any ideas to draw, write or communicate, then even the best tool is useless. You need to learn applications to the point where you no longer have to think about how to create your ideas and are just able to let your creativity flow. But it’s that focus on learning applications so they are tools to express your ideas that is critical, because if you only focus on your ability to use the tools, then you will hit a ceiling because agencies and businesses value the ability to create ideas over the ability to just create executions.


As I put together this article I wanted to pass on tangible advice, but I will admit that there is also an element of luck in being successful. It happens when you get one of those rare and magical moments where everything you need lines up and the universe gives you an amazing opportunity. The problem is that most people are completely unprepared to act on those opportunities and they either don’t have the skills, knowledge or insight to take advantage of them. I have found that to be successful you have to be willing to constantly work and prepare for these future opportunities even when you don’t know when or if they are going to arrive. It is a hard thing to do because it requires a lot of discipline, self-motivation and belief that the work will pay off at some unknown point in the future. I have always tried to approach my career like it is a blue-collar profession; I work to evolve the skills I think are strong and work to learn and improve the skills I think are weak. For me it has paid off because when those rare moments come around I have been ready to take advantage of them, which has made all the difference.

2. Success is an Idea-Led Career

I’ve always focused on making the foundation of my career the ability to deliver great ideas over the ability to just hit a deadline, know a new technology or use an application. I think this has worked because those applications, technologies, design aesthetics and even the needs of society have changed, but the need for great ideas will never change. Here are the three key insights I have learned that have help those ideas get stronger and work better within a team.


In my article “Jiro dreams of sushi. You need to dream of design,” I wrote about master sushi chef Jiro Ono, who teaches his chefs that to be a great chef you need to have tasted great food so you have a palette and can tell when you cook great food. It’s a critical concept as a creative as well because to be successful you have to be in a constant two-part cycle of experiencing the best of your chosen creative profession and then using that knowledge as a measuring stick to judge your work. This means that to be a great designer you have to constantly experience great design, or to be a great writer you have to constantly read great copy and then you use that taste level and insight to drive your work forward. You also have to understand that this cycle of consumption never stops, no matter how long you have been in the industry. It has to constantly evolve to keep up with changes in society, psychology, technology, creativity and design. I have seen many great creatives who think that they know it all, or that they don’t need to keep up this constant evolution—and they are the ones who quickly find their work becoming increasingly less effective, until their career fades away.


I have always coached my teams on the importance of being able to externalize and share your creative process with the rest of the team, which is a concept that runs counter to what is often encouraged by a lot of companies where individual achievement and ownership is valued over the work of the team. I think it’s important to not only share your process and ideas with the team, but to develop a culture where the team will constantly try to pressure-test and find weak spots in those ideas to make them stronger. It’s something that requires strong leadership to work so that everyone doesn’t feel like they are being attacked or their ideas are being put down, but instead allows everyone to contribute and take ownership in creating the best ideas. I have seen this concept work as the core of a lot of groups at companies like Apple and Google, where they are relentless in seeking out the best ideas by sharing their work, knowing it can always be better and using that process to continue to refine it until it is something great.


Also in “Jiro dreams of sushi. You need to dream of design” is another theme in which Jiro talks about his lifelong dedication to sushi and his constant work to improve his craft. This is a trait that I’ve come to embrace over the course of my career, and it’s a trait that I see shared by every great creative mind I’ve ever known. I think it’s a byproduct of the fact that they constantly work to develop their palette and they constantly want to make everything they do better. I’ve come to embrace the fact that there is no time when design is completely out of my mind, because I am constantly looking for new inspiration, tormented by the flaws in my old work and looking for that next great idea. When a project is finished I allow myself 15 minutes to enjoy the work that was done, and then I am onto the next project. I have little use for nostalgia because when I look back I see only the mistakes and things that I could have done better. Nostalgia is for people whose best days are behind them and for people who look to the past for answers. That eternal dissatisfaction can be a strong motivating force to keep your work moving forward, but it is also something that needs to be kept in perspective because if it gets out of balance, you can become a naysayer who lets that dissatisfaction take over their process and blind them to new ideas.

For Lessons 3, 4, 5 and 6, click here. 

--Zachary Petit, Design Matters Editor-in-Chief


Stephen Gates:  Because I was so well known at the company, whenever I was laid off I was deemed a security risk. So I had to come in at the end of the day on a Friday. I was not allowed to see my team or talk to anyone. I walked into my office and my desk is covered in these Polaroid photos. And every single person that I had worked with took a photo of themselves holding up a sign about how I had affected them.

Curtis Fox:  This is Design Matters with Debbie Millman from On this episode, Debbie talks with designer Stephen Gates about why it's important for a brand not to be liked by everybody.

Stephen:  For most brands, whether they are personal, whether they are for a company, people will try to like, "I want to please everybody. I want everybody to love me. I want ... " And that's just not real.

Curtis:  Here's Debbie.

Debbie Millman:  Most designers discover design. That is, they don't even know design a thing until somebody tells them about and they realize that's what they've been doing or that's what they want to do. Not so with Stephen Gates. His father was a creative director and he pretty much grew up in an ad agency. He now has over 20 years experience designing ad campaigns and digital experiences. He's been Global Head of Design for Citibank and he's now Head of Design Transformation at InVision, where he works with brands including Google, Nike, and WeWork.

Debbie:  Stephen Gates, welcome to Design Matters.

Stephen:  Thanks so much for having me.

Debbie:  Stephen, you've described ITC Serif Gothic as the design crush of your youth. Why and what about it was so alluring?

Stephen:  I think, well for me, like you said, I grew up with a father that was a creative director, so my relationship to typography and design, I think, started in like the most old-school way in that my Dad used to have this 700-pound cast iron letter press that sat in our parents' basement. For me, what that meant was I had this incredibly artistic and creative upbringing. My Dad and I would go down in this small room in the basement of our house and that we would kind of write my own children's storybooks and then I would go about typesetting.

Stephen:  But, for me, you really started to get this appreciation for what was typography and what was leading, and what was a typeface and what went into it before you could just sort of scroll through this massive menu of thousands of fonts. So, yeah, I think that I have a very nostalgic relationship to certain typefaces, to the smell of printer's ink, a lot of these sort of things.

Debbie:  Where did your dad work?

Stephen:  So, he worked for, at that time, it was a small agency in Pittsburgh that had sort of regional accounts like Alcoa, and the Western Pennsylvania Conservancy, and he'd worked at Ford in Detroit for a little bit while longer, and then had kind of moved to Pittsburgh and had joined that agency.

Debbie:  And is it true that you did all sorts of original gangsta type rubylith cutting, and-

Stephen:  Oh, yeah. I was doing it before even computers were introduced to the industry. I remember the first sort of like Mac classic showing up at the agency. So, no, I remember doing rubdown typography, and cutting rubylith, and doing pay stub keys, and a lot of stuff people have to Google to figure out what it is these days.

Debbie:  Now, despite your family connections, and despite working in the ad agency with your dad, and despite making your own storybooks on the letter press, you've said that Star Wars is really the reason you ended up going into a creative profession. In what way?

Stephen:  I think it was. Because there were movies. I mean, I think Star Wars and Tron were those two, sort of similar moments in my childhood as I think anybody of that era was, where I think you just started to have an understanding of what storytelling was, and what visual effects was, what imagination was, so far beyond the bounds of sort of what you were used to. And I did, I really sort of had become obsessed with it, and I think like most kids of that era, really started to want to set about to understand how did that get made, like who did that?

Debbie:  But you were four years old when the first Star Wars was released.

Stephen:  I was, but, again, you have to remember that, I mean, this is a kid who's also doing letter press typography, and so I think that idea of just sort of being in, around creativity, it really sort of set the seed then, and sort of set me on that path.

Debbie:  You said that your enthusiasm for the saga waned after the prequels, many years ago. You described them on Twitter as crimes against your childhood.

Stephen:  Yeah.

Debbie:  That's pretty serious.

Stephen:  Well.

Debbie:  Well, I mean, they were bad, but they weren't that bad, were they?

Stephen:  Well, I think, I knew it was interesting. I think not long ago, I ended up having a brief conversation with Frank Oz, who played Yoda, and has done the Muppets, and I think, he-

Debbie:  Oh, you just needed to throw that in there. 

Stephen:  No, I mean, it wasn't, I think it was-

Debbie:  ... and Frank Oz, and Steve Woz, and-

Stephen:  No, no. I tend to really seek out these people. No, this was me sneaking into a speaker room at South by Southwest and figuring out how to snag a couple minutes with him. But, he's sort of said that he felt like a lot of that, when it comes to nostalgia and expectation can never be lived up to. And I think there is sort of a childlike quality to remembering what's that like and what those movies were, and yeah, I think that a lot of them, for me, those movies traded too much on the past. They didn't build their own narrative. And again, I think the originality, and the freshness, and the fun of the originals sort of got lost in trying to figure out how to make a carbon copy. And that sort of creativity never really works.

Debbie:  Now, your mom was a toy maker, is that true?

Stephen:  She did. She made these soft sculpture hand-made toys for children. If you can think of like puppets, or stuffed clowns, or different things of like that, and she really done that because she studied fiber arts in art school, and wanted to stay home to be able to help raise me. And it let her have this one woman cottage industry out of our house, doing these sort of wildly creative, handmade toys.

Debbie:  So it seems like it would be fair to say that you got your entrepreneurial genes from both your parents.

Stephen:  Oh, I think my parents remain probably the biggest inspiration. And I think I owe my career and everything I have to the two of them, because I think they set me on this path, where I think a lot of people will start, like you said, sort of having an awareness of these things when they come out of art school, and I mean, I had it before I was probably in high school.

Debbie:  You've written about how you part of the first generation who could look back and tell you about the computer that changed your life, which was yours?

Stephen:  Mine was probably a very, very old, original Texas Instruments. I don't even remember what the model number was. But it was so old, that you used to have to get magazines where if you wanted a video game, you used to have to write the code out of the magazine, and then sit there and debug it. And then record it on like an audio cassette. Yeah, I feel like I date myself horribly, but that was sort of the one that showed me, okay, how did you add code and technology into art? What was the interplay between the two? Even in such a primitive form, and again, sort of helped me in that next evolution of my kind of creativity.

Debbie:  You've said that having an upbringing with creative parents helped you see that even the newest technology isn't much different from a pencil.

Stephen:  Yeah.

Debbie:  Do you still feel that way?

Stephen:  Absolutely. Because I think in a lot of cases, we get very caught up in production technique. We get very caught up in technology. We get very caught up in a lot of those sort of things, but at the end of the day, storytelling really hasn't changed that much, no matter what the medium is. If there is not a human truth at the center of it, if there's not a message, I don't care if it's social media, or anything else like that, if you aren't doing that, then yeah, they aren't that dissimilar from a pencil, but I think a lot of people, especially in digital just, they get very caught up in the technique, and as with anything, cool does stay sold, cool doesn't stick around, but a really deep, kind of meaningful experience will.

Debbie:  Do you still use a pencil frequently?

Stephen:  Oh, absolutely. I often joke that I have this problem where I can't talk about an idea without sketching some part of it. I think this goes back to like my father would always used to walk around with like a vellum pad and a Sharpie. I think, for me, it's an iPad and an Apple Pencil. But no, I constantly kind of do that. I think even the best teams that I work with, I used to joke, whenever ... I knew I had a really good relationship with them, when I could kind of like make three lines and a noise. It would be like, "Okay. It's like this, this, and it kind of goes ... " And they'd go, "Okay." And be off to go work on something, but-

Debbie:  Oh, so an actual noise, not a pencil noise.

Stephen:  No, no. Like an actual-

Debbie:  Which I love the sound of-

Stephen:  Oh, yeah.

Debbie:  ... a pencil on paper. But a ... or a ...

Stephen:  Yeah.

Debbie:  Now, you've referred to yourself as an outsider when you were in high school, as you were growing up. In what way?

Stephen:  Oh, in a lot of ways. I think I went to a public school that was in, this was in Pittsburgh in the 80's, whenever, the city was going through a hard time, half the population had left. It was a school that was predominantly African-American. I was one of just a handful of white kids that had gone there.

Stephen:  So I think one hand, racially, being very much on the outsider, I think I was in the gifted program, so that makes you very much on the outsider. I think I spent a lot of my time working at my dad's agency, so I spent more time with adults than with a lot of other people. So, a lot of cases, for me, my best friends were adults, which was not the way most high school kids grew up. And so, yeah, I think that, for me, it really had always been, well, I was ... I was kind of a kid among adults, but I felt like I was adult among kids. I never really had a place that I kind of felt like was mine.

Debbie:  You said that you're not sure you had much choice, but to go into design. Yet, I read that your parents didn't really want you to have a career in the arts, which is so unusual, given their careers, and the influence that they had on you. Why didn't they want you to do something in the creative field?

Stephen:  It wasn't that they didn't want me to do the creative field, I think they didn't want me to feel like, since that was what both of them did, that it was sort of predetermined that that's what I had to do.

Debbie:  Did it feel that way to you?

Stephen:  I think that it did. Because they were very much into taking me to computer programming classes, or I was interested in marine biology. I had a very schizophrenic sort of interest set, whenever, I was at that age. And so I think they just sort of wanted to encourage me to be what I wanted to be, and not I didn't have to go to school where they went to school. I didn't have to go into what they did.

Stephen:  But I think whenever you surround yourself with that, and when you come from that, and it almost feels like it's genetic, sometimes. For me, that was, no matter what I did, I was always sort of drawn back to that place.

Debbie:  And did you always feel like you knew you wanted to be a designer? Or work in a creative field?

Stephen:  I think I always knew I wanted to be creative. I think whenever I had sort of gotten to college, there was that joy of teenaged angst of like, "I'm going to be creative, but not the way my dad does." So, instead of whereas he'd worked in print, I had decided I was going to go kind of explore what was the early days of digital and doing things like that to kind of strike out on my own. Because that was sort of me trying to find my identity. But, no, I I think that, for me, that was always what I really loved.

Debbie:  You went to Syracuse University, and studied computer graphics. You then went to work as an Interactive Creative Director, collaborating with clients like Disney, and Motorola, and Intel. And you then became the Creative Director at TM Advertising.

Stephen:  Yeah.

Debbie:  At this point, did you prefer advertising to design? Or were you looking to have that sort of range?

Stephen:  I think, at that point, I liked the range, because I think I've very much, because I'd worked at my dad's agency since I was 12. I understood advertising very well, and I'd gone to Syracuse, because that was the first degree giving program, and at that point it was called computer graphics. They didn't know what digital was then. And so, I was this sort of weird bridge, where I could speak to the old school, kind of creative advertising, creative directors, but, then, at the same point, I could program, and I understood this sort of new technology. So I was this kind of interesting bridge to be able to work between the two. 

Debbie:  How did you navigate through the different roles in an agency, and end up on the creative side? Did you ever consider strategy? Did you ever consider account management or production?

Stephen:  I think a lot of it for me was very early on. Again, whenever you have the advantage of starting in an agency when you're 12 or 13, I very quickly realized that the thing that was going to differentiate me was my ability to have ideas, my ability to pitch, and sell, and that just doing design was going to be a fairly limiting career. Because you have to start with that sort of base execution, but as I looked at the work that I found really interesting, it was well beyond that. So I think that, for me, it was how do I get into doing more of the new business work? Or doing more pitch work, or getting more into the ideation. Because that was more of where I wanted to center my career, that it was great that I could go in and design this stuff, but I could really sort of see a fairly short runway on that.

Debbie:  In 2006, you became Senior Creative Director, Global Digital Brand Design and Innovation, at Starwood Hotels and Resorts Worldwide, which owns the Westin, Sheraton, W Hotels, the St. Regis, Aloft Design Hotels, and more. And you've said the design team was overlooked when you first got there. Was that something you knew before you got there? Were you hired to make a difference in that way in which they were being perceived?

Stephen:  No, it was. That was a job, I think I'd turned down two or three times, because it was just, the setup was wrong.

Debbie:  In what way?

Stephen:  Because, why, they were reporting into like project management, they were aligned the wrong way, that the way they were going about their work was wrong. And I had started, at that point, to realize that in my career, I was never going to have more power than the moment between when a company decides that they want to hire you and when you say yes.

Debbie:  Correct.

Stephen:  Because the ability to set up years of success to come, can really be dictated in that moment. Because once you're there, then, it's kind of like great, you lose all your leverage.

Debbie:  You're trapped.

Stephen:  Right. And so, I kept turning it down, because it was reporting to the wrong people, and their head of digital just said, "Look. Can you fly to New York and we have dinner, and just talk? I think you're the person we want." And I felt like I had nothing to lose. And so I showed up with this, a rather extensive, I don't know what, 10 or 14 page document, where I detailed, in-depth, what I thought was wrong with their brands, what was wrong with their website, what was wrong with their team structure, thinking this person's going to go, "You're out of your head."

Stephen:  Showed up, reviewed this whole thing, and he said, "This is exactly what we need. These are the changes we need to make. Do you want the job?" And it was like, "Oh, crap."

Debbie:  That's ballsy. You went with a 14 page document-

Stephen:  Yeah.

Debbie:  ... outlining everything. Now, what made you decide to do that? Is that what you feel it takes to get the kind of job that you were in the running for?

Stephen:  No, I felt like-

Debbie:  I mean, did you do that for every job interview?

Stephen:  I've done it for a lot, where I think, at some point, I've made some big player. Because in a lot of cases for me, I've just really realized, brands can look great from the outside. And people go like, "What company are you going to work for?" I don't really, that's why my career path sort of looks a little drunk. Because for me, it's more about, it's about the leadership, it's about the organization, it's about the opportunity.

Stephen:  And for me, if I was going to leave, I was living in Texas at that point, working at TM, which was part of McCann. If I was going to leave that, and come back to New York, it had to be the right opportunity, not just any opportunity. And I think there's, sometimes whenever you're doing that job hunt, it just, any interest can feel like oxygen. Because you're just, "I want to make a change, and anybody who says they love me, I want to run towards." And I just kind of felt like, "Look, if this is really going to be right, if they're really serious about making this change, this is what I think it's going to take. And anything less than this is not going to be a job that I'm going to want." The worst that was going to happen is they were going to say no.

Stephen:  And that was fine. And that was going to prove that that wasn't the right job for me. But, like I said, I think for me, that moment set the success up for the next nine years that I was there.

Debbie:  Do you have these standards in all areas of your life?

Stephen:  I don't know. I think that I try to be clear about what matters. I think I try to be clear about what matters to me, about what is negotiable, and what is not. And some people will absolutely love you for that. And other people will describe you as devisive or difficult. But I really feel like, in many cases, for me, if I was going to go about building a brand, if I was going to go about creating something, I want to build a brand that is strong enough that somebody would actually hate it, because it stood for something that was strong enough and clear enough that you could say, "Yes, that's for me." Or, "No, it's not."

Stephen:  And I just felt like so many people were running around, trying to be what everybody else wanted, that they were missing who they were.

Debbie:  What were the first changes you made when you got to Starwood?

Stephen:  A lot of it for me was just really looking at how did we shift from being in organization whose value was design, as an execution, to having our value really be about creativity and ideation. Because, whenever it was just purely design and executional piece of that, it was always going to be viewed as a commodity. Because it was always just, "Here's a solution to be vetted and not a problem to be solved."

Stephen:  And that was a real issue. So a lot of it for me was, I needed to change the organization around the team to get them to see the creativity and the power that was there. But I also needed the team that was there to believe that they could do different work, that they could be better. And I really saw that the talent was there. It just had sort of been overlooked, and a little bit kind of abused, and neglected for a little bit too long.

Debbie:  In addition to that period between when you've been offered the job, and when you formally accept the job being so critical to a job's success, I feel like the first hit out of the gate, that first success that you establish is also critical in establishing credibility. What was your first success in that new job?

Stephen:  I think my first success was really going in, and just saying, "Look, we have a process, we have a way that we're going to go about this." For me, it's never been about going after what's the big cash cow, what's the big project, how do I make a big splash? Because those are the areas that are going to have the most resistance.

Debbie:  Why?

Stephen:  Because they're the ones that have all the money, they're the ones that have all the political capital tied up into them. They're the ones where you're going to find the most resistance. So, for me, it's looking around and saying, "Okay, what are the ones that are important, but maybe are a little bit neglected?" And that point, there was an extended stay brand called Element that we were working on. And it was sort of trying to get figured out. And I was like, "Look, that's where we're going to go and sort of invest the time and the design to be able to do that." And so that was where we started. Because any project like that that's been neglected, the people who work on it love the attention. You can make a really great case study out of it, and it's easy to be able to find some success, and then off of that, build that in and then go attack the bigger problems.

Debbie:  You were hired at a time when the design team was really only responsible for the brand's website.

Stephen:  Yeah.

Debbie:  And soon, though, as you've said, your job grew into what you've described as designing experience across all 10 of Starwood's design lead lifestyle brands. For websites, from mobile apps, for wearables, global social medial platforms, and emerging technologies. How do you go about initiating that kind of transformation without pissing too many people off?

Stephen:  Well, I think, in some ways, you have to not be afraid to piss people off. Because in some ways, I think, if all you're going to do is go in and just say, "Look, I'm just here to kind of go with the status quo." Nothing's going to change. I will often tell people I think there's a difference between crazy and stupid. So I think that you have to be strategic and thoughtful about how you do it, but a lot of it, for me, was just continuing to stack that success, to be clear with the team about we were going to make change every single day, in every single meeting, and every single thing that we did. And that it was going to take time for us to be able to kind of accumulate that.

Stephen:  So I think that a lot of it, for me, was the ability to go in, roll up my sleeves, work with the team, get success, show business results, and then build on that and sort of earn our way through it to be able to do that. But in many cases, it was also being fine at certain points, not being liked.

Debbie:  I've been listening to your podcast quite a lot in preparation for today's show. And you often critique your abilities, in lots of different ways. And I was struck, today. I was in a taxi, listening to, I think it was episode 58, where you talk about how you might be difficult to work for. You might have used the word asshole.

Stephen:  Yeah.

Debbie:  Talk about that.

Stephen:  Well, I think ... It's a process that I've been working through. And because in many cases, that's sort of the problem in creative leadership. Is that on the one hand, I have a vision, I want to have influence, I want to be able to drive the team. But on the other hand, nobody wants to work for somebody who just tells them all what to do. So, finding the balance of when do you push, when do you give guidance, how do you sort of work through what that is, can be difficult. And I think there are times, whenever, yeah, I want to tell you, "Here's the problem. Here's what I want you to go do." But I think for me and my leadership style, there's always sort of been an or else. And being unafraid to be truly honest about what do I really think. And some people take that really well, and really appreciate it, and respond to it. Other people kind of will take it very personally, and want to make you into a villain, and to do things like that.

Stephen:  And again, I think there are some times the delivery of how that happens needs to be refined. And so, for me, that's been a big process of how do you find that balance, of when do you know when to push? When do you set that expectation and hold the line on this is not good enough.

Debbie:  So, tell me when you do that. When do you know how far to push? When do you know when you've maybe pushed too far?

Stephen:  I think in many cases for me, I try to spend most of my time giving insights, giving direction, talking about the problems that haven't been solved. Trying to set expectations about when do I need this to be done, and kind of what it is that I'm looking for. The more times that comes back, then it's trying to respond and respect the team, and understand their process of saying, "Okay, do I need to leave them alone? Do I need to push on them? Do I need to be honest with them?" The moments when you go too far are the moments whenever trust will start to kind of break down a little bit.

Stephen:  Because I'll often tell many of the teams, like, the moments that you don't want, or you don't want when I start designing. Because those are the moments when I'm not sure that we're going to make it, and I feel like I need to step in. But I think, for me, in going through that, what I've learned is that, no matter what it is, or how hard it is, no matter how hard easy or hard the conversation is, I always really try to approach it and say, "Look. If these roles were reversed, if they are the leader, and I was the person that was on the team, what would they want?" And even if they don't want to hear it, the ability to be honest in that moment, I think, while they may not like it, they pretty much will always respect it and come back and be able to have a conversation.

Stephen:  But I think it also is never for me about just sort of saying, "Here's what's wrong." Negativity is so easy. It's so easy just to be able to point out and rip everything down. But to be able to say, "Okay, look. Here's how we're going to work on this together. Here's how." And I think that, for me, has been the evolution of not just saying, "Okay, this isn't good enough. Here is the plan, this is what we're going to do. This is how I want to support you to be able to do those things to help sort of build them up." Because when they find the breakthrough, whenever they find that growth, I think that's sort of what my role as a leader is, is to try to help get them to those moments.

Debbie:  Talk about how you approach and deal with conflict, both from people that report to you, and people that you work and collaborate with.

Stephen:  I think, conflict, for me, is a natural part of this.

Debbie:  So you're not afraid of it?

Stephen:  No, not at all. Because I think, in many, that's the mistake I see so many teams make. Because creativity's about how did we get it wrong a lot? On the way to finding something that we think we can live with, right? Like this is, like, for us, two plus two equals burnt sienna. There's not a right answer to what we do. And so, for me, the ability to say, "Look, we should have differing opinions. We do need to push each other. We need to try to break our ideas." Those are atmospheres that I really like. Because, I think, for me, it's always been about being confident and respectful but not delicate. With rules that, I mean, I do. I think fighting or things like that is good. Like, who really has the better idea? Who really believes in this?

Stephen:  But, I think a lot of people aren't sure how to deal with that. Just because I have an issue with something, or I want to debate something, that isn't necessarily a bad thing. So sometimes you have to stop that moment, and back it up, and kind of go, "Look, I'm just having a discussion about ... " Because you can watch their defenses start to come up. You can watch them start to get emotional. It's like, look, that's not what this is. And I think especially, again, I'm 6'4", I have a big ... Even no matter I want to, that can come across a much bigger way than I think I want it. But no, I think conflict, for me, is part of it. But it's telling everybody that that's okay. And so when it happens, we're going to come together and work through it as opposed to what normally happens, is everyone comes together to write a bunch of e-mails to figure out who's to blame.

Debbie:  Define your leadership style.

Stephen:  I think that, for me, it's probably spending about 10% of my time just leaving my teams alone, to be able to just say, "Look. There's something stuff you guys need to work through. There are some things that I don't need to be a part of this. You need to find your voice in this." I think about 80% of the time, it's really trying to give insight, trying to give guidance, and knowing that I am, I'm a massive, massive defender of the team. I'm a massive supporter of them. Because I think the two biggest things that I try to ground that style in, is that one, like the work you do tomorrow's going to be better than what you did today, and if it hits the fan, I'm there. And no matter how easy or how hard that is, and that other people in the company know if you do something dumb, you screw over my team, I'm coming.

Stephen:  And then I think the last 10% of the time is, "Look, we are out of time, budget, capital, patience, whatever it is. And we just need to do this particular thing." But, for me, it's trying to keep the first and the last of the nuclear options. But it is. It's trying to be basing it in honesty, it's trying to invest in the team, and understanding their style, that's it's not, just because I create this way, I think it's trying to hire people that have perspectives that are different than mine. Because those sort of tension, I think, are really, really important.

Debbie:  In 2012, you became the Vice President of Global Brand Design and Innovation at Starwood. And true to your title, you honed in on innovation. And discussed innovation in Fast Company. You said, "If you're focused on mimicking what everyone else does, or if you literally take results of focus groups, you'll tend to only innovate in small leaps, because you're just going to innovate on the problem that's right in front of you." So how do you go from leaps to bounds?

Stephen:  I think you realize that for most companies, the trap is that you tend to get stuck in this place where I'm only thinking and innovating as far as the project in front of me. I've been told that I have this brief with this budget and this amount of time, and that's as far as my thinking is going to go. I think, too often, you listen to the average consumer, which I just don't believe in. I think average consumers lead to average insights. I want to start looking a little bit more to the edges for the amateurs and the professionals.

Stephen:  I think that it is kind of saying, "Look, any organization is probably like the Queen Mary. It's not going to turn quick. It's not going to innovate quickly." But the ability to set a vision, to start with a truly honest conversation about what is our actual customer experience? Not do we tell ourselves what it is. But how do we actually start with that? And then, how do we figure out where do we want to go? That ability, I think, will start to be able to lead to those leaps. But I think it also absolutely requires, and that was, I think I've worked with two, once in a generation leaders in my career. One was working with Frits van Paasschen, who came from Nike, who was our CEO at Starwood. Having somebody who gave us the cover fire and the support to go try those leaps.

Debbie:  What is the biggest thing you learned from him in doing that?

Stephen:  I think to truly trust people. Because there are moments that he trusted me and the team I was working on probably far beyond the bounds of what he should have. I think his ability to hire smart people, and to trust them to do their job, which seems to be a very rare thing. And I think, also, his ability to just be really clear about what were the organizational priorities, of what did we need to focus on.

Debbie:  In that very same interview, you also said that, "Having great ideas is a tremendous amount of work." And I don't know that people realize just how much work goes into anything great. That nothing ever just comes out great.

Stephen:  No. I think this has sort of led to, I think I've had a multi-year war on the light bulb. Because, I think the-

Debbie:  Your first episode of the podcast-

Stephen:  Yeah.

Debbie:  .... was The Light bulb is Bullshit.

Stephen:  Yeah, no, it is. For that very reason. Because I think one, is that as a creative industry, we do ourselves no favors in the fact that we try to represent creativity in this iconography that somehow, you wait for this moment, the light bulb appears, and it rains like champagne and puppies, and everything makes sense, which is the furthest thing from the truth. So we need to understand subconsciously, we're propagating a lie. And that, in a lot of other cases, for me, I've always said that, yeah, creativity's a blue collar profession. That a light bulb's a moment of inspiration. It is a starting point at best.

Stephen:  But, as anything goes from that moment of inspiration to the reality of execution, there is so much work, and so much that changes, as it goes through that. And that, again, it isn't just, "Okay, I made this great little concept, and away it goes." Because that's not is actually what's going to go out the door. And the ability to be committed to that, to understand that it is this process, that's what makes the big difference, there.

Debbie:  Stephen, how do you recover from failure?

Stephen:  I think that the easy answer is you just try to say that's what you do all of the time.

Debbie:  Really? Because I cry, I mope.

Stephen:  Oh, no. I know. That's why I said it's the easy answer. No, I think I get, my wife will tell you, I get very down on myself, I get very, very frustrated. I think in a lot of cases, for me, it's, it is trying to remind myself that it is a part of the process, that the only way I'm going to find confidence, the only way I'm going to find growth is through failure. I think your brain tries to trick you into the opposite, that like, "Do what you always do well, and you'll be confident." It's like, no, that's where you sort of become apathetic and stale. I think that a lot of it, for me, is trying to surround myself and find a cohort that will support me, that I can try to externalize that, and talk about it more.

Stephen:  I think too many of us wear these masks, where we all try to convince ourselves and everybody else about how great we are, and how wonderful it is, and social media does no favors. It's like, I'd love if this year for Halloween, everybody went as who they pretended to be on social media.

Stephen:  But I think it's just, we just get to this place where we don't want to talk. We sort of fetishize the beginning and the end, right? We love the brief, and we love whatever the output is. But, for me, it's sort of letting myself have that moment of being upset, of taking whatever that defeat is, but just time boxing, and saying, "Okay, look, you get until tomorrow morning, and then just buck up. We've got to move on. We've got to figure out what the solution is."

Debbie:  Ande La Monica said this about you. "Stephen's tent pole principle and one that is echoed by a lot of successful creative leaders is empathy." Would you agree? And if you do, tell us a little bit about how you regard and foster empathy.

Stephen:  Empathy for me, is the ability to not have the arrogance of thinking I'm my consumer. Empathy is the ability to not just walk a mile in somebody else's shoes, but to continually go back and revisit who that person is. Because I think empathy, the way that a lot of people will define it is that, "I understand a mindset or the way somebody works." I will argue that I think that works to a point.

Stephen:  But at the moment, whenever I start to solution against that, I lose some amount of objectivity. I think that when it comes to my leadership, I do try to find empathy and putting myself in the other person's shoes, and what would they need, and to try to think about their mindset. I think in my work, it's often coming back to revisit the consumer and have them be the source for truth. I think I've seen too many organizations and had too many projects where it became about who was right. Was the design right? Was the product right? Was tech right? That's not, if it's about those political battles we're all going to lose.

Stephen:  But I think that empathy for me is the fact that whenever I'm designing, leading, whatever that is, it's not just about me. So I think that there is a, how do I bring my perspective? How do I bring an interpolation of what it is that I'm seeing, but understand that my opinion is not the end-all be-all.

Debbie:  As a bit of it aside, I love the way you liken chefs and ingredients to design, and I'm wondering if you could expound upon that a little bit.

Stephen:  Yeah, I think, for me, I grew up, my mother cooked dinner every night. And so I was always around food. And food became this massive inspiration for me. Because as I went on my career, I found other industries to be very inspiring, and to be very interesting. Chefs, in particular. Because I felt like whatever you think about the way a chef works, you go from this wild creativity of creating a new dish, and taking the same ingredient, like everybody gets a tomato. But what you can do with a tomato is so wildly different. To then having this thing, saying, "Okay, look. We need to cook this dish exactly the same way every single night, night after night, and it's just about execution." I saw huge parallels in design, there. I saw huge parallels in how do you bring people up through those teams? How do you teach them their craft? How do you foster creativity?

Stephen:  Yeah, I've been on this, I don't know what, decades long quest of traveling the world, talking to chefs, looking at their philosophies and trying to understand how do they do it, and then how could I apply that to design.

Debbie:  What can the butter at a restaurant teach us about design, Stephen Gates?

Stephen:  So, the butter. This is a really famous story, and it's probably been for the last 15 years of my life, the bellwether that my wife uses at ever meal to try to decide if it's going to be a good meal or not. So, one of the chefs that I admire most is a chef named Heston Blumenthal, who has a restaurant called The Fat Duck, which is about 30 minutes outside of London. And he was doing an event, here in New York, I don't know, 10 or 15 years ago. And everybody was sort of standing around, afraid to talk to him, again, I go charging up to get his book signed, and one of the questions I asked him about his process, was whenever you sit down at a restaurant, what's the one thing whenever you look at it, you can tell if you're about to have a really good meal or not?

Stephen:  And his answer was the butter. Which thoroughly confused me. And I asked him to explain. And he said, "Well, whenever the butter comes out of the meal, if it's hard, if you take that, and you cut into it, and the knife almost kind of bends, you know that the chef isn't paying attention to the details. He's never eaten in his own restaurant. But if it comes out, it's room temperature, it's easy to work with, they're paying attention to the details, and that the experience really matters."

Stephen:  So, for me, it was like this really resonant moment about how, no matter what you do, no matter what your position is, you always have to go back and think about what is your version of “the butter.”

Debbie:  What is your version of “the butter”?

Stephen:  My version of “the butter” is the fact that no matter what I design, at the end of the day, whenever it gets in front of one of my consumers, it is what it is, right? Like the reasons why that butter is hard or cold, the reason why somebody thought about it, isn't, don't matter. There's just the reality of it's in a really good place, or it's not. And I think in a lot of cases, as creatives, we get really good at rationalizing why it works or why it doesn't.

Debbie:  Yeah, the butter has to be cold.

Stephen:  Right.

Debbie:  Otherwise it'll spoil.

Stephen:  Well, and that, right. And that sort of things as opposed to, no, if you set it out and you put a timer there, and again, you sort of think about the details that surround that, then that yields this really good experience. Because, I think, in too many cases, yeah, you can let the process, and the excuses, and the, all these other things sort of overcome the fact that at the end of the day, whenever that butter hits the table, it is what it is. And nobody understands or cares why. So, for me, it is trying to hold myself to that reality. Nobody understands version 2.0, they don't understand why something got cut.

Debbie:  You've stated that you found your biggest career challenge to be getting a clear understanding of who you are as a designer, understanding your unique creative process, and then learning to summon your creativity on demand. And I'm wondering, how did you find the answers to those questions, and how might others begin to do the same? I'm also especially interested in how you summon your creativity on demand.

Stephen:  I think a lot of it, for me, started with, and I see this with a lot of creatives who I coach and work with. I think it's just figuring out how you make peace with yourself. Because, I think who you are, and your background, and all these things that sort of make up your process and who you are, are unlike everybody else. So in many cases, I think people will feel like it's their weakness, it's the thing that makes them different and in alienating, and this is where imposter syndrome and a bunch of other stuff comes from. And part of it, for me, was just saying that one, my past, where I came from, was not changing, but that that perspective was actually my strength. It was what drove me to be different.

Stephen:  And the ability to summon my creativity on demand was really just starting to develop the self-awareness of what do I do whenever I have an idea? I did it, and that worked really well that time. What'd I do? Let's try that again. I worked it, I'm-

Debbie:  What is it that you do? Do you write it down? Do you talk to other people about it?

Stephen:  I mean, for me, it really is, it's sort of very right brain, left brain. I think a lot of it for me is pulling together a visual inspiration, pulling together sort of experiential cues, trying to understand what I want it to feel like, what I want it to look like. At the same point, then it's starting to write down what are the business problems, what are the outcomes, what is the approach, what does this need to achieve? And then start to look at what are the differentiators? What are the easy areas everybody's going to go towards, and say, "Okay, great, we can do that, but, how do we find that insight that maybe not everybody else sees? How do we find something that is a little bit different." And it is just the ability to be comfortable being uncomfortable as I go through that.

Stephen:  The first idea is never going to be my best. That it's going to take some time and work and the ability to again, really sort of work through this in a blue collar craft sort of way to look at what are those answers going to be?

Debbie:  So is part of summoning creativity on demand just sitting down and getting started?

Stephen:  Oh, it's a huge part of it. I think it can start to become much more nuanced. I know if I'm concepting, I can listen to music. But it can't be music that I know. Because I find my brain drifting and sort of singing along with the ... And then I'm getting too distracted. So, I need to put on something I don't understand, or something that doesn't have words. I know that I need to be able to work on that, and really go heads down, but then I need to take moments to step away, and just sort of let it marinate, and not actively work on it, but then, pay attention to what are the little themes that I keep coming back to?

Stephen:  So it's a lot of those things just in myself and my process of starting to look at those, and giving myself the space, and the time, and the permission to do that, as opposed to just sort of bearing down, and saying, "Okay. Be creative."

Debbie:  All told, you were at Starwood for almost nine years. And you wrote, in 2015, "Many people are surprised to hear that I've been laid off from two of my last three jobs. And it happened because of sudden changes in leadership or business strategy that I could do nothing about. If you just read that line, and thought to yourself that you are good at your job, so you are safe, then you are being naïve. I got laid off from my last job right after I designed an app that was featured in three Apple Keynotes, four Apple TV commercials, and generated tens if not hundreds of millions of dollars in free press. But that wasn't enough for me to keep my job."

Debbie:  So, Stephen, how do you regard that layoff today, and what did it teach you? And why did it happen? Geez. So ungrateful. I'm not sure I want to ever stay at a Starwood again.

Stephen:  No, I mean, I think, what it taught me is, is that this is a business. And that what had happened was the work didn't matter, that it was a bunch of people who sat on a board of directors who I saw very infrequently had decided that they wanted to sell the company and they were rich, and they wanted to get richer. And that the CEO who I loved so dearly was pushed out. I was a very visible remnant of that, so I was not far behind. I think that anytime that's happened, for me, it's heartbreaking. I think it's ... You put your heart into that, you put your team into that. And it's taken away. But it taught me that I no longer was just simply going to accept what the industry gave me. I was no longer going to allow that to happen and not have it have consequence.

Debbie:  You were quite candid about being laid off. You never presented it as, "Oh, this was my decision, and so on and so forth."

Stephen:  No. Well, because-

Debbie:  A lot of people do that. They negotiate packages where that is the word on the street.

Stephen:  Yeah. I felt it was important to say that I'd been laid off. I felt like it was ... because nobody talked about that stuff. Nobody was saying, "I have this issue." Or, "This happened to me." Or, I'm heartbroken, and I don't know what to do. I think even I had kind of gone through a mourning period where there was a friend of mine who's a huge, really successful portrait photographer. I had kind of posted this poor me post on Facebook. And he called me up, and he's like, "Dammit, you take that down right now." He was like, "I know you're in pain, and I know you're going through this." He was like, "Look, lean into it, share with people, but you do not feel sorry for yourself."

Stephen:  And I think that that is the start of that sort of part of my career where I just felt like, "Look, why not be honest? Why not kind of say what this was as a ... If I can save somebody else from having to go through what I went through, then it's worth it. And yeah, I've got to suck up my pride a little bit, and I've got to admit that this didn't end the way that I wanted it. But that's fine."

Debbie:  Did you take the post off of Facebook?

Stephen:  I did. No, because I think I needed that in that moment, because I was shell-shocked. It was a company and a team that I loved very, very much. It was heartbreaking to me. I think it's something I still sort of struggle with from time to time to be able to go through that. But, for me, it really was just sort of leaning into the fact, and understanding that we can sort of get very comforted and feeling like, "Oh, it's a family, and they love us, and they take care of us." And yeah, most of the time they do. But whenever it becomes a business, that can come crashing down in a heartbeat to really inflict that reality on you. And if you are unprepared, if you have not thought about what will you do, and I think, yeah, that was the moment where I made a promise to myself that I was never going to let that happen to me again, and if it did, I was going to be ready on a moment's notice to be able to react to it.

Debbie:  So, you didn't globalize, and then start thinking that you were doomed, and your life sucked, and you were never going to find another job, and you were going to be unemployable, and end up dying, face down in the street?

Stephen:  Well-

Debbie:  That's what I do.

Stephen:  No, I think there are definitely moments, where you're just kind of like, "I'm a hack, I'm a fraud, so many other people are so ... " I mean, that happens on a daily basis for me. I think we all go through that. But a lot of it for me, was like saying, "Look, we have done something great." And I was not going to let, give them the power of taking that away. They didn't understand what they were doing. They made a really stupid decision. History was going to tell that story.

Stephen:  And, again, you can look at-

Debbie:  And it has, yes.

Stephen:  ... where that has gone, and I think that it has. And the moment that always stuck with me, and I think the moment that probably saved me was because I was so well known at the company, whenever I was laid off, I was deemed as a security risk. So I had to come in at the end of the day, on Friday, I was not allowed to see my team or talk to anyone. And I walked into my office, and my desk is covered in these like Polaroid photos. And every single person that I had worked with, took a photo of themselves holding up a sign about how it affected them.

Debbie:  Oh, wow.

Stephen:  And I absolutely broke down, right? But it was seeing, like the work was great. But that was the testament to the moment, just that they wanted to know that this, that was the impact that you'd had.

Debbie:  Well, you didn't end up face down in the street.

Stephen:  No.

Debbie:  You ended up joining Citibank. Citi, as the Senior Vice President and Global Head of Design in 2015. And as I understand it, Citi has numerous in-house design teams, in addition to external agencies. Had you worked in those kinds of fragmented environments like that before? It seems like it had been a tall task with a fair amount of cat herding involved.

Stephen:  Yeah, well, I think I'd had some experience with it, because Starwood had 12 different brands.

Debbie:  That's true. That's true.

Stephen:  ... we had 12 different brand teams.

Debbie:  Yeah.

Stephen:  So, yeah, it wasn't that foreign to me to be able to sort of have to plug in plug out of all of those different things. I think for me, though, working in a 300,000 person organization, trying to setup the first sort of centralized design team, doing a lot of those things was very different at scale. And I think also just, that role is sort of the first in a 210 year organization. The muscle memory to the old ways of doing things tends to be much stronger.

Debbie:  What was it like, having to communicate in the world of finance versus the world of lifestyle at Starwood versus Citi?

Stephen:  I think what I tried to bring to Citi was the same thing that I had learned at Starwood. That at the end of the day, at Citi, what we weren't doing is we weren't talking to our customers. We had kind of said, "We understand who they are, and we have personas." And for me, it was like, "No, look. We need to get back to having them be the source for truth. We need to understand what do they want." And so, kind of putting the consumer a little bit more back at the center of the work and trying to cut through some of the politics, and a lot of the red tape, that was sort of the thing I was able to bring in there, to be able to help, kind of change things there a little bit.

Debbie:  When it comes to executing really big transformations with companies, as you've done, where do you tend to get the most push back? Is it the C Suite? Or is it the consumer?

Stephen:  Oh, it absolutely is internal. Because I think the consumer, at the end of the day, if you're able to deliver something for them that meets an unmet need, they'll always kind of go along. Like, they may buck against it a little bit, because if it's a change, they aren't sure that they like that, but ultimately, they'll sort of go along. No, I think that in many cases, what I've found, is whenever I come into organizations, whenever I come in, I will try to make sure that I have executive buy-in, I know how to work with the team, and to be able to sort of get them behind me.

Stephen:  It's everything between my team and the executive leadership that's the problem. Because, I think for a lot of people ... I used to have a poster that sat in my office that said like, "Comfort is the enemy of greatness." Because in many cases, people just want to do what they've always done. They don't ... They want to be right, they want to be in control, they want to do what they know, they are very afraid of change, and a lot of those sort of things. So that's what that push back is. And so a lot of it is how do I create structures to bring them into the process? How do I kind of be the Sherpa in the creative process to still let them come along and take some of the credit? And to do those things that I know, it's almost like organizational Kung Fu. Like, how do I use their momentum back against them, and give them what they want, but sort of effect this change in a way that they maybe aren't completely aware that it's happening.

Debbie:  Paula Scher famously said that, "Clients don't give you the big bucks because you are a big agency or a big talent. They give you the big bucks to navigate through all the stuff that they have to have you understand and try to get through."

Stephen:  Right. Well, and I think that's ... Because, for me, the thing I'd always tell my team and when you want to do organizational change, is you have to remember everybody's creative. If you walk into a kindergarten, you'll see everybody's a painter, or everybody's a singer, or everybody's a superhero. Our education systems, our society, all of these other things have sort of gotten in the way. And have let us forget that we were creative, or we've become uncertain or scared of it.

Stephen:  So the ability to sort of bring people back into that, to make it comfortable for them to be able to show them that there is a way and a structure to be able to do it, they will. But you have to sort of get them over that fear.

Debbie:  Reflecting on your time at Citi and Starwood, you said the following. "I've learned to build brands that people hate." So tell me more, and are you okay with doing that?

Stephen:  No. Absolutely. I think whatever it's come to my own, personal brand, that's what I try to do. And again, I think it's purposely meant to be a bit of a shocking statement. But I think the idea is that for most brands, whether they are personal, or whether they're for companies, people will try to like, "I want to please everybody. I want everybody to love me. I want ... " And that's just not real. And so, in many cases, for me, the ability to say, "I want to build a brand that somebody hates." Is that it stands for something that is strong enough, it has beliefs that are clear enough.

Stephen:  It has a point of view that is distinct enough, that somebody can say, "Yes, that's for me." Or, "No it is not." And I think whenever you looked at the work we had done at Starwood, that was very much what it was about. W was about design, music, and fashion. That is absolutely for some people. Other people are like, "Look, I'd much rather go to a St. Regis, or a Weston, or a Sheridan." And we build out lifestyle brands around that. But for me, it's just trying to force that clarity, that perspective, that consistency, but also, that kind of forced a perspective that, "Look, this is what we really stand for."

Debbie:  You have mentioned a few times over this show, now, the notion of a personal brand. And I often have squeamish feelings about-

Stephen:  Sure.

Debbie:  ... that term. Mostly because I define branding as manufactured meaning. And so, if it's a personal brand, then, you're manufacturing meaning for yourself, and the way you are positioning yourself in the world. I tend to like to think more about reputation. But tell me what you believe personal branding is or isn't.

Stephen:  Yeah, I think that for me, a personal brand is the ability to just say, "This is what I stand for. This is what I believe." But, if it is manufactured, then that absolutely is a failure, right? Because I think, for me, and this may get into nuance, I think reputation for me was a little bit more about are you sincere in the way that you go about things? If you say you were going to do something, do you really do it? The personal brand for me is something that I come back to a lot, because I see almost no creatives understand it or invest in it. I think that for me it starts with understanding what is your perspective, what is your process, what is your voice, what do you believe? I think those are three of the interview questions I would ask most often of people, is can you tell me how you have an idea? Can you tell me what you believe in and what your brand statement would be, and can you tell me what you need to be happy?

Stephen:  Almost no one can answer those questions. People have come back like three days later, saying, "I haven't slept, because I don't know the answer to those." But-

Debbie:  Those are big questions.

Stephen:  I think, for me, you can see ... I would argue you can see the reason for the need for personal brand. Open most any resume. Open most any portfolio. Talk to most any person. And what you see is a list of where it is that they've worked and where they went to school. That is not who they are. That is not who I want to hire. That is not what you are putting out into the world. But in-

Debbie:  What would you rather see?

Stephen:  Who are you? What do you believe? What makes you different? What are the things that you want to bring to the team? Because for me, I met tons of really, people who have the best pedigrees, gone to the best schools, and worked at the best places, who couldn't [inaudible 00:50:29] a boat and hit water whenever you asked them to be creative. But I've seen other people who have worked at none of those who are absolutely brilliant. So, for me, the personal branding, the idea behind that is just simply the ability to say, "This is what matters. This is what makes me different." Because we do it no matter what.

Stephen:  Whenever you go into a job interview, you're trying to figure out, "Is this is a good fit for me or not?" But we do that very privately, because if you do it publicly, and you say, "This is what I stand for." Well, maybe people like that and maybe they don't. And if they don't I'm not sure how I feel about that.

Debbie:  Absolutely. Absolutely one of the things that I encourage both my undergraduate and my graduate students to do, is to create a mission statement. What do they believe in and why? And that is constructed from knowing what their strengths are as well as the areas that they might actually think are weaknesses, but very well may be what helps to differentiate them in a really powerful way from a creative perspective.

Stephen:  Right. No, and that's why I said, and I think, for me, the nomenclature, whether it's a brand or a statement. But, for me, it's taking the time to do the work. Because I think I see so many creatives who don't have any understanding around that, who don't understand what do they bring to the table, or even what do they want?

Debbie:  What is the benefit that they bring?

Stephen:  Right. And I think-

Debbie:  That's the most important question.

Stephen:  And whether it's, it will help you in the job that you're in today, it's going to help you in the next job that you get. But having that sort of clarity in saying like, "Look, this is what matters." I think is really important. Because if not, the, yeah, you're 20 years into your career going, "Look, I don't understand why I'm not happy, or why I'm not getting the jobs that I think that I want."

Debbie:  How did I get here?

Stephen:  Right. And so, yeah, I think that, that for me, is why that becomes so important.

Debbie:  In 2018, you left Citi for InVision, where you've been for the past year and a few months. As you said at the time, "When I was looking around, the only place that made sense to join was InVision." So I have a couple of questions, here.

Stephen:  Sure.

Debbie:  First, what exactly does InVision do? And what made you want to work there?

Stephen:  So, what we do, is we create the tools that if you're creating any sort of digital product, an app, a website, anything like that, it started with, and most people will know us for it gave you the ability to go in and prototype that. So, the ability to put the designs together, to be able to look at it, try it out, put it on your device, see what it looked like, before you invested in a whole lot of code and things like that. I think in the years since, it really has become a truly connected workflow. So, the ability to have a three or four hundred person whiteboard, all the way through how do you hand your designs over to your technology team. It's an entire kind of suite of tools to be able to do that sort of work.

Stephen:  And I joined, one, because I felt like whenever I was looking at the industry and what was going on just in digital tooling, I felt like they were really getting the trends and looking at what was going right way more than anybody else. And the fact that they would recognize the rise of things like design systems or kind of the need for being able to do high fidelity prototyping, things like that.

Stephen:  But, how it started was it was a job I wasn't looking for. I ended up, had decided I was going to leave Citibank, had kind of strategically reached out to a few people. Clark from InVision, who is the CEO, if you ever around, that everyone gets e-mails from Clark from InVision, they always want to know if he's a real person, which he is. He and I had a conversation. He just said, "Look, what do you see is going on in the industry, and where, what should we be doing?" And I said, "Look, there's a lot of great tools out there." But as I look at the industry, what I think is holding teams back, is their ability to understand how they deal with everything that surrounds that work. How do they get better at politics, and business strategy, and elevating the impact of design and doing a lot of things like that?

Stephen:  And he said, "You know what? I completely agree with you. Can you write a job description and go fix that?"

Debbie:  14 pages long?

Stephen:  Yeah, well. And, so, off we went. And that's really kind of what this was about, was that as we sort of ... We look at the world through these sort of lenses of people, practices, and product. And product is obviously applications that we make, and I will tend to focus more on the people and the practice side of going in and working with our customers, and say, "Look, how do you elevate the impact of design? How do you empower your design team?" How do I do what I've been doing at Starwood and Citi, but be able to come in and sort of bring real expertise, not sort of like, "Hey, I read a bunch of papers and saw a Ted Talk." But really the ability to elevate that impact of design inside of these companies.

Debbie:  You started as the Head of Design Transformation. What were you specifically brought in to do?

Stephen:  So, for me, it was just really that. It was building out a team to say, "Okay, how do we go in, and provide coaching, to provide workshops, to be able to provide those sort of things, those sort of services for our customers to be able to get them the help that they need?" And I think it was the first time I had left being a designer, or head of design behind and be able to build out a different team like that. But, one of the things I really love about it is also sort of the very daring move that InVision was founded, and we have no office. We're the world's largest completely distributed company. So it's about 800 plus people and zero offices.

Debbie:  Where do you work?

Stephen:  I work out of my house.

Debbie:  Oh.

Stephen:  As does most everybody else.

Debbie:  That's so cool.

Stephen:  And it gives you the ability to, then, kind of go through and say, "Okay, look, I want to hire the best people. I don't really care where you live."

Debbie:  You said something in 2012 that I want to ask you about, given your current job. You said that respect for designers was down, because technology and social media had put creative tools in everyone's hands and stated this specifically. "Many creative professions have been devalued, because people confuse the executional act of creation with the creative process of creating something that has lasting meaning." Do you think that this has stayed the same, or has changed?

Stephen:  I think the sentiment, I still agree with. I think my perspective has broadened, over the resulting seven years, that I think, in many cases, there still is a confusion between the actual act of creating a visual design, and sort of going in and doing the executional piece of that with the creativity and the ideation of it. But I think that was the start of a line of thinking that for me, in many cases, design has evolved in many spaces from being visual design to being more product design.

Stephen:  So with that has come the need to be a more inclusive in your process, to bring in product and technology, to understand data, and research, and it's just a lot, it's become a lot more sort of nuanced. And I think, as an industry, this is where we struggle. Because so many of the design leaders are still sort of stuck back in visual design. And they aren't sure how to break through, they aren't sure how to sort of elevate that impact.

Stephen:  We recently did a study of kind of looking at, it was the largest sort of global study of design maturity, where we saw like 83% of the world's design teams are sort of stuck in the middle to the bottom on design maturity. And I think it really-

Debbie:  What does that mean? What aren't they doing?

Stephen:  I think what they're not doing is they can't figure out how do they transcend what they're doing to have organizational impact. They're good at transforming their teams, they are good at being able to be able to do better looking work. But whenever it comes to creativity, whenever it comes to how do I get my peers in other disciplines? How do I get executives to truly value and understand what we do beyond the quote unquote make it pretty, the ability to do that sort of breakthrough, and break through organizationally, or if you have that seat at the table, to leverage it to real impact. That's the place where, that a lot of them are really struggling.

Debbie:  If you had one piece of advice to give those senior creative directors and VPs of design that might be listening, what would it be?

Stephen:  Go out to your partners and ask what's keeping them up at night. Because, I think, in many cases, what we do, is we'll kind of say, "Oh, well, this is the challenge we want to take on." Or, "This is what we want to ... design a beautiful button, or we want to do this sort of a thing." Go out and try and figure out what is keeping them up at night? What are those sort of business challenges that they have? What are those sort of things? And then, how do you go to help them, to demonstrate, one, what you're value is, but to also bring a different approach. Bring in design thinking or design sprints. Bring in some sort of a creative process to help them be able to really achieve those.

Stephen:  Because I think in many cases, they're struggling, and can't figure out how to break through and get to do that. And again, instead of sort of siloing those two things off, figuring out how to come together to solve it.

Debbie:  Stephen, the last thing I want to talk to you about is your podcast. You started the Crazy One Podcast in 2016, which has been described as the Tony Robbins' audio series for the design community. What motivated you to do this in the first place?

Stephen:  I think I had spent, I don't know what, 10 or 12 years going through and doing public speaking, writing blog articles, doing a lot of different things like that. But, I had this sort of one seminal moment, where, a couple of years ago, I was at an event in Europe, and had decided that I wanted to do a really personal story. I was going to try to take the mask off, I was going to try to be more honest and open about what I'd been struggling with in my career. And I had a young man who came up to me, after the event. And he was sort of very hesitant to talk to me, and once we started talking, started crying.

Stephen:  And he said, "Look, I, if I'm being truly honest, I want to be a designer, I want to be creative. And the talk that you gave was the first time I felt like I heard somebody be honest. It was the first time I felt like what I was doing was right. Because I'm in a place where either I'm going to become a designer, or, I have to go against my entire family. They've said, essentially, "If you go and become a creative, we're not going to support you, we're going to shun you."

Debbie:  My God, that's harsh.

Stephen:  Oh, it got worse. And I think, he said that it had gotten to the point with him where he was so conflicted, and was so afraid of being alienated that he sold everything he owned to buy this conference ticket. And that he was either going to be two outcomes. Either one, he was going to decide, he was going to go become creative, or, he was going to go to a bridge outside of town and kill himself.

Debbie:  Oh my God.

Stephen:  And I was and remain speechless. I never thought that me sort of talking about what I had been through would have an effect to that level. And so, I came back, and I was just completely focused on the fact that like, my message needed to change. Me writing articles, and me staying out, it wasn't enough. And so, the podcast was born out of that, to try to take on the issues that I felt like people weren't talking about. To take on and really share, and sort of be vulnerable about that, trying to hope that at some point, I would be able to kind of get to that next kid, or that next person, or at least encourage others to honestly share their stories, because if anybody in the world was at that place, over being creative or not, just something had to change.

Debbie:  Do you know how that young man fared?

Stephen:  No, I still keep in touch with him.

Debbie:  You do. 

Stephen:  I helped him. I kind of have taken him under my wing and continue to sort of try to help tutor him. And no, he's got a great design job. He, in Germany, he ... I think his family has started to kind of come back around that. And I think, for me, it really was just, yeah, wanting to kind of share more and to try to help force more of these conversations.

Debbie:  The name of your podcast, The Crazy One, came from Apple's famous Think Different ad, and the line, "Here's to the crazy ones." You also, I believe, you have the words tattooed on your arm?

Stephen:  Yep.

Debbie:  Yeah, I thought I saw that there. Tell me why this means so much to you.

Stephen:  I think because I spent, I don't know what, 38 or 39 years of my life just being too consumed. And like I said before, of trying to be what I thought everybody else wanted me to be. And it wasn't until I was at Starwood and started to find success, where we had started to work with Apple and do things like that, that I realized that all the things that I kept feeling guilty about, all the things that I thought made me lesser were the things in a different context that made me truly stand out and excel.

Stephen:  Yeah, the line is from the commercial. It, and it's funny, many people at Apple have no idea I have the tattoo, because I usually cover it up. It wasn't meant to be kind of a fanboy moment. It was meant for me to, every single day whenever I look up, and look at my right arm, to remind myself, how I need to show up, how I need to be present, what my mindset needs to be. Some days it's an affirmation, some days it's a reminder. But yeah, it was, for me to just kind of say, "Look, I need to show up and be honest in who I am." And, yeah, the tattoos on both of my forearms, are reminders to that point, so that I never forget and go back to that place again.

Debbie:  Stephen, my last question for you is about something I discovered in my research that really surprised me. Apparently, almost a decade ago, you had a food blog-

Stephen:  Wow.

Debbie:  ... called The Rusty Foodie.

Stephen:  You went deep on that, yeah.

Debbie:  Which documented things like how to make the perfect mango caviar, which sounds really good.

Stephen:  Yeah.

Debbie:  How much cooking do you do these days, and why did you stop writing it?

Stephen:  I-

Debbie:  And what's the butter like in your house?

Stephen:  So, the butter is French. It's always French. There's certain things. It's like milk is always whole, butter is always French unsalted, just because that's just the way life should be. It was. I've always been a huge cook. I think I've actually trained, and I'm like a trained butcher. I've gone to cooking school, and different things like that. It's sort of interesting. For me, it's just become an outlet that's way cheaper than therapy, because in the time horizon that I deal with a lot of my creativity, the ability to start and finish something that is creative and that I love in the span of an hour or two, is incredibly satisfying, and I did. I became very enamored with sort of like molecular gastronomy, and the kind of modernist cuisine, and started to push the boundaries around that. And had decided I wanted to kind of start being able to write about that, and just realized I was running out of time, or sanity, or things like that, and had kind of put it to the side for awhile.

Stephen:  But, no, I think I'm still cooking multiple nights a week, and it's funny, a lot of the speaking schedule where I decide where I'm going to go talk in the world is based on if there are restaurants that I want to go to, or chefs that I want to go meet.

Debbie:  Well, Stephen Gates, thank you so much for joining me today, and Design Matters. And thank you for really trying to make a difference with your work.

Stephen:  No, thank you so much.

Debbie:  You can find out more about Stephen on his website, That's Stephen with a P-H not a V, and on his podcast, The Crazy One. This is the 15th year I've been doing Design Matters, and I'd like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I'm Debbie Millman, and I'm looking forward to talking with you again soon.