My guest today is Gordon Ching who is the founder of Design Executive Council (DEC) building the network dedicated to advancing the design executive profession in Silicon Valley and beyond. Interview Video: https://youtu.be/Hm10bL4VTTk In this episode, we discuss the following: - Why I'm interviewing Gordon Ching - Why start Design Executive Council? - Why is being a design executive not a glamarous gig? - Why can't a design executive focus on design all day? - Why does a design executive need to develop their judgement? - Why does being a design executive feel lonely? - Who are the current members of the Design Executive Council? - Advantages of IRL meetings over Slack - What are some of the tough decisions a design exec has to make? - Real life example of a design exec demonstrating high Emotional Intelligence (feat Andy Vitale) - Why traditional design career ladder doesn't apply for design executives? - How do design executives level up? - Adopting ownership mentality in your career For show notes, guest bio, and more, please visit: www.designmba.show
Gordon Ching is the founder of Design Executive Council (DEC) building the network dedicated to advancing the design executive profession in Silicon Valley and beyond. Through the DEC, Gordon is partnering with chief design officers and design executives of the world’s most successful public companies and venture-backed startups to advance the relationship between design and business. Gordon was previously at Affirm, Fast, Synchrony, Apple and AIESEC International.
INTERVIEW VIDEO:
https://youtu.be/Hm10bL4VTTk
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Namaste and welcome. I am Jayneil Dalal and you are listening to the design MBA which is a real-life MBA program for designers. You will learn how to launch a side hustle and level up your design careers from the interviews rock star designers.
Jayneil Dalal: Folks, whether you're listening to this amazing episode or watching it, I'm super excited to tell you today's guest is Gordon Ching. So, let me tell you how I got excited getting Gordon on the show. So, on my LinkedIn feed, I saw Gordon post about this dinner with amazing, amazing set of design executives that a lot of you know from companies like PayPal and so many different famous companies and I was like “What is this dinner of all these design executives that are gathering together?” And then I saw that “Oh wow!” There's this group called Design Executive Council that is hosting these dinners and the founder of that is Gordon Chang and he is a Canadian design operator and management thinker. He's worked at amazing set of companies like Affirm, Fast, Synchrony, Apple. He’s also got a Masters from SCAD. So, then I was like … I reached out to him and we had a prep call and we were like “Oh my God! We need to talk about what it's like to be a design executive.” And what I told on our prep call was that “Can you give us and our listeners a behind the scenes look at what it really means to be a design exec, stripping away all the glamor and all the fancy titles and stuff?” So, that's what we're going to be focusing on today.
Gordon, thank you so much, my friend, for coming on the show.
Gordon Ching: Jay, thanks for having me. It's a pleasure.
Jayneil: You know a question that I've been dying to ask you … and I haven't asked you yet, right? By the way, fun fact for everyone listening. Me and Gordon, both are Canadian. I spent some time in Toronto. What was that for you?
Gordon: I spent one year there in Toronto but I'm born and raised in Vancouver where it's a little warmer. Toronto was far too cold for me and this is why I live in San Francisco.
Jayneil: Same. That's the reason also why I moved out. It was too cold for me. So, the question I had in mind was like most people would think that design executives probably network with each other at, let's say, a design conference or maybe message each other or just run into each other. So, what made you, you know, like start the Design Executive Council?
Gordon: I think the thing I've learned is all these executives sort of know each other by reputation. They're all very visible people in our industry but the biggest difference is how deep can you go in these conversations and have a peer-to-peer level of depth in talking about things in a very open and honest way. And so, when I finished my initial set of interviews for my thesis during my Master's at SCAD, unknowingly hosted a dinner that was simply to thank everyone for participating in my research. I left that dinner going “What?” like everyone were sharing and so openly and you saw this camaraderie and sense of kinship. And some people were kind of saying “This is like therapeutic to be able to meet people like me who understand all the challenges I have.” And so, even though executives might know each other by reputation, they haven't had the deep intentional spaces where you can free flow share and feel safe and that was really the start. It was a dinner to thank people that morphed into an open space for honesty and helping each other as peers.
Jayneil: Oh my God! So, based on that first dinner, basically, you tested her idea and you were like “You know what? I can have another dinner where maybe I invite even more design executives.”
Gordon: It's like a thing where you literally is spontaneous like where you host the dinner to say thanks but at the end of dinner, everyone's like “Gordon, are you going to do more of this like is this the last one? Can we get more?” And knowing these are people I really respect, I'm like “Oh, you want more. Okay, let's make it happen.” And so, a year later we had our first official dinner as the Design Executive Council. Before that it was just Gordon as a student hosting a dinner that then we realized there's something here that might be repeatable for many more design executives to benefit from.
Jayneil: What I really love about the unique position you're in is that you're able to interact with all these design executives in a safe space where they can safely tell you what it's like because there's something a design executive can share on a public stage in front of so many other designers and there's something they will say you know candidly with you behind closed doors is trusting. So, you probably identified a lot of themes, not to say that what you're sharing or what we're talking about in this interview is going to apply to every single design exec but, you know, there are themes. So, one of the things I'm very curious about is why is being a design executive not that glamorous.
Gordon: The way I wrote this in my research was growing up, my mental model of a design executive, the only one I really knew was Jony Ive of apple. He was designing at Apple for many years and we know him through his iconic work but when we think about how he designs, he's the one in front of the stage like narrating those beautiful videos, talking about the love and craft for design but you don't hear anything about management like what was it like to scale the entire design organization. And so, when I went to these dinners and got to know design executives, I realized my mental model of what a design executive is was so glamorized. I imagine this person, this beautiful studio just getting quiet time to make these beautiful things but as I got to know more of them, I’m like “No, they're dealing with resourcing, headcount, budgets, politics, cross-functional relationships,” thinking through all these things that you might not have traditionally associate with a design executive. And when I learned these things, I was like “Wow!” like “This job is a lot harder than you think. It's not just you get to sit down and go heads down and go really deep into your craft. No, you're like holding the entire organization at bay, right? And trying to muster the resources to keep it going year after year and to think ahead and be strategic. And so, when I learned these things, I had to reshape my own mental model. So, it's a whole image in my head that had to like change. And I think sometimes we've held ourselves back because we associate it with this concept of what we call the genius designer, a single individual responsible for everything and making all the beauty and excellence come to life when in reality it’s actually a team of designers with many more facets and dependencies and stakeholders. And so, that changes the equation of like “I'm a lone genius who disappears in my own little studio” to someone who's a little bit more open and collaborative because now you're working in a company with many types of discipline.
Jayneil: I really caught on to what you just said there that these design execs have to do not just design work but a bunch of other things like headcount, like talking to Legal. So, a question I am very curious about is like, you know, as an IC designer I can choose just to focus on the craft and not have to worry about, you know, talking to legal. So, why can't a design executive just not stay in their lane of design? Why do they have to like go horizontally across all these other things?
Gordon: If your head's down in your craft all day every day, you're not looking out. Think of a sailor. If you're just heads down not looking at the horizon, you don't know what icebergs are coming, what the storm or weather looks like. And you are now a captain. You have to steer the ship and that includes all your teammates, right? And you're the single person who can decide “Do we hire or not hire? Do we get more resources or not get more resources?” So, this really changes the way you operate yourself. You no longer have the luxury of just being heads down. You need to be heads-up, looking left and right to spot the threats, the opportunities and really know how to execute against that insight that you develop as an executive. So, that's a huge mind shift, right? Even when you're jumped from IC to Mac for your first manager role, you're now having to interface with so many more stakeholders to think about resourcing, planning, etc.
Jayneil: It sounds so different because when I think about my role as, you know, going back to the IC design, it’s very much task based like make sure the wireframes are due by this date. It's very task based. And what you're describing does not at all sound like task focused.
Gordon: I think about the more senior you become as an IC, you do participate in strategy but at the end of the day, you are also accountable to the quality and delivery of that work, right? So, there's a clear output from an artifact standpoint. As a design manager and executive, the further up you go, you're having to hold instead of one jar, you're now holding like a hundred more jars. How do you repeat and scale yourself to affect so many different units in your business, right? So, you're going to have to now develop systems, methodologies, processes that work at scale. You kind of have to replicate yourself if you think of it that way. How do I turn Jay who has a set of point of views, a philosophy and replicate that times whatever number that needs to exist in the organization, right? And I think this is why it's also so exciting to see the rise of design operations because we're now thinking about scalability, repeatability and these are core things in making sure that we are effective. Restarting every time try to teach someone, that's not efficient or wasting a lot of time.
Jayneil: As you were mentioning all that like, you know, taking Jay from what he's doing here to like things at scale, you know, for me, if I'm stuck in something, I can always watch a YouTube tutorial about some specific Figma function, I can take a course, talk to many of the designers and the stakes are not that critical where like if Jay doesn't figure this out in the next 48 hours, it's going to be all right, the world's not going to end, but now I'm trying to put myself in the shoes of the audience you're interacting with, the design executives, a lot of them is doing this for the first time and so many things are at stake. How do they learn all these things? That's my biggest question like do they just figure it out on the go? I mean, what if you make a mistake then?
Gordon: Here's the thing. the further up you go, the stakes become even higher but the answers are also more unclear. That's why you're in that job. And the one thing I really think about nowadays is the key word is ‘judgment’. What is your judgment to make different types of calls even though they're imperfect? Because if you think about any business, you're having to make these daily decisions have all sorts of consequences. And you won't have time to watch YouTube videos all the time about every subject or even read every book about every subject. It's impossible. It's learning to embrace that there is no perfect and that can be really scary. You're having to make decisions about so many different facets without having 100% readiness on anything. And so, you need a lot of conviction and courage but it's also why you're hired into that role is you've developed a set of experiences that you can lean on, perspectives that strengthen your own ability to make a judgment call. And there's going to be times where you're like “I only know 20% of the information and I have to make a judgment call because there's a deadline I need to meet.” And there's going to be other times where you have a lot more luxury of time but this is the thing, right? As an executive, your time is so scarce and strapped across so many different areas, so you're going to have to place your bets on where you invest a high degree of time and investment versus “I just don't have time for that. I need to either delegate it or make a judgment call.” And that can be really uncomfortable.
Jayneil: It is because, I mean, it's like so tricky waters because like when I have to make a judgment call on whatever I'm doing, I have … like my manager is going to challenge me or course correct me if I were to make a mistake or if I'm making the wrong decision but who is there doing the similar role for these design executives then?
Gordon: That's why it can feel lonely. Who are you checking this with? When you get out there, they're expecting you to be autonomous, they're expecting you to be an owner. And so, they've given you the ownership of the design department. You are the person who has to make all the decisions. And I think a little bit like the journey of a founder like what I'm experiencing now. I had moments where my team is like “Gordon, that's your decision now.” I'm like “Oh shit! I'm accountable.” And that's the same feeling any executive, design or other places, they will be the owner and they have to make that decision. And so, that can be really unsettling because I don't think we grow up being used to making that degree of, you know, decision making. And so, that to me is a big chasm that we have to cross to grow into our ability to be an effective manager.
Jayneil: And also, something I'm thinking about is because of job preservation or many of the reasons or title, the candidness with which my manager will challenge my decisions, you know, it's not going to be that straightforward. I don't think everybody in the design team is just going to like straight up challenge their design executives. There's going to be some fear or hesitation. So, that kind of makes that judgment call even more difficult because people are afraid to confront you or openly challenge you, I guess.
Gordon: Yeah. And if you think about it, there's a distortion field around people we admire or people that are powerful. Think about celebrities like there's some distortion field around them when people interact with them. And so, I think a little bit to an executive in the hierarchy of an organization is they have that kind of celebrity status. And so, it can be really difficult for them because they become more isolated, they don't get the honest feedback, the truth because people are trying to cozy up to them, they're trying to complement them and make them feel good but in reality, that's the opposite of what they need. Because they are making high stake decisions, they need truth, they need to be told “This sucks” and that doesn't happen very often because we're afraid, right? And so, that's why when you think of the word ‘trusted’, there's a very important circle of people that they will build trust with that becomes their confidants to think through really critical difficult decisions but more importantly, it’s like they can't also rely only on their organization. They have to go outside. And this is where when you've reached to this level, the true resource for you is actually outside the organization, outside the company. And this is where at the executive level your ability to network with your peers, find other people like you in similar situations but can offer you a third-party view that's more neutral, honest, that is super, super valuable and that's kind of the premise of why I thought dinners … Design Executive Council, bringing these peers together is a crucial resource for these people to make better decisions at the end of the day.
Jayneil: And can you just give like a glimpse of like like who comprises right now of the Design Executive Council like who makes up the members right now?
Gordon: Yeah. So, our focus is right now a mix of two key audiences. Number one is chief design officers of large public companies. So, these are companies with some of the largest design organizations and design maturity. And then number two is what I call emerging design executives. You are likely a VP of design doing your first design executive job and you're most likely at a scaled startup, a recently IPOed company and it's really your first rodeo being the very top authority of the design organization. And so, these are the two audiences that we're working with to mix and match because the first-time design executive is freaking out going “Oh God! This learning curve is so steep and I have to figure out how to make this work. And a lot of the information is not going to be available on the internet and I need to find peer.” And at the same time, the most experienced design executives are like “I would love to see design in a better place. So, how can I help the future generation?” And they also learn in return because there's reverse mentoring that happens. It's not just a one-way street. And so, this has been the core focus of the council is to tap into the wisdom, the experience, the insight of the most experienced design chiefs all the way to thinking about the next generation and how do we make sure they don't make the same mistakes or at least make them more gracefully so design doesn't suffer as a result of their decisions.
Jayneil: This is phenomenal. Oh my God! We have so many, I would say, platforms where designers like normal just like senior designers or junior designers who can get feedback like ADP List and so many other but what you're creating here is specifically for that exec level. And I'm curious to know like are there any plans to expand this outside of the Bay Area or SF?
Gordon: Right now, the primary focus is making sure we have a high-quality model for even in the Bay Area. And that's been a lot of thinking like all these execs are involved in the co-creation of this concept. So, we want to nail it and we have multiple events this year to really test that out. And once we figure that out, we want to bring this to more cities around the world because the number one thing I've learned is the Silicon Valley San Francisco air is we're really lucky, we have the highest concentration of design people. And so, it's much easier to access the information that you might need to do your job well and feel also the confidence because you have a peer group but I think about the designers in Boston, Atlanta, Miami, all sorts of other cities or Dallas or maybe in Toronto or Vancouver or maybe in London, like the concentration is a little different and the culture is a little different. And so, I see the Design Executive Council actually being incredibly valuable outside of this area because of these geographic realities and where talent is concentrated right now. And so, I could see one day all these people from all these different cities get to come to the Bay Area and interact with some of these most experienced design executives to initiate knowledge transfer. And so, hopefully, there's this continuous transfer of knowledge, intergenerational sharing so that we're up-leveling the talent base of the industry.
Jayneil: And there's a big component that I'm sensing from this which is about physical, in-person in real life meetings that are happening. I mean, now, we have so many companies that are completely working remotely. So, have you thought about like just ditching the in-person model and kind of going like just remote so that you can scale even faster?
Gordon: The number one thing I think about on this one is the feedback is I am so overwhelmed by these giant Slack communities. And we've had many of them over the last years because we've gone remote and it's a lot easier to scale on Slack but the issue is you don't get to really build that trusted relationship on Slack. It's not the same when I can eat face to face next to you and share a meal and really get to know you as a human being. I get to know Jay as a person, not just an executive. And that's the magic that does not happen on Slack. That can be good for retaining the engagement and maybe more targeted discussions but I think about the audience I'm talking about, I'm like they're already overwhelmed with emails and more messaging, I'm like “I think they need a break and to just get in person.” And so, there's a component of virtual that I'm trying to think through but I have not found the answers yet to do it gracefully. The priority for me has been these IRL connections because that's the irreplaceable. It's very hard to just replicate another IRL network that … it's not just like spitting up another Slack. There's so much more relationship building, understanding the context and then doing the right matchmaking so that each dinner conversation is really valuable.
Jayneil: Oh my God! That is so important, just the matchmaking part of it. And going back to just like the thread we were talking about earlier is that the tough calls that design execs have to make, right? The Judgment that you're talking about. Can you give examples of like what are some of the tough decisions that a design exec has to make?
Gordon: I think about, right now, look at the shape of the economy, think about the financial environment. Design executives are now faced with making really hard calls on resources. And because a lot of them don't directly control the treasury, they're given a budget. And so, what happens if you initially had 120 dollars but they're now like “Look, we need you to bring it down to 80 dollars.” What are you going to do? That's the worst feeling. You know, I've developed a different sense of, I guess, empathy and compassion because while it's … I've been through layoffs and it's awful on the individual. It's not a great experience. At the same time, there is someone having to make decisions for the business and like trying to imagine myself in that position of like these are people I like, I care about, I know them … all sorts … I brought them even possibly into the organization and I have to consider who'd I have to let go. And I listen to these stories and I empathize because I think sometimes we look at these execs and we're like “They're just probably these cold-hearted people” but I'm like “They're also people with lives and families and friends and they also have to make these decisions.” And this is the reality of that job. You're now part of a system that unfortunately at times needs to change and that comes with making really hard calls. So, when I hear and see the emotions of this group, that's where I have a new lens of empathy and compassion. It's weird. You know, when I was just on the other side, I feel like “Man, like how do they make these decisions? This is so awful. Why am I getting laid off?”, that kind of feeling, right? But it's always like when you walk in the other person's shoes, you start to realize it's not personal. It's a business decision. And that can be really difficult.
Jayneil: The more I hear you describe the difficult decisions that a design executive has to make, I almost wonder like one has to be like just a little bit crazy to like really go after this role because it's it requires so much out of you making all these tough judgment calls.
Gordon: I think about even world leaders like they're making decisions on behalf of entire countries. And I think a little bit … it's a very small scale. The design exec is making a decision on behalf of their own country, right? And no one's perfect. Every human is flawed and I recognize that situation of like “Yes, no one's going to make 100% perfect decisions” and this is the reality of that job and. So, to be effective in design, you really need to have your own inner compass because you can get lost so quickly because everyone is asking so many different things of you. You're going to be pulled left and right. And if you don't have an inner sense of intentionality, a sense of gravity, you're going to like thrash. And when you thrash at that level, everyone else feels it. When a design exec is not in a good mood, it affects everyone else. So, I think about this concept of their own inner character and kind of strength really matters here because now everyone is looking at you and your body language, your words, how you show up to the room. All play a role. I've been in meetings where they're like nervous and you're like “Oh God! I'm nervous now.”
Jayneil: No, I've literally heard something like the exec will come in the room and they'll be like “Oh, this exec is sad today” and suddenly like they're reading so much into it, there's almost like the exec has to be jolly all the time because who knows what people are going to read into it.
Gordon: Well, I think it's not saying you've got to be happy all the time. That's really unrealistic. I think the more important thing is how can they be honest and candid because that's what people really need. That's a really hard thing is like how do you foster an organizational culture that allows for intellectual honesty and also psychological safety. You don't want an environment that's complacent and everyone feels safe and warm but at the same time, you're not getting the real hard facts and insights that you need to be better or to make better design decisions or think about in a design review. When everyone's just a little bit cozy and too comfortable and not sharing the real issues and feelings, then no one's improving, no one wins, we protect our feelings for a minute but we don't gain from that interaction.
Jayneil: But see, that's what happens like when we are working on like a non-executive role, it's like we try to find people who are nice like, you know, they're not that blunt, that straight up like always telling us the honest truth even if it's like really ugly but then when you step into this design executive role, it's like you want to seek out those people that will tell you the honest truth and not try to be diplomatic or nice to you just because you have the title.
Gordon: It's a fair balance, right? So, no one wants to work with an asshole. You still want to be a kind thoughtful human being. At the same time, it doesn't mean you can't be honest and direct. And so, I think about this tension … and in my thesis, I call this the omnipresence of dualities. It's this constant presence of two forces. And in this conversation, we're talking about safety versus honesty or in a design sense, it's like there's chaos and order. And as an individual, as a decision maker, you have to constantly navigate this tension between the dualities of any situation. You can kind of identify them and then figure out like “Okay, Gordon, like what do I really need to make a decision? What am I optimizing for? Is this moment a moment I need to prioritize safety or is it a moment I need to prioritize honesty? Is this a moment I need to prioritize speed or do I prioritize quality?” So, it's like you're always making these trade-offs and you as an individual need to be self-aware of what the right context is. And so, there's a high level of emotional intelligence here to read the room, to understand like what is the right judgment I need to make about how to operate myself and then also how I affect other people in the space, right? And that's like when you think about an executive, because their words carry so much weight, there's a level of emotional intelligence you really need to exercise to know “How should I show up today or in this hour of this meeting?”
Jayneil: You mentioned that word, ‘high level of emotional intelligence’, and that really blows me away because so far, some of the best design executives that I worked with, I want to say that their emotional intelligence is on a whole different level like compared to mine. I'll give you an example. This is my interaction with, you know, Andy Vitale, the design executive that I've had the pleasure working with. I ran into him in the office one time and then what happened was he was really on the way to another meeting and I wanted to take a photo with him, right? Fanboy moment, whatever, like “Oh you take a photo.” So, he's like “Oh my God! I got to run down to the meeting. Maybe some other time.” You know what happened next? The next day … and then I forgot about it, you know. I was like “Okay, cool.” He was busy and that's it. I did not read anything to it. It was like, you know, they went on and I had some amazing food. Next day, when I woke up, there was an emo in my inbox that was sent at 6 a.m. from Andy “Sorry, we couldn't take the photo together but definitely next time” like dude, this is just next level of emotional intelligence like I was … I had moved on from that. I was like “Okay, cool.” I asked for a photo and because he had to run down the meeting, we couldn't make it happen but he was empathetic like “Oh, you know what? Maybe Jay wanted to really have that photo.” So, to me, that was a moment where I experienced what high level of emotional intelligence looks like from a design executive. And it's got to be draining a little bit, right? Because you have to operate at a very high level, I guess.
Gordon: But if you think about it, those are the little moments where he’s building a sense of “I care about you. I see you. I feel you” and you're going to feel more loyal. And this has nothing to do with compensation, titles. It's making you feel seen. And I think this is such an important job of any leader, design or other, is how do you read people and understand what matters to them and act on that. And in this case, in a design organization of so many people, that's not going to be an easy job.
Jayneil: I felt so special.
Gordon: Right, you felt special. And these are the moments where I think you end up maybe producing even more interesting work because you feel safer.
Jayneil: Yes, like you want to go a little bit above and beyond like I felt this sense of connection and loyalty to him from something that is not design related at all.
Gordon: Correct. And so, when we come back to the earlier conversation, what does it mean to be a design executive? It's like it's so much more than just the creation of products and artifacts. It's now like a whole layer of orchestrating “How do I continue to manage an organization that is comprised of people and individuals who each have their own needs, wants, and motivations?” And so, when he did that for you as Jay, you're like “I felt seen. I felt special. And I feel a sense of belonging.” And so, again, emotional intelligence here is super important because you're now dealing in the art and science of people, not just creating products and services. You're affecting the people who will create products and services for the company but you need to … number one is your most important resource is your people, right? And so, if you don't do that part well, you're not going to create great products and services. I think about … one thing I actually really did enjoy just looking from afar at, you know, I think about some of the best designing … it’s like how do they foster a space of camaraderie in their organizations. And I see the sense of like chemistry and kinship between their teammates. And they talk at a level at a fidelity and speed that is so much more superior than other teams that are just a bit more transactional, a bit more just cut and dry and there's no like energy or vibe there. And to me, that's a differentiator of what separates good creative environments from not so good creative environments.
Jayneil: My mind is right now blowing on so many different levels because I'm getting all these rad insights as I'm talking to you. It's like we have the traditional, you know, design career playbook which is like you have to do these set of tasks or things and you prove them and you get promoted to the next level, hopefully. And it's very linear. And the more and more I'm talking to you, I'm getting the sense that that playbook is probably not applicable when you are trying to become a design executive.
Gordon: If you think about the sequencing of roles you can take at an organization, the first few, the junior level rules, are far more linear. They're based on “Can I do the job on time reliably and at a decent quality?” and even, you know, simple things like “Can I even take in feedback in a design review constructively without like shutting down because I got so defensive, right?” Those are simple things that really matter early in your career, you're building the basics of being a professional, but once you pass let's say the senior level designer role and you're considering like, you know, the next level or even to management, this is where emotional intelligence really plays a role beyond just “I'm a good professional. I can just do the job” but no, we need to not only do the job but be really excellent in exercising judgment and your ability to relate with others and foster an environment, build culture. And then further from that is like also the business acumen side. Do I understand the business model? Do I under understand what differentiates and makes this company successful? Where are the gaps and threats that I need to act on? Can I bring those insights to other stakeholders with honesty and directness that makes sense? And you can see how all those kinds of like base skills of just being reliable and of, you know, quality morph into higher orders of tasks that are more complex. And one word I really love is ‘adaptive’. Adaptive problems or systems are things that are constantly changing. And so, you're never really done. Once you finish it, there's already a new problem that arises from that problem because the system's always changing, the markets are always changing, the conditions are always changing. So, you need to kind of find what those principles are that help exercise and govern yourself in an adaptive world that's always changing. And so, you can see how this playbook shifts, right? Am I someone who can just do the job or am I someone who's built a model to which how I conduct myself in an ever-changing world and make decisions in an imperfect world? And that's like a sense of maturity that that can be really difficult to grasp because it's not obvious in a lot of career discussions but to me, this is what I call a chasm that one must cross. There's a couple chasms in any career framework in any organization and one of the biggest ones is going to be when I jump from just a senior designer to that next level and there's probably another chasm up there when you go from I'm a senior manager trying to become a director or I'm a director trying to become a VP or I'm a VP trying to become the chief design officer. There's a couple chasms that demand enormous change from you both internally and externally emotionally and also, you know, from a craft standpoint. So, change is kind of constant here, both as a designer and also just as a human being. And I think this is where it gets really exciting is like we start to think about not only professional development but personally, to me, it’s personal development and that plays a lot into you as a professional.
Jayneil: I'm kind of curious now like how do these design executives level up? One avenue that you mentioned is obviously like, you know, being part of Design Executive Council and joining the dinners and exchanging learnings and stuff but what are some of the themes you've noticed about them in interactions like how do they approach self-development?
Gordon: The key thing here is to view it as “No one else is responsible for my development other than myself,” not even your manager. And when you develop an ownership mindset, it changes the equation from “How can my manager help me level up? How can my manager help me identify things that I need to grow?” Rather it's changing the equation from “How can I help myself identify what I need to do to grow and level up?” And then I will go to my manager with prompts and targeted questions that I need answers to or insights to. It's changing from an approach of reliance to self-dependence. It's not saying don't work with others in your development but it's taking that number one thing is “I'm the owner” and you see this a lot play on an organization where people don't have an ownership mindset and they rely on others to help them grow. I was like “Well, I'm not responsible for your growth. That's your own journey. That's your career.” When you make that unlock, it will benefit you throughout your entire career.
Jayneil: This is the first time ever that I've seen such a nice analogy or similarity between a design exec role and being a founder because like in the startup space, in the founder world, you are accountable for your own success. You have to take ownership. And the way you're describing that, I'm finally seeing through a different lens that instead of just relying on the system and everything you're like “You know, how can I be this like founder of this group that I'm leading as a design executive?”
Gordon: if you come back to that word ‘ownership’, I think of an entrepreneur, a founder, a CEO, they are the only ones who can do it because they're responsible for it, right? And so, even now as a founder of the Design Executive Council, that's the shift I had to go through like in the first like … I was like waiting on my team for certain decisions but I was like “Wait, Gordon, you're the one who has to make this decision. This is your call.” And, for example, some of the things I have to learn right now are about tax, legal structures, and compliance and I'm like “Who's going to teach me this?” It's not design related but it is important for me to know this stuff so I know how to design what I need to design but I think similar to … just think about anything from a career standpoint is that the further you want to go in scope, responsibility, you need a higher degree of autonomy, ownership, self-accountability, all those attributes that enable you to be your own self-driving unit because you're now less dependent on others for your own success but it's not saying … you also still need to learn how to work with others in driving your success but you first need to clarify your own inner self and drive that yourself. You're in the seat, you're in the pilot seat, you're like keep that in your head like “I'm the pilot. This plane is not going to fly unless I choose to fly it and toggle how fast I want to go.” And if I'm sitting as a pilot and all my passengers are behind me, my team, and if I'm not making clear decisions, no one's moving. We're stalling. So, that's the difference, right? It's like am I just a passenger or maybe even I'm the attendant helping the passengers or am I actually the sole pilot who has to make the judgment calls of where we're going to go and how fast we're going to go, where we're going to land. It's the same with your career like sit in that pilot seat. Where do you want to go? So, I'm like “Jay, where do you want to go?” like you have to own that.
Jayneil: You know, now that you mentioned the pilot analogy I think, for me, personally, man, podcasting has been that taking charge of my own career because no longer am I waiting for some chance and traction of meeting with my dream designer or someone that can alter my mental model, I am proactively reaching out to these people building the relationships proactively rather than waiting for the right time, the right moment. So, 100% resonate with that mindset.
Gordon: I was just going to say am I waiting for food to come to my table or am I going out to hunt for it myself because I'm hungry? Don't wait. Go seize the opportunity. If you want something like … it's going to be real uncomfortable but you're going to have to make it happen.
Jayneil: You're surrounded by these kinds of people. There are self-starters, ambitious, all these design executives that you're having dinners with and you're hosting dinners and you're interacting with them. I'm curious to know how have those interactions impacted your own development and career growth?
Gordon: I can tell you the first few months of doing this, it was so uncomfortable because I'm sitting there with people I have respect so much and I look at them like “Wow! They're like in some ways these like icons of our industry.” And I really had to learn how to shake that off because I kept feeling a sense of like “Is this imposter syndrome? Is this anxiety? Is this fear?” but it's in those moments you realize this is going to be a growth moment because I'm feeling that. I'm feeling really uncomfortable. And so, in the first few months, I felt a little bit paralyzed. I actually stopped a lot of my social media activity because I was like “I don't know what to do about this information. I feel like I'm holding something really precious.” And I had to get to a point where I started unlocking myself so I can show up on these spaces again and realize that like I'm in this special position and I see this with a lot of humility and privilege that like “Wow! I have information, I think, I could really help other people.” And so, it's on me to go out and share it and not be afraid of doing that. And so, when you start to surround yourself with people who are more advanced than you, more mature than you, you will feel that discomfort I felt and that's a good thing. You should lean into that. Don't allow yourself to cower away from it because that's actually where the growth is going to happen. It's like the growing pains of anything. So, when I noticed that, that's kind of like I had to do whatever I needed to do to find the courage and confidence to go back out there and keep the work going.
Jayneil: I am so happy and glad that somebody as ambitious as you is leading the efforts for Design Executive Council. For all those design executives listening or future ones that are going to join, I think, on behalf of them, I can say that they'll be very grateful that somebody like you that's a go-getter is leading these initiatives.
Gordon: Thank you, Jay. Really appreciate that.
Jayneil: Just want to say thank you so much, Gordon, for coming to the show and sharing your wisdom on what it's like to really be a design executive and most importantly, what is the hard things about being in this role.
Gordon: I'm so thankful I could share this knowledge. I think I really have to be grateful to all those design executives, mentors, coaches I've had in this experience of building the Design Executive Council. Without them and their guidance, I would not be where I am. So, I'm calling this out to say thanks to all of them listening and for being that light for me. So, I hope we can build something pretty incredible in launching this Design Executive Council.
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