Balancing Pragmatism and Creativity in Design Leadership

Transcript

[This transcript is auto-generated and lightly edited. Please forgive any copy errors.]

Jesse: I’m Jesse James Garrett,

Peter: And I’m Peter Merholz.

Both: And we’re finding our way,

Peter: Navigating the opportunities

Jesse: and challenges

Peter: of design and design leadership,

Jesse: On today’s show, Cynthia Savard Saucier, co-author of the book Tragic Design and VP of UX for the Canadian e-commerce giant Shopify, joins us to talk about what’s worth fighting for and what’s not, sharpening the business acumen of her teams, and the strategic value of kindness.

Peter: Hi, Cynthia. Thank you so much for joining us.

Cynthia: Hi. Thank you for having me.

Peter: So, if you could share with us what your role is, and I’m curious, because I know you’ve been there for a little while, how your role has evolved.

Cynthia: Oh, yeah. One answer is faster than the second. So my role is four letters: VP UX. I like it. It’s very short and easy to reply. I’m vice president of user experience at Shopify. At Shopify, we use UX as a overarching word for content design, research, and design as well. So I lead all of those disciplines.

In the past, I’ve had other roles at Shopify. So I started there almost nine years ago now when it was a much smaller company. I started as a designer, IC on the team. I was leading a smaller team at an agency before that, but I chose to join a tech company as an IC, and then I grew from designing the thing to leading one person and then the Montreal team, and then eventually becoming a director and then eventually leading the whole discipline at Shopify.

And then recently I just made a bit of a horizontal shift where I chose to focus on the product. So now I am VP of UX for core. So I directly manage a team of around 200 people-ish in UX for core. Core is the core offering of Shopify. So it’s mainly the admin experience for our merchants. So that’s how I went from IC to VP in nine easy steps.

Peter: Thinking about the organization, I know Shopify has gone from having a centralized UX org to a federated UX org. Did it then go back to centralized and now it’s federated again?

Cynthia: It’s a bit of both, actually.

So we had a chief design officer that was the co-founder of Shopify. So he had been there from the beginning. And when I joined Shopify, I was actually reporting into Daniel, who was the co-founder. However, as the team grew, we then went into product lines. So the whole organization got split into like a bunch of, I think, seven groups.

After a while, we just reached the edges. Like we were, we were, like the seams were cracking from these groups or organizations, and then we reorg-ed the company into two larger groups. So there is core and merchant services. And now all of UX reports into UX into core and all of UX reports into UX into merchant services.

So it is somewhat functionally reporting. All the way up to me and Andrea Manini, who is the VP of UX in merchant services. But under that, if you are a UX or you report into a UX leader all the way to me basically. So it’s federated and functional at same time.

Peter: Andrea doesn’t report to you. She has a different…

Cynthia: Exactly. So we both report into the leaders of these groups, basically. They both happen to be from product, but it’s not that UX reports into product. It’s that we happen to report into the person that also leads product.

Peter: And given that you have these two UX teams, is there anything that’s holding the center of user experience at Shopify, or is Andrea able to kind of “do whatever you want,” and maybe it starts to diverge, or how do you make sure this stays aligned across your orgs?

Jesse: Well, even beyond that, I want to ask, is it actually all that necessary for the two teams to be aligned or are you really separate worlds entirely?

Cynthia: I mean, we are separated in many ways. However, we are touching very common user experiences. So for example, the core, the admin of the product. While I own the scope of the majority of it, there are still a lot of services that merchant services, the other organization, is responsible for bringing to life, and this does get introduced into core.

So we do need to be very tightly aligned, but ideally loosely coupled. And this is why we have different leadership structures. There’s many ways we create, like, a centralized organization, like a centralized culture, centralized discipline, hiring practices.

Leading The Discipline, Maintaining Coherence

Cynthia: So this is through discipline work. So that was a role I used to have, which was leading the discipline of UX. Leading the discipline doesn’t mean everyone reports into you. It’s more like all of these horizontal tasks. So you can think of design, or UX ops, recruitment, hiring the big goals of the organization as well.

What’s the makeup of the discipline? How many people? How should it grow? So now this is something that Andrea does. The discipline is horizontal, so we look at it across all the teams. However, the ownership of the user experience and, like, really how that transpires into the product, this is reporting into both of us basically.

And the way we achieve unity or cohesiveness to a certain extent, well, first of all, we have a design system. So we have Polaris, who’s a open source design system. It’s, it’s a really good design system, actually.

Peter: It’s one of the OG design systems. It’s been around forever.

Cynthia: It’s one of the OG ones, yes, yes. But it’s still very well maintained. We’re at v12, that was just released, not too long ago.

So the design system is one of the way that we achieve like some sort of alignment. But overall we have design principles, we have design values, and really we work with each other as much as possible. Like this whole idea of like providing a lot of feedback, getting really involved, not being afraid of going into details as well, is definitely one of the tools that we utilize to make sure the experience just works together.

The whole principle of, like, not shipping the org chart is very important to us, and our merchants are using our admin without any understanding that the organization might be organized a certain way or not. So it’s very important for us not to let that bleed through.

Jesse: You know, when I hear stories about these kind of horizontal leadership models where, and correct me if I’ve got this wrong, but, a case where people are driving outcomes across teams that don’t report to them…

Cynthia: mm hmm.

Jesse: …and they are, attempting to influence the organization on a broader scale than the reporting structure itself actually provides or allows. And what I hear from folks in a lot of these cases is that this is a recipe for frustration, disappointment, and disempowerment. And so I wonder. If it’s working for you guys, what do you think is making it work here?

Cynthia: Yeah I mean it requires a few things but first and foremost like it’s a set of tradeoffs. Like there’s no magic answers. You could have everyone report into a single person, and that would be good for certain things but really bad for other things, such as the decoupling of decision making, or it is impossible for any one person to have context on every single piece of the organization of the product.

Really, the product is really complex, but also, like, I fundamentally believe that different organization makes decisions differently. But that’s a feature, not a bug. We want the growth team to be a little bit more gutsy. We want the growth team to be more aggressive with the features that they’re willing to test out.

And at the same time, we want and we need the core team to be a little bit more resistant to creating a lot of quick iteration. We want it to be more foundational. And that is also part of how we achieve good results. So to me, like this is a trade off that we are making, but one that works for us.

I have been in this situation before where I had, like, to influence without the authority, which is what you’re referring to. And yes, there are pieces that can be frustrating, but like, I think I’m an eternal optimistic. Like, I, I can recognize that something can be frustrating without being frustrated about it.

And this is what I try to tell people as well, that like, hey, the disempowerment that someone might feel is actually just a misreading of the priorities, because in the end, our CEO actually really, really believes in the importance of UX as a discipline. Like I don’t need to sit down in a room with Tobi and explain like, “Oh no, UX is important, Tobi, please remember that it needs to exist.” We don’t have to fight for that. It’s a given. It’s actually like our CEO has to remind us sometimes like, “Hey, fight for yourself,” because we don’t have to do it naturally. And because Shopify doesn’t have to fight for UX most leaders that have grown at Shopify were not selected because of their ability to fight for UX, if that makes sense.

So. I mean, we do have the classical executive sponsorship, so this is not something that at the discipline level you need to convince up and down. It’s just about convincing down and bringing people together. And then when you are that person that is trying to create that cohesive experience or culture, of course, like some people are motivated to ship their thing and you might get in the way of doing that.

So there’s a lot of negotiation, there’s a lot of conversation that needs to happen, relationship building as well, like only through trust can you achieve anything really when you don’t have authority. But I operate from a place of, you know, I have a trust bank and then sometimes I need to make withdrawals, and sometimes I put back trust in the bank, and this is how I achieve anything basically.

Accountability for UX

Peter: I’m curious how you are held accountable as the head of UX for core products. Like does your boss have a set of things that are expected of you, to deliver outcomes, impact, anything like that, that is somehow specific to UX separate from the work of the product team.

Cynthia: Yes, the answer is absolutely yes. My boss, my manager, Glenn, basically leads core, will absolutely come to me if an experience is broken, if something is suboptimal, if something is not as good as it should be, if there is a visual bug, but sometimes other types of bugs as well.

So I think it’s hard to really define precisely what my role is. Like, we always say, like, aim, achieve and assemble is the framework we use, but I don’t think it does a great job of explaining everything that I’m expected to do. But mainly, I could not do anything about the discipline. As long as I have the right impact on the quality of the user experience, I’m doing my job at Shopify. Like we are very product-impact-driven and, like, what that means for me is ensuring that our product gets better every day.

If I do this, I do my job. Everything else are tools that I set for myself to achieve that role better. So my boss doesn’t care about what culture I’m creating on the team. My boss does not care about what tool I’m putting in place, or systems or processes or any of that, as long as I have the right incentive structures in place for my team so that we achieve great UX.

That’s all that he cares about, but he certainly cares about it and will hold me accountable for the quality of the UX, of anything shipping under my scope and sometimes outside of my scope as well, as he rightfully should. So if something ships from a different team that happens to touch a surface area that I own, and I didn’t pay close enough attention, I wasn’t curious enough, I didn’t get involved enough, that is on me, because in the end, our merchant don’t care. If I’m the boss or not, like they are using a page and if it doesn’t work appropriately, I don’t get to say it’s not my fault, it’s this other team. That’s something that we really don’t ever want to say at Shopify.

The Trust Bank

Jesse: So this shift into taking more responsibility for the outcomes was a natural result of your moving from a position of influence without authority to a position of authority, and you mentioned that when you were trying to wield that influence without authority, it all relied on what you described as the trust bank.

And I love that that metaphor for it. You know, a lot of leaders, as they are moving into these executive levels for the first time, they might not have a trust bank to work with yet. And I’m curious about, now that you’re in this role where you do have the authority, how does the trust bank still play into how you do your job, and how can someone who’s stepping into that role go about building that trust bank for themselves?

Cynthia: I really like that question, because it is unfair for me to assume that everyone has been at a company for 10 years. And I have, I’ve grown and I’ve been in every position, so I have a really good idea of, like, the context and the people and the organization, and it’s not true that everyone comes in with that, so that’s actually a great question.

Trust plays a role that people misunderstand sometimes. They believe that the exchange currency between an employee and a manager is money. But really, that’s not the case. Money is a currency between the company, the employer, and the employee. A manager, an employee, the only currency is trust.

And if I want my team to achieve anything, I cannot just use authority because they can choose to not listen to me and that’s it. It’s about trust. It’s trusting that I will say the thing and if they achieve the thing that I have said, they will be properly rewarded for that thing. It’s believing that the thing I say is closer to the end result than if I didn’t say that thing.

It’s trusting that I understand enough about the craft that I’m not going to send them in a crazy goose chase, trying to find solutions that don’t exist. So that’s a trust that I need to build even with people that are reporting to me. Trust is multiple things and you don’t just have it by magic. It’s three things.

So, it’s interpersonal trust, it’s disposable trust, and institutional trust. So disposable trust is, as a person, how likely am I to trust? This can be influenced by like, have I been scammed in the past? Were my parents trustworthy? So this is very individual. This is hard to influence.

And you have to recognize that you are interacting with people. They have their own ability to trust, and this is something that is hard to navigate. However, if you know that you’re with someone that is less likely to trust, you just need to build a lot more trusting moment, because trust is built.

In order to build trust, you go through interpersonal trust. And that is basically, like, how credible are you? How knowledgeable are you? How likely are you to do the thing that you said you were gonna do? Do you have a lot of experience achieving the thing you said you were going to do? So, if I need to do something with someone that I know is not trustworthy, I will say a lot of small steps, like I will say a thing and then do the thing.

And then I will request for them to do the same thing. And this builds mutual trust together, until we are in that stage of like, they know they can trust me. I know we have to create smaller trust steps, if that makes sense, instead of just pointing at the mountain over there.

There’s also institutional trust, and that is really hard, because the institution is really anything that is supporting the trust relationship. So that can be the organization, the company, but it can also be like the banking system, or technology, or the stock exchange, you know? It’s all of these institutions that are underlying the trust relationship. And again, this is really hard to build on that trust. But if the person doesn’t trust the institution, if I have an employee that doesn’t trust Shopify, there’s very little that I can do as a manager to change their mind.

I can try to explain better certain strategies. I can try to involve them as much as I can so that they understand where things come from. But aside from that, that’s the best I can do. If they don’t trust it, there’s very little I can do. If they work for a tech company and they’re like, actually tech is going to crash, oh, I can instill a certain amount of optimism, but in the end, like that’s going to be very difficult.

So I would say for someone that just joins an organization, they have to look at like the interpersonal trust level and do as much as they can in that layer. So showing that you’re credible, showing your experience, relying on that experience, and then setting a lot of small steps saying you’re going to do a thing and then doing that thing, whether that’s this afternoon, I will send you an update, send that update and like create a lot of opportunities for trust building.

Peter: It’s clear you’re leaning quite heavily into the concept of trust as part of your leadership. And I’m, I have a few questions around it. This framework of, was it disposable trust? Was that the first one? Did I hear that…

Cynthia: DIsposable trust, just [like] disposable income. You have disposable trust as well.

Peter: Okay, so disposable trust, interpersonal trust, institutional trust. Is that a framework you developed or is that something you learned somewhere?

How did you hit upon those three trusts?

Cynthia: This is a real framework, however I’m explaining it and I’ve reused it in leadership, in the concept of leadership for many years at this point. So I cannot go back to the actual study that actually points, but there’s a real trust model. It’s also very, very Important in e-commerce and like, this is my business, but like, we’re building a trust relationship between, like, a buyer and a merchant.

And basically buying online is a trust action. I expect that in exchange for, like, fake money, literally, like I’m sending a number and that’s gonna be money, hopefully everyone understands that money, that I’m going to get an object in exchange that is worth the same amount of money.

And then merchant is like, I’m hoping that the numbers that are sent and written in a form are reliable and I’m going to get money in exchange of this thing and I’m going to send that back. So it’s a trust relationship that we both agree the value of the exchange is the same. And lean in a lot on the trust model there, because in the end, like our goal is to make sure merchants can build a lot of trust with their buyers. So everything we do there, like helping them have better product picture is about building trust. Helping them have a professional website is about building trust. Helping them create better content is about building trust. It’s all about it, basically.

Peter: And then, so you, drew from and then have developed this framework for trust in your practice. I’m wondering if you have tools to help you understand how to manage your trust relationships with others, like documents where you’re writing down, like, trust, trust quotients and stuff…

Cynthia: 74%.

Peter: …or, or if this is, or if you used to have tools and now it’s something that’s just like a muscle memory that you’ve developed and you don’t need to be as intentional, or do you actually have, I’m thinking about it on behalf of the other leaders who are listening to this, like, like, is this something that, like, there’s worksheets to help kind of scaffold your way through this, or is this just something that it’s just kind of how you engage with these things kind of rattling around.

Cynthia: So it’s definitely not, I don’t have like a worksheet with everyone’s name on it and I’m like, oh, this person trusts me or does not trust me and therefore I will like tune in to like how long or how often I send in updates or like whatever. I don’t have that. I do like at one point intuit it from my interactions with people.

However, I do find myself using it and even explicitly when someone starts reporting into me and like, hey, I’m your lead, I’m really hoping we get to build a horizontal relationship, not a vertical one, where like, we are both as valuable, we just happen to have different responsibilities, but in order for that to happen, we have to recognize that I will know things sometimes that I don’t get to tell you, and trust me that I will tell you the things whenever I can, and if I can’t, it’s because I have a good reason for it, I’m not like trying to play with you or anything. I’m not playing like a power move or anything.

So I will use and say, like, trust me that this will happen. And whenever it happens, I reinforce it. Like, hey, see what just happened. We had to announce this thing. You see, I could not tell you that information. I wish I could have, but I could not because of that reason, and that reason, and that reason. If it would have been legal for me to share that information, I would have. Or if it would not have created an external risk, I would have shared it with you. So I also share, like, very explicitly the reasons that have led me to maybe make a small break in trust at that moment, or use it to explain my rationale and hopefully increase trust with that person.

So I definitely am very, very explicit about it. But I don’t really have a worksheet. I will, though, like, create a lot of, like, systems to support it. So I die by my calendar. Like my calendar is like literally my life, but I’m very intentional about designing it in a way that supports it.

So if I say like we’ll have a one on one every other week and I never cancel it unless you want to cancel it. Well, I do that and I make sure my calendar is up to date and like it has designed that time in so I’m very very intentional about how I use that time and making time for trust building moment is super important for me.

So trust building moments are, yes, one on ones, but also like separating one on one and product review is very important to me because one on ones will talk about you and me. Product reviews will talk about product, and then you get to invite whoever you want. And you get, as a leader reporting to me, to use that time to build trust with your own team, that you will bring them and create visibility with me. So, I don’t have like a worksheet or anything, but I certainly introduce processes to make sure I stand by the things that I say.

Peter: You’re very intentional in your practice, even if you’re not, writing it all down in a spreadsheet somewhere.

Cynthia: I don’t look like it. I’m very casual, but I’m also very intentional. Yeah.

Jesse: So I love this concept of institutional trust, and I can totally see how that plays out among your design team in terms of making sure that they feel like they trust where the business is going. They trust, you know, all of it. I noticed that there is also an exercise in institutional trust building that design leaders often have to take on, which is not team facing, but which is rather about building institutional trust in design itself across the other functions of the organization and getting people to believe in the power of design, the value proposition of design.

What has your experience been building institutional trust in design as a function over the course of your journey?

The “Seat at the Table”

Cynthia: I’m very I would say lucky because I recognize that not all organizations start from a place of like caring about UX, and, like, our organization very much cares about it, as I shared before, so I recognize that this is not everyone’s experience. However, I always say that don’t beg for a seat at the table and like I always do like the big air quotes like “seat at the table.”

I, I don’t love talking about seat at the table because really like the only thing that I have seen working is merit. As in, like, if you want to be invited, you will be if people believe that you’re valuable to the organization. And if you are not valuable to the organization, you will be dropped out of the invite, even by mistake sometimes, and then no one will notice that you’ve been missing.

So, I’ve found that providing value to the organization and placing the organization first is the best way to come from a place of strength. So whenever I am sitting at the metaphorical table, I’m not representing design like, you know, the UN each representatives represents their country.

I’m not, I’m sitting at the table trying to achieve the best outcome for Shopify. And sometimes it’s, it’s not in UX’s best interest, most of the time it is, because I believe that, like, the incentives and what UX is trying to achieve is 100 percent aligned with the best interests of both the users and the organization.

But sometimes there is, well, we need to defund certain things, or we need to share our resources, or we might need to kill certain initiatives. Might not always be the discipline’s favorite thing to say, but you can’t just come in and fight for UX and think that nothing else matter, and it’s just like, Oh, it’s UX, UX, UX. And like, let’s fund it more, more, more, more, more.

Like it’s an organization. I’m working for a company and if I wanted to work for a nonprofit, I could, like, I’m choosing right now to work for a company whose mission I care about. I care about deeply, but I also recognize that the vehicle of that organization is a company and therefore, like, making profit.

So as long as I’m at peace with this, I know that the vast majority of the time it is really well aligned. But whenever I’m sitting at that table, I put my Shopify hat. I don’t put my discipline hat. Now in one on one conversations, that’s different. When I’m meeting with the person that leads engineering, for example, well, I do need to explain certain point of views to make sure that disciplines that are more numerous than my own don’t simply forget or like in French, we say “far from the eyes, far from the heart.”

So when you don’t see something, you stop loving the thing. My role is to to prevent that from happening and to advocate for the value of it whenever the value is real. It’s not to create fake value around something and I’ve seen and heard a lot of discipline leader that were fighting for their discipline at any cost. And I just don’t believe in that approach. I just believe, like, provide value to the organization, understand the business in which you are, and then you’ll be invited at the table.

Jesse: I think that a lot of these design leaders who feel the need to fight for UX all the time, if you ask them why they are doing that, they would say it’s because the organization is leaving unrealized value on the table, that an evolution of their design processes, just deploying the people that they already have in different ways, can help them realize that value.

And they see it as their role as design leaders to advocate for that unrealized value, to try to grow the value that the design team is delivering. And I wonder, you know, where do you draw that line? Where is it worth it to fight for the thing that the executives don’t see the value of yet?

Cynthia: There’s legitimate cases of fighting and like, I tried to pick my battles. Like, I stand firmly that no dark pattern will ever see the light of day for as long as I work at Shopify, whether that dark pattern would come from my team or from another team. This is a battle that I’m willing to fight.

I will pick that fight every single time. And thankfully it’s not a fight I have to fight very often, so I’m pretty glad.

Peter: [patterns] gets right at the heart of trust that like what you were talking [before].

Cynthia: It does, it does. And it only takes a user being scammed once for them to never, ever use your platform again. When we’re talking about e-commerce, if one merchant scams a customer, that customer will stop buying, not from that merchant, from all merchants. That sort of feels the same. Like this is unrealized value, literal unrealized value.

Like lifetime customer value is way more interesting when you look at it across all merchants than just like between one merchant and one customer. But that’s an aparté.

Most fights aren’t worth it

Cynthia: So there’s definitely some fights that are worth fighting for. I just I guess my criticism of some design leaders is that not every fight is worth fighting for. And we shouldn’t always show up as like, “Oh, poor us. Again, engineering didn’t understand that we really wanted to do wireframes.” And I’m like, no, they don’t understand. And that’s cool. We don’t understand their frameworks. And like, they’re not crying to the CEO about it. Like, they’re doing their thing not caring about us.

So, like, I often refer to the little sister syndrome, family of four, I’m the youngest kid and I’ve always had like that “I wish I were 16 so I could drive.” “I wish I would be 18 so I could drink,” you know I always had like that little sister, I see what the other wants.

The reality is like, you can complain, but you’re not going to get older faster, you know, like there’s nothing you can do about it. The UX team is never going to be more numerous than the engineering team So let’s stop that fight, you know, there’s always going to be a ratio, well, whether applied or not. But there’s always going to be more engineers than UXers.

It’s not unfair; I actually don’t want to work for an organization that has more UXers than engineers. We would never get anything done. Like, nothing would ever get… So once you recognize why certain decisions are made, then those fights, drop those fights and pick the one that are actually valuable. And again, you can only win a fight if the other person trusts you.

It comes back to this, but like, if you show up as an executive, you show up at putting the company first, not your discipline first. And when you’re approaching it from that way, the fights that you’re bringing to the table are by definition fights that are benefiting the organization, not just your discipline.

Peter: How do you help your team, the 200 people that are in your organization, how do you help them understand what you just said, right, because they’re looking to you as the head of UX, so you are representing UX. They’re looking to you to provide inspiration and possibly creative direction, but you’re like, actually my job is to be an executive first, a UX leader second.

How have you helped them understand the nature of your job?

Modeling leadership

Cynthia: I’m sure some will actually listen to this podcast and be like, hmm. I would say, I try to tell people and explain how this is benefiting them in the end because the reality is, like, I get a lot of leeway from the whole executive team because they know that I’m not like being ridiculous about my spends, for example, that I’m being very strict about how I do performance management, for example.

They know that in advance, so I don’t get shit for it ever, you know, so I tried to represent the importance of that to the team. I’ve also been very careful about, again, representing UX as something that drives value to the organization, but not always measurable value.

And this is something we don’t need to argue about. We don’t need to measure the value of making a design change. Like, we’re good. This only happens when people believe that you’re utilizing resources well.

Else, they’ll start asking you like, okay, well you need to A/B test and prove me the value of every change you make. ‘Cause I don’t know if you’re using your resources well, and you have a pretty big budget. So if you want to maintain it, like show me impact, product impact. If instead I show up saying like, Hey, I’m going to be fairly conservative about how I use my resources, but trust me that I do it in the best way possible, that will drive as much value possible to the organization, then I get to make the call.

If, hey, just a design overhaul might be worth it, we just won’t be able to measure it. Actually, we won’t measure it at all. We’re not even going to be able to do it. Just trust us that it’s better and it’s better for the experience.

And it works, you know, we get to do those all the time and it’s great. So to people on my team, I tried to explain them that by having a seat at the table, which means acting as an executive, it creates a lot of leeway, creates a lot of flexibility and gives a lot of freedom to the team to really achieve their goals.

But also I tried to be very, very transparent about these decisions as much as I can with people on my team. And of course, like it requires a certain amount of seniority to understand certain decisions.

But I discuss a lot of financial literacy, like, Hey, we’re a public company, our numbers are out there. You should understand those numbers so that you understand the context in which certain decisions are made. And by sitting those decisions into reality, it really helps explaining certain decisions that might be harder to swallow sometimes.

The intersection of business and design

Peter: Your participation on this show was suggested by Andy Healy, someone that you used to work with. And he said in an email to Jesse and I, Cynthia has been a driving force at Shopify, encouraging all designers to think about the intersection of business and design, which I’m bringing it up because I felt like you were, you were getting…

Cynthia: I’m glad he believes that!

Peter: You were, you were, you were getting there. And so I’m wondering, when he’s mentioning this intersection of business and design, is that something you address explicitly? Do you have ways of talking about how design and business integrate, interact, intersect, whatever it is? And what are those ways?

Cynthia: Funnily enough, no. Like, I rarely talk about the importance of UX for the business. Surprisingly. So it’s rare that I come back and say like, Oh, because we’ve made this uplift, like it has led to 33 percent more conversion on that page. However, when we have that data, sure. That’s a very fun thing to celebrate, to say like, Hey, really just this design uplift has led to higher conversion. That’s amazing.

And I love those stories, but honestly, it’s pretty rare that this is how I approach it. I’ve done a few things directly to the whole team. When I was leading the discipline, I chose two big rocks one year. The big rocks are things we want to work on as an organization. And I was like, the first thing is everyone needs to have a test store. So everyone needs to have a store that is actually active, that you have a lot of things happening on. And the second thing is you have to improve either your technical proficiency, or financial literacy.

And these are the only two things that I will talk about this year, and I will measure. We had like a survey bot sent to people and we were asking them like, what have you done this week to learn about something new? And we were looking at the results there. We gave some talks internally, but also we have a lot of very, very smart people at Shopify that can explain financial results in the most descriptive and interesting way.

They’re basically like MBAs in 12-minute videos. I definitely ask people to watch those. I discuss those. I try to make as much noise as possible around it, because by definition, if you chose design, you probably weren’t going to go in business. There’s a little bit of a self-selection process that is happening there.

And I’m like, hey, do as best as you can in the things that you’ve selected by definition, the default will be that you’ll continue doing this thing. You chose to do this as a career. You’re interested by it. You’re surrounded by people that will propulse you in that direction. So I kind of need to break that default a bit and say technical and business literacy is very important in the context that you are operating at.

Peter: What proportion chose technical and what proportion chose business?

Cynthia: Actually, the vast majority chose technical.

Peter: That does not surprise me at all.

Cynthia: But I’m not disappointed by that. ‘Cause I think it’s also like, If someone has another X thread of like, should designer learn to code? Like I might break down, like, I’m like, just should designer learn period? The answer is yes. Just learn. Learn about the other things. Why would we argue against this learning to code doesn’t make us any less important, valuable, necessary. No one says you should learn to code instead of being a good designer. That’s a little sister argument in my opinion that we should not learn to code.

Learning is good. If you work for a tech company, learn about tech. That’s a good thing. Should designer learn about commerce if they work at Shopify? Yes, yes, they should. They should be very interested in commerce if they work at Shopify, that’s just basic in my opinion.

And we want to hire people that have a growth mindset that are interested by learning that aren’t learned helplessness of like, oh, but I don’t know, so I won’t do it. It seems hard. That’s not what we want. That’s not the people we want to attract. So, yeah, I have no problem with people choosing to learn about our tech stack more.

Jesse: I want to back up to something that you said earlier. You said that part of what you do is Recognizing that a situation can be frustrating without personally being frustrated.

Cynthia: Frustrated, yeah.

Jesse: And this touches on the notion of emotional resilience for leaders and your ability to ride it out when things get tough.

And so I wonder, you know, how do you acknowledge the frustrating nature of the situation without getting frustrated yourself, and how do you maintain an even keel through all of this?

Cynthia: I’m going to quote a, well, not quote, refer to a psychologist, I believe. I cannot remember their name. I just remember reading what they shared in at one point. And they were specifically talking to women in leadership positions. And I’m not, I will rarely talk about being a women in leadership or women in tech, because the reality is, like, UX has a very high proportion of women, like, we’re not in a situation where like there’s not enough women in UX. Like, it’s great. We have a lot of women, something that is amazing, but it’s not really like a fight that I feel, like, well-equipped to do because like more than half the team are made of women.

So I’m not in the minority here. However, like in leadership positions, I’m very aware that there are certain traits that tends to be punished more when they come from women as to when they come from men. And this is having an emotional reaction to a situation

When a man has an emotional situation, they are seen as vulnerable. Or the situation is bad enough that their emotion is warranted. When a woman has an emotional reaction, and i’m saying in general obviously, but these are facts, but it’s in general, when a woman has an emotional reaction to a situation, it is her that is the problem. Whether the situation warrants it or not, is not part of the message and the judgment.

So that person said, instead of acting angry, say you are angry. Instead of acting out and, like, screaming, say, Hmm, this is very frustrating. And using the words will be enough for people to understand, because you don’t want to hide your emotion either. Like, that’s not the point of the thing. It’s not like pretend you have no emotion. I don’t think that’s a good way or human way of operating. I’m all for, like, emotions being shared, but saying the emotion is just as satisfying as it is to actually act the way that you feel, and is enough to actually operate some change and not get the punishment that comes with the emotion.

When I read that, I thought it was actually super powerful and it was a good way for helping me navigate situations that can be very stressful, that can be very frustrating. But when it comes to, like, recognizing things can be frustrating without being frustrated about it, I think this is me, like, growing up.

I’m fairly young still. And I know that I have things to learn. I’m still on this journey of, you know, growing up and being more mature and not having such a hot reaction to things that I think are not ideal, because I am very passionate and I care very, very much about how things are done. And like, if the things are not done in the most optimal way, it gets in the way. It’s frustrating to me. Like, these things really matter to me, so this is something that has just been a very helpful tool. Recognizing, like, hey, this is super frustrating, but am I actually frustrated about it? Like, will I think about that overnight, or is this just not ideal? Is it just like messing with my idea of how the thing should be working, or is it really frustrating and will have an emotional impact on me?

It’s been very empowering.

Jesse: Well that sounds wonderful and almost like a Buddhist monk or something in terms of your non-attachment that you’re practicing here. Yeah, but I wonder, you know, aren’t there days when you bring it home, right? Aren’t there sleepless nights for you, or are you really able to just let it all go?

Cynthia: I mean, my husband works at Shopify, so like, bringing it home literally means like every day. I still get frustrated about things. I get angry at things, but I try to choose which one I really get angry about. Like, I get angry about the work being not good, the product not working well, or, like, when for organizational reasons, we got into a position that is bad or that is frustrating to the users.

Like, these are the things that are frustrating to me. I get frustrated when there’s bad intent, when someone is just not operating from a place of like, just good intent, or like ego these are actually frustrating to me. I’ll get angry at that, but again, choosing what I get angry about makes my anger spur a lot more powerful…

Jesse: mmmm…

Cynthia: Anyone that is using anger is using it as a tool, whether you realize it or not, you’re trying to convey a certain message by reacting with anger when like, in the work environment, let me be very clear, I’m talking about work here, like, not in your personal emotional relationship, but at work, if you’re choosing anger, it’s that you are trying to convey a message. That the thing the person is saying is not the right one, you believe it’s the wrong one, or like, whatever. So choosing anger as a way to convey a message is actually very powerful when you’re not always angry. When you’re always angry, then people dismiss your anger for being just like, you’re just someone that reacts a lot.

So yeah, I’ve tried to turn it more into like a leadership tool and a communication tool, like designing the communication basically,

Jesse: Mm hmm.

Pragmatism

Peter: One thing I’m picking up on is a strongly pragmatic orientation.

Cynthia: Yeah. I tend to be that.

Peter: I’m wondering if, if pragmatism is just kind of who you are and how you approach things, or if pragmatism is something you’ve had to learn on your journey.

Cynthia: I mean, surprisingly, I was a creative kid, you know, like I, I was in arts and stuff like that, but I think I’ve always been extremely pragmatic, and this is something that serves me well in the industry because there’s also a lot of less pragmatic types that become very creative and very good at what they do and they’re super talented, and their lack of pragmatism creates a lot of creativity as well, and I value that immensely, I really really value that piece. I love people that are extremely ambitious, but also like delusional about their ambition because I tend to be more pragmatic and risk averse, yet I have great ambitions.

I think that design as a whole is made of a wide range of personalities. A lot of people are more creative types, and leading with pragmatism actually contains people in a certain way. My hope is that I don’t restrain people, I just contain so that they can be very free inside of that container. But I mean, I’m not going to hide it.

I’m a very pragmatic person, but again, I’m very fun. I insist.

Jesse: Well, I wonder, fun notwithstanding, I wonder what the role of idealism is as you see it in the midst of all of this pragmatism, because I think that for a lot of design leaders, what you’re saying is breaking their hearts right now, because they see themselves as champions for an ideal, for a higher standard of service to humans and of creative practice and of all of these things that they are fighting, fighting, fighting to try to bring that ideal to life into reality for them.

If you’re not doing that, where does the idealism come into play in how you do your job?

Cynthia: My pragmatism and realism is that I am making the world a better place through design, that I’m using my design skills to improve the human race. Really fundamentally believe that I literally wrote a book about it. This is how much I care about it.

I fundamentally believe that creativity is a business tool. So I just happen to have a pragmatic view of idealism, if that makes sense. I happen to be very, very aligned with the values that comes from the design industry, that comes from helping the human, that comes from the fluffy stuff, like the fluffy things that people, like, struggle talking about, because it’s just about being nice.

I just see the value of being nice. I very much see it. And this is why I put it into frameworks, because this allows me to use that tool without falling into this place of being unable to discuss the other things as well, and making enough room for the other things that I need to have in my role, while fostering and caring and being present and wanting people to be creative and to do funky and fun and different things and fostering it. So my pragmatism is actually tied to the fact that amazing design is good and is actually helping humans. And that I always say, like, I strive to be kind, not nice. And again, that comes from a place of pragmatism, because I see being nice as getting in a way of achieving great things. I see being kind as a way to achieve everything.

Jesse: Mm hmm.

Peter: I want to continue this. So I am, I’m a pragmatist as well. And the risk of pragmatism as a leader is…

Cynthia: mm-hmm

Peter: …accommodation, right? There’s some dominant way of behaving that, practicing your realpolitik, you are going to accommodate to whatever that dominant way of behaving is. And then you’re essentially acceding to it, as opposed to, we were talking about fighting, maybe fighting isn’t the right word, but advocating for what you know to be the potential.

And so I’m curious, what your vision is of the potential for change, right? Most design leaders have some vision of the change they want to realize. And I’m curious how you think about that, how you approach that, ’cause you’re probably not satisfied with things at Shopify; however good they are, they could be better.

So what is, what is it you’re trying to drive people toward?

Cynthia: Yeah, I think, like, I’m not a peacemaker. So, my role is not to accommodate everyone, to make progress. I– We’re analyzing very deeply everything right now.

Jesse: Welcome to the show.

Cynthia: Yeah, I know. That’s great. But my role is not to accommodate, and my role is to definitely fight the right fights. I am very thankful for the leadership team that I have and my boss as well, where if I go to my boss, I’m like, Hey, this doesn’t work and requires more work or requires more resources. I’m blocking this. I might get pushed back, we might have a discussion, we might have disagreement about it, but in general, there’s huge trust that if I say like, hey, this is bad enough that it needs to be unshipped, or it needs to be delayed before we ship it, or even if it increases conversion, I believe it should be pulled down, or like, hey, I know the tests were positive, but I believe it has second order effects that might be bad. All of these things are totally respected, and appropriate.

And this is my role to have those conversations. It is my role to make sure that UX is not defunded because I believe that it has to be right-sized to achieve its goal. So it’s not about accommodation. It’s not about just peacemaking and being always the one that takes the hit just so that no one gets mad.

My vision for UX requires tension. So it needs engineering, UX, and product to have like the right amount of tension. And if UX is the one that keeps folding, the two other pieces will fall over it.

Like I want to hold that tension. And I think I do very seriously, but I don’t want to pull too hard on that string so that it breaks that filament at all. Does that make sense?

Peter: It does. I’m, I’m wondering what, if any, agenda you have, like, what is Cynthia trying to advance within this context?

Cynthia: I ultimately just really care about the quality of the design in the product. So everything that gets in the way of that, I will fight for. I care very much about someone using our product and feeling empowerment through it. I care that our employees see the value that they create in the world. And I always say, you could be working at any companies you want in tech, at a certain level, like you could go to a different company. I personally, like, chose to become a designer because I wanted to use my brain, my creativity, and what I’m able to do, like my ability to shape things in order to improve the life of the person that I’m designing for.

And as long as I work for a company who’s a hundred percent aligned with that, I’m good to go. Designing is about, like, changing a person’s behavior. You’re trying to make them do something. As long as I’m using my brain to make them do something that benefits them and someone else along the way, and if Shopify makes money along the way and I make money then, like, we’re good to go.

I want these to be in perfect alignment. I never want to shape a certain behavior that is actually not in the person’s best interest, but in the organization best interest or in another user’s best interest.

So i’m not taking a stab at any company in particular. But if the majority of what you do is, for example, creating advertisement opportunities, you are trying to shape behaviors to create more advertisement opportunities. Then the user’s best interest is not aligned with the second user for which you are actually designing for. This is what I care about. This is why I became a designer. This is why I want my design team to continue working for and working really hard. And that’s the goal that I want our team to not just do, but feel like they’re doing.

I want them to know that their design is in the best interest of literally everyone that it touches.

Peter: How have you shared that vision with the team? Does the team know this about you?

Cynthia: That’s a good question. I think the majority knows that I care about these things. We do have, like, conversations. We do have internal conferences. This is something I share when I’m interviewing as well. It’s a very common question that people ask, why do you still work at Shopify?

Like, yeah, money’s good, but I mean, I could have good money elsewhere, you know, and specifically a few years ago, it would have been very easy to just like seek a different paycheck. And this is what I tell people, I choose Shopify because it continues to be the place where the mission is the most aligned with my personal values and where everything I get to do gets to benefit everyone along the chain. I don’t think that’s the most accurate way of sharing that message to be fair. That’s something I might want to share a bit more. I thank you for the idea.

Jesse: Cynthia, what are you looking forward to right now?

Cynthia: Oh, great question. There’s a lot of super interesting projects that are about to ship and like, honestly, I know that’s a cheesy answer, but there are certain projects that have been so frustrating for a while because you just want them to ship for so long. And like every time I would use a product, I’d be like, Hmm, is it just me? Or is that complicated? Am I being dense or is this thing being dense, you know? And for so many reasons, sometimes honestly, just resource limitations at one point, or like optimization, it never gets fixed. And some of these are about to ship and they’re big changes. And this is super exciting to me.

I’m looking forward to the peace era in technology, if I may. Right now, we’ve just come out of a crazy stage of like, things are all like 10x-ing and it’s like super exciting, super exciting, super exciting, but like any bubble burst at one point, and we’re seeing that pop right now in the industry, unless you’re living under a rock, you’ve gone through 2022 and seen what has happened.

This, of course, has been very difficult for people involved, for employees, for everyone that is, this is very challenging for them, and it does impact your emotions and how you live and, like, your family life. Like, it’s very difficult. I’m looking forward to being on the other side of this and being in a more stable, trustworthy environment.

And I believe the best creative work comes from a place of people having creative courage. And to have creative courage, you have to have a sense of footing. You have to feel secure to put yourself out there and do super creative work. So this is definitely like the era. I call it the peace era that I’m looking for.

I’m looking forward to my kids that are growing up and are very, very exciting to watch. I’m excited about the general shape of Shopify right now. Like it’s, it’s fun. When people that are starting to work at Shopify ask me why I want to still work at Shopify, I answer because it’s value-aligned.

And when people at Shopify ask me, like, why are you still here? It’s because I still believe that I have more fun at Shopify than I would have anywhere else. And until I feel like that’s no longer the case, I’ll stay at Shopify and have that fun.

Jesse: Fantastic. Cynthia, thank you so much.

Cynthia: Thank you so much.

Peter: This has been excellent. Thank you.

Jesse: Cynthia, if people want to find you on the internet, how can they do that?

Cynthia: My very poor LinkedIn profile. You can find my book, tragicdesign.com. It’s currently on sale on Amazon, by the way. It’s still very relevant. I’m at conferences. You can find me on YouTube, but I don’t have a personal website.

Jesse: Fantastic. Thank you so much.

Cynthia: Thank you.

Jesse: For more Finding Our Way, visit FindingOurWay.design for past episodes and transcripts. For more about your hosts, visit our websites, PeterMerholz.com and JesseJamesGarrett.com If you like what we do here, give us a shout out on social media, like and subscribe on your favorite podcast services, or drop us a comment at FindingOurWay.design Thanks for everything you do for others. And thanks so much for listening.