35—The Actualized Design Executive (ft. Daniela Jorge)

In this episode, Peter and Jesse speak with Daniela Jorge, Chief Design Officer at PayPal, about vision, delivering on an end-to-end customer experience, growing and developing the next generation of leaders, taking advantage of design skills such as facilitation, and what she’s learned from working in more traditional companies.


Peter: I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

And we’re finding our way

Peter: navigating the opportunities and challenges of design and design leadership.

Jesse: On today’s show, Chief Design Officer for PayPal, Daniela Jorge joins us to talk about leveraging the superpowers of a designer to tackle the challenges of a leader, the leader’s role in developing the skills of their team, and leadership lessons from her time spent, both inside and outside Silicon Valley.

Peter: Daniela, welcome to our show. Thank you so much for being here.

Daniela: Thank you for having me here. I’m really, really excited. It’s lovely to see you both as well.

Peter: Jesse and I have been talking with a bunch of what I sometimes label true design executives, meaning senior, board- facing, hundreds of people in their organization, because we’re getting more and more of them in industry. There’s still not a lot, but there are more and more, and it’s definitely a trend that we’re seeing as these design organizations evolve and as companies continue to understand the impact that design can have.

At PayPal, your role is, at least according to LinkedIn, Chief Design Officer, I’m wondering how do you define that role? What are the responsibilities of the role? How are you held accountable? How do you spend your time? Just what does a Chief Design Officer at PayPal, at least, what do they do?

Daniela: It’s probably not too different, I think, than some of my other colleagues who are chief design officers, right? First and foremost, I’m responsible for the holistic experience of our customers, and at PayPal we have many segments that we serve, so that also spans all of the segments. Consumers, small businesses, large enterprises, developers. We even work on some employee experiences too.

So, and really thinking about those experiences from acquisition to obviously using our products all the way to online customer support and, you know, as the functional leader, for design or ux, I’m responsible obviously for the craft for how we’re delivering on all of these experiences with cross-functional teams.

And then equally as important, nurturing the culture, right? And making sure that we have an environment where folks can do their best work and where they feel like they’re growing and learning. So that’s what I’m, you know, largely responsible for, in terms of where I spend my time. It maps, you know, closely to those responsibilities.

The Four Components of Daniela’s Role

Daniela: So the first thing is on the strategic end, is really working with partners and with the team on defining vision. So we do quite a bit of, you know, where possible, like, working backwards exercises where we get everyone in a room and we think about what could the experience be for a PayPal developer? What could it be for a PayPal consumer? And then helping to shape that and visualize that so that it can help drive alignment and excitement for what it is that we’ll be delivering for customers.

So that’s number one is, almost that sort of facilitation of vision, right? Vision in my mind is a team sport. So we spend a lot of time facilitating those types of workshops. We have a few actually happening this week.

The other piece, which was something that we started two years ago, our customer experience reviews. So I’m part of a two- person customer experience council, and we review almost every experience that goes in front of our customers.

There are weeks when we have two or three sessions a day, where we’re looking at all of these customer- facing experiences. We’ve done, I think, over a thousand since we started.

So, and our role is, is twofold. One is to bring in that, that sort of fresh perspective, right? We, we obviously know what the company’s trying to do, we know what the customer needs are, but we’re not too close to the actual work product. So we’re coming in somewhat with fresh eyes.

But more importantly is also connecting dots. Right, Right. So we, we might observe areas where perhaps we’re showing up, like our org chart, which we all know is something that I, I think design is oftentimes trying, trying to address. So we connect those dots, we mind those seams in between teams and solutions. And then also connect teams that should be talking to each other, for various reasons, either because they’re creating redundant work, or again, not necessarily thinking of how one plus one can equals three, if they join forces and how they’re thinking about a customer problem.

Then obviously I spend a lot of time, you know, focused on growth and development of the team, so, so running the organization, investing on individuals and their growth and, you know, spending time with my direct reports.

And then the last thing is just non-UX or product work. So for instance, I’m one of the co-executive sponsors for Aliados, which is our employee resource group for Latinx, and allies. I participate also in the employee resource group for, for women at PayPal. I’m an ambassador for PayPal’s leadership principles. I do quite a bit of mentoring outside of just UX as well. So these are things that, I spend time on that are outside of what you might think a chief design officer might be doing.

Jesse: Mm-hmm.

Where Design sits organizationally

Peter: There’s a lot there. A lot to unpack. I think we might just be spending our time going through each of these and understanding it. An organizational situational question. And then a metrics question. The organizational situation question is like, where are you in this organization? Right?

A lot of even senior design leaders report up through some product function. Is that true of you or do you have a different organization? And then given all of these areas that where you spend your time, what does your leadership hold you accountable for? Are there metrics or numbers or outcomes that they’re expecting you to drive towards?

Daniela: Yep. We sit in the CPO organization at PayPal and CPO at PayPal includes product, engineering, design. So it’s, you know, more expansive than just product management. So part of that three legged stool. Though, we, and then we also work very closely with legal and risk and compliance. But we sit in the CPO organization in terms of metrics.

We don’t have necessarily hard metrics that I own from an experience standpoint, but we define those per project, right? So if we have a specific project that’s around helping customers achieve a specific goal, those are defined at the initiative level. That’s where more of the hard metrics live.

So for us, it’s just really the quality of our experiences. Are we seeing customers call into customer support because perhaps things are not as clear as they should be? How are these experiences testing with our customers? And then are we able to influence roadmaps to make sure that those are being prioritized and that are part of, of a team’s delivery plan.

So it’s a bit more qualitative in that regard. And then organizationally, of course, there are metrics, right? Things like attrition and whether or not we’re hiring within a specific timeline. Engagement scores for annual surveys, et cetera. So, in the people area, I would say I obviously have hard metrics. On the UX area, they sit more at the initiative level. And then I think that there’s always that qualitative feeling of whether or not right, the experiences are where they need to be.


Jesse: I noticed there’s just a lot of vision work in the description that you laid out. And it’s interesting because I see a real challenge for leaders as they get more and more removed from the roll-up-your-sleeves, do-the-design-work kind of work. Product vision starts to get to be kind of a distant thing for those leaders as their concerns become more business-oriented, more operational, more around the orchestration of the design engine, rather than being oriented around the outcome. To what extent is this an element of your style that product vision is so central to how you perform this role?

Daniela: That’s a really good question. You know, as you’ve probably experienced yourselves, I think that there’s always this separation of, of design leaders who are either visionary or operational. And I actually consider myself much more on the operational side, right? What I’ve done is like, I’ve really figured out how to lead at scale, how to work well within, within large companies.

I don’t consider consider myself a visionary leader, however where I think I, my strength is, is on the people side. How do you drive alignment?

Jesse: Mm.

Daniela: How do you drive excitement? And, and to me that’s where vision is really helpful. It doesn’t mean that I’m the one crafting the vision or even that design is the one completely defining the vision, but it’s about how do you get everyone together in a room on calls you know, whatever the, the forum might be, and then have a framework that helps to tease out that vision and package it in a way that’s accessible to everyone, right?

That whether we’re showing it to the person who might be leading customer support, to someone in sales, I think that that’s where design has a real strength. And, and where we can really help is to drive that alignment and to also make it feel real so that everyone can get aligned around that same outcome and that same end state in terms of this is the North Star, it may not be, again, that detailed execution plan, but then teams can come up with their own execution plan aligned to, to that north star.

Peter: What degree were you the initiator of the importance of vision? Was that something that you helped others around you realize that vision can be a tool for alignment? Or was that something that was realized prior to you, and you’ve been delivering on that? ‘Cause I’ve seen design leaders want to do vision work, but their, their partners are like, we don’t need that. We just need to ship things.

And so I’m, I’m just, I’m wondering where the impetus for vision is generated…

Jesse: The cultural permission almost.

Peter: Yeah, yeah.

Daniela: Yeah, it, you know, it, it varies and I would say that it’s probably varied for each situation and also depending on the altitude of the vision that, that we’re driving. Sometimes it might be that there’s a product area, and I might notice that teams are swirling. And people are coming in and it feels like they’re at odds, right?

Or, or maybe the team is aiming too low and you’re like, ah, if we could just get in a room and think a little bit bigger and that’s where, not that that I think, you know, workshops, design sprints, whatever it is you wanna call it, not that those are always the silver bullet, but that’s where I found it’s really easy to convince people to just dedicate like three days, five days, to get in a room to, to go dream little bit bigger and to get to that alignment. And every time we’ve been able to then convince people to do that, they’re sold, right? They never wanna want to work another way. They don’t want to kick off planning a different way.

So, so that, that’s what’s worked mostly, especially when it’s like at the, that product level, that initiative level. And then of course there have been times, you know, maybe there’s a very senior executive who has a vision and who comes to us saying, “Hey, can you just help us visualize this?” And through that process, you kind of influence the, you know, it a little bit more so that we’re not just the, the ones coloring in between the lines, but again, we bring in an approach where we can also help shape that narrative and, and shape it a little bit more, bring in that customer lens into the thinking. And then of course, help visualize it, right. Since that is a, a key skill that we have.

Jesse: Mm-hmm. .

Peter: And then how, how do you operationalize a vision, right? One of the concerns around visions is you get these very pretty concept cars. You get these very pretty imagery and videos of some future state experience that then people lose sight of over time and they just go back to doing whatever they were doing.

Do you have mechanisms to turn these, this vision work into something that gets metabolized within these teams.

Daniela: Yes. And, and again, it, it’s, it’s varied over time. So one of the things that, even though I’ve participated and, and driven even exercises where it was like a five year vision, I, I much prefer to drive shorter term vision activities. I feel like those are, right, much more achievable to, to the point that you’re making.

I, I have found that five-year visions are very inspirational, but don’t always translate into action. So one is just picking the right timeframe for, for defining that vision.

And then the other piece, which I think is really critical and important is your vision is a rough blueprint. so then you can actually work backwards from it and actually saying, if this, if these are the outcomes that we want to achieve or what we want to eventually deliver for customers, right, what’s the first step? What’s the first version of, of what we’re building, right? Are we going to build a living room, a kitchen, maybe one bedroom and one bathroom, even though eventually we want to have this amazing mansion? So, so I think it’s then that, that discipline of being able to work backwards from that vision and having that first step defined.

And then to add to it also not being super precious about the vision, because I think one of the beauties of, of the work that we do is, is what you learn in the process, right. So I think it’s helpful to have that north star, but you also need to leave that open, as for learning as you go and, and for having customer input shape where, where it should go because, and what you may end up in version three may not be exactly what you had figured out and, you know, for that full vision two years ago.

So I think it’s about then working backwards for the V1 and then iterating your way towards that end state.

Jesse: You said earlier that defining that vision is a team sport. I’m interested in who the players are. And how you call those players to the table when, you know, sometimes the, the interest isn’t there, sometimes the motivation isn’t there sometimes the belief in what you’re doing isn’t there. How do you bring the right team together to create a successful product vision?

Daniela: You know, at PayPal we’re really lucky that, that I feel like everyone wants to be included and participate and when, I mean everyone, right, we’ll have legal in the room. We’ll have risk and compliance in the room and, and it’s, those are always the best, in my opinion is when you actually have, not only in terms of what comes out at the end of that five day session, but in terms of then how the project itself plays out, right?

Because people were included upfront and they actually have that, that sort of buy-in and that motivation and they understand who the customer is, they understand what, what we’re going to be delivering, what the outcomes are. And then they’re part of solutioning throughout because they were part of, of that inception phase.

So, so to me, the more cross-functional, the better, and at PayPal it hasn’t really been a challenge in terms of, of engaging others. When I think about other companies where perhaps that, that has been more of a challenge we’ve been really thoughtful about thinking about the activities and then figuring out, like what’s, you know, how can you make it more accessible so that someone can maybe come in for, like, two hour kickoff on, you know, immersion on customer insights, and then maybe they just come in for like a couple of checkpoints so that they’re not from the get-go saying, “Oh yeah, I have to commit five days” to something that, you know, feels very fuzzy and feels like a, a big time commitment. So, so that really helps.

It’s just really thinking about your audience and thinking about how do you close that gap between where they are and where you are. So that has worked well in, in other contexts.

Facilitation and customer-centricity as design leader superpowers

Jesse: Yeah. You know, it’s interesting. As you were talking, I noticed that it’s hard for me to imagine a different C-level role in most organizations, being someone who claims workshop facilitation as a core part of their skill set and their value. And I’m curious about how that plays out, how your designerly sensibility plays out among the other senior executives that you have to engage with.

Daniela: So first of all, I think that that’s awesome, right? That we can claim that I think that those differentiators or, like, superpowers and things that you should lean into. So, so I think that’s a great observation. And if anything, again, I think that that’s something that we should highlight.

And I think that that’s how it’s viewed by my counterparts. They appreciate that, that we actually have that skill. I’ll give you an example. We sometimes do these workshops for contexts that are entirely outside of, of product. We’ve done it with, done it with finance, we’ve done workshops around like pricing strategy, right?

So, so I actually think that they see it as a very unique skill that most people actually don’t have naturally. And, and, and they, you know, it’s, it’s usually welcomed and sought after. And, and perhaps, design thinking aside, right, but perhaps it is a unique skill that we haven’t necessarily always leveraged and celebrated ourselves to, to position ourselves differently from, from our counterparts in, in senior executive roles.

Jesse: What are some of the other design superpowers that you think are especially important that especially come into play at the executive leadership level?

Daniela: One of them is obviously, you know, this will sound very obvious, but I think it’s being customer-centric. One of the things that, that I often hear is that everyone knows that I’m always acting on behalf of the customer. So they see me as being very neutral. So when you have teams that might be at odds or have conflict, they feel like if they bring me into the conversation, I’m going to be there with no agenda other than doing what’s right for the customer and the business, of course. But I’m a neutral party.

I think being a horizontal leader also helps in that regard. You know, I’m not claiming that this is just a design thing. I think that there’s other functions that, that might be horizontal, that have a similar leverage.

So, so I think that that’s a key one, is I always bring the conversation back to the customer. It’s how I’m wired. It’s how many on my team are wired, right? So we think that way and we can bring the conversation back to that. And oftentimes, I think, cut through things. that perhaps, you know, would be a little harder if you weren’t centering the conversation around the customers. If, if folks are just more concerned about ownership or what their specific products are, what their specific, you know areas of responsibilities are.

So, so I think that that’s a, a key, a key strength. Connecting dots. We talked about this already, right? I think most designers and design leaders are able to zoom in and zoom out. So we’re able to zoom out, zoom way out, and figure out how to connect dots and think about the, the holistic experience that others may perhaps not be, be able to do so easily.

And then the zooming in part, which is like you’re able to do that and yet you’re able to zoom in and talk about a word or a pixel on the screen, right, And care equally about the craft and the fit and finish.

Jesse: mm-hmm.

Peter: Given what I assume to be the size of your organization and the, and the surface area that design covers across PayPal, customer experiences, merchant experiences, you mentioned internal employee experiences, all that, just how detail oriented can you get? Or do you, do you have like themes, like, this quarter I’m all about this audience and I’m gonna kind of dig deep and I’m gonna let the other one slide.

Just because one of my concerns and, and let me, let me pose it as a little bit of a provocation. Daniela shows up at my meeting and swoops and poops about something that she doesn’t actually have a lot of context. I’m trying to figure out how do you not overstep, not claim that you understand something that you don’t in an area, but still maintain that level of depth that you need to provide credible meaningful context and feedback to these teams. Without working 120 hours a week to try to keep on top of everything.

Daniela: Yeah. Which I don’t do by the way. I, PayPal is really good that way and I’ve also learned that over time. So, so in a couple of ways, and you alluded to one of them first, they’re every quarter or so and timeframe may vary, I do have a couple of priorities that I’m closer to, right, that I’m involved much more beginning to end.

And then myself and my leadership team, we sort of also look across to figure out like, you know, who’s focusing on what, so that we have coverage on, on the highest priorities. And, and that seems to work really well. And then the experience reviews that I mentioned are really helpful. So that is how I then look at everything else, which is these daily, you know, sometimes two, three times a day, we have different project teams coming in and sharing work, and they’re doing it at different phase in, in their project. So we’re seeing it again, also beginning to end. And in those sessions we sometimes do get it, you know, we, we go all the way to discussing product strategy policy all the way to, to a pixel on the screen. And it’s, you know, it’s helpful in the sense that we have a dedicated forum where we can do that.

So, so teams are coming into these sessions expecting to get feedback at varying levels. And as we know, right, that that can be sometimes hard for teams because you’re right, I don’t have all of the context. So they do have to spend some time usually giving us context. Even if it’s a team that we’ve seen before, if three months have gone by, right, they have to reset context oftentimes, or even remind us about all of the details and intricacies of, of their specific project.

But hopefully we still, you know, add enough value in terms of, not being so close to it, that, where I think that’s one of our values is that we’re not so close to it. That, that we don’t, you know, we’ve all been in teams when we were designers and, and you’ll make trade offs and you’ll make decisions because you’re so close to it and sometimes you miss that you’re doing that when you’re so close to it.

So we’re able to challenge some of those things. We’re able to remove roadblocks for teams. That’s another benefit of, of these forums. And then again, just look at how, how is everything coming together? Right? How are all of these experiences hanging together because we’re looking at, at so many touchpoints.

The CX Council

Peter: Let’s unpack the CX Council. You, you mentioned it as part one of your core areas at the outset, and I’m, I’m very intrigued by it. Who’s on it? You know, what, what’s the, makeup of it? What,

Jesse: Who’s the other person on it?

Peter: Right. I think you said it was only two people. And then, what teeth does this council have? Is it, is it more like, so I have behind me the book, Creativity, Inc. By Ed Catmull from Pixar, right? And they talk about the brain trust, where there’s this group of people who know a lot and give you notes, but it’s up to you, in this case as the director, to take those notes or not. But you probably, you should probably listen to the, you know, some of the best directors who’ve ever done this work, if they’re giving you feedback.

Are you giving it in in more of this spirit of mentorship and guidance and hey, did you think about or is it a bit more directive? So help, help unpack this CX Council for us.

Daniela: Sure. So, So the CX Council, John Kunze, who is my manager now, wasn’t when the CX Council got set up. So when, when the CX Council was established, John was responsible for our consumer segment, and I was running design. So we were asked to, to form the CX Council by, by the CPO at the time. And then John was, John’s role became, essentially to look after CX for PayPal.

So he now is in a different role that’s much more dedicated to this notion of actually looking at CX horizontally. And, I report to him now.

So, so we’re the CX Council, if we will, if you, you know, had the chance to meet John and, how I am, like we, we don’t carry that label around. I’m not like big on hierarchy and labels. So, but so we’re the, the ones who were always in these sessions and the consistent sort of reviewers, right, in, in the experience reviews. And then we bring in all of my direct reports. My peer in the CX group who, who runs project enablement is also part of, of these and you’re right, 99% of the time, we’re primarily giving suggestions.

If there’s something that we think is a absolute showstopper, we’ll call that out and actually say, Wow, no, we have to, to reconsider this. That rarely happens. It’s maybe, you know, only happened a couple of times, so it’s usually much more suggestions and we’re very clear with the teams that it’s up to them to actually figure out how they want to prioritize the feedback and, and what they want to take away versus not.

Peter: I think the most obvious question is, what’s the difference between CX and UX? What, what does CX encompass that UX maybe doesn’t?

Daniela: That’s a really good question. You know, so in John’s remit, his team works with customer support. For instance, looking at things like top call drivers and you know, how should we be thinking about prioritizing experiences to address those. So it’s, it goes beyond I think, some of the pro–, and not that we’re not involved, of course, UX is involved then in doing things in the product that might, might help with, with customers having to call because they’re having issues. But, but it will include things like policy and, you know, it’s, it’s a bit broader than, than just UX.

Working end-to-end

Peter: I’m trying to understand the, end-to-end here in terms of engaging with the customer experience, right. You know, you’ve got, if you look at a standard customer lifecycle from, let’s start at the beginning, marketing, customer acquisition, there’s some conversion experience, you’ve got the product experience that your teams are probably most responsible for, and then there might be some type of service and support experience. Sales might be involved there, I suppose. Given your, your enterprise orientation, do you and John cover most of that end-to-end customer experience? Are there others that get brought in?

Daniela: It varies per segment. So, so let’s talk about the consumer segment ’cause that’s probably the, the easier example to follow through.

And before I, I do that, I’m also responsible for our paypal.com website as an acquisition channel. Not just from a design perspective. So I am actually, I have a team of product managers. We’re responsible for the platform, the channel. We work very closely with marketing on, on that and also SEO. So not something perhaps you would typically find under a chief design officer. But it was an expansion of my role a couple of years ago and I have really enjoyed taking that on.

So on consumer, we’re responsible for SEO. We’re responsible for all of, you know, for the pages that a, a customer might land on when deciding whether or not to sign up for PayPal. Then once they sign up, or if they’re logging in, that’s where all of the product experiences start and we work on with all of the teams that, that are responsible for those logged in experiences, if you will.

And then we work with our customer support platform team that is responsible for online help, chat, etc. So we work also on, on those experiences and some agent experiences. So if someone calls in the tools that the agents are using, we also work on, on those experiences. So it is fairly end-to-end in, in terms of how we work.

And then of course, there’s, you know, differences if you’re looking at large enterprises primarily where the experience might be a little bit different because obviously there’s a big sales component on the acquisition.

Jesse: You know, you have so many different experiences that you’re responsible for, this whole diverse array, and I wonder where you choose to personally invest yourself. Where do you get hands-on in all of this, versus having a group of trusted lieutenants that you give guidance to, but otherwise really let them have autonomy over some segment of that vision.

Daniela: So it’s probably not a versus, right. I, I’m very fortunate that I have a group of trusted lieutenants that hopefully have autonomy and, and who are, who are driving the work and partner with, with others. So it’s really much more around key initiatives that, that are high priority for the business that where, you know, it’s helpful for me to be involved, for our VP of Design to be involved and to stay close to it. Just, just because of its importance and because it might require, for instance, a little bit more orchestration between the acquisition part of the journey or the support part of the journey where, we can be that glue and provide that level of, strategic input, if you will.

So, so it really varies. It’s usually not like one area where I would say in this area, I’m always spending my time. It changes, you know, pretty much on a quarterly basis I would say.

Driving alignment when you’re not there

Jesse: You talked earlier about the importance of driving alignment. And these kinds of interventions and course corrections are a great way for you to be able to drive alignment across your teams as a design leader. But it is very hands-on and very intensive. And I’m curious about the mechanisms that you’ve developed for driving alignment when you can’t personally be the one to provide the guidance to every team.

Daniela: That’s a, a, a great question. I think, I mean, part of it is just having an awesome team, right? That I, that I know that they’re going to be there asking the right questions, setting the right goals with, with their partners, et cetera. So I think that that’s number one. Without that, there’s no way that I would be able to scale myself or trust that, that we were doing the right things as, as a UX organization.

We’ve talked about the, the customer experience reviews. We encourage teams to come in as early as possible into those…

Jesse: mm-hmm.

Daniela: …right, because it’s much easier for us to figure out if teams are thinking about the right customer problems, are they considering other aspects of the experience, other teams that they need to be engaging if they come in earlier than, than if we’re already at the sort of like, here’s the solution.

And then, then now we’re saying, Wow, you really need to go talk to this other team because it’s really important that what you’re doing works with, with what, you know, this experience that, that they may be responsible for. So, so some of it is just figuring out these channels for having visibility at the right point in the process on our most critical initiatives.

Leadership skills

Peter: In your job as kind of bringing up this team and helping them be their fullest selves, what are the kinds of things that you find that you often need to help them better understand now that they’re operating perhaps at a level that they hadn’t operated before?

Daniela: They’re probably, they are a lot more, I think, around just leadership skills, right? And so, for instance knowing that, yes, we may have a vision, but we may have to make tradeoffs in terms of what we’re able to do in the short term. And that that doesn’t mean that you still can’t be pushing and challenging the team to continue to deliver more, more better experiences for the customer.

So, so a lot of it is that we talk about is perspective, patience, right? Figuring out how you’re influencing, figuring out how you can sometimes measure progress in small increments. Because I, because the job that we do is hard, right? And especially because I think we are able to see what it should be and what it could be. And that isn’t always what is happening in that moment or in the short term. So, So a lot of the time that we spend is actually, I think just talking like regaining perspective so that folks don’t get discouraged. And so that we, you know, so that everyone collectively as a leadership team can do the same for our teams.

And, and have them feel excited and, and sort of get the perspective that like, yeah, but if we look at where things were six months from now, look at how much we have actually achieved, then yes, yes, maybe there’s like, you know, so much more that we could be doing, but do we feel like we’re marching in that direction and do we feel like what we’re doing today, if we look at it six months from now, we’ll be like, Wow, that was pretty awesome, right?

So, so I think a lot of it is just, like, perspective, patience, having a bit more of an optimistic, in terms of how we are having impact and, and not necessarily, I think getting discouraged if it doesn’t feel like you’re not getting to the end state overnight. It feels like a lot of conversations are centered, you know, much more on that. And, and, and just using each other, I think, as sounding boards and then recognizing the progress and impact.

Peter: There’s this concept that comes from executive team dynamics around the first team. And typically the first team is not your or your functional organization, right? It’s your peers. And I’m wondering, one, does PayPal practice first team, do you consider product and engineering and customer experience, your, peers?

And then, two, you know, this, this sharing that you’re talking about that happens amongst your leadership team, is that similar to maybe conversations you’re having with your peers or, or is the tenor of those discussions different?

Daniela: So I love that you brought that up. The Five Dysfunctions of a Team is my very favorite leadership book. Highly recommend it. I bring it out at every leadership offsite I have, and talk about that concept with, the team, especially because in design I feel like we have two first teams, which, which just makes things a bit more complicated.

We’ll get to that in a minute. I think PayPal is very cross-functional and very collaborative. So even though we don’t necessarily use that term of a first team, we behave that way. And then I certainly behave that way, right? I spend just as my much time with my cross-functional counterparts and building those relationships potentially even more time than, than with my direct team.

And I do believe that it’s critically important for, the, you know, the UX team to lean on each other. When I was at Intuit, which was when I was first introduced to this book, I had a manager that actually said that he would consider it a success if he found out that we were all meeting without him.

And that really stuck with me,

Jesse: Hmm.

Daniela: and that that’s been one of my goals, right? It’s always to get to that point where my direct reports are meeting with each other and excluding me from conversations. I think that that’s a really good sign of a healthy first. So, so, yes, a hundred percent, subscribe to that. Peter.

Peter: And then you mentioned the dual first teams, right? And is there something different about design, maybe from other functions, where we can’t let go of our design first team the way maybe other functional leaders can?

Daniela: I think that that’s true for most functional…

Peter: Okay.

Daniela: …organizations. I’ve, I’ve never double-checked this with product management, but I would assume it’s the same, but I, but I definitely know talking to engineering, marketing, et cetera, it’s true, right? Which is you have to balance the fact that you have your functional first team and then you have your cross-functional first team.

So, so for instance, when a designer introduces themselves on a team, they may say, I’m a Venmo designer. They’re leading with usually, right, the cross-functional team that they’re part of, and then like their functional team that they’re part of. And you have to balance the two. And I think, you know, in a centralized partnership model for, for that to work well, the reality is you’re actually spending a lot more of your time with your cross-functional team. I use this, I hate to use family analogies in the context of business or work, but I, I do use one that I think is quite effective, which is, right, you’re, you’re sort of born into design, but then you marry into the cross-functional team. So that means you’re spending most of your time with that family, but you’re still having Sunday dinners and your DNA is part of the family that you were born.

Peter: Mm-hmm.

Daniela: And that, that usually is what I’ve seen, you know, be more effective is when you can strike that balance.

Compare and contrast Silicon Valley with more traditional companies

Jesse: To take a step back from PayPal for a moment. You’ve been a designer for a very long time. You’ve been a design leader for a very long time. And almost all of that experience, as far as I know, has been in Silicon Valley, which has its own unique culture, which people outside far and wide look at and speculate about and have their curiosities and their envies and often try to emulate.

And I wonder, in your experiences of Silicon Valley culture, what are the aspects that people should seek to emulate and maybe not seek to emulate based on your experience?

Daniela: You know, it’s actually interesting. I’ve worked in some very traditional companies as well. So I started my career at Kodak. I worked at Kaiser Permanente, and then I worked at AT&T.

So I have had, I think almost like the two sides, right? Very tech, Silicon Valley companies, and then some companies that have been around for you know, more than a hundred years.

So, what was interesting to me, and AT&T just being the more recent one, was that yes, AT&T wanted to emulate and learn about, like what was the, you know, the magic secret sauce that that was happening in Silicon Valley.

And, and when I got into the company, I, aside from obviously the sheer size and scale of the company, there were many more similarities than differences in how we approached product development. Between the two companies, there were many more similarities in terms of the caliber of the talent. So, so I found more similarities than differences.

There were some things, obviously, right, being in these companies, I think the thing that always was the most different was that the core of the business isn’t necessarily, right, the digital products that you might be working on. So that’s a significant difference in terms of just the level of importance given to it and the fact that not everything revolves around those experiences. Like there’s a whole other business that, that the company is, running, right, And that, that at the end of the day is, is most important.

So it’s more of a support function in some ways. And even the way that you work, it might be that you might be in the CTO or CIO organization and the BUs have to actually fund those digital projects and you don’t get started on projects until they’re funded. So those things are obviously fundamentally different than when you’re in a company like PayPal or others where software is the business.

The other thing though, that was remarkable at AT&T and then at Kodak and at Kaiser was the caliber of leadership. So in Silicon Valley, I think functional background is really important, right? And that’s how all of us rise through the ranks. It’s like you’re an amazing engineer and then one day you’re a VP of Engineering.

Jesse: Right.

Daniela: Same for design.

And in these larger companies, that’s not the case, right? They usually groom people to become GMs. And the way that you do that is that by actually rotating through a bunch of different functions and, and you don’t necessarily have like a very clear, functional background. So, so what was interesting there is that perhaps that functional background in some cases was missing and, and should have been there, depending on the role that they were doing.

But on the other hand, they were amazing leaders, because they had been selected and groomed to be amazing leaders.

Jesse: Mm-hmm. And what did you feel that they brought as leaders?

Daniela: Some of it was just, you know, obviously on the, on the sort of like running a business side. It was just the rigor and the discipline and the structure…

Jesse: Mm-hmm.

Daniela: …right, of, how you run a business, like the operating mechanisms and, and, and I think the clarity, et cetera, it was just, I think that there was just a lot more rigor and discipline.

I think the, the people side, I was perhaps for- fortunate enough where I think that they, they also just had much more experience in training in how to lead people, how to lead large organizations, how to motivate people, how to communicate, how to ensure alignment of, of you know, large groups of people, where I think if you’ve only done, like, if you’re an amazing designer and all of a sudden you became a leader, like you’ve got no training in how to do that, right?

It was just because you were really good at your craft.

Jesse: Yeah. That’s definitely a recurring theme that I’ve been hearing among my coaching clients for sure.

I’m curious about how you’ve seen the relationship between design and other functions evolve over the course of your career. Because as we’ve been talking to other design leaders and we’ve been hearing about the march toward the executive level, that design has been undergoing over the course of the last 20 years.

What is the most dramatic difference between being a design leader now versus when you started out as a design leader some number of years ago.

Daniela: You know, it’s funny, I, was really fortunate. Where I feel like in the companies that I worked at Design had an opportunity to work across a broad set of, of areas in the company. So for instance, you know, working closely with marketing, working closely with product, working closely with engineering and, and other areas.

But I feel like that if I just look, more broadly, I feel like that that’s probably the biggest difference is more than just the traditional sort of product and engineering functions. Realizing the power of design and how to partner with design and design realizing how to partner, right, with, with more functions than the typicals, product and engineering functions.

So as I talk to other leaders as well, many of us get involved in designing office spaces back when the world was very, you know office space focused. Or we might again get pulled into HR programs. So I think it’s that expansion of, of where design can play a role that, that I have observed, that, is a great, great thing to see so that we’re not just boxed into, we’re the people who design screens on the product, and that’s the only place where we add value.

So, and I think it’s, it’s both ways, by the way. I, you know, my advice to people is always be curious about every function in the company and figure out, like, how they operate, what matters to them, how you can add value, how partnering with them can add value in terms of our agenda of delivering better experiences for customers or employees.

leadership growth and development

Peter: You mentioned one of your areas of focus was the growth and development of your team, and then we were talking also about developing leadership skills, the, the conversations you’ve had with your leaders and helping them reflect, but then also what you saw when you were outside of Silicon Valley in these, in these contexts where leadership is seen, you know, almost as a function in and of itself, distinct from your delivery functions of product or engineering or design. What have you instituted to really help the development of the people in your organization? How much have you had to do on your own versus maybe aligning with HR, you know, firm-wide learning and development function? You know, how, how have you invested in it? What kinds of things have you done that you found are effective, maybe more effective than, than people might realize? Just kind of curious how you think about that, that growth and development activity for your organizations.

Daniela: Yep. So on, on the more formal side, right, of HR programs, we do get access to, to things like coaching and development 360 programs and make use of all of those, right. I find those hugely helpful, so that folks can be getting feedback and actually getting feedback from, from coaches that, that, like, that’s their, their expertise and their full-time jobs.

So we have that in place for, for most of, of the leaders on, on my direct team. And, and then as possible also for, for other levels. Aside from that, I, I’m definitely someone who, you know, coaches much more in the moment. So I find that it’s really important to actually have those direct conversations about what I’m observing or seeing, and then also creating the space for them to bring in, here’s a challenge that I’m encountering, how, how might you go about it?

So those conversations are always part of every interaction that we have. and they’re happening at all times. And again, I think that it’s that sounding board, you know, model that we were talking about or, or approach, which is part of it.

I go to them as well for advice on things. So, so just creating that safe space, I think for having these conversations. Being really open and, and clear about, like, what each of us are working on, including what I’m working on. And then we support each other, right? So if someone might be working on, I dunno, presentation skills, to senior stakeholders, right?

I’m– they’re presenting, I’m in Slack and being like, Wow, the way you just said that thing, that was amazing. Do more of that going forward, right? So that, it’s that sort of like real time feedback loop. And so that it’s also not like this big thing or like once a year thing where you’re coming in with like a list of things that they should be working on and, you know, and, and, and you don’t wanna be surprising.

So it, it happens, I think, much more ad hoc, but also much more regularly throughout the week, I’m having these, these conversations with, with folks on my team.

Peter: How much do you stress that, kind of, at all levels of the organization? Like, do you make sure that all of your managers are coaches as well, and how do you help everybody tap into that kind of coaching awareness so that when you’re not in the room , you feel confident that people are getting that kind of helpful feedback.

Daniela: We’ve done a number of things. I would say this is a focus area for us now, just because we have scaled so much and also have a lot of new managers, and we have fantastic managers, but we also have folks that are new to being managers.

One of the things that, that we’re hoping to bring back was something that when Dorelle Rabinowitz was on the team, she introduced this and it was really effective, which was manager circles. So we created these manager circles where managers were co-coaching each other, if you will. So folks would come in and they would speak about different challenges that they had and, and it would be a safe space with folks that, you know, of the same level, a couple who were more experienced. And these, these were just a great way of, of ensuring that folks were getting support from each. And as, as they were getting into managers, sharing best practices, et cetera. So shout out to Dorelle ’cause that was a really effective program and something that we’re, we’re looking to, to bring back as well.

Jesse: As all of these practices and processes continue to evolve the challenges that we’re taking on are evolving as well, as you touched on. And I’m curious about what you’re excited about for the future, for the future of design broadly but also for the future of design and its ability to have a meaningful impact on business.

Daniela: The first one we already touched on, which is right, how can we help businesses center decisions on the customer?

Jesse: Hm mm-hmm.

Daniela: And I’m someone who, perhaps because of my time at Intuit, I, I truly believe that you don’t have to, you know, make a tradeoff between business results and delivering for the customer, right?

If you put the customer at the center of business, results will generally follow. So, so that’s what always gets me excited. What’s, it’s what gets me, me out of bed in the morning. The other piece is product inclusion or responsible design.

So this is a program that we started at PayPal, believe it was early last year.

Benjamin Evans joined us to, who had been leading similar programs at Airbnb, joined us to, to lead this at PayPal. And, and to me, maybe it’s more of a duty, right? I feel like it’s, it’s truly important for us to make sure that we’re putting our powers to action for good and that we’re not necessarily overlooking how we might be creating experiences that may exclude certain groups of people that may actually cause harm intentionally or unintentionally in, in many ways.

And again, making sure that, that that’s front and center for how we actually deliver product and, and create solutions. So that’s something else that I personally am, am very excited about,

Leading through difficult times

Peter: Following a little bit on what you were just mentioning around matters of inclusion, and not just in the United States, but, but globally, things have been fraught for at least a couple years, pandemics, et cetera.

And there’ve been some challenging times to, to lead through. And more specifically, there’s a lot of news around layoffs and so folks are starting to get anxious, right? Either they’ve lost their job or they’re wondering if they’re gonna lose their job. What have you found that works to help the people that you’re responsible to, see forward and acknowledge the very real challenges they’re facing, but also maybe be able to, I don’t wanna say move past them, but, not allow them to overwhelm them. How do you do that at your level? Keep a whole org buoyant, when things can get challenging.

Daniela: It’s a, it’s a really good question, right? And I don’t think that any of us had playbooks to that, that helped us figure out how to lead through a pandemic or lead through, you know, high inflation. I think all of the challenges that, that are part of, of just being a human. In the world right now. But I think that there’s definitely certain things that as, as a leader, you can do to, to help. The first one is just acknowledge what is happening, right? And acknowledge that things are difficult. Acknowledge what, what, what is happening externally. None of us can completely like just section that off and say, Well, I’m leaving that all behind and now I’m in this meeting and none of that is impacting how I’m doing my work, how I’m showing up as a human.

So acknowledging it, being transparent whenever possible, and, and that’s something that I always aim to do as a leader, is providing as much transparency and context, right? It’s, I think it’s very easy when, when you’re in a leadership position to forget that you have access to a lot more information and context that a designer on the team might not.

So even if you have to deliver difficult news or difficult updates, I find that people can process that much better if they actually have context about why that decision was made, right? And why we have to, to take a certain direction. So providing context, being transparent. And then lastly, providing safe spaces for people to share how they’re feeling, how they’re doing, how that’s impacting them, whether it’s at work or at home.

So those are three things that throughout. I, I would say the last two, three years we’ve really aimed to do, I have aimed to do as a leader and we have aimed to do as a leadership team. And that I think are also very true for how PayPal is and the kind of company we are.

Jesse: Daniela and thank you so much.

Peter: This has been great. Thank you.

Daniela: Absolutely. Thank you. I really enjoyed the conversation.

Jesse: Of course the conversation doesn’t end here. Reach out to us. We’d love to hear your feedback. You can find both of us, Peter Merholz and Jesse James Garrett on LinkedIn or on Twitter, where he’s peterme and I’m JJG. If you want to know more about us, check out our websites, petermerholz.com and jessejamesgarrett.com You can also contact us on our show website, findingourway.design where you’ll find audio and transcripts of every episode of finding our way, which we also recommend you subscribe to on apple, Google, or wherever fine podcasts are heard. If you do subscribe and you like what we’re doing, throw us a star rating on your favorite service to make it easier for other folks to find us too.

As always, thanks for everything you do for all of us. And thanks so much for listening.