Sidecar Leadership — with Jennifer Lai Stern

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Sidecar Leadership

April 26, 2024 Brand Leadership Business Growth Career Growth Design Leadership Leadership Management Strategy

Guest Speaker

Jennifer Lai Stern, Head of Brand Studio at PayPal

Jen Stern is an agency-grown creative with 20 years of advertising experience with a background in art direction. She has worked at agencies in New York, L.A., and San Francisco and is now working in-house at PayPal. Her current focus is across the entire brand experience, including advertising, communications, product, hardware, and events. She leads a multi-disciplinary team that builds out capabilities across creative and production with a focus on creative innovation. She is passionate about cultivating creative culture, fostering collaborative teamwork, and supporting creative health.

Sidecar leadership is the transformative management strategy you’ve never heard of.

Sidecar leadership guides teams to discover innovative new solutions to their most important objectives—all without micromanaging and valuing output over empathy. Jen Stern, head of Brand Studio at PayPal, joins host Adam Morgan to talk about how to lead creative teams with an eye towards mentorship and emotional health. With the right approach, Jen explains the ways sidecar leadership can produce groundbreaking creative work and nurture team members to step into their skills with confidence.

mentioned in this show:

Jennifer Lai Stern

Adam Morgan

Creative Leader and RCL Host

The Stoke Group

Digital Marketing and Full-Service Content Agency

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REAL CREATIVE LEADERSHIP

Season: 5

Episode: 3

Episode Title: SideCar Leadership — with Jennifer Lai Stern

Guest Title:
Jennifer Lai Stern, Head of Brand Studio at PayPal

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Adam Morgan
Absolutely, you don’t need to have more experience in order to lead if what you’re trying to do is ultimately just support them so they can do their craft better. Welcome to Real Creative Leadership, a video podcast produced by The Stoke Group and hosted by me, Adam Morgan.

You know, we talk a lot about different forms of creative leadership on this podcast. And it’s taught me that good leaders have a tendency to customize their style to better suit their team. Today’s guest uses an approach she calls “sidecar leadership.” Being a sidecar leader means leading from a place of empathy and support.Sidecar leaders empower their team members to be the true drivers of their own creative and their own career success, and I think that’s really interesting. We’re digging deeper into this topic with my guest, Jennifer Stern.

Jen is the group creative director for the global brand team at PayPal. Jen has experience at agencies and in-house brand teams leading art direction and creating multimedia campaigns for eBay, PlayStation, and many more. Welcome, Jen.

Jen Lai Stern
Thank you. I’m so excited to be here.

Adam Morgan
Excellent. Well, you know, what we like to do in the show is before we get into this topic of sidecar leadership, I would love you just to give a brief explanation of who you are and let the audience get to know you better a little bit about where you come from and your personal career and relationship with creative leadership.

Jen Lai Stern
Yes. Currently, I am the background head of brand studio at PayPa, and that is essentially leading the internal in-house creative team, focusing on everything related to our PayPal brands. And PayPal is actually my first in house role. I, previous to PayPal, had spent 15 years on the agency side. So, I, my career is split across New York, LA and SF, mostly medium to large agencies. And I’m—I grew up on the art direction side, so junior art director to art director to ACD, that whole journey. And here I am.

Adam Morgan
Awesome. Well, we’re excited to have you here. I mean, the next thing I’d love to just talk a little bit more about is, you know, what kind of work really gets you excited, and then what’s your perspective on creative leadership? Like, what’s your relationship with that?

Jen Lai Stern
Yeah. Work that really gets me excited is something that makes me feel something. So whether I laugh or I’m crying, I think that’s, like, a great benchmark for whether something is good creatively. It’s like, make, stirring up feelings in you essentially. So that could be anger. It could be polar, you know, it could be, “Ah, dang, I wish I thought of that.” But if it’s— if you’re just watching it and moving on with your life, it probably isn’t hitting that note that is going to stick with you. So, it can be really anything. But that’s what I find is like good creative.

Adam Morgan
Oh, I love that. I—it makes me think back when I started in this industry; it was like early nineties and it was just reading ads and seeing spots, and just feeling something and I just like, “Oh, I just wanna recreate stuff like that. I just wanna make stuff like that.” Yes. That makes totally something. So that’s awesome. What about creative leadership? What are your thoughts on creative leadership?

Jen Lai Stern
Creative leadership is, I feel, like, a new topic and I love your podcast because I feel like this is a resource I could have used years ago, but I think, like, people are just starting to realize like creative leadership is — it’s a little bit of a different form of leadership and there aren’t necessarily like ways to grow into it. A lot of it is learned. Like, you become a creative leader and then you’ve got to figure it out, right? You sort of have baby steps to get you there, but a lot of it is through observation and trial and error and figuring out what’s working for you, getting feedback. So for me, it’s been a journey of, like even being self aware of that I wanted to improve on the side of being a creative leader. It’s not just like, you work so hard to do good creative and then when you become a leader — it’s not about the creative anymore. I mean, part of it is, but like, it’s like, how do you get good creative out of other people? And you’re not the one doing it or responsible for it.

Adam Morgan
That’s the reason why I started this whole podcast, you know, five years ago, and I’m like, “Yikes!” Like we just, we get into these roles and there’s no user manual. You think about like in normal business, they have MBAs or other university level, you know, opportunities to grow and learn. And it’s like, no, we’re just all thrown in it. And you combine that with the problem of a lot of creatives like to just stay in their creative cave and they don’t want to move out. And so it’s all about the work. And then we make this leap and suddenly we’re like, “What the filth? How am I going to like, try and guide people or scale teams or do all these other crazy things?”

So yes, a hundred percent. That is the absolute truth. The more we shout this from the rooftops, the more, you know, creatives learn a little bit more.

Jen Lai Stern
Yeah. Yeah, I feel like a lot of people creatively, even now you have to be actively seeking ways to improve your creative leadership. It’s like you said, there’s no MBA. There’s not, like, resources. You have to go out there and find them and you have to go find what it is that you, you know, find books, you know, join panels, like talk to people. So it’s still like a new land people are navigating, I think.

Adam Morgan
Oh, absolutely. And I think the crazy thing about it is we’re, we were, we’re taught so much to focus on the work that you’re right: we don’t think about the leadership part until, you know, we’re in the middle of it. But what I’ve noticed is like, you know, a lot of creatives will still go out there and look at all the websites of like, what’s the cool design? What are the trends? What are the things like you really immerse your brain in, in those experiences, but we need to do more about the leadership part. So I’m curious to find out, are the things that you’ve done in terms of leadership, like what books, what courses, what insights — like,
that’s the stuff that would really help others get better at their creative leadership.

Jen Lai Stern
Yeah. For me, a lot of the creative leadership that I’ve sought out has actually been a lot of observation. I’m a quiet creative, I would say. So a lot of it is being in the room and observing good leaders, but a lot of it is observing bad leaders. And so that is actually helpful. That’s like, sort of my guidepost of like I – not everyone, but a lot of people — have had bad creative directors or like, you always have that story of, “Geez, there was that person I worked for years ago. You won’t believe, but this happened,” or, you know, or You will believe because everyone has that story. But you keep that in your head. And like, that is like something you can, you can sort of note of, like, “I don’t want to be like that. How can I make sure that I’m not doing that? What is it that I didn’t like about that?”

And then I finding books and just finding sort of resources online, whether it’s like, public speaking opportunities or just sort of, but mine is more of an organic observation, absorption, finding ways to be in the same room and sort of taking that. And if you find a leader that resonates with you, just sort of building a relationship with them.

Adam Morgan
I think your experience is pretty common. I think that’s exactly what mine was until I just really started making, like you said earlier, like, making it a conscious effort to really focus on, “I’m in this position. I need to do more about it. I need to actually read more or study more or observe more or do other things to get a better education around it rather than just kind of winging it as we go.”

But yeah, whatever your style is, you can probably find a way to improve on it.

Jen Lai Stern
Yeah, that’s pretty true. There is no curriculum unless you create it and it’s okay. Like, it’s okay if you can take it at your own pace, do your own thing.

Adam Morgan
But anyhow, the reason I wanted to dig into that a little bit, cause we’re going to be talking about this idea of sidecar leadership. And first I want you to tell us more about what that means, but I think that is just one more example of another way of us absorbing leadership styles and leadership skills in order to be better at our jobs as creative leaders. So why don’t you tell us about sidecar leadership?

Jen Lai Stern
Yeah, sidecar leadership is this idea that as a leader, you’re sitting in the sidecar and your creative is driving. And so you are there to sort of come from a place of support and empathy, but you’re really there to help them drive themselves. Essentially, you can help them navigate the right path. You can help problem solve. You can just be there for emotional support, but the idea is that you’re not driving. And so when I came across this, it really resonated with me because it was like someone had articulated what my style was and I didn’t realize, “Oh, that’s me.”

And actually it was really affirming that — that’s okay, that is actually a leadership style. And it isn’t maybe what you would typically think of a leader, how a leader would act. So it actually was affirming to me that that is actually a positive way to lead. And so I kind of leaned into that because I was like, “Well, if, if it works and it’s resonating and that’s what, how I feel comfortable leading, I’m going to keep doing that.”

Adam Morgan
No, that’s awesome. Cause I think the perception is we have to come at this thing in a very strong and heavy-handed way to drive people and better creatives. I mean, I know for me, like we started, you know, I talked about before, like growing up in the, in the nineties in this industry, there were a lot of really brash leaders who were a little more domineering than it is now. I think we’ve learned this whole idea of better empathy and better, you know, leading from the side, but you know, back then there were just a lot of bad examples of just driving it home. So I love this idea that it doesn’t mean that you’re a weaker leader. It doesn’t mean that you’re an unengaged leader. It’s just a — it’s just a different style.

Jen Lai Stern
Absolutely. I had leaders coming up in this industry that were incredibly intimidating and domineering and steering conversation. And that’s almost what you thought you needed to be to get to this level. And then you realize that like things are changing and that isn’t actually, that didn’t always foster good creative. It might have, but a lot of those folks, like, burnt out or they left the industry. Notnecessarily leaders, but the people under them, right?

Adam Morgan
Yeah, their teams.

Jen Lai Stern
Yeah, their teams. So that’s, you know, like I was saying, yeah. You can have that in your sort of core memories of like, “That didn’t work for me as a creative to have that leadership. And so I want to make sure I’m not doing that.” And it’s almost for me, as I’ve thought about this idea, I think there’s probably a tendency as well as for the leader to think, “Am I really doing enough? Am I doing all the right things? Am I really guiding and leading? Because I’m not doing that heavy handed direction.”

And part of, as I think about it — cause I’m in a similar role to you of leading, you know, a big creative team at an in-house company. But part of me thinks like, “No, like, my job isn’t to drive every little aspect. It’s really to come up with the big vision of where we want to go and slowly turn the ship and be there.” Yeah. Like in the sidecar of the ship, just helping it get there, but, but not directing every little teeny thing. So I think that’s really important to think about for ourselves, that we don’t have to feel like we have the imposter syndrome that we’re not leading. We really are, but it’s just a different one.

Adam Morgan
Oh, absolutely. And like so much of this, the reason it resonated with me is I carried so much imposter syndrome as a leader. And it was so great to hear like, that’s — I actually had a leadership style. I just didn’t know what it was. And it’s like a great leadership style for somebody who’s carrying that because like, if you are just supporting, you’re still leading. So tell us maybe some other, maybe some specific examples or processes of how you can lead with this style. What are some detailed examples?

Jen Lai Stern
Yeah, I think a lot of this sidecar leading from with support, a lot of it comes from, like, building trust with your team. Lik, you first you want them to trust you enough to, like, have you in the sidecar with them, right? It’s like the two of you are gonna set down this path of, like, solving this problem or something. You want them to feel that trust already that you are gonna guide them in the right direction, you’re gonna be there for them. And so just establishing trust amongst your team by little things — like, you’re not going to hop all over the best projects, right? You’re like, you’re checking in with them. You’re checking in with their creative health and you know, all of everyone’s success is like the team success. We’re not going for individual success and like, really just establishing that trust and then letting them know that like, you are out there to help them, sort of. I think a lot of it is like, also, you’re willing to roll up your sleeves. If you see them drowning in something, you’re not gonna be like, “That’s not for me to do,” or, I don’t do that, you know? It’s like, I equate it with, like, back in the agency day, like, I’m gonna change the toner and the copier because none of us can print our decks out. Like, I’m not gonna, you know, if that’s an obstacle, like, I have no problem removing that and just showing them that, like, you’re willing to do whatever it takes to get them to where they need to go.

So once you’ve established that, I think they’re more willing to have you there and like, come to you with problems and, or not under like, not understanding, like, “What is the point? Why are we doing this?” Sometimes like projects, they seem like, “What is the point of this? Why are we doing this? This isn’t creatively fulfilling. This seems stupid.” And then if you paint a bigger picture of like, the business and what this will mean for our stakeholders, you know, you kind of help them understand why it’s important to still, you know, come up with the best creative output or the best creative solution. I think that that all feeds into just being their support so that they can do the best job knowing the bigger picture.

Adam Morgan
Yeah, that’s nice. I like that. So here’s another idea that we were talking about is, all right. So if you are in this role of sidecar leadership, the people on your team, they may have more experience than you, right? Like they, it’s not about the old days, or it’s like you have to be the alpha and you have to have all the best experience and be the leader of the pack and be at the top of the heap. How does that work with this style? Can you still be an effective leader with people who are more talented?

Jen Lai Stern
Yeah, absolutely. And like, that is kind of one of the best parts of this leadership style is just letting everyone feel like their craft, like, and their, like, specialty is not what you’re fine-tuning or leading. It’s you. And they always say, “Surround yourself with smarter people,” right? And this is absolutely one of those things on my team. I have creatives and production. So I have, like, photography editors, motion graphics. I am not going to say like in After Effects, I would do X, Y, and Z. Not my place. I’m not going to pretend that I know, like, how to take this photo better than you. But what I can do is help you like, see the bigger picture of like, why is this product launch? What is it about this product? That’s really important for the business. What are the business drivers? Like, what can I do to help you like, hit that creative clarity that you need? Or — and it can be in a number of things — but you don’t need to have more experience in order to lead if what you’re trying to do is ultimately just support them so they can do their craft better.

I think, I think that’s why I love sidecar leadership. It’s like, “I’m not pretending that I know what you like, what it is that you do. I absolutely know that you’re, you can do it better than I could.” And I make that very clear.

Adam Morgan
Yeah, that’s great. It’s also leads into this idea of it’s not just diversity of experience, but there are a lot of other ways that diversity and inclusion can play into this, right?

Jen Lai Stern
Yeah, totally. If we talk about diversity and inclusion, you know, there’s, there’s other — there’s so many ways to support somebody on your team and coming from that aspect of — potentially if, like, English is the second language, you know, maybe the support they need isn’t necessarily creative, right? It’s confidence in presenting work. And so just knowing what form of support your team needs and sort of understanding what they need from you and how you can help them is totally applicable.

Adam Morgan
Yeah. It’s almost like, with this kind of style, we’re not — what’s the right thing? Like, we’re not so heavy-handed that we’re taking away their choices and their personal growth. And at least in my experience in the past, it was like someone would come to you and say, “Hey, tell me exactly what I need to do. Tell me what I need to do to grow.” And in this instance, we’re saying, “You know what? You’re kind of on your own a little bit. Like, I want you to figure out on your own too. I don’t — I’m not going to tell you everything to do.”

And so it really does put some of the burden back on the team member to figure out their own career. And you’ll be there as a guide. You’ll be the helpful help as they go, but they’re really driving and they’re going to drive that career path, which is sometimes a little scary.

I know, you know, younger people on my team, if I, if I’ve ever told them that, like, you know what, I’m not, I’m not going to like put you in every single position that you need to be in to grow, but I’m going to be there to help you when you’re ready for it. So there really is a nice give and take. I feel like it’s not this sort of thing where you just do what you’re told and stay in line, so there’s more freedom, but with that freedom comes responsibility that they also have to take some ownership and push things along and be the expert in photography and be the expert in After Effects, you know, rather than me coming and telling them, click here, move this and do that thing, right?

Jen Lai Stern
Yeah, absolutely. It’s like, they’re driving, right? And so you’re just basically saying, like, or helping, affirming, that, yeah, I think that sounds right. The way you’re coming about, like, that problem or there’s two potential paths you can go down, like, just assuring them that like yeah, that sounds good, or maybe I have no idea, but I’ll I support you and I’ll go down that path with you and we’ll just, you know, do the best we can. But it’s not for you to like, be there to fix every problem or to give suggestions along the way. It’s just so you’re there for them when they need it. And if they don’t need it, great. You’re just there to cheer them on.

Adam Morgan
You also have to show a little vulnerability. I think you have to like, be completely open saying, “I’m not going to come down with an iron fist.’ And maybe sometimes, “I just don’t know. I don’t know what the right thing is.”

Jen Lai Stern
Yeah, I’ll go there with you. And we, if it doesn’t work out, we’re both — we’ll figure it out together, right? I’m there. I’m not going to leave you hanging. I guided you down this path, or like I supported it, so I’m not going to leave you at the end of the path. I’m going to go down it with you, and if it doesn’t work out, we’ll figure it out together.”

Adam Morgan
I’ll tell you where that’s sometimes scary as a leader. It’s just, like, I may have a specific style in my head and I’m all ready to just keep driving that style and, and sure I could, I could direct the whole team to follow that style, but as a leader, you have to kind of give up a little bit of that ownership and be vulnerable and be like, ah, maybe they’re trying something new.

Maybe this old retro seventies style is coming back and I just didn’t know it. And I guess I’ll give it a chance. Like, it’s a little scary sometimes. You’re like, where’s that balance of just telling them the direction or just being open to letting them drive? Yeah.

Jen Lai Stern
I mean, that happens all the time in creative, right? They’re really attached to certain direction and they’re so excited about it. And you’re like, okay, you’re excited about it. So I want to be excited too, but I potentially would maybe have not approached it that way. But the great thing about creative is like, we’re always exploring multiple ways in, right?

So you have your — the way that you’re really excited about, but it would — it’s always nice to show, like, options to sort of back up why you think this one is great. And so you could always add in like, you know, what would happen if it was like a different way and like, let’s see how that compares against like the one you’re really excited about.

And so, you know, there’s — but again, you want them to drive and lead, like, the passion for selling in that creative is has to be authentic. Right? And so if they’re really excited about that, they’re going to go for it. And then you’ll — and half the time you learn from them of like, “Oh, that was rad. I’m glad that I let you go down that path because the passion is what’s going to take it to the next level.”

Adam Morgan
All right. Well, this sounds like the picturesque leadership style. Why wouldn’t everyone do it this way? It’s the next question. Like, are there downsides to this style? What do we need to watch out for?

Jen Lai Stern
Yes, there’s downsides to every leadership style. And I think there are some pitfalls in this style, and I would say that someone who is supportive and has a lot of empathy, you tend to absorb everyone’s feelings and burdens, so you have to be really conscious that you’re now not carrying the weight of all of your teams.

So it’s sort of like — I wouldn’t say emotional baggage, but you’re there for them. You’re hearing all their struggles and their problems. And like, you have to be sort of conscious of not shouldering all of that, like absorbing all of that. And just having a bigger picture of like, they’re, they’re okay. Like they’re, they’re driving, they’re all driving their own paths and you’re there, but you can’t like hold all of that in.

Adam Morgan
Yeah. One of the things I also struggle with is when you’re carrying so much and you just see all the potential and you’re like, you’re driving, you’re getting there, there may be sometimes that a team member doesn’t fit on the team or they’re just not, you know, keeping up.

And so it’s, it’s a lot harder to be more militant about switching them out or firing them or doing anything else, you know, more radical because you just have this hope that you’re like, you can get there, you can get there. So tell me more about that, that challenge of like, how do we balance that?

Jen Lai Stern
Oh, yeah. I mean, yes, absolutely. Sometimes, like, being so supportive and it can actually, depending on the creative, like you don’t want codependency, right? Where they feel like they need you to affirm every step of the way. So there is a little bit of that, like when to lean in, when to lean back, but you’re right. There’s creatives. A lot of it comes down to hiring a team that is sort of the same creative style and mindset. A lot of times it’s not necessarily a hire you made, but they’re, they end up on your team. Right? And the chemistry of that is not something you would have like formulated, but it’s something you need to sort of figure out.

And I think there, I mean, there’s, you have to adapt, you know, maybe it’s less supportive and a little bit more of like giving them space to speak and just adapting like the level of support you’re giving and the — just reading the room really, of like, what it is they need from you. But then again, if it’s like a struggling creative and there, it’s just not resonating, I don’t know. There’s only so much like — there’s consequences, obviously.

Adam Morgan
Not everyone gets a trophy all the time. That’s fair. All right. Well, let’s say people are sold. They’re like,” Yay, I love this style. Tell me more.” Where can they learn more about this type of leadership? Do you have any ideas?

Jen Lai Stern
So I read a great book. It’s called Leaders Eat Last. And like, it’s — I feel like there’s a lot of leadership materials on just, like, coming from a place of support and empathy now. And so that’s a great one. And I think just knowing if that style resonates with you, that there’s materials that you can sort of lean into and seek out just knowing that you’re coming from a place of support. I don’t, now that I say that, I’m like, what are the other types of leadership if they’re not coming from support and empathy?

Adam Morgan
I guess it’s iron fist — there’s iron fist or it’s super dominant or micromanaging or, you know, with even with too much care, I guess it almost comes back to… Well, what’s Kim Scott’s book of like Radical Candor?

There’s kind of those four quadrants, right? Like, you can care too much and go overboard. You can, you know, not care enough and leave me hanging out to dry. You know what I mean? So it’s like, you’re a little more passive. So I guess there’s probably just that perfect fit of the, of the right quadrant there.

Jen Lai Stern
And even if this isn’t, like, your inherent natural leadership style, just adding in a little bit of empathy and support, like sidecar, just like the idea of it entering your space, I think, is really important.

Adam Morgan
Yeah, that’s awesome. Well, this has been such a wonderful conversation. I want just as we get close to the end here, now, what do you have any advice for someone who’s new to creative leadership? How can they get better at adopting the style of empathy and caring?

Jen Lai Stern
Yeah. As a new leader, I wish someone had told me, “Come from a place of humility and just be really transparent. You’re a new leader. You are figuring it out alongside of them. You don’t have all the answers. And if you are just self aware enough in that space that you’re, you’re going to leave, learn, you’re going to grow into this position.” I think that’s really good to go into leadership with. You can’t be an amazing leader, like, on day one, it doesn’t — like you need the experience. You need the fails. You need,sort of, the feedback loops. You need to have good creatives and bad experiences, elite leadership — like, that all just helps feed into you becoming a well rounded leader.

What else? Humility. I think being approachable and just giving your team space to build that trust with you. They, it’s really hard to build trust if you’re not giving them your time, having one-on-ones and like, safe spaces come to you with showing creative that they’re nervous about, talking to you about their career growth. Even just something personal happening in their life. Like, if you don’t give them that one-on-one face time, it’s really hard to build that trust if they’re not getting that from you.

Adam Morgan
Yeah. I love it. Well, this is so great. Thank you so much. Thank you, Jennifer, for joining us today.

Jen Lai Stern
This has been a great discussion. This has been so fun. And I love, I mean, also I didn’t say this, but I think like anyone interested in creative leadership, like your podcast goes so deep. There’s so many topics, so many leaders that have come through. So I’m still going through half. I haven’t finished them. So I’m still going through the library.

Adam Morgan
Good, good. Well, that’s, that’s the hope, right? We’re building some sort of a community where we’re going to share all this stuff with everyone, because you’re right. There’s no manual out there. There’s no, you know, college course. So we’re just kind of collecting all the bits and pieces and bringing it together.

Jen Lai Stern
We’ll build our own curriculum.

Adam Morgan
Yeah, there we go. All right, well, good. Well, how about, how can people follow you if they want to, you know, see where you’re at with your career or things that you’re doing — what are the channels that you’re on?

Jen Lai Stern
I think career wise, industry wise, the best way to reach me is through LinkedIn and I love connecting. So happy to connect with anyone that would love just to connect creatively, but, you know, talk about leadership in general. And I’m on Instagram at @jenlaistern, if anyone wants to follow, but that’s a lot of non-industry talk. But if you want to see my kids and my travels, then you can follow me.

Adam Morgan
Good. Make you more human. That’s the thing. It’s all, it’s all about AI. And so we need to be more human in contrast to all that AI today. So yeah, kids and travel is awesome. Yeah. Well, thanks again for joining us. This has been an awesome episode. Thanks so much. All right. We’ll see you later.

As always, you can find me at adamwmorgan. com. And finally, this show is produced by The Stoke Group, a full service digital agency that specializes in content, marketing, video, and interactive experiences. So if you’re looking for a partner for strategy or content or anything else, visit thestokegroup.com. Thanks again for listening and we’ll see you next time.