17 – Design leadership lessons from bicycling (ft. Sally Carson)

In which Peter and Jesse talk to Sally Carson, Head of Product Design at Duo Security (now part of Cisco), about her journey, from bike messenger to multimedia designer to design lead. Along the way, we discuss executive relationships, handling burnout and managing your energy, and how her experience cycling prepared her for the ups and downs of leadership.


Cold Open

Sally: Reflecting on it now, I learned so much about my relationship with anger and it really helped me. You know, cause people are trying to kill you.


Peter:  I’m Peter Merholz.

Jesse: And I’m Jesse James Garrett,

Both: And we’re Finding Our Way,

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

Jesse: On today’s show, design leader Sally Carson of Duo Security joins us to talk about her path to design leadership, growing a design team inside a fast scaling startup, managing your boss, managing burnout, and a whole lot more.

Sally: So I currently lead product design and user research for Duo Security, and Cisco acquired Duo about two years ago now. So I’m now part of Cisco. Yeah.

Peter: And how long have you been at Duo?

Sally: I joined Duo five and a half years ago. Dug Song, the CEO, hired me to build out product design from scratch. They had one user experience designer at that time. But I renamed it to product design at that time, very deliberately…

Peter: From user experience?

Sally: From user experience, yeah. Part of my rationale, why I renamed user experience to product design was to recast it internally within the company, because the engineers and the product managers did have some familiarity with working with the one user experience designer. And I was coming in with a different approach and I wanted to say this isn’t the way that you’ve been operating. This is a different thing, different flavor.

Peter: What was your different approach? How did your approach differ from what they were doing?

Sally: One fundamental difference. I was just able to get resources and budget to actually staff up because I think by the time I joined, it was one designer for maybe 30 engineers and just, you know, that ratio really limits what you’re able to do. I also was intent on bringing in a user research competency and building that out.

So any expectations that had been set in the prior years about how they had operated with the single user experience designer, I wanted to make it clear to everyone that this was going to be a different way of operating, in part, just because we were going to have healthier ratios to start with. So that really changes the type of work that you’re able to engage in.

Peter: So you really wanted just a clean break from the before time to your leadership time.

Sally: Yeah. I’ve found that in general, it’s some of the most challenging work that we do. And we’re talking about driving cultural change. I find it’s easier if you’re working with someone who has no sense of what it means to work with design. It’s almost more difficult if you have someone that has a really strong preconception. They’re like, “I understand exactly what this is,” but their conception of it is different from what you’d like it to be.

Jesse: Enough knowledge to be dangerous, right.

Sally: Yeah. I’ve been interested in, sometimes you all mentioned, change management as opposed to transformation and that nuance, if I remember it’s like the way you defined it, Peter, change management is more like the end state is known and it’s just the process of getting there. Whereas transformation, the end state may not be as well understood. Is that it?

Peter: Right. Exactly. And well, has that been your experience with Duo? Like, were you continually transforming into states that people weren’t quite sure where you were headed?

Sally: It was definitely transformative. There’s an improvisational aspect to it where I sort of had a vision of what we wanted to get to, but the way that I staged it progressively, it did take some, just adapting to the environment at the time, because we were also going through hypergrowth.

So the context was changing. At least every six months, it was a different company.

Peter: Was that a vision that you established when you joined, when it was just you and that one other designer?

Sally: What I came in with was a hodgepodge of what I had seen as best practices throughout my career. Like I think at that point, I would have been about 15 years into my career. And so I had seen one particular shop had done agile really well, and had found a way to integrate design fairly well into agile.

A different shop had healthy ratios, a different shop had really strong research. So I was trying to pluck from the best that I’d experienced and put it together and basically create the design team that I always wanted to work within.

Peter: Had you primarily been in startups up to that point, what was the nature of your background before joining?

Sally: So let’s see. I’m an army brat. I moved all around. Eventually we settled in Virginia and I did go to college. I got a BFA in communication, arts and design at Virginia Commonwealth University in Richmond.

Peter: So you’re a graphic designer.

Sally: Yeah, I got graphic design training. It was really a mixed bag of video, animation, illustration, graphic design, and then amazing faculty that had us reading, you know, Marshall McLuhan and Noam Chomsky, which for my 19-year-old brain was probably mostly over my head. But as I reflect back, it’s come in handy quite a lot, you know, just to make sense of, like, the changing media landscape, for example.

Jesse: How did you find your way into digital?

Sally: So I would have been at VCU in the mid-to-late nineties and there was no web component to my schooling, but I was interested in the web and yeah, I just started doing what a lot of folks at that time did, which was just view source, copy, start hacking it, and figure out FTP.

And then I got really lucky because my first job out of school was a small, educational startup In Charlottesville. And they hired me as a full time illustrator, which is pretty extraordinary. But then when I joined, they found out I knew how to code. And they were like, “Oh, you’re upgraded to multimedia developer.” 

I’m really fortunate where I have this career arc, where if you trace my job titles through the years, it’s a complete parallel to what was happening at large within the industry. Like, I was a multimedia developer. I later was a web designer, interaction designer, user experience designer, product designer, like that is how we all do about our titles through the years.

Peter: Sadly those, Radford surveys that everyone has to use, in order to base industry compensation on, still refer to us as, like, web designers. Cause they’re like way out of date.

Sally: Gosh, yeah, come on, Radford. Get it together.

Jesse: Hey, taxonomy. It’s hard.

Sally: It is. Yeah.

Peter: So, how do you go from being a multimedia developer to a design leader?

Sally: I had plans to move up to New York in the summer of 2001. I rented an apartment up there. And I, found a Polish cyber cafe, and they had satellite internet and that was the only high speed in Greenpoint at the time.

And I bartered with them to get high-speed satellite internet on the roof of my Greenpoint apartment building, by redesigning their website.

Peter: Nice.

Sally: And I worked it out with my boss at the time. That startup in Charlottesville, I was like, I have high speed internet up in New York. Let me keep working remotely. And so I moved up. I lost my job within, I don’t know, three or six months.

They were just like, this remote thing is odd and it’s not really working out. And I was like, okay, that’s fair enough. And then there were no jobs. In New York City in particular, there are no jobs. I was unqualified to wait tables, to, you know, be an assistant, to do any kind of administrative work anywhere.

At the time in New York City, the job ads for anything web-related were like secretary / webmaster. Isn’t that so odd where they’re like, this is just pure administrative work and yeah, I couldn’t…

Jesse: And also, can you configure IIS for us…

Sally: Yeah. Yeah.

Peter: How well can you navigate the shell?

Sally: Yeah, very poorly. 

So I became a bike messenger and did that right after 9/11 in New York for about a year.

It was such an amazing job and it’s such an amazing time to have that work, to get to see every secret pocket of the city that most people don’t have access to.

It was just an adventure. 

Reflecting on it now, I learned so much about my relationship with anger and it really helped me, you know, ‘cause people are trying to kill you when you’re a bike messenger in New York. Like the taxis hate you there. They are trying to kill you. People are doing dumb things that are dangerous. They’re doing scary things that are dangerous, on purpose. And I just learned how much, the more I would engage and get angry and feed into it, it would build my anger, but if I could just let it go and let it wash over me, and not replay the bad incidents in my mind over and over, just really changed my relationship with how I can deal with difficult people or difficult moments, that was helpful for life and for my career.

Peter: For becoming a manager.

Sally: It’s not like I’m fully enlightened. I do notice now, if I’m replaying a situation that made me angry, it just feeds into it. It makes me more upset. You know, I carry that bad emotion with me. It drains me.

Peter: Right. Right. So you’re a bike messenger. At some point you must get back into design and into design leadership.

Sally: Yeah. I was doing a lot of bartering to get things that I needed, still doing design work. And then, the grand finale of my bike messenger career, I did a East Coast bike trip with two friends of mine, two girls from Virginia. 

We were raising money for cancer research. And the three of us rode our bikes from the border of Canada to Miami in three weeks. 

Jesse: Wow. 

Sally: It was too, it was too much, it was too hard, it was nearly a century, which is a hundred miles, every day for three weeks straight. And the first day of that trip was my first century I ever did. Yeah. 

That trip just taught me, How do you do a hundred miles? You really do it a mile at a time. You know, you’re like, okay, five more miles. And then five more miles. And then five more miles you’re just chopping it up into these little bits.

Thanks for indulging me on all the bike stuff. 

Jesse: Well, I think that bike stuff is relevant, honestly, because I hear a lot of  preparation for leadership there in your various travails on two wheels, whether it’s, shaking off the moment-to-moment bad feelings of contending with aggressive drivers in New York City, or just getting up every day and facing another hundred miles on that long ride. Those are lessons in resilience, honestly, that I think are essential for any leader to learn if they’re going to be successful.

Sally: That’s great. Yeah, it certainly gave me confidence.

As we went through the Virginia portion of that ride, some pals of ours rode that leg with us. And this one guy, Ed, was working at a company called Crutchfield at the time in Charlottesville. And I was just chatting with him, riding next to him. And he’s like, you know, we’re hiring a web designer. So call me up when you get back from this trip. 

So then I became a web designer. Crutchfield is an eCommerce shop and they sell high-end audio and video equipment. And I joined right as they were transitioning away from a print catalog business into an eCommerce business.

We were borrowing a lot of ideas around qual and quant from what Amazon is doing at the time. So we were doing funnel analysis, AB testing, tracking conversion metrics.

So that was great for just learning chops around quant informing product decisions. And then we also partnered it with qual. 

Music break 1

Peter: You mentioned, when you joined Duo, the ratios were out of whack. There was one designer for 30 engineers. So I’m guessing early on, you knew you needed to recruit and hire and build out a team.

That was five and a half years ago?

Sally: Yeah.

Peter: I’m wondering if there are stages of your job, stages of your team, how you evolved, how things evolved around you.

Sally: Definitely. But early on, we just needed to grow and we needed to build a team pretty quickly. And I had joined Duo at… I was four months pregnant with my first and only kiddo, so there was also an external deadline, you know, I needed to build up a little nucleus of a team quickly.

Peter: Five months before you were going to be gone for a while.

Sally: Yeah. Yeah. So I was able to make some hires and got a couple of product designers in, got a user researcher in. And really what I wanted to emphasize with the org was the power of user research. And to quickly try to get us to a place where we’re getting beyond strictly usability testing.

Peter: What was the opportunity for user research? What did you witness that was lacking that you felt user research could address?

Sally: Happily Duo was already so customer centric, they really were, so the stage was set in a really great way for me. Because when we’d bring engineers and product managers to observe the usability testing, it, like, pained them to hear the customer struggling and to watch the customer struggling, which was great.

You know, I didn’t have a team that was dismissive of that kind of feedback. 

Peter: I’m curious how you framed the advocacy for user research. I think we’re seeing that it’s easy to build out design orgs because more designers means more assets. The value of user research is less clear, I think, for these organizations, because they’re not making anything, they’re not producing material…

Jesse: It’s less quantifiable at least… 

Peter: Yeah. And so how were you able to advocate for user research and going beyond the expected usability, into stuff that’s more generative? What were the stories that you found that worked? What were stories that maybe you tried that didn’t work?

Sally: One thing that’s been really beneficial for us is to come and present short consumable research nuggets at all-hands meetings. What I really wanted to get away from was, user research goes off for six weeks and comes back with a 30 page PDF.

It’s very participatory. So I think that’s a high level theme. How can we make design and research as participatory as possible, and really bring people along for the ride, co-create together so that they’re truly invested in it. What that might look like for those early days of usability testing are bringing those engineers and product managers into the room and having glass on one side of the lab.

In a hallway where people are walking by, including our cofounders, so that they can see what’s happening in there, generates a lot of interest.

Jesse: So kind of raising the literal physical visibility of the work. By not having it take place off site or in a sealed off soundproofed room that nobody even knows what’s going on behind that door.

Sally: That’s right. Yep., really exposing it. And then, because we’re bringing them along for the ride, getting them excited about it as a unique differentiator for us. Like, I’m not aware of other cybersecurity companies that have this rich investment in design research. So it becomes a point of pride.

Peter: So you mentioned the CEO’s name… was it Dug? I’m curious to hear more about your relationship with him.

If you’ve listened to some of our past episodes, we talk a lot about relationships and in particular for leaders in the position you’re in, there’s a lot of need to manage up and get, maybe not just Dug, other executives also understanding what you’re doing and onboard.

How have you approached that?

Sally: I had done my own internet of things hardware startup prior to joining Duo, for about three years. And he was an advisor and a mentor to me as a first time founder. So I was learning from him directly through him mentoring me, but also just the modeling, watching how he was running Duo as a super successful startup and doing it in a way that’s so humane and customer-centric and people-centric for the employees. So that was wonderful because coming in,  already having had a foundation with the CEO and a relationship there.  

Chester’s my boss, and he leads engineering. And between Dug and Chester, they both are so sympathetic to what design can do, and the value of investing there. It was so helpful for me. It really set the stage where I didn’t have to work, upstream or fight gravity. You know, I was finally in company where generally they understood the value and they understood why I was there.

I had enough credibility that they trusted me to give them things that they didn’t ask for and to show them why that was valuable.

Jesse: How did you earn that credibility?

Sally: I think in part, having had that relationship with Dug prior to working together. But then, you still have to prove it out in your new organization, even if you have the relationships. It’s so key to deliver some quick wins, even if they’re small in scope compared to what you can ultimately deliver. 

And if they’re resonating with your audience, whether that’s executive stakeholders or someone else within the org, really socialize the crap out of those small wins, you’re trying to build out an early portfolio of case studies where you’re delivering value to the business that’s concrete, that’s credible, that’s resonating.

Jesse: Right, right. What is the role of risk-taking for a new design leader in an organization? Because I’m imagining a leader setting out to go get those quick wins. It can be very easy to choose the safest, least disruptive things to do. So how did taking a chance play into your path at Duo?

Sally: Maybe speaking about cycling relates to this. And before cycling, I was a skateboarder, and in the past I’ve been a bit of an adrenaline junkie. 

Peter: Not anymore. 

Sally: Not anymore. I don’t know. There’s so much adrenaline hammering me from the outside world right now that I’m like, I just want peace.

I just want calm.

Jesse: We’re all on a mountain bike right now.

Sally: Totally. Totally. So risk was a big part of it. That’s kinda been, my M.O. is just take huge swings. I can’t imagine being successful in this role without having a big appetite for risk.

Peter: What were some of the risks that you took?

Sally: I had not gotten formal training on being a good leader, a good manager. I hadn’t had any block-and-tackling on that. And I was building out a big team. So for me, there was a lot of learning along the way, just on the basics of being a strong leader, being a good manager, and kudos again to Chester because he has done such an incredible job of building out what he and I sometimes called a “leadership factory.” When you’re in hyper-growth, you have to develop successive waves of leaders, your top talent, ICs that are interested in the management track. How are you going to develop them into managers in 18 months? And. Who are the next wave of directors that could be credible in that role and how can you set them up for success and not extend them beyond what they’re capable of now.

And we all go through the same training when you join as a manager. And, that helps because we have a shared language and understanding. There’s a shorthand when we’re using the same nomenclature, but there’s a really high investment in Duo around professional development. 

I have not encountered an organization better than Duo, that’s better at helping people become first-time managers and then grow their careers from there. It’s very thoughtfully done and we put a lot of investment there ‘cause we want to retain people long-term.

Peter: What, if any, distinction do you make between management and leadership?

Sally: Yup. Oh, this is good, Peter. ‘Cause I feel like you have some thoughts on this if I, if I recall.  And it’s good, ‘cause I think you’ll disagree.

Peter: Well, but I’m wondering because it sounded to me almost like you were using management and leadership interchangeably, and we’ve discussed them as distinct.

Sally: Oh, that’s so good.  I do make a distinction between leadership and management. I think it’s a Venn diagram in my head. There are managers who are not leaders. There are leaders who are not managers, but there are managers who are leaders and, anybody can be a leader in a sense, there are people who are influential over the organization’s culture and they might be individual contributors who don’t have any direct reports, but the way that they carry themselves is either an embodiment of how we all want to show up organizationally, or maybe they’re highly influential over the product or other aspects of the organization. 

There’s a great book that I love called Speaking as a Leader. And I kind of use it as a tuneup every six months. I’ll just listen to like 20 or 30 minutes of it to refresh myself. And it’s so handy because it talks about how, at any given time as a leader, you need to be really clear about what your current talking points are, what you’re saying.  

Being thoughtful about the way you show up and being aware of your audience at any given time. It requires high emotional intelligence, but sort of a different flavor of emotional intelligence. There’s the one-on-one emotional intelligence. There’s also power in reading a room, like the one-to-many kind of emotional intelligence.

Not just being mechanistic and transactional, the way that managers who aren’t leaders can be, but really reading the room, maybe surfacing things that are going unspoken that are too dangerous for individuals to say and using your role power as a leader to go ahead and put voice to things that people who are maybe underrepresented or don’t hold that much power would be putting themselves at risk to say.

It’s easier to train people on management. Are you doing your one-on-ones? Are you building trust with your direct reports? You know, here’s how you delegate work. But it’s a great entry point into leadership at large because management is a little bit more accessible.

It’s a little more like, okay, here’s your checklist. As a first time manager with a few direct reports, make sure you’re doing these things. Just rinse and repeat, rinse and repeat. And you’ll inevitably encounter new challenges, So there’s no real way to practice it without just doing it.

Music break 2

Peter: What are the leadership skills that have been the hardest for you to acquire and learn?

Sally: This is where I get kind of selfish. I’m like, “Ooh, maybe Peter and Jesse can teach me some things here.”

Peter: That’s fine.

Sally: Honestly, it’s been such a joy to be able to hold one position for so many years because there’s things I learned in the course of five and a half years that I wouldn’t possibly have had the opportunity to learn if I had only stayed for two or three years. You know, a product manager might make a key decision on strategy, leave the company. And I get to see how that played out over the next few years. And they didn’t get that learning cycle.

Then I notice how I’m changing, my team is changing, the context is changing right now. 

What’s top of mind for me is energy management. I have days full of meetings and there might be a really important meeting at 3:00 PM where my energy is really flagging. And I’m really just like mentally fatigued because of context switching, so that afternoon slump, if that happens to collide with a really critical meeting, that’s intellectually intense or even emotionally intense, that’s one of my biggest challenges, is just like managing energy. Staying mentally sharp when I need to, right? ‘Cause it’s almost pointless for me to be there if I’m not mentally sharp for some of these conversations. So what do you got for me? You got any advice?

Jesse: Yeah. Well, in general, I think design leader happiness, and day-to-day satisfaction tracks very strongly with the leader’s ability to control their own calendar.

Sally: So true. Yeah.

Jesse: And, to the extent that you are able to create space in your calendar for yourself to give yourself what you need to show up at your highest level of capability, that’s, what’s gonna make you successful.

It’s challenging, though, because in most environments, design leaders don’t have enough authority over their calendar. They are working to rhythms that are set by other departments. 

Peter: I’m a fan of the 20-to-30 minute coffee nap.

Sally: Oh yeah, yeah, yeah, definitely. 

Peter: It seems silly, but if you can take it at the lunch break, if you can give yourself an hour at lunch and you spend that first half hour eating and the second half hour trying to doze, even if you close your eyes and try to ignore stimulus for half an hour and you don’t sleep, you will reset a bit.

Because I’m like you, I’m not great with intellectual energy in the afternoon. I try to do all my intellectual energy in the morning, and then in the afternoon, that’s where I’m doing more kind of administrative stuff. But if I have to do intellectual energy in the afternoon, I will take a nap. If I can get even 20 minutes to try to refill my energy cup, so I can be alert.

You know, I know people who burn out, even when things are fine, ‘cause they just keep working.

There’s a category of person who keeps working, and I think a lot of folks burn themselves out unwittingly, unknowingly. 

That said, burnout is also organizational, contextual, situational, right? Certain contexts lead themselves to burnout. It sounds like Duo is actually not one of those. The prosocial culture you’ve been talking about, I’d be surprised if burnout was a problem, just because of sensitivity that the leadership has had.

Jesse: It sounds like people are really watching out for each other there, which is the big thing that leads to burnout in so many organizations. That there basically isn’t anybody watching to notice that you’re burning yourself out over there.

Sally: That’s right. I’m so lucky the culture is so healthy at Duo and I try to not take it for granted because it has been so long since I’ve been an employee elsewhere. I think Yahoo is really the last place I was an employee and that would have been 2005-6.

You’re making me think of something as you’re talking about burnout. I think I’ve experienced two flavors of burnout. I’ve experienced the one where I’m just simply overworking and maybe something like adrenal fatigue, if that’s a real thing. And some of that for me has been not appreciating my own value. What I mean is I need to over-perform, I need to overdo it, I need to overdeliver because I didn’t have the intrinsic confidence in the value that I’m bringing. And really have worked hard to try to train myself out of that and say, this is what I’m able to give today. And I understand that that’s valuable and that’s why I’m here. That’s why they’ve asked me to be here, yeah.

Jesse: I think that’s a real pitfall, especially for new leaders who are like, “I’m moving into leadership for the first time. I feel like I’ve taken on the mantle of leadership.” Right? And they put all these expectations on themselves about how they now need to show up, that is different from how they were showing up before.

And it’s true. Leadership does have its own set of requirements, but people build that up into this thing, especially that they need to be the hardest-working person on the team by every perceivable measure, in order for them to continue to earn their place at the head of the table, so to speak.

Sally: That’s so true. That’s so true. Really, they’re doing their team a disservice because they need to model to their team taking care of themselves. Taking vacation time, not sending those late night emails. 

Peter: I think a lot of leaders don’t recognize the importance of modeling. They just, they tend to…

Jesse: Do, as I say, not as I do.

Peter: But people do as they do. ‘Cause that’s how we’re programmed.

Jesse: There’s another facet of this that’s related to the culture of leadership and the cultures that leaders establish for their organizations through what they model. You mentioned that you report into an engineering organization. In most contexts, I would say that if I heard from a design leader who was reporting into an engineering organization, I would assume a certain set of cultural difficulties that would come along with thatm of the differences between the way that an engineering organization wants to manage its work and the way that design work wants to be managed, and potentially really conflicting values on the part of a design leader versus an engineering leader in terms of how they make decisions, how they orchestrate the work of their teams, how they communicate.

All of those kinds of things. 

So I wonder what advice you might have for other people who find themselves as design leaders reporting into engineering organizations, for how to manage that relationship effectively. What do you think makes for an effective partnership when design is situated within an engineering culture?

Sally: For me, it really comes down to the leader. So Chester, my boss, has worked with designers before. I feel like on a deep level he groks what I’m here to do. And there’s just so much trust there. 

I’ve learned so much from him talking about modeling and leadership. He’s got such a learner’s mindset. He really listens deeply. He’s open to learning. He will always offer his perspective, but he granted me that autonomy and gave me the space and time that I needed to prove what I was trying to do and to build that credibility. So I think if you’re going to sit within eng, it’s really important to have the right leader as your head of eng. 

Some of the benefits of being in eng, is eng tends to get budget for headcount, so that’s kinda nice. And in the early days, as we were just getting started with my team, we really did want to be in lockstep with eng because they were shipping really frequently. So we wanted to really embed with them, co-create with them. And it was helpful organizationally, so much came for free, was sitting in the same place within the organization, so much communication, there was no silo. 

Then, as we built out research, then the opportunity became, Now, how do you make sure you’re also partnering in a really strong way with product management, as we kind of became more mature, became more strategic. But in those early days, when we were a little bit more delivery/execution focused, sitting within eng, was very helpful. And it hasn’t really been an impediment to us since in large part because of Chester, because of my leader.

Peter: You said you had the autonomy to run your team, as you see fit, regardless of who your leader is.

Sally: That’s right. I’m not expected to run it as though it were an eng team, which is helpful, yeah. So, we were able to demonstrate a different way of working.

Peter: It sounds like when you joined Duo, in terms of things like culture, leadership, you hit a jackpot as a new design leader in an organization where a lot of the challenges that other design leaders face in other organizations just weren’t there.

I’m wondering, though, how, if at all, that changed with the Cisco acquisition. ‘Cause now there’s a whole set of relationships that you didn’t have before, new people that you’re interacting with. How have you had to shift or change how you relate up and out, now that you’re within this much broader context?

Sally: Yeah, I guess the fundamentals are still the same, which is: build relationships, identify who your key partners need to be, and just spend the time to build that trusting partnership. And, I’m happy to say, I haven’t really encountered much in the way of politics at Cisco, which is pretty extraordinary.

‘Cause it’s a huge company. But honestly, like, I’m still learning my way. I’m still finding my way. It’s a massive org and it’s a new set of skills I’m currently developing. How do you seek and gain alignment across a broader organization where you’re not necessarily directing those resources? That’s an interesting pickle.

Peter: So what are some steps that you’re taking to realize that?

Sally: Hm, I think Duo does have a lot of credibility within Cisco. And so using our organization as a model is one. Again, same playbook, build out those case studies and socialize them to demonstrate what we do and credibility, and then really invest in one-on-one relationships with your key partners, just spending time understanding what are their needs, what’s challenging them. That’s been foundational for me. I’m sure if we talk again in a year, I’ll have new stuff.

There is something else on burnout. Can I take us back to burnout for a second? Okay.  ‘Cause I’m again, selfishly, I’m curious to hear what you all have to say. 

Peter: And clearly this is something you’re dealing with. I don’t know why in a pandemic, you would be considering burnout.

Sally: …the smoke-filled air. Yeah. 

Peter: That’s right.

Sally: Yeah, the other flavor of burnout. So there’s the overwork burnout that I’ve certainly experienced at times. And then the other flavor, I suspect particularly as a design leader, is like a creative malaise where part of it is, how do you continue to maintain a creative practice that rejuvenates you so that you can bring your energy and your spirit into leadership? I find that there’s ebbs and flows of feeling lit up creatively, and there’s a form of burnout for me that I encounter sometimes where I’m not particularly inspired. I know I will come out of it because it’s cyclical, but it’s something like a creative malaise and it’s a real bummer when it hits.

And I always know it will resolve itself, but it’s inevitable phase that I have to go through. And it’s always a bummer when it happens. Do you all have that?

Jesse: I think, to your point, I have that less when I have creative work to do, and, as a design leader, your access to creative work is highly variable, and in some cases might be more or less nonexistent for very long stretches of time,  before you ever get to offer a creative opinion, you know, move a thing around on a screen, any of that stuff.

And I think that you touched on something really important, which is that we think of burnout in general in terms of overwork, that if you’re starting to feel burned out, the thing to do is to do less, but, in fact, what it might be is that you’re just not doing the right things, that you’re not doing things that actually fill you up.

That, in fact, what you might need is a little bit less of whatever you’re considering your wind-down time, because it’s not actually replenishing you and you need to go get a hobby.

Sally: Yeah. Yeah. Like I really rely on just taking walks in the middle of the day, so it’s really regenerative for me to take a quick walk outside at least once a day, if not a few times, if I have a little pocket of time. 

Music break 3

Peter: Also following on Jesse’s response, how creative are you in your work these days? You’re running a 30-person organization, product design and research, maybe… do you have content or other functions in your team as well?

Sally: Yeah, we brought in UX writing, UX eng, some design systems, design ops types. 

Peter: Right. So you’ve got a team of 30. And, when I think about people in your role, I think of four sets of activities they’re doing: there’s creative leadership, managerial leadership, operational leadership and I’ve added a fourth. I used to just have those three, I’ve added a fourth, which is this executive leadership, kind of strategic. It’s related to creative, but it’s different, ‘cause you’re setting direction in some ways, or having certain kinds of relationships or conversations. 

And I think a challenge that a lot of design leaders in your position face is, as Jesse pointed out, you’re not doing the creative work, and I’m wondering if that’s been true for you, how you’ve maintained access to the creative work, or if you’ve elected to delegate much of that. When you do do creative work, how do you know where to focus your creative time and your creative energy? What’s your relationship to creativity within your team? ‘Cause I’m sure it’s not what it was when you were two to five people.

Sally: Yeah. Yeah. It’s really different. Now, when we were two to five and maybe up to 15, there would be a Brew:30, Friday afternoons at 4:30. The whole company would get together for happy hour and tap the keg. And it was an extrovert’s dream and all my little tiny baby designers and me who skew more introverted would go hide in our usability testing room and do a quiet drawing hour, where we’d, like, listen to a podcast and not talk, and draw together.

And it was the cutest and it was so fun. And outside there was the hum of people talking to one another and that was kinda nice, like that added to the ambience. But I love that quietly stealing away into our little lab and just drawing quietly together. That was really sweet. 

These days, as you run through those four pillars, flavors, of leadership, the operational, managerial, I’m naturally drawn less to that.

I’m more drawn to the creative and now executive strategy stuff. I have to be really careful though, because with a team of this size, what I don’t want to do is the swoop and poop, where I’m over here doing my executive stuff, and then suddenly I come and mess with people.

You know, people do design reviews with me and I give feedback. And the feedback that I try to give is typically not as much around fit and finish. It’s more around, “Oh, they’re not aware that there’s this whole other thing happening with product over here. But if they were able to find a way to weave that together, we could do more with what they’re working on right now. So let me make sure that they’re aware of that they have the right connections, they’re having the right conversations.” 

It’s sort of like being a cross-pollinator, being a bridge, doing that organizational wayfinding and having the super high-level context for what’s happening and bringing that into the detailed-level design work.

Where I do get involved, I do try to be kind of unapologetically opinionated about anything we design that’s gonna be for the end-user. So we’re a B-to-B company. We sell into the enterprise and we have a couple of key personas and one is like an IT administrator who’s going to deploy and manage Duo, but then he’s going to deploy as a company, and all of his employees have to use Duo as a two-factor authentication device to login to their work. So that’s sort of like the B to B to C in a way, like we are designing for the consumer. We’re selling into the enterprise.

I have a background in consumer web, so I spend a lot of time bringing that consumer web lens to enterprise security, which is kind of cool. And my theory,  my belief, is, if we can make the end-user successful, and make that a really great, super friction-free, experience, the value builds up.

It makes the IT administrator successful. It makes the buyer successful. The Chief Information Security Officer successful. So what we’re trying to do is shape good security behaviors, it’s a gross term, but in the security space, they call it security, hygiene, you know, good, security hygiene make that end user successful.

And that’s where I spend a lot of my attention and time to make sure that’s right.

Peter: That sounds like a conscious choice that you’ve made in terms of where you’re devoting that creative energy.

Sally: Yeah. And part of it is because those people have not opted into Duo. Duo has been foisted upon them, and I’m thinking, too, that your first encounter with Duo might be as a part of onboarding into a brand new job, you know? So you’re so inundated with new stuff when you start a new job, and Duo is one of a couple dozen things that you get introduced to you on your first day of onboarding into a new job. So understanding that as a context, as opposed to the buyer or the IT administrator, who’s done the research, done a little bit of competitive analysis, and has decided to choose Duo to deploy at their company.

So I’m really focused on the person who didn’t opt into this experience and making it great for them.

Peter: You mentioned less interest in the more management and operational aspects of your role. In my experience, those are the things, though, that, you know, keep the engine humming, keep the lights on, and if they’re not attended to, the organization starts kind of falling apart. How have you accommodated your less interest in those functions?

Is that one of those things where you just occasionally suck it up and like, “Okay. Today is my operational day and I’m just gonna kind of power through that.” Or strategies have you adopted to make sure that that’s getting attended to.

Sally: Yeah, I think one is, I’ve just built the self-awareness that those just don’t tend to be things that give me energy. They deplete my energy, but I can do them. And then, finding great leaders and great people who I trust that I can delegate work to who tend to thrive doing that type of work.

Like, that’s the magic is when you find the peanut butter to your jelly, right? Like someone who’s like, “I love doing the ops stuff. That’s my jam. This is what gives me life.” And then it’s a win-win, you know, it’s like every time there’s taxes and I’m like, I can’t believe there’re CPAs and they love doing this.

It’s so great. What a gift to humanity, these people. But yeah, they exist, and finding people who are great, almost like when you hear about CEO/COO partnerships and like the role of the COO is so varied and it’s so much depends on essentially, like, the psychographic profile of the CEO. They need to create a whole greater than the sum of its parts.

Jesse: And this is part of why I always advise leaders to tune into what they need for themselves, rather than trying to model the structure of their leadership on what somebody else created for themselves. Because, you know, your strengths are different. The complements that are going to support you are going to be different. 

So one of the themes I feel like throughout this conversation, has been the need to continue to be flexible in the face of ongoing change. And as we’re winding up here, I am curious about what changes you see around the corner? Is there a process of change that you’re in the middle of right now that you’re looking forward to seeing through?

Sally: Hmm, that’s good. Yeah. I’m in a reflective place right now and I am reflecting quite a lot on… I’m so proud of the work that we’ve done as a team, as a company, I’m really proud of the value that we’re creating in the world. Honestly, it’s such a joy to deeply believe that if more people buy the stuff that we make, the Silicon Valley cliche is, like, “make the world a better place.” 

It really does. We help with election security. We help with critical infrastructure. We help the trains run on time. It’s that part that is so cool. And I’m so proud that a design team can have positive impacts on the safety and trust that people feel when they use the internet. Like that is so cool. 

Earlier this year, before the pandemic set in, I was pushing myself to explore what it means to savor. And that was, like, a new thing for me. I’m feeling proud, I’m still working, I’m not disengaging from the work, but what does it mean to really savor a big accomplishment that I feel proud of? And, now I’m just reflecting forward on, What is the next chapter? I don’t know. It’s neat to talk to you all right now, because I do feel like I’m in a moment of trying to spend time to understand what that could and should mean for me.

Peter: You were referring to some of the societal context that we find ourselves in, and clearly this, this year has been a…

Sally: A Whopper. 

Peter: A difficult one. And I’m wondering how that has interceded into your and your team’s work lives, or do you try to keep a little wall around your team, and there’s work time and not-work time. Like, for eight hours, let’s focus on this and then, and then not, as opposed to, oftentimes, work and non work-life bleed together. How has that manifested within you and your team and how have you approached that?

Sally: I try to be really honest with what I’m struggling with right now, you know, so if I’m having a one-on-one conversation, I try to be really honest about what’s tough right now as an offer of vulnerability. If they feel the need to share, I want to make sure they feel like they can share with me in a way that’s safe.

I don’t want to dump on my team and create more stress for them, but I just want to show up as a real, fully-formed human, and, especially because the lines between personal and work life have blurred, if not completely dissolved for a lot of us, and then also trying to remember to bring some joy back. 

The thing I did yesterday morning was I spent some time over the weekend playing with gouache, and I hadn’t done that in quite awhile. It’s like a more opaque, watercolor-type of paint. So, if you enjoy pushing color around on paper, gouache is a lot of fun, and I’m just playing with it and getting to know it.

And so I just posted that on our team Slack Monday morning, just to remind them, we’re all creative people, and what are you doing to maintain your own creative practice? I try to share a bit of my personal life just to give them permission, if this is something that you would find to be restorative, even in the middle of your workday, giving them permission to do it.

When we’re not having fires, if I step away for a 10-minute walk, I’ll post that to the group Slack and say, “Hey, I just need to take a bit to recharge. And I’m going to go for a little walk.” And it’s not important that they know I’m walking. It’s more about modeling and give them permission to do what they need to do to take care of themselves too.

‘Cause that’s so important to me. One of the joys of leadership is getting to have these long-term form relationships with folks that extend beyond the time that you spend managing them. What a joy it is to see someone in the first few years of their career, and then even after they leave your company, getting to see what they do, and they check in with you, and seeing where they go from there.

Peter: I think that was a remarkably, positive, affirming note to wrap this discussion on, so, at least for me, thank you, Sally. Thank you for taking the time. It was great having you and I don’t want to speak for Jesse.

I actually, because I actually have to bounce. 

Jesse: (joking) I had a terrible time.

Fantastic. Thank you so much. This has been wonderful. 

Peter: And that wraps up another episode of Finding Our Way. As always, you can find Jesse and I on Twitter. I’m @peterme he’s @jjg. You can also find us on our website, https://findingourway.design/, where you can find past episodes with complete transcripts, as well as a contact form. We read everything that comes through there. It’s a great place to send any comments or questions that you have about the show, anything you’d like to hear us talk about in future episodes and with that, thank you for your attention and as always keep on finding your way.

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