No successful project gets done without meeting deadlines, staying on budget, and managing lots of different people. There’s a lot on the line. For the leaders of high-performing design groups and million-dollar design firms, these pressures are felt daily. Seemingly never-ending deadlines, constant people management, and strategic thinking in an ambiguous tech landscape are part of the territory. Seeking insights into how design leaders deliver on these demands while remaining balanced and focused was one of the motivations for writing this book. As it is with other CEOs and founders, the strategies and tactics of how to find balance and personal growth is always on our mind.
The theme of this chapter might seem more appropriate to being included in a self-help book. The reality is that the personal growth and mental health of the leader is inexplicably linked to the success of any business. Without exception, all of the design leaders we met with felt that ongoing personal growth and leading a balanced life were critical to their success as company or team leaders. Exploring the habits, routines, and rituals of these leaders gave us insight into the inner workings of their paths to success. Their perspectives, hard-earned lessons, and strategies will give you a renewed appreciation for the attention required to lead a balanced lifestyle and the connection to a successful design business.
Finding the Right Focus
“I’m CEO, so my customer really is my team. I’m making sure that everybody who works here can achieve and become the best that they are.” This comment from Dominic Bortolussi, cofounder of The Working Group, is incredibly insightful. The simplicity of this statement belies the importance of the impact it can have on a design leader’s actions. “Through that exploration, I discovered that my real customer is not my clients; my customer is my team. That was an interesting shift because I’d always assumed that my customer was my clients—the people that I was building software for.” Bortolussi reflects on the insight and how it led him to change the way he leads his organization. “That was a not-so-subtle shift. My recognition of my type of leadership has evolved over the past few years. I discovered that I’m a leader of meritocracy, a democratic type of leader, a leader who asks opinions of other people and then expects them to step up; not an autocratic leader. Not a ‘me first’ leader. Not a top-down leader.”
Understanding where their strengths lie is a breakthrough moment for design leaders. Knowing how to put those strengths to work for the benefit of the team is another breakthrough step. “I do everything else that needs to be done, all the business things. All the hats that need to be worn, I wear those,” says Marty Haught, founder of Haught Works, a small development team based in Boulder, CO. “I recognized at one point when we were at nine people that I was doing a lot less coding and a lot more management. I recognized that to continue on that path or get larger would mean to hire people that would do these other things. I really didn’t want to do that. I wanted to have smaller teams that didn’t require me to be 100% management.” Haught is talking about that moment when leaders realize they need to be true to their limits. Growing your company, and thus growing into a different leadership role, is a requirement of success. Whether the company is big or small matters less than whether the leader is clear about their own path and the path of the company. Personal growth doesn’t depend on the size of the company or team, but there does seem to be a correlation with maturity.
Finding your place in the team can only happen when the team has found a focus for its collective efforts. Being able to put guidelines around who you are as a design group helps the team members define their ideal contributions. When clearly described, this focus trickles through the organization and allows the design team to know how they should behave when new projects come their way. “The one thing about us is we say ‘no’ first,” says Instrument’s COO, Vince LeVecchia. “The trap is to say yes to everything in a creative agency, get the work in, figure it out later. With us, if you start out by saying no to the mediocrity or the thing that just looks good, you really then curate all the work you do.” This hyper-focused thinking was common among mature leaders and their organizations. Not just focus, but focus with a purpose. It can be tempting to say yes to everything that comes your way. Certainly, when you’re starting out, you might have to do just that.
“We took the easy road that was in front of us,” reflects Steven Fitzgerald of Habanero Consulting. “We got caught up in thinking that it was about doing something for a client that would help them out of a problem, rather than focusing on stuff we would be awesome at. That’s the cycle we go through and that’s the lesson.” Losing focus or allowing distractions to determine the path was a lesson often learned the hard way but often the most valuable lesson leaders reported on. “When we live outside our purpose, nothing works well. I’m not saying it’s easy to understand and just stick there. It’s very hard. That’s the whole challenge.”
These hard lessons in finding focus appear to be consistent with the changing demands of a growing business. The longer your business has been around, the more distractions there will be. Successful leaders recognize this escalation and counter with increased focus. That often means ignoring opportunities or turning away certain projects. From personal experience, I can attest to how difficult this is. I’ve made numerous investments in side projects and new service offerings that have not borne any fruit. The key is to surround yourself with smart advisors and partners that can help you stay the course. Recently I’ve invested in operations people that act as gatekeepers and protect me from distractions so I remain focused. The rewards have been significant. This book, and the one before it, would not have been possible without those people playing interference to my distractions.
Partners and Support
Entrepreneur and author Jim Rohn once said that you are the average of the five people you spend the most time with. This appears to hold a lot of truth for our design leaders, too. Surrounding yourself with a great team makes dealing with the stresses of running a high-functioning design team so much easier. Another point worth making here is that a supporting team isn’t restricted to the group of people you work with directly. Our design leaders almost always referenced their families, clients, and mentors in our conversations.
“First of all, I prioritize the things at work that make it not just tolerable but enjoyable,” says Brian Williams, of Viget. “Hiring people that I love to work with is one of the things. We also try to be as selective as we can with clients so we can be working on things that we’re passionate about.” For Viget and many of the other companies we visited, taking the time to select the best team members and filtering for the ideal clients made the work tasks easier. Although this overlaps with our chapter on talent, it’s worthwhile reaffirming the importance of having the right people in your organization. Almost everything design leaders talk about in their work and home lives comes back to people. Support, culture, inspiration, and excellence all relate to the people that design leaders have in their orbits.
For any leadership position to be successful, there has to be a significant amount of support. Not just the support of the organization but the support of family and friends. Surrounding yourself with people who really know you and can help you find that balance even when you think you’re lost. “Work-life balance is hard,” adds Uncorked’s Marcelino Alvarez. “I think my wife’s been a great supporter of what we’ve been doing. She ... is in advertising, so understanding the industry that we’re in certainly helps.” Gesturing to his phone, “There are times when I get the nudge of ‘turn it off’ and I think it’s a good nudge to have. I think that the balance is more of an internal one where I’ll start thinking about something. It’ll be in the back of my mind. I’m thinking of something else. I’m not here and present. I’m nodding my head but really I’m just trying to crack this thing. And that’s hard because people who don’t know you might think, ‘Wow, he’s really nodding his head a lot.’ But I think people who do know you are like, ‘Stop. Stop thinking about the thing. I know that you’re thinking about that meeting or that conversation or something at work.’ Be honest with yourself. Taking a day to work from home or turning it off on the weekend and just hitting a reset point I think is really important.”
Where the Inspiration and Support Comes from
“A lot of experimentation, trial and error,” says Sarah Tesla about finding the right place to get support and inspiration. “I am fortunate. My husband is a founder of a digital creative agency in Vancouver and has been doing it for a decade, and he’s got two partners. So he’s been a limitless resource for me, which has been great.” Family and friends are undoubtedly where design leaders turn but not everyone is married to a seasoned pro. What Tesla says next is the clue to the mindset that seems to set successful leaders apart. “In honesty, I really am pretty humble about what I know and what I don’t know.” This humility and willingness to learn is the key. Being in a constant state of learning prevents the top design leaders from getting stuck. Whether they are leaning on a partner, spouse, or a team member, they are universally coachable. “I rely a lot on my team in that sense, to be experts in what they do and allow me to try and figure out what I have to do,” concludes Tesla.
For most of the leaders we spoke to, support is at their office every day. In spite of the importance of family, friends, and external advisors, their closest support comes in the form of their partners. “There are a lot of leaders here,” says Dominic Bortolussi of The Working Group. “I also have three other partners. There are four partners in the business and they are each a phenomenal leader in their own area.” It’s worth hearing from Bortolussi what each partner does to understand how they compliment each other. “We have Chris Eben here. [He] is very visible in the community, does a lot of speaking engagements, is very active in our business development. So his leadership is very visible and [he] is sort of the traditional corporate leader who is out there speaking and pointing the direction. Andres is also a phenomenal leader. He leads all of our project operations and has amazing empathy and ability to connect with people. His leadership is really through example, through his amazing communication abilities. Jack is our technical director and his technical leadership is through example, by doing. He’s perhaps the most dedicated worker I know. He puts his head down and solves problems with people, and he’s getting really good at incorporating other people into a problem-solving system.”
As illustrated by Bortolussi’s description of his partners, there’s a lot of specialization for each area of leadership. The partners use their respective strengths to support each other and the business as a whole. Unlike the popular media’s love affair with the lone leader, the reality is that most businesses need some kind of partnership to be successful. “Fortunately, we have complementary strengths and mine tend to be operational,” says Tiffany Farriss, one of the two CEOs at Palantir. “I’m very good on the finance side. I manage the books and I’m also the more technically minded of the two of us. So for the more technical engagements, I’ll go in and pitch those. George is excellent at vision and strategy for the company as well as communication, getting our brand and communicating those things. So there’s been kind of a clear division. He tends to work on the company with the exception of finance, and then I tend to work on our clients and then the finance piece.”
Another leading design firm, CloudFour in Portland, OR, has a similar partnership, which started out with four partners but now is down to three. “We’ve worked with each other for seven years. And Lyza and John have worked together longer,” tells Jason Grigsby, CEO and cofounder. “John has since left and started another startup. Now Lyza, Aileen, and I run the business on a day-to-day basis.” Grigsby points out how the lives of the partners are not limited to what’s going on at work. “The things that are going on in our personal lives impact what’s going on in the business, whether we like it or not. Being able to figure out how to find alignment ends up being a big thing. And we’ve had periods of the company’s history where we weren’t aligned, and things were really rough. But in times when we’re aligned at a high level, all of the small stuff on a day-to-day basis usually works itself out.”
Grigsby cautions with a wry grin, “I think if you’ve got people that you’ve worked with for quite some time, you could still screw it up.” In business, nothing is guaranteed, even with great partners to support you. Markets change, trends pass, and new technology shows up at every turn. So how else do design leaders reduce the risk of making mistakes and creating positive outcomes?
Creating the outcomes you want is not something you leave to chance. Successful design leaders are used to crafting solutions for their clients and they seem to use these techniques in their own lives as well. In their daily lives, many of them take a design-thinking approach to how work and home life fits together. Deliberately designing your daily routine instead of being reactive was a common approach. For some, this can be as simple as choosing to live close to the office to avoid a stressful commute, but mostly it’s about developing a routine that allows for personal enrichment while also dealing with the demands of company leadership.
Successful leaders acknowledge that growth and harmony are also a product of timing. The needs of the business change over time, and so do the opportunities to learn new skills. Unlike riding a bike, finding the right balance is a lesson our leaders have to keep learning, because the context is always changing. What works when they’re running a company of five people is very different from the things that are needed when there are 50 people to lead.
“I think it’s a yin-yang type of thing,” says Bryan Zmijewski, of finding balance in personal and professional endeavors. “You’re going to go through periods where you’re going to get lots of inputs that you weren’t expecting and you have to deal with them.” Zmijewski has lead his company, Zurb, through Silicon Valley’s most challenging decade. He likens finding harmony in his life to ocean fishing. “There are times where you want to set course but you’re just holding on because the waters are turbulent. In these moments, you don’t try fishing. When the waters are calm, you go fishing. That’s hard to learn because oftentimes we become impatient in wanting to create things when there’s really not circumstances or an environment for them to be successful. So I think the lesson I learned in probably the last few years is that you have to be patient.”
“I’ve always loved being an employee and I was really fortunate to have great bosses. So I never felt that I was lacking in that.” SuperFriendly’s Dan Mall describes how his past experiences helped him deliberately craft a design firm around his lifestyle needs. “Really, the motivation to find balance came when I had kids. I just wanted to stay home with my wife and kids a lot. I thought it would be selfish to ask any company I worked for to let me do that. The places that I worked, the cultures just weren’t really good for that; it would have been really selfish of me to do that. So for me it was a good time to see if I could just at least work from home and spend more time with my family and then figure out how to sustain myself and my family through that.” In most modern economies, the idea of freelancing or working from home is nothing new. Mall has taken this concept to the next step by starting with family priorities and designing a business around that. The irony is that even designers don’t use their design skills to craft their careers. Successful design leaders show us that it’s necessary to approach lifestyle and careers as a design problem to be solved with many of the same tools and exercises used in their everyday work.
Viget’s Brian Williams describes how his decision to craft some of the aspects of his business routines around his family priorities has had a positive impact on his overall life balance. “In terms of making sure the work part is enjoyable, it’s a typical time-management discipline-type stuff. I’m fortunate that I can walk to the office so I don’t have a big long commute. I can be around in the morning, get the kids on the bus, be home in time for dinner every night, that kind of thing.”
Williams adds additional perspective: “The business is successful enough and we have enough of a team where we’ve delegated stuff and spread the workload. In most cases, I don’t have to work weekends like I did for the first five years.” It might not be realistic for many to start out with a company that can provide the support for all the leader’s career criteria. Design businesses can take time to grow to the point where the team is large enough to do what Williams describes. He cautions that it required effort and a long-term vision to get where he is today. “Getting the thing off the ground seemed endless. I’m not driven by financial success. I mean the company is financially successful in every measure but I’m not targeting some huge exit or something along those lines. My goal is to create a business that is sustainable and enjoyable for me and for the staff and for everybody that’s involved. We’ve decided we can do something we want to do for the next 20 years while we raise the kids, remain a part of the community, and stay connected to all these things that I love to do.” Williams summarizes his approach and suggests a strategy that puts long-term outcomes before pure business goals, “If you change the dynamic and say, ‘I want to create this sustainable work environment,’ I think that can change the way you balance your time and your life.”
Designing a balanced life isn’t something that has to wait for the company or team to grow large. Instilling values that promote balance can happen at any point. The key here is that there’s a deliberate approach to finding a way to get the work done and not burn out. The design leaders we met with have learned that by designing their lives for a positive outcome, they flatten out the inevitable bumps in the road. They actively seek out time to spend with family and friends. In fact, 45% of design leaders consider time with family the best stress relief.
“We used to think about the concept of work-life balance but I hate that term. It feels like a zero sum game,” remarks Steven Fitzgerald, CEO of Habanero Consulting Group in Vancouver. “We’ve evolved our thinking about the term. Now we have a value based on harmony. You should create an environment where you can experience passion in the different parts of your life that really matter. It’s very temporal and it’s very specific. For me, it’s things like riding my bike, it’s Habanero, it’s my kids and my family and my community. If I can deeply engage in those things and experience passion in them, I take energy from that and I put it into the other ones.”
Fitzgerald makes the distinction between harmony and work-life-balance. “The concept of work-life-balance conveys the feeling that you’re going to be a deadbeat dad and work hard at work, being a successful businessman this month. That’s not the way I see it. When I had a great night with the kids, I show up at work better the next day. When I have a good ride into work or a good ride on the weekend, it helps me be a better dad. It helps me be a better partner to my wife. It helps me be better at Habanero. That passion fuels the other things. I think it’s the opposite of a zero sum game.” This insight is of paramount importance. You can’t sustain good design leadership if you’re not taking care of your mental, emotional, and physical health. Making these things a priority and carving out the time to achieve harmony isn’t just a nice-to-have, it’s a requirement of successful leadership. Put family and exercise into your schedules before they fill up with meetings and other distractions.
Designing a harmonious career starts with the smallest elements. Organizing each day and week adds together to create more manageable months and years. “I think the other piece for me, really, comes down to just sort of how I’ve kind of organized myself and my days,” says Scott Baldwin of Yellow Pencil. “I tend to use a good system to plan around my tasks. Knowing what I need to do and what I need to achieve for that week gives me a head start. I think it’s kind of a bit of a bastardization between a ‘get things done’ and kind of a Stephen Covey approach. It follows the idea or concept that we need to make space for these bigger things and objectives in our lives, which are our priorities. Rocks, in the Covey1 language.”
“I see it as flow, not balance,” says Jeb Banner of SmallBox. “There’s balance on a moment-to-moment level, where you need to make sure you’re managing stress and activity and all that, but to me, life is about flow. It’s about things feeding each other and creating positive energy in both directions, work to life. I don’t think those are going to become any more separated going forward.” This last point is extremely important. Modern design leaders, or any contemporary leadership role, isn’t going to look like the leadership roles of the past. Your dad’s-era CEO who clocked out at 5 p.m. and never got an email at noon on a Saturday is now a quirky history lesson. Today’s leaders are inextricably connected to their work, wherever they are. Smartphones and mobile devices blur the lines between work and play. Banner’s point about the lack of separation is something all our design leaders deal with every day. Instead of pretending there is a clear line between work and everything else, the most successful leaders acknowledge the vagueness and embrace the integration.
The Importance of Exercise
Exercise came up in our conversations almost every time—either the importance of it or the frustration of not getting enough. This book probably doesn’t need to describe the importance of exercise in our lives, but what is relevant to this book is the large percentage of design leaders that credit exercise with stress relief. Whether their preference was golf, running, cycling, yoga, or simply walking while on their frequent phones calls, they are inserting exercise into their days. For some it was a deliberate habit, for others an opportunity to socialize while burning calories, and for still others it was a way to escape the constant buzz of their devices. Sustaining a busy schedule starts with having the energy to do everything that’s planned for, and more. Leaving physical health to chance is a sure-fire way for leaders to run out of energy and focus when they need it most.
“I like running,” says Marcelino Alvarez when we asked him how he gets disconnected from the constant lure of the smartphone and into the detox zone. “For me, running two, three times a week really helps. You don’t have to carry a piece of technology with you. You can’t read an email while you’re running. Aerobic exercise helps you to free up brain cells to think about problems. It’s nice to digest ideas while you run.” Running was a favorite among several of the design leaders for the reasons given by Alvarez. The upside to running, hiking, or cycling is that it allows these design leaders to either check out completely or ruminate on their challenges without the constant interruption of device notifications. By choosing activities that gave them a chance to check out a little, they were often, sometimes subconsciously, finding ways to rise above the day-to-day fray and slip into a meditative state. Alvarez continues to make the point about creating time for activities that get you out of the daily effort, “I like photography and I like fishing, too. Basically anything that forces me to get out and enjoy the water, the sun, especially in the summers here, is a good escape.”
“I exercise a lot. That’s become very critical in my years,” says Scott Baldwin, Head of UX at Yellow Pencil. “I tend to run about at least three or four days a week. So that physical aspect of things, getting out and clearing my head, is a really important part of doing good work here.” Baldwin, who is based in Vancouver, explains how important routine is in keeping stress at bay. “It’s become part of the ritual. It has its ebbs and flows, like when my wife travels and I have to travel, or something like that.” Having a way to frequently blow off some steam or just get the blood flowing was a common thread in the interviews. Leaders can’t be expected to stay focused without some way to recharge the batteries.
“I do some yoga and some meditation,” says Jeb Banner of SmallBox. “I need to do more of that. I generally do that two or three times a week, along with some exercise. I take a lot of walks when the weather permits. [I have an] elliptical at home that I use.” If yard sales are anything to go by, Banner might be the only person that actually uses their elliptical at home. When we asked Aurimas Adomavicius of Devbridge how he finds harmony and balance in his life, he didn’t hesitate for a second. “Just a lot of drugs.” Then he chuckles and dismisses his comment. “I’ve found that exercise is incredibly important. Specifically, running is very, very important for managing my stress level.” After hearing so many of these anecdotes, it was no surprise that 62% of design leaders reported using exercise as their primary way to relieve stress.
The physiological rewards of exercise are well understood. We all know the benefits but often struggle to develop these good habits. Making sure that physical exercise finds it’s way into their busy schedules, design leaders often rely on a combination of internal and external motivators. “My wife is a personal trainer, so she forces me to exercise,” laughs Dan Mall. “And so as often as we can, she tries to get me to play racquetball with her because she really loves playing racquetball, so we’ve been really getting into that lately.” Having a partner, spouse, or friend to nudge you in the right direction is often all our design leaders need. Another way to make exercise part of your day is to connect it to the things you’re already committed to. “I am a walker or a pacer. I can walk for miles and miles,” says Nancy Lyons of FastSpot. “I’m not a runner or a biker, but I walk. I have walking meetings. I’ll walk around blocks on calls. I’ll walk on the walking work station. I’ll walk after work. Or late at night when all the houses are sleepy.”
Walking meetings and standing desks were very common tactics used by the design leaders. Making walking or other forms of exercise part of the company culture is a way to integrate it into everyday activities. “I like playing basketball so every once in a while, I have friends that will organize a three-on-three basketball tournament, so as much as I can, I try to do that,” says Mall. “Releasing those endorphins in that way is just really, really great.” It’s probably not too presumptuous to suggest that if you’re not making exercise and healthy living a priority then it’ll be harder to achieve success in leadership. Scheduling time for healthy activity almost has to come first. If leaders don’t carve out time ahead of their weeks, then without fail that time will fill up with something else. The foundation has to be set.
All Work and No Play
Not all design leaders choose to sweat their stress away. At least a quarter of those interviewed preferred frequent vacations as their ideal stress reliever, while another quarter said that they would hit the bar after a tough day. This time at the bar is mostly about making time for friends. After exercise, time with friends and vacations were the most mentioned outlets for stress. This balance between work and play doesn’t look the same for each leader. Some choose to blow off steam daily or weekly, while others wait until they are completely burned out. “I believe that to be successful, you have to work a lot,” says Devbridge’s Adomavicius. “I don’t have the mentality that you just work eight hours a day and that’s enough.” Adomavicius describes an almost as extreme but personally effective strategy to finding balance: “What I’ve found is I become busy and allow for some burn out. Then I take a big break. I believe that there’s an engagement curve that looks like a sine amplitude, where essentially, you as an individual, you gain focus in these intense sprints and you’re very effective when you gain that focus. But you can only be super effective and work 12 hours, 14 hours a day for a limited sprint, then you have to wind down and you have to decompress.” This approach is extreme but not as uncommon as we first expected. Working intense hours for months at a time and then disengaging completely to recharge was mentioned several times. The Working Group’s Dominic Bortolussi took an extended sabbatical after several years of intense work. “It was fantastic. I would recommend at least four months. I began with three months and it was clear that I needed more time, so I extended to four months.” Bortolussi spent much of his time completely disconnected from the office. Apart from a handful of check-in calls, he was “off the grid.” His sabbatical included riding his motorcycle to L.A. from Toronto, surfing and playing music in Bali, studying meditation in Thailand, and studying yoga in India.
“I prefer having these really aggressive sprints and then good decompression moments after them. I have time off where I travel, or I do something where I’m decompressing and not as engaged with work,” explains Adomavicius. “I found that if I can do that, I’m much more creative and productive in those work sprints versus having a normalized engagement level of, ‘Oh, I worked the regular number of hours a day for four, six months,’ and then take a vacation or something.” Finding a rhythm that works for your particular style is ideal. As we’ve said before, no leader is the same. Each design leader needs to find a pattern that keeps him engaged and let’s him recharge when necessary. “I think there’s some type of rhythm in nature that I just synchronize to, and I just need to be able to detect the phase I’m in,” says Marcelino Alvarez. “If I’m finding that I’m burned out and not as engaged and not as creative, I just need to step back a little bit and give myself time. When I see that interest peaking again, then I need to really hit it and work a lot of hours and work weekends. Because I know that in that period when I’m most engaged and most excited, I will produce the best results. That’s my mentality.”
If reducing stress is the goal, then Adomavicius and others feel they are going to achieve this when they deal with the issues head on and work even harder. “I really enjoy the company and the growth,” says Velir CEO Dave Valliere. “There’s definitely times that are extremely stressful, whether we’re dealing with onboarding a new client, kicking off a new project, or maybe there are some issues that we’re working through with a client, or working through with internal staff, or those growth pains that I was talking about before. What I find is during these stressful times, I work even more. It seems crazy, but I think that the more time that I’m spending focusing on these areas and the more attention that I’m paying to the issues, the more I am reducing my stress. I would imagine that there’s a lot of folks that are in these positions that feel more anxious when they’re away from work than when they’re in it, regardless of what’s going on at the time in the organization. That’s definitely something that I’ve felt over the years is that my anxiety levels go down when I’m more actively engaged in what’s happening. For sure, my wife hates that aspect. Even when we’re on vacation, I’m still going to be sending email, still responding to things. But I think that if I didn’t, I would feel more anxious.”
Design leaders often attribute their desire to stay connected to the business as a responsibility to their team. “I think that it’s the responsibility that I feel to the rest of staff that’s driving me to want to spend more time on a problem,” says Valliere. “I need to be able to think about the different angles to this particular situation that we’re dealing with. I think if I was more disconnected from them, I would feel more anxious. So it’s actually just being more involved with work that is actually what’s making me relaxed.” Whether your style is to pull back or dive deeper, the insight is that each leader needs to find their own rhythm. Learning to read their patterns gives these design leaders some power over their stress. By combining that insight with their individual remedies, the design leaders are able to stay creative and energized.
Planning for a Harmonious Future
Design isn’t just a solution for their daily work. Design is also a solution for how design leaders craft their lives. An unavoidable part of designing any solution is the testing phase. Having a solution in your head is one thing, but getting that solution out into the real world and tested against harsh realities is quite another thing. “When I first started SuperFriendly while working from home, I thought, I’m going to have a very strict schedule,” says Dan Mall. “I’m going to work 9:00 to 5:00. Nine o’clock, I’m going to clock in—no earlier. Five o’clock, I’m going to clock out—no later. That just didn’t work for me. Work just bleeds in and out of that. My kids would come downstairs and want to play, and I would just be angry at them because this was work time and I had to get work done.”
“So what I do now is the opposite, where I work a really long day with really long breaks in between. So I get up at 5 a.m., and every morning I work from 5:00 to 7:00 because it’s quiet and that’s my most productive time, when I’m waking up and sort of becoming more alert for the day and starting to think about the day. And then, from about 7:00 to 10:00, I go have breakfast with my kids, drop them off at school, hang out with my wife. Start work around 10:00, 10:30 and then I work until about 3:00 or 4:00 when my kids come home. Come downstairs, we play for an hour, half an hour, something like that and then I work until 7:00 or 8:00. So I’m technically, like, at my desk from 5 a.m. until 8 p.m., which is a really long day but I take a lot of long breaks in between. That has actually helped me to have more balance than if I’ve been having a strict schedule. So I find that’s working for me lately.”
Not all planned solutions need to be complicated lifestyle experiments. Sometimes all you need is a way to get through your to-do list with a little more momentum. “Think of it as of marginal gains, or small-serve, incremental pieces,” suggests Scott Baldwin at Yellow Pencil. “I tend to focus on the three to five things I need to do this week. I think about how to involve other people in the tasks. I do a lot of planning ahead of time, to make sure I’m already thinking about next week’s calendar and next week’s meeting today, not next week.” Baldwin’s approach is to narrow down the focus of his effort to the most important items on the list. He backs this up with finding ways to get help and possibly even delegate if necessary. “I ask myself, ‘what are the things that we’re doing this week to move those forward?’ This sense of incremental gain over time is empowering. People with a big goal, or a big objective, start to freak out and wonder how the hell are they going to do that. If you break it down into small pieces, it’s not so scary. You ask, how about this week we work on this proposal? And next week, we maybe go talk to this client. And two weeks from now, we maybe do this. Over time, and incrementally, we might get to that big goal.” This strategy isn’t unique but its simplicity belies its effectiveness. Breaking goals down makes them accessible and manageable without diluting the motivation of having an exciting challenge ahead. Having a strategy, any strategy, provides peace of mind. Baldwin adds with a smile, “I’ve always been a zero inbox kind of guy, or just about, but I think a lot of it is just coming down to having a clear head and taking clear actions at the right times.”
Rules and Routine
“I’ve been very, very strict in how I manage when I’m working and when I’m not,” says Ross Beyeler, CEO of Growth Spark. “There are always exceptions. Every rule has an exception, but most of time, I will not start work before 10 a.m. and once I leave the office, my email is off. I will not check email when I’m outside of the office and I won’t start checking again until 10 a.m. the next day. As soon as I’m done on Friday, around 5 p.m., I’m totally inaccessible over the weekend.” In our observations, this discipline is not rare but tends to be associated with more mature leaders. Not everyone we spoke to drew hard lines between work and the rest of their lives. For some design leaders who prefer staying somewhat connected, it might not be as simple as turning off your phone or ignoring email for days at a time. For many design leaders, there is a middle ground, where weaving all aspects of work and life into each other is better than completely separating church and state.
Defining the times and spaces for work and then communicating that clearly to the people around you is necessary if you want boundaries. In the absence of boundaries, clients or staff will simply assume you’re available. This goes for significant others and family, too. “We’ve been doing it so long at this point, it’s almost routine,” says Tiffany Farriss, co-CEO of Chicago-based Palantir, “and what I realized is that balance isn’t about carving separate time for different things.” Farriss, who runs the 35-person firm alongside her husband, George DeMet, feels that it’s about integrating things in a way that doesn’t compromise their children or their personal relationship. “So we have these times that are off bounds to talk about work stuff, unless it’s an urgent matter. The dinner table, for example. No phones at the dinner table, and after 9 o’clock at night, you just don’t talk about work. We try to keep our weekend contained, but if we need to, we respect that the other person might not be in that same place. So if there’s something I’m working on or if there’s something that is really bothering me that I’m trying to solve ... and I need his help, if it’s outside of normal work hours, I ask him if he can help me with it and when might be a good time for him. I have to be respectful of his personal time the same way I would be of any of my other colleagues.”
Farriss’s insight is great guidance for leaders whose partnerships go beyond the office. In partnerships between spouses, you have to treat your partner as you would anybody else. Assuming they want to talk about work after hours is disrespectful to the other person’s time. Discussing when and where it’s okay to discuss work helps set the boundaries in a healthy way for everyone. This might also extend to comanagers and staff. Letting them know when you are available after hours or on weekends helps them understand when they can bug you with questions or updates. Using the tech available helps, too. Calendars and out-of-office responses tell people when you’re not around. I book time for exercise and family time into my calendar so my team doesn’t accidentally book me for a meeting during those times. Being explicit about where your boundaries are is helpful to the people around you and gives them clear guidance about when you’re available and when you’re not.
Acquiring New Skills
Finding harmony often means growing skills. Our conversations with design leaders almost always included questions about their personal approach to growing as leaders. We already knew from our own experience that growth as a leader is often a consequence of the challenges we face. These external influences are certainly not consistent. They come in waves.
This seems obvious, but we wanted to know what they are thinking about or doing during these ups and downs that helped them improve as leaders. Dan Mall of SuperFriendly says, “I take very calculated risks. I think the skill that I lack most is bravery. That’s been really hard to work on for me because I’ve always taken risks that I know have no consequence. I’ve never really taken a risk that I didn’t know had no consequences. I’ve never really risked if it weren’t going to pan out. So I think that’s a thing that I could work on and definitely learn more about. I think I like to work with people that want to learn stuff. I find that even though I hire people that are really good at what they do, if they don’t come into the project thinking that they’re going to learn something, or not expecting to learn something, and just expecting like, ‘I’m going to execute and get out,’ I find that it’s not interesting. We do good work, I think, and those projects end up good, but it’s not interesting if we’re not learning something together. The people that I really love working with most are the people that have no idea how to do the thing that we’re going to do, and then figure it out along the way. I’m very attracted to those people. People that come in and are just like, ‘I’ve no idea on how to go about this, but I’m very confident in my own learning abilities that by the end of it I will be an expert.’ I’m very drawn to those kinds of people.”
Some leaders learn through trial and error, while others learn by watching or listening to others. The best leaders balance these two approaches. Going to the source of the knowledge is something we tried to do with this book. Either approach brings results, but the latter brings results faster. The caveat is that the leader needs to know where their strengths and weakness lie so they know what gaps to fill. Listening to advice from a mentor on a skillset that you have no strength for might be a waste of time. Knowing which skills need your attention focuses your search for solutions and insights. “Part of it was delegation,” says Dominic Bortolussi of The Working Group, “by leaning on my partners to be the full leaders in areas that I wasn’t as good at. The other part of it was discovering what I am good at. Knowing the type of leader that I am. Through speaking with knowledgeable people, mentors, and reading, I also developed those skills just through practice. By setting aside about an hour each week, generally on Fridays, to do some writing and thinking about how I want to continue with that shift. Just setting aside time was important.”
Soft Skills Have Big Upsides
Most of the skills that these design leaders thought of as being paramount were also the skills hardest to measure, and may be the hardest to acquire as well. “Besides empathy?” says Jeb Banner. “Focus, for sure. Being able to tell you any minute of any day what are the things that matter most. Sometimes, I get off track, and part of it’s because I’m starting new projects so often. So my mind is split between the nonprofits I’m involved with and the businesses I’m involved with and the ideas for things that are further down the pipe. I don’t have a mind that naturally focuses, so I think I’m going to have to find a way to build more structure around my thinking and put more blinders on. Part of that is I’m committing this year to be more analog and to have less screen time, which I think leads to ADD thinking and behaviors.” Changing behaviors, and acknowledging that they need to be changed, is a clear sign of leadership maturity. From our research into user experience, we also learned that behavioral change tends to be most effective when connected with accountability. This too was a sign of the more mature leaders we met with. “I need more accountability. I need to allow myself to be held accountable. I need to push my goals and commitments into a larger audience so that audience can come to me and say, ‘Hey, you’re way off track.’”
“I realized it a long time ago, but this week I just said to somebody yesterday, I’m actually making decisions and doing things that are going to affect about 15 people’s lives this week—hiring, promoting, totally changing their lives,” says Vince Lavecchia with a wide grin. “I don’t really know how it happened. We just have been building on this idea of creating a great agency with great people. My job is to create a great company. Justin and JD, they make the work great. And so if I can find great people, and they can make the work great, we can continue to grow and live in a great environment. And we’ve just been doing that and chipping away at it and making decisions along the way.
Growing Companies by Growing Leaders
Leaders don’t evolve in a vacuum. Their growth is connected to the groups they run. Instrument’s Vince Lavecchia tells a familiar story about company growth and the personal challenges that it brings. As one grows, so does the other. “When we were four people, I was like, ‘Man, what if we get to eight people?’ And when we were 12 people, we were like, ‘We’ll never get to 40 people.’ And when we were 40 people, we were like, ‘Holy cow! This is huge. I don’t know if we can even run a business bigger than 40 people.’ We just didn’t know. And then all of a sudden we were 80 people. And even then, I’m telling people, ‘Look, I’ve never done this before—we’re doing the best we can do,’ and we’re killing it. So yeah, it just has gotten there. But I really put it to the people that we found, the talent. Well, I think it has more to do with them than us.”
“Oh, there’s so many things,” says Sarah Tesla with a wide smile when asked what else she still needs to learn on her path to becoming a design leader. “I think leadership is always a work in progress. I think that the more people that you become accountable to, the more you have to sort of, I don’t know, push that drive, get people on board. What’s the vision? Like, what are they getting behind? And, yeah, figuring out how to lead—that in itself is just a daily challenge. Am I being a leader by example, or am I sitting back too much on this one? It’s always trying to find that fine balance.” Knowing when to lean and when to lean back can be tough decisions for leaders. Finding the balance between the two is the magical land of perfection we all struggle to find. Tesla feels that her growth is also deeply connected to the choices she makes about who comes on board. She believes strongly that having the right balance of people in the studio says a lot about her leadership maturity and about her growth as a leader. “It’s a fine balance of people. The team has been very carefully curated and, not to make that sound weird, but I’m just protective of that identity, I guess.” Seeing their companies and teams as a reflection of their personal growth is a trait we noticed in several leaders. They see the world around them as a mirror to what’s happening inside them.
These leaders are not leaders by accident. They all share a desire to lead. Their path to leadership might not always be direct or expected, but they all understand they now own that role. We wondered how they might advise themselves if they were given the chance. We were interested in how their experience might inform other leaders. With more knowledge, insight, and confidence, these current leaders can help younger or less experienced leaders make better choices. “I’m happy with my life now, so I wouldn’t change too much,” says SuperFriendly’s Dan Mall. “But I would encourage some things that I did just to be a little bit stronger. I was always the weird employee that liked reading statements of work and operations manuals and things like that. I’d probably encourage myself to do more of that stuff. Without that stuff and having the bosses I had that encouraged me to do those things and were fine with it, I wouldn’t be able to run a company. I was really fortunate to be able to learn from other people’s mistakes and their failures. I like to observe those things and put them into practice. So I think I would suggest to my younger self, ‘Do as much of that as you can and soak that up, because it’s good training for running a company.’”
As Sarah Testa pointed out, leadership is a work in progress. For leaders, their personal growth is not separate from the team’s growth. Their advances reflect on the organization that they build and nurture. The organization they create in turn influences the growth of the people that work there. It’s all connected. “That’s my whole philosophy around it,” says Steve Fitzgerald. “That’s one of our values at Habanero. We’re trying to build an organization that respects that dynamic in people’s lives and allows them to create the professional sphere of that harmony in a way that respects other things that are happening in their lives.” For these design leaders, there is a virtuous circle that connects their attitudes toward growth. The more they seek challenges that help them grow and learn, the more their teams do too.
If you are the leader, then your primary customer is your team.
Having personal and professional purpose gives your growth strategies focus and clarity.
Leaders invest in people and processes to keep distractions at bay.
Surround yourself with advisors and mentors that provide insight into areas of growth.
Most leaders need to constantly be developing their soft skills, like negotiation, presentation, and conflict resolution.
Protect your personal and family time by communicating to your team when you’re unavailable. Use your calendar to book this time before it’s too late.
Use design strategies to design an ideal life. Mapping out your days, weeks, months, and years gives you amazing amounts of control over your time.
Exercise is the primary method for reducing stress and building reserves for a busy schedule. Walking, running, cycling, and yoga top the list of activities.
Carving out time specifically to spend time with friends and family is considered by design leaders to be a critical part of a harmonious life.
Work partnerships can be the source of harmony or stress. Find partners that complement your strengths and weaknesses so there’s balance among you.
1Dr. Stephen R. Covey, First Things First. For those not familiar with the metaphor repeated by Covey, it goes something like this: a man stood in front of a group of high-powered overachievers and said, “Okay, time for a quiz.” Then he pulled out a large wide-mouthed mason jar and set it on a table in front of him. He produced about a dozen fist-sized rocks and carefully placed them, one at a time, into the jar. When the jar was filled to the top and no more rocks would fit inside, he asked, “Is this jar full?” Everyone in the class said, “Yes.” Then he said, “Really?” He reached under the table and pulled out a bucket of gravel. Then he dumped some gravel in and shook the jar causing pieces of gravel to work themselves down into the spaces between the big rocks. Then he smiled and asked the group once more, “Is the jar full?” By this time the class was onto him. “Probably not,” one of them answered. “Good!” he replied. And he reached under the table and brought out a bucket of sand. He started dumping the sand in and it went into all the spaces left between the rocks and the gravel. Once more he asked the question, “Is this jar full?” “No!” the class shouted. Once again he said, “Good!” Then he grabbed a pitcher of water and began to pour it in until the jar was filled to the brim. Then he looked up at the class and asked, “What is the point of this illustration?”