This article is more of a personal story. It took me a long time to translate my thoughts into a public blog. My hesitation stemmed from lingering insecurities and the fear of being judged by others. Nevertheless, despite these reservations, I have chosen to share it, believing that this challenge likely extends beyond my own experiences and that someone may find value in hearing it.
In the past two decades, the role of a designer has undergone significant evolution in the industry. With the emergence of the web and smartphones, the need for an improved “user experience” suddenly became evident. This quantum leap in design’s importance elevated its status, leading companies to establish dedicated design departments and granting design professionals executive roles within organizations.
Having witnessed this evolution throughout my career, I had a grand aspiration of becoming a Head of Design.
There was something truly captivating about design leaders with the prestigious “Head of Design” title in the tech industry. They exuded confidence, charisma, knowledge, eloquence, and... they just looked so cool. They seemed like someone worth dreaming of becoming one day.
After encountering various detours and trials, in 2019, I finally realized my dream and became the Head of Design at DoorDash. I was so proud and felt accomplished. I immediately updated my title on LinkedIn and also printed a business card with the new fancy “Head of Design” title on it so I could proudly hand it to someone at the next networking event.
As I started this position, it exceeded my expectations on all fronts. The job provided me with a tremendous amount of autonomy and creative freedom, particularly in a company like DoorDash, which fosters a strong bottoms-up culture and does not impose prescriptive art direction from executives. I was able to shape the direction of product design, have a significant say in design craftsmanship, define processes that enhance team efficiency, and build the team in a manner aligned with my vision.
Moreover, the role afforded me privileged visibility and control over aspects that were previously inaccessible, such as confidential business insights, behind-the-scenes executive decisions, and a substantial budget. Every day, I was overwhelmed with the joy of being in the driver’s seat and witnessing my own growth and learning. It was unequivocally the best career decision I had ever made, and I gloriously sprinted forward without looking back even once.
However, the longer I have held this position and grown in my role, the more I have come to realize the true magnitude of my responsibility. Being an executive leader is challenging in general, but being the Head of Design takes it to a whole different level.
The Head of Design is a lonely position.
In this role, you find yourself at the top of your discipline within the entire company. There is no other executive peer who speaks the same design language that you are most familiar with. Whether design-related outcomes are positive or negative, you are the primary spokesperson. When faced with difficult decisions that could potentially impact the experience of millions of users or influence the careers of those you care about, you are the ultimate decision-maker in a design organization. Often, these are challenges that you have never faced before; there’s no clear protocol to follow, and your decisions often rely on instinct and first principles. Yet everyone is looking for the right answer from you quickly.
The loneliest aspect of it all is that you can’t openly discuss this sense of isolation with the team too often, as it might be perceived as insecurity or incompetence. I fear that such a perception could potentially lead to anxiety and doubts about the leader. As a head, you’re expected to be the center of calm and a guiding beacon, and there’s very little room for mistakes. Once I had this realization, I felt hopeless and sad. It felt as if my job was to paint an ideal image of the Head of Design, and I couldn’t be myself.
However, I didn’t give up and continued some investigation into how I could get out of this feeling of being stuck. After some months of research and soul-searching, there were a few valuable lessons that helped me regain my bearings. I wanted to share them with those who are facing similar challenges. The tips could be helpful for leaders in any position.
Tip #1: Embrace your limits and imperfections.
You’re only human, after all. It’s important to start with humility, honesty, and empathy for yourself, admitting that no leader can ever be perfect, know all the right answers, or be liked by everyone. Just as we ask our own employees, it’s okay to be vulnerable and ask for help and advice when needed. I’ve found that teams tend to connect better with leaders who can show vulnerability from time to time.
Tip #2: Engage in a few projects where you can delve deep.
Even as the head of a function, I’ve learned that it’s important to stay deeply involved in a few priority projects that you’re passionate about and have a comprehensive understanding from head to toe (not just head — no pun intended!). When you’re working alongside teams on specific design problems, the feeling of isolation lessens and the sense of belonging strengthens. After all, most of you are designers at heart.
Tip #3: Strengthen the design leadership bench as your first team.
Some say that as you climb higher up the ladder, your first team should become more cross-functional. While there is some truth to this, this concept is challenging to achieve when you’re the head of a function, as each functional head tackles different problems and goals with limited overlap. In many cases, I decided to seek guidance from within. I feel fortunate to have built a strong and seasoned design leadership bench that helps me tackle challenges and brainstorm solutions together. It’s comforting to know that there’s a tribe of trusted individuals who speak the same language, and they are my sounding board.
Tip #4: Establish connections with other heads of functions within your company.
This could be your cross-functional peers or your own manager, who’s probably another functional leader. During my internal interviews with various functional leaders, it became evident that the struggle with isolation is not exclusive to the Head of Design. Whether a function is well-established or newly formed, large or small, the sense of being alone emerges in every conversation. Many leaders also expressed that they rarely receive specific directives and guidance from their own superiors because they are perceived as the foremost functional experts.
I have been fortunate enough to find a few executive mentors with whom I can regularly discuss shared challenges. Three bits of advice that resonated with me include:
(a) Embrace the mindset of being the owner of the company rather than just a functional leader. This perspective enhances confidence in making decisions and upholding principles.
(b) Even as a leader, there is a safe space to experience failure. Our culture emphasizes the importance of learning from mistakes, and we grow as individuals and as a team through this process.
(c) Developing an authentic voice is crucial for successful leadership. It is important to express what you genuinely mean and believe rather than simply saying what sounds right, even if it may not be the most popular idea.
Tip #5: Take the initiative to connect with Heads of Design from other companies.
Engaging in coffee chats with various design leaders in comparable roles revealed a common sentiment shared among them, regardless of their tenure as heads or the scale and composition of their design teams. While many companies recognize the significance of design, only a few have truly harnessed its transformative potential. Numerous design leaders are still navigating their paths and striving to establish a meaningful presence within their organizations. Discovering that I am not alone on this journey was immensely helpful. I enjoy exchanging valuable tips, insights, and experiences and expanding my network of sounding boards.
Tip #6: Explore resources from various channels online.
I learned a lot from the stories of other design leaders, and I highly recommend two particular resources: High Resolution | Finding Our Way (cohosted by my ex-manager from Groupon, Peter Merholz) They are rich in insights and wisdom and provided valuable guidance during my soul-searching process.
To sum up, there are numerous strategies to address and reduce the sense of isolation that often accompanies leadership roles. Begin by showing empathy towards yourself and seeking support from both internal and external sources. Forge connections with other department heads, adopt a mindset of ownership, view failure as a stepping stone for growth, and nurture an authentic voice. By implementing these approaches, we can conquer the hurdles of isolation and thrive as impactful leaders.
I hope this article was helpful for the current and future Head of Design, as well as other functional leaders. Being a functional leader is a lonely but extremely rewarding journey.
I am also curious to hear how you navigated similar challenges as a leader. Feel free to comment away or reach out to me for more discussion!
Helena Seo is the Head of Design at DoorDash. We’re actively hiring seasoned designers. Please visit our career page and check out the Design section!