I was directing design. And I was utterly stuck.
Years ago, I distinctly remembered thinking that being hired for a Senior Design leadership role meant the company was ready for someone like me — an Intrapreneur. During the interview process, I shared what had worked for me in the past, and I asked all the questions about culture, innovation, and design that I could think of. I felt confident I had done my due diligence. My expectations were the company had reached a breaking point and needed help. While I didn’t come from a traditional business background, the company knew the status quo wasn’t working.
I was exactly what they needed.
When I started my new role, I started with what I knew: design, front-end development, and product management. My plan was to focus mainly on developing people, teams, and processes to help us achieve some quick product wins. And it worked! After 12–18 months of ramping up skills and capabilities, the work was being seen and felt. The team and I were making a difference. As a result, I was invited to different kinds of leadership meetings with access to executives, senior leaders, and high profile projects.
I felt valued by my peers and the organization.
Confident in my seat, I relied on the same approaches that worked during those first 12–18 months as a means to influence the organization’s future. That the same plan did not work. All the things that worked at the product level kept me from being successful at the strategic level. The momentum my team had built stalled, I was responsible for fixing it, and I was utterly stuck. I didn’t know how to move forward.
I wasn’t prepared for this challenge.
I was anxious because I didn’t understand why what had worked before wasn’t working again. I was frustrated because I was treated like a novelty, despite a track record of previous success. I was scared because I had sold my team on the idea of our importance, and I didn’t want to let them down.
My doubt made me want to protect my team from harm.
I knew all the things I needed to do more specifically to develop better relationships, influence leadership, sell my value, become more strategic, etc. I followed the guidance of well-known design agencies, in-house teams, and influential voices in the design field, through courses, workshops, and other extended learning programs. I implemented the tools, processes, and techniques I was taught.
I assumed all the guidance on design management would work.
Yet, the more I followed the guidance being prescribed by industry leaders, the more anxious, unprepared, alone, unheard, and stuck I felt. The case studies being shared only highlighted the positive. The leaders providing the guidance had not themselves been responsible for decisions being made. The courses lacked any real-world situations or scenarios that involved change above the product level. I kept asking myself, “how are other leaders and teams successful with change while I have struggled?”
I told myself I was alone in this struggle.
This pattern would repeat itself a few times as it followed me from organization to organization. This is what I felt like:
The first time an executive asked what I was doing in the room, and I struggled to find a concise answer
The second time my boss was fired just months after my arrival
The third time I was asked to remove elements of my presentation because another group would feel threatened
Every time someone said, “I don’t even know why you’re here, but glad to have you here.”
That particular time my boss told me, “No, I’m not doing that. I really like my benefits package.”
Moving forward when you’re stuck
I often think about this pattern: how I’ve always felt different as a leader inside an organization because I was a designer. How frustrated and isolated I’ve felt at times — especially when my peers and leadership labeled my work as pretty or the final step. How easy it was to blame the organization or my colleagues for not understanding me.
What I want to say to designers in such situations today, it’s essential to know that design can solve many things, but it’s not the only solution.
When taking on leadership roles, we often feel overwhelmed by a firehose of foreign information, processes, ceremonies, personalities, and unwritten rules. It’s understandable that when faced with these new factors, we rush back to design autopilot. We return to our teams, our practices, and our craft because frankly, it’s easier and more comfortable to do.
And yet, when we go on autopilot, we may feel stuck without a clear forward path and subsequently struggle to find the joy we once had in our work.
In modern psychotherapy, titration is used to help with trauma. This process exposes a person to small amounts of distress to build up a tolerance and avoid becoming overwhelmed.
In each phase of our career, we are faced with a new firehose of responsibilities. It is overwhelming. I’ve found in my research and in my work, the most significant jump is moving from managing design to directing it.
By exposing ourselves to small amounts of discomfort, we build up our tolerance to all things new and avoid being overwhelmed by the firehose. The more we expose ourselves to the tools, ceremonies, processes of others, the higher chance we have to meet our own expectations. The more we practice our new skills, the greater chance we have to hold leadership accountable for the changes they say they so desperately want and need. The more we hold leadership accountable, the more relief we feel as design leaders, and the better we can serve others.
Breaking free from our own status quo
Sometimes, the only way to break free from the status quo is to break free from our own status quo. We spend so much time trying to fix things with design when sometimes we just need to let go of design. We need to trust that the processes and practices we cling to will be replaced with something more appropriate for the situation we’re facing.
I was exhausted with my own comfort zone.
Returning to my own story. I grew tired of the status quo, and frankly, I grew tired of my own story. To find joy again, I had to set a new expectation of myself. I was the one who needed to change. I was the one who had to move past traditional design management guidance. I had to look beyond design to empower my team, be more influential, and create the kind of impact expected of me.
I felt more alive than I had in a long time.
Once I began looking outside of design, I felt more prepared for situations and conversations I had previously been part of. In turn, my preparation helped me to be resilient, relieved, and heard. This is what I felt like:
The first time I reverse engineered a colleague’s presentation to get additional headcount
The second time I presented recommendations I could live with
The third time I confronted my boss about the shitty cultural norms protecting the loud voices from the quiet
The last time I left a role knowing I had done all I could have but needed to move on so I could live with myself.
I felt more confident and prepared as a strategic leader
The things that have helped you make an impact in your design career are the things that are going to separate you from others as a leader. They will help you succeed in ways you can’t predict or plan out. While it’s impossible to see now, as you learn more than your craft, the things that others perceived to be your weakness will become your strength.
I know it because I’ve lived it.
If you’re in any of these situations now, you’re not alone. If you’re feeling any of these feels, we’re here for you. If you’re ready to learn new skills to enhance design, just let us know. And if you’re not prepared to try something different, that’s totally okay. We’ll be here when you’re ready.
This article was originally published in The Deep — Second Wave Dive’s newsletter for design leaders and executives. We send out lists of things worth sharing straight to your inbox. Subscribe here.
My thanks to Andy Morales, Jaida Regan, Sarah Mills, Joshua Bullock, Greg Storey, Ellis Givens, and Matthew Stephens for their feedback and time.