Chris Meeks, UX
A systematic thinker who sparks change and unleashes potential.
Hello, could you please introduce yourself ☺️
I'm Chris Meeks and work at Dropbox as a principal designer. I live in Austin, alongside my wife and children. Although I often refer to them as young kids, they are growing faster than I realize!
I received a BA in graphic design and ceramics and then started my career as a print designer. After a few years of that, I found an opportunity to shape digital experiences, first through Flash, then through learning HTML and CSS. I found exploring the boundaries of what was possible to be a fun and creative exercise. This experience led me down the path towards digital product design.
Could you share the transition from graphic to digital product design?
While I was designing at Gallup, an organization known for polling, it was an exciting time. Our polls were often referenced by a captive digital audience for the 2008 US election. Within the company, there wasn’t anyone specifically focused on the craft of translating designs from Photoshop (yes, Photoshop) to web with precision, so I leaned into serving a business need while growing in an area that was important to me. I was kind of hacking things together and trying to figure out how to make my designs come to life in an interactive way, such as complex data-visualizations and other data-intensive products.
The position gave me a free space to explore and learn. I’ve found this to consistently be the best way to learn a skill: experimenting within a working environment. It is a win-win — the company gets what it needs while you enhance a skill that you care about. Throughout this experience, I gained insights into the fundamental distinctions between print and web platforms.
In print design, you have tight control over colors, bleed, and precise measurements. Any errors could lead to costly misprints. On the other hand, in product design, quick corrections are possible and there is always room for experimentation. You still have to be thoughtful and detail-oriented, but you can push more boundaries and construct multiple plans that you can quickly pivot to if necessary.
How would you define a principal designer?
Some principal designers have a breadth of experience and primarily connect dots in creative ways (generalists) and others have a depth to their skill that allows them to fulfill a critical need for the business (specialists). Those needs can differ greatly based on company size, customer demographics, and industry, so there isn’t a prototypical specialist that’s important for every company. But some models are: architects, strategists, visual designers, and storytellers.
A book I enjoyed, which describes some of the key differences between generalists and specialists, was Range: Why Generalists Triumph in a Specialized World. That book articulates that generalists can often make creative connections between seemingly-disparate areas. For instance, a generalist principal designer might see a connection between a product strategy that failed, a gap in talent, a competitive threat, and a UX trap in the product. If you're a specialist, it's unlikely that you'll easily perceive those connections, given your deep focus on a specific area. However, a visual design specialist might be the key difference in a product winning or losing in the market—high-craft is absolutely essential, so these skills are in high demand.
AI is going through a new category creation phase right now, which may prove challenging for specialists outside of that domain. It’s vital that specialists stay elastic both within their specialty and outside of it. Their extensive domain knowledge often limits their ability to see beyond the existing boundaries and institutional knowledge they’ve accumulated over the years, while generalists often see budding technologies as simply new inputs in their process.
“If you’re a specialist, it’s unlikely that you’ll easily perceive those connections, given your deep focus on a specific area. However, a visual design specialist might be the key difference in a product winning or losing in the market—high-craft is absolutely essential, so these skills are in high demand.”
How did you make the decision to join Dropbox?
When I was entering the job market, there were three criteria I identified as non-negotiable.
First, I wanted to work at a company that did good. It’s so important to me to benefit people’s lives with my work. Bringing joy to someone’s day or saving them time that they can reinvest in their communities, friends, and family is my most important motivator. Dropbox makes money directly through subscriptions from customers. This makes it easy for me to sleep at night. As a father, I often think of the world I’m supporting with my work and want to make sure I’m improving it for my children.
The second factor was that I wanted to make. I’ve had the privilege of managing and making throughout my career. I’ve found that, personally, my energy increases when I’m able to craft solutions to difficult problems and often decreases when my time is spent managing others. Though I deeply appreciate the role of management, and understand the success of ICs is dependent on supportive managers, making is where my cup is filled.
Lastly, I wanted balance. Early in my career, I wasn’t acknowledging that rest and rejuvenation actually make us better and more consistent makers. I still hustle and pride myself on getting a lot accomplished, but I wanted to work at a company that meaningfully supported a healthy and balanced life, which Dropbox does through great benefits, including mental health support and the opportunity to take the time off I need to recharge.
Another great thing about Dropbox is they have Core Collaboration Hours. Being a Virtual First company, this approach involves a four-hour block every day (11-3 CT), dedicated to collaborative activities. The rest of our time is generally spent on deep work. This works great for me because I know that my mind is the most able to focus on deep work in the mornings.
“It’s so important to me to benefit people’s lives with my work. Bringing joy to someone’s day or saving them time that they can reinvest in their communities, friends, and family is my most important motivator.”
Can you share a recent project you led?
The most recent one was redesigning web and refreshing our product visual language.
Like many companies, our web app was starting to suffer from feature bloat and disorganization. Additionally, Dropbox has a lot of valuable features that customers are still discovering. Our goal was to rearchitect the experience to both better support customers’ existing behaviors and surface our additional value in an intuitive and discoverable way.
This was a significant undertaking due to various challenges. One was the fact that the web interface had not undergone a comprehensive redesign in around seven years. My responsibility was to address this, navigate through the complexities of working with different teams, and build a shared understanding that supported our customer and business goals. These teams were actively shipping updates, but there was a need for a holistic perspective and a forward-looking vision for the evolution of web.
I had to collaborate with multiple teams to ensure that the comprehensive viewpoint aligned with the evolving needs of the business. Teams are often naturally inclined to iterate and optimize within their own area, but we had to break that mold.
Let’s use the analogy of a house. If a team is responsible for the kitchen, they'll be refining and optimizing the kitchen, and similarly for other areas like the bathroom, living room, etc. However, issues in the house often exist not just within individual rooms but also between them. Addressing these challenges may require more than just refining existing spaces; it might involve moving the kitchen or the bedroom, or even knocking down walls.
To navigate this properly, the team needs someone with the vision, scope, and expertise to understand how these pieces need to shift – just like an architect. The challenge lies in architecting a better way to organize these spaces and having the organizational support to implement these changes effectively. I worked with various teams and leaders, overcoming technical challenges, and collaborating with engineers, product managers and design teams.
How did you get started to redesign web information architecture? What actions did you take?
When I came into the project, it had already been kicked off with a number of great designers and cross-functional partners in the discovery phase. I learned the insights from the team and mapped out the problem space to visualize my understanding of the problem in as much depth as I could. View full interview.
When I came into the project, it had already been kicked off with a number of great designers and cross-functional partners in the discovery phase. I learned the insights from the team and mapped out the problem space to visualize my understanding of the problem in as much depth as I could.
I do that out of habit now when I work on complex problems—whether it’s multi-product identity or other gnarly problems that involve many aspects of the business. My process involves reviewing past research, journey maps, the backlog, as well as collecting other data points like business strategy and competitive factors. I also explore customer forums to identify the most upvoted items, allowing me to triage this data. By synthesizing information from these sources, I can identify what has already been discovered and which opportunities still seem unexplored.
For the redesign of Web, I worked with cross-functional partners to diagnose which of the biggest opportunities had the least definition. Then, it was a matter of creating more definition through design sprints, user testing, and feasibility planning.
One additional challenge we faced was that we were also were looking to refresh our product visual language at Dropbox, but wanted to do so in such a way as to decouple UX improvements from visual design. For the visual refresh, I led a group of designers who created 19 diverging visual design concepts and partnered with specialists from brand and design systems. After narrowing these down to three concepts, we conducted thorough customer testing, gathered feedback, and involved various leadership perspectives in the process.
When you start a project, how do you earn trust without people reporting to you?
At the end of the day, trust (and this is true at any role) is earned through showing up, being consistent in your work ethic, and maintaining attentiveness in every conversation and review. It involves making it evident that you genuinely care about addressing the problem you're working to solve and then being willing to tackle those difficult problems.
Could you share your framework to be more impactful?
I aim to build trust and lean into the undefined problems wherever they are. For instance, if I'm working with a team on a defined problem, sometimes you realize, “Oh, no. There is a bigger strategic problem here.” I don't really care whether it falls under my responsibilities as a principal product designer to solve that bigger problem. If nobody is able to raise their hand and take on the challenge, I will say “Ok, I will do it.”
For instance, when helping our team tackle multi-product user identity, I learned from the considerable engineering efforts but also needed to define the complexity of the challenge in front of us. As we acquired various companies, we were dealing with different identity systems that had an architectural misalignment in places. I needed to map that misalignment and construct a multi-phased plan for aligning our experiences. This ended up being a project in which I earned the trust of some key stakeholders and leaders in the organization by being willing to pitch in.
For the second part of the answer, I've really benefited from the mentorship of Alastair Simpson, VP of Design at Dropbox. He shared with me this framework, which is called the three Ds for how to have impact:
Drive
Delegate
Defer
When you have a lot of challenges across a team, this framework ultimately enhances impact and focus.
“I don’t really care whether it falls under my responsibilities as a principal product designer to solve that bigger problem. If nobody is able to raise their hand and take on the challenge, I will say “Ok, I will do it.”
What excites you about being a designer in the next few years?
AI is the obvious answer, but I won’t pick that. It will definitely be exciting and transformative, but I’ll pick something else that is not typically as emphasized.
I'm passionate about digital design and physical product design because these tools allow humans to have the capacity to engage more with the world. I feel like a lot of the technology that we've built collectively over the years has pulled us away from the dynamism and vitality we once had.
I feel like there is a growing potential to experience the marvelous world that is through assistive technology.
Google Lens is a good example. I can utilize my camera to identify a unique flower I find on a hike, delve into the plant's history, and gain insights into its traditional uses passed down through generations. I can learn this rich history of a plant because technology created this experience between us. It's fascinating to investigate how we can deepen our understanding of the physical world and actively engage with it through the digital tools we have.
