OpenAI

JD

We tackle both breadth and depth within the company. So strategically, we tackle big challenges with alignment, to get different teams aligned to a common goal. And we also get hands-on and tackle gnarly problems that require deep expertise, and deep customer understanding in a tricky area. So ambiguous problems are kind of the things that we love to tackle and try to build a transformative change within the company.

JD

I think that at a certain point in every designer's career, there's a moment when you understand the unique opportunity that design has to play a role in influencing people and companies to think differently. So when we're looking for challenges in the business that we can help solve, there are probably three things that we try to make sure there's room to play a role in at the same time.

One is strategy. Do we see a business opportunity or a business impact or customer impact that we feel we can get our heads around and help drive? That's something we often do in partnership with product, engineering, and other people in the business.

That's usually step one and there's a ton of communication and learning and discovery around that. The other thing is being able to provide some storytelling around, "Okay, here's what we're thinking," and that's the part where we start to help coalesce people around the idea that we should even consider making some part of the product better. And that storytelling component is probably one of the biggest things I think we've had success with as this team and this group of people.

Lots of people can write PRDs, and lots of people can make prototypes, but it's a real challenge to be able to start telling a story at a very, very early stage and be able to show how we can start to craft something. That ability for us to move very, very far upstream into strategy and kind of shortcut people through storytelling and craft to seeing what possible answers might be or how we might be able to approach a problem in a very practical way - those kinds of three things of strategy, craft, and storytelling have been, I think, super killer for this team. They are superpowers that everybody on our side here provides, above and beyond what a lot of the other teams are expected to provide or have to provide in their role as designers here. So those are the key things that I think we apply to these ambiguous problems that have been successful.

JD

The web redesign is a project we worked on for over a year, and it crossed all three of those thresholds and had different people influenced in different ways across our team. All three of us contributed in many ways to the project. I was with it for the entirety of the 12 months. So I saw it from the early stage of trying to build the core thesis for why change was necessary on the web product itself.

We were not just looking at how the experience had gotten a little bit gnarly at certain points. We were trying to surface opportunities for it to get a lot better. Bringing in new business opportunities and strategy, and trying to build a new information architecture that would allow for the new bets and strategic bets we were making to better land with customers. I guess we're all proud of it as a first step to kind of reinvigorate the kind of experience that customers can have with Dropbox.

It brings a more premium feel to how customers experience the product. But it's just the first step though. We've got a long way to go. There's a lot of stuff that I'm more excited about even delivering after this milestone. What's engaging for me is that we now have a diary study that we did with a bunch of customers on the web redesign, and we learned about the 10 things that they want the most. So we feel that we're on the right track and that there's going to be even more value coming soon.

JD

The biggest thing was that we had previously had an experience where our multi-product strategy was to more or less kick people into different standalone products with loosely connected infrastructure and back-end systems, which we saw was not resonating with people due to too much friction. For example, if someone was trying to quickly edit a PDF, add some signature fields, get it signed by somebody, store it, and then track when the document was sent out to get signed, that previously would have taken them to three different products with very different user experiences, and different identity backend systems. Customers were telling us they didn't want to use this, and the data showed we were getting very low take-up. 

So we focused on integration - how do we integrate these things tightly, and build on common UX patterns so that a customer feels like they can do this much more fluidly than they could in the past? That was probably the biggest change we made.

JD

A brief point to make is that we have this concept called 'core collaboration hours,' which is a four-hour overlap with the coasts. As a result, people often try to cluster meetings within that four-hour window every day. As a maker, I find this tremendously valuable because I can do deep work in the other zones outside of that window. For example, my morning in Central Time allows me to be incredibly productive. I remember in my last job, I had meetings scattered from eight in the morning till five at night.

In the past, it was quite challenging to focus on a problem and execute it due to meetings being scattered throughout the day. However, with our virtual-first working environment, we designed it to have just those four hours of overlap and the rest of the time allocated for deep work. This arrangement allows me to be incredibly productive.

JD

Building on that, it's as if we're asking ourselves, "Does this need to be a live synchronous conversation? Is there another format that could be as impactful or potentially save us time?" That's another topic I often discuss with people. Additionally, I remember seeing encouragement to clean up my calendar very actively. Over time, especially as a more senior designer, you accumulate numerous one-on-one meetings from past projects across different parts of the organization. Therefore, I regularly clean up my calendar, with a recurring reminder to do so. This practice is incredibly helpful.

JD

On many projects, I've been trying to bring together cross-functional teams to work more closely. However, it's something that has gotten a little lost in some parts of the business. We use those core collaboration hours and designate Monday for a 30-minute stand-up to ensure we're all aligned with the goals for the week.

And we're all ensuring that we're doing the right things. On Tuesday mornings, we review the work, whether it's design or otherwise, and engage in a round-robin feedback session. We execute on that feedback until Thursday, then hold another morning meeting to review the progress. Finally, we sprint to a Friday review, where we expand the audience to include a broader group of stakeholders beyond the project's day-to-day operations.

This rhythm has been beneficial because it allows people to stay in sync as a team, attend other meetings and collaboration hours, focus at the end of the day, and then come back with new ideas. We can iterate quickly together, both within the team and with a larger group of people. This basic rhythm, where everyone knows they have an opportunity to reconnect, review, and give feedback, has been helpful. It's something I've started incorporating into the projects I join.

JD

You need to embrace ambiguity and feel excited by it. Embrace the feeling of being overwhelmed, push past it, and dive into the fear of the unknown. I believe that people who tend to be biased towards action are particularly valuable on this team, but I think, in general, at Dropbox, the more you can create momentum and understand when to push things forward, the better. There are a lot of people here, and it's crucial to ensure that you're generating energy and sharing the vision to get people excited and motivated to move forward together.

I think those are two big points that immediately come to my mind. Additionally, I believe there's something incredibly valuable about direct, respectful human communication. The more you can cut through the fluff and truly focus on the goal, ensuring that you're always steering the conversation back to what you hope to achieve, whether in the conversation or the project, the better. This approach is particularly helpful because, with so many people involved, there are numerous ways information can be interpreted.

So the more you can centralize things and focus on the expected outcome, I believe the more you can ultimately unify people and get them to move in the same direction. I'd love to hear from other people as well.

JD

I might also add deep empathy for the customers we're trying to serve and a ruthless commitment to crafting great experiences. This entails caring deeply about interaction details, typography, visual design, motion design, and all the fundamentals that contribute to creating a memorable experience. We have the opportunity to be extensively involved in the creation process and set the tone for the design throughout the organization.

JD

We're a pretty new team, and I think there's room for us to define, over time, different archetypes that are successful in the role of a principal designer. One thing I've been looking into and reflecting on a lot is this book by Will Larson called "Staff Engineer." Larson constructed this book by conducting numerous interviews with principal and staff-level engineers to understand how they approach their jobs.

It's not exactly related to design, but there are patterns to learn from. He also has this cool article on archetypes. For example, some people excel at creating the architecture for a solution. Others are very skilled at being project leads and guiding teams through detailed execution. Then, some individuals are adept at sitting down and directly solving a problem.

He has all these cool archetypes, and I do think that having a clear sense of your strengths is key when stepping into ambiguous problem spaces. Figuring out the right archetype to embody based on what you're seeing and hearing is crucial in being useful and propelling the project to the next stage.

Many people in this room are adept at wearing multiple hats. For example, right now, we may need someone to act as the architect and define what this project is about. Then, we can involve other team members such as designers and product managers. Once we're in "solve mode," all of us smoothly transition between these archetypes. This ability to switch roles seamlessly is something we value in our team, even though it's small. Can you wear different hats at a senior level and swap them at different stages of the process? That's something I've been reflecting on a lot. It's also intriguing that there's a book or manual out there, albeit written for engineers, that addresses these issues. I hope to see something similar tailored for designers and leadership at the individual contributor (IC) level someday.