I had a wonderful six-year stint at Atlassian, helping the company scale exponentially during that time. I joined Dropbox because I am drawn to mission- and values-driven companies. Both Dropbox and Atlassian share those qualities. I was also excited to help shape and influence Dropbox’s evolving product strategy around the future of work, as well as lead a talented design team that I had admired from afar.
When I left my last company, the COVID-19 pandemic was just beginning. I started at Dropbox and have still not been to the office. I have worked from home my entire first four months, and that will continue for some months to come. Robert, an amazing colleague at Atlassian, said as I left: “I can’t wait to read your blog post on ‘Top things I learned starting a new job during a global pandemic.’” Well, this isn’t quite that blog post, but it is the first thing I have written since I joined Dropbox, and it does contain some lessons linked to his proposed title.
Starting any new job is hard and stressful, but I will admit that it has been especially difficult during these last three months. At any stressful or intense time, I think it is important to lean even more deliberately into your own set of frameworks and practices to help guide you through these moments. That is what I have been doing—going back to a framework focused on the biggest levers I have as a leader:
I focus on these aspects in that order. I firmly believe that if you get the first two right, your team will build amazing products.
During this uncertain time, the first person you want to focus on is yourself. You are no good to the people on your team if you are not balanced. I was fortunate to work with an executive coach a number of years ago to help define the professional and personal aspects of my life that I needed to invest in to remain balanced. My list included regular exercise and personal time away from family and work. Pre-COVID, I would train five mornings per week with a personal trainer or group class. Obviously I can’t do that now while maintaining social distance. However, I’ve kept up the habit of training every day, just in my own garage or by going for runs. The exercise has not been as high-quality as before, but it’s helped me stay centered.
I’ve also continued to read, but moved from business books to revisiting some favorite nonfiction travel books. This has helped distract myself from the pressures of work and the larger world context. Essentially, what I’ve been doing is managing my own set of inputs, to ensure that I remain balanced. All of that said, joining any new team, especially in a visible leadership position, is difficult and stressful. I found the transition hard and had to deliberately practice my own coping mechanisms in order to ensure that I stayed fully balanced.
The next aspect of people is the team you are running, plus your cross-functional partners. I always seek to understand people whenever I join a new team. I also want to humanize myself as a leader and meet as many people in as little time as possible. So I embarked on a listening tour to meet the entire Design organization of more than 150 people in small groups in the span of just three days. I asked a few simple questions about what was going well, what wasn’t, and what I could change in my first three months to improve how we operate. The wealth of knowledge I tapped into across those first few days has been invaluable in setting myself up for success at Dropbox. Actively listening and asking follow-up questions has helped me understand the landscape far quicker than reading documents or meeting with people one by one. People hold invaluable institutional knowledge that is difficult to uncover without making real connection.
While looking at the people on my team, I also wanted to understand team makeup. Diversity. Organizational structure. Skill sets. Levels. Open roles. The team ratios of designers to product managers and engineers. Plus all the operational aspects of the team. Fortunately at Dropbox, we have a wonderful Design Ops team that has all of this information and more in handy dashboards and spreadsheets. Looking at the big picture has helped me understand where the team might be out of balance and where we might have gaps.
The next set of people I needed to meet were my peers. I literally drew a map of the cross-functional partners I need to work with, and set about meeting them as quickly as I could. Building relationships is always hard, but when you can’t meet people in person it is doubly hard. Investing the time to get to know people personally, as well as learn what is on their mind professionally, has definitely helped me build bridges via Zoom.
Listening to peers, you start to get a different sense of the design organization. Uncovering different points of view is always interesting and helps you understand the ways in which cross-functional partners collaborate.
People are ultimately the foundation of any amazing team. And I think it is key that you spend time understanding the people in and around your new team, before you start to make decisions on how to shape the future of the organization.
I’m a firm believer in practices vs. process. Practices are guardrails and frameworks that you give to high-performing teams in order to help them achieve great outcomes. Process, on the other hand, is prescriptive and can add unnecessary friction for high-performing teams. You can’t walk into a new team and just make changes without first understanding how they currently work. For example, what practices does the team follow day to day? What design rituals do they already have? How do they define problems? How often do they speak to customers? How do they engage with cross-functional partners and bring them along in the design journey? These are questions that need to be answered to inform how you might support and shape the way they work.
I generally like to observe the existing set of practices for six weeks before making any changes. The interesting thing about Dropbox when I joined was that many team practices were in flux as everyone shifted to working from home. But I did make some adjustments right away. I heard during my listening tour that team members sometimes lacked awareness of work going on across the team. So I created a weekly design share-out session with three rotating 30-minute slots. We record it and then share the video with the entire design organization. This increase in visibility has (so far) been well received by the team. We are also looking to incorporate key end-to-end customer journeys in these share-outs to tie these inputs back to the customer. Inevitably, as your organization scales, a customer journey will span multiple teams. Designing across these boundaries is incredibly important. Focusing on the end-to-end experience from a customer’s perspective can help ensure a seamless user experience.
A final element is making sure the team knows that you will ask them for feedback on the new rituals every few months. You don’t need to change for change’s sake. You need to let your team get into a solid rhythm. But it’s important to include them in the creation and ongoing maintenance of team rituals. Often, as your team grows, a ritual put in place on day one becomes ineffective six months later. You must keep reflecting on and working to improve your team’s practices.
The last thing I look at is products. This might seem counterintuitive, but, as previously mentioned, I believe that the biggest levers I have for influencing the product experience are people and practices, which is why I invest more time in these areas up front. As I start looking at a product, I will focus on a set of core end-to-end journeys that I think (ideally backed by data and research) customers experience most frequently within our products. I want to see how intuitive these journeys are. I want to then understand whether we have teams aligned to deliver value and delight to the customer. Once you know this, you can then develop informed opinions on how your teams are organized to solve for these key customer moments.
Dropbox has five thoughtful company values. I mentioned at the start that I seek out mission- and values-driven companies. These five values tie nicely into my own framework for starting my tenure at Dropbox. For example, the Dropbox value of Make Work Human ties directly to my focus on people. The Dropbox value of They Win, We Win ties to my focus on practices around customer-centricity. So, after a little over three months, I am happy with my decision to join Dropbox and feel I’m set up to have a meaningful impact with the Design team and the company.