Reflections on My Year of Remote Design Leadership

When I accepted a Design Leadership position at Connected in late 2019, I could never have expected the extraordinary circumstances that would transpire by the time my first day rolled around on March 16, 2020—the first day of pandemic lockdown in Toronto. 

Little did I anticipate that not only would my first meetings with my team and others at the company be virtual, but my working relationships with both clients and other employees would continue to take place remotely over Zoom and Slack for an entire year with no end in sight.

Embracing the Culture

Joining a well-established team as a new leader was both intriguing and a little frightening. In my past leadership roles I’d grown teams from 1 or 2 members to 15+. 

Now, with a new challenge to tackle my tried-and-tested approach of getting to know my team wasn’t available to me. Gone were the casual coffee chats and shared working spaces that bring people together naturally and effortlessly, replaced by video calls and presentations that felt a bit more formal.

Luckily, my team was welcoming and comfortable with collaborating, and throughout my first weeks and months we got to know each other in a more casual way through team activities, remote socials, and project share-outs. But we also realized that remote team building activities needed extra time to be planned around everyone’s busy schedules now that spontaneous team building wasn’t a possibility. We learned together that these casual (yet planned) moments together were crucial; afterall, there’s nothing like a lighthearted activity or a good laugh together to bring team energy and morale up, especially when the world is going through such a strange time.

Having recently re-joined the consulting world from a product company, there were aspects of this role and company that felt familiar to me, and of course others that were quite foreign. Although I was most recently at a product company, there was something calling me back to the excitement of working on a variety of products and platforms with different clients again. In fact, some of the differences between working at a consultancy and a product company were so fascinating to me that I presented a talk at our weekly Discovery Clinic on some of them during my first few months. A lively discussion followed where other Connectors shared varying experiences and impressions. This was one of the first of many great learning opportunities Discovery Clinic provided and has been a highlight of my week since joining.

The Transition to Remote Work

One of things that impressed me most in my first few weeks and months  at Connected was how quickly and seamlessly everyone transitioned to a fully remote structure, despite the fact that there hadn’t previously been a big work-from-home culture at the company. I’m sure for many behind the scenes (especially our rock-star IT team) this was not as easy as it seemed to me as a new employee. But the swag bag and the laptop I received on my first week, the set-up of my accounts, and the onboarding meetings and presentations couldn’t have gone more smoothly. The only tough part was finding time to get up from my desk and stretch every once in a while! I met person after person for coffee chats, learning as quickly as possible about their roles and departments, and how designers and researchers collaborated with them to build better products.

But the success of the transition to remote work, and the energy that fuelled it, weren’t the only things to surprise me. The liveliness of the culture was palpable even over Slack and Zoom. Two all-hands meetings per week (company wide stand-up and demos + ”kudos”) helped make me feel connected to the rest of the employees. The banter on Slack was lively and fun, and helped ensure there was ample opportunity to casually connect with others in different departments. One of my first remote socials was a spelling bee I competed in with around 15 others, which was both hilarious and thrilling! Participation in activities ranging from process improvements (transitioning the company’s signature Playbook and Product Thinking Workshop to online formats, for example) to socials and teaching opportunities was much higher than I could have anticipated. There was, and still is an overall sense of involvement and inclusivity which I have really appreciated especially in a work-from-home environment. 

As the year of remote has evolved, however, we have been re-evaluating some of these regular online cadences to remedy Zoom fatigue and burnout. One thing I’ve found critical to remember throughout this pandemic is that it’s essential to continually adapt, iterate, and test processes to learn what works best for right now. We instinctively know this when it comes to project work – we’re always hypothesizing, prototyping, and experimenting as we build products – but without deliberate intention applied to evolving our team activities, some of them can grow stale or less impactful over time. For example, our weekly team meetings have ranged from project share-outs and tool tutorials, to getting to know each other through activities like Two Truths and a Lie, Show & Tell, and User Manual share-outs for new team members.

Living the Mission and the Values

What’s most impressive is that Connected’s values of teaching and learning shine through much of what the company engages in, both internally and externally. There are Discovery and Delivery clinics every week or two, where techniques and methods are taught and both in-flight and completed projects are shared for feedback, testing, and learning. Roundtable discussions on wide-ranging topics are common during lunch hours, long-form industry reports and blog articles written, and webinars held. There’s even a mindfulness group which meets weekly on Zoom and I’ve found it a great way to start the day with intention and clarity.

Before I joined Connected, I had mistakenly thought that “Product Thinking” was fairly well known and adopted, like Design Thinking. However, I soon learned that Connected is actually rather unique as a consultancy in this space—not solely focused on strategy, design, or development, but all three equally and in collaboration. It is our mission to build better products using this unified approach, and executing strongly against this mission that has attracted top tier, ambitious clients.

There are some great examples of this cross-functional approach in action that come to mind: 

• a designer pairing with a developer over an open Zoom line with videos and mics turned off. The pair would check in with each other to ask questions and share screens as they worked, with a researcher dropping in to learn through osmosis how design and development come together in the build phase
• an engineer collaborating with a researcher, designer, and strategist to share a complex cloud-based product concept with an internal group at our weekly Discovery clinic through a helpful analogy 
• a researcher, product strategist, and engineer meeting up for a distanced walk to brainstorm ideas, before returning home to create a document of product concepts that the client loved 
• a researcher and designer bringing bite-size research insights into wireframe files in Figma – helping the whole team understand why features were designed a certain way

For designers and researchers especially, building better products means building products that have a positive impact on people’s lives by putting their needs, desires, and jobs to be done at the heart of ideation and execution. In my past, I’d often seen companies skimp on research or omit it altogether in the early stages of product building, but when I joined Connected I was impressed by the many case studies demonstrating a full end-to-end, user-centered approach. 

Starting with foundational research, successful products are connected back to those learnings using the jobs-to-be-done theory, customer profile canvases, and the value proposition framework (among many other techniques and tactics found in the PT Playbook). This well-defined, repeatable approach, grounded in the belief in continuous improvement through experimentation and testing, has been inspiring and exciting to contribute to.

But it’s not always easy. Especially when collaborating remotely using methods that many of us are more comfortable executing in person – like research synthesis, concept ideation, and user interviews. Tools like Figma, Miro, and Airtable have been life savers as we’ve adapted these processes to a remote format, and we have even found that some phases of our process work even more efficiently using these tools than they did in person.

The Present and Future of Design at Connected

Looking back now on one of the most unusual and challenging years most of us have ever lived through, it is important to reflect on design and how it relates to a world that may never return to the pre-pandemic “normal”. How have industries been disrupted? What new hopes, fears, and dreams do organizations need to address as they build better products for humans who have lived through a pandemic?

Joining a new company at the start of all this has given me a fresh perspective on how teams operate, and recognize how a careful balance of skills can tackle the world’s big challenges. 

I was fortunate to discover that I was arriving to lead a more senior team than I had expected, a group of individuals who had a strong toolkit of tested methods under their belt. But as the composition of the team has shifted over the past year and we rapidly grow, it’s crucial to objectively evaluate each individual’s skills to ensure we have the right balance, versatility, and seniority on the team. To do this, we’re currently in the process of building and collaboratively iterating on a skills map and a career development framework.

Keeping autonomy, mastery, and purpose in mind, motivating the team towards constant growth and development will be the key to innovating products for this new world we’re encountering. What excites me most about this challenge is the vast array of talent that we have in our Design guild and knowing how seamlessly my team works together with Product Thinkers in Connected’s other guilds. The reality is that the definition of better products will have shifted as a result of the pandemic, but how you build them is still the same: you assemble a team of smart, kind, and reliable people who are guided and empowered by a shared mission. Knowing that’s what we do, and will continue to do every day at Connected, makes this strange and challenging year of my career worthwhile.