An abstract image of a pair of people amid a sea of ideas and notes.
Illustration by Marina Verdu.

How to use design pairing to gain crucial context

Pairing is an essential skill when you’re working remotely

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I joined the Shopify Fulfillment Network team on an interesting day — March 16 of 2020, the first day of the new digital by default reality for everyone at Shopify. Up until last year, being able to collaborate face-to-face in the same location was non-negotiable for me.

As I worked my way through the onboarding sessions and training, I kept being reminded of the importance of having the right context, particularly at a large organization like Shopify.

Throughout my career, I’d believed that teams had to be in the same room to be effective and efficient. I was sure that co-location was crucial for a team to gather and share context, empowering them to make decisions quickly.

After onboarding, once I was done with the casual one-on-ones to meet the rest of the team, my projects defined who I would meet. Since I focus mainly on inventory, I met everyone working on anything related to inventory. I became one of the go-to designers in Shopify Fulfillment Network for my inventory context. I felt like I was in a good place in terms of context gathering. But as I became an expert in my area, I noticed my projects had some pretty major blind spots. In some cases, a feature I would be designing would be made irrelevant by an update to another part of the Shopify Fulfillment Network experience, or worse, a problem my team solved caused several other projects to be derailed. Typically, we wouldn’t find out about these changes until our scheduled Fresh Eyes, which resulted in many throw-away mocks, documentation, and work.

A feature I was designing would be made irrelevant by an update to another part of the experience — or worse, a problem my team solved caused several other projects to be derailed.

Fresh Eyes is a meeting where designers and leaders get together to share context and turn proposed concepts into something that works with all the decisions and changes from the past week. Designing became an exhausting exercise of casting a net over my current understanding of a problem, only to find out that the problem went somewhere else by the time the net landed.

I decided I had to migrate some of my context gathering practices to the digital world. That experimentation led me to digital design pairing.

Design pairing draws inspiration from similar practices in software engineering, specifically the Extreme Programming flavor of Agile. Much like in software development, pairing is organized so that one designer “drives” while the other designer “navigates”.

Here’s how it works

To pair remotely you need a design tool that allows multiple people to edit the same file simultaneously. At Shopify we use Figma.

You need to book 1-2 hours with another designer. Finding the right partner is vital. For some of my projects, I paired with Kazden, because he focuses on internal tools for the folks supporting our fulfillment centers. Pairing with him allows me to incorporate the needs of a different user group into my work.

Once you find a partner, walk them through the designs you’ll be pairing on. Provide as much context as you can: What decisions have led you to the current version? What constraints are you incorporating? This shouldn’t take you more than 10 minutes if you’ve found the right partner.

Now the fun part: set a timer for 5–10 minutes, duplicate your designs, and hand your file over. Your partner will now drive the session. During this time, they will modify your designs. Ask them to articulate everything going through their mind. They should be telling you every micro-decision they’re making and the options they’re considering. You might have to remind them to keep talking. In a recent pairing session, my partner deleted all the components used for configuration. They explained that they were working on a new version of the settings page, and these components would soon have a new home. This interaction took less than 5 minutes, but it saved me several hours of wireframing, documenting, presenting, and eventually getting feedback about the configuration components, which would then result in having to delete them.

While your partner drives, your job is to be quiet and pay close attention to their work. Write down any questions or interesting points that come up so you can clarify them later.

When the time is up, ask those clarifying questions, duplicate their designs, reset the timer, and start driving. While you drive, make sure you build on your partner’s decisions as much as you can (kind of like improv’s, “yes and…”). Avoid selling your direction as the preferred route; instead, focus on building a shared understanding. Allow yourself to be curious and explore directions that you had previously rejected. When your time is up, go over any clarifying questions and swap roles again.

Leave 10–15 minutes at the end of the session to have a short discussion. In the end, you will have a series of iterations on your designs that incorporate constraints and context from a whole other area of the product.

How pairing has helped our team

Our team now uses pairing regularly, which has allowed us to draw some lessons from it.

It reduces waste

Pairing with other designers creates space for real-time feedback and design decisions get validated on the spot. When pairing with designers from different product areas, gaps are quickly identified, which allows us to course-correct immediately. This means less time spent writing documents and specs to communicate with other teams, and more time spent solving problems. Because pairing is a time-boxed activity, we communicate assumptions through words instead of mocks, which are more expensive to produce and hide our thinking behind pictures.

It creates room for feedback

An interesting part of presenting your work in the physical world is the change in perception that happens when you move your work from your desk to a wall or projector screen. That simple transition allows us to set a boundary between ourselves and our work, making us more open to feedback. In the digital by default world, the physical space where we work and share our work is the same. By pairing with other designers, we automatically remove the idea of “I designed” and start viewing our work as “we designed”.

By pairing with other designers, we automatically remove the idea of “I designed” and start viewing our work as “we designed”.

It distributes ownership and makes our team more resilient

Pairing empowers everyone on the team to have enough context on all ongoing projects. Leveling up everyone on the team helps mitigate the single point of failure. The team can continue to be impactful even when that one designer with all the context about a topic goes on vacation.

It increases productivity

Incorporating feedback directly into a design drastically reduces the amount of time it takes to get context and turn it into action (because you’re literally getting context through action), so projects can move forward faster.

It helps designers get better at articulating design decisions

When we go off to design on our own, we engage in a little monologue inside our heads. We make thousands of decisions and micro assumptions on the fly without even noticing, and it becomes hard to articulate them because they just get baked into the designs, within layers and layers of components. Pairing allows another designer to peek into our monologues and challenge those assumptions on the spot, so they don’t make it into our work. With every session, we get a little better at identifying those assumptions.

It accelerates growth

In addition to getting context about different parts of the product, designers can learn new tricks and tools while pairing with more experienced peers. Watching someone else work live also allows you to peek into techniques to organize files or speed up workflows that you would never get otherwise. Teams become empowered to disseminate new procedures and best practices quicker — I can’t tell you how many shortcuts and pieces of prototyping magic I’ve learned through pairing!

It’s been nearly a year since we embarked on this digital by default adventure. Perhaps the most important thing that I’ve learned so far is that we have to be overly explicit about things we used to take for granted. We used to gather and share context through conversations over lunch or coffee, and through all the relationships that started just because we recognized a new face at the office. Digital design pairing has been my overly explicit way of sharing and gathering context from others.

Are you also experimenting with techniques to get context and align with others? Let me know!

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