How to Collaborate Remotely (and Never Sit in a Cold Meeting Room Again)

Woman looking at phone with laptop
Jesse Stewart

UX Development Manager

Jesse Stewart

This post was written in collaboration with David Luhr.

One of the rumors about working remotely is that you’re not able to collaborate as effectively as if you were co-located. How will you draw on a whiteboard together? Or ensure that folks are paying attention?

Not only is it possible to collaborate remotely, we believe that remote collaboration is more effective than collaboration in an office setting. You’re able to get the best of both worlds: collaboration that feels organic and intentional, getting to work in your ideal space with your preferred set up, and less friction involved with setting up a session (gone are the days of trying to find a too-cold meeting room). This makes it easier to get into a flow state and get things done. We’ve worked together for about two years and have found remote collaboration happens in two big ways: working sessions and async (in a written format, usually over Slack).

Down with Meetings, Up with Working Sessions

Notice how we use the word “session” instead of “meeting.” This is key, and is more than just word choice. Effective remote collaboration is all about moving beyond agendas, updates, and action items. Instead of getting stuck in planning mode and relying on time outside of meetings to do the actual work, ditch the meeting in favor of working sessions.

So pick a block of time to do high caliber, focused work together, and resist the urge to have a meeting about it. Trust that you can create a productive space for remote collaboration, and the work will get done twice as fast by simply working together from the start. The first session or two may take some adjustment but will save time and effort in getting projects done together.

Alright, you scheduled a working session with a colleague and now you’ve both joined. It’s time to work, so catch up and talk through what you’d like to get done, but once the work starts, be comfortable not filling every moment with conversation. If you’re used to having meetings all the time, there’s an urge to constantly talk to each other, because that feels like a productive meeting. However, these working sessions are all about getting into that elusive flow state and achieving this focus together.

Imagine you’re working alongside your colleague in an office. You would organically fall in and out of conversation as needed to get work done, leaving periods of quiet for heads-down work and then turning to each other to ask a question or talk through a tricky problem. In a remote session, it can initially feel like you’re acting or mimicking the role of “productive coworkers in an office,” but you quickly get comfortable and switch from solo work to remote collaboration with ease.

In our remote working session, we find that unmuting on a call to ask a question can be a little jarring (especially if the other person is listening to music or is deeply focused), so instead we paste the raised hand emoji (✋) in our call’s chat. This also allows the other person to only switch focus back to the call when they’re at a good stopping place, which helps eliminate disruptive distractions.

We’ve been collaborating for a while, and after incorporating remote working sessions, we’ve done them so frequently that they feel like a natural extension of our day. We’ve used them to work together on client consulting projects, collaborate on internal projects, create conference talks, and now we use them to co-manage the stellar UX Development team at DockYard. Over time, we’ve found these processes work best for us to actually get work done and not just talk about getting work done. We’re always pleased at how productive these sessions are.

It’s important to note that this collaboration even worked as our working relationship evolved. We started out as individual contributors and peers on consulting work. Then, Jesse was promoted to UX Development Manager, and David became her direct report, but the working sessions proved invaluable to getting things done together instead of merely delegating. Now, both Jesse and David are co-managers, and the investments we made into this process keeps providing more and more value. Reflecting on this experience, we strongly believe more managers should collaborate with team members to solve problems for clients, instead of all conversations being agenda- or update-driven meetings.

How We’ve Used Working Sessions

Our working sessions cover a lot of ground and often flow organically from one type of work to another. This is a major strength over holding meetings. We’re not afraid to plan for five minutes and then immediately dive into quiet time as we write, design, or code together.

Pair Planning, Ideation, and Whiteboarding

Even though we ditch the meeting format, we still plan and ideate together. But, the critical difference is that this is often rapid and immediately followed by actually doing the work we’ve planned or outlined.

To help us remotely plan, we make heavy use of Google Docs for writing outlines and taking notes. We create tasks or cards in Asana to make sure we don’t lose sight of action items. This also gives an outlet for new ideas or unrelated work that’s outside the scope of our working session. We’ve even used drawing tools like InVision Freehand to achieve true designer-developer collaboration on consulting projects, where both disciplines are on the same call, sketching and talking through features and UI together.

Pair Writing

One thing we do frequently is pair writing. After we outline a conference proposal or script, or messages for which we need to get the communication correct — even this blog post — we spend time together on a call writing. Teams often stop at the outline and assignment stage of writing, but we’ve found that if we put ourselves on mute and work in a shared Google Doc, we’re able to get so much done in a short amount of time. We’ll read things back to each other on the call, see if anything feels clunky, and revise from there.

Pair Designing

With the rise of screensharing and real-time digital design tools such as Figma, designing together remotely has never been easier. While working on a conference talk, we spent hours in Figma together designing an example project and our conference slides. By being in the same session, we were able to naturally switch between creating design iterations and making suggestions or talking through tricky design problems. No waterfalls or design reviews in sight.

Pair Programming

Since becoming managers, we don’t pair program anymore. When we worked together on client projects and internal projects we paired regularly with both UX Developers and engineers.

Typically, different development teams formally hand off work, and have to rely on TODO comments or clear communication to work on a complex feature together. We found a lot of value in directly working on the same code in real time. Some of David’s favorite client work was made possible by spinning up a VSCode Liveshare session with Sarah Canieso, who’s an Engineer at DockYard. David worked on the markup, styling, and accessibility of the feature, while Sarah handled the data and functionality.

Working Sessions Are More Than Just Work

Working sessions provide dedicated time to be productive, but they also create space for you to interact with your coworkers and clients in meaningful ways, much like catching up in a physical office.

Create Space for Good Conversation

We often start our working sessions with a “life standup” to see how things are going outside of work. We talk about home renos, hobbies, and of course adorable puppers. These standups mimic conversations that we would have in a co-located office environment, which can be difficult to fit in when working remotely. We’re more than just our titles and the work that we do, so it’s good to know a little about the folks with whom you work, especially those with whom you work closely.

Make the Session a Jam Session

When we’re on mute and getting into the flow state with the task at hand, sometimes we’ll spin up a session on JQBX (an online jukebox that DockYarders use regularly). This keeps things from being too quiet and helps recreate the experience of working together in a coffee shop, for example. It’s good background noise and a way to connect with coworkers on something beyond work.

Collaborate Asynchronously

Working sessions are great, but they aren’t the only way to get remote work done. Between different schedules, projects, and responsibilities, it’s hard to get everything done together at the same time.

Since we work in different timezones, we leverage Slack threads in our DM for async collaboration. We use these for tasks that we need to have conversations about that aren’t urgent enough to warrant getting on a call. This also allows us to contribute when we can if we are in the zone working on something else, in meetings, etc. We put topics in bold and usually add a related emoji. All of the related conversation is kept in a thread. When we’ve resolved the topic, we add a medal emoji to the thread to indicate that we’re finished with the conversation and all action items are complete.

Examples of organized Slack threads with emojis to mark completed conversations

Putting It All Together

Now, time for an example of how we used all these approaches to crush a big project: a co-presented conference talk. In the late spring, we were accepted to present our talk, Building Accessibility Together, in August at Abstractions II Conference in Pittsburgh. Faced with the monumental task of submitting a proposal, creating an example project, designing our presentation, writing scripts, and rehearsing, we relied heavily on regularly scheduled remote working sessions to stay on track and create something of which we’re truly proud.

Looking at the conference date, we worked backwards to schedule protected times on our calendars months in advance. With weekly sessions in place, we quickly began workshopping the topic, approach, flow, and outline of our presentation, making heavy use of Google Docs. We then began pair designing an example project in Figma that our talk uses to teach accessibility best practices.

Once the design was ready for development, we paired to code the example project and peer reviewed to ensure it met our quality standards and had all accessibility considerations in place. Lastly, we did automated and manual accessibility testing with audits and screen readers, sharing results, and refining the project further.

With our example project completed, we went back to Figma to design the presentation itself, rapidly laying out the various sections and slides based on our original outline. With the presentation slides designed, we went back to Google Docs to write the script, and then used later working sessions to do full rehearsals of the talk while refining things further.

Throughout these sessions, we made heavy use of JQBX to set the mood with albums we wanted to share, and spent the majority of our time together in the flow state. Without dedicated working sessions, there’s no way we could have achieved all this work on-schedule and or with nearly as much coordination and seamless collaboration. In the end, we were prepared with time to spare, and felt confident when it came time to step on stage for our presentation.

Schedule Your Own

The next time you have a complex task or big project within your team, try scheduling a working session instead of a meeting. It’ll take some getting used to, but once you and your collaborators get in the groove, you’ll be able to enjoy all the benefits of being co-located, while sitting cozily in your ideal remote working environment. Start up some async Slack threads, catch up on life, put on some good music, and dive into that flow state together with the best form of remote collaboration.

DockYard is a digital product agency offering custom software, mobile, and web application development consulting. We provide exceptional professional services in strategy, user experience, design, and full stack engineering using Ember.js, React.js, Elixir, and other tools. With staff nationwide, we’ve got consultants in key markets across the United States, including San Francisco, San Diego, L.A., Phoenix, Dallas, Detroit, Miami, Pittsburgh, Baltimore, and New York.


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