Asynchronous Communication & The Remote Workplace

Remote workplaces are rapidly becoming commonplace. Founders are recognizing that many of the historical strengths of physically co-located offices no longer hold true, particularly given the rise of compelling synchronous communication tools like Slack, Zoom, and others. While these products have bridged the gap of “face-to-face” time, many remote workers still struggle with what happens once someone is away from their desk. This is especially prevalent companies that support time zone diversity, either through their hiring practices or through flexibility provided to their team members.

To some extent, many of these problems exist, in their own form, in traditional office environments. The technology that serves as the backbone of the remote workplace has enabled us to address these issues like never before, and we owe it to ourselves, or organizations, and our colleagues to develop, implement, and integrate solutions that maximize this potential.

I had the fortune of beginning my career at Automattic, the creator of and one of the earliest supporters of the “deliberately distributed” philosophy. Automattic, not unlike many non-remote companies, does its best to eschew email to the greatest extent possible. Early on, it recognized the importance of a persistent, open platform for communication between employees, and built its own internal messaging system, called P2, to address this. Automattic leaned into this philosophy very heavily, and the vast majority of P2s within the organization are accessible to any employee — including P2s for each team, and many operationally-focused P2s. Employees are encouraged to contribute to any conversation where they feel their insight may be valuable. During my tenure there, it was not unusual to see folks from every team weighing in during discussions of financials and product strategy. It’s a very unique — and especially productive — environment.

While Automattic has made P2 publicly available for some time, and briefly attempted to productize its successor, O2, these platforms have never gained traction outside of Automattic. This isn’t surprising — much of the rich functionality that made P2 so successful at Automattic is missing from its public-facing releases, including tagging/notifications, cross-posting, support for multiple P2s (Automattic, for quite awhile, had more P2 instances than employees) and faceted cross-P2 posting. Even still, the success of many of these features has highlighted the shortcomings of many remote organization’s approach to asynchronous conversations, and has led me to develop 5 philosophies for addressing these concerns within my own communications at 10up, my current (fully distributed) employer. If you’re starting a remote organization, or considering a role at one, I implore you to consider your own organization’s solutions to these challenges, and work to adapt your communication style to address them to the greatest extent possible. This is, to some extent, thinking out loud — there aren’t many great end-to-end solutions for these problems today, and an enterprise entrepreneur could do well in creating them.

1. Default to Open

You may be familiar with Ray Dalio, founder of Bridgewater Associates, and vehement advocate of a practice that he calls “radical transparency”. In this philosophy (detailed in his book Principles, amongst other places), he notes that Bridgewater has the unique practice of recording nearly every single meeting — regardless of topic and audience size — and making these recordings accessible to every employee in the company. Dalio feels very strongly that conversations, decisions, and debates are at their best when individuals from diverse backgrounds and positions within the organization have the opportunity to participate in them, challenge them, and share their input. In fact, he goes as far as declaring that every conversation within an organization should be treated with this attitude unless legally or morally prohibited (e.g. sensitive personnel conversations, M&A or investment decisions that may violate insider trading regulations).

I believe that this is especially true in remote organizations. By losing the proximity of an office space, you lose out on many opportunities to “overhear” a discussion that you may be well-fit to contribute to — whether that be literal overhearing or through the casual office chit-chat that tends to be less infrequent in remote entities. While the “not their problem” attitude is common in many companies (why should a junior engineer care about our financial forecasting and hiring plans?), the reality is — especially at small companies — that everything is everyone’s problem; it’s just some people’s problem more than others.

By defaulting to communication channels that are open and accessible to everyone, you provide the entire organization with the opportunity to contribute their unique and diverse viewpoints, and empower those who may not traditionally hold roles that are often “at the table” for these conversations.

This maxim also eliminates one of the most common “solutions” to asynchronous communication that I see at many companies — email. Email is not an effective tool for asynchronous communication in a remote workplace. It’s siloed, easy to ignore, and often serves as a distraction for many throughout their day. While it does serve its value — perhaps for private conversations that aren’t suitable for this kind of treatment, and for occasional communication with those outside of your organization (hiring, contracting, etc.) — heavily reliance on it as a platform for internal communication is typically a symptom of a worrying organization-wide asynchronous communication problem.

2. Overcommunicate

Nobody can read minds. And, in many remote work environments, nobody can read emotions, cyclical mood fluctuations, or a number of other clues that can add context to conversations and help others best support you in the workplace and successfully engage in conversations.

In remote workplaces, it’s better to risk telling people what they already know than risk them never finding out. At Automattic, nearly every decision — however major — was documented via P2 (including those that were made during synchronous conversations through other tools, like Slack or video calls). In addition to these decisions, team members regularly communicated their off days, when they were feeling under productive, or when they needed additional support. Within Automattic’s culture, these were seen as positive communications. These are opportunities to support your colleagues and reminders when you might be called to “fill in the gaps”.

Generally speaking, it’s best to communicate anything that you think someone — even one individual — might not know, or might need to know at some point in the future. This gives others the opportunity to support and contribute (including those whom you may not have originally considered — see point one).

3. Engage Others

Automattic’s P2 had a nifty piece of functionality called cross-posting. When posting on a particular P2, you could tag any employee at the company — using the traditional `@` sign syntax — or use a hashtag to cross-post the entire message to another P2. This worked as a signal booster to help potentially interested audiences discover conversations were they may want to follow along, or even contribute.

By viewing the participation of others within conversations as a positive action, and seeking opportunities to invite others to do so, you ensure that diverse viewpoints have had the opportunity to pick apart your thoughts and share their own. Seeing a theme here?

4. You’ll Never Remember a Synchronous Conversation

A quick Slack message is far easier to write than an asynchronously-oriented post with proper supporting context. It’s also far easier to forget.

I prefer to treat Slack as a todo list and as an alternative to a synchronous conversation via phone or video call. If something comes up that can’t be tackled immediately, it should be documented in a written form that’s meant for asynchronous follow-up. If a decision isn’t able to be made during a Slack conversation, it should be completed (with proper context) in a written form that’s meant for asynchronous follow-up. And, if a decision is made, it should be documented — again, with proper context; thankfully, you can link to particular places in Slack conversations — in a written form that’s meant for asynchronous follow-up.

You — and your colleagues — will thank you three months from now.

5. Remember the Past

Now that you’ve built all of these great habits, you need to make sure that they continue to benefit you in the future, just as they’ll benefit you today. Effective tools for searching historical conversations and promoting visibility of important, current-day conversations are essential for the health of remote organizations. Many of the shortcomings I’ve found in tools that are purported to solve these issues, like Facebook for Work, come in discoverability and searchability — unless you happen to stumble upon or remember a conversation, it’s as good as gone. If remote work places are to become an effective replacement to traditional office environments, this needs to be solved.

Unfortunately, I’ve yet to see a startup working to engage asynchronous communication in the way that Slack has worked to dominate the synchronous portion of the channel. Some business-centric tools like Yammer and Facebook for Work (one could also make a case for JIRA, through Confluence) have attempted to add messaging components, but have done so in haphazard ways that only provide an alternative channel for ephemeral, siloed conversations. If you’re aware of a tool that scratches some of these itches — or, perhaps, are building one yourself — I’d love to hear from you.