Lessons from Seven Years of Managing Async-First Remote Teams

An increasing number of teams are transitioning to remote, async-first ways of working. Async-first work brings a lot of positives, but it's not without challenges that can cause a loss of context and speed. This post outlines proven practices related to managing relationships with your reports, building a robust internal network, advocating for org-wide changes, and keeping your team's execution velocity high in a remote environment. Adopting them can help you thrive as a team lead in any async-first company.

As a team lead, evolving how you manage relationships with reports to account for the specifics of async creates a more aligned and motivated team. But relationships don't stop with direct reports. Keeping a broader internal network gives you the needed context to shape your roadmap. It also helps you identify org-wide pain points and create guiding coalitions for change. Lastly, you might need to optimize your team's operations to continue executing at high velocity in an environment where daily standups are not a practical option.

Adopting Relationships with Reports

1:1s are king.

1:1s are the most critical tool for evolving relationships with your reports, understanding their needs, and helping them grow.

In a typical async setup, face-to-face time is limited between you and your report. Extracting the maximum value from each 1:1 is therefore essential.

Show up prepared.

1:1s vary based on your report's preferences and overall dynamics, but one element is consistent. Both you and your report should be preparing for 1:1s. Ask your report to brainstorm topic ideas for each 1:1 and do the same. Sometimes the agenda will be light, but if you have consistent difficulty coming up with topics to discuss, it's a yellow flag that alignment or motivation issues lurk beneath the surface.

Don't cancel.

In some cases, your report will argue that you discussed all feedback and topics as they arise. They will try to seduce you to cancel the 1:1. Don't bite. No agenda is an excellent opportunity to catch up and discuss lingering topics on your report's mind, but they can't fully verbalize them. A bit of uncomfortable silence is your friend.

Experiment with the format.

Each report is different. Some like structured 1:1 formats following techniques like start-stop-continue. Others prefer to freestyle it. Iterate the format together to get the most value out of it. The goal should always be to place the responsibility for the 1:1 with your report and ask them to drive it. If your report takes charge of your time together, prepares topics, and injects energy, it's proof they are highly motivated and want to keep improving.

Share context.

Async-first companies tend towards silos. 1:1s are an opportunity to share context around broader organizational initiatives influencing the report and point them towards internal networking opportunities. Each person is curious about different parts of the organization, making 1:1s a great place to provide a tailored message.

Be vulnerable.

Lastly, prepare to show vulnerability and share a few bits from your personal life. Not everyone values a personal touch in their working relationships, but many people find it meaningful as a way to connect to their manager and feel supported. In remote, opportunities to connect on a human level are rare, so being able to listen to your report's troubles and share back is a powerful tool to deepen a lasting relationship built on trust.

Keeping a Healthy Internal Network

1:1s are still king.

Similar to relationships within the team, 1:1s are the most powerful tool in your toolbox. While many tools trying to automate internal networking like Donut are cropping up, leveraging them to build long-lasting relationships that are useful beyond the social aspect is hard.

Curate.

Maintaining a network is challenging, especially with people with whom you don't collaborate directly. But, connections from outside your context will be some of the most valuable ones you can form. Discussing daily challenges with people from faraway teams builds intuition about fires that trouble the entire organization and where your energy has the most potential to create impact. Identify your biggest blindspots within the organization structure and find like-minded souls within them.

Once you identify the victims of your networking efforts, invite them for a short 1:1. Within it, evaluate the personality fit and whether you can provide value to your potential connection. If you agree there is a fit, schedule a repeating monthly or quarterly 1:1. All of the tips from 1:1s with your team apply here. Showing prepared, experimenting with the format, and being able to show vulnerability go a long way towards building a joyful relationship.

Keep tabs on dependencies.

Beyond building a broad view of the organization through a diverse network of connections, pay special attention to the teams that form your dependencies. Upstream technical partners or teams generating your work are a few examples of such teams.

A close partnership with the leadership of those teams is a given. Outside of that, building relationships with a few other people within teams you depend on will grant you the ability to remove the fog of war and consistently predict your team's future. While discussing high-level planning is critical, getting an unfiltered view from the people on the front lines fills in your awareness gaps. This additional context will be highly actionable as a tool for de-risking your team's roadmap and brainstorming backups in case things go sideways. Let the team lead of the person you intend to network with know your intentions. Otherwise, they can be caught off-guard, undermining their trust in you.

Advocating for Org Changes

It's time to leverage the context and partnerships you've built to pick an org-wide problem and advocate for change.

Optimize for skimming.

For advocating org-wide changes, mastering your written communication style is vital. In async-first companies, whether using Twist, Threads, or Slack, the firehose of written content never stops. To counter the overwhelming pace of new content, people skim heavily and stop reading mid-way through if the content isn't engaging.

You need to optimize for the limited attention of your colleagues if you want your ideas to break through. Learn the Pyramid Principle. Leverage lessons from military communication. Write one sentence per line. Use Grammarly or LanguageTool and take time to understand the style suggestions.

Try as many writing frameworks, tips, and tools as possible, and find how to meld them with your style. If you stay intentional about improving, you will see tangible improvements in the engagement you get on your content.

Embrace the jargon.

Each company has its jargon. The leaders of industries heavily inspire some companies, like the recent popularity of squads, tribes, and chapters, introduced by Spotify. Other companies revel in impenetrable acronyms.

Aside from acronyms, there are also shortcuts for specific behaviors, processes, or goals, such as providing radical candor or getting the flywheel going.

Don't resist.

By leveraging internal jargon, you create tripwires in your writing that catch the reader's attention, slow them down, and activate their curiosity. You shouldn't pack your writing full of buzzwords, but leveraging the right word or phrase at the right time makes your content feel more relevant.

Communication within async-first companies can resemble the joys and pains of social media. Approach your internal writing with the same assumption that it needs to be exciting to make it more likely your idea will catch traction.

Understand organizational appetite for risk.

Organizational appetite for risk exists on a spectrum.

On one side is kaizen, the approach of implementing bite-sized improvements continuously. The other is the 10x approach, where fewer but more disruptive changes are preferred.

Understand your company's appetite for risk and align with it. Spending energy on advocating for incremental changes in a company that focuses on 10x-style changes and vice versa is rarely a good use of energy. If your organization is well aligned, you can understand the type of idea the company is looking for by researching what changes the leadership tends to sponsor.

Execute at High Velocity

All the tips above are only helpful if you can maintain your team's performance within its core scope. Aside from finding ways to make your core workflows work within async, a topic for a separate post, there are several considerations for positioning your team within the broader organization.

Formalize your team's interface.

Clean interfaces within teams help eliminate the need for ad-hoc behaviors, which are hard to achieve within async-first environments. How can other teams give you new work? How do you communicate progress? What are the places to give you feedback? Who should people tag for specific concerns? Write a spec of your team interface that answers these questions. If you get recurring questions related to interacting with your team, add them to the spec.

When designing your team's interface, ensure it exposes only essential complexity and hides the accidental complexity of your team process from the rest of the company. This will make it easier for others to interact with your team and give you the freedom to iterate how your team works, as long as you uphold the same clean interface.

Make sure your team's interface is stable over time. Stability creates consistency for the teams around you and builds trust.

Worship Conway.

In async-first companies more than in others, Conway's Law always gets its way. With fewer casual relationships between teams, silos form frequently, and collaboration across teams can be challenging due to the slower communication loops inherent to async.

First, understand the dependencies of your team's scope. Build connections with those teams' leaders and team members. Once you understand the other teams' context, you can identify friction points and work them. Removing friction points can take many forms, from transferring ownership of components to creating explicit contracts between teams to improve accountability.

Start Small

Async can be overwhelming, whether your current company is transitioning into it or you're joining your first async company. It's normal to take several years to get fully used to this radically new way of working. Don't try to change everything at once, but start small, build confidence, and go from there. Organization context always trumps generic advice, so starting by discussing the challenges with your existing network is a great way to get going.

If you have no one who can help within your network, use the async topic as an excuse to bootstrap new connections within your company! If that doesn't feel like an option, ping me on Twitter @jankratochvilcz, and I'll be happy to chat. πŸ™‹β€β™‚οΈ


The above represents my personal experience; a few caveats apply.

  • The techniques above worked well for me in a primarily meritocratic setting. I suspect they may be less effective at companies with a proceduralist worldview. See Meritocrats and Proceduralists.
  • I have been lucky to have bosses who have consistently provided me with sponsorship and trust to take actions I feel are in the company's best interest.

Cover photo by Photo by Avi Richards on Unsplash.

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