tips-for-leaders.md

Rethinking async communication: Tips for leaders

Successful remote work requires intentional communication, grounded in the following core principles (fully defined in the "Rethinking async communications" document):

• Be asynchronous first
• Write things down
• Make work visible and overcommunicate
• Prefer tools that capture and expose process
• Embrace collaboration
• Foster a culture that values documentation maintenance
• Communicate openly, honestly, and authentically
  • Strive for inclusivity
  • Use emoji
• Remember practicality beats purity

This document contains a brief set of further expectations for leaders on how to set an example and create an environment on their team(s) that promotes these principles.

Invest in psychological safety

Start here 👆. If there's one thing you can do to strengthen asynchronous practices on your team, it's to be intentional about creating psychological safety. Be open to feedback, admit your mistakes, and show vulnerability. Be open to feedback, admit mistakes, and show vulnerability. When your team feels safe sharing ideas, voicing concerns, and providing feedback without fear of retribution, they’ll be more comfortable working independently, confident in their decisions, and less dependent on waiting for approval. Plus, being open and able to discuss the hard things with each other means we'll always be growing and improving.

Ways to get started:

• Be open about your strengths, preferences, and areas of growth to help your team members feel comfortable being human too. Create a Human User Guide and link to it from your chat or intranet profile, and encourage your team to do the same.
• Prioritize and be fully present in 1:1s, and let your team members drive the agenda (it's their time).
• Write like a human. Be as transparent in communications as possible, and consider creating an FAQ for anticipated questions (remember it's better to say "I don't know" or "I can't answer that right now" than to pretend the question doesn't exist).
• Keep your virtual door open and proactively seek out feedback (e.g., send out congrats messages for big ships when you have a few minutes between meetings; pick a few team members to review comms before sending and implement a change based on their feedback; ask more direct questions 1:1 like "What support would be helpful?" or, "What's the biggest risk I'm not seeing right now?").

Be explicit about expectations

As a team, collaboratively author a set of agreements outlining your agreed-upon working and communication styles, including anticipated response times and preferred channels. This not only ensures everyone is on the same page, but sets a baseline for what's expected of one another – everyone should be clear on what you expect from them, what they can expect from each other, and what they can expect from you. This activity is especially important when spinning up a new team or reorganizing an existing one, but it's also a good practice to periodically revisit these agreements to ensure they continue to reflect the team's shared values and evolving workflows.

Ways to get started:

• Review the "Rethinking async communications" guidance and discuss how the core principles apply to your workflows.
• Talk with your team about the number of standing meetings on their calendars and be explicit about which ones they're expected to attend live and which they can catch up on asynchronously, so they feel more empowered to take control of their time.
• Implement and honor no- and low-meeting days (like no-meeting days or deep-work days/weeks) by rescheduling any non-urgent meetings.
• Agree on and maintain a single source of truth for team decisions (bonus points if it's easy to find and search through).

Optimize for the information retriever

Rather than optimizing for immediate information exchange, pause to ask yourself how easy you are making it for someone to come along behind you to understand what you are doing and why, so they can contribute to the conversation. It's essential that we write things down – especially the "why" and the "how" of decisions – in the most durable, searchable, and discoverable medium possible. This is slightly more work up front for the one knowledge creator, but optimizing for the long-tail of knowledge retrieval will save countless hours for all the knowledge recipients. Think of it kind of like removing an N+1 in a heavily trafficked code path: The initial re-write takes time, but not as much as it saves in the long run.

Ways to get started:

• Build time to update documentation into team work plans (and if a document's maintenance outweighs its benefits, simplify or remove it).
• Block focus time on your calendar for writing and reading so you can preserve synchronous team time for high-impact conversations and informed decision-making.
• Ensure every meeting has an agenda document that's shared ahead of time to collect input from team members who can't attend live, so their voices can be heard during the call (and be sure to post pass-down notes after the call, too!).
• Make any big announcements ahead of (not during) synchronous meetings (this ensures the whole team has access to the announcement, even if they can't attend the call, and they have time to process the information and collect their questions).

Make more of your work visible

The best way to work in the open and to make that work visible is to use tools and workflows that naturally capture and expose process. So embrace your inner engineer and default to working out of the same tool your team is using, whenever possible and practical. By working more in the open, you'll better preserve institutional knowledge, empower others to learn through observation, and set the standard for organizational culture and values. Plus, you'll reduce time spent on status updates, as your team can more easily understand what you're working on and why, plus provide feedback along the way. Of course, there's no need to track every one of your administrative tasks; surface the important work (like decisions where you want input, or longer-running issues for which your team is looking for regular updates).

Ways to get started:

• Set up and maintain a leadership team project board so your team has better insight into what's currently in flight.
• Seek feedback before decisions are made (rather than asking for feedback on a decision); invite collaboration directly on your issues, documents, and pull requests; and document how you incorporate the team's feedback (to show you're willing to act on it, and thus it was worth their time contributing).
• Use queries in your work-tracking tool of choice to automate team status updates and weekly reports as much as possible and free more of everyone's time (if someone's already reported a status on an issue, they shouldn't have to repeat it in chat or in a meeting).
• Share a high-level weekly status report with your team and the broader organization to keep everyone informed, aligned, and aware of potential collaboration points.