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Managing a remote team

Planted 02020-09-21

How to manage and work with a remote team.

The four time buckets of managers:

  • Information gathering
  • Decision making
  • Nudging
  • Being a role model

In your first 30 days, try to understand the landscape:

  • Where is my team going? What’s our vision?
  • Where is my team now?
  • What are our challenges?
  • Who are the people I’ll work with?

The Remote Office

  • Synchronous communication: Chat tools (Slack) enable a constant, real-time connection with your team.
  • Digital workspace: A place where you have full access to project progress and assignments of who’s doing what.
  • Video meeting space: Video tools (Zoom) give your team face time together.
  • Open document storage: Give everyone access to files they need with cloud-based shared document spaces (Dropbox, Google Drive, Confluence).
  • Team Calendar: A team calendar shows vacation and holidays, important launches and due dates, and shared meetings so you can visually see everyone’s availability.

Document how tools are used and where to go with questions.

It’s the leaders role to:

  • Articulate unarguable goals and aspirations and why
  • Clearly define roles and responsibilities
  • Hire only people important to the business
  • Ensure important people can do important work
    • Ensure deep work over shallow work
    • Take away barriers
    • Get out of the way and let them do their job
  • Ensure better communication
    • Because poor communication creates more work
    • Because poor communication degrades dignity and respect

Defining the work experience

  • People find projects they can make impactful contributions to
  • People find projects they can learn from contributing
  • Working on the team or on projects are meaningful to people
  • People feel a strong sense of belonging to the team or on the project
  • People identify with the mission and purpose of the team or project
  • People care about the future of the team or project
  • People strongly identify with the organization
  • Contributions are valued in the organization
  • Conflicts are resolved quickly within the team
  • Information is actively sought on the team
  • Responsibilities are shared on the team
  • Cross-functional collaboration is encouraged and rewarded on the team
  • Failure causes productive inquiry on the team
  • New ideas are welcomed on the team
  • Documentation explicitly states who has the authority to perform certain tasks
  • Documentation explicitly states who has influence over decisions
  • Documentation explicitly states how to gain authority, influence, or rank
  • People are interested in mentoring others
  • People who want mentorship can get it
  • The team explicitly offers mentorship to new hires
  • Everyone has a voice
  • When contributions are rejected, the rejection is explained
  • People assume the best about each other
  • People provide constructive feedback
  • People are thanked for their contributions
  • Problematic behavior is addressed in a timely manner
  • Problematic behavior is addressed fairly
  • People have the tools they need to do their job
  • People use personal judgement in carrying out their work
  • People understand what the intended purpose of their work
  • New contributors or new hires can easily find solutions
  • It is obvious where to go for help
  • It is obvious where to ask questions


  • Documentation gives an example of how to use the code
  • Projects have READMEs that describe why the project exists or what problem it solves
  • READMEs provide install or setup instructions
  • There are clearly identified issues that are good for new contributors or new hires
  • Documentation uses language that is clear and accessible to new contributors/new hires and non-native speakers
  • Documentation is updated when the code changes
  • Each commit changes just one thing

Optimize for Deep Work

Deep Work: Professional activities performed in a state of distraction-free concentration that push your cognitive capabilities to their limit. These efforts create new value, improve your skill, and are hard to replicate.

Shallow Work: Noncognitively demanding, logistical-style tasks, often performed while distracted. These efforts tend to not create much new value in the world and are easy to replicate.

The reach the optimal state of deep work you need to work for extended periods with full concentration on a single task free from distraction. Organizational leaders must ensure people can do important work, ensure deep work over shallow work, and take away barriers to achieving deep work. Protect your team from distractions.

The most common barrier to deep work: distraction. The most common distraction: chat.

Chat is good for:

  1. Quickly tossing an idea back and forth
  2. Alerting people of time-critical information
  3. A sense of belonging

Chat attacks attention and severely hinders deep work:

  1. Mental fatigue and exhaustion
  2. An unsustainable ASAP culture
  3. Fear of missing out or not having a say
  4. Thinking a line at a time rather than a thought at a time
  5. Implied consensus
  6. Knee-jerk responses
  7. Over-informing everyone in real-time
  8. Shallow work
  9. Lack of context

Other barriers to deep work:

  • Shallow work
  • “multitasking”
  • Literally anything that grabs your attention during your work that is not your work
  • Not completely shutting down work thinking at the end of the workday

Establish Group Norms

Group norms are informal and formal rules of how people interact. Group norms clarify roles and provide a sense of predictability.

Document shared expectations explicitly.

Meeting Norms

  • No agenda, no meeting
  • We circulate meeting agendas at least 24 hours before meetings
  • At the start of the meeting, everyone reads the document
  • We begin and end meetings on time
  • We discuss problems directly, focusing on solutions rather than blame
  • We are engaged and present in meetings
  • If there is a reason we need to be less present, we communicate that to the group at the beginning of the meeting

Communication Norms

  • Meetings are the last resort, not the first option
  • Speaking only helps who’s in the room, writing helps everyone
  • Substantial decisions start and end with an exchange of complete thoughts, not one-line-at-a-time jousts. Write it up, don’t chat it down.
  • Use threads
  • Use @ if you want someone to read a message
  • Over communicate: poor communication creates more work
  • Document things people also need to know and where the communication happens.
  • Never expect or require an immediate response. Urgency is overrated, ASAP is poison.
  • Communication shouldn’t require schedule synchronization. Calendars have nothing to do with communication. Model, document, and share.

The following is a summary of the Know Your Team Intro: Managing Remote Teams.

When you’re a remote leader, you can’t afford to not be a good writer. You can’t afford to not be intentional about social connection. You can’t afford to not trust your employees.

1. Switch from “Speak first” to “Write first.”

When you have a question, the instinct is to talk to someone about it – not write it out. When you have a new project to kick off, you hold an in-person meeting. When you have a question, you walk over to someone’s desk to ask them about it. However, in remote teams you don’t say it, you write it.

2. Trust your employees

It doesn’t matter how many hours are being put into the work or when the work is being put in. All that matters are the results — and I trust our employees find a way to make the results happen.

3. Foster connection (belonging cues)

Belonging cues have to do not with character or discipline but with building an environment that answers basic questions: Are we connected? Do we share a future? Are we safe?

From The Culture Code by Daniel Coyle:

One misconception about highly successful cultures is that they are happy, lighthearted places. This is mostly not the case. They are energized and engaged, but at their core their members are oriented less around achieving happiness than around solving hard problems together. This task involves many moments of high-candor feedback, uncomfortable truth-telling, when they confront the gap between where the group is, and where it ought to be.

Flip meetings

  1. Meeting time should be reserved for meaningful interaction, not conveying information.
  2. No one should feel obliged to attend a meeting where their active participation isn’t needed.
  3. Meetings should be limited to fewer than eight people — the upper limit beyond which meaningful participation falls off and people become more guarded and less candid. Five or fewer is even better.
  4. Outcomes should always be documented afterward for people who couldn’t or didn’t need to attend.

The Basecamp Guide to Internal Communication

The following is a paraphrased and quoted section from The Basecamp Guide to Internal Communication.

They aren’t requirements, but they serve to create boundaries and shared practices to draw upon when we do the one thing that affects everything else we do: communicate.

Rules of thumb, and general philosophy

  1. You can not not communicate. Not discussing the elephant in the room is communicating. Few things are as important to study, practice, and perfect as clear communication.
  2. Asynchronous over real-time. Real-time should never be the first option.
  3. Long-form writing over verbal. Reduces opportunities to interrupt and be interrupted.
  4. Meaningful discussions need time to develop and unfold. Rushing to judgement, or demanding immediate responses, increases the odds of poor decision making.
  5. Meetings are a last resort. Meetings should never be the first option.
  6. If it’s important, critical, or fundamental, write it up, don’t chat it down. Meaningful decisions start and end with an exchange of complete thoughts, not one-line-at-a-time jousts.
  7. Speaking only helps who’s in the room, writing helps everyone. This includes people who couldn’t make it, or future employees who join years from now.
  8. If your words can be perceived in different ways, they’ll be understood in the way which does the most harm.
  9. Never expect or require someone to get back to you immediately. Unless it’s a true emergency. The expectation of immediate response is toxic.
  10. If you have to repeat yourself, you weren’t clear enough the first time. However, if you’re talking about something brand new, you may have to repeat yourself for years before you’re heard. Pick your repeats wisely.
  11. Poor communication creates more work.
  12. Communication isn’t a problem, its miscommunication. The smaller the company, group, or team, the fewer opportunities for miscommunication.
  13. Five people in a room for an hour is a five hour meeting. Be mindful of the tradeoffs.
  14. Give factual and spacial context. Factual are the things people also need to know. Spacial is where the communication happens (for example, if it’s about a specific to-do, discuss it right under the to-do, not somewhere else).
  15. Communication shouldn’t require schedule synchronization. Calendars have nothing to do with communication. Writing, rather than speaking or meeting, is independent of schedule and far more direct.
  16. Let whatever you have to say filter through time. What’s left is the part worth saying.
  17. Will others feel compelled to rush their response if you rush your approach?
  18. If you aren’t sure, sleep on it before saying it.
  19. If you want an answer, you have to ask a question. People typically have a lot to say, but they’ll volunteer little. Automatic questions on a regular schedule help people practice sharing, writing, and communicating.
  20. Delete words, sentences, or paragraphs and ask, Did it matter?
  21. Urgency is overrated, ASAP is poison.
  22. If something’s going to be difficult to hear or share, invite questions at the end. Ending without the invitation will lead to public silence but private conjecture. This is where rumors breed.
  23. Where you put something, and what you call it, matters. When titling something, lead with the most important information. Many technical systems truncate long text or titles.
  24. There may not be a perfect time, but there’s certainly a wrong time. Sharing something at 5pm may keep someone at work longer. Early Monday morning communication may be buried by other things.
  25. Great news delivered on the heels of bad news makes both bits worse. The bad news feels like it’s being buried, the good news feels like it’s being injected to change the mood. Be honest with each by giving them adequate space.
  26. Time is on your side, rushing makes conversations worse.
  27. Communicate directly rather than through intermediaries. Communication is lossy, especially verbal communication. Every hearsay hop adds static and chips at fidelity.
  28. Address the gaps before they widen with time. Ask if things are clear. Ask what you left out. Ask if there was anything someone was expecting that you didn’t cover.
  29. The right communication in the wrong place might as well not exist at all. When someone relies on search to find something it’s often because it wasn’t where they expected something to be.
  30. Good communication is about saying the right thing at the right time in the right way with the fewest side effects.

Switch “How’s everything going?” with “What’s one thing that could be better?”. This is the difference between being open to feedback and seeking feedback.

It is normal for me to take 2 days to read my emails and 2 more days to reflect on the matter and respond calmly. The culture of immediacy and the constant fragmentation of time are not very compatible with the kind of life I lead.