Posts categorized as leadership

Remote Communication

Sustainable remote communication requires being intentional and mindful of yours and other’s time.

In distributed companies, we can’t bump into each other in hallways, have casual coffee chats, or even be able to offer a proactive helping hand if a teammate looks confused. Every conversation: be it in video, text chat or private message needs to be initiated by someone with intention.

What we trade for potential increased focus and flexibility, we lose in in-person spontaneity. This isn’t all good or bad, just different. Being mindful of this while we pick the communication tools at our disposal is key to communicating clearly and efficiently.

If you find that you’re constantly task switching, are having endless back-to-back meetings, or are spending all of your time in text chat, this post offers a few things to experiment with and try. 

It’s 2020, so put on your own oxygen mask first 

Before we dive in, I want to acknowledge that there is a pandemic raging, climate change making itself ever present, and all the while, we’re still expected to work. Maybe you’re also struggling with additional caregiver responsibilities, or the social isolation of not being able to go outside and see physically visit people without calculating the risks. 

If this remote stuff feels impossible, know that it isn’t a normal time to be working remotely. Long time remote-first workers are feeling the strain too. Please take care of yourself as best as you can and if you’re a manager reading this post, please encourage folks to take some time off and model that behavior by taking that time off yourself.

Types of Communication Mediums

Long-Form Writing

Long-form writing is the binding glue for most well-functioning remote companies. If you’re ever unsure of a medium to pick it’s hard to go wrong by starting with a long-form post.

A post written by one author can start a conversation in the company with many people and teams. The medium is also flexible enough to handle everything from routine meeting notes and team project questions (working through technical, design or product questions) to a well-honed north-star vision that might guide company direction for the following year.


  • Long-form writing forces the author to stop and take the time to frame their thoughts in a succinct and coherent way.
  • Participants don’t need to drop what they’re doing, right now, to focus on a problem that someone raises. They can instead reply when it’s the best time for them. A response within a business day or so, for example, is more than appropriate. This allows for more experimentation with personal schedules. Many find it more efficient to devote one part of their day to reading and responding to posts.
  • It allows folks who are more time-shifted to catch up with what’s going on. This can especially be helpful if you have colleagues in very distant timezones or are working flexible hours.
  • We can eliminate some meetings and better prepare for the remaining ones.
  • With search, we can find out why things have happened in the past without us being there or relying on imperfect human memory.

What type of problems would we pick long-form writing for? Really, just about everything: from a CEO describing company vision to an individual contributor getting into the weeds and needing to work out a solution with feedback from co-workers. 


  • A group post (written by many people) outlining the north star for company direction 5 years out and a specific roadmap for the quarter. The post asks readers for feedback with a given time deadline, e.g. open for the next 2 weeks.
  • A project lead summarizes the why, the challenges, risks and estimated time for a given project.
  • A designer asks for feedback from the team and stakeholders for the latest flow for their new feature. 
  • A developer outlines two implementation options for the feature and asks for feedback from both product and other developers on tradeoffs and a check in on if they understand requirements.
  • A lead writes up routine team meeting notes: highlighting the agenda, who attended, what was asked, what decisions were made, any follow up action items and who was responsible.

Tool requirements

Roughly, when picking out a specific tool to power internal discussions, it should have the following elements:

  • Posts can notify the right number of people – There should be some ability to tag individuals and larger groups like teams or divisions.
  • Searchable –  letting us find out why things have happened.
  • Editable – Mistakes can be fixed and we can go back to summarize conversations and outcomes at the top of the post, or in a summary comment. For example, if a post asks a question and a direction was picked, we should double-back to edit the post to point out what happened.

Internally at Automattic, we use a tool called P2 to power these discussions. Forum software or wiki tools might also work for you. 

Try this when:

  • You need to collaborate with one or more colleagues.
  • As a first step to see if a problem can be described and next steps can be taken asynchronously, without a meeting.
  • If no other communication medium is a good fit!


Documentation is a specialized form of long-form writing where information remains relevant over time and is often maintained by many people.

Tool requirements

  • Searchable –  Information is easily discoverable by anyone in the company
  • Editable – by many people


  • Company Culture Book
  • Onboarding documentation
  • Team Processes
  • On-Call Runbook

Try this when:

  • Knowledge is buried in someone’s head and only one person knows how to do something
  • Information is repeated, either through video chats, text chats, or in time-sensitive posts
  • A one-time post resonates with your co-workers more than expected

Workflow Specific Tools (Issues/PRs/Figma/etc)

As a company you may already be communicating asynchronously with very specific tools for a given workflow! For example, bug and feature requests may be written in issues, while developers may spend a lot of time pull requests and code reviews (aka asynchronous pair-programming).

Try this when:

  • Tools and workflows are already in place for your team or company

Try switching mediums when:

  • A discussion is going in circles. Some signs of this might look like needing to click to expand to see a full discussion, or seeing two participants rapidly commenting to each other. When this happens it may be the case that folks are accidentally talking past each other. Text chat or video calls/screensharing can convey information more quickly between two individuals and may help clear up any misunderstandings.
  • We need to step back to better frame a problem at a higher level. For example, instead of going back and forth on implementation details in code, we might need to ask if it’s worth building said feature at all. To reach the right folks, writing in long-form is usually a good call.

If people do choose to switch mediums, please remember to follow up with a summary update or comment summarizing what was decided. This helps others understand what was decided without needing to reach out to others synchronously.

Text Chat

Synchronous communication is a bit of a two edged sword. On the one hand it lets you talk with folks right now, which can help greatly when working through problems and building camaraderie on a team. It also means that we may leave out folks who are in different timezones or are working flex hours out of conversations.

For some, text chat can be very distracting and draining. Let’s go over some reasons why this might be so.

  • Are you allowed to mute chat for focus time, or after hours?
  • What is the expected response-time for a ping in a public channel or direct message? Talk with your lead to get a clear understanding! For example, since Automattic has no core working hours, on my team it’s okay to respond within a business day if folks are not online or have muted chat for focus time.
  • If you’re not on-call, how well are you silencing these notifications on personal devices after work?
  • Can private messages be taken to a more public channel instead? Too many private messages can feel like the equivalent of someone stopping by your desk and interrupting you. If the subject isn’t confidential and can be discussed in the open (think projects not feedback), consider moving the conversation to a more public area. This helps gives others visibility of what you are spending your time on. It also avoids ever growing group direct messages where some subset of folks have half of the conversation.
  • If someone asks for non-urgent help and you’re in the middle of something, can you schedule a time to chat in text or video later on the calendar?
  • Don’t force others to read text chat backscroll. If an interesting conversation has occurred, and we’d like to share what was talked about, a long form post summarizing this is much more appropriate than having someone else parse a long-winding conversation.

Try this when:

  • You need a bit more bandwidth to quickly discuss an idea with a few people.
  • Team/co-worker bonding! a.k.a all of the emojis and gifs! ✨

Video Chat/Screen Share

Video chats and screen sharing demand one’s immediate attention. I can juggle a few ongoing text chats, but I can manage only one video call at a time. In return for this demand on our attention, we can share a lot of information in a short period of time.

Try this when:

  • We’re building relationships! 1:1s, the weekly team call, watercooler chats and so on!
  • When we quickly need to build consensus or brainstorm next tasks in meetings.

Video calls, for whatever reason, tend to be more draining than meetings done in person. Except for 1:1s, aim to keep meetings small, short and on point. An hour for example tends to be the maximum limit of focus, no matter how much people would like to pay attention. Team process may need to be altered to help accommodate this additional cost. I’d recommend simplifying process as much as possible, and preferring async over sync when looking at communication options.


Regardless of what medium we pick, remember to communicate regularly and often! While working remotely, we often need to work twice as hard to make sure folks know what we’re accomplishing and when we need help.

Communicating in a sustainable way requires being intentional and mindful of yours and other’s time. If this ever feels draining, try switching mediums or start a discussion with your lead on experimenting further with process. It may make all the difference!


Three Important Things

Congratulations! You are in a new management role. Now what?

Remember these three things: don’t fall into the safety of your old job, listen, and provide useful feedback.

These are the three most important insights I gained from working as an Engineering Team Lead at Automattic.

Don’t Fall into the Safety of your Old Job

Stepping into a new role, like managing people or projects, requires different skills than the ones that made you shine as an individual contributor. Recognizing that can be difficult.

It may be very tempting to keep on working on what made you successful earlier. Maybe you want to keep doing individual contributor work, like coding that really impactful, but difficult, feature. When you notice this happening, take a moment to pause. You’re in a different role now! Your biggest responsibility is providing clarity and direction to the team, communicating in all directions, and helping foster personal development.

Taking on both the responsibilities of an individual contributor and leader is unreasonable and unmaintainable. Not letting go of that role is an unintentional signal that you don’t trust the team. It also deprives people of opportunities for them to grow or to really excel at their craft (they may do a better job of it than you and that’s fantastic). The book Multipliers, has an excellent analogy for this. Imagine a coach that gets frustrated with how the game is going, and instead of coaching the team on their next strategy, runs onto the field to score that winning goal themselves. Just think of what the team would feel in addition to the crowd.

That isn’t to say that you never should code or design. I find that it is often the least impactful or important thing you can do to help the team. It’s still useful to keep in touch with your prior skills to understand what needs to happen to be a great individual contributor, but it’s not your number one priority anymore. I still personally code-review and code, but this comes last after all my other responsibilities. If I do take on coding it’s often something small that I know I can complete with my fragmented time or I pair with someone who can still own that larger feature.

As a team lead, you’re still part of the team, you’re just in a different role. It can be lonely at times. There can be very little actionable feedback on how well you’re doing, both good and bad. Rest assured the role you’re playing is just as important as everyone else’s position. It’s natural to fall back into these habits of doing things yourself. But when you notice, gently correct yourself and ask: “Is this where I’m needed most?”

Listen and Take Action

A key skill that is important but difficult to master is listening. Knowing when to take action from that listening will make you super effective.

I will be talking about this with the caveat that I’m still working very hard to listen better and more thoughtfully. One of my biggest fears is that I will mismanage people. I think one of the best ways of avoiding this situation is by listening.

So what do I mean by listening? It’s when I can give the space for people on the team to speak, building safety so they can voice their feelings and thoughts, and to do it on a consistent basis to help build our personal relationships and trust together as a team.

Every team is different, and every team will face different problems, but it never hurts to listen, and to listen on a consistent interval.

Listening is often formalized in the form of processes. It gives us some structure to learn how to listen and hopefully take some constructive action from that.

I’ve found Retrospectives and 1:1s to be both simple in format and useful. Sometimes when implemented poorly people find that these exercises are a waste of time. When used correctly they will help you listen to the people on your team, and will help to clarify what next steps are most impactful for both you and the team to act on.

In the next sections I’ll explain each exercise in more detail.


What is a retrospective? It’s a regular meeting held to discuss three things in a structured way:

  • What worked well for us?
  • What could have gone better?
  • What actions can we take to improve this going forward?

That’s it! This meeting is all about lessons learned and trying to improve process so we can repeat what worked, and try to change the things didn’t in a completely blameless and constructive way.

The key idea here is to start a virtuous cycle where:

  • We build trust so people on the team can truly say what they think and what we probably need to change
  • We take action on that feedback
  • We do this consistently, to show that we care, and to create great outcomes for the team.

Before your team adopts retrospectives as a practice, make sure people are committed to trying to listen and that your team has the agency to take some action.

What Retrospectives May Uncover

Retrospectives have a lot of benefits and will sometimes uncover insights of surprising depth. This may include:

  • Reflections on team dynamics.
  • Daily work done well, or small things that we can all celebrate together.
  • Reality checks of how well a project is running and if we’re working on the right things.
  • How the team is really feeling.
  • Systemic issues beyond what the team can solve alone.

What Can Go Wrong in Retrospectives

Sometimes, it feels like process is a waste of time, because it is. Retrospectives can fail to be useful in a number ways:

  • People interrupt others, or don’t let each person have an opportunity to share. The loudest voice is heard above the others.
  • People don’t feel safe to share their actual thoughts and feelings. There is not enough trust with the people involved, or trust that anything will change.
  • People never follow through on action items for any number of reasons. Maybe the action item is not actionable. Maybe no one was held accountable for it. Maybe it cannot be solved solely by the team and we cannot see a first step.
  • Action is only taken on the easy items but nothing is never done on the hard problems.
  • Tangentially arbitrary work is added as an action item that has little relation to what was discussed.

So in some cases, people may go through the motions, still feel unheard, and no change takes place. We aren’t committed to listening and taking action on it.

The Retrospective Prompt

The format I use is simple, but can be experimented with and modified. If you search for “Retrospectives” you will find other prompts on the internet that may be more suitable for you to start with and iterate on.

It’s really important to note that this entire exercise should be driven by the team, and that everyone has a safe space to share their thoughts and feelings. Yes, even Engineers have a lot of feelings because they are human. My alternative name for this exercise on Engineering teams is Engineering Feelings.

We should also remember to celebrate anything that is working well, in addition to recognizing when things are not. Some retrospectives might be gloomy if the team is facing a difficult challenge. In another week the team might be enthusiastically happy and we may have trouble finding action items.

For retrospectives to work, it is vital to do them on a consistent basis. This gives us a window of time to reflect and act on items. If the time period is too great, I find that two things happen: people don’t remember what actually happened, and action items are not accountable since the next meeting is so far away. My team holds a retrospective every two weeks because that cadence works for us.

Give Everyone 5 Minutes to Write Down Thoughts

Separately let folks write down their thoughts for five minutes (on physical or virtual stickies) with the above prompt for the time interval specified. It’s best if people can’t see what others are writing.

Everyone Shares Their Stickies

Once the stickies are ready, the team shares their thoughts verbally, one by one. People will often expand on what they mean instead of reading the note verbatim. When a person is done reading notes, the next person should start. In my case I usually just call on someone to share next, but other methods should work too.

Resist the temptation to immediately dive into a conversation on how to improve things. We’ll have the opportunity to do so after everyone has shared.

Group Similar Stickies

Group similar stickies together into common categories or themes. It’s okay if everything doesn’t fit. If you have a number of people, vote on the themes you’d like to discuss most.

Go Over Old Action Items From Last Retrospective

Before diving into each category, go over action items from the last meeting. Were they acted on? If not the old action items are automatically added to this retrospective’s notes too. If things keep getting kicked to the next meeting, assign it a higher priority to finish it, or revisit to determine if it’s still necessary.

Discuss Each Category in Detail and Create Action Items

The team can now chat about each category and brainstorm ideas of how to improve trouble spots, or celebrate wins together. If people notice that a note is more of a feeling, dig down into why they feel that way. We may still be able to create an action item out of it!

An action item should be relevant and small enough for a person to accomplish in your retrospective time period. Assign a specific person to a task, so it has a higher chance of being done.

Tasks might range from, “Let’s use a different label on issues we file” to “I need to refine and deliver feedback that the project is going sideways and why”.

Publish Meeting Notes

Regardless of whether you have a physical office, or are completely remote, having some artifact of what themes were discussed and action items were created is a must. We can’t see our progress as a team, if we don’t document it!


One on ones are a formalized way of making sure you talk with each person on your team in a private meeting. Depending on the size of the team this may be weekly, or every two weeks.

What you talk about with each person during this time is entirely up to the participants, but may span a number of subjects, from a check-in of how each person is doing to clarification of company goals or helping spot opportunities for personal growth. Less often, it can also act as a safe space for people to feel heard during difficult moments. Sometimes active listening is all you need to do, without needing to have anything change or be “solved”.

Like with any relationship you build with another person, it takes time, and some of the early sessions may feel awkward, entirely casual (totally okay), or way too in the weeds as you get to know each other.

It’s really helpful to let team members come up with points they want to discuss first. It might even be rare feedback for you which is important to hear and act on. This time is for them! Listen before moving onto your own agenda, like feedback or personal growth, though don’t hesitate to move on if they are dominating the entire meeting.

It is useful to keep shared notes with your reports that outline briefly what was said and any action items created (for you or your report). This shared document acts similarly to the written meeting notes in retrospectives. It will help spot themes or repeated conversations, and add accountability to making sure action items are completed before the next 1:1 meeting.

Like Retrospectives, 1:1s are simply a tool to help listen and to maybe act on what is being said.

Providing Useful Feedback

One of your new responsibilities will be letting others know how they’re doing, why that’s so, and shining light on their strengths or areas where they can improve.

It’s unkind to leave people without this feedback, especially if you’re holding onto constructive feedback, because you’re scared that you won’t be liked, or that you’re personally friends. Similarly, if you focus all your time on folks who are having more trouble, this isn’t fair to the people doing well who could use guidance on how they can grow even faster.

Providing useful feedback is a lot of work, but it is very necessary work to help people grow.

Delivering any feedback, both good and bad, is its own subject and skill to master. There are entire books written on how to listen, craft, and deliver feedback well. I would highly recommending reading a few. After you do this, note that you can read and understand the theory but applying this on the spot, in the heat of the moment, is extremely difficult. I am very much a novice at this. Very briefly, here are a few things I wanted to highlight:

  • Great feedback comes from a place of care. You are taking the time and effort to craft this feedback to help someone improve their behavior and succeed, or are highlighting what they are doing great so they can better understand themselves and maybe even build on their strengths.
  • Giving positive feedback requires as much care as constructive feedback. People need to understand what they’re doing well, in what specific instances and why. They won’t be able to apply this feedback otherwise. In a lot of cases the compliment may even feel insincere. “Keep doing what you’re doing!” Is not helpful. Keep doing what?
  • Constructive feedback is best delivered privately and as timely as possible to the situation you noticed. Be careful to avoid value statements. It isn’t a quality of the person that needs to change say “John Doe is a mean person.” It’s trying to highlight a person’s behavior in a specific instance, explaining the impact that it had on others, and what behavior would be more appropriate in a similar situation, or opening a conversation on what that might look like.
  • Constructive feedback is always difficult to hear and to deliver, so take care that the listener is in a good space to try and listen, and that you are ready to try and deliver that feedback.
  • Despite your best intentions, the burden is on you to deliver feedback in a way that is both respectful and can be understood by the listener. It is very easy to get this wrong and hurt people unintentionally.

Listening To Feedback

In some cases people will be giving you feedback. Feedback given to you is a rare gift, but oftentimes, really listening and understanding that constructive feedback can be difficult.

Many people find that the body enters a fight-or-flight mode. Try and notice what you’re feeling. Do you maybe deflect and become defensive? Do you freeze and are unable to hear the rest of the message? Maybe you just feel bad about it, and miss what is being said that is supposed to help. This is something to keep in mind when you write feedback for others, it can be really difficult to hear what is being said.

More often than not, the feedback you receive may not be well-crafted. It may lack specifics, be a value statement, or you may not even agree with the points being said. Instead of dismissing this, maybe take some time to understand what the person really means by it. After all, the easier move is to say nothing if they didn’t care about you. With more conversations, you may be able to find that step of personal growth for yourself.


So, as a new manager, remember these three things: don’t fall into the safety of your old job, listen, and provide useful feedback.

Don’t fall into the safety of your old job. As a manager your role isn’t the same as an individual contributor and relies on different skills. The team needs you to provide direction and clarity. Don’t be the coach that runs onto the field!

Listening is a powerful tool. Over time, team trust and cohesion may be earned by listening well and sometimes taking appropriate action from that listening. Retrospectives and 1:1s are simply tools to help make this happen.

Useful feedback will help accelerate the growth of each team member. Individuals will better understand their strengths, areas of improvement, why that is, and what they could try instead.