Remote Work Musings

I’ve been working remotely since 2015 across 4 different companies. I’m also one who constantly seeks to learn and optimize things. As such I have thought on Remote Work that have been stewing in my brain for a while figured it’s nigh time to write them down.

Disclaimer: Even thought I’ve been working remote since 2015 the pandemic lockdown hit me hard. I had a suite of tools that I would use to work effectively remotely that were also taken away during lockdown. Only now do I feel like some of those tools are available again. Although the lockdown definitely permanently changed some of them.

As I am continuing to learn it’s a journey with Remote Work rather than a destination.

Key Points

Two key points to keep in mind about working remotely:

  1. You are working remotely! The amount of flexibility that can come with working remotely can and should be taken advantage of. Need some time between 3 and 4 to settle the kids down? No problem! Have to wait for the electrician to come at some 4 hour window? Sure! Just feel like a change of scenery so you booked that AirBnB by the beach? Awesome! Plus the time saving on commuting is stellar!
  2. Remote work is not synonymous with never in person There are tasks that work better in person (intense collaboration, brainstorming, high complexity work, etc) and there is still the human element of connecting with your coworkers that is difficult to quantify. As someone who is firmly on the introverted side of the introverted/extroverted scale it surprised me how important that connection was to me.

There are other points, however those two are the most important to me to keep in mind because they help inform how you can design the rest of your work and workflows in an efficient way for you.

Work/Life harmony

The boundary between where work starts and ends becomes blurred when working remotely. Have work and life be in harmony in a sustainable ways is probably the biggest huddle to being successful working remotely.

It’s pretty natural to setup “working hours” and figure out ways to defend them, although for me this takes away part of the flexibility on being remote. That’s not to say I don’t have “working hours” – I just let the boundary be flexible – if I need to take my kid to soccer at 4pm and finish up work at 7pm then okay by me .

There is also the physical and temporal boundaries of work and life. For most of us being remote means work is literally in our homes. Boundaries can be hard to setup when you wake up and work is staring at you. Also hard to have a relaxing sleep with Slack buzzing right before bed.

My actual structure (mostly)

Here is how I design my work and life harmony – it’s not perfect and won’t be for everybody, heck it’s not even right for me sometimes but sometimes examples help.

  • 20 min walk right before work – this is my “commute time” and helps setup a temporal boundary between life and work. My brain starts to transition from “did the kids remember everything” to “what tasks do I need to do at work today?”
  • Heads down work out of the house – distractions come too easily for me at home – I will go to a cafe, park, restaurant, co-working space, library, etc. ( not all these places are secure!)
  • Will catch up on emails/confluence/slack at 6am OR 6pm if needed – buffer time for when I need to catch up.
  • Avoid responding to Slack past 6pm
  • Pretty hard “no-work” lines on Saturday
  • Sunday typically I have 2 hours to plan my week ahead
  • Everyday I try to have a set of “most important things to do” that I need to get done before I can consider the day “over”


Communication is something I have been thinking a lot on recently. To me there are two kinds of communication Asynchronous & Synchronous and two roles in communication Sending & Receiving.

In a remote setting, especially in a geographically distributed (meaning everybody could be in a different timezone) remote setting, the more asynchronous communication the better. This can be the hardest part about a remote setting. In an office synchronous communication is the norm, successful remote work requires asynchronous communication to be the norm.

However communicating effectively asynchronously is HARD. The trick is knowing what needs to be synchronous and what does not. Also requires assumptions to be challenged.

I’m going to lay out some tools and techniques that can and are being used for communication and where I see their strengths and weaknesses, what kinds of communication they are good for and some remarks on the responsibilities for sending and receiving. I’m not thrilled with this format and these are definitely not hard and fast rules – depending on the audiences, content, time sensitivity, etc there are choices to be made.

In Person Communication

There is no better way to communicate synchronously than in person.

Things that are complex, require a lot of back and forth, when nuances or emotions are high all benefit from In Person Communication. Brainstorming, tense situations, strategy alignment, are all example that benefit from In Person Communication.

Luckily most In Person Communication are things that can be planned in advance and typically don’t require immediate attention. As such there is time to coordinate time and place.

Because In Person Communication is so good at capturing nuances, and can be very fluid the sender and receiver roles tend to be share among all participants and the transitions are very natural. That said there are some dangers here. It’s important to be a good listener and give quieter folks room to have a voice.

There is also the side benefit that when communicating there is an “squishy” benefit of just being able to connect to other humans face to face.

Before the pandemic lockdown at all the places I worked in recurring In Person time.

  • Remote First Startup Head Quarters in Philly : standing weekly HQ invite (usually timed with food trucks), yearly in person all hands.
  • Mid Sized Startup with Locations in Chicago and NYC : quarterly team meeting in Chicago, monthly I would be in Chicago or NYC.
  • Small Business in NYC : every other week would be a day in the NYC HQ.

There were also ad-hoc meet ups in coffee shops, lunch spots, and happy hours in all the places.

Phone Calls

I know no-video Phone Call are quickly becoming out of style or old-fashioned . However I still think there is a place for phone calls in the modern remote workplace. Personally I think they are 2nd best for synchronous communication when there are only 2 people involved. They work better than In Person Communication when there are more time sensitivities involved.

Things like recurring 1:1s or those “hey got a quick sec” can very effective over voice only Phone Calls.

Phone Calls do an okay job at capturing nuances, and sender and receiver roles tend to be share among all participants and the transitions are very natural. This is especially true when there are only 2 people involved.

Video Calls (everybody remote)

Video Calls are the workhorse of remote work. The defacto go to for all synchronous communication in a remote environment. For good reason – it does a reasonably good job of keeping us connected. While working remotely and you need to communicate synchronously it’s fine to default to video calls. However before just jumping to video call I would encourage to quickly think through:

  1. Why are we doing this communication synchronously? Can we turn this into an asynchronous communication?
  2. Would another synchronous method be more effective?
  3. What Timezone(s) are the participants in? Is it super early or super late that for some people that would make this less effective?

Most cases the answers won’t stop a video call meeting completely, however thinking creatively may lead to splitting communication into more effective pieces. For instance a design review could 100% be done asynchronously (with a lot of up front work), or it can be done partially asynchronously and a shorter video call is need. Or maybe you have a feeling there is going to be a contentious meeting doing a 5 min voice call before the meeting (and that didn’t happen a phone call after is better than letting people think the worst) with people you think may be affected could pave the way to a less contentious and therefore more productive (and shorter!) video call meeting.

Sidebar on Video on / Video off

Having video on or off should be an individual decision. However there are some things to note:

  • There are plenty of reasons to not have video on, however video off can send a signal of being disengaged. To combat this I usually warn people when I will have video off and give a reason (even if the reason is just “need a quick break from being on camera”)
  • Consider having video on with large meetings – even if you are mostly receiving you will give visual queues to the sender.
  • Sometimes I’ll put video off on 1:1 because I’ve stepped away from my computer to stop myself from being distracted with other things.

Video Calls (hybrid)

Video calls have etiquette for senders and receivers that we are all still figuring out. There are inequalities that show up on video calls that being a bit more intentional on your responsibilities when sending and receiving can help lessen. Sometimes people have slower connections, sometimes the network glitches, some people are slower than other to speak up and “lose” their chance to be heard.

When you are sending information it’s important to reach to all who are receiving. Sometimes this is stopping someone from verbally responding to your message before you think everybody is ready to move on. Sometimes it’s explicitly calling on someone. Setting expectations or ground rules on how interactions should happen is perfectly reasonable.

When you are receiving information and you want to respond use the tools available. If you can speak up, great! If someone always beat you use the raise hand feature or the chat feature. Heck you can even use other tools outside of video calls to follow up.

Time management is also important with video calls. Video calls can feel transactional and sometime feels like the meeting ended abruptly or drag on for no good reason. Setting expectations on outcomes helps, but if they aren’t reached you aren’t sure it’s perfectly fine to followup using a different communication tool.

Hybrid meaning some participants are remote, others are together in a conference room or else where.

Everything mentioned in the Video Calls (everybody remote) holds true for hybrid video calls. The reason hybrid video calls gets its own section is because as soon as there are 2 people “in person” there is an immediate imbalance between the people “in person” and the people remote. There are articles and such that say you should just take all videos call from you laptop so everybody feel remote – I’m not sure that’s always practical (although if it is practical it is effective at making things more level).

Another callout with hybrid video calls is typically everybody in the video call has their name next to their face. This isn’t possible when people are in person so consider if a round of introductions is in order. Actually that is important no matter all remote/hybrid/in person – if there is a chance people do not interact regularly intros are a good idea!

The biggest call out is for the people “in person” – see the In Person Communication Section – in person has such a more fluid sender and receiver dynamic that is completely up to the people in person to include the remote folks. Consider when in person to adopt “presenter” etiquette: speak slowly and clearly, include the camera when you “scan” the audience.

Chat Tools

Slack, Teams, Discord, etc

Chat software are an interesting tools, they has the capabilities to do synchronous and asynchronous communication. Which kind of communication is completely up to how the chat tool is used, the role of senders and receivers, and contents of the communication/message.

Since the sender is usually the one that initiates the communication most times the onus is on the sender to property frame the message (is there urgency that requires synchronous communication? is the receiver at the computer? is there a status icon from the receiver? is it a direct message to someone or a group chat or channel?). It is good to be conscious of how the receivers may perceive the framing.

However not all responsibility falls to the sender, the receiver also has responsibilities. The receiver needs to make judgement calls on when and how to respond. Was the message sent at an inconvenient time? Say you are in engaged intently in other tasks or communication or it’s after hours? Does it look like it needs to be synchronous? Is it just an FYI that requires just an acknowledgement of receipt? (for quick acknowledgment consider emojis 🙂👀 ✅ 🤔) I find it helpful as a receiver to always assume good intentions by the sender, after all with chat the roles of sender/receiver switch between parties involved rapidly.

There are techniques that should be experimented with (scheduled messages, explicit “respond later” or “sorry this is really urgent” preambles on messages, asking if a response is needed immediately or asking to move to a different medium or channel, scheduling a reminder to respond, batching messages, etc) however know that this is still an evolving form of communication (remember when things like emojis, threads, and reactions didn’t exist?)


Email is an asynchronous communication tool (I’ve been places where it was use almost synchronously, but that’s just weird)

Generally I find email works well with things like:

  • FYI type messages to large groups (newsletters, announcements, etc)
  • Time delay for response is measure in hours or weeks
  • When you want to add some formality to the message (kickoffs, decisions, etc)

I feel like with the combination of chat & email using email allows more space for the receiver to think. Which is another point – the sender will be more effective if they know the receiver’s use of email.

Types of Work

Generally work can be divided into two broad categories

  • Deep Focus – these are things that take time and concentration. Things like coding, designing, strategy planning. I would also include meeting that take a lot of concentration as well, things like interviews, design sessions, monthly business reviews, etc.
  • Routine – these are things that are more mechanical and less intense focus. Things like checking email, updating a status template, writing a TODO list. I would include meetings that could tolerate interruptions to the flow as well, things like stand-ups, lunch and learns, some 1:1s, etc.

There are some gradients in there as well – something like a code review will require concentration, but is more tolerant to disruption than say coding a feature that spans 2 code bases across 10 files.

A good litmus test is how difficult will it be to get back to what you were doing after being interrupted.


The longer it will take you to get back to what you were doing the more “Focused” work the task it, the shorter the more “Routine” work the task is.

Then depending on the kinds of work you will be doing on any given day you can try and optimize your environment for that work. For focused work this can include things like muting slack, turning off emails, getting some creative music on, blocking your calendar, etc. For routine tasks it can be batching a bunch of routine tasks together instead of one offs,

Actual techniques

  • Sometimes for 1:1s I will go for a walk as this takes the distractions of the computer away to so I can listen more intently
  • I will block times off in the day for focused tasks in my calendar – usually for me this is in the morning hours as I’m more productive then
  • I’m pretty much 100% on the manager schedule these days and with two children at home finding time for really intense focused work is tough – sometimes best time for me is the wee hours of the morning.

Calendar Management

I find actively managing my calendar is a crucial tool to being remote. Things I do:

  • Defrag my calendar (to the best I can anyway)
  • Block off time (and write in the meeting what I am using the time for) when I need to get something done
  • Decline or adjust meetings agendas ahead of time when initial invite is unclear
  • Recurring meetings always having a drop off date, meetings that are needed quickly get added back
  • Quarterly review of meeting cadences – design for best use of meetings and time

Core Hours

Maybe this isn’t strictly Calendar managements, however if you can find a block of 4-6 hours where the people you work closely with agree to be available for synchronous communication that can make calendar management easier.

Another item that helps with calendar management is opening up your calendar for all to see. This really helps when scheduling time with a large audience.


All above is subject to “culture”. Whenever groups of people get together “culture” happens. One person cannot set culture, it is collectively cultivated.

The more you can foster a good remote culture wherever you are the better.