In this post, I’m trying to summarize the pitfalls of working from home without the remote-first mindset I’ve experienced. I’m also adding a few tips that worked for me over the years. They helped me at various points of my remote journey. I hope others will find them useful as well!
This year, I’ve seen many of my family members and friends transition to working from their homes full-time. In most cases, their workplaces were not built for remote-first and now embrace the always-online culture. Hearing their experiences reminded me of how tough is the journey from working in the office to being fully-remote.
I’ve had the luck to work at Doist since its relatively early days. We’ve built Doist as a fully-remote company from the ground up. This advantage gave us the luxury to develop our culture and process from the ground up to complement remote work’s strengths and avoid its pitfalls.
We’re not the only ones; other great companies like Zapier, GitLab, or Toggl together form a community of remote-native companies. Remote-native companies vary in many aspects, but they frequently emphasize two aspects of their culture:
- Asynchronous communication whenever possible. The belief that preferring longer-form but slower forms of communication produce better outcomes while taking less toll on their workforce by removing the “always online” requirement.
- Work-life balance. The belief that working 12+ hours a day is not sustainable and will hurt both the employees and the company in the long-run.
Asynchronous communication and work-life balance are tightly complementary. Work-life balance is hard to achieve with constant requests for meetings and phone calls from dawn to dusk. Asynchronous communication is likewise hard without minding work-life balance; slipping into DMs is just too comfortable without a mental block in place.
Unfortunately, many companies transitioning to online-first culture are altogether eschewing both asynchronous communication and work-life balance.
Late-night pings or Teams or Slack are commonplace, and so are meetings scheduled in the previously-sacred lunchtime. The amount of meetings has not decreased; online meetings are even more draining compared to in-person ones. To top it off, many people end up working longer hours, creating the perfect coctail for burnout.
A less talked about but crucial aspect of working from home while eschewing async communication and work/life balance is an impact on the family. Doing homework while your mom is going through a series of heated meetings in the other room is a draining experience for the kid. And for the rest of the family as well.
In short, lots of companies are going remote but are not picking up remote-native practices, hurting their people and themselves in the long-run.
In companies where the big picture is hard to influence, I’d like to share a few practical tips that helped me over the years, from two distinct perspectives:
- Individual Contributor Tips. Tips you can apply individually, without requiring broader buy-in first.
- Team-Wide Tips. If you can influence your team (being the team lead helps, but it’s not necessary), these tips could come in handy.
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Individual Contributor Tips
Talk to your team lead. The first thing I recommend. It’s your team lead’s job to make sure you have the best possible conditions to succeed. If the new team meeting interferes with you needing to pick up your kid from school, it’s your team lead’s job to figure out a solution. If you’re exhausted by all the Zoom calls, ask your team lead to work on a team process that’s less meeting-heavy.
Ask for an agenda before accepting a meeting. If you can, explicitly ask for a written agenda before accepting a meeting or a call. If the other person can’t present an agenda, try to politely postpone the meeting until there’s one. Even if you fail in delaying the meeting, you have created an expectation for next time, resulting in fewer meetings down the road.
Comment on the agenda before the meeting. If you get an agenda before the meeting, try to reply to it with what you’d say during the meeting and ending the email with something along the lines of Let me know if you’d like to discuss further; otherwise, we could skip the meeting? Most people want to skip meetings as much as you do; make it as easy for them as possible.
Delay responses to unimportant requests. If you get lots of DMs from specific people asking you about things they could quickly solve themselves, intentionally delay your answer. This is frustrating for the other person in the beginning, but you motivate them to self-solve. In the long term, the stream of messages slows to a trickle; everyone is better off.
Unapologetically exit overtime meetings. If you have a problematic meeting scheduled for 30 minutes but routinely running for 60 minutes, try to schedule one of your meetings to follow the problematic one. This allows you to exit the first meeting at the 30-minute mark gracefully. Be explicit that the meeting was scheduled for 30 minutes and that you have another meeting coming up. Doing so generates pressure on the meeting organizer to run the meeting better and not go overtime.
Have a hobby with scheduled events. Having hobbies with fixed time slots (language lessons, music band practice, etc.) that are hard to cancel is incredibly helpful to help to build the crucial work/life boundary.
Most of the tips are about adding small bits of friction to reduce the frequency of interruptions. If people contact you, they should feel a bit of pressure to come prepared.
If you can effectively influence your team or set policy, you’re well-positioned to improve your team’s well-being and long-term productivity.
Model individual contributor behaviors. If you start rejecting meetings without an agenda and make it clear that it’s ok to not respond within five minutes, as suggested above, your team will quickly follow and adopt the same behaviors.
Create a “Meeting Best Practices” document. Early during my time at Doist, we created a policy for conducting meetings that enshrined best practices like “no meetings without an agenda” or “all meetings last a maximum of 60 minutes”. This made it clear that meetings have limits. Having a similar policy on the team level can improve the meeting culture as well.
Designate a specific person to run team meetings. If you have a person in the team who enjoys running meetings and can devote energy to it, ask them to run team meetings. In many cases, this person will not be the team lead. If you can find a great person for this job, you’re giving the whole team a role model and a mentor for running effective meetings.
Promote a culture of sharing current stress levels and emotional challenges. By openly talking about your mood, stress levels, or health problems and encouraging the whole team to do the same, you can create a team culture of caring for each other and cutting folks slack when they’re not at their best. Team members are great at supporting each other through burnout or other work/life balance issues, but they need to know that it’s happening.
Model, document, and share. As suggested in the book An Elegant Puzzle by Will Larson, once you find behavior that works and spread it in your team, consider evangelizing it beyond your team as well. Other parts of the company will be happy to adopt battle-tested solutions to problems they’re also likely facing.
Becoming a remote native is a journey. Working remotely has many great perks, but setting firm boundaries early in the process is essential to preventing burnout down the line.
Solid boundaries take time to build, especially within companies new at remote, but they pay off with sustainable personal and team performance in the long-run.
If you’re new to remote, take care of yourself, and be honest about your limitations to your team as well as to yourself.