Remote and distributed work is an unstoppable trend recently accelerated by five to ten years. It allows people to live where they want to live, and people who couldn’t move or regularly visit an office before can find better jobs.¹ Remote work is great for a more diverse workforce, and I’m glad this trend is here to stay. However, it’s much harder to build a shared sense of purpose and build empathy for colleagues. This post exists to help people and teams adapt better to this new era.

In a hurry? Jump straight ahead to the Recommendations.

A New Era

I expect many companies will operate with a hybrid model of partial work from an office and partial work from home. Even if you aren’t sure whether you’ll work from an office or elsewhere in the future, the age of a singular big headquarter per company with everyone in the same place has passed. The new norm will be multiple engineering hubs, fully remote companies, or a mix of headquarter, hubs, and remote work.

However, there are trade-offs to remote work. While many people prefer a silent home office because it makes them more productive, it can be an isolating experience.² Many essential moments that bring people closer together do not exist without meeting in person and are hard to recreate. Sure, we see faces pop up on video calls that we can interact with, but the human connection is missing, and it is hard to really get to know and understand people. All the work we do at home in front of our devices is just in our heads.

The reduced social interactions make it harder to meet people and build a network. There are no serendipitous interactions in which one can learn, solve problems or maybe make friends. Many people just work on their tasks. It looks like people are more effective in the short term, but people are likely to have a worse time long term. It’s no surprise that people with a best friend at the workplace perform better and are happier.

Another angle is company culture. How do you retain a great company culture when everyone switches to remote work? How do you build a fantastic and unique culture with a fully remote team? Culture is living your values every day, which is hard to do without a shared sense of purpose. This quote from Stratechery on leaks resonates with me:³

I strongly suspect, though, that the closing of Facebook’s offices has played a large role as well. The likelihood of an employee feeling a sense of solidarity or common purpose is almost certainly less when a said employee is only interacting with his or her coworkers via a video call, instead of in person. Moreover, that reduced interaction is increasingly replaced, or accompanied, by alternative interactions, particularly on Twitter, that pulls said employee in a very different direction.

Finally, I was reminded of just how different working remotely is when a former report, whom I never met in person, watched a video of me and said: “I had a completely different image of what you look like. This is literally the first time I see you outside of the usual ‘talking head frame’.“ It’s no surprise that many engineering managers prefer being in the office with their reports!

Recommendations

So, what can you do if you are a manager or leader who wants to get to know their coworkers better, improve relationships with their reports and within the team, increase belonging, and build a shared sense of purpose? I approached inclusion with intentionality, tried many things, and I’m excited to share what worked for me. The recommendations build on each other:

The Weekly Social

Early into remote work, I had a realization: The best moments in the office were team lunches. We tried to sit together for lunch as often as possible. Lunches are so valuable because they are informal, and optional, and conversations aren’t bound to work topics. There is usually a time limit when people want to get back to their actual work. It’s a great way to learn about your peers!

Organizing team lunches over video calls does not work.⁴ So how do we recreate the feeling of a team lunch without feeling forced? Set up a social meeting with the entire team once a week. Depending on team size, this will be 30–60 minutes. Thirty minutes if it’s less than six, and 60 minutes if it’s up to twelve people. Each of them should have a unique topic to cover. Ask everyone on the team to contribute. For some of the meetings, decide on a topic two days ahead and invite people to prepare. While you can come up with a quick question during the meeting, the great ones are usually the ones people prepare for.

As the manager (or the CSO⁵ of your team), prepare an introduction for each meeting. Usually, you have news relevant to the entire group, or maybe you can do a brief Q&A about a topic pertinent to the team. Then move on to asking the question and pick a random person in the group to go first. Each person should stick to a time limit so that everyone gets to participate. We usually went with a random approach where the current person picks who shares their answer next.

You may have been in a variant of this type of meeting before, and the questions might have been pretty dull. I have been, and I tried to come up with a list of boring questions you should avoid but couldn’t because of how dull those meetings were. The questions weren’t meaningful. You have to ask questions that will be meaningful to people which sometimes require them to show vulnerability.

Depending on the team, you have to ease into it with simple questions. Like, let people talk about their favorite food, hobbies, favorite place in the world, a video they think is funny, or explain something unique about themselves. If your team is already close, you can move on to questions that consistently lead to extraordinary and memorable meetings in which everyone gets to know each other better:⁶

• Share childhood/teenage photos of yourself and tell a story.
• Share one or more favorite engineering projects you worked on before joining the company (with screenshots etc.).
• Show a photo, video or Street View of your hometown and tell us what makes it unique to you.
• How did you get your job at the company? How likely was it that you ended up here?
• Why did you join this team?
• What is something that you’d like to improve this year (personal, work) that you’d like the entire team to hold you accountable for?
• If you weren’t an engineer, scientist, researcher, designer, etc., what would you be instead and why?
• What’s something that you did as a child/teenager that you miss doing?
• Tell us about something that you are still embarrassed about today.
• What’s something dumb you did as a child/teenager?
• Tell us about a trip/event/weekend where something went wrong.
• (If everyone has children) What makes your child/children so special to you?
• Make your own questions. Let me know if you come up with one that works really well!

Not only will you get to know people, but you’ll also learn to understand cultural differences across the team better. It will help you be a better manager and makes people more mindful of each other’s behaviors.

Sharing has to be entirely optional. Nobody should feel pressured to share personal stories, and anyone can skip topics that are too personal for them.⁷ People may be shy, or they prefer to be very strict about their separation between life and work. Approach it privately with them, ask about their reservations, recommend how they can participate, and agree on something that works for everyone. A lot of this can be pre-empted by proactively asking people for permission to start doing a social meetings.

If you do this every week, I guarantee that the team will be healthier within three months. People will be happier and produce better results, and almost certainly, they will trust each other more.

Share Personal Status Updates

Let people know about your whereabouts. When working remotely, all you see is the output from people. Somebody sends Pull Requests at 7 am, 3 pm, and 10 pm? Wow, they must be working super hard all day! Observing that can lead to a lot of pressure and stress across the team as individuals may think they have to work harder, too. What you don’t see is when your colleagues aren’t working. For example, in the above example, maybe the person woke up and shared the code they wrote the day before, then spent time with their children until getting back to work between 3 pm and 10 pm, during which time they also cooked dinner and took a break. Other people may prefer to work out during the day and work late at night. As long as the entire team is available at certain agreed-upon times and people don’t miss meetings, that should be ok. It makes sense for everyone to share their schedule and availability. You can even do this as part of the weekly socials: “What is your work schedule like?”. This exercise builds empathy for each other and makes people more mindful of everyone else’s work-life balance.

Besides, people should also announce deviations from their regular schedule, like when somebody is missing a team meeting because they aren’t well or have an appointment. An extension that I’ve seen work on some teams is to share what people have been up to on weekends or what they cooked/ate during holidays. Sharing such private information is not for everyone and all teams. I’m not talking about tracking what your colleagues do in their personal life but instead asking them to voluntarily share things they are comfortable sharing about themselves to lighten the mood. You can make the team more comfortable by telling them why it is valuable to share more.⁸

To make space for these updates and conversations, I like to have a private social chat for the teams I work with. “Private“ so that nobody feels like they are sharing with the whole company and “social“ to set the expectation that it’s ok to miss messages because they aren’t work-related.

Buddy and Mentorship programs

Ensure people don’t feel lonely. It doesn’t matter if they work alone on a project, lead a big team or have a big family at home – people can still feel lonely. Buddy and mentorship structures can provide support – both technical and personal. From the Management Starter Pack:

Mentorship structures: Identify or create genuine situations in which people need to help each other out. Pair up new hires with a social buddy and a technical buddy. Pair up experienced people with each other to help them fill gaps.

Mentorship structures ensure that everyone has at least one other person besides their manager looking out for them. I usually suggest starting with weekly 30-minute meetings that can be increased in cadence or length if necessary. Buddies can set up informal meetings to catch a break and talk in a more relaxed setting. For new hires, it doesn’t stop there: Buddies can recommend and maybe even set up meetings with other people on the team or the organization. This makes new hires feel like other people are interested in getting to know them.

Mentors and buddies have the added benefit that they can take on management work and therefore free up their manager’s schedule for other tasks. Mentors can improve the team as more people will be aware of how individuals are doing. As a manager, it’s helpful to check in about how mentees are doing: Maybe a mentor picked up on something that’s bothering someone on the team, but the mentee doesn’t feel comfortable sharing it with their direct manager. Maybe somebody isn’t enjoying their project? Perhaps they are stuck? It’s easy to miss these things when not working in the same room together, and more people checking in with each other will surface issues sooner.

Retrospectives

Organize retrospectives to take collective ownership of the team’s direction and allow everyone to propose improvements. I’m not too fond of processes for the sake of process. I much prefer picking specific things from established processes that may work with a particular team. One of those is doing retrospectives targeted at collectively driving the team towards a specific outcome. Be it understanding a mistake made, learning how to improve things for themselves, or exploring what they’d like to work on next.⁹ These meetings tend to take longer than any others, usually between 90–120 minutes, and require preparation and much coordination. Because of that, I generally don’t recommend more than one retrospective every 3–6 months.

I like to prepare a collaborative virtual whiteboard (such as Excalidraw) that everyone joins and works on together. The topics are agreed upon and shared ahead of time so that everyone has a chance to prepare themselves.

While every team is different, here are some of the topics and questions I discussed in previous retrospectives:

Team Focus

• Celebrate a project/team/team member/goal from the past six months.
• What worked well in the past six months that we should keep doing?
• What didn’t work well, and we should change?
• How can we work more effectively together remotely?

Engineering / Project Focus

• What are the systems/tools/products that have poor quality and need improvements?
• What are our partner teams? Who are the responsible individuals on our team?¹⁰
• How can we reduce time spent on on-call duties?

People Focus

• What’s your highlight from the past six months?
• What’s something that didn’t go well that you’d like to improve?
• Why are you on this team?
• What will make you stay on this team?
• What new experiences would you like to make in the next six months?
• How would you like to develop your career?

I generally recommend people-focused retrospectives only for teams that already achieved a high degree of trust. Only if people are willing to be vulnerable with each other does it make sense to discuss personal growth with everyone.

After each person adds their thoughts to the current topic or question, spend a bit of time discussing the answers. Try to identify common themes or disagreements while ensuring that people don’t go off-topic.

Here is an example of what the “How would you like to develop your career?“ could look like in a retrospective:

Check out this example template for Excalidraw to get started.¹¹ If you follow it, you may end up with a board looking like this:

After the retrospective concludes, one person should summarize the findings and discuss changes to project plans, team culture, or personal goals. Retrospectives are helpful to identify what went wrong in the past and what could be done better in the future. Without following up, the same mistakes will happen again, and issues will persist.

Weekly Schedule

When somebody gets stuck on a task in an office, they can turn around and ask a colleague for help immediately. Remote work adds friction and can slow things down. New hires and less experienced engineers often don’t feel comfortable asking enough questions and may also feel lost trying to prioritize their work. Putting together a schedule collaboratively makes teammates feel more involved and in control of their workload.

Experienced engineers usually have a daily, weekly, or even monthly schedule. They tend to have a pretty good idea for structuring their work, parallelize work to avoid being blocked, and stick with deadlines. Scheduling is a skill that often takes years to develop. Usually, I don’t care how people organize their work; I just care that they do. Quite often, I find that new hires or less experienced engineers struggle with this, not because they don’t know how to plan but because they never had a chance to learn from somebody at the same company how they should structure their work.

I start by asking for a schedule to be shared with me at first, or I may even show them multiple different methods that I’ve seen work (be it my own, that of a peer, or somebody they work with). I let them choose a process they’d like to try, and then I focus on getting them to stick with it for a while. Initially, I bring it up in every 1:1 meeting until I am confident that they own their schedule themselves.

Here are two methods I’ve seen work well:

• Use an actual calendar to plan out their rough focus for the next several months. Start by blocking off all holidays and vacation days, decide on priorities, and mark each day or week with one primary focus.
• Use a Kanban board with tasks and a rough duration and priority assigned to each of them.

The initial schedule doesn’t have to be completely accurate. It should be flexible enough so that changes can be made and communicated at any time. Again, I do not care about which process people follow as long as they have one that works for them. I’m not trying to micromanage people. I’m trying to help them manage themselves and their own time better – and the more of a mutual understanding we have of what is going on when working remotely, the better it usually is for everyone.

Asynchronous Decision Making

When working remotely, especially across time zones, never make decisions in meetings that require presence. Ideally, all decisions are made asynchronously via your preferred communication medium. Not only does this take pressure off video calls, but it also ensures that everyone has a chance to participate in the decision-making process. Think of people who feel uncomfortable speaking up in meetings or people who are naturally quieter. Text-based decision-making equalizes many of these differences instead of letting a charming but loud person steamroll everyone.

Asynchronous decision-making has the added benefit that it forces teams to document their decision-making process and the decisions that were made and why. Documentation makes it easier for new hires to gain context and for the team to look back at why something might have gone wrong.

Sometimes an exception has to be made, and you have to decide in a meeting. Make sure to share the possible options, trade-offs, and preferences ahead of the meeting so that everyone has a shared context.

Meet in Person

All of the above suggestions are useful when a team cannot work together in person. However, meeting up once every 3–6 months for social activities is still the most effective way to get a team closer together. There are two types of “offsites“ that I’ve been a part of:

• Experience focus: Team building exercises, hiking, climbing, playing games, going to a theme park.
• Open-ended agenda: Usually accompanied by a lunch/dinner and hanging out in a lovely space.

One of the problems with experience-focused offsites is that they tend not to be inclusive: People may not enjoy hiking, don’t like specific games, or have disabilities that prevent them from attending. That’s why I prefer open-ended offsites that have just enough content to get people excited but leave enough room to spark dozens of conversations. I like the ones that require traveling to a place: the time in a car or train with colleagues on the way there and back is unstructured and relaxed in a way that’s hard to recreate in other ways.

More often than not, one or more people will have personal reasons for not participating (and that’s totally fine!). Don’t make big decisions during offsites, and be mindful of what people might be missing.

Other Recommendations

There are a ton more ways to make everyone feel included. Here are a few more recommendations:

• Participation: Be aware of who isn’t participating and why. Ask in private and nudge them gently to raise participation rates. Be mindful of the difference between not participating for a good reason and not participating because they don’t feel confident speaking up. Exerting pressure to participate is never the solution.
• Consistency: Be consistent with how you are treating people. Don’t pick favorites, include everyone, and don’t make awkward comments if people aren’t willing to participate. Create a space where it is ok to decline things and don’t pressure people.
• Belonging: Make people aware of other groups that they should join. Ask them what they are interested in or direct them to groups they may belong to.
• Identify Opportunities: Many people don’t feel comfortable asking for things. Watch out for their needs and recommend them or sign them up for optional programs to help them with their career. For example, I signed many people up for English-as-a-Second-Language classes that meaningfully improved people’s verbal and written communication.

If you read carefully, you’ll find that all of the above recommendations build on each other. A weekly social meeting ensures that people get to know each other and build trust. Retrospectives require trust and help identify gaps and expectations. Mentorship structures can fill those gaps, all while gaining an understanding by sharing a bit of what is going on in everyone’s lives. A weekly schedule ensures that people know their priorities and stay unblocked.

In the ideal case, the above suggestions lead to teams where everyone has a voice, can participate in team decisions, make themselves understood, and feel a sense of belonging. If you are trying this with your team, please share the results with me!