When Managing Remotely is a Challenge

Or, how to keep the team engaged and motivated while working remotely

👋 Hello, and welcome to a new edition of Expander. I’m Abhishek, and each week I share the essential skills, frameworks, and practices you need to learn to grow in your career. Send me your questions and in return I’ll humbly offer BS-free actionable advice. 🤜🤛

To receive this newsletter in your inbox weekly, consider subscribing. 👇

If you find this post valuable, check out some of my other posts:

  1. How to prepare as your role evolves

  2. How to find the right metrics to measure?

  3. What is a product vision? How to create it? How to sell it?

  4. Don’t share your ideas with customers


Q: What are some good ways to keep the team engaged and motivated while working remotely? As the team grows, it is becoming a challenge for me as a manager.

I’ve got first hand experience of how it can be done well, and how it can go bad.

First, remote work is like solo travel, it’s not for everyone. Some folks get all their energy from face-to-face interactions with other people. Others are more comfortable working at their own pace and having minimum interactions and/or meetings. Like solo and group travel, both have their place in the world, but there’s no one size that fits all.

Second, if a remote org doesn’t actively focus on the culture, it goes south very soon. It happens in a non-remote environment as well, but the effect and speed is 10x faster in a remote setting—especially if it’s a growing company and people dunno each other very well. So, an org has to double (even quadruple) their focus on the culture after going remote.

Third, if done well, it can increase the velocity of the team tremendously. Employees are able to spend more time with their friends and family which (surprisingly) makes them better at their job.

Now that we’ve got that sorted, we have a couple of ways to attack this problem. First, it’s the tools they use and the way they work. Tools make a lot of difference, and most orgs don’t pay enough attention to them.

If everything is communicated through Slack threads, you need great writers in the team. Not all can express themselves via chat. To beat that, there’s Loom. Too tired to write? Not sure if the text expresses your enthusiasm? Just record a Loom and share it with the team.

Slack has also introduced a drop-in audio chat feature that mimics Clubhouse. If you have used Clubhouse, you know the value. If you haven’t, you should know that not everybody writes, not everyone records selfie videos, but everybody talks. It’s seamless!

The next step is to create better environments for working together. If your team was into whiteboarding when they were at the office, Miro is a great digital alternative to that. Zoom pairing sessions are also pretty useful. The team can simply sit and work together for a couple of hours—the same way they would had they been at office.

Apart from communicating and working together, the team needs to have some downtime together as well. But most team building sessions don’t work. Either there are too many people in a group or the topic doesn’t interest/engage everyone.

Instead of inviting the whole company together, it’s better to have multiple sessions involving random members of the org, thereby promoting cross-team interactions. A Zoom session consisting of 10ish folks tends to work great. Anything more than 20 is bound to go south.

To keep everyone invested in the session, you either need a good emcee or you can try something called Lean Coffee. It’s a famous method of group discussion where everybody suggests topics to discuss (for example, top Netflix thrillers, most embarrassing live events, something unique about your culture, etc.), the topics are upvoted, and the most upvoted topic is selected by the group for discussion. Other than this, there are several apps on the Zoom marketplace to play and have fun together.

Now, the most important parts (without which none of the above is gonna work): empathy, support, and overcommunication—in your day-to-day interactions.

The first step is to be extra kind towards each other and giving others the benefit of doubt, i.e., actually treating them as people instead of resources. One good that has happened because of COVID-19 is that it is now okay to share personal issues with the team—because more or less everyone has similar set of issues. Listen to them. Ask them what’s up with their personal lives. Share yours.

Other than hearing others out, few minor gestures can go a long way. Don’t forget to say “please” and “thanks” in your Slack messages. Encourage others to do the same. A lot of things can be misinterpreted in text if the emotion/intention isn’t clearly communicated. Double check what you write. If something can be misinterpreted, it will be.

Focus on overcommunication. Slack, despite all its usefulness, adds a tonne of noise. A lot of important things can easily be missed. So make sure to follow up twice to remind, recheck, and keep others accountable. Assume that mentioning something once won’t get it done. Always follow up! This will increase the velocity of the team, and reduce overall frustration. You won’t have to do it for long. With time, they’ll catch up.

And lastly, double down on 1-1s and pulse checks with your team. Do them every week. Find out what’s going on in their lives. Ask them how can you support them better. Discuss how can you work with them more efficiently. Listen to them. Make them feel heard.

But don’t just listen, take actions. If they voice their concerns and nothing happens—no action is taken—they are bound to lose faith from the team and the manager. Never ever let this happen, no matter what. Have extremely high standards in this regard. It takes a lot of time and effort to build trust, but it can be lost in a jiffy. Don’t give it away.

There’s nothing passive about management. You have to be actively on the lookout for whatever is affecting the team—both good and bad.

To be honest, the job is simple: treat your team as people and as you compatriots, not resources; work with them and make sure they are accountable and heard; maintain a good balance between work and fun. It’s not so tough, but it ain’t easy either. All the best!


This week’s newsletter is brought to you by The Sunday Wisdom.

The Sunday Wisdom is a newsletter for people who want to get better at thinking and decision making. It contains a wide range of useful ideas—in the form of original articles and videos, bite-sized wisdom, book reviews, article recommendations, quotes, and more. Check it out!


Share Your Thoughts

Do you agree with what I said, or do you think otherwise? Share your comments, counters, and questions. Also, don’t forget to share how you would approach today’s problem. Use the comments!

Until next week,
Abhishek 👋