My Remote Work Playbook

I have had a good balance of on-premise and remote jobs over the last four to five years. All my work experiences in India and New Jersey weren’t remote. But, after I started school in upstate New York, I have been working remotely at least once a year. Freshmen year, I worked remotely on my design project. Sophomore year, I worked remotely as a venture capital intern. Currently, in my junior year, I am working remotely with Assist.

All of these experiences have helped me design a playbook for working effectively on remote jobs. I am still iterating on it and seeing what works and what doesn’t.

The major problem with remote work is what I refer to as the Remote Work Paradox. If you don’t communicate obsessively and keep doing your own thing, your team might not acknowledge, appreciate and recognize you for your efforts. On the flip side, if you communicate a lot, your team might get annoyed and think that you don’t spend time doing the work.

This paradox is very difficult to tackle. Finding a good balance is the key to meaningful work and relationships with your team. Here’s a set of principles I try my best to follow –

Communicate obsessively

Yes, I know this is one of the things that I just said contributed to the paradox mentioned above. I have realized that it is not the excessive amount of communication that most people have trouble with, it’s the substance of what you say that could creates all the trouble.

Don’t send an email or message just for the sake of communicating or getting heard or feeling connected with the team. Think twice before hitting send. Is your message going to help the other person in any way?

It need not always be about their jobs or projects. Since you aren’t physically there with your team, it is important to get your relevant thoughts, ideas, opinions and feedback in front of them.

Get over the line of thought that you shouldn’t bother a person multiple times a day. If what you are saying isn’t worth communicating and if the intent is to just interact for the hell of it, just don’t communicate at all. But, if it’s something useful, something that could move the needle on a project, something that could further your colleague’s interests outside of work, something that could prevent the team from incurring extra costs, make it a point to communicate. People will appreciate your effort even if you are pinging them for the tenth time that day.

I do this by just embracing the fact that no one will ever know what and how I think if I don’t ask questions, respond with thoughtful answers, give feedback, and participate in discussions.

Be proactive and quick
One of the best ways of building relationships and earning trust is to be proactive. Perhaps, twice as proactive as you normally would be in non-remote jobs. The reason for doing this is quite simple. If people don’t see you working and progressing, they might be tempted to think that nothing is getting done on your side.

Being quick in responding and being first in voicing opinions in group discussions from time to time are subtle ways of building trust and giving your teammates peace of mind that you are executing.

It’s not just about delivering on your responsibilities, but delivering on them early. Do more than what’s expected. Strive to figure out what to do next, without being told to do so. Delight your team with good results that weren't expected of you.

Follow up on threads that you think are left abandoned. Help others do their jobs better.

Being proactive and quick in everything you do helps in reinforcing the reality that that you’re there, you have an opinion, and you are doing work.

This helps in establishing your place as a reliable and helpful colleague.

Understand the team

Each team has a set of unspoken rules about how they interact, collaborate, and make decisions. The sooner you figure those dynamics out, the better you would be able to do your job.

Figure out who talks the most, who talks the least, who is most thoughtful, who is very authoritative, how and when are meetings held, who really influences the team, who has access to all the documents you might need, who is most receptive to feedback, who sucks at written communication, who are good friends outside of work, etc. All of this gives you a lot of context you will use when you work and interact with the team.

It is very important to understand what sort of tools the team has in place for communication and collaboration. Learn about those tools. Embrace them in your workflows. Understand how each of your team members likes to be communicated on things. Some like Slack. Some like emails. Some like chats. Whatever it is, figure that out. And, adopt to that. If this means using five different tools for communicating with ten members, so be it. Don’t get hung up on what you use. Fixate on how to communicate the best.

Understand when each of your teammates like to be communicated with. Some people work in giant blocks during the day. Some work off and on. Figure out their work schedules and be mindful of them. Respect other’s time and priorities.

These three broad principles have served me well so far. I think I have gotten the higher level principles right. I am still learning about the specifics within each and how to optimize for each.

Here’s a piece I wrote on the notion of asking for permission to do something vs asking for advice to do the same thing after my summer working at betaworks —