How to maintain a good relationship with your boss while working remotely

Throughout my product management career, my bosses and I had to work remotely from each other. Working for small, early-stage Israeli startups, where I was the only Product Manager, meant that my boss, the CEO of the company, had to be in New York City to make the business global.

There are definitely advantages and disadvantages to having a remote boss. First, you get to become independent, which is an important trait for a product manager. Second, you become more concise, because, for the short time you have your boss on the phone or on video call, you need to get all the information across fast. However, sometimes, having your boss in a different time zone can be frustrating and can cause tension.

In this post, I want to share a few tips that can help you maintain a good relationship with your boss while working remotely, be it due to COVID-19 or because your boss is located in a different country. Some of these tips could also help you even if you’re co-located with your boss, they’re good practices to pick up anyhow.

1. Your one-on-one sessions are sacred

Although I’m sure your calendar is already busy with meetings, this one meeting is probably the most important one on your calendar. Your one-on-one meeting with your boss is your anchor — this is a guaranteed time in your week when you have your boss’s undivided attention. However, the busy schedule of a startup company can make it easy to cancel those one-on-one meetings because it affects the smallest number of people, and it’s also easy to neglect to reschedule it.

• If your one-on-one got canceled, reach out to your boss and ask to reschedule. She will be impressed by your dedication and motivation, and you can still get your anchor time for questions and deliberations. If you have access to her calendar, maybe even suggest a specific time that she’s available at.
• If you see that your meeting gets canceled week after week, reach out to your boss and explain why this meeting means so much to you, and try to understand together why it gets pushed every week. Maybe the originally scheduled time is not a good one?

2. Maintain a list of things to discuss

During the week you’re probably working on many projects, having multiple meetings and conversations with people, and it’s easy to forget things that were mentioned to you while doing other things. This means that you’ll not take full advantage of that precious one-on-one time with your boss and you might need to wait a few more days before you get answers to your questions.

• To make sure you come prepared for your one-on-one sessions, try maintaining a list of topics you want or need to discuss with her. I use Todoist as my go-to app because it’s easy to enter items quickly even during meetings or on the go, and it’s so much fun to check things off when I’m done with them.
• It will also make your boss impressed that you came prepared for your one-on-one session, and it will make better use of your limited time together.

3. Let her in on the decision-making process

One of the hardest things about working remotely is that it’s a lot harder to discuss, brainstorm, and make decisions together. When your boss is in a different time zone or location a lot of times they can’t be part of the discussion, and while you went through the entire process of thinking and eliminating solutions, they only hear the final result from you.

• When you share a decision you made with your boss, it’s important to help them understand the thought process you went through when making this decision, including which solutions you eliminated and why.
• By allowing your boss to understand your thought process, you’ll help them feel more confident in your solution and your skills because it gives them a glimpse at how you face challenges.

4. Be her eyes and ears in the office

Working in an office environment means you are interacting with multiple people daily. If your boss worked in the same office as you, you’d have many conversations during the day, and she would know what the general discussions going around the office were. When working remotely, these things become significant because they paint a full picture of what the team is working on, what are the challenges, and what’s the general vibe around a specific feature.

• Try giving your boss daily updates, make sure she knows you are protecting the group’s interests and that you’re doing your best to achieve your common goals.

5. Send a weekly summary email

This idea was given to me by a mentor when I was trying to improve my relationship with my boss. Every Thursday, at the end of the day and just before I left for the weekend, I’d send my boss an email summarizing my week: What I did, what I still need to finish, and what I’m going to work on next week. My boss really loved and appreciated these emails, it gave him a simple place where he can go back to if he needs to, and it also made him feel like he’s in the loop. It got to a point where if I missed sending the email one week, he would send me a message and ask why I didn’t send it. It was just that helpful.

• Send your boss weekly summary emails, indicating what you worked on this week, what still needs to be completed, and what you’re going to work on next week.
• This will give your boss clarity to your tasks, their progress, and this can also be a place to ask questions that popped up since your last one-on-one.

6. Think ahead, be prepared

Your boss has a lot on her mind, pressure from her bosses, from management, or maybe even from investors if she’s a founder in the company. The best thing you can do for her is to make sure you’re her ally, make it clear for her that you’re here to help her just as much as she’s there for you. That’s why it’s so important to stay in the know of what’s coming.

• Ask about future plans so you can help her be prepared. If for example there’s a quarterly meeting coming up where you always have to prepare a presentation, offer to help her get started, remind her of how much time it usually takes so she knows to be prepared.
• Offer to cover low hanging fruit so she has less to worry about. Knowing you are her ally will make her trust you more and will make it easier to assign you more challenging tasks because she’ll know she can count on you.

Do you work with a remote boss? Think I missed something? Would love to hear your best tips!