We’ve got some big news… 🌱 Know Your Team is now Canopy →

How to have a good relationship with your boss when you’re working remotely

Four best practices to help you work well with your boss when you don’t see them face-to-face all the time.

What does her Slack message *really* mean?It’s easy to second-guess yourself when your boss pings you. You want to have a good relationship with your boss — but it’s not always the most natural of things. And that difficulty only increases when you’re working remotely.

When you don’t see your boss face-to-face all the time, the room for miscommunication, misinterpretation, and misalignment expands. You can’t read body language. You can’t go tap your boss on the shoulder to ask a question. You can’t even show her with your physical presence that you are, yes indeed, working.

Yet maintaining a good relationship with your boss is crucial. According to Gallup, “managers account for at least 70% variance in employee engagement scores.” You’re less stressed when things are going well with your boss — so you want to be particularly thoughtful about managing that relationship while you’re remote.

The good news is that this is a common scenario faced by 1,000+ managers in The Watercooler, our online community for leaders from all over the world. Based on their conversations, I’ve pulled a few tips on how to maintain a good relationship with a manager while working remotely

Proactively share progress

For your manager, understanding what progress you are making on your work is surprisingly opaque. Your manager is often juggling quite a few tasks — be it working with a client or negotiating a partnership — and they want to know what you’re working on ideally without having to hover, check-in with you constantly, be “Big Brother” about it. As emphasized by leaders in The Watercooler, this desire to know what you’re working on is only heightened when you’re remote.

To help shine a light on this for your manager, proactively share as much detailed progress as you can. This can come in the form of writing up a bit more granularly in your bullet points in your weekly summary about the project. Or it can come in the form of you even volunteering that you send her a daily summary of what you accomplished that day.

Helping your manager understand the results you’re achieving brings them a ton of ease and peace of mind to their job.

Quick tip:  Know Your Team is perfect for helping you proactively share progress with your boss. Our Heartbeat Check-in helps you share with your boss, automatically, what you’re working on each day. Be sure to check it out here.

Play detective about their working style

Working well with someone has a lot to do with understanding how they like to work. What are their preferences and habits? What’s the way they’re used to having things done? As a remote employee, not seeing your manager face-to-face, it’s very easy to unintentionally annoy your manager or do something that isn’t within their zone of what they’d prefer. When you know their working style, you can better calibrate from afar how to communicate with them, work with them, and deliver above and beyond what they expect.

To get a sense of their working style, here are some questions you can ask them:

  • What do you value most in a coworker?
  • Who in the organization do you admire, and why?
  • Do you like time to think something over, or do you prefer to talk about it right away?
  • When do you not like to be interrupted during the day?
  • Are you a morning, afternoon, or a night person?
  • Is there anything you feel like you might be a little more particular about than most?
  • What, if anything, worries you or keeps you up at night about the company?

Try asking one (or more) of these questions during your next one-on-one conversation, when your manager asks you, “Do you have any questions for me?”

Rigorously clarify expectations

Arguably the most challenging part of any working relationship — regardless of if you’re remote or not — is to get on the same page in terms of expectations. Do you know what is expected of you, and does your boss know what is expected of her? Often times, when you’re both in-person, these expectations can be hashed out over time: You listen, observe, learn, ask others around you, and pick them up. But when you’re remote, because of limited in-person interactions, those conversations might not come up as readily. Accordingly, it’s imperative for you to ask questions that clarify, uncover, and confirm what these expectations are.

Here are some questions you can ask your boss to start to clarify these expectations:

  • What things will I need have accomplished this year for you to view me in this role as “successful”?
  • What does quality work look like to you?
  • What should standard working hours be for both of us?
  • What is the best way to contact you during those hours?
  • What form of communication should be used to communicate with you during that time?
  • What’s the expectation of how quickly I should respond when you reach out to me during those working hours?
  • What form of communication do you prefer when there’s a hard topic or conversation? (E.g., In writing, over the phone, video call)
  • If I need your attention on something urgent, what form of communication do you prefer? (E.g., Slack, an email, a phone call)
  • What do you consider “urgent” versus “not urgent”?
  • If I have any feedback for you, how would they prefer you receive it: In writing, over the phone, or during a video call?
  • If I have a suggestion about something, how would you prefer you receive it: In writing, over the phone, or during a video call?
  • If I have a questions, what form of communication should I pose the questions to you? (E.g., In writing, over the phone, during a video call)

One Watercooler member also recommended to have a small cheat-sheet with remote communication expectations with best practices like:

If you are going to be offline to take care of some personal things during the day, please notify your direct team on their Slack channel.

If you are planning to work at odd hours schedule for a few days please let everybody know up-front.

Make time to get to know them — in person or over video

When you work in the same physical location as your boss, the opportunities to build trust and rapport are plenty. You can chat with them over lunch and ask them about their hobbies, or go grab coffee in the afternoon and catch up what’s been going on in their life recently. Even bumping into them in the hallway of the office and giving a friendly “hello” fosters a sense of affinity between the two of you. When you’re remote, those moments of social interaction no longer exist. For managers who are working with remote employees for the first time, this is often a shocking and noticeably absent part of a boss-employee relationship.

In the Watercooler, leaders had some recommendations to make sure you’re still getting to know your manager on a personal level (feel free to suggest them as ideas to implement with your manager):

  • If you happen to live nearby your manager, try quarterly in-person lunches.
  • Once a month or once a quarter, have coffee over video for 30 minutes to an hour to chat about life. (Here are some icebreaker questions if you’re never really sure what to talk about or what to ask your manager.)
    Video is always on for calls (unless there is a tech reason)
  • Take a few minutes to catch up on life during the beginning of a one-on-one meeting.
  • Twice per month, during your one-on-one meetings over video, chat about whatever they want to talk about. It usually covers a bit about work or maybe just catching up on what is happening in their lives.
  • Do video chats instead of just calls. Many Watercooler members recommended this. They often ask that people turn on the video and “it makes a huge difference.”

While never easy, focusing on these four areas as a remote employee can help better your relationship with your boss tremendously. If you want, you can even use this article as an excuse to start the conversation and perhaps try a few of these ideas. (For example, you could send an email saying: “I read this interesting article about working well remotely, and thought we might want to try turning on video more often instead of just doing phone calls…”)

These tips have worked for our Watercooler members — I hope they work for you too.

Know Your Team is software that helps you to become a better remote manager. We help you run effective one-on-one meetings, get honest feedback, share team progress, and build team rapport. Try Know Your Team for free, yourself, today.

Additionally, we are giving away our Guide to Managing Remote Teams – 60+ pages completely for free. Based on data we collected from 297 remote managers and employees, our CEO, Claire Lew, wrote 11 chapters of best practices on how to manage a remote team. 

You might also find these articles helpful…

Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.