118 - How To Convince Your Manager To Work Remote

With a growing desire for work-life balance, working remotely has gained momentum since the covid19 pandemic. The benefits of remote work are the freedom to choose one’s workspace, eliminate the commute, and spend more time with family. Most people want the freedom to create the work-life balance that works best for them, whether that’s working from home or at the office.

Although offering employees the remote option can be just as beneficial for the business as it is for the employees, convincing your manager to embrace the idea of remote work can be challenging. So how do you persuade your boss to give remote a try? By putting together a thoughtful plan where you put yourself in your boss’s shoes.

Measuring and Demonstrating Your Productivity

DOWNLOAD THE REMOTE-READY CHECKLIST. Download and complete the Checklist for Convincing Your Boss (or Team)

UNDERSTAND WHAT YOU NEED TO BE PRODUCTIVE. Start by knowing what you need to be productive. Consider creating a Personal User Manual.

  1. To clarify for ourselves so we can design our lifestyles around the important things to us, and
  2. To help others understand us better to collaborate more effectively.

QUANTIFY WHAT YOU DOWork at Home SuccessLeslie Truex, says to list the different things you work on and then consider how you can measure your productivity on those things. Essentially, you’re asking your boss to trust you. So identify all the ways you will demonstrate how trustworthy—and indispensable—you are.

When working up your pitch, think about the value you already deliver to your employer, and then consider how you will increase that value by working outside the office.

MAKE YOURSELF INDISPENSABLE. As Cal Newport writes, be “so good they can’t ignore you.” Make yourself an essential part of the team to have some leverage to work with.

STAY IN “YOUR BOSS’S SHOES” MODE. The legendary salesman Zig Ziglar calls it WIIFM radio: “What’s In It For Me radio.” What’s in it for senior leadership? What would you want to know before agreeing to an employee working from home?

ANTICIPATE POSSIBLE OBJECTIONS. Counter any objections with proactive solutions.

  • How will you make yourself visible to your colleagues?
  • How will the meetings you participate in be better, not worse, because you are remote?
  • How will people know what you are doing or how to reach you?

LOOK AT WHAT YOUR OFFICIAL HYBRID POLICY IS. Does your company have a policy about working outside the office? Many people make agreements with their direct managers. But if that manager ever goes away, then that telecommuting policy that you’ve had needs to be re-evaluated with somebody else who may not be as receptive.

If your company has a telecommuting policy, make sure you know what it offers because it can open up options you haven’t considered. Telecommuting policies vary, from flexible schedules to shifting hours or days.

If your company doesn’t have a hybrid policy, think about spearheading the creation of one or study what other companies offer.

SPECIAL OFFER: If your company has a hybrid work policy that you can share, I will send you a deck of virtual meeting cards in exchange!

CREATE A TEAM AGREEMENT. Ask the team to define the information they need for their projects, the communication protocols necessary to get their work done, and the tools they need so that everyone knows what the other is working on. Some questions include:

  • What information do we need to share? Where is it stored?
  • What tools are we going to use to communicate?
  • What are the expected response times?
  • How do we know what each other is doing?

Download our Team Agreement Facilitator Guide and Canvas for instructions and inspiration!

SET UP REGULAR CHECK-INSFeedback loops can include retrospectives, one-on-one sessions with the manager, and a 360-degree team feedback system with the entire team.

START SLOW AND BE PROACTIVE. This could mean working one day a week or one afternoon a week. When we go from being co-located to remote, there are many things that we can’t anticipate, and just by nature, it changes the company’s culture. It’s not something you want to speed into.

BE WILLING TO EXPERIMENT. Try different setups as trials/experiments. Set aside time to discuss if your mutual expectations were met.

PUSH FOR CHANGE. Introduce the concept of remote first to your company, which means whether or not you work remotely, you have the processes in place to be able to work remotely if the situation necessitates it, e.g., bad weather, a transportation strike, or when the commute is just jammed like it sometimes gets in London or Los Angeles. When companies go remote-first, they are less vulnerable to outside influences, which is always a good idea. In some cases, insurance companies will give businesses lower rates when they can prove they’re remote first, which is a great incentive.

JOIN A WORK TOGETHER ANYWHERE WORKSHOP. Or even better, suggest a Work Together Anywhere workshop for your team and learn how to deliver the same results online as you do working in the same room together.

Work Together Anywhere Workshop by Collaboration Superpowers

Podcast production by Podcast Monster

Graphic design by Alfred Boland


More resources

Convincing Your Boss (or Team)

91 – Be A Work At Home Success With Leslie Truex

29 – Work Where You Are Most Productive With Teo Hären

42 – Create A Team Agreement For Your Team

133 – Superpower Hour: Feedback On Virtual Teams

131 – What Does A Remote First Company Look Like?

48 – Telepresence! Why I Welcome Our Robot Potential




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