118 - How To Convince Your Manager To Work Remote

These days more and more employees seem to want to go remote, mainly to work from home. Although offering employees the remote option can be just as beneficial for the business as it is for the employees, it’s still difficult to convince managers of that. 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.

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Make a plan for going remote

What would you want to be sure of before agreeing to an employee working unsupervised?

  1. QUANTIFY WHAT YOU DO. Work at Home Success, Leslie Truex, says to list out all 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 that you will demonstrate just how trustworthy—and indispensable—you are.
  2. STAY IN “YOUR BOSS’S SHOES” MODE—what’s in it for them? The legendary salesman Zig Ziglar calls it WIIFM radio: What’s In It For Me radio. When working up your pitch, think about the value you already deliver to your employer and then consider how you’re going to increase that value by working outside the office.

How can you go about thisLook at all the reasons you want to work remotely. Maybe you can’t stand the commute. The value for them could be increased work time: you could offer to work every minute you would have been commuting. Perhaps you simply have to make it to the daycare center by 5:30pm, but would happily put in extra hours after dinner. There are also the distractions at work—people stopping by to speak to you. By the end of the week those distracting moments really add up and take away from your productivity.

  1. ANTICIPATE THE POSSIBLE OBJECTIONS—and then counter them with proactive solutions. Probably the most obvious questions that are going to come up are “How will your colleagues know what you’re doing? How will you make yourself available? How can people reach you?”
  2. LOOK AT WHAT YOUR OFFICIAL TELECOMMUTING POLICY IS. Does your company have one at all? Many people simply make arrangements and 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 does have a telecommuting policy in place, make sure you know what it offers because it can open up options you haven’t thought of. From flexible schedules to shifting hours or days, there are many different variations on telecommuting policies.

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

  1. START SLOW AND BE PROACTIVE. This could mean working one day a week or maybe just one afternoon a week. When we go from being co-located to remote, there are a lot of things that we can’t anticipate, and just by nature, it changes the culture of the company. It’s definitely not something you want to speed into. A very slow way to start would be to introduce the concept of remote first to your company, which basically means whether or not you work remotely, you have the processes in place to be able to work remotely if the situation necessitated it, e.g. bad weather, a transportation strike or when the commute is just jammed like it sometimes gets in London or in Los Angeles. When a company goes 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 that they’re remote first, which is great incentive.

How to prepare for going remote

  1. CREATE A TEAM AGREEMENT. When going remote, it’s a good idea to create a team agreement so that everybody knows what’s going to happen. A team agreement is a guide to behavior where you outline what kind of information you’re going to be sharing, how will you be communicating with each other, and how you will know what each other is doing.
  2. SET UP REGULAR FEEDBACK LOOPS. Setting up feedback loops is also essential because when we’re independently located , we don’t bump into each other and we tend to lose context. Feedback loops can include things like retrospectives, which you come together and do as a team, one-on-one sessions with the manager, and then also setting up some sort of 360-degree team feedback loop.
  3. TRY TELEPRESENCE. Not the cheapest way, but for about $500 USD you can purchase a Kubi, which is a Revolve Robotics telepresence robot. It allows you to beam in just like on Skype and move yourself from side to side and up and down. Movement is important, as it’s a way to humanize you for the person that’s in the same room with the Kubi. If your boss is truly worried about whether or not you’re going to be around when you’re working from home or from anywhere, a Kubi is a great way they can see that you’re around.


More convincing resources

91 – Be A Work At Home Success With Leslie Truex

29 – Work Where You Are Most Productive With Teo Hären

42 – How To Create A Team Agreement For Your Remote 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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Graphic design by Alfred Boland


Work Together Anywhere Workshop by Collaboration Superpowers

Individuals, Podcast
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