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How To Convince Your Boss to Let You Work Remotely

I know most folks assume that if they are going to get a remote job, they’ve got to hit the virtual pavement and start looking for new employment.

Not true.

Some of us LOVE our current jobs and don’t want to leave, we would just prefer to do our current job from where ever we want.

Most people don’t even consider proposing remote work to their existing employer because they assume the answer will be “no” or they haven’t even considered it as an option. I came to tell you today that is IS an option and, while I can’t guarantee you will get a “yes”, I can give you some tips to increase the likelihood that you will get one.

How Lib? Well, by baking a Portability Pie.

A Portability Pie is a framework I designed for a course I offered that teaches people how to approach proposing remote work to their employer. The Portability Pie consists of four key areas you should have buttoned up before you broach the topic at work:

  1. Remote-ability
  2. Champion
  3. Brand Capital
  4. WIFFM

I go into a lot of detail about these key areas in my course and even provide an evaluation tool that gives you a probability score, which estimates your probability of getting a “yes” to working remotely. But for purposes of this post, I’m going to give you some quick details about each of the key areas:


This questions seems like a “duh” but I have to ask. Can your job ACTUALLY be done remotely?

This goes beyond just the question of whether or not most of your work is done via computer. You also need to consider:

Do you have a lot of client interaction? If so, would your clients be comfortable meeting with you virtually?

How much security is required for you to do your work? In some cases, you may have access to very sensitive information. Note that this does not mean you absolutely cannot work remotely, but it does mean you’ll have to be thoughtful about how you ease this concern by researching the types of security measures you can take to keep sensitive information safe.


You honestly need to have a champion for ANYTHING you’re trying to do at work – be it getting a raise, a promotion, or proposing remote work.

What is a champion? Well, think about the days of old, like Game of Thrones. A champion was a warrior who would fight on behalf of someone else, usually someone that could not fight for themselves. Quite often, the decisions that are being made that affect our careers are happening without us in the room, so we cannot fight for ourselves. You need someone in that room who has your back, who has influence, and who is willing to speak up for you. You need a champion.

The main characteristics of a great champion are:

  • Someone who has decision making power or buy-in with decision makers
  • Someone who really understands the organization you work for
  • Someone who cares about people

You should have a great relationship with your champion. This person could be your boss, your mentor, or someone at the office that you admire. In either case, I want you to take a second to think of at least one person at the office that you would feel comfortable asking for help with your proposal at work. If you can’t think of anyone, you’ve got some work to do.

You need to identify a champion and start building a relationship with them. Note, the way to do this is NOT to rush in and bombard by asking for their help. This is sort of a long game. You start by setting up some time with this person and getting to know them and letting them get to know you.

The likelihood of you getting your proposal to work remotely approved without a champion is incredibly slim. This is a very important element of your Portability Pie.


Whether you know it or not, you are a brand at your place of work. You may not even be trying to brand yourself at work but rest assured, you are a brand.

Your brand is who you are perceived to be among your coworkers and superiors. Your brand is developed by the quality of work you do, how you interact with people, your persona at the office, the way you dress, and a number of other things.

Your capital is how much you are valued at your company based on your brand. You can think of it as how much leverage or “spending power” you have at your office. How many “favors” can you “buy” with your brand. This will be huge in determining what your company is willing to do for you.

I break brand capital down into four elements:

  1. Value – how much are you valued at work? You can determine this in a few ways: How often are you consulted for your opinion on things by leadership? Do you have specific skills that no one else has? Are you considered the expert in the area you work in?
  2. Rating – what is your actual rating at work? What did your last evaluation say about you? If you are getting high marks on your evaluations, then it’s clear that you’re an asset to the company and they are very likely to want to keep you happy to retain you.
  3. Trust – How much does leadership trust you? Are you being micromanaged or does leadership trust you to take projects or important workstreams and run with them? If your company can trust you to do great work without much oversight, it’s a much easier sell to propose to work from anywhere away from their watchful eyes.
  4. Proof – Do you have any proof that you are an effective employee? Do you consistently drive results? Do you meet deadlines? Are you high-performing? Even better is having proof that you have effectively worked remotely, even if it was just those two days that you weren’t feeling well so you worked from home rather than coming to the office and infecting everyone else with your germs@


WIFFM stands for What’s In It For Me. Pat yourself on the back if you already knew that.

WIFFM is the final area of your Portability Pie. I believe it’s the one that will tie everything together and make your proposal to work remotely much more effective. In fact, WIFFM can be applied to anything you are proposing.

Most people approach asking for something the absolute wrong way. They lead with what THEY want from the deal.

Please DO NOT go into your boss or your HR telling them you want to work from anywhere so you can spend more time with your kids or travel the world and then stop there. Nothing wrong with sharing your reasons with them but the fact of the matter is that they don’t care about your reasons . Your reasons benefit YOU not them. So you will have to paint the picture of why it benefits them. Because they will be sitting through your proposal thinking “what’s in it for us?”.

And there is plenty in it for them!

  • Studies show the average work from home employee works a total of 2 more days than employees at the office
  • Studies also show that employers save an average of $11,000 per year on remote employees
  • Increased morale means increased retention

Those are the key ingredients to your portability pie. I hope you are now considering more options to working remotely. I know this can seem a bit daunting but let me help you ease into it. Here are 3 actionable steps you can take RIGHT NOW to get you moving towards getting a yes to working remotely:


  1. Research – Find out if your company has a remote or flexible schedule policy. Find out if anyone at your company has a flexible schedule.
  2. Test the Waters – The next time you have a dr. appointment, you aren’t feeling well, or you kid needs to stay home from school, don’t take the day off. Instead offer to work from home. This will help you build proof that it can be done!
  3. Mind the Gaps – Go through each of the key elements I mentioned above and identify the gaps you have. What ingredients are you missing from your portability pie? Write them down and build out a plan to close those gaps.

I’ll be doing a workshop on this and talking to some HR professionals on this topic at the Quit Commuting Conference in August!

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