There are a lot of managers who are not comfortable letting their employees work from home. But more and more employees want a flexible work schedule. This episode is dedicated to helping you show your boss the benefits of working from anywhere and going “Remote First”!


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Original transcript

Welcome to the Collaboration Superpowers podcast. My name is Lisette and I’m interviewing people and companies doing great things remotely. Hello, everyone, and welcome to episode number 118. Today, I want to talk with you about another really popular thing that people ask me about all the time, which is how do I convince my boss to let me work from home. As we all know, there are a lot of managers out there who are not comfortable with letting their employees work from home. But more and more, people want to do it. So how do we convince our managers that it’s a good idea and can even be beneficial for the business?

So for my first batch of tips, I went to the Work At Home Success Guru, Leslie Truex. You can hear her interview in episode number 91, and she had some awesome tips for how to convince your manager to let you work from home. And the first thing that she says was start by quantifying what you’re doing. So make a list of all the different things that you work on and then make a list of how you quantify your productivity on those things. Easier said than done, I know, but it’s a great place to start.

Next, you have to really start thinking about what’s in it for them. How will you, working from home, or anywhere, benefit them? That’s going to be your key argument right there and I think the most important tip out of all the tips that I’m going to be giving today. Zig Ziglar, a great salesman, calls it WII FM Radio, what’s in it for me radio. Always be thinking about the value that you can deliver for your employer and how you’re going to increase that value by working from anywhere.

The third thing that Leslie recommends is to anticipate some of the problems and then come up with the answers to that. How will your colleagues know what you’re doing? Probably, the most obvious question that’s going to come up. So come up with answers to that. How will you make yourself available? How can people reach you? So take some time to really anticipate what the problems and questions are going to be and come up with answers to that. It’s a great exercise before going to your manager.

The next thing that Leslie recommended, actually, was really smart, which is take a look at what your official telecommuting policy is at work, if you even have one at all. A lot of people simply just make arrangements and agreements with their direct managers. But if then the 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 perceptive. And then for those that do have a telecommuting policy that’s already in place, take a look at what that offers because sometimes it can open up some options you haven’t thought of. Some people do like a flextime schedule. Some people shift the hours, so you could do later or earlier schedules. Some people allow one day a week, and on and on and on. There are many different variations on telecommuting policies.

Now if your company doesn’t have a telecommuting policy in place, one thing that you could do is try to spearhead the creation of one. And the way to start there would be actually to study what some of the other flexible work options are that other companies offer.

Okay, so those are the rock star tips from the awesome Leslie Truex. Again, you can listen to her interview in episode number 91, and I highly recommend it.

Some of the other interview tips that I’ve picked up from other people are to start slow and be proactive. Now by starting slow, it could be working one day a week. It could be working just an afternoon a week. Start very slow because 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. So it’s definitely not something you want to speed into. Take it slow and handle the problems as they come up. Can’t go wrong there. And a very slow way to start would actually be to introduce the concept of remote first in 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, for example, when there’s really bad weather and you can’t get to the office or when there’s a transportation strike or when the commute is just jammed like it sometimes gets in London or in Los Angeles, for example. When a company goes remote first, they are less vulnerable to outside influences, which is always a good idea. Chris Ridgewell, whom I interviewed in the very first episode of the podcast had some really good advice about this for companies. And he even mentioned the fact that insurance companies will give businesses lower rates on their insurance when they can prove that they’re remote first. So actually, there are clear business incentives for doing this, and it’s just a matter of time before this catches on in more and more places.

Okay, but in your preparations for going remote, one of the things that you can try doing is creating a team agreement with your team so that when you go remote, everybody knows what’s going to happen. Now I talk extensively about team agreements in episode number 42, but basically, the team agreement is a guide to behavior. So you outline what kinds of information you’re going to be sharing, how will you be communicating with each other, and how do you know what each other are doing. And when you can answer those basic questions on a team, then where you work starts to matter less and less because you have this guide to behavior. Okay, so check out episode number 42 for that. And it’s also offered as one of the sessions in the Work Together Anywhere workshop. So if you really want to go in-depth, then definitely take the work together anywhere workshop, and you’ll learn a lot more about creating a team agreement there.

Okay, but in addition to a team agreement, you’ll also want to set up feedback loops because when we work remote, we don’t bump into each other, and we tend to lose context. So building and feedback loops is a very wise process. You can learn more about feedback loops in episode number 40, but essentially, 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. I explain the merit money system that the Happy Melly team uses also in that episode number 40. But regardless of which methods you choose, the most important thing is to actually implement the plan.

Okay, so the last tip that I’m going to give is a little bit far out for most people, but I think it’s a really fun one, which is to try telepresence. For about $500 U.S., you can purchase a Kubi, which is a Revolve Robotics telepresence robot. And it allows you to beam in just like on Skype and move yourself from side to side and up and down. And the movement is important because it kind of humanizes you for the person that’s in the same room with the Kubi. But 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, put a Kubi robot at your desk and then just beam in from where you are so that they can see that you’re around. It works really well, it’ll show your dedication to the cause, and it opens up a whole, new form of office humor, I promise you. All right, so if you’ve been trying to convince your boss to let you work from anywhere, I hope today’s episode has given you some great tips for how to start and division for the road that you’ve got to go down.

To recap all the tips quickly one more time, quantify what you’re doing. Focus on how working from anywhere will benefit your manager. Anticipate problems and have answers to them. Check out if you have an official telecommuting policy at work. If you don’t, study other flexible work options and see what’s available. Start slow and be proactive. Introduce the concept of remote first in your organization. Create a team agreement. Put feedback loops in place. And if you’re daring, try telepresence. And if you manage to convince your boss to let you work from anywhere, please let me know. I would love to interview you for the podcast. You can find all the great ways to get in touch at And if you really want to become a remote-working pro, try one of the Work Together Anywhere workshops offered all over the world in person or online, which I highly recommend. I mean if you want to learn how to work online, the best place to do it is online. So check out those workshops at A big thanks to our ever-organized podcast producer, Nick, the podcast monster. You can hire him to make you a star at

And another gigantic, brilliant thanks to our dazzling graphic designer, Alfred Boland. You can hire him to make you look cool at All right, everybody, until next week, tune that radio dial to WIIFM and be powerful.


Podcast production by Podcast Monster

Graphic design by Alfred Boland

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