How I Proposed a Remote Year to My Employer

This has been the most frequently asked question since I made my remote year announcement. It’s hard to answer on the spot because it’s been one hell of a process — a process that actually started in May 2017.

At that time, a good friend and coworker, Samvida Patel, had just returned from a year abroad. She had, one year prior, asked Integrative Nutrition to do the same thing — to continue her work as a member of the Admissions Team, while traveling with the Remote Year organization for 12 months. I asked to do the same and was sure my request would be approved, considering Samvida had done an amazing job. To my surprise, though, I was met with a number of objections and it was denied. I won’t bore you with their reasons why, but I will say this: I was told by upper management that it was poor timing and that I could ask again in the future. So, in my back pocket it went.

Fast forward exactly two years later (May of 2019) and I ask my employer the same question. Only this time, my process was entirely different. I had learned a lot after that first “no,” mainly — that it would be more about HOW I was to ask the question, than the question itself. If I can be honest, my initial proposal in 2017 was pretty weak. In fact, it wasn’t much of a proposal at all, but rather a short email thread between upper management, my immediate boss and me. I didn’t, by any means, present a solid case. This time around, I knew I needed to come back at them differently and that I needed to be more prepared.

So, I did my research and consulted a LOT of people, all of whom I seriously owe a coffee. I did extensive research on the Remote Year organization, to make sure that my employer felt comfortable with me in their hands. And I collected a lot of data, from both my marketing and operations teams, to support my question and to prove that my asking to work remotely was both legitimate and within the best interest of the company. I wrote up a proposal, developed a presentation and then called a meeting with the head of HR, the head of legal, the CEO and my immediate boss. No pressure.

Well, things sure were different this time around because I was greeted with a big fat YES. In fact, I don’t think I received a single objection. I was shocked, but at the same time, felt as though I had manifested this entire thing from the moment I decided to ask again. I have a lot to say about manifestation, but that is definitely for another blog post. Here, I want to share a little bit about my proposal and what I think worked in getting it approved. Hopefully there are some takeaways here for any of you looking to do the same.

Ya girl loves a list, so here goes…

1. Introduce the remote organization. Whether that’s with Remote Year or a similar organization, this initial first step is crucial. I was not asking to backpack through the mountains or to do this solo. I was asking to travel as part of a group of working professionals, with an organization that provides all the infrastructure necessary to continue my day-to-day work, such as 24/7 access to workspace & WiFi, living arrangements, travel & flight logistics, etc. I essentially said to my employer: they got me covered, so you don’t need to worry! I also made a point to highlight the application and acceptance process that I had to go through with Remote Year. RY doesn’t accept just anyone! They clearly saw the value in me as a professional, as well as the benefit that an experience like this would bring to a global company like Integrative Nutrition.

2. Explain the benefits of remote work, in general. While remote work may not be that new of a concept, it’s just recently become more of a mainstream thing. A lot of traditional companies may not be familiar with this concept and may even freak out at the initial thought of having some or all employees work remotely. I don’t necessarily blame them, in large part because there’s lack of information around the idea. Part of my job in proposing this question was to educate my employer on the benefits of remote work. Many traditional companies view remote work as a favor or a courtesy. And while that may be true in some cases, it’s so much more than that. By my asking to work remotely, I was planning on adding tremendous value to what we do as a company, at large. In many ways, I’m the one doing the favor. This was something they needed to understand.

3. Explain the benefits of remote work, as pertains to your company SPECIFICALLY. While you may have presented a good argument on the point above, your employer is going to want to see the tie in. They are going to want to know specifically how this remote role will positively impact the company. As mentioned, I love a good list. In my proposal, I presented ten solid business benefits. I titled this section “How Remote Year will benefit IIN.” One point addressed our prospective student body, which happens to span over 150 countries. We’ve only operated on Eastern Standard Time, thus there are large chunks of time where we’re failing to make connections with potential students. Having someone available during “off” hours will solve this problem. This section is by far the most important. To my point above, it proves that YOU are the one doing the favor here. It is not the other way around.

4. Have the data to back you up. When I mentioned I consulted a lot of people, I wasn’t lying. Members of my marketing and operations teams took the time out of their busy schedules to run a number of reports that I incorporated into my proposal. I’m truly grateful for all the help I received in accumulating this data. It’s one thing to say: “We miss a lot of phone calls overnight.” But it’s a completely different thing to say: “On average per month, 828 calls come in after business hours, 477 of which leave voicemails.” The second statement holds way more weight. That is a huge number of prospective students that we are failing to have touchpoints with, simply because of the time zone factor. Showing these numbers ultimately helped to validate my request.

5. Give yourself a pat on the back. Do not forget this section. This is where you talk about how and why you’re qualified to do this! In my proposal, I talked about my performance at IIN over the course of the last 3 years, how I’ve always exceeded my goals, how my quarterly & mid-year reviews have always been positive, how I’ve always been flexible with scheduling, how I’ve hosted live webinars and written for the company blog, how I’m a seasoned traveler who can handle an experience like this, etc. The list goes on. Come on, how often do we get to toot our own horn? To put it simply: sell yourself. Be proud of who you are and what you’ve done. Leave them convinced that you’re the girl (or guy) for the job! Without any doubt.

6. Wrap up with some important logistics. This includes things like cost (Remote Year fees are paid completely by me), check-in’s with management (I will be scheduling regular monthly check-ins with my boss and my progress will be tracked & monitored just as it is now), work related travel (if there are situations where I have to be on site, I will plan travel back), privacy (Remote Year networks are secure and I can connect to a VPN if necessary), safety (Remote Year is subscribed to International SOS, the market leader in security and emergency response), and whatever else you think they need to know! In this case, MORE is more. Over-explain all logistics so that no question is left unanswered. There is a reason I didn’t receive a single objection. I hit all points.

7. Also… Make sure to hyperlink everything in your proposal. This includes things like a link to the Remote Year website and their FAQ section. This makes your proposal interactive and directs your employer to resources that you may not have included directly.

So, there ya have it. I’m not a pro, but this is what worked for me. Yes — I presented solid information — but most of all, I think my employer was impressed with my follow-up, my persistence and the overall effort reflected in my proposal. My number one recommendation to anyone interested in doing this is to similarly reflect as much passion as possible into that proposal. It’s hard to ignore that.

I’ll wrap up by saying one last thing: There is tremendous power in asking for something that you want, even if you’re faced with a “no” initially. Nothing is ever final or permanent. When I was told that I could ask again, I did. And I advocated for myself much better than I did the first time. Sometimes when you do that, you just might get the answer you’re looking for.