Want To Work Remotely? How To Ask The Tough Questions

Not my pretty face, but the cleavage is similar...

About a year ago, I accepted an on-site, part-time position at YourTango, despite misgivings about resuming the dreaded NJ-NYC commute I had left behind several years before.

I was desperate, though. I needed some regular income to supplement the other work I was doing, and I was also badly in need of some quasi-regular human contact. Happily, I ended up enjoying my work at YourTango so much that the commute didn’t seem so bad. Plus, I loved the people I was working with.

Still, it eventually began to wear me out. It ate up my time. It was expensive. And, after almost a year of doing it, I began to resent it.

So at the tail end of September, I requested a new, remote working arrangement and, several weeks later, they approved it. Now, I work with my three cats laying in a semicircle around me. I sleep in a little bit more. I dabble in yoga and take daily walks. I have extra time to work on my other projects and extra time to make plans with… well… other human beings. Once again, I feel like I’ve achieved a healthy balance.

Maybe some of you are a little bit like me. Maybe you have full-time jobs, and squeeze in your freelance work in the evenings and on weekends. Or perhaps, like me, you have a part-time gig, and have to commute in to an office. Maybe you often think to yourself, man, I could totally do this job from home, and it would totally free up some extra time for my personal projects! But you’re afraid to ask permission.

How do you go about proposing such a fan-flippin’-tastic work arrangement to your big-time scary boss?*

Well, I used e-mail. Because, as we all know, I’m better in writing.

Still, I’m sure this would work just as well if you opted to go the verbal route.

But basically… don’t beat around the bush. Admit to your superiors that you’d like to make a request to work remotely. Then, follow it up with a pitch they can’t refuse. And don’t make it about you. Talk about how your working remotely would benefit them. Use words like “efficiency” and “resources.” Companies love that. Give examples of how similar work arrangements have worked in the past, if you can. Convince your superiors that having you work remotely would be better for… everyone!

In the event they react with hesitance, suggest a trial period (one month?), a compromise (once-a-week face time?) or both.

And above all, make it clear that you’re not trying to pull back from the company. Some employers might take a request to work remotely as a sign that you’re operating with one foot out the door. Convince them otherwise. Be frank about how much you love working for them, and about how appreciative you are of the opportunities and experience you’ve been given.

If you make your case well enough, they should have no (sane) reason to turn you down.

Need some help putting together your own request e-mail (or fantastic speech)? No problemo! I’ve actually put together a freebie e-mail template for you that you can download here. It contains the bare bones of the ideal request letter, in addition to suggestions for the extra details that can really make a letter sing.

And as a bonus, I’ve also put together a resignation letter template. Because maybe you want to take that plunge. Maybe you want to say sayonara to your full-time job, yet still leave on such good terms that your former employer continues paying you on a freelance basis, or recommending you to others. It could happen. It happened to me!

I hope you find these templates helpful or — at the very least — entertaining. (Maybe both?)

Feel free to share your own request success stories in the comments!

*Disclaimer: My superiors at YourTango are not at all scary. Rather, they are as sweet as apple pie. And they have pretty hair. And cute shoes, too. But they do mean business.


  1. Letter writing templates – what a great idea, Stephanie. Not everyone is as good at writing as you are. I’m sure the two templates you’re developed for this post will be very helpful. Will there be more?

  2. I think this is a great idea, too. Also, are you planning to be available to help people personalize their letters even more?

  3. Steph, I loved this post! The advice about making it clear you’re not trying to step back from the company is spot-on. And love that you offer templates–that’s often the most overwhelming part of it.

  4. Dear Supreme Overlord:

    Fantastic post. Another idea is to suggest having in-person meetings with your immediate superiors at regular intervals. If included in your pitch (and if you’re sincere about the commitment), this may help tip your employer in your favor — or at least convince them you’re serious.

    And I love, love, love these templates. 😀

  5. Steph, the nice thing about telecommuting is that some of the tangential things that bug you about your job (the long commute, the chatty coworker who won’t let you get work done, or the ridiculous dress code) fade into the background and you can focus on work. When I left my last job, I resigned in person to my boss and let him know that I’d be willing to finish up some of my projects in a freelance capacity. That would help ease the transition for both of us and allowed me to leave on a positive note, since I’d helped the company out.

  6. I think it helps to have already proved you are a self starter, too. I don’t know why companies want people in the office, honestly. They’d all save a lot of money if they just had conf room space and no offices and had people work from home.

  7. great post.

    and great idea on the template letters (i’m going to put my marketing director/revenue generator hat on for a second and say, “offer them up free for a month, send out an email, write an article for BNET about how to put your WFH request into words, get people to the templates for 30 days…and then charge to download the templates. $25 a pop is more than worth it.” alright, i’ll stop.)

    i requested a working more hours at home when my daughter started first grade this year. i wanted to be home for her when she got on and off the bus. i also wanted to spend more time doing my work writing assignments in the comfort of my home-office during the evening hours when i feel at my most productive and/or creative.

    i wrote up a memo that bullet-pointed how this would benefit my work: more well-written articles, newsletters, etc., more creative ideas to put in the hopper, happier employee. i asked to meet with my boss and gave him the memo while i had it in front of me while i went over everything.

    i also did this with my maternity leave a few years back so that instead of coming back five-days a week, i came back three days and worked two days at home for three months after my 8-week maternity leave.

    there’s another template letter: maternity leave extension request.

    thanks again, this is good stuff.

  8. What a great, helpful idea, Steph. I’m like you – much, much better on paper than in spoken words. Glad you were able to find a good balance for yourself.

  9. Way cool! Although my work situation is already very similar to yours (including taskmaster cat companions), I just know your amazing templates are going to inspire someone to take that extra step and join the wonderful world of us at-home workers.

  10. Steph, this is such a fascinating topic. My husband & I, both tech writers in Silicon Valley (until I went into independent editing a couple of years ago) have been dealing with this issue for over ten years now through multiple companies.

    Ten years ago, telecommuting was on everyone’s horizon. It makes sense: you focus on the work, as Susan says, and the whole culture of, “I’m bored in this cube & looking to be distracted,” disappears. Plus, the company’s overhead drops when they don’t have to provide a workspace, furniture, office supplies to the extent that (at least in Silicon Valley) they’re happy to pay for your travel to the occasional meeting and keep you in a good computer. And your carbon footprint goes down when you’re not sitting in traffic ever single day to and from the office. Best of all, when they’re not clocking your hours in your cube, the only way they have of measuring your work is by how productive you are–so they get more productivity than they ever expected.

    Things were good for everyone.

    But then the war started and the economy began sliding, and when people are afraid they become paranoid. Suddenly employers were panicking about freeloaders, and telecommuting jobs dried up. My husband and I still managed–it was either that or move back to Silicon Valley–but we had some rough times.

    Now it’s getting better again. The war is over, the economy is improving, the fear is lightening. And this time, we have the massive blogosphere to facilitate inter-office communication: Skype, Google Docs, blogs, Twitter.

    There is no question that telecommuting is a benefit for both employer and employee. After the era of the endless cubicle day, we’re all getting our lives back.

    It’s the future.

  11. Hi,
    I know this is an old post, and I am actually not a writer I am designer ( not super gifted with words like you are). I found this via google search. I wanted to know if you have any advice or would consider writing a template for a cover letter asking to work remotely from the get go. Any ideas for tactics I could use to convince a job poster to higher me as a freelancer in the interim when they are looking for full-time help or as a telecommuter when the job doesn’t specify? Any help or resources appreciated!


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