How to Ask Your Boss to Work From Home


I’m writing this article from home – where I’d love to do all of my work.  Much of my writing is done here, but my day job doesn’t afford me the ability to enjoy the same “luxury.”  That’s not to say I don’t do some of my work for my day job at home – that does happen from time to time.  Actually, the separation of the two pursuits makes not only for a clear set of responsibilities depending on where I am (for example, I can leave my work at the office should I choose), but it makes for more productivity on the whole.

But many of you have one job.  One that you could do just as easily from home.  One that you know you could do better from home.  So why not do that?  How can you go from working at the office to working at home?  Here’s a step by step method to get your boss to say “yes” to your request to work from home…

Establish Trust

You may have been at your current employer for a while – and if you’ve been in your current position, even better.  Gaining the trust you’ll need to have in order to pull this off shouldn’t be as difficult as it will be for some.  Timothy Ferris of The Four-Hour Work Week points out that this should be done in small steps regardless…so the trust you have (or will have) established is key in getting the process of working from home underway.  You’ll know your situation best – and you’ll know deep down whether or not you have the trust of your boss to a level that enables you to take it to the next step.

Think Small First

You’ll be tempted to go all out at first – after all, you’ll be excited that you’re even considering the notion of working from home.  You need to take this slowly.  Again, since you know your work situation best, decide whether or not shorter work days is the approach you should take or if you should ask for one less day in the office per week.  The latter is the most ideal, because it opens doors to asking for additional days down the road.  Shaving hours off the workday only gets you so much further in terms of productivity.  Explain to your boss that an entire day at home will work best – but if you know that won’t fly start with less hours per day at the office.  As your productivity increases, you’ll be able to ask for more as the results of the experiment work in your favour.

Get To Work

You’ve managed to convince your boss that you can work just as (if not more) effectively from home.  Now do it.  Show them you were right.  Prove it to them on an ongoing basis.  No slacking.  This will require discipline.  Set office hours for yourself.  You’re at home to work, so keep your eye on the prize.

Go Back To The Well

One day at home has proven to be successful – now go back and ask for more.  You’ve got a precedent your arsenal now, so that should help your cause.  Again, don’t get greedy.  The worst thing you can do is overestimate the situation because you’ll likely end up back where you started.  Knowing when to ask for what is a delicate matter.  Don’t lose sight of that.

If All Else Fails

None of this may work in succession – or at all.  If you’ve miscalculated your boss’s willingness to allow you to work from home, you’re going to be facing an uphill battle going forward – because your boss may sense an apparent unhappiness on your part.  It’s likely a perception, but we all know what they say about perception.  You’d better be sure about your status in the workplace before pursuing this – or be sure that you may not want to be there in the long run.

Things To Keep In Mind

  • Be prepared with a list of how working from home will benefit your boss and the organization (lowering carbon footprint, no commute means more time to work, morale boosting, less downtime, etc.).
  • Be ready to move on.  This could all go over like a lead balloon if you’re not prepared – and have misread your working situation as well.
  • Be sure that you have all the fortitude needed to work from home.  Some people need to be at an office to do their best work.  Some people prefer not to bring their work home, regardless of how passionate they are about it.
  • Be ready to work.  The success of the venture is all on you and how you make it work.  Be ready to take that on.
  • Be dressed for work.  A Skype video conference call won’t go over so well if you’re in your pajamas.

Working from home can be the ideal situation for many of us – and for the companies we work for.  It can be the ultimate win-win.  Just remember that what looks good on paper doesn’t always look good in practice.  Telecommuting can be the best way to be more productive at what you do…as long as you tell yourself that it’s up to you to make that happen.


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Mike Vardy an editor on Work Awesome. We could tell you where his personal productivity parody site, Eventualism and all of his other projects reside on the web, but you'd be best served going to Vardy.me and following the trail of virtual bread crumbs from there.

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