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.

Popular search terms for this article:

how to ask to work from home, work from home email to boss, work from home mail to manager, work from home request email, asking to work from home, request to work from home, work from home email, working from home email, working from home email to boss, work from home letter to manager

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 and following the trail of virtual bread crumbs from there.


  1. Dan Davies on the 25th May

    Sadly my bosses are clueless when it comes to this “working from home nonsense.”

    The usual reply is that it doesn’t follow health & safety rules. Ignoring the fact they would probably get about 1 / 2hrs a day extra work form its staff.

    Add to the fact that we’re a web design company too.


  2. ciara on the 25th May

    I am very fortunate that my boss allows me to be flexible and work from home when necessary… for example when I started my job my 9 month old was diagnosed with Asthma. Over the past 3.5 years she has had some severe attacks but I lucked out, my company helped me set up a VPN so I could access files in work from my Mac at home. It was a win win for me I was able to give my daughter the treatments she needed and not lose a day of pay.

  3. tattoo jow on the 25th May

    From my own personal experience working from home is great , if you’ve got a family and you’re not alone the whole time.. otherwise it can turn into a bad habit 🙂

  4. Tahsin on the 25th May

    Working from home is also related to the nature of job. I am campus manager and i need to be there daily to take care of my campus 🙁 Those who are able to work from home r the lucky pplz. Have fun guys.

  5. JP Giunta on the 27th May

    Working from home is successful when the boss is confident about his or her ability to manage a department remotely and the worker is self-disciplined enough to maintain a high level of performance. This article did an excellent job of pointing that out.

    Additionally, management needs to understand that productivity should be measured by results not time spent at the workstation. Many ineffective bosses are more comfortable when they can see people sitting at their desks rather than working remotely.

    Good sales managers, for example, realize that sales don’t happen in the office; they happen on the road. Nevertheless, there are some managers who insist that staff spend more time in the home office. They also go on sales calls with their highest performers and generally hover over their sales staff like a Socialist looking for a Capitalist with money.

    Working at home will never catch on until managers learn how to lead not police workers – not an easy task for insecure bosses. And, as the writer pointed out, workers must project a professional attitude and get a reputation for getting the job done. Otherwise even good bosses will be reluctant to expand work at home opportunities.

  6. Paul on the 27th May

    I have a function (staffed by about 22) which is a prime candidate for telecommuting. Some of the team have successfully demonstrated in the past the ease with which they can be productive from another location. Indeed, when someone needs to take the day I often find that they will go the extra mile and I wind up getting even more net hours of labor.

    These are college education professionals with years of experience under their belt and in our industry they are best of breed. I trust them implicitly and have deep visibility into their production metrics to ensure my trust is not misplaced.

    I’d send them all home right now if I could. But I can’t. Yet.

    The reasons why are worth considering for anyone thinking of putting together a case to telecommute. Any of my team who comes in here with a researched answer and suggested solutions to MY issues jump to the top of my list of telecommuting candidates.

    Here are some of the questions I need to get resolved to make this happen.

    Who pays for the internet access ?
    Does the associates employment contract need to be rewritten ?
    Do the goals and objectives that an associate have need modification ?
    Does the internet access need to be upgraded ?
    Can I mandate that the employee comes into the office at short notice in the event of a workload volume problem or crisis situation ?
    If the internet access fails is the employee required to come to the office ?
    Whose responsibility is troubleshooting and fixing IT related issues ?
    Are there business contracts necessary so we can get SLA’s from Comcast etc. ?
    In the event of a minor failure that needs desktop support who pays for shipping or transporting the computer or technician to and from the remote site ?
    Who owns the computer ?
    Whose insurance covers damage ?
    Who pays for the phone charges ?
    Does the home network support my advanced phones?
    Is there a need to place a VPN concentrator ?
    Who’s fault are those noisy kids in the background ?
    Do we need to send our ergonomic consultants to examine the workplace to prevent liability for RSI claims etc ?
    Who pays for any upgraded furniture that ergonomic study reveals ?
    Will the employee be tempted to work when they are ill rather than take a sick day?

    and so on and so forth . i have a stack of these questions that I am researching with HR and Legal at our company.

    Anyone who really wants to make this happen for themselves will research these matters with the right parties , present case studies of successful implementation , and present a proposal that addresses as many of the questions above as possible.

    If you are clever enough to put together a proposal that gets your manager further along AND STILL make it seem like his idea you can start planning which pajamas to wear to work.

  7. Nate on the 9th May

    Paul, if I may take a go at your questions.

    1) Easy: you already provide an office with internet access – if they want to use something somewhere else, that is their decision, especially since you don’t require them to work at home. Remember, they are the ones asking – not you.

    2) Not sure what would need to be rewritten…

    3) If your employees are more productive from home, the it proves the ‘office’ theory wrong. Raising goals could actually be counter-productive (though not necessarily). Raising stress for a work-at-home situation would in-turn bring the employee back to your office, and now you have to pay for them to use your site (water, heat, electricity for computers, etc…)

    4) see #1

    5) That’s a downfall of work-at-home situations. If there are enough situations per day/week that justify their presence that would have to be accounted for. If you’re asking the question out of fear, there are always ‘what-if’ scenarious that can be generated.

    6) How often does internet fail? In my house I have not had one day in 6 months, whereas at my office, it’s at least once a month…

    7) IT and Troubleshooting – another cost/effective analysis. How often are the occurances? See #5

    8) See #1

    9) Depends on how far your remote worker lives. If your office is in Portland, Maine and your remote worker is in San Diego, is a different issue than 20 minutes away (average commute distance). Also, instead of the IT guy coming from outside into your office, outsource someone locally in your remote-worker’s area – you could probably save money…

    10) You do of course. You have to make agreements that anything contained on that computer is property of your company. If they want to start their own competitive business using your computer, you can take the computer at any time. Again, if you’re afraid of your employee using the computer to look at facebook, then I would revert to #3, if your employee is less productive, then you don’t allow it

    11) Reference #2

    12) Get creative – Skype/Google chat/etc. If they’re sales then they probably have a company cell anyway. The money you’re saving on their electricity and toilet flushing at the office could be directed there

    13) If not, then that’s a hinderance, but I’d be suprised if theres not a call forwarding feature built-in to your advance phone. An account I frequently deal with has this already set up (company is in So. California and works from Montana)

    14) Probably, but I’m sure this could be worked out. Many companies are moving to entirely remote and there are solutions out there.

    15) The children of the parents in the cubicle next to them… who always have a comment for everything

    16) Maybe something the employee must demonstrate before hand – contractual agreement. If they work from home, you are exempt from claims…

    17) see #16

    18) Possibly, but how many days have you gone to work when you should have stayed home…

  8. Mark on the 26th July

    Hi! I have tried a lot and never made any money. I wondered is there any real work from home jobs, not Internet scams? Is it possible to make money from home for real?
    Until I have been involved in the Social Financial Network called – mmm2012.

    Idea of this scheme is genius and it’s totally legal.
    For the second year running, I got constant profits for two years now.

    It’s one of the best money making ideas recently. Community banking – people start to help each other by helping with money directly.

    Testimonials, legal and financial aspects, you can find at our team’s website: We are just a small (little more than 1000 people), successful part of this network. Total network boasts more then
    35 000000 people.

Add a Comment