How to Ask Your Boss to Work From Home

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You want to ask your boss to work from home. Maybe you have some recent changes in your family like the birth of a new baby or an aging parent has moved nearby. Maybe you’ve recently moved or your office has relocated and you’re now spending 3 hours in the car commuting. Maybe you’ve simply realized that being in the office all day, every day is simply not conducive to you doing your best work. Whatever the case, you’re interested in a little more flexibility and are ready to have the conversation. Easy right? Not always, this can be a daunting and intimidating topic. Here are 10 tips for this conversation:

  1. Frame it in a way your boss will understand and find value in. This is #1. Highlight how this new work set-up will benefit your company. Yes, companies want their workforce happy and healthy but what they most want is productivity and a good bottom line. Think about what your manager most values and show how some flexibility will help your team and company achieve this.
  2. Keep personal gains out of it. Yes you’ll have the opportunity to walk your dog more and will be able to throw in laundry in between meetings. This a personal benefit that your manager does not, I repeat, does not care about. Keep this out both because it doesn’t present any value add to your manager, in fact it might suggest that you will be spending more time with your pooch or keeping house than working.
  3. Consider what’s appropriate and realistic. All companies and teams are different; some are keen on flexibility some are not. You know your company and manager so spend some time thinking about what is a reasonable request. Maybe your firm will respond best to one day a week, or a month, or an afternoon after you have a doctor’s appointment. Spend some time thinking about what’s a reasonable amount of flexibility and pith that.
  4. Prepare for the conversation. Don’t wing it. If you have regular check-ins this is an appropriate time to bring this up; if you don’t (you should and that’s a different story..) ask for a check-in to talk about your role. Do it behind closed doors and come prepared with a specific plan (based on what you feel is appropriate and reasonable) for your boss to react to.
  5. Don’t demand an immediate answer. No one likes to be put on the spot and you never know what meeting or conversation a person just came from Don’t make your boss feel as if she has to make a decision right then and there; in fact if you make it clear that you want her to think about this and get back to you. She’ll likely appreciate the time to mull it over, especially if this would be new for your team or if she mat have to run it past her manager.
  6. Suggest a trial period. Particularily if this would be a new step for your company suggest starting with a short, trial period. Identify a window of time and schedule a check-in at the end of this period for you to discuss how the flexible set-up is working.
  7. Work hard. If you get the yes you’re looking for that’s great news, but that doesn’t mean it’s time to coast. In fact it’s the opposite; you need to prove to your company that you can handle this responsibility and your work won’t be compromised. Said differently: don’t slack off. Work hard, post results, show that flexibility doesn’t take away from your productivity but enhances it. You must be responsible and disciplined for your success here.
  8. Be flexible. Since you’re asking for flexibility you need to be flexible. In my experience this can mean coming even last minute even if I had planned to be at my home due to a last minute client meeting or a presentation. Especially if you’re in a trial period you need to ensure that your schedule is accommodating and flexible, since it won’t go over well if your new flexible schedule makes it harder for work to get done.
  9. Prepare for a no. Some companies, some teams, some managers simply don’t like remote work. No is an answer and if you ask for something you need to be prepared for it. If you get a negative response don’t wallow but keep on doing your thing. And while you do this…
  10. Think about how important flexibility is to you. If you’re reading this blog you likely have some interest in work flexibility (or you’re my mom–hi mom!!) If you bring it up to your boss you clearly have interest in it. If your manager shuts down the idea or you know your company simply won’t go for it, I’d encourage you to spend some time really thinking about whether this is something you want or need to be successful–and most importantly, happy–in your job and life. If it is then it may be time to consider a role that offers you the flexibility that you desire.

Workplace flexibility is a growing trend that can benefit a company and team in big ways. What else have you found to work (or not work) when asking for a flex-schedule?

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