How to Ask to Work from Home – 11 Steps to Convince your Boss

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Working from home can be life-changing in so many ways. It can mean more leisure time and less commuting, and gives you the ability to work in comfort and safety. It could perhaps even grant you the freedom to live somewhere you’ve always dreamed of.

One option, of course, is to specifically seek out a home-based position. This site has lots of information on that (and you could perhaps start with our list of companies that employ remote workers.)

But what about if you already love the job you do, but want to switch to remote working? That’s what this article is all about. It lays out exactly how to ask to work from home.

Why Listen to Me?

I’ve been living and breathing home working for nearly 20 years. In my last role before starting to work for myself (back in 2002!) I was involved in rolling out both the technology and the policies to facilitate home working for a large organisation.

Since then I’ve helped numerous companies with their home working arrangements. And to complement that experience, my family has “walked the walk” too. In 2009, my wife successfully convinced her company to allow her to work not just from home, but from a completely different country.

There’s some comment from her later in the article, and from others I’ve assisted with this process.

Has Everything Changed?

2020 has seen many people suddenly become remote workers, without even having to think about how to ask to work from home!

Many large companies have already said that they will continue to allow home working, even after the Covid-19 pandemic has abated.

As such, there’s a strong argument that there’s never been a better time to convince your boss to let you work from home.

However, this doesn’t mean plenty of companies aren’t already keen to drag everybody back to the office. As we will discuss in a moment, it’s now MUCH easier to find strong arguments for home working. But that doesn’t mean you won’t still have to make a strong case.

So with that in mind, let’s get started.

How to Ask to Work from Home: The 11 Steps

1. Do Your Research

Before you decide exactly how you’re going to persuade your boss to let you work from home, you’ll need to do lots of quiet research in the background.

I suggest starting with your HR policies or staff handbook. Is there already a policy around flexible and remote working? Are there already staff allowed to work from home?

Once you’ve learned all there is to learn about the remote working situation in your own company, it’s time to look wider. Do your company’s competitors encourage home working, for example? You can always look on job boards and sites like FlexJobs to give yourself an idea of industry trends.

It also makes sense to gather some hard data to support your case. Things like

  • How much time do you spend commuting, and what does that add up to each month and each year?
  • How much is it costing the company to provide office space for you? (In some large cities you can be looking at $10-15,000 per year, per employee).

The better you prepare, you more you are armed to make your case.

2. Get Your Timing Right

You can potentially blow your chances of a home working arrangement if you don’t time things right.

So don’t ask when there’s a big project deadline on the horizon, or when your boss is extremely busy with something. Don’t ask if you’ve recently missed a deadline or made a mistake!

The best time to ask is when stress levels are low, and you’re ideally in the leadership team’s good books.

One note on this, however, that’s particularly valid at the time of writing: Coronavirus has forced many people to work from home, and companies are currently making big decisions on their remote working strategy for the future. This could, therefore, be a golden opportunity to speak up.

3. Have a Conversation – Don’t Just Send an Email

I strongly believe that a request to work from home is something that should be raised face to face (or at the very least via a phone or Zoom call).

You’ll certainly want to follow up in writing – either with a formal proposal or to clarify detailsBut this is the kind of thing that needs the personal touch, and that will differ hugely from person to person, company to company, and boss to boss.

Some websites out there even provide a template email for how to ask to work from home. This seems bizarre to me, because it ignores the simple fact that every company is vastly different in culture and hierarchy.

It’s REALLY easy to say no to an email. You’re looking to begin a negotiation, not ask a one-off closed question. 

4. Be Ready to Address Objections

Managing objections is something salespeople are taught – and essentially you are selling the idea of working from home to your boss.

So you need to be ready to respond when they say “but what about xxx?”

Some examples:

“How will I know you’re working and not watching Netflix?”

“I would hope that my output and efficiency will speak for itself. I’d be more than happy to do this on a trial basis so I can prove to you that I will get at least as much done as I can in the office.”

“I’m not convinced your specific job could be done remotely.”

“Recent events have seen all kinds of professionals, from doctors to personal trainers, find ways to effectively work online. I’d be delighted to produce a formal proposal detailing exactly how we could make this work. We could start out on a trial basis, and I would, of course, be happy to come in to the office for any specific tasks that require me to be there “in the flesh.””

“How can I be sure I’ll be able to get hold of you?”

“I already have access to Slack on my phone and am consistently efficient in responding to messages. My home internet connection is reliable, and there’s no reason why I’d be unavailable. I’m sure that, after a short trial, I’ll be able to convince you that I’ll be just as available as I would be across the office.”

The kind of objections that will arise are likely very specific to your particular company. As such, some time pre-empting what the objections might be is time well spent.

5. Suggest Starting Slow

There’s no need to “go for gold” and aim for a full-time home working arrangement from day one.

A pattern I see over and over again is employees starting off with an agreement involving one or two days per week. This is a much easier “sell,” and you can then aim to expand on it over time.

So long as you perform well and don’t abuse the trust placed in you, this can be a great way to address objections as you go. Once a boss realises you’re still a dependable employee when working from home, they have little reason to object to letting you do it all the time.

If you can negotiate working from home for just a day or two per week, and then excel at what you do, you will typically find extending the arrangement REALLY easy.

6. Prepare Examples

It’s wise to go in with some solid examples of your reliability and commitment. Examples of where you have worked well from home before are ideal here.

This brings us back to how the Coronavirus crisis has gifted employees with a golden opportunity to ask to work from home. If you are one of the millions of staff who has now worked from home during lockdown, you should hopefully have some great examples of when you did a fabulous job despite not being in the office.

Examples of where you truly benefitted the company without going anywhere near the office are what you really want.

Think: “We closed that sale when we were all working over Zoom,” or “I completed that project ahead of time while I was home-based.”

“Keep it simple – show the benefits to everyone. Give practical examples of how the arrangement will work – and how it will save the company money.” Louise T – negotiated working from another country in 2009. 

7. Sell the Benefits

If you’re thinking about switching to working from home, you’re probably focussed on the ways it will improve your life. But your company will be far more preoccupied with how it benefits THEM.

As such, have some benefits in mind – for the discussions you have and for any formal proposal you may write.

Some examples:

  • The cost of office space is considerable, and many Financial Directors will suddenly be painfully aware that they’ve had to continuing paying for it while the team all worked from home. There’s a genuine cost saving to allowing home working.
  • If you commute an hour each way every day, that’s ten hours per week during which you could be working and being more productive.
  • The Covid outbreak isn’t over (at the time of writing), and social distancing rules apply. Staying away from crowded environments is good for your health, and your team’s health.
  • Plenty of job roles are genuinely easier to perform in an environment free of distractions. Home working could notably improve your productivity.

8. Demonstrate your Flexibility

It’s definitely a little easier to work out how to ask to work from home nowadays, but it’s still important to remember that your boss is under no obligation to say yes.

In the early days, you should be willing to bend over backwards to prove that the idea is workable and beneficial for all concerned.

So, if they say they still want you in on Wednesdays, agree to it even if you think it’s daft and unnecessary. Let them set certain conditions to begin with, if it’s what it takes to kick the arrangement off.

I’m not suggesting being a pushover, but my experience has taught me that getting some kind of remote working arrangement in place is the toughest hurdle. Once you’re in a position to demonstrate that everything works just fine when you’re at home, adding on extra home-based days and tweaking the arrangement is really easy.

9. Suggest Bargains and Review Periods

I’ve talked a lot about trial periods. They’re important for several reasons: They allow you, and your employer, to confirm the arrangement works. They also give you a fixed point in the future to expand on things.

You could, for example, agree to working from home for two days per week for three months, with an agreement that it will increase to four if everything goes well.

There’s other bargaining you can do too. Say, for example, that you do spend two hours per day commuting. You could perhaps suggest that you work for the period between 8 and 9am that you would usually spend in the car or on the train.

You still get to work from home, avoid the commute, and get five hours per week of your life back. Your company gets five additional productive hours of your time too. That’s surely not too shabby for anybody concerned?

One additional factor worth thinking about here is pay negotiations. I wouldn’t suggest offering to take a pay cut in exchange for being allowed to work from home. Really, this undermines any argument that you can work just as effectively remotely. However, if there genuinely is a part of your job that you won’t be able to continue doing, your salary package could become part of the negotiation.

10. Know your Fallback Position

You should never go into a negotiation without knowing your desired outcome AND your fallback position.

Most importantly, do you intend to stick around if your company turns down your request to work from home?

Is it more the case that you’d ideally like to be home-based all the time, but would still be very happy with working remotely a couple of days per week?

You need to know the answers to these questions. You certainly don’t want to burn bridges and render yourself jobless if you don’t get what you’re asking for. However, it’s wise to know what you WILL do if that happens.

Perhaps you could simply stay put but actively start seeking a new role at a more progressive organisation. As our article on fully remote companies proves, there are plenty of them.

11. Get it in Writing

As soon as you’ve successfully negotiated your home working arrangement, make sure you get it in writing. This could take the form of a new contract or a contract amendment.

Not only is this common sense, it protects you in the long term. If you don’t do it, you run the risk of future changes ruining your arrangements.

I’ve seen this happen in the past. A company takeover, for example, can result in a new management team switching away from remote working. If you have a formal agreement, your company will need to continue to honour it, or agree some kind of compromise deal with you. With no documentation – well – it could be straight back to the office for you.

Success Stories

As I said at the start, I’ve been involved in remote working “culture” for many years. If you’re good at what you do there’s a good chance that you will be able to agree something with your employer by following this advice:

“I signed up for HomeWorkingClub in early October. I just wanted to let you know that due to your informative articles, I’ve approached my boss at work. As of January, I will be a stay-at-home employee at my current company. (I work for a non-profit homeless shelter in grant writing and fundraising).

I just wanted to say thanks for the push.” Janet Keller.

Let’s also not forget that by following our own advice, my wife and I were able to spend some wonderful years living by the sea in Portugal, while she still did her old job, working entirely remotely.

It CAN happen – just make a plan and follow it!

Summing Up: The Key Points

  • How to ask to work from home isn’t rocket science or some dark art. It’s just like any other business negotiation.
  • Preparation is everything: think about the questions your boss will ask and the objections they might raise, and be ready to respond to them.
  • Be prepared to start slow with a part time arrangement. Once you’re doing some of your work from home it becomes much easier to prove that the arrangement works.

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