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Learn what you can do to start working at home instead of the office.

What Can I Do To Work At Home? – 5 Steps To Convince Your Boss To Let You Work Remotely

Are you wondering, what can I do to work at home either permanently or even temporarily? Are you unsure how to actually go about asking your boss if you can start working from home? In this blog post, I outline a 5-step system you can follow to set yourself up for the best possible chance for your boss to agree to let you start working remotely. 

One of the most common reasons that a boss will say no to their employees working remotely is because they are worried about potential roadblocks, bottlenecks, or challenges in terms of workflow. 

It may even be that they hold a strong belief that office collaboration and a buzz of activity are good for company morale. 

Whatever their reason, you have yours too, and so you want to set yourself up for the best possible chance of getting a YES from your boss. To do this, I highly recommend getting prepared for the meeting before you even ask your boss for the meeting.

Step #1 – Prepare For The Meeting

How will your working remotely benefit the company, the department, or your boss?

As with everything in life, one of the top questions we all ask is, what’s in it for me? Therefore, it will be extremely beneficial for your request to outline how this will benefit your boss, your department, or the company as a whole.

The answer to this will vary highly depending on the industry you work in, the position you hold, and many other factors.

If you want some ideas about how working remotely can benefit your employer, check out this blog post.

Create a remote working game plan.

Next, you will want to have a detailed plan to present within your pitch that will outline how you will manage your tasks moving forward, how you will maintain the necessary communication and anything else that is relevant to your industry and position.

It is important to remember that your boss’s time is valuable too, so you don’t want to go into the meeting with a 30-minute description of how you will do every little aspect of your job. Instead, try to group like tasks together, create general summaries, and focus on how you will do your most high-level tasks.

Create a plan to help show your boss how working from home can work for all of you.

Prepare evidence of how working remotely can work in your industry or position.

If you will be the first one to work remotely permanently within your company or department, it can be difficult for your boss to understand how that would work long-term. So, to combat this, you can prepare evidence to show how this can work.

Try networking with other individuals in your industry to see how they manage their work remotely. This can be done in person or online via Linked In, Twitter, etc.

Identify potential concerns and come up with solutions in advance.

Don’t give your boss a reason to say no! Instead, identify as many potential concerns as you can, and come up with viable solutions before you even go into the meeting. This will show your boss that you are resourceful, creative, and willing to work with them to find solutions to the problems or challenges that you may encounter. 

Remember, it is extremely important that this benefits the company as much as it benefits you, and the solutions should reflect that as well.

Brainstorm your answers to any objections you think your boss may have. 

Your boss may have some objections, and it can be really helpful to you to brainstorm what these may be in advance and what your responses will be. 

You can even take the extra step and practice answering these objections in the mirror or with a friend so that you can practice how you will speak your thought clearly and concisely. 

Consider your boundaries and where you are willing to be flexible in advance.

While this is not something you will present to your boss, it will be beneficial to determine in advance as there may be some negotiation that takes place in the meeting.

For example, are you willing to work remotely part-time and come to the office part-time? Are you willing to take a pay cut? Are you willing to pay for the software you will need to maintain communication, manage your workflow, or track your time yourself?

Having the answers to these questions in advance and knowing your boundaries will help you address them should they come up during the meeting.

Once you have prepared for the meeting, it is time to schedule the meeting with your boss.

Do you have questions about whether you should take a pay cut for remote working? Check out this blog post for some tips and advice on this hot-button topic.

Step #2 – Schedule A Time To Speak To Your Boss

When you reach out to your boss, make sure you are clear about the purpose of the meeting and the time you will need. This shows respect for their time.

Within your request to schedule a meeting you can even highlight one of the benefits for your boss, the department, or the company that you outlined in the first step. This can help to pique curiosity on their part and open them up more to the conversation.

#3 – Prepare Mentally For The Meeting

It can be extremely nerve-wracking to have this conversation with your boss, so it is important that you prepare mentally for the meeting in advance. This will help you show up with confidence.

Start by reminding yourself why you are doing this. You can use this reasoning to anchor yourself during the meeting if you are starting to feel anxious or nervous. 

You can also eat or drink something that comforts you before the meeting starts. 

And remember, it is perfectly normal to feel uncomfortable during your meeting. Just take deep breaths and focus on why you are doing this and how it will benefit you and the company. If you focus on that, what you say during the meeting will reflect this.  

Get in a good mental headspace before asking your boss if you can work remotely.

Step #4 – What To Say During The Pitch Portion Of The Meeting

Presenting Your Pitch

When you start the meeting, you will want to outline everything you prepared in step one including: 

  • What’s in it for them?
  • The remote working game plan
  • Evidence of how this can work in your industry and/or role
  • Solutions to potential problems or challenges

It will be extremely important to remember during the meeting that your boss’s time is valuable, so plan your pitch accordingly. 

You can touch on each of these topics in any order that feels good to you and in an order that reflects the type of working relationship you and your boss have with each other. 

The time you give to each point will also depend on whether you have worked remotely before, the top objections you think your boss might have, and what points you think will be the most important to spend the most amount of time on. 

As an example, if you have already done remote work, it could be more beneficial to utilize your time to outline solutions you found that addresses some roadblocks or challenges you ran into the last time. 

Whereas if you have never done any remote work before, it could be more beneficial to use your time to outline how you could actually do your tasks remotely.

Suggest a trial period. 

Trial periods will be beneficial to both you and your boss, so it is important that you offer one during your pitch. 

Having a trial period in place will give your boss comfort knowing that they haven’t firmly committed to anything. So they can agree with the understanding that they can say no at the end of the trial period if it just isn’t working for them. 

It will also be beneficial to you to see if you like it, to make sure that your colleagues and supervisors respect your time and workload and if this is just generally something you want to do long term. 

Meeting with your boss doesn't have to be scary or overwhelming if you are properly prepared.

Step #5 – Addressing Objections and Negotiating During The Meeting

Once you have completed your pitch, open up the conversation to answer any questions your boss may have, address objections and potentially even negotiate on the particulars. 

And if your boss says that they need to think through your proposal, politely ask when you can expect a response or if they have any questions you can answer.

What Should You Do If Your Boss Says No?

It may feel a bit deflating if your boss says no to letting you work remotely, but there may still be some potential solutions. 

Try to find a compromise. 

If your boss says no, it can be helpful to have another conversation where you try to find a compromise. 

For example, would your boss be willing to let you work remotely part-time and in the office part-time? Or is there a way to trial the software at the office for a week that you found to help manage your remote work so they can see it in practical application. 

Look to some of the reasons or objections that your boss had that ultimately led to the no, and see if there is any room for compromise there. 

Ask your boss if there is an opportunity to have this conversation again in the future. 

There is a big difference between a flat-out no, and a not right now. There is no harm in asking your boss if there will be an opportunity to have this conversation again in the future. 

If he says no, then at least you know where this conversation stands. 

And if he says yes, you can use the time in between to research more solutions to potential challenges, trial different management, and reporting strategies, and do really good quality work that shows your boss what a valuable member of the team you are. 

And if you really can’t work at the office anymore, then you will need to consider handing in your resignation. 

Unfortunately, life circumstances may be prohibiting you from going to work at the office, and if that is the case for you, then you will need to prepare to hand in your resignation. 

Before you do this though, make sure your boss understands that this would be the outcome, and make sure you do it in a way that doesn’t feel like an ultimatum.

Now that you have the step-by-step plan to convince your boss to let you work remotely, it is time to go and implement this for yourself! 

Read Next:
10 Best Productivity Tips For Working Remotely
Top 5 Companies ALWAYS HIRING Remote Work From Home

What can I do to work from home?


DaLorean began working from home as a stay-at-home mom in 2018 when she wanted to make some side money to contribute to the family income. After building multiple online businesses from scratch, she is dedicated with Happy Work From Home to helping others transition into remote work by sharing remote job leads and side hustle ideas for extra money, teaching how to start an online business, and more.