How Do I Ask my Boss to Work from Home?

Step 1) Do your research

For starters, you’ll need to research your company and find out if there is a precedent of employees working from home. Feel free to approach your HR department for details on your company’s remote work policy.

Of course, even with all the information you gathered, you’ll need to make a strong proposal to your manager. To support your case, you can also gather the statistics that show how remote working is good for the employees and company alike. 

Step 2) Negotiate and find the middle ground

Making a plan for how to ask your boss to work from home isn’t just about presenting the facts and figures behind your choice. You’ll also need to be ready to compromise. 

Your boss may insist on a short trial run to assess your productivity levels. They may even ask that you limit your remote work to just a couple of days a week instead of a fully-remote schedule. 

The key is to let your boss know where you’re coming from and then understand their perspective as well. You may even end up compromising and agreeing that a hybrid work model is the best solution for everyone. 

Step 3) Reassure them about any logistical issues

Remote working may help you reduce costs, spend more time with your family, and better manage work stress. Still, you need to reassure your manager about any logistical concerns they may have about a potential transition to remote work.  

If you want your boss to seriously consider your request to work remotely, figuring out logistical details is a good place to start.

Consider the following: 

• Can all your current projects be handled remotely? 
• Will off-site processing and storage of certain data present privacy roadblocks and even compliance issues? 
• Will a VPN be necessary in order to access internal documents and information? 
• Will you require extra equipment to do your work from home? 
• Can your team migrate their tasks to a work management platform that will enable asynchronous communication and visibility? 

When considering how to ask your boss to work from home, consider all the implications of your request.

Step 4) Understand when to ask about remote work

Now that we’ve tackled the question of how to ask your boss to work from home, it’s time to address the question of when to ask about remote work. Unfortunately, it’s not as straightforward as making a plan to ask your boss when you know they’ll be in a good mood.

Instead, you’ll need to acknowledge the context of your team or department in order to make a good decision about when to ask about remote work. 

For example, if you’re in the middle of a product sprint for a crucial release, you may find it hard to justify a sudden shift to remote working. Additionally, if you’re a new hire with an unproven track record, your boss may want to get a further sense of your skills before allowing you to transition away from an in-person office.

If you’ve settled into your current position and feel your workload is manageable while in a transition phase, you may feel that you’re in a good position to ask your boss if you can work from home. 

The question of how to ask your boss to work from home is unique to your individual situation. However, your approach should consist of research, planning, compromise, and timing. Be sure to clarify which resources and tools you'll need to make your transition as easy as possible.