ask your boss to work from home

4 Tips on How to Ask Your Boss to Work From Home

So, you have been considering going to ask your boss to work from home for a while now. Finally, you feel it is time to approach them about working remotely. You know you are more productive when out of the office. You think your work ethic has shown you are trustworthy.

You already take work home on the weekends. But, pump the breaks! Make sure you have a plan in place before approaching your boss. Here are four tips to consider when asking your supervisor to work from home.

Understand your company culture

You can get a sense for your boss’ decision before you step foot in the office. Take a look at the company culture. Are there a lot of remote employees? Does your employer already have a remote work policy in place? If there are remote workers, does management view them positively or negatively? Understand where your company is before you even craft a plan to ask.


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If your company is open to remote work, then things should be a piece of cake. However, for those who are slow to the game, you may have to do a little more digging. See if there is a burgeoning culture that will support a future of working from home.

Talk to HR, see who is already taking advantage of this, and take a look at policies to understand how you may have to approach the situation.

Acknowledge your supervisor’s concerns

Your boss’ two main concerns are likely going to be: communication and productivity. They want to know they can count on you to be available for check-ins, and that your performance will not suffer. I already know what you are likely thinking…shouldn’t they already know that? Yes, they should.

However, supervisors are humans too and have someone else to answer to as well. Make it easy for them by making a point to document your progress and performance metrics. If you are killing it while taking work home on the weekends, acknowledge that!

If you tackled a massive project while the boss was not in the office, include that in your presentation to your boss. Discuss every time you have maintained productivity and communication while not under their eye.

Intelligently discuss the benefits

You and I both know the benefits of remote work. We can recite them at this point like our ABC’s. However, we have to be careful that we are not only discussing how working from home benefits us. Discuss the advantages for the company:

Your level of productivity increases while you are at home.
The hour or so long commute turns into time you can use for work.
You are using less electricity since you are no longer using an office computer or phone.
The extra space you would leave behind could be used for something else.

Take time to research how your change in work style not only helps you however benefits the company. It also doesn’t hurt to have some data in your hands about the benefits of remote work for companies.

Tell them how you plan to work at home

Remove their fears by walking them through what a remote work day would look like. Discuss the exact time you will be available for work. Tell them how you could immediately be reached for questions or virtual meetings, and how that would all work.

Even highlight software and applications that would help you stay in touch to get your work done. Plan out every hour, and show them what it would look like. The goal is to make them understand you are just as successful and accessible working from home. Be as direct and straightforward as possible.

The reality

Now, it would be awesome if this was a slam dunk when you ask your boss to work from home. If you have a forward-thinking boss who is open to change, a plan including these steps has a decent chance of working. However, you do need to come to terms with the reality that even this might not be enough. This is why it is so important to take a look at your company’s culture and attitude toward remote work before going down this road. You may realise your boss nor senior management is comfortable with remote work culture, and you might have to look elsewhere.

This happened in my situation. I worked for a company that was used to having everyone working in one place, and they were uncomfortable with remote work. Working from home was an important principle for me, and I had to seek another employment arrangement.

If this happens, know that it is quite all right. They are allowed to have a different opinion, and you are well within your right to look for a work environment that better fits your lifestyle. However, there are times when requests to work from home are successful.

Success stories

Here are some success stories from others, to help motivate you to ask your boss to work from home.

“You could also ask your boss if you could take some work home over the weekend. If you can show that you were even more productive on a project from home than you were at the office, this can sow the seed for you later when you want to negotiate working from home a couple of days out of the week.

“I did this a few years ago with some success. I was at a point where I was likely going to ask for a raise as I did a great job and had the same salary for a few years. Instead I asked to keep my current pay and work four days a week. It’s not quite remote work, however it allowed me to start working more on my own projects. I could also take on more freelance work, which lead to more remote working.” said Jane.

“I got my first remote job because the firm I was working at the time was splitting in two. Half of the partners and employees left to form their own firm and I was really good friends with the lead partner. They needed help to get their marketing off the ground so I agreed to help them as a freelancer while I continued to work at my current firm.

“I designed their logo, built their website, and designed some initial marketing collateral to help get them started. When my friend discovered that I was leaving the firm, he offered me a job. I told him that I was moving to a different city however that I could help him if he allowed me to work remotely. He agreed, and we worked out a deal where I could work part-time for them remotely. As a result, I could pursue my other passions on the side.

“Had it not been for my good rapport with him as well as the initial project to get them started, I don’t think he would’ve agreed to let me work remotely for him for the next two years. Because I had built trust in my work relationships and was consistently dependable, it set the foundation for me to negotiate a work from home job.” says Andrew.

My advice for those about to ask your boss to work from home, and seeking remote work: be sure that you have built enough “credit” with your co-workers and boss of your work ethic, credibility, and trust. Agree to do a freelance project (remotely) for someone to build some remote job experience into your resume.

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