How to Ask To Work from Home with Confidence

Estimated reading time: 7 mins

Many people work from home or remotely these days. A general thought behind working from home is that it improves your productivity and allows you to give more time to your personal and family life, while at the same time saving you time and money. Commuting to and from your office each day might be taking out too much of your energy and you might be wondering if your boss can be kind enough to let you work from home. However, how do you ask? How can you build your case for securing a schedule of working from home? I am here to tell you just that!

There are reasons why the conventional way of working form an office is losing its relevance in the 21st century. In fact, the 9-to-5, Monday to Friday schedule was a product of the Industrial Revolution. The irony is that while we have moved ahead into a very different era of Digital Revolution, our style of working is still very old school in some ways. According to this article on Forbes, some of the biggest corporations offer the flexibility of working remotely. Having said that, there still is a general perception among employers that working remotely is not as productive. However, this article by the Harvard Business Review suggests otherwise, claiming that working from home helps increase efficiency, engagement and productivity.

Nevertheless, you will need to be in a good relationship with your boss to have the opportunity to discuss working from home. If your employer values and trusts you enough to listen to you, then you can try the following strategies to convince your boss to allow you to work from home.

  • Understand Your Own Motivations. You need to be clear on why you wish to work from home before you present the notion to your boss. It might be that you feel that useless meetings, breakroom chitchats and endless stream of calls are affecting your important tasks and deliverables. Being able to work from home will allow you to keep your focus and get things done without any distractions. On the other hand, working from home might be your preference due to more personal reasons, like taking care of your children and/or ageing parents or joining a fitness routine or starting an academic course on the side. It is important to be honest with yourself and with your boss and tell your employer exactly how it is. This is only fair to your boss who trusts you enough to give you such an opportunity.
  • Create a Plan. Once you know your motivations exactly the way they are, you will need to consider creating a plan of how a realistic schedule of working from home would look like. Are you looking at working from home each day or are you more inclined towards having a mix of both, working in office and remotely? Put yourself in your boss’s shoes and try to figure out how s/he will respond. You could have a couple of plans so that there is some flexibility that you can offer and agree on with your boss. Stress on how you will remain available on emails and phone in case any urgent tasks or meetings pop up. Another tip that I would give here is that if you plan to just work one day from home every week, try to have it be Wednesday, so that your boss does not think that you are trying to elongate your weekends.
  • Focus On Talking To Your Boss. The proposal you present should be short, simple and straightforward. What needs to be more detailed is your discussion that you will have in person. Talk to your boss and show how this can work for both of you. While I do not recommend you bombarding your boss with research numbers and statistics on how working from home is great, it might help to share some credible sources just to build your case. Looking prepared will help you win the case. In addition, do not just focus on how this can benefit the company – it is equally important to show the personal gains that you will get, such as lesser stress and stronger motivation to deliver good work. Your boss understands that working from home is a cost effective way that both parties can benefit from. How they can benefit is what you have to tell.
  • Give Time to Your Boss. The last thing that you would want to do at after presenting your case is be pushy with your boss. It is highly unlikely that your boss will give you the green light right after hearing your side of the story. In fact, it might take him days or even weeks before s/he can allow you to work from home. After your conversation and sharing of the proposal, you will need to back off and give your boss the time s/he needs. It is possible that s/he will need approval from the HR as well as look at the implications such as how this will affect the motivation of other employees. As long as your arguments were good, chances are that you will get at least some agreement.
  • Be Open to Experimentation. An effective way to make your boss accept your proposal is by suggesting a one-month or a couple of month’s trial period to see how it goes. Pilots are always more acceptable to management than fully diving into something new. This way, your boss will have the liberty to roll things back to you coming to workplace every day if things do not work out. If agreed, make sure you present a regular update of all that you have been able to achieve by working from home. Once this trial period ends, be sure to initiate an evaluation meeting with your boss, signaling that the company’s success is the most important thing to you.
  • Initiate Organizational Change. While allowing employees to work from home is fast becoming a standard practice, it is still an idea in its early stages. Therefore, if your proposal is not accepted, you should not take it personally and should understand that there might be greater, organizational hurdles that made it impossible for your boss to allow you to work from home. You might get this response: “I cannot do it for you because then everybody else will ask for it.” Do not be put off by such a rebuttal; try to initiate an organization wide change by discussing the matter directly with the HR. If they can allow working from home in some capacity for everyone (a few days every week/month), this will be a good result for you.
  • Seize the Moment. Okay, so while I am not encouraging you to deliberately do what you want and work from home, you can try to seize opportunities like heavy snowstorm or citywide disruptions like a large convention and do your best work from home. Use this opportunity to demonstrate how your work is even more effective when you get to do it from home. Doing so will help you build your case and try your luck with your boss again.

There you have it – the strategy that you need to follow to convince your boss that allowing you to work from home will be great for you and the organization. To summarize, here are some of the important Dos and Don’ts that you need to remember:


  • Try to be completely honest with yourself and your employer regarding your motivations of why you want to work from home.
  • Present your case with evidence. This will show that you are fully prepared and know the facts.
  • Consider offering a trial period of one to two months, as this will give your boss fewer reasons to reject you from working from home.
  • Take advantage of any opportunity that might come your way to demonstrate how working from home can be the best thing to happen to your organization.


  • Prepare a long, unappealing and difficult to digest presentation. What you need to have in place is a nice conversation, followed up with a short, precise proposal.
  • Be discouraged by a rejection. Engage with a group of colleagues and have a meaningful discussion with your HR department to see how this ca be made possible companywide.

Does your company allow you to work from home? Do you get to work all days from home or is there a schedule that you need to abide by? Let me know in the comments section if you get to work remotely or if you have tried discussing its possibility with your boss. What has the reaction been from your employers? What do you think about the idea of working from home or remotely, without any office, from any part of the world, like freelancers. I also encourage you all to check out our blog posts on Awesome Careers Where You Can Work from Your Home and 5 things your boss doesn’t want to hear you say.



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