If your company has a history of allowing telecommuting, then your conversation will be pretty straightforward. Since there is already a precedent for this practice, you can refer to specific examples or to that particular policy if it exists in writing.
If there isn't a history of telecommuting in your organization, then it's a little less straightforward. But that doesn't have to mean that it's impossible! It just means you will have to put a little more work into making your case.
To actually get your boss to let you work from home, you need to present a detailed plan. You can't just ask, "Can I start working from home?" and expect a positive result. The more prepared you are, the more likely it is that your boss will recognize the importance and feasibility of this option.
First of all, you need to think like your boss. Think of all the reasons he or she might be hesitant to allow telecommuting in your department. One such example is thinking through the implications if your manager lets you work from home two days a week, how does that impact your fellow team members. For every possible objection, come up with a thoughtful response that shows that you care about your boss' concerns.
Be realistic and understand that not every task is something that you will be able to do from home. Track the tasks and responsibilities you have every day, and clearly identify:
If you separate the tasks that you can do remotely versus the ones you have to do on-site, you'll show that you understand the major differences between working at home and in the office.
Give your supervisor actual data so you can back up your claims that you can do your work remotely. A study released in March of 2017 showed data that proved that remote workers are actually more productive than their office-bound counterparts. A couple more resources for statistics:
Generalized data is great and shows that telecommuting is a viable option, but if you can also provide specific data about your organization and your position, that's even better. If you already use a tool to track your time or productivity, make sure to include specific metrics in the plan you present to your boss.
The key to providing data is to establish how you will measure your performance and productivity, because your boss just wants to know that you are doing your work. Give them the exact numbers that will tell them everything they want to know.
Much like identifying the tasks that you'll do, determining your deliverables (and a timeline) is a critical part of establishing expectations. When you, your boss, and your team understand what is expected, there will be less confusion and frustration. Plus, it will give you the structure you need to stay happy when working from home.
Communication, communication, communication. Make sure you let your boss know exactly how you plan to communicate with them and your colleagues. If your team doesn't use them already, then implement some of these communication tools to make sure no one gets left in the dark.
Invest the time in ensuring you have the skills to stay productive while you work from home. Training programs, such as the Workplaceless Remote Work Certification delve into core competencies and practice exercises for working asynchronously and effectively communicating with your team in a remote environment.
Many companies and managers are recognizing that flexible work is here to stay, yet they're still cautious about it working for their office. Offer to work from home on a trial basis, for a preset period of time, a mutually agreed upon number of days per week and establish concrete check-in periods with your boss.
Present all this information in a concrete plan. If you've ever worked remotely before then use that anecdote as an example of your trustworthiness. You can use examples like when you had to stay home due to illness. Or you can refer to a time you called in from a conference.
Remember, think like your boss. If you give them enough evidence to show that you will do your work and that the rest of the team won't suffer, they're more likely to give telecommuting a chance. Good luck!