How to Ask Your Boss to Work from Home


More and more companies are adopting a flexible approach to how work in the organization gets done. Flex-time schedules and work from home arrangements are now common as online collaboration becomes more feasible for everyone. Many successful companies are cultivating employee-centered cultures that allow the employee to choose the best way he or she can contribute.

But not every company has a culture that openly embraces the modern age of working from anywhere you have an internet connection. Likewise, not every manager is likely to share the same level of comfort with this type of set up, even in more progressive company cultures. There are many out there who still feel like the face-to-face interaction in the office is critical to productivity even for those whose work is 90% comprised of work on a computer.

When you plan on making a request to work from home, it all starts with strategy and planning. Your approach should be tailored to your company culture and your manager’s preferences. Needless to say, here are a few things that, despite your individual situation, may be helpful incorporate into your plan for seeking approval from your boss.

Evaluate your role. Not all roles are suited toward working remotely. Some require face-to-face interaction and a lot of impromptu meetings. Evaluate how working remotely might impact your effectiveness. Think about those you typically interact with the most and evaluate how effectively they use communication tools such as email, instant messaging, shared directories, and even phone calls. Also think about reasons why working from home might be more effective for you. Maybe you could avoid distractions such as workplace chatter, loud phone conversations, or even excessive foot traffic in your work area.

Evaluate the culture. Remember there may be stigma due to how others have treated the privilege in the past. Try and understand the cultural expectation and adjust your expectations. Ask around and see if anyone has examples of current or past situations where working from home was allowed. If there is a policy in the company that covers working remotely, become familiar with it. It’s likely that the company’s HR policy will defer to manager discretion, so learning about past situations will be important regardless. Understand has worked and what hasn’t. If there is any kind of stigma due to past situations, you have a higher level of scrutiny applied – but remember you also define the obstacles you have to overcome.

Develop a good reputation. Build the understanding with others that you work hard and focus on the completion of tasks, not on the clock. This is important because focusing on getting the job done even if it means staying late sometimes demonstrates responsibility. Show you value being part of the team and achieving results more than leaving 30 minutes early on Friday. Building a reputation that you can be responsible to do what you say you will and get things done builds trust. Being a valuable team player will also increase the likelihood that your employer will accommodate your requests.

Be patient. It takes time to develop the level of comfort with people necessary to allow them to work without direct, physical supervision. This is especially true if you are a new employee. Be patient and understand that the organization might not move at your pace when it comes to embracing new ideas and cultural change. Remember that just because your boss or the company might need a little time to feel comfortable with the arrangement doesn’t mean they are rejecting the idea.

Recognize working from home is a privilege not a right. Even if you think your boss is progressive and will support the idea, nobody likes those who operate with a sense of entitlement. You are not entitled to working from home so recognize that it is a privilege. Even when there is an HR policy in place, unless it is in your job description that you are based in a different location – and even still in those cases – you are not guaranteed the opportunity as a condition of employment.

Ask, don’t tell. Make sure you bring up the issue as a request not a demand. This means be mindful of both the time and style of your delivery. Even though these details shouldn’t impact a manager’s ultimate perspective, they are likely to impact their reaction to your request. Try and maintain a respectful attitude regardless of the outcome. It doesn’t help your long-term objective to argue. Resistance at first does not mean permanent rejection. Try and stay flexible and be positive about how any outcome can benefit your contribution to the team.

Start incrementally. Take advantage of any small opportunity to work from home and prove your effectiveness. Give extra effort to ensure that you make the time even more effective that it would be at work. Highlight your achievements for the day so those at the office take note. Don’t run errands, do chores, or watch TV when you are working from home. Be online on time. If you can exceed expectations on small opportunities like this, you are likely to be given more freedom and responsibility later.

Ultimately, if you are a key player and responsible individual, you prove that to your manager and company, and your effectiveness is not inhibited by working remotely, then your request should get granted. Even inflexible employers should strive to retain key personnel and keep them motivated. Be patient and stay positive. Understand that not everything moves as fast as you want it and remember that getting things done for your employer is more important than the convenience of no commute. Remember that resistance is not rejection and try and constructively break through the obstacles as you identify them.