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Career Advice

How to Convince Your Boss to Let You Work From Home

Posted by Glassdoor Team

Career Advice Experts

Last Updated September 18, 2017

Whether it was when you were stuck in traffic, waiting for a delayed train, or rounding out your 11th hour at the office, the thought has probably popped up: what if I worked from home?

These days, trends like telecommuting, flextime, and fully remote work are becoming increasingly prevalent. So how do we get our bosses to hop on board?  

To find out more, Glassdoor reached out to Kerry Hannon, career expert and author of Love Your Job: The New Rules for Career Happiness. 

Hannon says that the research for Love Your Job, as well as interviews with hundreds of workers, has shown a simple truth: “that more flexibility in scheduling day-to-day activities leads to greater happiness on the job.” 

With Hannon’s insights, we’ve drawn up a 7-step plan to convince your boss that it’s time for them to join the trend and let you, too, work from home. 

Do some “market research”

Have employees from your company worked from home in the past? Did they work partially or fully remotely? What kind of jobs are the most suitable for remote work? These things are crucial to find out before you start mapping out your strategy. If no one from your company has ever worked remotely, you might have a more difficult sell to your boss than if it’s a common occurrence. 

In addition, your colleagues are an invaluable resource in your preliminary research. Hannon suggests asking people how you work with who have the option to work from home about how they’re faring with it. “What are the challenges? The rewards? How did they ask the boss if they could work from home either full-time or part-time?” Hannon suggests asking. 

Plan the conversation

Now that you have some information under your belt, it’s time to plan your strategy. How can you present this information in the most compelling way possible? 

That’s why step two, planning the conversation, is arguably the most important step in the whole process. The better you can plan, the more sympathetic your boss is likely to be. According to Hannon, failure to plan ahead is one of the biggest mistakes that employees looking to ask their boss for remote work make. “From my experience, people don’t take the time to do the soul-searching and strategizing they ought to before the big meeting with the boss,” Hannon says. 

Hannon advises developing a well-defined proposal beforehand that gets into every nitty-gritty detail of how you’ll telecommute, including the number of hours you’ll work from time, when you’ll be in the office to work or attend meetings, and how you’ll factor in unexpected overtime. 

“You must be able to articulate how having the flexibility to work from home will make you more efficient. It will eliminate a long commute, for instance. Increased productivity is a top reason employers are willing to let employees work remotely,” says Hannon. 

[gd-related link="/blog/8-best-practices-for-successful-remote-workers/" label="8 Best Practices for Successful Remote Workers"]

Pick the right time

It’s hard to know in advance when your boss will be having a good or bad day (and therefore be more or less receptive to your ask). But there are definitive clues to when it’s a good time to have the “work from home conversation,” and when it isn’t – it just takes a bit of poking around to find out what these clues are. “Is your department facing cutbacks? Is his or her boss putting pressure on for better results, or is there a big project facing a deadline. If so, you might need to pump the breaks and wait until things are less stressful,” Hannon advises. 

Have the first word

When you’ve done your research, made your strategy and found the right time to talk about it, it’s time for you to make the big ask. At this point, remember it’s important to not just put your request in terms of how you will benefit you (I’ll be less stressed, I can spend less time commuting, I can spend more time with family), although these are all important to bring up. It’s also crucial to talk about how these will benefit your boss and your company (you’ll have a more productive worker, there will be more time for me to work on nights and weekends for you, and so on). 

When we asked Hannon what the very first line in this important conversation should be, she suggested starting with: “I’d like to explore the opportunity to work from home and how you and the department can benefit.”  

[gd-related link="/blog/how-to-manage-a-remote-manager/" label="How To Successfully Manage A Remote Manager"]

Take baby steps

Having an employee ask if they can work from home may be foreign territory for your boss. They may have fears that you’ll slack off, be less reachable, or less able to collaborate with your team when you’re working outside of the office. It’s your job to be able to quell these fears. 

For this reason, Hannon suggests starting with baby steps. Rather than asking if you can immediately transition to fully remote work, take it one ask at a time. This could be through a three- to six-month trial period, or through a transition to 1 or 2 days per week where you’re working from home. After this trial period, you can go back and evaluate how working from how is going for the two of you.  

Give constant feedback

“During that pilot period, communication will be the key to your success, so you need to stay connected and open about any obstacles on either your part, or from your boss’s perspective, that need to be dealt with immediately,” says Hannon. 

The trial period is a critical time to show your boss that you’re up to the task of working from home – and that as you previously told him or her, that it will make you more productive. 

[gd-related link="/blog/how-to-give-more-powerful-positive-feedback/" label="10 Examples of How to Give More Powerful Positive Feedback"]

Be patient

There may be a long time gap between when you make the first ask to your boss, and you fully transition into the work from home schedule that you were hoping for. Many compromises and tweaks may need to be made along the way. So take things one step at a time, be prepared, and hope for the best. 

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