Starting The Work From Home Conversation With Your Current Employer

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Globally, around 16% of companies are 100% remote, and 44% of companies do not support the idea of WFH (work-from-home) at all. 

If your employer falls into the latter category, then it’s time to shake things up. No, we are not asking you to resign but to speak up. So, if you’re one of those who want to work from home but your pushy boss is not happy with the idea, then build your case and put forward your request. 

We know it isn’t easy to negotiate/persuade, especially with skeptical managers, but remote work has become something of a necessity these days. And if it can help you be more productive and live a more fulfilling professional life, it’s time to have a difficult conversation.

Remember, you aren’t alone in this endeavor. As offices and shops open up again and social distancing restrictions are lifted, more people are deciding that going back to the 9-to-5 life isn’t worth it.

Here is a quick guide with some sure-fire tips to help you start talking about remote working with your employer.

WFH – How To Speak For It 

Talking about work from home is not the easiest conversation to have with an employer, but it’s crucial, especially if you have a solid reason. So, if you have a good job but miss the flexibility of WFH, then follow these three most important tips and make your case stronger:

  • Do Your Homework

When going into any formal negotiation, it’s imperative to be prepared and plan what you want to say and how you will put your case across. 

Sounds complicated? 

No problem, to make your case stronger, here’s how you can go about it.

  • First, learn the remote work landscape in your respective field. For example, is remote working common in your industry?

  • Now, get to know more about your job, organizational structure, and that of competitors.

  • Now, explain how you will accomplish your daily tasks and responsibilities while working from home.

  • Finally, describe your home office setup to your boss; so that they can assess the productivity of the environment.

Get ready with answers to questions regarding productivity and performance. This information will help your boss realize that remote work has become one of the biggest perks an employer can offer, and if they aren’t ready to deal with it, they might lose out on some good talent. 

  • Highlight the Benefits of WFH to your Organization

Before going into the negotiation, list all the benefits of remote work that your employer will attain, including increased productivity, low-absenteeism, limited overheads, especially the labor-related ones, and improved morale. 

To present how you will be more productive while working from home, try to find answers to these questions:

  • How will you do the job better?

  • How will you be focused and able to do the projects more accurately without interruption?

  • How and why will you be more productive?

  • How does skipping your commute help you give more time to work, like start working earlier?

If you’re working in an environment that doesn’t appreciate teleworking, educate your boss about the advantages it has for them. It would be best if you had them on your team. So, be safe; try not to overload your defensive argument with statistics or annoy them.

Create a Plan

 Once you’ve done your research, it’s time to create a formal proposal; no, a casual conversation won’t work if you want your boss to take the arrangement seriously.

Outline exactly why and how the remote work arrangement would work in favor of the company and the employees. Also, please give them a realistic WFH schedule so they know they count on you. Here, to support your argument, you can also recommend some digital tools for communication. 

Ultimately, your goal is to make your boss say yes. Address the pros and cons of remote working from their perspective while managing their expectations, highlighting measurable results, and showing that you’re devoted to the work.

Don’t know what to include in a remote work plan? 

Worry not; we’ve got you covered.

A remote work plan should include:

  • A detailed schedule of the hours you will work remotely and how you will be available – phone, email, or WhatsApp during the specified hours

  • A summary statement that highlights all the benefits, supported with facts and figures

  • List down all the roles and responsibilities you currently perform and how you’ll accomplish them remotely

  • The communication strategy, the channel of communication, your contact number in case of ad-hoc assignments, how will you report your check-ins and check-outs, and how will you be in touch with other employees (via phone, email, or else)

  • The description of your home office – the location, environment, and the arrangement, including the equipment you use

  • An explanation of how will you deal with the privacy and security concerns

If remote working is new territory for your current employer, do suggest a moderate schedule/trial period in your plan.

And for the safe side, plan at least three ways/reasons that telecommuting will make you a better and more productive asset to the company.

Don’t give up or be disheartened if your employer shows hesitancy or reluctance towards your request. Rome wasn’t built in a day.

What If Your WFH Trial Request Got Approved

If your boss has accepted your request for remote working for a trial period, your real challenge begins. Even though you’re a step closer to freedom, you need to win their trust with your performance and output. You will be the maker or breaker of your company’s WFH policies. 

In the end, we would recommend the following best practices to be the best remote employee for your company:

  • Communicate well, don’t make over-commitments

  • Ask questions as needed; it reflects how committed you are

  • Do timely check-in and check-out regularly

  • Provide status updates in time

  • Be visible and actively available to all the audio and video meetings and discussions

If you’ve already experienced negotiating remote work arrangements with your ex-employers, we’d love to hear how it worked out. Good luck with your future negotiations.

Dan McCabe
Dan McCabe

Long time remote worker with the dream of enabling everyone to join the remote workforce. Owner and Editor of

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