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How to Negotiate Work-From-Home at Your Current Company (With Email Scripts)

Daniel M. Wolken
Software Developer at DailyRemote
Originally published at ・11 min read

60% of the top 20 companies listed in the annual World's Best Workplaces list have an active remote working policy - Great Place to Work® Annual Reports.

From Salesforce to Hilton to American Express, everybody is embracing remote work as it dramatically expands their talent pool globally. Besides the immediate cost savings from maintaining a larger office space, it also leads to enhanced revenue generated through increased productivity.

Thus, actively implementing work from home policy in their organization is also keeping their employees happy and satisfied, reducing the churn rate, and retaining the best talent. Inclusion of work from home policy is, therefore, a win-win situation for all.

Why should you consider working from home?

A 2-year case study by Stanford professor exhibits just how efficient working from home is. Telecommuting comes with a whole lot of benefits:

  1. You can work from anywhere, which means no need for any office.
  2. No office means no commute. Cutting out a commute is a huge time saver. Plus, a boon to environment.
  3. Taking complete ownership of your work, thus making you more independent.
  4. Working from home leads to fewer sick days.
  5. Working remotely increases focus, resulting in increased productivity.
  6. No commute means you can work longer hours, thus giving better work output as compared to an office day.
  7. No office distraction because you design your own flexible work arrangement.
  8. A flexible schedule means you can start your day early and end early as well. Or, if you're a night owl, flip the clock upside down.
  9. More time with your loved ones, making you lead a happier and satisfied life.

It's clear: remote work is fantastic. The problem is the barrier to entry. Companies that employ remotely often require new hires to have remote work experience. It's a classic chicken
-egg problem. You can't go remote with companies unless you're already working remotely — quite the dilemma.

What you can do instead is start working remotely at your existing company. Asking to go remote is scary and frightening — almost as scary, if not more, as asking for a raise.

If you're struggling to go remote at your current job and asking questions like:

  • How to ask for work from home?
  • How to convince your boss or manager to let you work remotely?
  • How to write an email to ask for work from home, permanently?
  • How to write a sample proposal for asking to work remotely?

We've got you covered. We'll systematically try to answer each question with two bonus email templates. So, dig in.

Analyse your situation according to your job

Asking to transition from office setup to remote work requires a little bit of struggle. So make sure you know what you're getting into, the problems that you'll come across when working remotely, the nuances, and everything else.

Numbers speak. You need to analyze and compare your productivity, focus, and time management skills while working from home against an office setup. It is crucial to understand your productivity, how you juggle your responsibilities, and tasks while working from home.

Whenever you decide to come out to your manager, show them the numbers. Numbers don't lie. If you're able to do everything you're able to accomplish in the office, and more, then there is no reason your manager will stop you.

It would be best if you also got a rough idea of how standard working from home is in your industry or field of expertise. Investigate to find any departments where people are already working in such a setup in your organization. Understand how they negotiated remote working, their remote work setup, and try to utilize it to your benefit.

Don't be trounced back if you are not able to find any department or anyone in your office who is telecommuting. Visit remote job boards like ours, and see if there are remote jobs available in your area of expertise. Be prepared to showcase an excellent case that demonstrates your belief in your abilities and the evidence that people in your industry and job are working from home effectively.

Identify the benefits to your organisation

The art of persuasion starts at someone else's benefit. In this case, it's your company. Your work-from-home setup should be mutually beneficial.

Working from home is going to make your life easier, no doubt, but it should also benefit your employer.

Increased productivity, overhead cost savings, longer work hours, and fewer sick days are some of the highlights you can boast about.

Addressing your manager's concerns and incorporating solutions for those in your flexible work arrangement is a win-win situation for both you and your manager.

Before you start a negotiation on a flexible arrangement for work, be sure to include answers to all the following doubts your manager might have:

  • Does working from home help you do your job better, and how?
  • Will working remotely affect your productivity and project delivery?
  • How will you manage your accountability on daily tasks and performance while working from home?
  • Would you be able to work longer hours with more focus given the distractions at home?

Be flexible and look at it from the company's perspective when negotiating a work from home arrangement.You should be prepared with your answers to all the concerns your employer might have. It will show your employer that you've thought through everything carefully.

Prepare your proposal for work from home arrangement

Outline all the points you have researched about your industry and organization. Then, formulate a well-documented proposal for your remote work arrangement.

Also, consider your timing: If you're a newbie or you're chasing a promotion, now may not be the best time to ask.

Things to keep in mind:

  • Meet your employer to discuss your situation in person, instead of an email.
  • Bring a strategic plan/proposal to the table, with a clear outline of your work schedule and responsibilities.
  • Your work schedule should not be drastically different from your current working hours. It can throw off your employer and can be a potential red-flag. If you're changing time zones, let them know in advance.
  • Be sure to let your manager know in advance about your situation, possibly by an email, discussing your job responsibilities and work setup.

Sample Email to Kickstart Negotiation

Hey [Boss’s Name],

I hope you're having a wonderful day.

I wanted to talk to you about something that is on my mind for the last few weeks. It's regarding my work arrangement and making it so that I am accomplishing my responsibilities and duties more efficiently.

I'm free on [time/date slots] and checked you don't have any meetings during that [date-time slot]. Shall I go ahead and block half an hour of your time?

I am looking forward to discussing this in more detail.

[Your Name]

Ultimately your goal should be to satisfy every doubt your employer has, understanding your remote work arrangement. Assure him that your productivity is going to be similar, if not better, compared to working from the office.

Your remote work plan should address the following topics:

  • Schedule: Sticking to a schedule is essential when you're telecommuting. You need to update your shared calendar, mentioning your availability. Working remotely comes with the added benefit of no commute; thus, you can start working earlier and end early, leaving additional time for your family. You could also suggest a trial period of 1 to 2 days a week to ease into it.
  • Performance analysis: Your manager needs to know that you are completing your daily tasks on time, not just sitting watching TV instead of working at home. It would be best if you gave daily updates via Zoom and send weekly updates via email to your entire team. Moreover, plan your daily and weekly commitments using tools like Trello or Jira in the presence of your manager.
  • Advantages your employer has from your flexible setup: Your work from home arrangement should be beneficial for both you and your company. Draft a proposal in such a way that shows significant positive changes in your work output, that favors the company. Suggest benefits like increased productivity, overhead cost savings, longer work hours, and fewer sick days for the employer.
  • Communication with the team: Use time slots on your calendar. Mark all the slots you won't be available. This increases transparency between you and your colleagues working from the office. Also, share your contact number with the team for any emergency when working remotely. Remote work setup at home:* Make sure you have a productive and practical workspace along with the proper tech and set up to work effectively from home. Be prepared with your flexible arrangement at home, including a laptop and other essentials like an internet connection, a good pair of headphones, etc.
  • Security: Keep in mind the security side of working outside of the office. We suggest the use of VPN's and data encryption software. It would be best if you comply with the security guidelines of your IT department.

Setup a trial run, prove yourself, and build immediate trust

If working from home is not a common scenario in your company, your boss is going to be a little hesitant towards your proposal; he probably won’t approve it right off the bat.

Be flexible when negotiating a work from home arrangement. The more flexibility you suggest, the better your chances of getting a yes.

Suggest a trial run for a month or two. Asking for telecommuting on some particular days in a week like on Tuesdays and Thursdays is also an option.

If you manage to grab a work from home day, consider it an investment and smash it. Perhaps most important, don't just meet deadlines, beat them. Use this trial period to prove yourself, which will ultimately drive you to remote work for a longer duration. The best way to get approval is to demonstrate that you are accessible, productive, and responsive.

Incorporate the following tips in your trial period for telecommuting and make it a success:

  1. Show the power of distraction-free work environment by achieving your deadlines and proving to be more efficient in your daily task.
  2. Be always available and visible(even more than in office). Be responsive by email, message, and phone and have a weekly face to face video chats with your team and manager.
  3. Communicate daily updates of your tasks to your manager, along with your plans, schedules, and career goals.
  4. Establish disciplined work habits to separate your work time from your family time. Use noise-canceling headphones and a concrete schedule to work from home.
  5. Be willing to adjust overtime to make it work for you, your team, and your employer. Be a team player and gain immediate trust.
  6. Be reliable and flexible. If you expect your boss to be flexible with you, reciprocate to meet their needs as well.

Sample Proposal:

Complete this proposal, schedule a face-to-face meeting with your manager to bring up the idea, and then email this proposal as a follow-up.

Hi [Manager's Name],

I hope you're having a good day!

I've been with [Company] for [X years]. I love the culture, the people, and what [Company] stands for.

During this time, I've made many significant contributions like [description of things you did]. Recently, I've also [description of thing you did fairly recently]. Least to say, I take pride in my work, complete it on time & love every minute of it.

I want to take this moment to propose an alternative working style that has worked for me in the past. I believe I am more productive when working from home, and it also gives me a few extra hours each day by cutting down the commute.

I propose telecommuting [twice a week]. I believe I can make it work since my position solely requires a Laptop and Internet. I am more productive working from home, with fewer distractions and breaks throughout the day.

Please consider my request; I am confident we can make it work. To keep me accountable, I can mark my availability on a shared calendar and will report back on the progress with regular check-ins.

Thanks for considering this. I am looking forward to discussing this with you in person.

[Your Name]

Persevere, but don't be hung up

Stay positive and confident, and don't be disheartened if you don't get an immediate yes. Your employer will likely need to consider your proposal and discuss it with his superiors.

But don't be discouraged. Negotiating a work from home arrangement in between of orthodox office setup is difficult. But, change is always hard, be a pioneer, a flexible work arrangement is worth it.

Have patience and do your research, make a compelling case, and don't be afraid to ask — you just might find yourself working from home soon.

You have gathered all resources, even smashed a trial period, but it just not enough for your manager, the organization is stifled on laid out rules and you are turned down, again, and again, maybe it's time to move on.

Remote work is the future. Telecommuting brings several benefits, the reason being a lot of companies are going fully remote. Start looking for a remote job in your industry with the help of various websites like DailyRemote which is a remote job board. You might stumble upon the best opportunity that suits your flexible work arrangement.


How would I know that you are actually working and not watching TV at home?

I have added points in my remote work proposal on how I would do regular check-ins and give daily task updates to the team. We could also plan my work schedule and the communication tools to be used to support my remote work. I will also keep the team posted on my task progress via weekly emails.

What if you are not available when we need you?

My work schedule, as mentioned in my remote work proposal, will outline the hours I will be available on email as well as Slack. I will start and end my day at fixed hours, which will also be updated in the calendar, marking my presence. In case of any emergency, I will always be available on phone during my work hours.

Our company does not have a work from home policy?

I understand that the company does not support work from home. But I can start with a trial period so you can see if this arrangement works before fully committing to it.

Will working remotely not affect your productivity and project delivery, given the distractions at home?

It might seem like my job might be challenging to do from home, but some of the fastest-growing areas of remote work including our industry and many more such as healthcare, technology, marketing, and sales have some of the highest paying remote jobs. I am positive that I can perform everything my job requires and much more at an equal or even higher level outside of the office. I have also mentioned in my proposal, how you can track my productivity and how I will balance my responsibilities. Still, we can do a trial run and see how it works for both of us.

What if everybody also asks to work remotely if I allow you to do so?

If we could work out this flexible arrangement and it is beneficial for both the company and me, you could think of making a work from home policy in the company. If working from home keeps employees happy and productive, you can offer such a flexible arrangement to more people as well.

Negotiating for remote work is still unchartered waters. There will be a lot of things your employer can argue about against remote work. But one thing is going to happen for sure -- either you're going to find a better work/life balance at your current job, or you'll jump the ship.

We hope this guide will help you in masterfully negotiating your way into working remotely.

If you need our help in any shape or form, feel free to reach out on Twitter or Email.

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