• PremoteMe Inc

A Flexible Work Proposal - How to ask your boss to let you work remotely.

Updated: Dec 3, 2019

How to ask your boss for a flexible working arrangement

How to ask your Boss for a Flexible Work Arrangement

Is the standard 9 to 5, Monday to Friday the right working arrangement for you? Do you need more flexible working hours, maybe because the daily commute is draining you? Or maybe you want to spend more time with your family? Is the office just too distracting for you to get your best work done?

Well, all of this and much more is possible if you are working remote or have a flexible work arrangement in place. However, not all managers understand this or are used to this type of arrangement. This doesn’t mean they may not be open to it, but it does mean that you need to ‘pitch them’ on the idea and elaborate why it would be beneficial for the both of you. Packing yourself with all the valuable info in order to have an answer to every question concerning flexible work will dramatically increase your chances of achieving your ideal working style.

Check out our tips on how to ‘pitch your boss’ for a flexible working arrangement:

Why Is Remote Work Better for You?

The first point to relay is, why this option would enable you to be more productive and engaged in than your current working environment.

There are plenty of reasons why remote employees, or employees that work a flexible arrangement are more productive and engaged. From their preferred working environment, to better health and wellness, less distractions, better work-life balance and many others. However, you should know why it would specifically suit you and make you better at your job.

According to PubMed, remote employees are healthier physically and mentally compared to

office employees. A large part of the reason why remote workers are more productive is because remote work is results-oriented, rather than time-oriented or physical presence.

How Does Your Employer Benefit by Letting You Work Remote?

The second point to make is, how will this arrangement be better for your employer.

Again there are many proven and well researched statistics as to why a flexible work strategy is beneficial for employers. From reduction in overhead costs like office space and utilities, to a more productive and engaged workforce and to happier employees who end up producing better work. There are many companies which have implemented flexible arrangements and have experienced a great success.

The long term benefits that the entire organization could enjoy by implementing a more flexible strategy are: accessing global talent, being a more attractive place to work, lower attrition rates etc.

How Do You Plan to Implement Your Flexible Work Arrangement?

Okay, so now they are interested but maybe you are the first one to ask, a pioneer in your organization? And you may have no idea how to go about the transition.

You need to show an ‘action plan’ of how you are going to transition into the arrangement and how you will manage some of the challenges that arise.

Questions to answer may be?

- Do you have the right tools? Laptop, VPN, collaboration tools like Slack, Zoom, Perflo.

- Do you have a suitable working environment? This might include a home office with an ergonomic chair.

- How will you manage communication with your office based colleagues?

How to Make the Ask?

Even after listing all the benefits of flexible work and impressing your boss on how knowledgeable you are on the topic and how equipped you are to get going with the new arrangement, they still may be hesitant or simply stuck in their old ways of management like measuring performance by hours worked or by physically seeing you in the office, and they may be hesitant to give it a go.

Here’s how to convince them that you should at least give it a go and potentially even be the guinea pig in the company. (see how Sacha Connor pioneered a remote transition at Clorox)

1. Present the Business Case and Your “Why”

Delivering your well researched and informative pitch to your boss is your first step when asking for remote work. (see templates here)

2. Ask for Two Days of Remote Work a Week

Chances are asking for a full blown transition may be a bit much at first. It will be a lot easier if you ask for two or three days a week at the beginning to start out and see how it goes for both of you. Chances are higher that this type of request will be approved. This will give your employer a sense that you are still in the office rather than going completely “invisible” by working from home. Later on, you can ask for more remote days, once the employer trusts you and sees that you are not falling behind in your work and especially if you are even more productive.

3. Ask for a Trial Period

Another alternative is to ask for a trial period, sometimes one month is enough (basecamp suggests three months although that may be too extreme initially) just to prove that you are indeed more productive and engaged in your work and you are able to manage the challenges of communication and the disciplines of time management. Once you prove the results, you should have a very strong case in a flexible work arrangement and perhaps you will be the pioneer to change the way your organization looks at flexible work.

If the objection is “how will I know you’re working if you’re not in the office, just suggest using Perflo to set out expectations and measure performance in real-time!


To sum up, flexible and remote work is the future work, however not all companies and managers are prepared or fully open to it yet, so In order for your request to be approved, you should.

Pack yourself with real statistics of why flexible work increases the productivity of employees, and how it can benefit the company as a whole.

Ask your boss to let you work at least two or three days from home to see how it goes.

Make a deal with your boss to start a trial period and if you show amazing results, they will be bound to let you work from home.

So, now that you know it all, why not put everything in practice and see how it goes? You might

be just a step away from working remotely!

Pro Tip: Do an internal survey to see if other employees have done something like this in the past, and ask around to see if any others would be interested in similar arrangements. If there is a collective voice the pitch is a lot stronger than a single voice.

We at PremoteMe are on a mission to empower all employees the resources and opportunity to work remotely within their current jobs, and help organizations make the move.

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