How to Convince Your Boss to Let You Work Remotely

In Working Remotely by Phoebe Nicolas

Times are changing and we are living in an era where work dynamics has also changed. People would think working from home is all smiles and easy breezy but it requires discipline to start work and go the extra mile to prove your boss you are not slacking off. In fact, it’s not for everyone because only determined workers would be able to pull off working remotely.

The key to convince your boss to let you work remotely is to prove that you’ll be as efficient as you are in the office. By doing so, you are assuring him you are not just slacking off and you are actually being more productive working remotely.

Companies big and small are providing opportunities for their constituents to work from home. There are a lot of factors behind this work paradigm shift, such as increased productivity among others. As you are contemplating on the possibility of working remotely, let us walk you through some things you need to know on working remotely. Throughout this article, we will approach working remotely in 3 A’s: Assess, Approach, and Assure.

Do you have what it takes to work remotely?
Why do you want to work remotely?
Will working remotely be feasible for you?
How to approach your boss
How to work remotely successfully


Do you have what it takes to work remotely?

There’s a higher chance your boss will let you work remotely once it is decided that you a trusted and reliable employee. Not only that, there will be many other traits one must possess to be able to successfully work remotely. It has to be established that you are a competent worker and an asset to the company. Below are some of them:


  • Without a supervisor or your boss preying on you in the office, you have to rely on your self-motivation to get started working.
  • Initiative is a vital component to working remotely, and if you can’t start working until somebody nags you to, you might want to reconsider your choice.


  • You have to prove to your boss whether you are in your pajamas or in a corporate suit, you’d be equally efficient – if not more.
  • A reliable worker should complete tasks with little to no supervision needed. You must be able to produce quality output at all times.


  • Working remotely means you’re left to fend for your own – meaning no assistants to remind you of the things to be done. Remembering your tasks for the day can be overwhelming, and if you don’t organize your thoughts and work, you might miss out on executing some important matters.


  • Whether you’re working remotely from the beach or from your own bedroom makes you think you’ve got a hold of your time. However, oftentimes you can quickly get carried away without noticing the day is about to end and you haven’t accomplished a single thing. A worker who knows how to prioritise and practices time management well shows a good example of being able to work remotely from home.

Good relationship with boss/es

  • Before attempting to propose to work remotely, see to it that you have formed a good relationship with your boss. Don’t attempt proposing to work from home if you’ve just gone head to head with your boss, chances are he won’t grant or even consider your request.
  • Make sure that you’ve been in good standing with them (but not sucking up). See to it that you both have a good personal and professional relationship with each other.
  • Preceding your proposal to work remotely, build up good rapport and establish trust – 2 key things that will gain you that approval.

Why do you want to work remotely?

Ask yourself this question: “Why do I want to work from home?”. The answer can vary from person to person but it is important to be clear with your intentions of preferring to work remotely so that your boss will understand and consider letting you work remotely. Working remotely has its advantages such as: more time for other things, less commute, less distractions, travel opportunities and work-life balance.

Unconducive working environment

Some workers love the buzzing of people around the office while some dread it. A crowded and noisy office can easily distract some people and pull them out of their work vibe. This results to decreased productivity and a negative attitude towards the work-space. With a more conducive working environment (sans gossiping co-workers and noisy background), one can focus on work better.

Incessant Distractions

We all have that co-worker who loves to go around each person’s desk for a quick chit-chat. There will be numerous telephones simultaneously ringing around the office and you can’t just get them out of your head, making it difficult to complete tasks. Working remotely, on the other hand, allows you to continue working with less distractions. This way, you won’t be easily disrupted.

Commuting and Traffic

Whether you go by public vehicle or drive your own car, commuting can easily suck up your energy early in the morning, especially when it’s partnered with heavy traffic. Working remotely cuts you the hassle of commuting and saves precious time which can instead be spent with family or other important matters. It is said that people who work remotely put in more hours working – the exact hours they save from the daily commute to and back from work.

You Have A Child

Raising a child is difficult to balance with a career with all the preparations needed for a child’s day. It is made more difficult without a reliable nanny or guardian. Some workers may choose to work remotely because of the time freedom it gives them, balancing the time between work and caring for the child. Explain to your boss the cost of child care services and carpooling, he might share your sentiments and consider letting you work remotely for the mean time.

Chronic Health Issues

Chronic health issues such as allergies and asthma can greatly disrupt work and can promote absenteeism. Whether you’re an asthmatic with constant need for nebulization or some other form of chronic illness, working remotely may be a good alternative to working in the office. This reduces calling in sick days and unforeseen absences.

Will working remotely be feasible for you?

Although the thought of working in your pajamas at the comfort of your own home sounds very enticing, working remotely is not for everyone. Bosses might not consider if you simply want to work from home to wear pajamas all day or because you want to spend time with your boyfriend. There are several things one must determine before proposing to work remotely. Before attempting to propose working remotely, reassess your situation.

What is the nature of your job?

Working remotely works well for a lot of industries, but not all types of jobs will let you work remotely, especially if your job requires constant face-to-face interaction with clients. It is important to determine whether or not your job can be done and completed remotely on your personal computer instead of your desktop in the office. Work that is done mostly over the phone or via email lets you work remotely without a hitch.

Fields such as creative design, information technology, customer service and copywriting require less personal interaction than other jobs and these are the kinds of jobs that will let you work remotely with ease. These jobs can easily be done in the comforts of your home with just a reliable personal computer or laptop.

Determine your workload

How vital is your position to the company? How much do you have on your plate daily and how long does it take you to finish your tasks? If most of your daily activities are spent on the phone and facing a computer through email and chat, there is a good probability you can work remotely. If you are a manager of a team, it is imperative to overlook your constituents’ tasks regularly. Fully working remotely may prove to be difficult, but working remotely some days of the week can work.


How to approach your boss?

Now you have finished assessing yourself and still think you want and can work remotely, it’s time to face probably the biggest hurdle yet – your boss. After all, it is his decision to make whether or not he will let you work remotely. Your boss may be skeptical about your intentions of working remotely, or if you’ll actually accomplish something while working remotely. With the steps outlined below, the aim is to help them understand and become less suspicious of your intentions.

Do your research

  • Think of this proposition to work remotely as a business proposal. You should be able to sell and deliver your proposition to your client, aka the boss. Although much less informal than an actual business proposal, it is important to research on your proposition prior to talking to your boss.
  • For bosses who are new to the concept of working remotely, convincing him would be a lot easier if you have the data to support it. Researching everything about the topic may help you become more confident to explain to him how it works.
  • If you talk to your boss about it, the best armor would be strong arguments backed by actual statistics, personal testaments and facts about working remotely. There is a good amount of data on working remotely available to support your statements.

Avoid emailing your request!

  • You’re still proposing to your boss to let you work remotely, so don’t start emailing him things you could tell better in person. Your boss would probably appreciate it if you asked in person rather than through email or text.
  • If you e-mail him a haphazardly written one, he might take it in the wrong direction or misunderstand your statements, jeopardizing the possibility of being allowed to work remotely.

Prepare a written proposal

  • Again, bosses would appreciate more if you’d ask face-to-face, where intentions can be made clear real time. Put into writing your assessment of yourself and the workload, as you’ve read in the earlier part of this article. Clearly state why you want to work from home or wherever, and what qualities you possess that makes you fit to work remotely.
  • The proposal does not need to be lengthy; make your proposal brief and concise. You are creating something to spark your boss’s interest, not to bore him with a 10 page discussion of your proposal. Ideally one or two pages explaining everything should do the trick.

Focus on benefits to the company

While working remotely seems to be at your advantage, your boss could care less about your long commute, chronic illness or noisy workspace. This is why, when you make your proposal, write down what your boss wants to hear. What’s in it for the company? The company’s goal is to make profit, and not pamper it’s workers. Enumerate the different advantages of letting you or other work remotely.

You can start by producing quality output, pitching in more ideas beneficial to the company or accepting a new project. Other than that, stress how the company can save by letting you work remotely, by saving on space and other necessities.

They need to be reminded that working remotely will become an asset on their part and not a liability. Here are some of the benefits you should raise to them:

  • Save money – Working remotely raises worker productivity with the ability to increase the company’s revenue.
  • Improve worker performance – Working remotely allows workers to be comfortable, pressing out creative ideas they can pitch in to the company. It also improves worker turnover as well as the quality of work they produce.
  • Reduce absences – Prohibiting workers to work remotely can promote absenteeism. They may feign sickness just to call in sick and be absent the whole day.
  • Promote environmentalism – If your company is environmentally conscious, then they would love to hear how letting you work remotely reduces their carbon footprint by reducing commutes.

Anticipate questions

Now that you’ve memorized your speech over a couple of times, try to foresee any questions your boss might ask you. As you write your proposal, you should anticipate any concerns your boss may raise. It leaves good impression knowing you’re prepared to answer the questions down to detail.

Your boss will have a lot of questions such as what hours do you plan to work, how you plan on accomplishing tasks, how will he make sure you are working, and how do you plan on updating your superiors. Be prepared to answer all of these.

Offer a trial period

No boss in their right mind would agree to letting you work full time remotely right away. You have to give it in small pieces so that he won’t be overwhelmed. If your boss is all-new to this working remotely routine, you might want to offer a trial period. It can be working remotely once a week, then can escalate to a week, and to a month if everything goes well.

A trial period is a good way for your boss to test the waters and see he’s alright with this set up as well as a good test if you truly can work productively remotely. It is also a good way if working remotely is as you expected it to be and that you would be comfortable in the remote workspace.


How to work remotely successfully

After your boss has listened to that well-researched and well-prepared speech, he might be considering to let you work remotely. Do not push too far and give him the space and time to think about the implications of letting you work remotely.

With that in mind, reassure your boss that you will remain professional working remotely just as you would be if you were back in the office. He still has hesitations, and it is your responsibility to pacify his thoughts. Here are some things to put in mind to gain your boss’s complete trust.

Establish a definite communication

One thing bosses love about the office is the ease of communication – he can buzz you in, call you over the landline, or simply approach you on your desk. These will be a different when he allows you to work remotely. Communication does not need to be jeopardized just because you are working remotely, instead, it should be reinforced and even made more available.

Ask your boss how he prefers to communicate while you’re working remotely, be it via email, text, or phone calls. Other than that, offer him applications that can let him monitor your work real time or view your presentations. Some of these applications include Zoom, an online meeting application where you can share your screen or presentations real-time.

Establish a definite schedule

Even if you’re working remotely, your boss would appreciate if you have a work schedule and not just working randomly in snippets of hours at a time.

  • Set specific work hours to make sure you are getting work done. Have your boss approve the days you will be working and what hours you will be available.
  • Details such as where will you be working from (whether from your home, a coffee shop, or a vacation place) should be made known to your boss so he can anticipate what to expect when he suddenly calls you up.
  • On top of this, highlight your time flexibility and that you will be available as the need emerges.

For the first few days of working remotely, you might be unsure of how you will go about your day. It is important to establish a definite action plan for your tasks so as not to waste precious time. Likewise, we have reiterated that not all tasks are meant to be done remotely. Determine which tasks can be done remotely and which ones cannot be. Breaking down your daily tasks and commitments and plot them against a schedule.

Start out slow until you establish a definite work routine remotely. Following a schedule will keep your head above all your tasks as well as regularly remind you of the things that need to be done.

Get things done

Track your progress daily and report it to your boss. He will appreciate the gesture as well as give him peace of mind that he’s making the right decision to allow you to work remotely. You need to see to it that he knows what you’re up to during the specified work hours.

Applications such as Trello and Asana allow tasks to be assigned to you and you can rearrange or tick them as you finish each one. There are also several applications for tracking work, such as Time Doctor and Time Hub. These will be for your boss’s own usage so he can view and monitor the hours you are working. Always remember to prioritise work.

Be prompt

Now that your boss has agreed to let you work remotely, always respond promptly to messages, calls and emails. As said earlier, communication is vital and should be reinforced. Return calls if you missed them, answer e-mails as you receive them and reply to messages quickly. You don’t want images of you being unproductive to cross his mind. Assure your boss that you will be within reach no matter the circumstance and no matter how small or big the concern is.

Be consistent

Just because you’ve impressed your boss for the first few days means you have an excuse to slack off. He can always call you back to the office when he deems that you are not as productive as when you started off. Consistency is key if you want to keep working remotely.

You can also use the assessments in this book to understand how to craft a remote work plan that not only fits your temperament and work duties but puts your boss and company at ease by showing them how THEY will benefit from allowing you the flexibility to live a balanced and productive lifestyle.

In summary, working remotely isn’t just a walk in the park. It is something that needs motivation, discipline and organization, and only a motivated, disciplined and organized worker will be able to keep up with the demands of working remotely. The best way to convince your boss to let your work remotely is to state clearly the beneficial impact of working remotely and detailed plan of how you intend to accomplish tasks and projects remotely, so good luck!

Phoebe Nicolas
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