How to ask your boss to work remotely

January 4, 2022

Over the past year, you've realised that you can do the same amount of work (if not more) without having to be in the office. Now it's a new year, and you want to ask your boss to work remotely full-time, even if your boss is going to be asking you to return to the office.

Over the past year, you've realised that you can do the same amount of work (if not more) without having to be in the office. Now it's a new year, and you want to ask your boss to work remotely full-time, even if your boss is going to be asking you to return to the office.

Your options are: 1) Comply and Return, 2) Quit and read how to get a job working remotely, 3) Be a leader, Invest in yourself, and talk to your boss.

In this post we are defining a framework so you can address point #3, which is having a conversation with your boss about working remotely. Or as we prefer saying: Make your boss convince you to work from home.

If your organization is new to remote work, you will have to do a bit of the leg-work, be ambitious, take initiative and ownership of this project you're embarking on. In the end, everyone will benefit from your work whether it is fruitful or not. Leadership doesn't come with the title.

Preparing for the Full-Time Remote Work Conversation

For the leaders who have yet to grasp the value of remote work, their rigidity is a result of a misunderstanding. This misunderstanding causes fear, and that fear is what causes aversion to remote work.

Your first job is to do your research, and try and understand what are the fears your boss may have. By understanding their fears and concerns, you will be able to put forward a plan which pro-actively addresses their fears. Unfortunately it's hard to figure out where to start when "doing research".

Here is a simple framework to help your boss grasp what remote work means to you, how valuable it is to the company, and how it'll make her more successful.

We'll provide you with a template to start verbalizing your personal motivations, establish common objections to remote working, some prepared solutions, and provide you with a document which you can fill up to help you initiate a conversation with your manager.

Personal Preparation

Why do I want to work remotely?

What are the real reasons you want to work remotely? Is it to cut down on commute? Is it to reduce noise? Spend more time with your family? Because you prefer it? You don't have to feel bad for your reasons, but you have to know the reasons.

What is my decision boundary?

What if I put together a plan, and go to my boss and she refuses to listen to me, or simply refuses to let me work from home? What's my recourse? Is that acceptable to me? If it isn't, what are my personal next steps?

The reason we express this as part of our framework is because sometimes your boss might just say no. You will have to listen, figure out what the real objections are, and work to address those. The other option is to leave, there are plenty of places who will be happy to offer you remote work.

Remote Employee Highlights

Over the past year, you are likely to have been working remotely and that is perhaps your motivation for wanting to continue to do so. Figure out what have been some of your highlights.

  • Outline some projects which you have successfully brought to completion.
  • Put forward collaboration with other teams and other departments
  • Express how you've adapted your communication methods to be more effective
  • Describe how you have increased transparency and adapted to a new working style.

These 4 bullet-points serve a very specific purpose. Project Completion, Collaboration, Communication and Transparency.

Remote Work Failures, and Recoveries

In the spirit of transparency, it is also important to bring forward some of the harder lessons you've had this year. What are some of the projects that failed, what are some issues that fell through the cracks, etc. If you've messed up, take ownership of it.

Your goal here, is to show awareness, but more importantly how you addressed, adapted and modified your working environment to prevent such failures in the future.

Bringing those issues AND SOLUTIONS forward shows honesty, transparency, accountability and personal growth.

External Positive Feedback

Talk to other teams and people you have collaborated with over the year and gather their experience working with you remotely. This provides your boss with an external perspective.

You can ask colleagues, executives and even customers: "In an attempt to continuously improve, how has it been working together, in a remote manner, the last year?"

This puts an ask in front of your audience, and provides a "why" you are asking. You are asking for help on how to improve. Regardless of whether your boss agrees to your request, this will be valuable to you.

Conversation Preparation

Before we start figuring out how to prepare for the conversation, listing common objections, and what makes your boss successful, sit back and think about the last positive interactions you've had with her. What made those remote interactions effective? Whatever the reason is, your #1 job is to make this interaction positive.

Common Objections to Working Remotely

There are common objections which always come up when discussing with a certain type of manager. They often come down to a version of micro-management, and always revolve around fears. Here are a few objections, with their causes and potential solutions.

Difficulty to train teams

Cause: Many managers take a strange stance of having to "see" people in order to believe they are working. If you've ever worked in a more traditional office setting, you may already be aware of the "training days" in the office. Multiple managers like to "see" their teams taking notes and discussing. The act of seeing (read transparency) provides them with comfort. Working remotely can seem opaque, and for them removes that ability to "see you".

Solution: Single-day training programmes do not need to disappear altogether, however your job is to figure out which tools can help you provide more transparency into your remote work and your communication. More often than not, we've noticed it's the employees who end up benefiting from more transparency and accountability. Come up a list of products and communication processes to "let your manager see". This may appease their discomfort.

Products: Here are a few products and techniques to improve communication and transparency:

  • Trello: A very basic and simple-to-use tool to help you track progress of tasks. Can be used during training.
  • Slack: A tool for asynchronous communication. Make sure to read how to unplug from work
  • MedAll: MedAll is an example of Healthcare Training for live or hybrid-events.

Remote workers are lazy and hard to evaluate

Cause: A common myth is that people working from home are wearing pyjamas and watching Netflix all day. Whilst wearing pyjamas and having Netflix as background noise will not negatively affect your output, remote worker often remains pejoratively portrayed as lazy, and unproductive. This is partly due to traditional and outdated performance metrics such as time-in-seat, first-in-last-out of the office, hours in meetings, commits per week, projects completed per week, etc.

Solution: You might not be the boss (yet) but it's important that you provide a fresh perspective to performance measurement.

  • Start by establishing clear personal and team-wide objectives. These objectives should be clear, simple and target the business' high-level goals.
  • Measure outcomes, not arbitrary performative indicators, by establishing and developing an "outcome statement". This means figuring out "what" will change and its business impact, by how much it will change (indicator of success or not), and when (roughly).
  • Further more, bring forward the concept of using The OKR Management Process.

Products: Here are a few products and techniques to change how you measure performance:

Hard to communicate

Cause: There is great value in cross-pollination across teams and not being in the office can sometimes have the negative effect of not being able to over-hear solution to that tangentially related problems you're working on. That's why many bosses are averse to people working from home because they believe they will lose that value. Often they fail to see that chatter is more distracting than anything else.  

Solution: With the right tool, working remotely can have both the benefit of improving focus, as well as being able to "overhear" and utilize your colleague's conversation capital. This is partly what Clearword addresses by allowing people to catch-up on any discussion you had previously not been made purview of. New communication technologies allow for a wider breath of inclusion for hybrid and remote workers.

Products: Some products to help with communication were mentioned above (i.e. Slack, Trello), but here are some more:

Can’t build company culture

Cause: Many companies still seem to operate under the belief that culture can only be built when people are together. Whilst there is incredible value to seeing and meeting each other, many other values can be built upon and they don't require being in the office everyday. Fostering a culture of inclusivity, diversity, honesty, accountability and transparency can all be achieved without actually ever meeting anyone. Managers who believe the only way to build culture is by physically forcing people together, are failing to understand that great culture starts with trust, not with only with games and fun. Trust is fostered over-time.

Solution: The solution is to look at your company's values, and try and understand what the culture actually is. This is a case where you will need to ask and actively listen. If the rejection of your request is justified by an inability to maintain culture, ask your boss to explain the culture and its foundations. You have to really listen, and try and understand how you can continuously improve and contribute to that culture. Think of situations in the past, where someone was working remotely and the company culture was fostered. Feedback from other teams (Which you have compiled) will also help express how you are continuing and wanting to nourish the culture.

I don't like it

Cause: Cherish this moment. This is a boss who is transparent and clear. It's an incredible growth opportunity for both of you. You are lucky enough to have a boss who displays vulnerability. Discomfort stems from a lack of trust in this case, and for most managers is the hardest part to overcome.

Frankly most objections stated above really end up here at "I'm uncomfortable" or "I don't like it" because they haven't been given the tools and confidence to manage remotely.

Solution: You now have to do their job for them. You'll have to listen, and figure out what it is they dislike. From there, you will realise it's all about communication and trust. Your job now is to propose tools to collaborate more, and give that person even more visibility than before. Through visibility you will build accountability, and this trust will start going both ways. We always say leadership doesn't come with a title, this is your chance to put it to the test. The only person who will make your work-life-balance better is you. Investing in your relationships at work, and establishing boundaries, meeting cadences, meeting hygiene, etc. will make you better.

Products: Here are some products from collaboration to project management to help communication more clearly.

  • Slack as mentioned above allows for a more natural asynchronous and natural communication style
  • Coda and Notion as mentioned above allow for teams to write more documentation, be more verbose in what they are doing from a remote position. Ultimately this isn't a waste of time it's an investment if the company's people and their knowledge.
  • An article on how to embrace transparency in team communication
  • Microsoft Teams, Google Workspaces, both solid workspace collaboration tools to share files, documents, calendars, and give more visibility across your teams.

Understanding Your Boss Better

When building product, we have to pay special attention to what we are building, for who, and why we're building it for them. Intercom published a useful article on the concept of Job Stories and how they can help us build more useful features by understanding our customers better.

Whilst this isn't an article about product development, we are going to be building something similar, let's call it: "The Boss Story".

Our goal is simple, to understand the boss better, and what motivates her. Spoiler: This is something you can use for a lot more than just asking to work remotely.

Not unlike the Intercom guide let's use the "When, What, Why" structure. Going over previous discussions with your boss, or simply thinking about conversations in the past, you may have become aware of topics that motivate her. You might remember a task she asked you a little too often about. Those are all scenarios you can put in this very simple Boss Story framework.

The structure is simple: When ___, she wants to __, because she _____

  • When she's asking me to come in the office, she wants to see me, because she doesn't have visibility into what I'm doing.
  • When she's sending me three emails, she wants to make sure I understand the task at hand, because we do not have a centralised system in place for me to provide updates
  • When she's letting me to work from home two days a week, she wants to benefit from my energy in the office, because some other people lack that energy and she believes I am positively contagious.

With this little framework, you will start empathising and understanding your boss a little bit more, but the gaps will also appear. In those three examples, there is clearly a lack of communication and leadership visible.

Try it

In either case, to build trust you should suggest a trial to see how things go. Not unlike the rest of this article, don't forget to establish expected outcomes, and how you are going to measure whether the trial is successful or not.

Conclusion & Template

We really hope this helps a little in your quest to a better life-work balance!

Not interested in reading any of this? Here's the Notion template. You can duplicate it and fill it with your own information.