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How to successfully ask your boss to work remotely

How to successfully ask your boss to work remotely

The future of work is distributed, yet even in the wake of mass remote working during COVID-19, many businesses are still reluctant to introduce long-term remote policies. But the time for dithering is quickly running out. As more and more employees express the desire to continue remote work post-lockdown, companies will have to respond quickly (and robustly) to retain their best talent.

But what do you do if your employer simply isn't getting that message? Or if you've just returned to a strangely perspex office with no promise of a remote work review? This article's all about how to kickstart the conversation and successfully ask your boss to work remotely.

A new expectation

It’s clear that remote work isn’t just a passing fad; even before the COVID-19 pandemic, 66% of US companies were offering it, with 16% being fully remote. A new generation seeking flexibility, choice and autonomy is entering the workforce – and they increasingly expect remote work opportunities; and not just as a last resort response to a global health emergency.

In the interests of staying relevant, competitive and attractive, your employer should be open to the remote conversation. While you and your colleagues may have to raise it, it shouldn’t come as a surprise. Ultimately, if they completely dismiss your request or shut the topic down, they’re not likely to be someone you’ll enjoy working for long-term…

Starting the remote work conversation

Misunderstanding and mental rigidity lie at the heart of resistance to remote work.

Some objections are cultural: many employers – and even employees – have an entrenched “panopticon” view of the workplace that makes them believe people only work when there are being observed. It’s the kind of attitude that has made “working from home” a synonym for “slacking off”.
Others objections are structural: your boss may fear the effect remote work will have on collaboration, believing physical presence and “bums on seats” are requisite for a thriving, productive workplace. Some may also believe remote work takes a lot of effort to set up, involving a ton of research and lots of restructuring (spoiler: it doesn’t have to).

Being able to respond to these fears is essential when asking your boss to work remotely. You need to demonstrate you have thought carefully about your request, and considered how it will fit in with the rest of your team and culture. While you don’t have to cover every detail in your first conversation, here’s a loose framework for how to successfully ask your boss to work remotely.

1. Explain why you want to work remotely

Explaining your motivation is essential when making any request. It lends weight to your case by making it personal and helps your listener consider your unique set-up.

Really think about what you want to get out of remote working. Is it about cutting out your draining commute? Having access to a quiet, focused space for productive deep work? Breaking up the monotony of your routine? Correcting your work-life balance to spend more time with your family? Being able to better manage your mental health?

Data is great here – use as many examples you can to illustrate your points. Cataloguing workplace distractions, tracking the time it takes you to complete tasks in different environments, or just putting commuting time in perspective are great places to start.

Then clearly explain how remote work would help:

  • How would it improve your productivity?
  • Could you start working earlier?
  • How would you be more focused?
  • Would it improve the quality of your work?
  • How would you do your job better?

2. Clarify how it will benefit everyone

Of course, remote work isn’t just about you – and it can actually create inequality and resentment if implemented one-sidedly. You need help your boss see how the arrangement is good for everyone in the long-term.

There is no shortage of impressive remote work stats to help your case along here. Here are just a few to get you started:

  • Remote workers are more productive, more engaged and more satisfied
  • People who work remotely feel more valued at work – an essential factor for retention
  • Remote work reduces absenteeism, since remote workers take fewer breaks and sick days
  • Flexible working supports the physical and mental health of employees
  • It offers a greener working model
  • Companies can access a wider (potentially global) talent pool
  • Remote work reduces costs for employees and businesses
  • It makes employers more attractive, being prioritized over pay rises

To make these benefits really hit home, it’s worth doing a little extra research specific to your industry. Check job websites to see how many employers in your field offer remote work opportunities. Better yet, see if your employer’s direct competitors offer them! Ultimately, to attract and retain the best talent, your company will need to offer similar privileges.

3. Explain how it will work

Once you’ve covered the why, you need to detail the what. That means showing you have thought through potential complications and have a simple practical plan for how remote work will for you. First, cover practicalities:

  • What day(s) you want to work remotely
  • When you will be available (remote working hours)
  • Where you will work (e.g. a home office, a shared workspace, a library)
  • What you need to facilitate that (high-speed internet, secure VPN connection, home office equipment)

Then, provide a structure for overcoming a few common remote challenges:

  • How you will communicate and check-in with colleagues
  • How you will keep your progress visible
  • How your boss will know what you’ve achieved
  • What remote work “success” will look like

4. Lay out the tools you will use

A huge part of making remote work work comes down to your tools. Unwittingly, most companies already use virtual office tools without realizing it – like Dropbox, the G-suite, Slack, Skype, Zoom and Airtable. If you use cloud-based web tools to do most of your work, your company is already half-way there. To make things crystal clear, outline what tools you will use for what. A few things to consider include:

  • Collaboration – this completely comes down to your role. Chances are, you are already using remote-friendly web tools to facilitate team feedback, review and group work.
  • Communication – Slack for quick updates and check-ins; Zoom for group meetings and one-to-ones; email for clients.
  • Knowledge sharing – Dropbox for sharing assets, documents and files; Basecamp for big announcements and learnings.
  • Work progress – Todoist or Jira.
  • Workload, hours and activity – the automatic time tracker Timely.

While your boss will obviously want to take the lead, showing that have considered potential barriers and found software solutions to overcome them lightens that burden. It may even bring their attention to new possibilities they hadn’t considered before.

5. Show how you will measure if it’s working

Visibility is a huge stumbling block for managers when it comes to remote work. Even if your boss is sympathetic to your request, they need hard evidence to show it’s working to justify remote policies to their superiors. In terms of providing the right support and management, they also need a way to monitor your performance while you’re outside the office.

Workload, workflow, overtime, tasks and activities, productive focus, efficiency – all of these aspects of employee management can be easily gauged for remote workers. It just requires you to establish your performance benchmarks (or KPIs) with your boss and get the right tool to share that information openly and effortlessly.

As a 50:50 remote/in-house company, we’ve been dealing with remote performance management for a while – and we’re unashamed in using our own automatic tracking tool Timely for the job. We’ve fed our first-hand remote experience into creating a tool that helps managers and employees stay connected without invading anyone’s privacy. Being automatic, everyone can focus fully on their work – leaving Timely to gather and visualize individual performance data.


It’s hard to argue with a well-researched, empirical argument. Showing how you will measure your remote performance – and suggesting a solution to give your boss full visibility over it – offers exactly that.

Send this to your boss: time tracking for remote teams

6. Start with a trial

To ease your boss into the idea, and give yourself room to adapt, suggest trialling remote work (if you've already been tracking your performance while working remotely lockdown, you won't need this step!). That could mean only working remotely for one or two days a week, or trying out trialling a full-on remote set-up for just a couple of weeks. It provides you both with a safety net – softening a dramatic change into a palatable, manageable one.

Once you’re nearing the end of your trial, have a conversation on what’s working and what’s not. Review the performance benchmarks you agreed upon to consider how its impacted the way you work. Actually reflect on whether it’s right for you, and whether there were any unexpected drawbacks that might make it unsuitable longer-term.

Understand: despite the overwhelmingly positive PR, remote work is not without its problems. If you’re certain it’s still what you want, use your trial experience to create the right remote plan for you and your team for the future.

Final tips

  • Come prepared to lead the meeting
  • Research remote work in your industry and among company competitors
  • Track your performance before going remote to measure its impact on your work
  • Understand the tools needed to support remote work
  • Consider what remote work “success” will actually look like for you
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