From Temporary Fling To The Real Thing: How To Ask To Work From Home Permanently

At one time or another, we’ve all fantasized about quitting our 9-to-5 office jobs to work from the comfort of a couch in pajamas. Working from home has become the veritable Holy Grail of workplace arrangements. 

No commute saves time and money. There are never any weather delays. There aren’t chatty colleagues or micromanaging bosses patrolling the hallways. And let’s not even get into how amazing it is to work in athleisure.

And where it once felt like an impossibly lofty dream, it has now become a reality for so many, courtesy of a pesky pandemic. 

This then begs the question: How on Earth can we reasonably be expected to go back? Kicking and screaming, that’s how.

It almost seems cruel.

So for companies who are – or were a mere year ago – still four walls of brick-and-mortar, you may have your work – work, get it? – cut out for you as you broach the subject with your boss. 

If you’re considering suggesting a permanent telecommuting gig, here are some qualifying questions to ask yourself before you ask your boss.

Taking Inventory of Yourself

Ask yourself the following questions – and answer them honestly – before making your case to change your work arrangement. 

1. Am I self-disciplined and self-motivated?

Can you git ‘er done without the fear of your boss catching you scrolling on social media? Because you can – and will – be tempted to throw a load of laundry in the wash, but you’ll still need to keep yourself motivated.

2. Am I confident working without supervision?

Without a boss physically looming over you to nag, err, remind you about deadlines, projects or workloads, that responsibility will fall to you – and you alone. 

3. Are you laser-focused?

It’s hard to resist the siren song of every ding, ping and ring of every email, social media notification and text message that tries to interrupt your flow so laser focus will be all that stands between you and productivity. 

4. Are you organized?

Without face-to-face interaction – and fear of judgment of your slovenly workspace – it’s easy to let things slip through the cracks, literally and figuratively. You’ll need to be super organized to stay on task.

5. Are you a strong communicator?

A clever approach to maintaining the human element of virtual work is to remember to use ‘email as the pillar, and instant messaging as the glue.’ You’ll need to communicate, communicate and communicate some more.

6. Are you good at working alone?

Some people need human interaction to be productive. If you, on the other hand, find that you are more productive without water cooler meetings and cubical drop-ins, remote work might just be your cup o’ tea.

7. Are you good with connectivity tools?

File under: Does Not Compute. Virtual work isn’t compatible with technological ineptitude as audio and video conferencing, instant messaging, and other online meeting tools are mission-critical connectivity tools.

8. Do you have a well-equipped, well-designed home office? 

Just as it’s said that you dress for the job you want, your home office needs to be equipped similarly. A designated home office space that works well for you – and for the work you need to do each day – is a must.

9. Will working from home give you the work-life balance you want?

For many, working from home means they are afforded the flexibility they need to better accommodate their personal lives, like being more available for their children.


How’d you do?

If you answered ‘yes’ to all of these, good news! Telecommuting might just be for you. But if not, fear not! Many of these questions – if you answered ‘no’ – can be opportunities for growth so with a little work and dedication, you could very well find yourself answering ‘yes’ to all of them in no time.


Taking Inventory of Your Office

Here we’ve compiled a tactical checklist for determining if you’ve got the right – literal – stuff to work from home.

  • The Accessibility
    You need to know you’ll have access to everything you’ll need to get the job done.
    • Do you need a VPN or other security measure before logging in at home? 
    • Do you have access to tools you usually have and need at the office?
    • Get login information as needed for company firewalls.
    • Get access to information and files on cloud-based applications.
    • Add a digital calendar app to your phone.
    • Make sure you have reliable high-speed internet.
    • Forward your office phone and set up a remote answering service if necessary.
    • Know your point of contact for any technical troubleshooting. 
  • The Equipment
    You need to make sure you have all the necessary equipment to do your job.
    • Office-issued or home computer
    • Additional computer equipment, such as keyboards, mouse, printer, etc.
    • Second monitor as needed
    • Webcam and accompanying audio accessories as necessary
  • The Tools
    Consider what apps and tools you’re expected to leverage to do your job, and make sure you have access to all.
    • Asana
    • Basecamp
    • Google Drive
    • DropBox
    • Zoom
    • Microsoft Teams
    • Slack
  • The Space
    Make sure you have a designated home office space that works well for you and for the work you need to do.
    • Have a designated space for your home office 
    • Be sure your space doesn’t double as a common area for your family
    • Create a system for paperwork in addition to digital
  • The Routine
    Establish a routine just as you would if you had to leave for a brick-and-mortar office.
    • Make yourself some coffee or tea
    • Take a shower
    • Get dressed
    • Establish – and stick to – daily start and stop times
  • The Communication
    It all comes down to one – albeit hyphenated – word: over-communicate. Can you do it?
    • Leverage email, instant messaging, and video conferencing
    • Establish a regular meeting cadence, at least initially
    • Make sure you have a digital calendar that is up-to-date and accessible
  • The Plan of Action
    Manage your energy, guard your time, prioritize your work for maximum productivity.
    • Create an ideal workweek template. 
    • Determine when you’re at your best and schedule accordingly. 
    • Leave buffers – or blank spaces blocked out – on your calendar. 
  • The Expectations
    Make sure you’re clear on what the expectations are of you and your role.
    • Availability 
      • When you’re expected to be ‘online’ by phone, text, email, chat, etc.
      • When you’re available, communicate this in advance
    • Productivity 
      • Understand your shared objectives 
      • Understand your measurable objectives
    • Meetings
      • Know which meetings are mandatory 
      • Know if meetings are weekly, monthly or quarterly
      • Know how you’ll meet, such as Zoom, Skype, Google Hangouts, etc.
  • The Distractions
    Make a conscious effort to minimize distractions during your working hours.
    • Music: Pick a station or album and then let it play through.
    • Pets: Keep pets crated or confined to a room.
    • Kids: Explain the importance of quiet time or make childcare arrangements.
    • Household chores: Handle chores during breaks or before/after work hours. 
    • Deliveries & visitors: Decline knocks at your door to guard your time and focus.

Popping The Question: How To Ask Your Boss

Now, the real test: Asking your boss.

The best time to discuss working from home is after you've done your homework – also known as everything we covered above. 

Because while a sustainable, long-term work-from-home arrangement will require significant pivots in your leader’s mindset, practices and communication methods, it is inarguably the direction many workforces are moving. 

It’s currently a white-hot topic in articles and trending news – but even in less tumultuous times, many companies had been gradually testing the remote work waters to determine if going virtual could be a long-term, sustainable possibility for their organizations.

Simply put: The iron’s hot; it’s your time to strike.

The pandemic turned ‘Can we make this happen?’ to ‘It’s happening to ‘How can we make it sustainable for the long haul?’

You can even lean into what some major industry leaders are doing, too.

“According to news reports, a wide array of prominent businesses have agreed to allow staff to permanently work from home, including tech giants Microsoft, Facebook, Twitter, Square and Shopify. Even Deutsche Bank is considering allowing remote work two days a week. 

“Meanwhile, Morgan Stanley CEO James Gorman said in April that his company has "proven we can operate with no footprint" and that it will have "much less real estate" eventually. His statements echo findings by Moody's Analytics, which recently revealed that commercial real estate was under pressure well ahead of the Covid-19 crisis.”

Now, you need to be ready, willing and able to discuss – and ultimately sell – your ability to successfully work from home and how it will benefit your job, team and company. This article will help you make your case. 

Be prepared, be confident and be flexible

Your boss may not be ready to jump into remote work with both feet – yet – so be open to a counteroffer of a combination of working in the office and at home throughout the week. 

In time, you could prove not only that you’re more than capable of working productively from home, but you could blaze a trail for your teammates who long for the same. 

You trailblazer, you.