When To Know You’re Ready to Work From Home (And How To Ask Your Boss)

Want to work from home? You need to demonstrate your ability to successfully work from home and know how it will benefit your job, team and company. This can help!

We’ve all fantasized about quitting our 9-to-5 office jobs to work from home. Working from home has become the veritable Holy Grail of workplace arrangements. 

But are you prepared for all it entails and further, are you ready to be a pioneer?

Because for companies who are 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. 

So if you’re considering suggesting a telecommuting gig, here are nine questions to ask yourself.


Questions To Ask 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 in order 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 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. With a little work and dedication, you could very well find yourself answering ‘yes’ to all of them in no time.


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. So congratulations – you’re ready!

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.

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.