EASY Steps to Convince Your Boss to Let Your Work Remotely Permanently [Using Quarantine as Unofficial Trial]

People ask me all the time – how do you become a digital nomad?  

And I generally have 3 answers…

1)   Choose a career that lends itself to remote work….these types of jobs include computer programming, web development, graphic design, coding, digital marketing, social media management, writing, teaching, transcribing, translating, data entry, etc. 

2)   Kill it at your current job and then convince your boss to let you go remote

3)   Become your own boss and do whatever you want

But currently, I have a new piece of advice.  

The coronavirus pandemic that has swept across the world is an utterly terrible thing (don’t get me wrong at all) – but out of it, we’ve already seen a few glimmers of hope…air pollution has cleaned up without all the cars on the roads, evictions have been banned, water shutoffs suspended, Universal Basic Income suggested by conservatives, and countries, companies and individuals are rising up to help one another.

So many there are some important lessons that we can learn from this pandemic.

One of which (and something I’ve been saying all along) is that remote work DOES work.  

And it doesn’t have to be positioned as this super unconventional or outlandish way of working. 

In fact, it’s an even better way to work – because greater flexibility leads to more creativity, productivity, and loyalty.

So back to my new piece of advice – and what I would recommend to Nomad hopefuls.

Use this quarantine time to your advantage.  And make something positive come of this terrible situation.

Show your boss that working remotely won’t hinder productivity, distract you, or hurt the business.  

So during the quarantine, here are some steps you can take to lay the ground work and PROVE to your boss that location independence works and CONVINCE her to let you continue being remote after this is all said and done.

STEP #1 – Set up weekly check ins with your boss.  

Right now (not tomorrow or in two weeks), drop your boss a note and ask her if you can set up weekly check-ins.  

Explain that you want to provide a clear line of communication during the lockdown and make sure she feels in the loop with everything you have going on and that all projects continue moving forward seamlessly.

The reason I am saying to do this TODAYis because who knows how long the quarantine will last, and you want to get set up for success right away.  Getting out in front of it FIRSTand requesting the check in also shows that you are taking initiative to help the business continue to meet it’s goals.

Once you have a weekly date on the calendar to check in with your boss, make sure you always arrive to these meetings fully prepared and with an agenda.  No one likes their time wasted so make sure these chats are short, sweet but useful – running thru updates on all projects, asking any questions you need answered, and answering any of your boss’s concerns.  

I would also recommend you frequently check in with your boss on how your performance working remotely has been (this will come up again later )

Come to the table with new ideas and pitches as well!  This will show your boss that you aren’t just doing the bare minimum but are using your time wisely to brainstorm ways to push the business forward.

Here are some other helpful readings:

How to Have a Successful One-on-One With Your Boss (Even If You Don’t Get Along)

How to Make the Most of Weekly One-on-Ones With Your Boss

STEP #2 – Take the lead on establishing a video conferencing system for meetings within your group.

One of the best tools in any digital nomad’s kit is a great video conferencing setup and rhythm.  Use this time to figure out what video conferencing platform works best for your team and why.  

Play around with different systems (on your own time; not when a meeting is starting!) and come up with best practices.  Every team functions a little differently and will have different needs.   

For example, maybe in lieu of in person meetings, creating a deck to follow along in a video conference would be useful.  It’s also a great way to keep organized focused and on the task at hand. 

I know a lot of people love Zoom (especially right now!)  Another favorite video conferencing platform of mine is 8x8.  Great image quality and easy to use.

The point of this step is to already have an established video conferencing system in place that is working well, so that when you ask your boss to continue working remotely you can point to this method (that has a proven track record!)

Here are some helpful resources:

The ultimate guide to remote meetings in 2020

7 Tips for Using Zoom Video Conferencing with Remote Teams

Remote Meetings 101: Everything You Need To Know

STEP #3 – Kill it at your job.  

Being a stellar employee is the number one method to getting what you want.  

There are a lot of distractions right now….both going on in the world, and potentially at home (hello Fido and kitchen snacks).  But you can’t let that stand in your way of proving to your boss how amazing you! 

You need to step it up and make sure there aren’t ANY reasons to site for why working remote hasn’t worked during the quarantine.

Make sure everything you touch is done on time and in impeccable shape.  Make sure you are being a team player and helping your colleagues out.  Be the calmest person in the room, and the most reliable.

This is a time when people might struggle – but make sure that person isn’t you.  Be the easy one on the team, the one your boss never has to think twice about.

Now is the time to go above and beyond….while others are leaning back in this disaster, make sure you lean in.

Take some time each day to think about what you can do to go the extra mile.  What can you do to a solve a problem at the company?  What can you do to solve a problem for a client?

If you need ideas on how to be a stellar employee, check out some of these articles:

47 Habits of Highly Successful Employees

7 Ways to Be Your Boss’s Dream

20 Things the Most Valued Employees Do Every Day

STEP #4 – Record your accomplishments

This is something that is useful to do no matter what you end goal is – RECORD YOUR ACCOMPLISHMENTS. 
Whether you are updating your resume, interviewing with another company, or just trying to get your boss to let you work remotely, it’s an important skill to learn.

With your accomplishments in hand (especially those done during the quarantine), you’ll be better prepared to pitch continuing to work remotely to your boss. 

You want to be able to remind your boss how useful you are to her and the organization as a whole.  Because these are the types of people that managers strive to keep around….no matter what it takes.

Check out some of these articles for more info on recording your accomplishments:

Keep Track of Your Work Accomplishments Throughout the Year

How to Keep Track of Your Work Accomplishment

STEP #5 – Back up your ask with research  

Now that you’re armed with a successful remote work track record and a list of accomplishments, let’s support this with research.

Remote workers are generally happier – as they are able to find a better work/life balance….and happier employees generally work harder and show greater loyalty.  Things any boss wants, am I right?!

Not to mention 65% of employees think they would be more productive working from home as well due to fewer distractions, fewer interruptions from colleagues, reduced stress from commuting, reduced office politics, etc. (Flexjobs 2018).

There’s also a monetary benefit to employees working remotely as well….as employers don’t have to worry about as much office space, parking, etc.

For ideas on how best to build your case, check out these links:

Flexjobs Remote Work Statistics

45 Key Remote Work & Telecommuting Statistics for 2020

Case Closed: Work-From-Home Is the World’s Smartest Management Strategy

STEP #6 – Schedule time to discuss the ask with your boss

Since you already have your standing meeting with your boss, that’s a perfect time to bring up your ask. 

Ahead of time, make sure you have prepared a written proposal that will detail how this will work and anticipate any concerns your boss may have.

Thinking thru your boss’s likely objections ahead of time, will pay off greatly in the moment.  Come up with responses for how you will address so you feel more confident in the moment.
Once in the meeting, be prepared to lead the conversation.

Start off by explaining how well this work-from-home trial has worked for you – insert whatever your individual reasons are for wanting to work remotely (better work/life balance, enhanced productivity, etc.)  

But don’t make it all about you.

Mention that you’ve received excellent feedback on your remote work performance during the office’s closure (remember how we told you to do check ins with your boss and specifically ask how you were doing?  See how smart we are?!)

Here are a few resources to help you prepare for the ask:

How to Convince Your Boss to Let You Work Remotely (Worksheet Included!)

How to Write a Telecommuting Proposal

How to Ask to Work from Home (with Exact Scripts & Email Templates to Aid Your Negotiations)

Having already spent over a month working remotely and building up your boss’s trust, her concerns should be minimal and your chances of success high!  But don’t be discouraged if she doesn’t immediately jump at the idea.  

Be patient, and don’t lose sight of the goal. 
And remember – even if this job won’t let you go remote permanently, hope isn’t lost.  Perception and trust in remote work is swiftly evolving.  And I have no doubt that we will see a stark rise in the number of remote roles around the world post-corona, as companies look to reduce overhead and keep their employees safe & happy.

What are your thoughts on this?! Share with me in the comments below. But FIRST, make sure to share this pin!!