Tricking Your Boss To Allow You To Work From Home

SUMMARY POINTS

> Use your boss’ immediate urgent needs as the primary factor
> Ask to work from home to concentrate on urgent projects 
> Prepare and plan ahead to capture remote work opportunities
> Overdeliver on your results and prove your effectiveness 

It’s a dream for millions of office workers to be able to work from home.

Imagine - no dreaded commute to and from the office, no getting dressed up for work, no dealing with work jerks, no office distractions and noise, etc. - just pure interruption-free productivity.

And for those having to juggle the complexities of childcare logistics...OMG, working from home is truly a godsend solution.

There are a lucky few that work for companies or have jobs that allow remote work or telecommuting, either on a part-time or full-time basis - we’re super jealous and envious of those folks.

According to research firm Global Workplace Analytics, only about 3% of the total US workforce telecommutes at least half of the time. This excludes self-employed work-at-home people because they’d skew the data. So, it covers normal salaried working stiffs like us.

So, among full-time employees, the total percentage that work from home is still very low, but it’s been growing slowly and steadily over the years.

For the larger 97% majority of us working professionals, we’ve got to physically go to an office five days a week and keep a seat warm for eight hours a day.

Most employers, we’d guess at about 95% or so, don’t offer any kind of flexible working options - either flextime or working remotely from home.

So, what can we do to get around this?

We can’t just decide to not show up at the office and work from home on a whim - that’ll just get our asses fired.

We’ve gotta creatively capture an opportunity for working from home and then, build your boss’ confidence in your output and repeat the success to make it stick for the long-term.

Here’s The Trick: Use An Urgent Task Or Project As Your Basis To Kick-Start Working Remotely From Home

Have you ever experienced the joy of a sewage backup in your house and not being able to use any of the toilets? Or, a flat tire while driving on the highway?

In those kinds of crisis moments, the only thing that mattered was to get that issue fixed and sorted out so that you can get back to your normal day-to-day life.

Did it really matter who and which company fixed the problem for you?

Nope.

All you cared about was to get the problem solved - quickly and efficiently.

Did you stick your nose into their work while they were fixing the problem?

Nope.

You left them alone, stayed out of their way and let them do their thing so they can get you back in order and functioning properly.

A similar kind of scenario plays out for your direct boss - probably on a weekly, if not daily basis.

Every single day in the corporate world and elsewhere, middle managers are often given last-minute urgent tasks and/or requests from executive or senior management that needs to get done asap.

That middle manager, who’s probably your direct boss, then sorts the tasks among the team. And, you get your portion of the work - as the saying does, “the shit rolls downhill.”

Here, you’re that flat-tire repair guy or the emergency plumber. Your boss is the one urgently needing your help.

He or she knows that you’ve got other projects pending, some of which are also important for the team. But, this one is above all others, so you’re forced to put everything else on hold and focus on this request.

This is an opportune moment to ask your boss if you can work from home.

The conversation or email may play out something like this:

“Hey John, I know that this is a top priority request from upper management and that we need to get this done asap.

I’ve got a ton on my plate already with other pressing stuff. But, I can get this done for you quickly, if I can get away from all the interruptions at the office.

Let me work on this from home so that I can concentrate on this 100% without all the noise and chaos here.

Would you be okay with me working remotely tomorrow and getting this done for you?”


Your statement will surely vary from the above generic one, but the tone must be the same. It’s one of cooperation, dedication and support.

This is not about you getting to work from home. It’s about your boss and what you can do for him/her on this pressing issue.

It’s more about “what’s in it for them” than it is about “what’s in it for you.”

If you take a self-centered approach instead of a position of giving, it won’t work. You have to put your boss’ immediate needs first. And if you can clearly express that, it’ll improve your chances.

And, the more urgent the project request is, the more open and willing your boss will be to allow you to work from home to get the job done. After all, it’s in his best interest that you complete the task quickly so that he can review and then, subsequently submit the output to upper management.

If things line up in your favor and your boss agrees to let you work from home, you must execute and exceed your boss’ expectations. You need to be at 110%.

Read that again.

This is incredibly important because your results will determine whether or not it’ll happen again and lays the groundwork for any future work from home options.

If you botch this, your dreams of working remotely go right down the shitter.

Things We Didn’t Know But Wished We Did

There’s more to this than just straight up asking your boss to work from home. You need to do some prep work ahead of time. This will improve your chances of getting this off the ground and working.

Here are a few things that we’ve learned through our experiences that we wished someone told us beforehand.

Read through them - it’ll come in handy, trust us.

1) Plan & Practice Your Statement Delivery

There’s nothing worse than bumbling through a conversation, blurting out random things and confusing your boss on what you’re trying to get at. When your thoughts and intentions aren’t lined up and clear in your head, it’ll just come out of your mouth in one big verbal mess.

Things get worse when you know that you’re asking for something out of the ordinary. You get nervous and jittery, especially if you’re more of an introvert.

To avoid this potential face-palm, get your thoughts in order and write down a few responses and practice saying them out loud - seriously. So, when the time comes...and it will, you’ll be ready.

Otherwise, use email. Have a clean-n-simple draft ready-to-go with fill-in-the-blank spots for the specifics. Of course, use this only once. Don’t use it as a template for future requests.

Once you make the first request, future requests will feel more natural, especially if the original was accepted.

2) Use Method For Only Urgent Larger Items

If the project isn’t truly urgent and/or it’s a smaller request, there’s less likelihood that your boss will take up your offer to work remotely.

Less urgent requests can be pushed off until later or even the next day. And, smaller urgent tasks that can be done in a couple of hours can’t justify a full day of working remotely.

So, only give this a try when you know for sure that it’s a big important task for your boss that will take a substantial amount of time to complete - like most of a full day.

This is your “silver bullet” - use it wisely the first time and you’ll get another. 

3) Get IT Stuff Sorted Out Ahead Of Time

We learned this the hard way. Some of us don’t have a laptop but work off of a desktop computer at the office. So, we sent work files to our personal email and also used a USB stick so that we can work on the files at home.

This was a big no-no in the eyes of IT security policies.

If you don’t have a laptop for work, get with your IT department ahead of time, get prepped for an on-demand loaner laptop and do a couple of test logins with them. So, when the time comes, you can easily just ask for a loaner laptop to work remotely and you’ll be familiar with how to access email and other internal company resources online.

If you do use a company provided laptop, check with the IT department on any specific VPN, security login processes, etc. Do a trial run so that you’re comfortable with the process.

You don’t want to be in a situation where, on your first remote work day, you spend the first half of your day sorting out IT issues with the helpdesk folks.

4) Propose Mid-week Days For One Month Trial 

If you’ve been successful in working remotely a few times and your boss is happy with your resulting output, you can propose a short trial run of one day a week for one month.

Your proposal should be simple and straightforward. Don’t put together some huge-ass Powerpoint presentation with research stats and case studies. Your boss doesn’t care about that shit.

What your boss cares about is your performance and output in completing your tasks and supporting the team.

Depending upon what your working relationship is like with your boss, this proposal can be an informal conversation or a well-organized email. You know best, so go with what you think will communicate the proposal clearly.

Lastly, propose Tuesday, Wednesday or Thursday as your selected day for working remotely, not Friday or Monday like we originally did (it got shot down fast).

Here’s why - asking for Friday or Monday comes across as just a weekend extension tactic. However, mid-week days are the beefiest part of the work week. It’s when workloads can be heaviest and you can get some serious “heads down” work done.

The mid-week days also tend to be the heaviest in terms of commuting traffic. So, you’ll be saving more money on gas on those days.

5) Look For Other Opportunities To Prove Yourself

Don’t limit yourself to just the urgent tasks and projects that roll down to you from your manager. There are other key opportunities where you can request to work remotely.

Here are a few examples where it makes sense to work remotely:
- Bad weather like snow/ice storms
- Waiting for the cable company
- Being sick but able to work
- Early morning or evening calls
- Big home deliveries

If you really want to stand out, you can opt to work remotely on a day where the office is closed due to a holiday. This isn’t something we’d normally recommend, but it does make a clear statement to your dedication.

Just don’t make a habit of this one - you do need time away from work to relax-n-recharge.

6) Be Accessible, Productive and Responsive

This is obvious, but worth mentioning here because it’s so important. When you’re working remotely, your absence from the office has implications.

When you’re “out of sight”, you’re also “out of mind” for everyone there.

All of those informal hallway discussions and the stop-by cubicle chats with fellow co-workers to follow up on things or ask quick questions will disappear when you do.

So, you have to be overly accessible when working remotely. Make your presence known online with quick email replies or messaging chats.

And be open to having video calls with colleagues and/or customers. Just be sure to lock-out all potential interruptions or you might be like this guy.

VIDEO: Children interrupt BBC News interview - BBC News
YOUTUBE: BBC News
LENGTH: 0:43

Summary points:
> Don’t make a rookie mistake of not locking the door
> Best floor slide we’ve seen since Tom Cruise in Risky Business
> Who knew the BBC had a sense of humor posting this

While video calls will probably be a bit rare, phone calls won’t. In fact, have live phone discussions in lieu of back-n-forth email dialogue when it makes sense.

The only exception to being very accessible is when you’re heads down focused on a task or project.

Productivity tactics like time-blocking and pomodoro sessions require you to eliminate all distractions so that you can get in the zone and concentrate deeply.

But, when the session is done, be sure to get back online.

The Opportunity To Work Remotely Will Happen Sooner Than You Think

You can just sit there and say to yourself, “that was a nice article” and just go back to tapping on the keyboard. But, when the moment arrives and you’re not ready, you’ll be kicking yourself.

So, don’t get caught off guard.

Be prepared and you can capture the opportunity to establish a new norm at work - one that has the potential to provide more job satisfaction and productivity than ever before.

Who knows, if everything goes really well, you just might be the pioneer that breaks the traditional work week into a more progressive and flexible one, not only for yourself, but also for others.

Then, everyone will be on a happy hunt to find great remote working spots in town.

You’ll be the office hero.

Feel Better,
[Cubicle|Therapy]