Career Woman

Want to work at home? Here’s how to convince your boss


Imagine if you could grab your laptop and work productively away at the local Starbucks. You’d sip a Grande latte and savor a lip-smacking warm croissant. No more waking up at six AM and being cooped up in a cube all day. Wouldn’t that be nice?

The good news — A whopping 56% of jobs are compatible with remote days. Yours might be one of them — All it takes is to convince your boss.  This guide shows how.

Sidenote: Do a performance self-check

Here’s the thing: Your performance needs to be topnotch if you want to enter the digital nomad lifestyle. Why? Most managers are either hands-on or off depending on employees’ performance. The better you’re at your job, the more autonomy you get. But… If you lack technical skillsets and have trouble keeping up, you’d better stick to the office like superglue.

How do you know if you’re a high-flyer?

  • You get a boatload of positive feedback and less sound criticism.
  • Your performance reviews are evergreen.
  • You work in concert with colleagues.

Not a top performer yet?

Here’s how to catapult your performance:

  • Go above and beyond (g., always under-promise and over-deliver.)
  • Take more responsibilities (g., volunteer outside your department.)
  • Show initiative (g., introduce small changes that’d streamline the workflow of your department.)

Have the conversation

You only get one shot, and you don’t want to blow it. Otherwise, it’s back to the ambient chatter of your peers that’s already burned into your earholes. So crack on to learn how you can tip the scales.

Communicate your motivations

You want to plunge into a cushy armchair and wrap yourself in a blanket. But—Your manager needs a better excuse. So when you broach the subject, communicate either professional (1) or personal (2) reasons why you want to be in a remote capacity.


  1. Back-to-back meetings and a constant stream of conference calls make it challenging to focus and deliver. Working remotely will help me kill distractions.
  2. I’m feeling the tugs of life (e.g., child care responsibilities, taking care of aging parents). If I could work remotely, it’d revive the work-life balance for me.

Present perks

Your manager needs to know what’s in it for him.

You need to prove you can bring something extra to the table when you go remote.

So…serve it upfront.

Here are some examples if you’re a copywriter:

  • I can be more productive because I’ll be able to write two articles instead of one per week thanks to fewer distractions.
  • I’ll be able to start working at 8am because I won’t have to commute.

Pro tip: Approach your manager during peak season to up the chances. It’s when managers look for employees to put in extra time and effort to meet deadlines.

Address concerns

It’s been silky smooth so far. Now…You need to address the potential buts that might’ve blossomed on the manager’s side.

●     How will you work with peers?

E.g., I’ll be available in Slack. If the team needs me to attend a meeting, we could use Skype or I could physically come to the office.

●     How will I know you’re working but not watching daytime TV?

E.g., I’ll log in to the company system, and you’ll be able to reach me anytime during the day.

●     What about security issues?

E.g., I could get the IT guys to look at my laptop to make sure my gear is safe. I can also use VPN (virtual private networks) to keep things private.

●     What if it doesn’t work out?

E.g., I suggest we start with a trial run. We can agree on success and failure metrics. If I fail, we can scrap the experiment.

With these out of the way, there’s a 98.4% chance your remote request will be approved. If not…

Don’t give up

Managers — like most people— don’t like change. Maybe it’s too uncomfortable for them, and they need to chew on the idea for some time. Here’s what you can do to get things moving:

  • Ask for the manger’s reasoning why he won’t let you go remote.
  • Don’t be pushy but ask if you can still discuss the topic.

If yes, keep the conversation rolling.

About Max Woolf

Max Woolf is a writer. He’s passionate about helping people land their dream jobs through the expert career industry coverage. In his spare time, Max enjoys biking and traveling to European countries. You can hit him up on LinkedIn.

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