Land Your Dream Job
Careers that help you move from intention to action

So You Want to Work Remotely? Part 2

Emily Lamia profile image

Emily Lamia

A woman with blue fingernails holds a mug that says, "The adventure begins."

You’ve considered all the factors related to working remotely. You now know why it appeals to you and you’ve considered your ideal remote-work situation.

So what else could be standing in your way?

Probably your workplace culture or your manager.

Making your case

Walking into your boss's office to declare that you should be allowed to work from home three days a week is probably not going to get you the results you’re looking for.

If you work for an organization that doesn’t offer flexible work options, you’re probably going to have to make your case, wait a while, and work up to your ideal situation. Here are some incremental steps you can take:

  • Consider starting the conversation during your next performance review. Mention that you’ve been thinking about the benefits of working remotely and make your case as to why it will improve your work (brings notes). But if the performance review isn’t going as well as expected, hold off!
  • When the timing feels right, ask to try working outside of the office one day a week or a few days every other week for a finite period to see how things go. This way, you can present it as more of a temporary experiment and rather than a permanent change.
  • Proactively draft a formal understanding or agreement for a specific trial period. In your agreement, outline responsibilities or goals for your work during that time period. This shows you’re taking this seriously and are committed to ensuring that it has a positive effect on your work.
  • Bonus points if you come up with metrics to track how the new arrangement is positively impacting your work. For example, think about the type of work you routinely do and how long it takes you to do these things. Set a baseline for your work, like number of client meetings, blog posts, social media shares, or dollars raised you normally produce every month or quarter. Track your progress towards those numbers and see how your work product and output increases by having more flexibility or a different work environment. After at least three months of your new remote work arrangement, tally up those results and draft pros and cons to present to your boss. Hopefully, you’ll have lots of pros to support upping your remote working days to whatever is ideal for you.

It’s important to remember that in many organizations, working remotely is simply not allowed, so even if you’ve made a great case for yourself, it may not be in the cards.

For managers

If you’re willing to test out a flexible arrangement for your staff, you’ll want to have your own agreement. Setting specific tasks or goals will ensure that everyone involved knows what’s expected of them. This makes it a lot easier to confirm that the new arrangement is working. It also makes it easier to show your staff why it’s not working in case the arrangement doesn’t produce the agreed-upon results.

What’s next?

Let’s say you have the conversation with your boss and for some reason it doesn’t turn out to be something you’re able to do. Now may be a good moment to return to the question of why it’s so appealing.

If you want more flexibility to travel, you might ask for more vacation time in your next performance review, or even a sabbatical of a month or two if you feel you’re a real asset to the organization and have been there a while.

If you can’t focus because of your office’s open floor plan, ask if you could spend three or four hours every so often working from a coffee shop nearby.

For managers:

If you’d like to offer the option to your staff, but leadership isn’t in favor of testing it out right now, troubleshoot with your team members to see what other arrangements could satisfy what it is that they are looking for.

If you are able to make the leap, there are tons of resources, experiences, and communities popping up to cater to your needs. In particular, we’re especially excited about the number of startups out there that are making it easier for you to travel and work remotely with a community of like-minded professionals. There’s Remote Year, Unsettled, and others. If you’re working on your own idea, Hacker Paradise might be for you.

And if you just want to work remotely for a few weeks, check out Roam or Nomad House, which offer community living and working arrangements that you can stay in for a week or a few months and aren’t tied to a specific itinerary or group.

And drop me a line when you realize you’re still in your pajama pants and haven’t brushed your teeth since you got up because you got started working on something and you suddenly realize it’s 11:30 a.m. Welcome to working remotely.

Did you enjoy this post? There's plenty more where this came from! Subscribe here for updates.

Emily Lamia profile image

Emily Lamia

Emily Lamia is the Founder of Pivot Journeys, which offers career coaching, group programs, and organizational consulting to teams that want to build strengths-based cultures that increase engagement, collaboration, and productivity.

Explore Jobs on Idealist