Remote Work Advocates: Is It OK to Ask for Remote Work?

By Stephanie Ansel

Is it okay to ask for remote work? Yes, you can – but there are a few super important things to know first!

As someone who’s worked from home for years, I’m pumped to share insider tips on how to successfully negotiate remote arrangements.

This info will help you get the flexibility and freedom you deserve.

First, I’ll walk through the major upsides and potential downsides of remote work.

Knowledge is power, people! Then we’ll dive into smart strategies for getting your company on board, like crafting a rock-solid proposal.

By the end, you’ll have my proven playbook to win over even the biggest skeptics.

Let’s do this! I’m throwing in some of my favorite remote work memes to keep things fun too.

Asking to work remotely can feel scary.

But with the right approach, you totally got this! I can’t wait to see you thriving in pajamas…err I mean “work clothes”…at home soon.

Let’s get started and change your work life for the better.


Is it ok to ask for remote work?

It’s absolutely okay to ask for remote work when it aligns with your needs and job responsibilities. Open communication with your employer can lead to flexible work arrangements that benefit both parties. (1)

Should You Ask for Remote Work? Weighing the Pros and Cons

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Source: Running Remote

As someone who’s worked remotely for years, I’m often asked – should you ask your boss for a remote work arrangement? Well, let me walk you through the key pros and cons I’ve experienced first-hand.

There are compelling arguments on both sides that are worth understanding before deciding.

On one hand, working from home or a flexible location provides tons of nice perks.

You can ditch the stressful, time-sucking commute and get those extra hours back in your day.

I love being able to do laundry or prep dinner between meetings – it helps me be way more productive overall.

And not gonna lie, rolling out of bed and right to my laptop feels pretty great!

But I’d be remiss if I didn’t mention some potential downsides too.

I’ve found it takes extra effort to build camaraderie and collaboration remotely.

Nuanced communication can also suffer without those casual in-person chats by the coffee maker.

And some companies simply aren’t equipped with the tools or policies to enable effective telecommuting.

My advice? Take an honest look at both the benefits and drawbacks before approaching your boss.

Make sure remote work aligns with your work style, personality, job duties and company culture.

If those stars align, go for it! A well-planned remote work proposal can unlock tons of advantages.

But if you foresee major struggles, it may be best to keep that office chair warm.

Tips for Assessing If Your Company Allows Remote Work

Is it ok to ask for remote work 2

Eager to work remotely but not sure if your employer is on board?

Here are my insider tips for subtly assessing if your company already embraces flexible work arrangements: (2)

First, scan the employee handbook cover to cover.

Look for sections detailing remote work policies, telecommuting guidelines, virtual collaboration procedures – anything that hints they support location flexibility.

If the handbook specifically prohibits remote work, that’s a red flag.

You can also try casually bringing up the topic in conversations with coworkers you trust, especially ones who have been there awhile.

Ask if they know of anyone working remotely or if they’ve heard talk of expanded telecommuting options.

Their reactions will provide valuable intel.

It never hurts to directly ask HR or your manager about remote work opportunities too, as long as you frame it more as an open-ended inquiry, not a demand.

Simply say you’ve heard of other companies offering remote work lately and are curious if they’d consider it.

Their response will likely reveal if your employer is open to the idea.

And don’t forget to look around your office – if you notice empty desks and coworkers Zooming in, chances are your company already embraces location flexibility.

Subtly investigating from all these angles can uncover if remote work is feasible at your particular organization.

When and How to Have “The Remote Work Conversation”

Is it ok to ask for remote work 2

Ready to officially pop the question to your boss about working remotely? Picking the right time and having an thoughtful game plan is key to getting to yes.

As a digital nomad, let me share some tips from my own successful remote work conversations that can boost your odds of success.

First, wait for a time when your boss seems relaxed and in an agreeable mood – you want them open-minded, not overwhelmed.

I like to casually float the idea after we’ve just wrapped up a productive meeting or hit a big milestone – they’re more prone to say yes!

When you broach the topic, come armed with logical points on how it benefits both you and the company.

I explained how I could eliminate my brutal commute and be more focused working from home.

I also highlighted proven stats about remote workers being more productive.

Appeal to their sensibilities.

Have realistic solutions ready for common concerns like collaboration, accountability and company culture too.

The more thoughtful preparation you demonstrate, the more they’ll trust you can make remote work succeed.

Lastly, propose a trial period as a low-stakes way to test the waters.

Offer to check in regularly and tweak processes if needed.

With this phased approach, you can alleviate any doubts and show remote work enhances, not hinders, your contributions.

Crafting a Convincing Remote Work Proposal and Plan

Want your boss to say a big yes to letting you work remotely? I’ve learned the key is crafting a stellar proposal outlining the advantages along with a rock-solid plan.

Let me give you the winning formula that helped me finally go fully remote.

First, explain how both you and the company will benefit.

Talk about how you can eliminate stressful commutes and focus more, leading to higher productivity and morale.

And highlight research showing remote workers are 20-30% more efficient – companies save tons on overhead costs.

It’s a win-win!

Next lay out your ideal remote schedule with exact hours you’ll be available for meetings and collaboration.

Stressing that you’ll remain flexible and accessible helps alleviate their worries about communication lag.

Outline what tech tools you’ll leverage too – video conferencing, instant messaging, file sharing and more.

Today’s apps make it simple to stay connected virtually.

Recommend new software if needed to enable seamless teamwork.

Lastly, acknowledge potential challenges like decreased camaraderie and propose solutions.

Ideas include occasional in-person team events or virtual coffee breaks.

If you have a rock-solid plan that covers it all, your boss will feel at ease giving remote work a chance.

Addressing Common Concerns and Objections About Remote Work

Even the most sensible remote work proposal can get shot down by a boss with lingering concerns.

Through my many negotiations, I’ve learned how to adeptly address those inevitable worries.

Let me share some common objections and how I overcame them to get the green light.

One of the biggest concerns is around accountability and productivity.

Bosses often think remote workers will slack off without constant oversight.

I point to studies showing remote employees are actually more productive overall when given flexibility.

I also reference my proven track record of meeting all deadlines and goals, which speaks for itself.

Another objection is fear of decreased collaboration and communication with teammates.

But I explain how tech tools actually enable instant connection – we can have quicker chats via Slack than playing in-person phone tag.

And research shows even remote teams bond when given opportunities like virtual coffee breaks.

The last worry I often hear is that company culture and close-knit community could suffer if employees are physically separated.

While it takes a bit more intention, culture can absolutely thrive remotely.

I propose regular in-person team events and activities to foster camaraderie even from afar.

A little creativity goes a long way!

With compassion and compelling counterpoints, you can gradually help bosses become remote work believers too.

Patience and persistence pay off.

Negotiating Remote Work: Strategies for Getting to Yes

Ready to negotiate working from home but want the best chance of hearing “yes”? As a longtime remote employee, let me share my proven strategies for collaboratively getting bosses on board:

First, avoid ultimatums or demands.

Broach the conversation in a flexible, open-minded way.

Ask about their concerns and be prepared to find compromises, like committing to occasionally come into the office.

Next, thoughtfully articulate the benefits for both sides.

Bosses care about the company’s interests.

Emphasize how remote work can boost productivity, retention, and cost savings based on research.

You can also volunteer to take on an extra project or responsibility.

Demonstrating you’ll go above and beyond helps position remote work as a privilege earned, not an entitlement.

And know that overnight transformation is unlikely.

Offer to pilot a short-term remote arrangement so you can prove it’s effective for your role.

Then leverage that success to gradually expand the scope down the road.

With strategic and empathetic negotiation focused on shared incentives, you can get employers to see remote work as an innovation that serves everyone’s needs.

Be the champion to guide them toward 21st century flexible policies!

Setting Yourself Up for Remote Work Success If Approved

Woohoo, your boss said yes to letting you work remotely! Now it’s time to set yourself up for success and show the naysayers that this can be a win-win.

Follow my proven playbook for making the most of your exciting new remote work life:

First, establish a dedicated home office space only for working – this keeps your brain in “professional mode” when you’re there.

Deck it out with any tools or tech needed to maximize productivity and comfort.

Next, communicate, communicate, communicate! Make sure coworkers know your availability and schedule.

Be even more overt with communication remotely to preempt any perception issues.

Don’t neglect self-care rituals either.

Take regular breaks to move around, hydrate, and stretch.

And maintain a routine that includes exercise and social activities – isolation can happen if you’re not proactive.

Lastly, over-deliver on goals and assignments, especially early on.

Knocking it out of the park will quickly erase any doubts about you slacking off at home.

Stick to this plan, and soon your colleagues will be jealous of your sweet remote gig! With some intention and effort, your home can become your workplace wonderland.


In conclusion, asking for remote work is like planting seeds of opportunity in the fertile soil of your career.

It may seem daunting at first, but by weighing the pros and cons, assessing your company’s policies, and crafting a convincing proposal, you can nurture those seeds into a thriving garden of productivity and flexibility.

Addressing concerns and objections with confidence and negotiating strategies will only strengthen your case.

With careful planning and preparation, you can set yourself up for remote work success and enjoy the freedom to bloom wherever you choose.



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