How To Ask Your Boss To Work Remotely (And Get Them To Say Yes)

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We live in a world that's more connected than ever before.

From startups to multinational corporations, the digital age has paved the way for remote work to become not just feasible but, in many cases, preferable.

Yet, taking the plunge and asking to work remotely can be daunting for many. How do you make the pitch?

How do you navigate the waters and secure that precious "yes" from your employer? Let’s break it down.

1. Start With The Why

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Just as Simon Sinek champions the idea of ‘Start With Why’, begin by asking yourself why you want to work remotely. Is it to avoid the daily commute, have a better work-life balance, or perhaps to immerse yourself in a new culture while working from a different country? Your ‘why’ will be the foundation of your pitch.

2. Research & Prepare

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It's one thing to want to ask to work from home, but it's another to show that it's beneficial for the company. Present studies and statistics that showcase the productivity and benefits of remote work. Sites like Buffer and Owl Labs often provide comprehensive reports on the state of remote work. Be prepared with facts that support your cause.

3. Address Concerns Proactively

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When it comes to shifting traditional work paradigms, objections will arise. However, the trick is to anticipate these concerns and address them even before they're voiced.

Before your employer raises concerns, tackle them head-on. Talk about the measures you'll take to ensure productivity and regular communication, and how you'll manage time zones if you're considering moving further afield. It's all about proactively demonstrating that you've thought this through.

  • Productivity: One primary concern is that remote work might decrease productivity. To counteract this, outline the specific tools and techniques you'll employ to maintain, or even boost, your efficiency. This might include productivity apps, strict scheduling, or even time-tracking tools that provide transparent reporting on how your time is spent.

  • Communication: Highlight how you'll use communication platforms like Slack, Microsoft Teams, or Zoom to ensure you remain a cohesive part of the team. This is also where you emphasize your commitment to regular check-ins and updates.

The more you can show you’ve considered potential pitfalls and have strategies to mitigate them, the more confidence your employer will have in green-lighting your proposal.

4. Showcase Past Successes

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Remember that time you had to work from home because your car broke down, and you ended up completing that project ahead of schedule? Bring it up!

Demonstrate that you've been effective when working remotely, even if it's been sporadic.

Using evidence from your track record is an excellent way to build a case. Concrete examples of your efficiency and dedication when working remotely can be persuasive.

Reflect on times you had to work outside the traditional office setting. Maybe it was a weekend you had to pitch in or days you had to work from home due to unforeseen circumstances.

Quantify your successes if possible.

Did you complete tasks faster?

Did you manage to do more within a shorter timeframe?

Get testimonials or feedback from colleagues or superiors that highlight your effectiveness during those times.

Your past actions are the best indicators of your future behavior. Showing a history of successful remote work can reassure your boss that this is a well-founded request.

5. Suggest a Trial Period

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Instead of diving head-first, suggest a month-long trial where you "ask to work from home" for a defined period.

This reduces the risk for your employer and allows you to prove that this arrangement can indeed work.

Jumping straight into full-time remote work can be a big step for both you and your employer. Easing into it can make the transition smoother.

Propose a short-term test run. This allows both sides to evaluate the arrangement without a long-term commitment.

Set clear criteria for success. What will you aim to achieve during this period? How will you measure productivity and efficiency?

At the end of the trial, be open to feedback. Discuss what went well and what could be improved.

Takeaway: A trial run provides tangible evidence of how remote work can operate in practice, reducing the perceived risk for your employer.

6. Be Flexible

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Understand that your proposal is a starting point. Be open to feedback and suggestions.

Your initial proposal might not be accepted in its entirety, and that's okay. The key is to show adaptability.

While you might want to work remotely five days a week, be open to a compromise, like starting with two or three days. That’s still a win!

Consider hybrid models where you split your time between home and the office.

Be receptive to feedback. If there are particular concerns or conditions your employer has, take them seriously and see how they can be integrated.

Flexibility shows maturity and a willingness to collaborate, enhancing the chances of your proposal being accepted in some form.

7. Present the Personal Benefits

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While the company's benefits are paramount, shedding light on the personal advantages can also be compelling.

Discuss the time saved from commuting and how that time can be reinvested into work or self-improvement activities that can, in turn, benefit the company.

Talk about how a conducive and personalized work environment can lead to increased creativity and motivation.

If you're considering traveling to a new city to work, share how exposure to diverse cultures or work methodologies can provide fresh perspectives and innovative ideas.

Takeaway: Personal benefits don't just improve your quality of life; they can also lead to professional growth that benefits the company.

8. Have the Right Tools

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In the realm of remote work, tools are your bridge to the team. Having the right arsenal not only ensures smooth communication but also demonstrates your commitment to maintaining efficiency and team cohesion.

  • Communication Platforms: Slack, Microsoft Teams, or Google Chat can keep you in constant touch with your team. They facilitate immediate communication, much like the quick chats you’d have if you popped over to a colleague's desk.

  • Video Conferencing: Tools like Zoom, Google Meet, or Microsoft Teams (again, it’s versatile) ensure face-to-face communication. It’s an essential aspect, especially for team meetings or when nuanced conversations are required.

  • Collaboration and Productivity Tools: Platforms like Trello, Asana, or can be used to track tasks and projects. Google Drive or Dropbox can facilitate file sharing and collaborative document editing.

  • Cybersecurity Measures: Especially crucial if you're accessing company files from home. Virtual Private Networks (VPNs), trusted antivirus software, and encrypted communications tools can provide assurances that security won't be compromised.

By showcasing that you've equipped yourself with top-tier tools, you send a clear message: you’re serious about making remote work effective and seamless.

9. Set Clear Boundaries & Expectations

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While flexibility is a hallmark of remote work, it’s essential to establish boundaries. This ensures both you and your employer have a clear understanding of the work modality.

This starts by defining your work hours. It’s crucial to define a general timeframe when you'll be at your most productive and available. It doesn't have to be a strict 9-5, but there should be consistency.

Specify periods when you'll be online and available for immediate communication. Also, clarify times when you might be offline (maybe you’re in deep work mode or taking a short break).

Set expectations about email or message response times. This prevents any assumptions or anxieties about delays in communication.

Key Takeaway: By establishing boundaries and setting clear expectations, you create a framework that allows you to be judged by your output, not just online hours.

10. Don't Take a No as Final

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If your boss isn’t ready to make the leap yet, don’t be disheartened. Ask for feedback, understand the concerns, and consider revisiting the idea in a few months. Remember, persistence pays.

Any transformative idea can face resistance initially. The key is to view setbacks as opportunities for refinement rather than absolute rejections.

  • Seek Feedback: If your proposal is met with hesitation or rejection, engage in a constructive dialogue. Ask for specific reasons and areas of concern.

  • Re-Evaluate and Adapt: Use the feedback to refine your proposal. Maybe there's a middle ground you hadn't considered, or perhaps there are certain reassurances you can provide.

  • Demonstrate Through Action: If your request is denied due to doubts about your ability to manage remote work, look for opportunities to prove yourself. Volunteering for projects that can be done remotely or showcasing productivity during occasional work-from-home days can build your case.

  • Revisit the Proposal: Circumstances and perspectives change. If your initial proposal isn't accepted, consider bringing it up again after a few months, especially if there are shifts in company culture or broader industry trends toward remote work.

Rejection can be tough, but resilience and adaptability are the hallmarks of successful remote workers. Use setbacks as learning opportunities and keep refining your approach.

11. Quantify Your Current Productivity

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Before popping the remote work question, spend a couple of weeks meticulously tracking your tasks, work hours, and achievements.

The goal? To quantify your current productivity levels.

Then, present these figures and posit how they could be improved or at least maintained in a remote work setting.

Then you can say: "In the past month, I completed 20 projects within office hours. Without the daily commute, I believe I can increase this number by 10% as that time can be channeled directly into my tasks."

12. Emphasize Employee Wellness & Satisfaction

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Discuss the proven benefits of remote work in enhancing employee well-being. Reduction in commute stress, flexibility, and a comfortable environment can lead to happier and more satisfied employees. And a happy employee is often a more productive one.

13. Highlight Cost Savings for the Company

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Demonstrate potential savings for the company. Fewer people in the office can translate to reduced costs in utilities, office supplies, and even real estate.

For Example: "If more employees are open to this idea, the company could significantly reduce overhead costs. It's a win-win situation where we're promoting productivity while being financially savvy."

14. The Global Time-Zone Advantage

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Try framing it to your boss as: The 24-Hour Productivity Cycle.

If you're considering moving (or traveling) to a different time zone, pitch it as an advantage. The company gets extended hours of productivity. You can start projects when the home office is closing for the day and vice versa.

For Example: "By working from Europe, I'll be starting my day when the US office is winding down, effectively extending our company’s productivity hours. This can be particularly advantageous for time-sensitive projects."

15. Immersive Learning for Better Performance

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Suggest to your employer that diversifying one's surroundings can enhance creativity and perspective – key assets for many job roles.

If you're in a creative role or a position that requires innovative thinking, immerse yourself in a new culture or environment to gain fresh insights and ideas.

Example: "I think that spending a few months in Japan, a hub for design and innovation, could provide me with invaluable insights that I can incorporate into our projects. It's about immersing oneself to bring fresh, global perspectives to our work."

Remember, the essence of each proposal is to highlight mutual benefits. While you enjoy the freedom and flexibility of remote work, ensure that your employer sees the tangible advantages for the company.

Now, Go Ask Your Boss if You Can Work Remotely

Asking to work remotely can seem intimidating, but with the right approach and a dose of persistence, it's entirely achievable.

The digital nomad in me knows the freedom and productivity that come from breaking the chains of a traditional office.

Remember, it's not just about how to ask but why you're asking.

Anchor yourself in your reasons, be prepared, and you might just be sending your next report from a beach cafe or a cozy cabin in the mountains.

Cheers to breaking boundaries and redefining where work gets done.

Safe travels and happy working!