How to Convince Your Boss to Let You Work Remotely

Drake Southwell
10 min readJan 16, 2018

Let me guess: you’ve been dreaming of working from a hammock under blue skies, but you don’t know how to broach the topic with your superiors. Guess what? Many brave souls have been there in the past, and have succeeded in transitioning to a career where work is based around life and not the other way around.

Location-independent work opportunities are popping up every day, and more people than ever want to join the growing number of remote workers and digital nomads. Last year alone was a massive year for remote work and digital nomadism. According to a 2017 analysis from Global Workplace Analytics, forty percent more U.S. employers offered flexible workplace options than they did in 2010. But location-independent work is not restricted to Tech — many professions can make the transition to a remote status.

As more and more working people discover the freedom and flexibility a remote work lifestyle has to offer, it is unlikely that this trend will slow down.

So, how do you get started? Here are five steps you need to take to start living your new digital nomad life:

Step 1: If you aren’t a top-performing employee yet, become one.

“Hard work beats talent when talent doesn’t work hard.” — Tim Notke

Are you executing your job well in the office today?

If not, convincing a traditional boss to let you work remotely will be an uphill battle. If your boss can’t confidently say that you execute consistently in the office, you are simply not ready for remote work.

Start upping your performance in the office and make significant changes to the way you approach your work. Don’t be afraid to go the extra mile:

  • Come up with creative new ideas to grow the business. Example: If the business doesn’t have a social media strategy, outline one. Experiment with effective software and systems, report successful results.
  • Learn how to grow the business outside of your formal role. Network with other departments, cultivate an interest in your colleagues’ work, and learn how they execute. Example: If you’re a marketer, be aware of what software development is up to.
  • Take a genuine interest in the company and its success — learn about your company’s story and what it actually does. Grow passionate about how your company contributes to society.
  • Build rapport with your higher-ups as you create more value — nurture a positive, professional relationship with your employer, but never flatter. Let your work speak for itself.

As Cal Newport would say, make yourself so good they can’t ignore you. You will have taken the first step towards workplace freedom.

Step 2: Evaluate where you are and what you want

“Know who you are. Know what you want. Know what you deserve. And don’t settle for less.” — Tony Gaskins

Now that you’re so good they can’t ignore you, you’ve become a commanding force in the business. You are driving real results and inspiring your co-workers to do the same.

By implementing the strategies in step 1, you’ve become a top performer and an integral part of keeping the business running smoothly and sustaining its growth.

Hopefully, you’ve built enough rapport to have some significant leverage within the organization: leverage you can put towards negotiating a remote work agreement.

But only you know your boss. Ideally, your boss has taken notice of your increased motivation and drive within your role. But maybe your boss is not paying attention to your tangibly higher results and you need to consider a career switch.

Evaluate your current situation by asking yourself honest questions:

  • Have I demonstrated to my boss that I can create measurable value here?
  • Do I have data and facts to back my claim of high workplace productivity?
  • How would my boss react if I told him I want to work remotely right now?
  • Can my role even be done effectively while working remotely?
  • From where would it be most feasible, economical and effective to work remotely?
  • Would my productivity continue to stay the same or grow with remote work?
  • Is there a tangible way to measure this?

Asking these questions will make Step 3 a smoother, more thought-out process.

Step 3: Propose a remote work test trial

“We don’t know who we are until we see what we can do.” — Martha Grimes

It’s important to test your limits before jumping straight into what you want.

If you want to bench 300 pounds at the gym, it’s best you work your way up to 200 first. So when proposing remote work to your boss, you are better off proposing a week or month long trial period at first.

The trial period will allow you and your boss to see if remote work is feasible within the organization. Agree to this trial and make sure to schedule a meeting after the trial (this step can be integrated with step 5). In this trial, you must prove that you can meet or exceed the expectations of a remote workplace.

Remember, the focus is not solely on your personal freedom, but rather on meeting or exceeding your value creation abilities at work in a remote format. If you can do this, remote work is a feasible option for you.

Step 4: Get feedback after the test trial

“We all need people who will give us feedback. That’s how we improve.” — Bill Gates

Your trial is over. You’ve done a ton of extra work to the best of your ability. Now it’s time to meet with your boss and discuss the future of your remote status.

Remember, value is subjective. Just because you think you succeeded during the trial period, your boss may not feel the same. If this turns out to be the case, listen to your boss’s feedback on your performance.

Make sure to listen to any pain points or disconnects regarding work expectations. Addressing your boss’s concerns could benefit you in the long run, and allow you another chance to prove your capability. Depending on how much remote work means to you, you might consider proposing cuts to your salary or benefits to work remotely.

It’s up to you. But come to terms with the fact that your organization just might not be compatible with the lifestyle you have in mind. If this bothers you, consider adjusting your career accordingly.

Learn new skills. Become a freelancer. Sell your services to one or many other companies that have no issues with remote work.

The barrier to entry is lower than you think.

Step 5: Craft a long-term remote work proposition

“When asking for something, appeal to people’s self-interest, never to their mercy or gratitude” — Robert Greene

Assuming your trial went well and your boss is thoroughly impressed with your remote performance — ideal scenario — now it’s time to lock in your future.

You have proven yourself as a value creator, and now it is time to leverage that social capital.

When crafting your formal remote work proposition, the most important thing is to reduce or eliminate any costs your boss might incur from your switch to remote work.

Take this anonymous sample:

I have been employed at the University for 8 years and am very committed to the quality of my work. Lately, I have been finding it increasingly difficult to address some family issues due to my full-time work schedule. In addition, I have a commute time of 45 minutes from Monroe. My ability to balance work and family needs would be greatly enhanced by reducing my hours to 80% time. I believe that I will be more effective and focused when I am at work, and my family would benefit from the additional day I could spend at home addressing their needs.

This is a formal request for a reduction in my work schedule from 100% to 80% time. I propose a work schedule of Monday — Thursday (or any 4 agreed upon work days) from 8:00am — 5:00pm. This schedule would help me balance my work and family responsibilities more effectively.

The following represent possible issues as well as solutions due to my reduction in time:

Systems Coordination & Training:

Issue: Departmental response to questions regarding REX and POTS might be delayed.

Solution: All departments would be informed of my work schedule and I would keep Corporate Time updated to support communication of my schedule. I would train Donna to act as my backup if an emergency issue were to come up, and I am willing to be contacted by cell phone in the case of any emergency. The web page can also be used as a source of information and support for the campus community. A project I am currently working towards is incorporating a training program on the Purchasing web page. With this web page training in place, onsite training would only be necessary in dire circumstances.

Financial Reporting and Analysis:

Issue: Last minute reports would require a backup preparer.

Solution: Most financial reporting and analysis issues have timelines already in place (e.g. budgeting, online personnel transactions, office purchasing, reconciliations), and I will continue to organize my time to support these deadlines. I already have the templates needed for such projects, and a back up preparer could be trained to support such issues if they were to arise on one of my days off. If these solutions are not sufficient, I have the ability and am willing to access my work computer from home for emergency circumstances.

Management & Supervision:

Issue: Office equipment in need of service or repair.

Solution: If office equipment should need service attention, procedures are already in place for Donna to contact the service vendor.

Supervision Issues: Who will supervise Donna on this one day per week?

Supervision Solution: As Department Manager, Randy would supervise Donna for this one day per week. When Donna has a preplanned day off, I am willing to adjust my schedule to support the need for at least one of us in the office at all times.

Other Issues: Assisting the Senior Buyer with last minute bid analyses.

Other Solution: Oscar might have to do his own complex bid analyses or administrative functions if they were needed on my day off. Alternatively, this would enable the Buyer and/or Donna to utilize recent training in software programs such as Excel, and stimulate growth in other programs used to support these administrative functions.

With effective communication and some additional pre-planning methods, my proposed 80% work schedule may benefit the department. The budgetary savings may allow Purchasing the opportunity to hire a student employee to support other areas of the department (e.g. Equipment Management). Also, this student could function, at times, as the front office receptionist, allowing Donna the opportunity to cross-train in other areas of the department.

I am willing to work with Randy and my colleagues to negotiate a schedule that will best fit the department’s needs. I would like to suggest a “trial period” of 60 days. After the initial 60 days, I believe we should meet and discuss the pros and cons of the schedule to determine if departmental needs are being met.

I appreciate your consideration of this request, and would be more than happy to meet with you in person to discuss this in further detail. I look forward to hearing from you.


Jane Doe

Notice how in the proposal, the employee:

  • Clearly outlined the ways she would add value
  • Specifically addressed potential issues with working remotely
  • Communicated professionally and with high-quality
  • Referenced the trial in the initial proposal (optional)
  • Noted the benefits to the company, not just to herself

In short, you must think not about how remote work helps you, but instead how remote work will help the company. That means taking an initiative that you might not feel obligated to take as a traditional worker:

  • Is there any paperwork I can assist my boss with involving my location switch?
  • Can I make extra efforts to maintain workplace cohesion with my co-workers?
  • How can I make communication with my boss smooth and efficient?

Ask about these considerations in your proposal, and in any subsequent talks with your employer. Mitigating these issues will make the agreement best for all parties.


“It’s up to you!” — Marcus Aurelius, Meditations

Despite the fact that many traditional 9–5 jobs can be restrictive, it’s very possible to adapt your traditional job to your needs. Jobs are more flexible than we like to think.

Work is an exchange of value. If you create a ton of value with your work, traditional barriers and constraints can be overlooked and even dismissed, and you can get what you want.

So if you want to work remotely, make it happen through your own hard work. Don’t wait until you’re working remotely to get your priorities straight and work hard.

Do it now!