How to Make the Case to Your Boss to Let You Work Remotely

Note from Sean: Lots of people work remotely now, and the numbers are only growing. Chances are, if you do most of your work on a computer, you can spend at least a day a week out of the office working from home. 

If you want to test out remote working, but don’t know how to approach the subject with your boss, well this post is for you. 

This week’s guest blogger is Kayla Matthews a productivity blogger based out of Pittsburgh, PA. Take it away, Kayla!

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Employment is changing before our eyes.

In previous generations, it wasn’t at all uncommon for folks to stick to one job, and one workplace, for their entire adult lives. Remarkably, technology has delivered us from this predictable cycle and created a manner of new opportunities to make money on our own schedules — often from our own homes.

How about you?

Do you spend 40 or 50 hours in an office each week? Are you beginning to suspect there’s a better way?

If you’ve been planning on asking your boss if you can switch to working remotely, keep some key things in mind before you sit down to discuss your intentions.

A Brief Overview

If you haven’t been directly touched by the work-at- home revolution, you will soon. With young people — also known as millennials — leading the way, telecommuting and full-blown self-employment are seeing big gains all across the country and the world.

People in the know are predicting that as much as 40% of America’s workforce could soon transition to self-employed or part-time status.

Why? Because people are asking for it.

The demand for remote working options continues to increase across the country. If you can believe it, the year 2014 saw remote work opportunities displace even healthcare as the most sought-after employment perk.

Folks everywhere are making it clear that they’re willing to forego “traditional” employee benefits and even larger paychecks if it means spending more time at home, or in the company of their loved ones.

Now, we’re not saying you need to jump on this high-speed bandwagon just yet — working remotely isn’t for everybody. But if you’ve been feeling for a while like you need to make a change, it can’t hurt to talk to your boss about working from home, at least part-time.

Make sure you know how to make your argument first. Here are some thoughts to get you started.

# 1. Have a Plan (And the Right Tools)

Probably the most important point to keep in mind is this: Don’t go off all half-cocked. It’s full-cocked or nothing.

Logistically, transitioning from an office environment to working remotely can be difficult, so you’re going to need to familiarize yourself with some of the available tools. You also need to demonstrate that you can still be held accountable for your work expectations and milestones.

To be more specific, think about your actual work environment — and we’re not talking a cushy desk chair and new window treatments for your home office.

How are you actually going to accomplish your work?

The answer will vary depending on the nature of your job, but if you do most of your work on your computer, you need to demonstrate your grasp of tools like VPNs — which allow you remote access to your company’s digital assets even if you’re not physically onsite — and collaboration tools like Trello, Basecamp, Slack, Google Hangouts, and dozens of others.

In some cases, your boss’s expectations might not need to change much. But in other scenarios, the two of you may need to hash out the details about how you’d track and submit your work, and whether you’ll still need to put in some face-time at the office for certain tasks, such as meetings or collaborative work.

Yes, there can be many moving parts. The point is that you need to know the full picture and have a plan to float to your employer before your meeting. It shows initiative and sets a good tone.

Let’s be honest: There’s still a mild stigma surrounding remote working — “If you can do it in pajamas, it’s not real work!” — but you’ll cultivate much good will if you demonstrate that you’ll take it seriously as a full-time commitment, even if you’re only working part-time hours.

2. Compromise on Job Perks (And Learn to Let Others Go)

Employment perks and what constitutes a “typical” career is changing fast. If you’re like many people, you might be willing to compromise on some of your employee benefits as you make the transition to working remotely.

Consider it a matter of fairness.

People who commute to an office each day should enjoy the perks that accompany such a commitment — whether it’s a larger paycheck, a more comprehensive health care plan or any of the other creative perks offered by forward-thinking employers, such as free wearables and wellness plans for recommitting to your personal health.

The point is this: If you want to free yourself from the commute and your 40 hours in the office, you need to cede some ground to make that happen. Negotiate. Find a happy medium for major employment benefits, such as healthcare.

For example, if you want to transition to a part-time work-from- home situation, your employer may not keep you on the company’s healthcare plan — for financial and perhaps legal reasons.

Instead, ask whether your employer could give you a modest stipend each month to put toward your own healthcare plan. Then, learn how to make up the difference with a premium tax credit.

It’s a compromise everybody should be able to live with.

3. Talk About How It Benefits the Company (Not Just Yourself)

Businesses exist to make money. There are many colorful ways to disguise the fact, but it’s the naked truth. As a result, you have to learn how to couch your argument in terms of how it benefits the company, in addition to how it might make your own life easier.

Remote workers are frequently more productive than their office-bound brothers and sisters. It’s a fact, so use it to your advantage. Use facts, statistics and emerging trends to state your case. Explain how cutting an hour-long, two-way commute from your daily schedule will make you less harried and more focused when you settle in for a day of telecommuting.

There’s also a real possibility that making the transition to working remotely could save your employer money, so think about that and make your case. If you’re using your own desk, chair, computer, toilet paper, water, coffee and so on, your employer can spend that much less versus having you in the office.

They might not sound like major expenses, but research shows that allowing employees to spend half their time working from home could save the average business around $11,000 every year.

Also, communicate to your boss is that if you’re allowed to complete your work on your own terms, you’re much more likely to stick around for the long-haul. The younger generations tend to rankle some feathers with their job-hopping tendencies, and hiring and training replacement employees can be wildly expensive.

Make sure your boss understands that you’re making this move not because you’re trying to escape from the company, but because you want to stay with the company — it might be the most important thing you say during the entire conversation.

4. Establish a System for Checking In (And Leave the Door Open)

Working from home isn’t about burning bridges. You might feel in your secret heart that there’s no returning to the office after you’ve had a taste of the pajama’d life, but it would be a mistake to start thinking in absolutes.

Express to your boss that you’re going to consider this a trial run until you’re both 100% comfortable with the system you’ve developed.

That is — if you have a system. You may have a boss who enjoys face-to- face meetings more than most, or who likes to check in on a regular basis, or who (gulp!) qualifies as a full-blown micromanager. If any are true about your boss, communicate that you’re not closing the door to regular communication and check-ins.

You should set some time aside to touch base and reevaluate how things are going — perhaps quarterly or more or less often, depending on the work you do. If you’re shedding your full-time status entirely, it’s unlikely that you’ll continue with the more formal types of employee reviews you might be used to, so propose an alternative.

You can exchange emails on a regular basis to compare notes. Staying in regular contact is vitally important if you want your employer to continue thinking of you as a legitimate, valuable and fully engaged employee.

The Ball’s in Your Court

The first move is yours. How liberating does that feel? Don’t think of the coming conversation as a sneak attack — consider it a thoughtful, strategic gambit, with benefits for both sides. Make sure you’re fully prepared.

More and more bosses will engage in similar conversations in the coming years, so make sure you’ve thought it through before making your move.

We’re living in complicated and exciting times, and most employers are proving they’re willing to roll with the punches when it comes to workplace flexibility and helping employees enjoy the most out of their careers.

There’s nothing wrong with wanting a change — you simply have to know how to ask for it.

Kayla Matthews is a productivity blogger and writer at WriterZone based out of Pittsburgh, PA. You can read her latest posts by following her on Twitter @KaylaEMatthews. 

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