How to negotiate a work from home arrangement that works

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Just like everything else these days, employment looks much different than it did even ten years ago. The explosion of the gig economy, for example, has changed the work landscape significantly. No longer just the purview of dog walkers and babysitters, the American gig economy is estimated to include 15.5 million people, and those are just the ones who rely on gig work for their primary income.

Another big change? Remote workers. It is estimated that more than 40% of Americans do at least some of their job remotely. Rapid advances in technology have paved the way for remote work and not surprisingly, lots of people are eager to partake. Why not? The benefits are obvious. You could save time and money, escape office distractions and enjoy the luxury of working in your pajamas.

If you’ve fantasized about working from home all (or a significant portion) of the time, and you’ve got the type of job that can be accomplished from a distance, the main obstacle is convincing your boss to let you give remote working a whirl.

First things first. Let’s do a quick reality check.

Is working from home right for me?

Go in with your eyes open on this one.

Working from home isn’t for everyone. To be successful with this set-up, put yourself through a quick personality trait test. An effective work from home employee simply has to have the following tools:

  • Time management skills
  • Ability to stay focused on task despite the many distractions of your own home
  • Strong work ethic. You know the old phrase, “dance like nobody’s watching? Well, if you work from home you have to be able to work like everybody’s watching.
  • Ability to solve your own problems. While you’re not completely on your own, you will find that some problems will have to be solved independently when you can’t just lean your chair back and ask your cubemate a question.
  • Ability to stay motivated and efficient in the absence of daily in-person social interaction.

Do some soul-searching and be honest with yourself. It takes a certain type of person to work from home effectively. If the thing you look forward to the most is the opportunity to take plenty of naps, you might be setting yourself up for failure.

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How do I get my boss to let me work from home?

It is very unlikely that your employer will come to you with an offer to work from home. If you are interested in making the switch, you will have to be proactive.

What does that look like? Be prepared to:

  • Determine whether your employer has any employees already working from home. If you’re the first, you may have to work harder for permission.
  • Draft a work from home agreement
  • Schedule a sit-down with your boss
  • Explain to your employer what benefit he/she will get by letting you work from home

Steps to pitch a work from home agreement to your boss

The devil is in the details, and crafting a work from home agreement is no exception. Keep in mind that your employer might see this as a truly radical idea, particularly if you will be the first one in your workplace to go this route. How do you get past that? By putting in the time to cover all your bases before walking into your boss’s office to have the talk.

Show, don’t tell

Remind your employer how much value you bring to the organization. If you’re not adding value to begin with, your employer has no incentive to go out of its way to grant an alternative arrangement to you.

For employees who are valued and on the way to becoming indispensable, it is much easier to make the case that you are worthy of the employer taking a chance on a work from home arrangement.

Mention specific accomplishments, value, and quantifiable achievements.

What’s in it for your boss?

We know what’s in it for you. Flexibility, more time with family, freedom from commuting, and so on. While that’s all nice for you, none of these benefits provides any incentive to the employer.

Your organization has a mission to accomplish. That mission does not include fulfilling your personal wants. Don’t include those in your discussion with your boss or your written work from home agreement.

Instead, highlight the benefits of your arrangement from the employer’s perspective. Will you be more efficient in this way? How? Will you be able to service clients in different time zones with this arrangement? Describe the plan. What other pluses can the employer expect if you work from home?

Always remember your audience and in this case, it is your employer.

Prepare for employer skepticism and objections

The best way to have a successful meeting is to predict questions. Rather than looking like a surprised deer caught in headlights, preparing the answers ahead of time helps you become a smooth, persuasive, and effective change proponent.

While every employment situation is different, here are some common objections you might hear. Be prepared to respond to them. Practicing in front of the mirror wouldn’t hurt.

  • If I let you do it, everyone will want to do it.
  • How will I know you’re being productive?
  • We’ve never done this before.
  • Are you going to ask us to buy you new equipment?
  • How will you stay involved with the team?
  • What about privacy and security concerns stemming from working at home?
  • Are we going to be able to reach you when we need you?
  • What will our customers think?

Be specific

A proposal to work from home cannot afford to be wishy-washy. Your proposal and agreement need to be specific.

Think through all aspects of your arrangement and include them in your proposal. This will not only make you look ultra-prepared, but will also help you identify potential objections your employer might have, allowing you to address those head-on.

  • When will you work from home? All of the time or some of the time?
  • What hours will you be available?
  • What office equipment will you need at home?
  • Is your home-based Internet sufficient?
  • Will you attend specific, regularly-scheduled team meetings in person?
  • When will the arrangement begin?
  • Will there be any compensation changes?

Final tips for crafting a solid work from home agreement

The way Americans work is changing. If you think working from home is right for you, there is no better time to propose your own arrangement.

Prepare in advance. This isn’t a topic for an add-on “BTW….” in an email. Prepare like your new work life depends on it, because it does.

Be flexible. The arrangement you end up may not be exactly what you were hoping for. Whether it’s a trial period, less than 100% remote work, or some other variation from your ideal set-up, you’re on your way to the work world you envision for yourself.

Good luck!


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Rachel Parisi is a freelance writer and attorney. She focuses her writing on insurance, financial services, and employee benefits. In her previous life, she served in the United States Air Force as a missile combat crew commander (think ‘Wargames’). Opinions are her own.

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