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How to Convince Your Boss to Let You Work from Home — or Rome

The Day I Went to Work in Pajama Pants

I worked in HR for several years, and for all the upsides of working in an office, I definitely remember the downsides. I had days that I didn’t want to roll into my car at 7:00 am and drive to the office in winter morning darkness. I had days when a huge project was due by the end of the week and going into the office to finish the project was probably the least productive thing I could do.

I’m betting you’ve had days like that, too

So, what if, when you woke up 20 minutes late on a Monday (no judgments about what you were doing that Sunday night), you could just not go into the office and still get work done?

What if you got to make that choice?

Well, today I made a choice. I went to work in my pajamas… because I work from home. I’m going to show you how you can make that choice, too.

And to do that, you’ll have to overcome only one thing: talking to your boss.

But how can you convince your boss to let you work remotely — especially if your company doesn’t normally allow telecommuting?

Remote Working Is a Great Idea… for Both of Us

This conversation is first and foremost a negotiation. Your goal is to get an outcome that satisfies both of you, not just satisfies your needs.

So, to start this conversation, you’ll want to focus on 3 key things:

1. Remote work will benefit your manager (and company)

When going into any conversation where you’re asking for something, don’t talk about why it benefits you. It obviously benefits you — that’s why you’re asking for it. Instead, start with how this change will benefit your manager.

Think about what their struggles are as your manager.

How does your choice make their life easier? What will they gain if you work remotely?

Maybe you can:

2. Your performance is consistently awesome

If you’ve done past work with your boss, or even if you’re new and have results from a previous role to back yourself up, remind them of how great your work has been. (As a side note, if it hasn’t been great, you shouldn’t be asking to do this yet. Spend time becoming a top performer, and then negotiate.)

Remind them of these positive results so that you can show that you understand and can do the work, because you’ve done it before. Explain how you are more productive working from a separate area.

3. Remote worker productivity is better, and you have the research to prove it

There’s a lot of research out there that points to the positive impact of remote working. As much as your boss wants you to be happy, they care about results. So if you have research to support that you can continue to be productive while not at the office, it will help your case.

Ade Oolonoh has compiled a list of some great resources and benefits of working remotely:

How to Make Your Case for Working Remotely

Be clear and show your boss you understand their pain. What is your boss on the hook for higher up the management chain? Make it emotional by bringing up those challenges directly.

I’d really like to explore working remotely. I know you’ve been pressed to get projects finalized on even shorter deadlines.

Be the solution to the pain. You’ve just brought attention to one of your boss’s challenges at work — how can you be the solution to that challenge?

I’m able to get my work done quite a bit faster working from home, so I could turn in my projects to you even more quickly. And last year I exceeded all my set goals, so you know I get the work done.

Back up your claims with evidence. Without research (or at least a really good example from another company’s experience), your plan may seem poorly planned. Showing you cared enough to prove your point with research goes a long way.

I also did some research on remote work and found that employees are about 20% more effective when working remotely.

Set Goals That You Can Measure

To make sure your manager is on board with the idea, you need to minimize their risk.

Flip the roles and consider this from: wouldn’t you want some type of guarantee that your employee won’t just be playing with puppies and running around on a beach all day? (This was the most perfect day I could think of. Puppies and beaches)

This is also great for you. Setting goals that you can measure also gives you the benefit of doing results-based work instead of just measuring how many hours your butt is in the chair.

Here enters the famous S.M.A.R.T. goal: you want your goals to all be Specific, Measurable, Attainable, Realistic, and Timely.

This will do a great job of minimizing your manager’s risk by working with them to:

Identify the tasks in your job that can be measured

Every job has tasks that can be measured. Make a list of these tasks for your job. Measurable tasks include project deadlines, project milestones, sales numbers, conversion rates, customer calls, and so on.

Measurable tasks are anything that can be tracked.

Create measurable goals based on these tasks

Bring this list of measurable tasks with you to the conversation. Work with your manager to create goals based on these tasks.

For example, if you’re working on a website, you know the projected deadline for the site. Set up realistic milestones during the project where certain features of the site need to be completed.

Set a timeline to review your results

Make sure to set up times to review your results. If you’re going to work remotely, you still need to show that you are providing value. You do not want to be out of sight, out of mind.

This can be done by deciding on regular meetings to review your progress, or at the end of each project to review results and get feedback.

How to successfully set goals for remote work

Put your manager’s needs first. Show that you’re not trying to weasel out of work, but rather are trying to be more useful to the team.

Since I want to be sure that I’m doing a good job and producing the results you need,

Define your own preliminary tasks and goals. Don’t expect your boss to do it for you — giving someone extra chores will rarely make them excited to help you.

I’ve prepared a list of my measurable tasks and goals to go with them.

Collaborate and involve them in the finalization. Make sure you don’t present your proposal as final. You’re handing in a mostly-finished draft for polishing.

I’d like to work with you on finalizing the goals and setting up a reasonable timeline to review my progress so we are both comfortable with the transition.

Do a Remote Work Trial Period

Any change is usually met with some resistance. Even if there will be no negative impact, not having clarity on the change mentally wears people out. When people are tired they prefer to continue doing the same thing they’ve always done because it’s easy and familiar.

So make the change easy to understand. Make the change clear:

Set a remote work trial period with a start and end date

Before you go into the meeting, have a specific trial period in mind. Based on your experience at this job and with your boss, think about what would be a reasonable timeline and set a definitive remote work start and end date.

Three months is a good starting point if this is a new concept. It spans an entire business quarter and allows you enough time to get measurable results, work out any upfront issues, and allow everyone to adjust to the change.

Decide how and when you will work remotely

If transitioning from being in the office every day to not coming in at all for three months will be a shock, try easing into it. Instead, suggest working from home three days a week and coming into the office for two.

Also suggest that, if this works well for the first month and you meet all of your goals, that in the second month you will transition to fully remote.

Above all, be very specific about when you will be working remotely, and when you will be available or unavailable. Don’t leave room for ambiguity or uncertainty, this only feeds distrust.

Set up times to get feedback on your ongoing performance

As your setting up your schedule for remote work, also build in time to have a check-in with your boss specifically regarding the remote work.

This shows that you are concerned about their needs, and that you are serious about making this beneficial for both of you.

It’s also the perfect time to document the progress you’re making, so that it’s clear to both of you that you’re doing a great job.

How to make the transition to remote working

Make the transition simple, clear, and specific. Create a concrete, short-term plan to test the waters.

Since I know that this is a new work set up, I thought it would be best if we started it on a trial basis for three months. I can work three days a week out of office and two days a week in the office.

Assure your boss you will be available. Working remotely isn’t a reduction in responsibility — it’s an increase. Show your boss that you’re aware of this, and ready to take it on.

I’ll be 100% available and responsive to emails and calls during the hours we set, and we can have a weekly check in to make sure the trial period is going well.

**Get their cooperation and agreement to make this permanent.**Establish that this is a trial period to establish a longer-term working situation. Make the end game clear.

If I do a great job, I’d like to discuss working fully remotely after three months.

When to Talk About Working Remotely

There are good times to have a conversation, and also really bad times. For any of us that ever tried to convince our parents to let us go to a party on a Saturday night, you know this. Sometimes it’s best to keep your mouth shut until Mom has eaten dinner.

So when is a good time to talk about this to optimize your chances of success?

During your review

If you’ve been thinking about bringing up the issue of working remotely but haven’t done it yet, an annual review is a perfect time.

If your company doesn’t have a culture of doing this on a schedule, ask your boss if you can set up a time to review your goals and performance. Chances are they’ll be happy you’re taking initiative and you can use that time to talk about working outside the office.

At the end of a big project

If you’ve just completed a project and it went well, this is the perfect time to suggest a new work option. Your boss is excited because the team is doing well, and if you were part of the positive outcome, you can take advantage of your momentum to start the discussion.

During negotiations for a major job change

If you’re getting promoted or hired for a new job, this is a great time to bring up working remotely. These situations are both considered milestones in a career. Because of this, your boss (or new boss) will be expecting to have conversations about your work and salary. Since changes are already set to happen, capitalize on the mindset of your boss and ask now.

How to Say It:

I’m so glad we were able to meet. I know that we’re here to talk about my promotion, start date, annual review. After we go through that, I’d love to talk about working remotely. I’m extremely productive when working on my own and will be able to give you the results you’re looking for.

Where to Go from Here

The hardest part about working remotely is asking for it.

But by the end of the conversation you should have identified how this will help your manager, the metrics that you are responsible for and a review timeline, and the trial period start and end date.

I know that all the planning and conversation with your boss can be hard, but you won’t regret it when you’re finally setting your own hours, working from your couch, and finding time to live a life outside of your computer.

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