How to Negotiate Asking to Work From Home (While Working Less and Getting Paid More)

How to Negotiate Asking to Work From Home (While Working Less and Getting Paid More)

Note: This article has proven highly useful to our audience in preparing to quit their job. If this article is relevant to you we highly recommend you also sign-up for our free webinar on launching a successful passion based business. It’s later this month and it’s free.Click here to sign up.

If you work for a company where systems and processes — filling out forms, creating reports and attending meetings — seem more important than actually doing the work, you likely wouldn’t believe you could negotiate an alternative work arrangement with your employer.

In fact, you probably have some major resistance to it, especially if something as simple as requesting a day off involves submitting a form six weeks in advance to human resources.

Here are some other common corporate assumptions:

  • Working from home is off limits or reserved for the privileged (although this study by Microsoft claims over 40% of companies actually have a work-from-home policy).
  • Face time matters more than results.
  • Negotiations only come during performance reviews.

The problem with all of these assumptions is that, for the most part, they’re completely untested. But the real question is this: Have you ever actually asked for what you want? And if so, did you come up with a strategic plan for doing so?

If not, then you’re living in an assumed reality.

When I was trapped in a demanding corporate job that, while interesting, didn’t challenge give me, I assumed that I couldn’t do anything about it, save for quitting my job and finding a new one. That was until I had the revelation that I didn’t have to follow the same template as everyone else. Just like all of my coworkers, I was assuming that all of these “unspoken” rules were set in stone.


I discovered how to negotiate a part-time, work-from-home arrangement with my employer, all while getting paid 15% more per hour than I had the year before.

And I’m going to show you exactly how I did it, giving you scripts that you can use to negotiate with your employer, no matter how much of a tight-ass they might be.

But before I get into how I created this arrangement, let me be completely upfront with you: I didn’t have any special circumstances that made me any more advantaged than anyone else.

Note: While this is an article about negotiating working from home and a raise, it can be applied to negotiating anything with an employer.

Here are some of the things I was up against:

  • I worked for a very large, very stiff non-profit company, which entailed a lot of red-tape and corporate BS.
  • Very few people in my organization worked from home.
  • The economic downturn of 2008 had just happened, and budgets were being cut left and right. It wasn’t exactly the best time to ask for more money and the ability to work from home.

Even with all of those odds stacked against me, I was still able to make my case for co-creating a more desirable work arrangement with my employer.

It all came down to what I did that no one else seemed willing to do: Ask.

As a society we’re trained that asking for what you want is selfish. But the truth is, it’s pretty dumb not to take the risk in asking, especially if it can benefit everyone involved.

If there’s one thing I had going for me it was drive (more like desperation, to be honest). I seriously wanted to reclaim my time and work on things that gave me joy.

But in order to really build momentum with my business, I needed the extra time by working at my job one day less a week. Because I was hungry to do whatever it took, I built up the courage to ask for what I wanted.

Overview of how I negotiated asking to work from home:

  1. I elicited the rule of reciprocity. Before I ever had the conversation with my boss and made the proposal, I made sure that I bent over backwards to create an abundance of value for my company and team.
  2. Procured a recommendation in advance. I knew it would be harder for my boss, the ultimate decision maker, to say no if I had received a recommendation beforehand from my direct supervisor.
  3. Prepped exhaustively for the meeting. I went through all possible scenarios and addressed all the objections I could think of before the actual meeting took place. Ramit Sethi describes this strategy as the Briefcase Technique.
  4. Held the meeting with confidence. I made sure I was in a positive and confident state before the meeting. Because all of the hard work had been done in advance, everything went smoothly.

Now, let’s get into the nitty-gritty.

Step 1: Timing and setting the stage

It’s important to know that I didn’t just engage in a random conversation and surprise my boss with the idea of an alternative work arrangement. That’s like popping the question to a girl on the first date. Probably not a good idea.

Instead, I made sure that the timing was right. I carefully waited to discuss what I wanted until the odds were stacked in my favor.

To do this, I wanted to make sure that I had deposited a surplus of social goodwill into my work relationships. The more I could leverage the rule of reciprocity (that all humans are naturally more likely to do something for you when you’ve done something for them first), the more I knew I could set myself up to win.

While you might not have a big project coming up as I did, you can still apply this principle by regularly going above and beyond for your employer. Take on new responsibilities, seek out new projects that will impact the bottom line, and most of all, find ways to do work that makes your boss look good.

In my case, I worked in a multimedia department and we just had a project handed down to us that was a significant undertaking. It involved photographing over seven hundred physicians in a two hundred mile radius within the span of two months. Not an easy feat, even when you have the resources that a $40 billion a year non-profit does.

I was tasked with project management and overseeing the organization and execution of the it. That meant ensuring all the photographers had the right information, scheduling all of the shoots and making sure that post-production went without a hitch. The biggest challenge was controlling the photography and lighting style from one shoot to the next when we had over a dozen photographers with varying lighting set ups, cameras and different ways of seeing things.

There was also having to deal with reshoots and corrupt memory disks. With all of this, the success or failure of the project rested on my shoulders.

Here’s a big takeaway: If you want to be seen as indispensable, make it your daily mission to make the lives of those you work with easier, especially those higher up than you.

I was working on my own business at the time and it could have been easy for me to give a half-hearted attempt at the undertaking. But I chose to see my day job as a springboard for the business I was creating, not something to be compartmentalized and shoved into a corner.

I went to extreme measures to deposit an abundance of value into the bank account of my work relationships before I ever requested anything.

Step 2: Recommendation in advance

The next step for me was to get a recommendation from my direct supervisor. While she wasn’t the one that made the final call, I knew that it would strengthen my case. My boss (the ultimate decision maker) trusted her judgment because she was closer to the daily operations of our team.

It wasn’t hard to ask her for it; she was already saying great things about me anyway. I regularly found ways to make her life easier and I knew she appreciated that.

Here’s what I said to my direct supervisor (names changed for confidentiality):

Hey, Margaret. As you know, I’ve really been working hard lately on this Physician’s Photo Project. I’ve been thinking about sitting down with Barbara [our boss] to negotiate some changes in my work arrangement, such as working from home. But before I do that, I’d love to have your blessing. It would mean a lot to me. Would you mind giving her a report on how I’ve been doing before I sit down with her?”

While it’s always a bit daunting to ask for a testimonial or referral, I’ve found that people generally appreciate the opportunity to say good things about you when you’ve done great things for them. Once you get the courage to ask, you’ll find it’s not as bad as you might think

Bringing in that letter to the official meeting with my boss went a long way to helping me get what I ultimately wanted.

“In war the victorious strategist only seeks battle after the victory has been won, whereas he who is destined to defeat first fights and afterwards looks for victory.” —Sun Tzu

Step 3: Prepping for the meeting

Before I had the official conversation with my boss I wanted to be able to clearly demonstrate how much time I had saved the company by working more efficiently.

Just as a seasoned general steps onto the battlefield confident in victory before he ever fights, I knew that I had to win first and then discuss the details with my boss.

A big part of that meant being prepared for any objections that might come up. Such as:

  • How are you going to get things done remotely?
  • How will you be able to work less and still get everything done?
  • What if this doesn’t work out?

I’ll get more detailed in my script below, but the key here is that I made sure that I was prepared for and rehearsed the conversation before it happened. I tried to emulate every possible scenario I could imagine and determine in advance how I would respond in each situation, much like you would prepare for a job interview.

I also made some key changes to my work and recurring tasks that I was prepared to present to my boss during the meeting. I optimized and streamlined many of the repetitive tasks associated with my job. I created checklists for bigger recurring projects. I batched much of the mundane work and implemented personal productivity practices that made me much more efficient.

One of the most effective techniques I implemented was the Pomodoro technique, which is essentially setting a timer for twenty minutes, working on a selected task, then taking a break for another five minutes. Not rocket science, but I’ve found the hardest part of getting things done is often indecision. Having a deadline is one of the best ways to force you to make a decision.

But one of the biggest changes I made was automating an extremely tedious and manual part of my job. It basically amounted to creating and sending certificates to recipients of our employee recognition program. I turned a once long, tiresome affair into a process 90% automated by a database and templates.

Step 4: Having the discussion

Now it was time to get down to business and have the “official” discussion. One of the key traps I wanted to avoid was letting the conversation become fear-based and defensive on the part of my boss. To combat this, I made sure that I made my boss feel heard and went to great lengths to address all of her concerns. This let her know I was taking this seriously and to preempt any potential fear or defensiveness that might come up.

Secondly, to remove all of the risk, I presented the idea as a trial run. We’d try it out for two weeks and we’d review afterward. If it wasn’t working, we’d go back to the old way of doing things. If it was working, we’d keep going and continue to check in to make sure things ran smoothly.

Finally, to avoid any sort of logical defense on her part (I knew I couldn’t win if it went to what the rule book said), I presented a strong moral case that appealed to my boss’s environmental awareness. Working from home was simply the right thing to do. It saved gas, cut down on traffic and pollution, and the overhead needed to keep the office powered constantly. It wasn’t just smart, it was ethical action as a responsible human being.

Here’s how the conversation went:

Me: Hey, Barbara. Do you have a minute?

Boss: Sure, what’s up?

Me: Margaret has probably mentioned to you by now that I’ve been really working hard to take our department’s work to the next level. And it’s got me thinking a lot about how I can be even more effective working from home and working less hours.

Boss: Okay, what do you mean?

Me: Well, I’ve been doing a lot of research and it’s ridiculous how inefficient we can be, especially when it comes to the time we spend commuting. I know how much of an environmental advocate you are and it’s just crazy how much energy and time we could save telecommuting. And let’s not even mention how we could impact traffic, which as you know, makes you want to kill yourself most days in LA.

Boss: That’s very true. So, where is this going?

Me: I’ll get to that in a second. But first I want to show you how I completely streamlined this repetitive part of my work that used to take forever. You know that certificate fulfillment process we used to have? I’ve completely automated it.

[I show her what I’ve done in detail.]

Boss: Wow, this is really awesome!

Me: I know, and it’s made me realize how much more I can do in less time. So what I’ve been thinking is that I can start working from home one day a week, and cut one day back entirely (three days a week in the office, one day a week at home). It would save you guys a lot of money, and it would make my life way easier. Also, I know that I’ve been working a lot of overtime lately on our big project and haven’t been compensated for that, which I’m happy to do. But I’ve also been with the team for over a year and haven’t received a raise. So I’m thinking with the amount of time I’ll be saving us — working one less day a week — a 15% increase in my pay sounds pretty reasonable. To make it fair to you guys, and to make everyone comfortable, we could do it on a trial basis, say, for 14 days, and then evaluate. If it’s not working, we can go back to the old format. If it is working, we can just keep checking in to make sure everything is going smoothly. How does that sound to you?

Boss: Well, Jonathan, you obviously spent a lot of time preparing for this and thinking this through. It sounds reasonable, but I do have some concerns. What if we need you to work more than four days some weeks, are you going to be okay with that?

Me: Yeah, that’s definitely doable. If a big project comes up and I need to spend some more time working on it, I’m happy to do it. But I’d still like to be able to do it from home if possible.

Boss: Okay, and what if we need to show you something in the office? Do you have a plan for this?

Me: Well, I can definitely always stop by. But there’s always Dropbox or screen-sharing via Skype. We can rely on those on days when I’m not in the office.

Boss: Okay, I think we can try that, but I’d still like for you to be able to come in sometimes, and I also want to track your work performance. If you’re not able to get the same amount of work done, then this isn’t going to work.

Me: I’m confident that with the changes I’ve made it won’t be a problem. The best thing about this is that since it’s a trial, we can always go back to the old way if things don’t work out.

Boss: Okay, that sounds good. Let’s give it a shot.

Crafting your own alternative work negotiation

While you may not use the exact same strategy as me, and may not want the same type of work arrangement that I did, I’m sure you can apply some of the strategies here.

Now, what type of work arrangement would you like to negotiate? It’s important to be clear on what you want before you devise your plan.

Granted, this takes work, but if you do all of these things you move the odds from their favor (just you trying to get something) to your favor.

But please, don’t forget that the most important thing is that you ask. Simply start asking for what you want more. You’ll be surprised at how often you’ll get it.

Want to take it a step further to actually quit your job and work for yourself?

This is probably the most in depth article in existence on negotiating with your employer, and I hope that it helps you tremendously. However, you might want to take it further than that and actually quit your job altogether to venture out on your own.

If that’s the case, check out this case study I made on how to quit your job. It’s the most raw, honest and embarrassingly honest video I’ve ever made. I figured you’d benefit more from the WHOLE truth, rather than part of it.

Secondly, if you want to make a serious investment in working for yourself, check out Trailblazer.

It’s a premium course that gives you one mission every single day for the 365 days. Each mission is designed to build your business, create momentum, and keep you focused on only what matters.

Click here to learn more about it.

Finally, what’s your favorite tip for negotiating? Please share in the comments below!

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The Psychological Price of Entrepreneurship and being a Digital Nomad (from Someone with Anxiety and Depression) | Light Way Of ThinkingHow To Start Traveling The World | Elena's TravelgramjonathanNo Balance Between Work and Life? Why It Doesn’t MatterConvince Your Boss to Let You Work from Home with a … – Lifehacker – WORK AT HOME Recent comment authors
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Jonathan, Terrific article. I totally agree that setting the stage is extremely important. Another way of thinking about that part, is consider the situation as a bank account. You’ve got to build up deposits (delivering on big results) before you can make any big withdrawals (like negotiating a work at home arrangement).




Quite an interesting article Jonathan, and with some great suggestions. Except that not everyone works in an office. Shop assistants, factory workers, those in warehouse jobs, couriers, mechanics, taxi drivers, cleaners, gardeners, and those in most other non-office based jobs would have no way of doing their job from home. Myself, I never worked in an office. When I quit my job back in 2006, I was working in a warehouse. My supervisor called me aside one day and told me that his superiors in the office had noticed that I’d clocked in a couple of minutes late on a… Read more »


Absolutely, there are a lot of jobs where this can’t work. I’m specifically speaking to people who work in positions where work can be done remotely when it comes to negotiating to work from home.

However, this same strategy can also be applied to negotiating a raise or anything else with your employer.


Great article Jonathan. And great analogy from Ben.


Glad you enjoyed it Ben.


As always, your posts are delivered so thoroughly and thoughtfully!
Hopefully in time, more employers will recognize the benefits of allowing this level of flexibility.

Well done Jonathan.


I hope so too. Thanks Teresa.


This is great! And impeccable timing! I seriously was just strategizing how to ask my boss if I can go part time. I’m thinking I’m going to just go for it tomorrow! This post has definitely given me some things to think about. Thanks Jonathan!


That’s great. Make sure to leave a comment and let us know how it works out for you. :)

Paige | Simple Mindfulness

As you’ve said, it’s amazing what you get if you simply ask for it. I’ve deposited into the goodwill jar for my boss lately by negotiating some huge savings from vendors simply by asking. I’m also working hard on a variety of projects to create some big efficiencies in the operations and better reporting. I completely agree that building up the goodwill is essential. Even though I just started my job last month, I had to be home with my kids one day. I didn’t want to take the day off so I casually stopped into my boss’ office and… Read more »


Glad you enjoyed it Paige. Definitely let me know how it works for you.


Great article Jonathan– I always appreciate the reminder to see my job as a springboard for what I truly want to be doing, because when I compartmentalize that’s when the quality of my work declines, and that spills over to all areas of work, including what I love. This is very timely as I’m about to turn down a full time job offer I previously expressed interest in, and I want to continue working in a part-time capacity and keep a good relationship with my boss and our team!


PS… I did it- keeping the part time job, but only the parts I like and getting rid of some of the stuff that was super boring, and I got a 25% pay increase. Thanks for the confidence booster!


Congratulations Kate! That’s fantastic news!

R.C. Thornton

Great insight Jonathan.
Many people get frazzled thinking about “how in the world am I going to be able to pull this off??”, “this” being working from home, quitting their job and starting their own business, etc. But you show that the real value comes from meticulous planning and prepared execution. That takes the risk out of the situation and increases the propensity for success.


You’re right RC. When it comes down to it almost anything can be done when you put in enough planning, effort and preparation.


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[…] How to Negotiate Asking to Work from Home (While Working Less and Getting Paid More) | Paid to Exist […]


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hi jonathan, this is jonathan, cool name btw :> I came across your article because I’m in a similar situation however its not because of commute but it does have to do with work efficiency. I work in the architecture field, office job, commute isn’t too bad. however the office has been good about accommodating me for my certain ticks that may have bothered others near my desk…its embarrassing to say this but its true and I’ve gone to doctors, was prescribed meds, nothing really worked for me yet. I am starting meditation now, trying to calm my mind. I… Read more »


[…] My idea was to leave the office and ask to work remotel. Luckily, the tech beauty of modern world allows it to do for most of us.  Just for a few months I said, originally. But I was clear to everyone I won’t get back to the cubical. If you’d like to negotiate remote work arrangement, I highly suggest reading this post. […]


[…] strategies and scripts you can use in Four Hour Work Week and you can also check out this article here. Make sure you learn about how to beat procrastination when you work from […]

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