The Productive Remote Work Guide (Part 1) – How to negotiate for it, crush it, and get noticed.

By Paul Milano

I’ve worked from home for over 3 years now and it has been the most successful and productive stretch of my career.

I’m sure you’ve heard the term digital nomad used. This is becoming increasingly more popular, as more and more people are working remotely — part-time, if not full-time.

Still, many employers feel nervous at the prospect of letting their staff work from home independently. This is understandable as people feel if you can’t see someone how will you know they are doing anything? As we will discover though this is completely not true and a silly way to measure someones performance.

That’s why we’ve put together this two part guide for you who’s interested in working remotely. This is your all in one guide to negotiate how to get it, how to do incredibly well once you’ve gotten it and how to make sure you stay in the spotlight so you’re not forgotten come promotion time.

In Part 1 we will cover:

  • Why working from home is a no brainer
  • Debunking the myths to create a strong case to your manager
  • How to negotiate and get a remote work setup

In Part 2 we will cover:

  • How to make working from home the most productive time of your career
  • How to get noticed, get promoted and communicate so it feels like you are still there
  • Common downsides of working from home and how to overcome them

Why work remotely?

There are many benefits of working remotely, namely far more flexibility in your life. But there are also other benefits, such as time and money saved on not having to commute.

Before we get into how to get remote work and thrive at, let’s quickly make sure you understand the benefits.

1. Own your schedule

Remote working enables you to customize your schedule to fit your individual needs. That means you can go to the gym, pick up the kids, and buy groceries when it’s most convenient. I’ve seen so many people who don’t go to the gym or skip other personal tasks because they’re too tired after their commute. Remote work really helps you own your schedule more.

It has to be said, of course, that your job still requires you to meet certain deadlines and get things done. A flexible schedule doesn’t mean these deadlines become null and void.

Working remotely means you’ll be measured on the work you do, rather than the time you spend sitting at a desk. I think we all know someone who shows up to work in their cubicle everyday but isn’t actually doing that much? Remote work ultimately rewards actual productivity (getting things done) vs the optics of just sitting at a desk from 9 to 5. A good way to increase your productivity at home is to employ task batching.

2. You’ll get more done

Contrary to popular belief, remote working actually increases your productivity. Don’t take our word for it — the claim is backed by science. A two-year Stanford study showed that remote working resulted in shorter breaks, fewer sick days, and less time off.

However, in order to maintain productivity at home, it’s important that you have a solid framework in place — we’ll get to that later in this article.

3. No commuting

Another (perhaps obvious) benefit of remote working is that you won’t have to commute. That’s a big win, even if you live in big cities with lots of public transport connections.

Londoners, for example, spend an average of 48 minutes per day on commuting to and from work. Similarly, the average U.S. employee spends 52 minutes on commuting every day.

That time could be spent on work, which is exactly what most remote workers do. Almost everyone I know who works from home ends up starting early and working later. So be sure to mention that to your boss when you negotiate your remote working schedule (which we will tell you how to do shortly).

4. Fewer expenses

Commuting can be expensive, and working remotely takes that expense out of the equation. Employees can also save money by not having to buy expensive coffees and lunches.

But it’s not just employees that benefit financially. Companies can also save money since their employees will take less time off, aren’t late to work, and are generally more productive.

The biggest expense of all that can save money is corporate real estate. Companies that employ remote workers can save money by scaling down their offices, or make extra money by renting their extra space out to other companies.

5. You’ll be healthier and happier

The above advantages also result in an extra benefit that workers with flexible hours have over others: healthier and happier lives.

Research from the University of Minnesota has found evidence to suggest that flexible work hours result in better sleep, higher energy, less stress, and improved work-life balance.

This is a kind of a no brainer. Everyone wants more flexibility in their lives instead of being forced to show up at a specific desk each day. People feel far more in control of their lives and much less stressed.

This sounds great, how do I start?

If you’ve been stuck in traffic on your way to the office one too many times, then the thought of working remotely may have crossed your mind.

The benefits to you are crystal clear: no more commutes, flexible working hours, and fewer expenses. The problem is that your employer might not see how that benefits them.

Most people who start any type of remote work can’t go back afterward.

So how do you go about negotiating a remote working arrangement successfully?

How to Negotiate a Remote Work Setup

Step 1: Debunking the myths:

The main reason companies are reluctant to let their staff work from home is simply down to a lack of trust. But why hire someone in the first place if you don’t trust them? Great employees will work hard no matter where they are.

Many employers have bought into certain myths surrounding remote working, and are basing their decisions to not let their employees work from home on assumptions or old school mentalities.

In order to negotiate successfully, let’s see if we can debunk some of these remote working myths.

1. The productivity myth

The first myth is that employees aren’t productive when they work from home. That myth has been thoroughly debunked by scientific studies (see benefit #2 above).

Even regardless of the science, someone coming to the office and physically sitting in their desk is obviously no metric of productivity. All of us have had that one colleague who showed up to the office everyday but spent most of their time on Facebook rather than doing real work.

We need to change the mindset here that productive work can only be done in the office.

In fact, office work can lead to less productivity, as we’ll see below.

2. The distraction myth

Many bosses think that remote working leads to or encourages distractions. However, a study shows that office workers spend an average of 15 minutes making coffee, 12 minutes on the toilet, and over two hours surfing online.

And that’s just the things they distract themselves with. Anyone who’s worked in an office will know that colleagues will walk by to chat about Game of Thrones, last night’s big game, ask you to do something for them, or complain about their commute or any other random thing going on in their life.

All of those distractions interrupt your workflow, and are very costly in terms of time.

Personally, my days in office are generally my least productive days because of this. It is very hard to go 30 minutes without someone coming by to ask you something.

3. The in-person myth

Finally, many bosses worry that their staff meetings will suffer when employees work from home. They fear the lack of face time will lead to a disconnect.

Let me ask you this though, think of your last meetings you had. How many people were in person vs how many people called in?

Almost every company I’ve seen now will have offices in other countries, other cities or have contractors or employees working from some remote location.  This means someone will always attend via phone or Skype anyway.

From my experience, if even a couple people need to attend a meeting virtually, it is generally better to have everyone attend virtually.

Most meetings in the modern world are digital now anyway.

In Part 2 of this post, we will discuss actions you can take to thoroughly blast past these myths.

For now – it is important to be aware of them as these are the most common objections.

Step 2: The Negotiation:

1. Be a superstar employee

Since lack of trust seems to be an issue for many managers and arguably the biggest barrier to remote work, you should do your best to build as much trust between you and your boss as possible.

The best way to do that is to simply be a superstar employee and deliver on your promises. Even better is to over-deliver — just don’t over-promise.

This needs to happen before you even ask to start working remotely. It’s a no brainer that if your boss does not trust you there is little chance that they will allow you to start working remotely.

Stick to your deadlines, manage expectations, and simply crush it every day you step into the office to shatter any possible doubt about your work ethics.

You can go the extra mile by doing the following:

  • Take an interest in the company and its goals
  • Come up with ideas to help grow the business or save costs
  • Take initiative to execute some of these ideas yourself
  • Present the results of your ideas (if they’re positive!)
  • Grow your relationships with people in the other departments

The list above may seem intimidating, but it really isn’t. Even the smallest ideas that can help improve some process or save money or just be a better way to do things can go a long way and make you stand out. Finding these little side projects can really boost your own energy and enthusiasm too.

2. Evaluate your own performance

Hopefully, your boss will have noticed that you’ve made an extra effort to be a superstar employee. Now is the time to review and evaluate your own performance.

Ask yourself the following questions before you propose a remote working arrangement:

  • Have you consistently delivered high quality work?
  • Can you continue producing the same results remotely?
  • Could you become even more productive if you worked remotely?
  • Can you measure your productivity in a tangible way?
  • Do you know all the facts and data in favor of remote work?
  • Will your boss react positively if you propose a remote work agreement now?

If you can answer yes to all of the above, then you’re ready to start negotiating for a remote working arrangement. However, it’s a good idea to start small — see below.

3. Propose a trial period

You’ve now been crushing it in the office for a while and everyone knows about it. But it’s still a big ask to go from being in the office full-time to not being there at all.

The best and most effective way I’ve seen to start is to propose a trial period for a part-time remote working agreement. You’re now only asking to work remotely one or two days per week, and only for a fixed period of time. I would recommend 3 months.

After the trial period, you and your boss can review how it went. If they feel like it didn’t work as well as expected, then you simply return to your normal working arrangement.

The reason this is a great approach is two-fold. Your boss doesn’t have to take a big risk, and you also don’t bite more off than you can chew in terms of your workload.

VERY IMPORTANT: If the trial gets approved and you start, make your days working from home the most productive days of your entire week. Really crush it on those days in this trial period.

In Part 2 we will discuss how to go about doing this, but for now just know that doing this will really remove any possible barriers to continuing it full time.

4. Get feedback and make it permanent

It should go without saying that you need to continue performing well during your trial period. Make sure you track your results so you’re well-prepared for the trial period review.

Don’t wait until the end though, ask your manager how it is going throughout.

Although you may think you’ve done exceedingly well, it’s not a guarantee that your boss will see it the same way. Ask for their feedback and listen to it carefully.

Try to identify any potential pain points your boss may have. Address all their concerns and emphasize how the company will benefit from your remote working arrangement.

Your proposal for a remote working arrangement should do the following:

  • Outline how you consistently have added value
  • Reference the results of the trial period
  • Emphasise how the company would benefit
  • Address any potential issues with remote work
  • Get your point across in a clear and professional manner

Most importantly, your proposal needs to sell the idea. That means you should not make it about yourself, but about the company instead.

Most likely at the end of all of this, switching to a permanent work from home arrangement will be fairly easy. You can also choose to expand on the 1-2 days from home and make it 3-4 if you want, using the same strategies.

Some managers are old school though and stuck in their ways. Even if you have crushed it, they may want you in the office still everyday. In this case, if a flexible work arrangement is important to you, it’s best to look elsewhere and go work for someone or a company who supports it.

I have come across managers like this and sadly they end up losing their best performers due to their own trust issues and inability to adapt. It’s their loss in the end.

Here are a few resources to look for full time remote jobs. If you do land one of these, part 2 of this guide will teach you how to really crush it while working from home (or coffee shop of your choice).


I’ve seen the steps above and have personally used them a number of times. It’s highly effective.

The next key piece of this all is once you are in a remote work setup, how to keep crushing it and keep advancing your career. Working remotely can make you less visible, but it doesn’t have too.

Read Part 2 to find out how to make this the most productive time of your career.

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