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Working remotely is as good as it sounds.

No commute, no office drama, few interruptions, freedom of space and ability to work from anywhere are game-changing benefits. For many, working remotely is used as the foundation in cultivating a well rounded work-life balance. It is one of the best ways to start the process of lifestyle design.

I’ve successfully negotiated working remotely five different times in my career and I know the steps you can use to achieve the same success. I’ve negotiated working remotely both 1-2 days a week and also 100% full-time which allowed me the freedom to move across the country.

It’s probably not as hard as you think. More and more companies are adding working remotely into their HR policies and even more are making remote-work exceptions for those employees who make a valid case for it.

Before diving into the how, I need to first put the nay-sayers to rest (thoughts that I had to overcome initially).

There are hundreds of excuses that your mind will use to deny the possibility of working remotely, many of which will appear to be 100% logical reasons.  However, as with anything in life that is worthwhile, these benefits are reserved for those who can be both creative and push past their initial fears and doubts.

Working Remotely Excuses“My job cannot be done remotely.”

This is the most common argument and hardest to conceptually overcome. However, the majority of white-collar jobs today can in-fact be done remotely. It helps to run through a thought experiment. Imagine you had some pressing family issues and had to relocate across the country for three months. How will you make it work with your current job? What job responsibilities 100% require you to be physically present?  Is it possible to transfer those duties to someone else on site under your remote supervision.

This was an eye-opening exercise for me when I was a fully integrated director at a Company. When I boiled it down the only task that 100% required me to be there was to physically sign checks.  Every other part of my complex role could, in theory, be done remotely including attending meetings and staff management. One caveat is there are some traditional jobs that do not jive with working remotely, namely nurse, teacher, construction manager, etc. But don’t stop your thinking there. Each of these roles mentioned have creative solutions for working remotely- remote case manager for nurses, online professorship for teachers, and remote project manager in construction, etc. Check out indeed.com, type in your current job, and in the “where” put remote. You’ll be surprised at what’s out there.

“My boss will never go for this.”

This may be true if you just walked up to your boss and proclaimed “I’m going to be working remotely 100% from now on – sound good?”. You will find that after reading the step-by-step guide below that this is approached much more intelligently. The goal is to make it a win-win for you and the company since you will demonstrate greater efficiency and ability to deliver more when working remotely. Also, the proposal that you deliver to your boss can be non-committal and contains a series of “test runs” that will allow your boss the insight to make the right call.

“Now is not the right time.”

Our minds are really creative and will craft a compelling story as to why now is a bad time to embark on this journey- I’m newer at my job, there has been a recent change, I just got a new boss, I’m going to get fired, etc. First off, I can tell you from experience- there is never a right time. Secondly, you are the only one that is perceiving the timing and situation this way. Your boss and everyone else in your company have their unique list of priorities and views that are not the same as yours. What you perceive as bad timing may be good timing for your boss, so discounting an opportunity on the basis of bad timing is illogical.

Working Remotely GuideStep 1 – Define your role

First, what type of remote arrangement do you want?  Do you want to be able to work from home one to two days a week or do you want to be working remotely full time? This will help frame the rest of the steps in this process.

Next, write down all the tasks that your job requires. Next to each task write whether it can be performed remotely or if it requires that you are in-person to complete.

Next, follow this simple diagram to see the thought-process behind making remote work possible:

Working Remotely Diagram


Nowadays, very few tasks require that we be physically present: this includes meetings, training, presentations, etc. Most office applications are on the cloud and meetings can be held on skype or google hangout.  I challenge you to be creative and figure out solutions for how to make in-person tasks remote-able. For remaining non-remote-able-tasks (awesome compound word), see if they can be accomplished the days you are in the office or see if a coworker could take them on.

Step 2 – Redefine your role

In the event you can’t make all your tasks remote-able or transfer them to coworkers, this process may require that you redefine your role. There is a right way to do this. First, peruse over your list of job tasks and pick out the ones that are:

  1. the most valuable to your company. It is likely that 20% of the tasks that you deliver on contribute to 80% of the value derived from your position. This takes some honest reflection but is a very helpful exercise. A good starting point is- what in your role contributes to sales or customer retention directly or indirectly?
  2. of most interest and preference to you. Identify the tasks that bring you the most pleasure and keep you the most engaged.

With any luck the above few tasks can be done remotely or re-framed in a way that they can. The goal will be to rewrite your role to encompass only these smaller set of tasks and placing more time and effort into them. You will need to demonstrate to management that the best use of your time and to maximize your value to the company, will be to work solely on these tasks, remotely.

Step 3Draft your remote plan

Using the insights from above, draft a list of the tasks you will complete remotely and what technology solutions and methods you will use for doing so. In example: Task 1- Oversee team process on projects- I will schedule two Google Hangouts each day, at 9am and 3pm, and invite all team members. The team will be required to submit their status on the project, prior to the meetings, on our shared Google Doc. Task 2 Etc.

Step 4Trial Run

Plan to work from home for 1-2 days in the coming week. You will need a valid reason so either “schedule” a plumber, get your car fixed, drive someone to airport, call out sick, etc. You will need this opportunity to work remotely as your case-study and support when vying for a remote work arrangement with your boss later.

On the day(s) you work remotely- make sure you absolutely crush your work, and then some. Its important that you jot down some measurable accomplishments (e.i. I completed all my days work in 4 hours and made meaningful progress on these long-term projects).

Step 5The Pitch

Now the fun part. Schedule time with your boss to talk about your role in the company. During the conversation these are your main objectives:

  1. You were working remotely the other day because of x, and you couldn’t believe how much more work you accomplished. Cite very specific accomplishments.
  2. Without the commute and interruptions, you were able to devote more hours to work then you ever could do at the office. Cite actual hours.
  3. You are wondering if, for a trial period of one month, your boss would allow you to work remotely (1,2,5) days a week. You know you will accomplish so much more for the company and it would make you significantly happier. You will make sure to be overly-communicative and provide updates throughout.
  4. Reinforce that it is a trial and that your boss can pull it at anytime. At the end of the trial you can both decide if the arrangement makes sense to continue.

The trial is a great way to keep the power in your boss’s court and really highlights that you want to do what’s best for the company. A helpful tactic, commonly used in sales, is to end the proposal with something like – “does that sound reasonable to you?”. Of course it sounds reasonable so its hard to say no to that.

Step 6Hustle Time

During your trial remote days, make sure you are contributing at least 50% more than you are contributing during your in-office days. Keep detailed logs of what your completing on which days and make sure to be 100% available and over-communicative with your team/boss. Over the next month your goal is to build the case such that your boss would be out of his/her mind to not continue this remote arrangement.

Step 7– Enjoy working remotely!

Not surprisingly, very few employees ever attempt to negotiate remote work. It requires creativity, a lot of effort and going-against-the-grain. And don’t worry. Employers value employees that go after what they want and who speak up, especially when it’s in the best interests of the company.

Working remotely isn’t for everyone, but for me, it was an amazing alternative to commuting to the office each day. I’ve gotten hours back in my life each day and am able to accomplish more at work, with less stress.

If you go after it- congrats and good luck! Feel free to share your experiences or leave a question in the comments below.

All the best,