Once you feel you’ve almost managed to convince your boss, he might need an extra push to be convinced that there is no risk to the company or him.

To put his mind at rest, suggest that you be allowed to do it on a trial basis for anywhere between 2 weeks to a month and let him reassess you once the trial period is over.

If at the end of the trial you don’t meet performance standards, then he has the right to revoke your teleworking rights.

At this stage, you are putting all the pressure on yourself to perform and any failure of the teleworking agreement will be your own.

If you boss accepts this, pack your stuff and head on home.

Welcome back! If you liked this post, feel free to post a comment below with your thoughts or register your name and email to stay in touch for special announcements and free gifts:

Name:

Email:

We respect your email privacy

Here is a list of some of the things you should have before approaching your boss:

1. Proof of increased productivity You need to show your boss that it makes more sense to telework than it does to work in the office. One of the strongest reasons you can give is an increase in productivity outside of the office.

   How you will collect this evidence is completely up to you, however I would recommend using progress reports with dates of when you might have been working away from the office.

2. Proof of teleworking ability

   This will be shown in progress reports that show sustained or improved productivity while you are reportedly away from the office. You may also point out situations or problems that you managed to handle successfully (and quickly) while working remotely.

3. Clear reasons why productivity is increased away from the office

   On reporting improved productivity, you also need to state why you were more productive. Reasons can include being at home where you are more relaxed, have more space to work, good lighting and perhaps an additional monitor or two to work. These are all good reasons for recognizing improved productivity.

   If you have a boss who is so unreasonable that he insists that you are making it up, I would recommend doing more research to find actual scientific statistics showing how all the reasons you have given indicate that they actually do improve productivity in workers.

   At this stage, it is also important to state your personal reasons if you have any. These reasons may include feeling happier with the flexible time and feeling more relaxed. If you have already been noted as a good employee then expressing personal fulfillment will be taken seriously by your boss.

4. Any other reasons you can think of

•  Saving time on commute, not having to spend an hour or more each day traveling back and forth from office which allows you to work more
• More time to spend with family and kids, especially if you have a spouse who also works
• Improved cost savings on petrol and car maintenance in the long run
• Reduced risk of getting into a car accident (if you drive long distance)
• Reduced costs on company for floor space and electricity
• Reduction of carbon footprint for both you and the company by using less power and travelling less

Most bosses fear the same thing with teleworkers, and that is a deterioration of communication and ability to manage. If this is a fear your boss has, explain to them how you overcame these issues during your trials. Also state that in emergencies, you may come into the office and also state how in the past, emergencies rarely occur and that you have developed remote solutions to deal with most difficult situations when they occur.

Sometimes the best way to lead into a conversation is with a question. Instead of asking for the opportunity to telework, try asking if the company has any existing policies on teleworking.

This allows you to get a better overview of the teleworking situation in your company and allows you to adjust your arguments accordingly.

If you feel that your boss will instantly jump the gun and say there is no way in hell you’ll be allowed to telework at all, ask him to hear you out. At this stage, you need to be prepared to either quit or get fired.

A point of note, employers (in most countries) cannot fire you without a good reason.

They especially cannot fire you if you are trying to propose ideas that allow you to improve the productivity of the company.

If the boss sees through your plan, and is only bent on refusing you simply to make you unhappy, you have 2 options:

1. Quit
2. Take your case to a higher authority in your company who will see your point and recognizes that your boss is being illogical and unreasonable

Some of you might be thinking that you dare not do anything to make your boss look bad by going over their head. The truth is this can be a real possibility if they choose to be unreasonable.

At times like this, you will need to reassess your reasons for wanting out of the office, and ask yourself what you are willing to do in order to achieve that goal.

Remember, everything you would have worked on up to now is to prevent yourself from getting fired or having to quit, even if you make requests that require your boss or superiors to go out on a limb a little bit.

You are a commando, not a foot soldier. You are a specialist with special training and skills that gets the job done, has the wage that is the same or slightly higher than the average foot soldier and is not easily replaced.

“I disapprove of what you say, but I defend to the death your right to say it.”

~Voltaire

Before asking for a full time teleworking agreement, make sure that you have covered the following bases:

1. You have shown slightly above average productivity in house and are considered an effective employee
2. You have a high perceived value to your company
3. You have come up with remote solutions to all items that could call you back to the office
4. You have shown increased productivity while working remotely and have evidence to back it up

If you are able to tick off all of the above items, you can consider yourself ready to request a remote working arrangement.

If you are generally afraid of your boss, let us redefine the word “Boss” so that you can see a boss for what they truly are:

Boss = A person who is getting paid more than you but is trapped in the office. A person who is highly stressed because they needs to manage multiple things and keep an eye on the activities of the people under their charge. A person who usually has less of a life than you do because they spend much more time working and worrying even when out of the office. A person who is so caught up with work and is so far gone in their career that they cannot even imagine other possibilities outside of the workplace.

Now that you have identified the animal that is your boss, you see that there is nothing glamorous about being a boss other than the fact that they are getting paid more. Money is great, but if you have to trade time and peace of mind to achieve it, it does lose its value.

Also, do not trick yourself into thinking that they get more respect because of their position. If the only reason you strive for a high position in a company is get respect, you are obviously a person who needs to spend some time on self reflection and learn to respect yourself despite your position or financial condition.

Moving on…

So now you know what your boss truly is. Hopefully by following the advice in the previous section on assertiveness, this has helped you reduce your fear. If not, then just imagine your boss naked when you go in to see them.

Before you approach them though, you are going to need a good list of reasons that will compel them to think that letting you work remotely is a good idea. Below is a list of reasons that I was prepared to use (some of which I did use) when I requested a teleworking agreement:

1. I’ll be able to save time commuting back and forth from work
2. I do most of my primary communication via email and phone
3. I’ll still be doing the same amount of work in the week, and you will know my progress as I will report to you every following Monday with completed work
4. I will come in to work every Monday and when needed. These include meetings, training, and information gathering that I can usually deal with when I come in on Monday to report on work progress and also prepare for the coming week.
5. I will be able to attend self paid training that is only available during the day and still complete my work tasks later in the day during non-office hours. This allows the company to save money on furniture and equipment for me, save space that can be utilized for other employees, reduce running costs of electricity
6. If ever there is an emergency that requires my physical presence or if there is an occasion where I need to be physically present for the job to be done, I can easily come into the office
7. I have better equipment at home, a desktop PC and Laptop fully loaded with appropriate software, High speed internet connection and a dedicated work space that I used for other work projects and my own printer for drafts.
8. I have a more comfortable environment with ample lighting that allows me to work longer without getting headaches or tired from staring at the screen for long periods of time
9. I am less than an hour away in terms of physical availability and can be reached readily anywhere by phone and email.
10. The flexibility makes me happier and I am able to exercise and lead a healthier lifestyle with no loss in productivity to the company
11. My remote rights may be revoked at any time if I you feel I am dropping in productivity as a result of working away from the office
12. I am available to come back in whenever a project that requires my physical presence needs to be done.
13. Working remotely, I have added pressure to complete my work tasks to retain my remote working rights which will lead to consistent and predictable productivity. I will also learn to be more efficient and communicate effectively as a result of being limited to email and phone.
14. I am not distracted by office noise and this allows me to work with more focus and efficiency leading to better output per week.

Now, don’t take this list word for word and use it on your boss. This is just an example of what I used applied to my situation at work. You may be able to use some of the reasons above. Otherwise, you will need to compile your own list of reasons.

There are 3 important principles that you will need to remember when creating this list and they are:

1. The reasons must all be logical Reasons that are based on your feelings or that have no foundation in the productivity of the business can be easily refuted by a boss who is determined to not let you work remotely
2. The reasons must bring more benefit to the company than you
   
   It has to be clear on multiple levels that by working remotely you will be bringing more benefits to the company and not creating more problems.

   Alternatively, the reasons that you give could bring no additional benefit to the company but also no additional disadvantages either. This approach will usually work if a remote working policy already exists within your company.

   Your working remotely could cause some problems for the company, however if presented with the prospect of having you quit if you are refused, this may be enough to let you work remotely. This approach will only work if you have a high perceived value within the company making it more disadvantageous to have you quit rather than let you work remotely.

3. The reasons must reassure your boss that there is no risk in letting you work remotely You can reduce risk for your boss by assuring them that you will always be reachable and can come into the office if you are ever needed in an emergency. This is important initially when you begin teleworking to reassure your boss that you are still available physically if needed.

Over time, supposing you manage to refrain from going back to the office often for whatever reason, your boss will eventually get comfortable with the idea of you working away permanently.

Suggesting a trial run in the initial stages will also allow you to show your boss that you are capable of working remotely and also allow him the option of changing their mind if they feel like it isn’t working out

Giving them the complete freedom to revoke your remote working rights if your productivity drops will make your boss feel like they have complete control over your position and make them more willing to work remotely

Keeping these 3 principles in mind, write your list of reasons for why you should be allowed to work remotely. If you are still having trouble at this point, try writing reasons that your boss would give to disallow you from working remotely and refute them.

This is probably the easier way to go, however it is also important to add benefits that your boss would not necessarily think of to your list of reasons.

Exercise 5.1: What to prepare before asking for permission

Exercise 5.2: Finding good reasons to work remotely