8 steps to propose working remotely to your boss

by Wendy Soon on September 24, 2013

Distributed teamsWe’ve been talking so much about working from home, working remotely, being part of a distributed team. What about those who are still working in traditional offices, but WANT to work remotely? What should you do? What steps do you need to take before you can also be part of this bunch of happy folks working remotely? It seems like a daunting and almost impossible task to request to work remotely. Here, I have broken the process down to 8, bite-sized steps so you can comfortably work towards your dream life of working remotely.


  1. Imagine yourself working remotely. If you had an accident that made you immobile for four weeks as you recovered (touch wood), how would you work remotely from home for those four weeks? You need to first convince yourself that this is possible, before you can convince anyone else that you can do it. Think about how you would go about in such a situation, what tools you will need, and how you will communicate with the rest of your team.

  2. Pretend you are the boss. Before you move along, put yourself in your boss’s shoes too. What would he think of you working remotely? How would he react? Would he be indifferent, approving, or worried? Can he trust you to work outside of the office? If the answer is negative, then stop, and work on it. What is it that he is against? Why would he resist remote work? Find the root of the problem, and attack it.

  3. Practice working remotely. Start small. Take 2 hours a week, and work from a cafe near your workplace. Start small and start near, so that whenever your boss calls for you, you can immediately get back to the office and have a face to face meeting. (This is important, because your boss should, at this point of time, have no idea about what you’re attempting, and thus you need to still be available at all times) The key is to get used to it, and to be comfortable with it. This is like a ‘test trial’ for yourself, to know that you will enjoy working outside of your office, and to prove to yourself that you can get things done independently of the environment you are in.

  4. Quantify your productivity. Find a way to measure your own work productivity. Tasks completed; number of customers acquired; sales generated; lines of code written; revenue earned. Document it. Even office workers need to know how to quantify their productivity, so they can use it for promotions. However, this is especially important for someone hoping to work remotely, because that is going to be the proof that you can work remotely, and would also be the ongoing measure of you maintaining your productivity when you successfully get approval to work remotely.

  5. Create opportunity to work remotely. Now that you know you can work remotely, and you can measure your productivity, create that opportunity to prove it to your boss. It could be just half a day or a day that you need to be away from the office, but show that the time away does not affect your productivity at all. Use the method in step 4 to quantify your productivity while being away, and show your boss that you did well regardless of where you were physically.

  6. Practice facing rejection. Proposing remote work to your boss may not be easy, especially if it is something completely new to him or the company (or both). There is a high chance that the reply will be a straight ‘no’ the first time you try, so you need to know how to respond. One rejection doesn’t mean everything. Learn how to question the decision, learn how to receive rejection, and learn how to bounce back for a second proposal. Practice this at every opportunity you have — propose absurd things to your friends. Then try it with people less close. Negotiate prices at flea markets. Request for upgrades and special treatment wherever you go. The tougher the situations you put yourself into, the better you will be at the art of proposal.

  7. Propose to your boss working remotely for just one day a week. Now that you are ready to propose and negotiate with your boss, go for it! Start small, start infrequent. Ask to work remotely half to one day a week. Be strategic. Choose a time that is least busy, and has the highest chance of him agreeing. (and use Margaret Neale’s tips to negotiation — see video below)

  8. Extend each successful trial period. As you successfully work remotely, and prove to your boss that it doesn’t affect your productivity, slowly extend that to 2 days. 3 days. 2 week stretches. And finally, you’re working remotely full time!! 🙂

Don September 27, 2013 at 10:14 pm

Great post, I love the negotiation video which says that thinking of negotiation as a problem solving

Wendy Soon September 28, 2013 at 5:43 am

Thanks! Negotiation is truly a tough skill to develop. Maggie is a very good lecturer. Check out our other posts reflecting on her teachings:



Raj Lal September 28, 2013 at 5:59 am

yes the negotiation video can change the way you think

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