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I work for a small company in Toronto as a Software Developer. We are a development shop where I and two other developers spend our full work week on a single client which is based in New York city. The rest of the company (We total 8 staff, including the 3 working for the large client) deal with all of the small to medium sized jobs. Effectively, the three developers working on the large client have a lot of independence and enjoy many perks such as working from home and even travel. However, the owner of the company still expects us to be present in the office as often as we can.

Going forward, I would love to be able to work fully remote for this client, and do it through the company I currently work for. I have been here for 6-years now, always working on the same project for the same client and their revenue has grown from $50k a year to over $20-million this year.

My goal is to receive more remote work perks so I can do many small "travel vacations." I want to explore Canada and the rest of the world while still working on this project. As an introvert, how can I approach my direct manager (owner of the company) and ask to become a full-time remote staff member? Specifically, how could I word that question with respect to the following considerations:

  • It is a violation of my contract to work for the client directly
  • I already work 40+ hours a week for this dedicated remote client. I do not currently have any in-office responsibilities.
  • I still want to work from the office when I am in Toronto
  • This client and my boss have a direct familiar relationship (They grew up together), and are now in-laws

Thank you!

  • What timezone will you be able to work while you are traveling? I bet the expectation is that you will work Eastern time regardless of where you are – jcmack Dec 17 '19 at 0:23
  • Points 1 and 4 are irrelevant. Point 1: You're not asking to work for the client directly, I'm not sure why you would even mention that. Point 4: Your bosses personal relationship with the client is immaterial to you and irrelevant to your employment. As to points 2 and 3, why don't you just present them to your boss and ask? – joeqwerty Dec 17 '19 at 1:02
  • You should be very careful what "remote work" means. To you, it may mean travelling. To your boss, it may mean you're working 24/7/365. You need to set down expectations and not throw around buzzwords. – Nelson Dec 17 '19 at 2:27
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    To extend on the comment by @Nelson: Make sure that what you plan is actually covered in your contract. For homeoffice, for example, companies (in some countries) have to make sure that you have a proper working place at home, and the company insurance only covers you if you actually work there. So if you sign "homeoffice" in your contract but work all around the world, you might get in a lot of legal trouble (again, depending on country). – Dirk Dec 17 '19 at 7:32
  • Is there anyone within the company that has or had comparable freedom? – user180146 Dec 17 '19 at 14:12
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Summary: Have an open conversation about your goals/aspirations with your manager. Schedule it on the calendar so you cannot delay the conversation. Research the pros and cons of working remote and present your ideas as a proposal. Be open to changing your mind.

Long answer:

  • Have an open conversation about your goals/aspirations with your manager. Managers have to deal with different personalities all the time. Also people and their goals change. It would be great for him/her to hear your changing aspirations so they can work with you to support you. At the end of the day, it is important to realize that what is good for you is good for your manager. They cannot know what is not communicated to them. You might be pleasantly surprised. Even if they say no initially they may change their mind eventually.
  • Schedule it on the calendar so you cannot delay the conversation. Be intentional and get the conversation scheduled on the calendar. Title the event so the manager knows that you will be talking about it. The scheduled calendar invitation acts as an ice-breaker to have the 'tough' conversation. Side note, if you are truly considering 100% remote work, you will benefit from practicing intentionally around tough conversations. As a remote worker, it can be even more difficult to bring up tough stuff and if you are not careful/experienced it can easily eat you away over time. Working remote you have to be more intentional with tough conversations, view this as practice.

  • Research the pros and cons of working remote and present your ideas as a proposal. Try to find out as much as you can about actually doing this and make note of where your strengths and weaknesses fit into working remote. IMO, the best research is through doing it yourself. Maybe you ask to try it out while you are in Toronto, so that you and your manager can see how it all works. You will find the pros and cons of it yourself and showcase how you can manage your time effectively. I have worked remote for a few years now and personally find it difficult to travel while maintaining a full productivity. I would personally rather take vacations to travel. Consider the pros and cons in your discussion so that you can showcase your points in a thoughtful manner.

  • Be open to changing your mind. Lastly, the manager might say 'no' to you. That does not mean it is a 100% no nor does it mean it is a no forever. Having the conversation is just the start of getting to the goal. The manager will have a different perspective than you. If you get a no, or even yes, there will be concerns that you will have to address. Take note of those concerns and build up trust and experiences to address them. For example, if the concern is that you will not be able to be as productive remote, ask that maybe you try being remote a day or two a week and we can monitor those days if that affects productivity. Regardless of your manager's yes/no, you will have to keep an open mind and listen to his or her concerns.

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