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I'm working in the United States for a small company. It is not unlikely that, several months from now, it will be beneficial for me, for family reasons, to move to another city. I wish to broach the topic of telecommuting (working remotely) with my employer. (I don't do anything that technically requires me to be in the office, but of course my employer prefers people to be in the office for accountability, camaraderie, morale, easy consultation, or whatever reasons it has. Currently, no one works remotely full-time (although people do so occasionally).) I would like to broach the topic with my employer now, so that I know whether I'm able to move. (If my employer refuses to allow me to telecommute, then the cost of moving will outweigh the benefit, and I will not move.) I can think of a couple of ways to broach this topic:

  1. Be honest. "It's likely that it will be somewhat beneficial for me to move, etc. Can I work remotely?" The downside of admitting the likelihood of my wish to move is that, if my employer refuses my request, it may start to view me as a quitting risk, and begin to seek a replacement (or partial replacement(s) for various aspects of my job), eventually firing me or at least not promoting me.

    Another downside is that, by specifying that I want to move and not that I absolutely must, I'm giving them less incentive to grant my request (assuming they want to keep me).

  2. "There's a slim possibility that I'll absolutely need to move, etc. Can I work remotely?" The first downside from #1 exists here and may even be more likely since I'm saying the move may be necessary (or may be less since I'm saying the probability is slim). The second downside from #1 is gone.
  3. "It's likely I'll absolutely need to move." The first downside from #1 exists here and is even stronger. The second downside from #1 is gone.
  4. "There's a slim possibility that it will be somewhat beneficial for me to move, etc. Can I work remotely?" This has the first downside from #1, though weaker. It also has the second downside from #1, stronger. Plus, it sounds rather wishy-washy.

There may of course be other options. (And other up-/downsides to the existing options.) What do you suggest?

If it's relevant, the person I would ask would probably be the CEO. That is not whom I report to most regularly, but he is aware in a general sense of much of what I'm doing. (Like I said, it's a small company.)


I see the answers to "How should I bring up working from home?", but they are more general (not about someone with a specific reason to move cities) and about a limited-telecommuting case (working part-time remotely, not full-time).

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Well the first thing is that before I asked something like this, I would make sure that my performance is really strong. To be a pioneer in something like this, you have to be someone whose work they implicitly trust and definitely want to keep.

I personally would not worry about being viewed as a a short-termer if they they turn you down unless you know the CEO is a vindictive type. If you are good performer, those are harder to replace, so there is no real incentive for them do so.

Timing may be critical, so first you may want to do a little of that part-time telecommunting and show you can be trusted to telecommute and then wait until you have done something that has them particularly happy that you work there. If it happens while you are telecommunting, so much the better.

Then be honest about whatever family issue is going to make you want to move. Be honest about if it is a temporary situation (like a dying parent) or a permanent one like your girl friend getting a new job in another city. Tell them that you aren't sure yet if this will be necessary but might need to be able to handle this personal issue by moving if it became necessary and ask if they would consider letting you telecommute if you had to move. Tell them that you would prefer to stay with the company if at all possible. Tell them why you like the company. Remind them that you have occasionally telecommuted and not had a problem with keeping up your work. Then see what the CEO says.

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Small offices are less likely to want you to do this than bigger ones I would think. There are the obvious reasons why it's better to have staff on site.

I would go with honesty, but that's just a personal quirk I have. The downsides with that are as you stated, plus it's much less likely you would get promoted anyway if you worked remotely. And it's more likely that others might be given some of your tasks, leading you to eventually become unneeded. So whether or not the boss grants you permission you still run the same risks.

I'd weigh very carefully how beneficial the move will be, and if I did move, I would be a quitting risk, because I'd much prefer a local job, even if working remotely I'd prefer to be at a local company. You may differ, but you don't really know until you're away in a new environment.

One thing I have noticed about remote workers since I employ some. Is it's much easier for me to fire them, they mean much less to me as human beings. Again that may just be a personal thing.

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    It is also much harder, as a remote worker, to visibly "exceed fequirements", or to fing out about snd get involved in the most exciting work. See other answers on that topic befote concluding that wkrking remotely is actually a good choice for you. I've been doing it for a decade, and thete are definitely trade-offs. – keshlam Feb 29 '16 at 22:14
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Honesty is the best policy, but you also have to frame it in a way that it will be beneficial for the company to allow you to telecommute.

First, you have to prove that you can do it. Just because someone is a good employee doesn't mean they will be a good remote worker. Start by asking them to test out remote "days," ie. every Wednesday you should work from home to work out all the kinks in the system. Find out what software you need, which contacts you need to have, etc. Right now I use a software called Hubstaff that allows my clients to see my time reports (I'm paid hourly), randomized screenshots, activity levels and more. It's all about transparency--even more so when you go remote (counter-intuitively).

Then, let your company know how they will benefit from this. For example, if your office is running out of space, let them know that by working from home you'll be taking up less of their in-office resources. You will provide your own computer, lighting, Internet connection (make sure it's secure), and other equipment.

You mention that your boss prefers people to be in-office for camaraderie, but point out that often all the office interruptions hinder performance/productivity. If you're getting interrupted multiple times a day, you are less likely to go in-depth into your tasks. Jason Fried from Basecamp gives a great TED talk about it, and he said one option is to make your communication passive--ie. emails, IMs (messages you can get to in your own time).

Hope this helps, I've been freelancing for 3 years now with 5 long-term clients, so I'm happy to answer any questions you have.

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Try something like this... if it is relevant.

Boss, I would like to telework for a week, maybe next month, so that I can spend some time with my brother with a new baby / sister getting married/divorced / aging parents, grandparents.

This is a little trial for both of you. See if they go for it. See if it works for you. As a bonus, you'll get to spend time with family.

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