Here are easy ways to set yourself up for success by preparing a little in advance, and having the right answers to your boss’ questions.
1. Figure out how the company will benefit.
Sure, you may really enjoy skipping a long commute and working in your jammies, but how does that help the people who write the checks? Perhaps you’ll be saving them money in parking reimbursements they dole out each month. Maybe you’ll be able to conduct business with clients near your home more easily, or finally have the extra time to fit in an evening business class close by now that you’re not commuting an extra hour. Be sure you’ve given thought about the possibilities before you walk into your boss’ office with the request in hand.
2. Compile your own good deeds.
Essentially, you’re asking for a big favor from work, and favors go to closers. You should have a clean record in the office (not too many strange sick or vacation days, successful track record with projects, no need for extreme supervision, etc.). If you can’t be trusted to get the job done when your boss is looming over your shoulder, there will be less confidence that you can get ‘er done when you’re miles away by yourself. Just like when you get ready to ask for a raise, prepare to sing your own praises when you’re going in to ask for remote work.
3. Pick your moment carefully.
Nobody likes to have the rug pulled out from under them, especially your boss. Lay the groundwork with your supervisor by scheduling your conversation (instead of, say, suddenly asking them one afternoon by their desk) so that you can show you’re serious, and not looking for a way to play hooky. Make sure there’s an upside for your group or company, so that it doesn’t appear like you’re leaving your coworkers in the lurch. Maybe it’s a slow time of year without lots of meetings or on-the-fly collaborations, but you have a lot of work you could focus on better from the solitude of your at-home office — great! Maybe the company has had a terrible quarter, and everyone’s secretly shopping around for a new gig — not a great time to ask for unsupervised days home.
4. Ask for small favors (and be thankful for what you get).
Instead of jumping feet-first into 100 percent time working remotely, ask for a small trial run, like a morning every other week, or a few full days a month. Maybe your employer needs convincing that you can deliver, and that’s OK! Not all workplaces are set up to deal with remote workers, so the best course of action might be a few tests before you move forward into something that might be a little more extreme. Don’t grumble about the baby steps — they’re your stepping stone to more autonomy, after all.
5. Brace yourself for a “No,” then move beyond it.
Sometimes the answer is in fact, “Nope.” But here’s what you can do. If your boss isn’t convinced you’re ready, you can actually set yourself up for some informal “trial runs,” say, when the weather turns south or the landlord is coming to clear that clog. You can offer to work from home so you keep the productivity running smoothly. Once you prove you can actually do it, you’ll have some real-life success stories to use when you go back and ask for long-term remote permission. If your boss’ no is really absolute, and you’re dead set on remote working in your future, the best thing you can do is find yourself a new gig that’s already fully remote (maybe try one of these top employers for remote jobs).
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