3 Tips for Convincing Your Boss to Embrace Flex Work

As the prospect of securing remote work has increased dramatically over the past decade, this topic has been tossed around a time or two. Is it really possible to persuade your boss to switch things up and embrace flex work, enabling you to work from home (or a coworking space or coffee shop) some or even all of the time?

In a word, yes. You wouldn’t be the first to accomplish it, nor the last. If you’re employed in an onsite job but dreaming of better work-life balance, read on.

Maybe you’re a seasoned remote worker whose role clearly requires some office time but could also be accomplished virtually, or perhaps you’re seeing an opportunity in your current role to embrace a more flexible arrangement. How do you convince your boss that this is a good idea?

Here are three tips for convincing your boss to embrace flex work:

1. Tailor your initial pitch.

The most effective approach begins by understanding your audience. Start by putting yourself in your supervisor’s shoes. Would she be concerned about productivity or punctuality? Would he worry you’d be unresponsive or that tasks would fall through the cracks? Make a list of possible questions, and formulate thoughtful, detailed answers. When talking about advantages, keep your boss’s priorities in mind.

Unless this person is a passionate environmentalist, it likely won’t matter that a few work-from-home days reduce your carbon footprint. But perhaps the concept of reduced overhead would be music to their ears.

Bottom line: if you don’t know your boss well enough to know which angles would make the most convincing argument, you’re probably approaching this conversation too soon.

2. Be specific about your plans.

This conversation should not be a meandering brainstorming session. You should arrive having done your homework on the most salient points of your proposed flexible arrangement. Discuss in exact terms what the timeframe could look like, and have a rationale for suggesting it. (If it enables you to pick up your kids from school twice a week, great; you can also highlight the fact that you’d be able to do very focused heads-down work even earlier on those days since there’s no commute.)

Communicate that you’re prepared to leverage the latest technologies to ensure you’d still be working closely with your superior and your team.

Remember: proximity is only as important as your level of engagement. If you can demonstrate that you’re just as productive and responsive from home as you would be at a desk, your boss should have little reason to disapprove.

3. Leave it open for reevaluation.

Probably the easiest way to scare off a remote work-shy superior would be to demand a permanent new arrangement. If what you’re asking for has never been done before at your company, consider this to be a major shift.

Even if it has been previously approved, you’ll want to understand how those arrangements have worked out—and know that if things turned out poorly, it could influence a decision for you. So open this request in the same spirit that you’re seeking to work—flexibly—and make it known that you’re willing to try this out as an experiment of sorts.

If you’re confident enough in your own ability to make flextime or a fully remote role work, then passing a trial period shouldn’t be an issue. You’ve got to test this out, too. Agreeing to reconsider this option buys you time to get situated in your new arrangement, and to ultimately learn what works best for you and your organization.

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