4 Tips to Get Your Boss to Do Something They Don’t Want to Do

Being the bearer of bad news is never easy. Worse is when you have to try and break something to your boss, or maybe even ask them to do something they really don’t want to do. Here are some tips for how to make that conversation less awkward, and more awesome.

(Photo Credit: potential past/Flickr) 

1. Imagine Yourself on the Other Side

Whether you’re trying to convince your boss to let you transfer teams, or just want to propose a potentially “unpopular” work idea, it’s a great idea to first imagine yourself in their shoes. What would you think if someone came to you with a similar proposal? How would you be likely to take it? If you can, find a neutral (non-work) party to practice your proposal on. If they say “that’s kind of abrupt” or “wow, harsh” then maybe it’s time to rethink your presentation strategy.

2. Soften the Blow as Much as Possible

Instead of just blurting out “I want out of your crazy team!” (or something), try to make an easy lead up to the possibly unpopular conclusion. Remember you’re “selling” your boss on a new idea. If you’re trying to move out of their team, think about what your boss will have to consider, like how it reflects on them as a boss, how hard it will be to fill your position, what will happen to your current projects, etc. Try to ease their fears by thinking of solutions to all of these potential hiccups. If you solve for all the things that could lead to a “nope,” then all that’s left is a “yes.”

3. Time Your Meeting Well

Just like when you were a kid and you knew better than to greet your parents at the door with some loud, complicated complaint about your sibling, same goes with your boss. Think about when they’re most stressed, like right before your big department meeting each week. Even though they’re sitting at their desk peering into their computer screen, and they seem to have a “come bug me” sign on their heads — they don’t want to hear from you right then. Lifehacker proposes you try to schedule a private one-on-one meeting, or maybe take the out of the office hubbub for a coffee and a quick chat some afternoon.

4. Don’t Count Your Chickens Before They’ve Hatched

Even though your plan might be amazing, it’s not a reality until it’s … well, a reality. If you spent your day fantasizing about some new job, project, or way of doing things, but you neglect your current work, it’ll get noticed. Your boss won’t grant you a “favor” (especially if it’s something that they don’t want to do anyway) if you haven’t earned it. Keep reaching for the stars with your current work, and then go in to change the world with your new ideas.

Tell Us What You Think

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