How To Have A Difficult Conversation With Your Boss

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Paper sign on door titled "stress reduction kit" that says "bang head here."

This should not be your coping mechanism for tough conversations.

Jobs are a lot like romantic relationships: You invest energy, spend a huge part of your life on them, and are fond of the people you’re with (hopefully). That’s why having a difficult conversation with your boss can feel a lot like going through a break up.

So what do you do when the time comes to leave your job, pursue your passions, or ask for a raise? Well, if you’re like me, you breathe—and then follow these three steps.


1. Take Your Time

As you may know, I’ve been on a mission to create my own coaching and lifestyle business for some time. Just recently, I decided to cut my day-job hours in half to pursue my business. It took me months to make this decision. I had to let it marinate before I took any action.

Is it this difficult for everyone? No. But you should take the time to think things through and make the right call for you. Why? Simply put, you don’t want to make rash decisions fueled by pure emotion. You also don’t want to stick your foot in your mouth.

Because I absolutely adore spreadsheets, I’m happy to share this Decision Making Template from the fabulous Jenny Blake of Life After College. Use it to take the time needed to weigh those tough job decisions!

2. Be Prepared

I failed miserably at this part. I pretty much just barged into my boss’s office and blurted out my decision. I was exhausted and burnt out, but these are not valid excuses—you SHOULD prepare before having a talk like this with your boss.

For me, it always helps to write stuff out. I write down my point of view and then go into every possible counterargument my boss may have. It helps me prepare for anything that may get thrown at me. It also helps me get very clear about what I want.

The one thing I did do right was having a recommendation for a replacement. If you’re going to leave, see if you can help them find someone. Don’t just stop showing up.

3. Stay Flexible And Negotiate

I went into my boss’s office thinking I’d have to either quit or work full time. I was quite surprised when my boss gave me the option to work part time, letting me focus on my business and still get some income.

From there, we negotiated a schedule that worked for everyone. Now, I have awesome hours and the time to get my business going.

The moral of the story? Always be open to different options. Who knows? You may end up with a better solution you hadn’t even thought of.

It may not hurt to brush up on your negotiating chops too.

Just Do It

No matter how much you prepare, your nerves will probably come up. I literally felt sick to my stomach about having this conversation with my boss.

At that point, there’s nothing to do except walk in there and do it. Before you know it, the tough talk will be over and a sigh of relief will come over you.

Trust me, you will feel so much better! Also, I recommend checking out this Marie TV video that will teach you how to see your nerves in a different light.

At some point in your career, you’re going to need to have a tough conversation with your boss. Whether you’re leaving a position or vying for a raise, it’s important to remember that it’s not the end of the world. Instead, see it as a lesson that will push you out of your career comfort zone.

How do you gear up for tough conversations with your boss? Share your secrets in the comments.

(Photo: programwitch)

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