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The Only Way Young People Can Get Better At Having Uncomfortable Conversations With Their Bosses

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When you’re young your life is full of “firsts,” especially when it comes to work. First post-college job interview. First time negotiating your salary. First day on the job. First presentation. One “first” that creates overwhelm for young people is the first uncomfortable conversation with their boss. So much so that many young people avoid these kinds of conversations when in actuality there is only one way to get comfortable during uncomfortable conversations: have the uncomfortable conversation.

Yes, that's right. The only way to feel less anxious about something is to face it head-on and do the thing that’s making you anxious. The more you do things that make you anxious, the easier they’ll become and suddenly one day you realize that the things you were so afraid of aren’t as scary as you originally thought.

At the same time, if you actively avoid something that makes you anxious at work, the harder it will be in the long-run and it may even spill out into other aspects of your life. If you avoid having difficult conversations at work, you may start making excuses in order to avoid having difficult conversations with your partner or your roommate. Suddenly something that was once challenging but doable has taken on a life of its own.

While having that first difficult conversation will never be easy, there are strategies you can use before, during and after the conversation that will help reduce your anxiety and improve your confidence.

Before The Meeting

Before you start any difficult conversation, you want to think about timing and tone. You want to make sure you initiate the conversation in the right environment and when the other person is able to give you their full attention.

1. Timing

Set a time to meet with your manager and make sure to send an email letting her know what you’re hoping to discuss during the meeting. This way you won’t take her by surprise and she’ll be ready to hear what you have to say.

2. Tone

When it comes to conversations, you have no control over what the other person is going to say or how they’re going to respond. You do have control over what you say and how you say it. Before the meeting, take some time and practice. Write down all of your thoughts as a jumping-off point. Keep revising until all of your points are clear and concise.

Finally, 10-to-15 minutes before the meeting, find a quiet place to close your eyes and visualize yourself speaking with your manager and see yourself being confident and articulate. Remind yourself that while this conversation might be hard at times, your goal is to get your point across in a calm and thoughtful manner.

During The Meeting

It’s happening! You’re in the meeting, here are some things to remember:

1. Use “I” Statements To Express How You’re Feeling

Starting sentences with “You said you would do XYZ” or “You never listen to what I have to say” usually makes people feel like they have to jump to the defensive. Make sure you’re using “I” as much as you can, such as, “I feel at times my point of view isn’t being heard.”

2. Be Transparent

This is a first for you so own it and be transparent. Say something like, “This may not come across the right way so bear with me while I try this” or “This is the first time we’ve had this kind of conversation so I’m feeling a bit nervous.” Naming what’s happening in the moment is a great way to disarm the other person. You’re showing a bit of vulnerability, which will hopefully make the other person more at ease.

3. Stay Flexible

You have an idea of your ideal outcome but that may not align with what your boss or the company needs or wants right now. Think about some other outcomes that would be agreeable to you if you and your boss aren’t on the same page.

After The Meeting

Phew! You did it! You got through your first tough conversation in one piece. What are the next steps?

1. Thank Your Manager For Their Time

No matter how things went it’s always good to take the time to acknowledge that they took the time out of their day to speak with you.

2. Review What You Discussed So It’s In Writing

Right after the meeting sit down and write everything you heard during the conversation and what you and your manager agreed upon during the meeting. Later that day, or the next, email your manager to review what was discussed so it’s in writing and you can refer back to it if necessary.

3. Pat Yourself On The Back

Finally, and this is most important, take a moment and praise yourself for doing a hard thing. Treat yourself to something nice as a way of acknowledging you got through your first (but not your last) uncomfortable conversation.

Always remember just because a conversation is uncomfortable doesn’t mean it shouldn’t happen. It’s through difficult and challenging conversations that we grow as individuals. It forces us to get vulnerable, take some risks and sit with discomfort, which will help you show up as your most authentic self at work.

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