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Mastering Difficult Conversations with Your Boss

We all know that talking to our boss or reporting manager about work can be a bit scary and overwhelming at times. But- it doesn't have to be. With the right technique/approach you can turn difficult conversations with your boss into productive ones. Let's go through some simple steps to make these chats easier and more helpful for everyone.

Having a conversation with your boss

7 things you can do to master difficult conversations with your boss:


  1. Get Ready - Before you talk to your boss, think about your work. What are you doing well? Where could you do better? Write these things down. It's like making a list before going to the store - it helps you remember the important stuff.


  2. Pick a Good Time & Place - Ask your boss when they have time to talk. You could say something like, "I'd like to chat about my work. When would be a good time for you?" This way, you both can focus on the conversation. Additionally, take a step further and book a room/space that would allow you both to immerse into specifics and details.


  3. Start with the Good Things - Begin by talking about what's going well. It's nice to remember the good stuff! You could say, "I really enjoyed working on [project name]. I learned a lot from it."


  4. Talk About Getting Better - We all have things we can improve. It's okay to talk about these too. You could say, "I think I could do better at [task]. Do you have any ideas on how I could improve?"


  5. Ask for Your Boss's Thoughts - Your boss might have some good advice. Ask questions like, "What do you think I should focus on?" or "How can I help the team more?" This shows you want to learn and grow.


  6. Wrap Up on a Good Note - At the end, sum up what you talked about. You could say, "Thanks for chatting. I'm looking forward to working on these things and helping the team."


  7. Follow Up - After your chat, send a quick thank-you note to your boss. You could write, "Thanks for talking with me today. I'm excited to work on the things we discussed."


Remember, talking to your boss is just about getting better at your job. It's not a test or anything scary. Take a deep breath, be yourself, and it'll be okay. You might even find these talks helpful and not so bad after all!


Keep learning and growing - you've got this!


How confident do you feel about having difficult conversations with your boss about your performance?

  • Very confident

  • Somewhat confident

  • A little nervous

  • Extremely anxious




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