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How to have hard conversations



Everyone sees difficult conversations differently. Maybe you're good at gracefully ending a dating relationship but struggle to tell your boss you'll resign without a promised promotion. Or you might easily confront a colleague who takes credit for your ideas, yet feel uneasy telling a friend you won't spend thousands on her destination bachelorette party. Regardless of the situation, we all face challenging conversations, big or small. Avoiding them can lead to resentment and feeling drained. However, you can make these discussions more manageable and productive with some strategies, as advised by experts.


Before approaching the person, talk to yourself. The dread often comes from a fear of disappointing others, especially for people-pleasers. According to Najwa Zebian, it's about believing you’re bad or selfish for raising issues. This fear is often rooted in childhood experiences. Remind yourself that you’re an adult who can handle disappointment or rejection.


Reframe the conversation as relationship-building rather than destructive. Genevieve "Jenny" Dreizen suggests that exposing vulnerability can deepen connections, turning relationships solid or, if necessary, ending them truthfully.


Choose the right moment for these discussions. Avoid times when the person is tired or preoccupied, and give them time to process. Don’t rush to a resolution.


Consider your opening statement carefully. Avoid phrases like "Don't be mad at me," as they might prevent others from expressing their feelings. Normalize the process of "rupture and repair” in relationships, learning to say sorry and confront issues constructively.


Write a script to guide you. For instance, if breaking up with someone, acknowledge the discomfort, express your feelings, and explain why you need to end things. If you are leaving a job, be thankful for the opportunity but firm about your decision. When confessing a mistake, admit discomfort, apologize, and offer to address your behavior. In confronting someone, express your vulnerability and desire to resolve the issue together.


These approaches help navigate tough conversations with more confidence and clarity.  

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