Four Key Questions to Ask Yourself Before Engaging In a Tough Conversation

Engaging or preparing to engage in a tough conversation is well…tough. And it’s tough for a reason. You want to get your point across, you don’t know how the conversation is going to go and you want to make sure you leave with some kind of resolution or next steps or feeling heard or making sure the other person feels heard. 

I’m Esther Weinberg and I’m the Chief Leadership Development Officer and Founder of The Ready Zone.

I have found that sometimes when we are ready to engage in a tough conversation there is actually one step we are missing. And that is – do you really need to have the conversation? Not because you want to avoid the actual conversation, because sometimes we really don’t need to have it. Yet what is the barometer that measures whether or not that’s true?

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If you launch yourself into a conversation without having done the self-reflection necessary, it is less likely you will come from a place of curiosity, and more likely you will come from a place of judging—and that can render the interaction ineffective. Being a leader in relationship with others takes a lot of pausing, reflecting, and self-awareness. It takes being honest with yourself, dignified in your treatment of yourself; and only then can you treat others with dignity and make them feel trusted, respected, and safe.

When you ask yourself these four questions, you allow yourself to shift toward being more neutral, less biased, and you can then more adeptly handle the other person’s thoughts, emotions, and perspective once you get into the conversation. Pausing and reflecting on these questions helps you to elevate your perspective and behavior, so that you can genuinely be curious about and hear and understand the other person and what they say. This approach gives you the best chance of success.

If you are interested in digging deeper in what we talked about, the best next step is to fill out our Needs Assessment. I’ll be happy to connect with you. And remember…Better Leaders, Better People, Better Results.