How To Have Hard Conversations

Having conversations about money isn’t always comfy – sometimes, it’s downright difficult. I’ve had the opportunity to hone my hard-conversation-skills with both family and friends over the last few years, and with the help of an amazing therapist and lots of reading I’m getting better every time. Here are a few things that will make your difficult conversations more productive, gentle, and honest.

  • Know your goalIf you’re not sure what you want to get out of a conversation, that’s a sign you aren’t ready to have it yet. Convincing someone of your point or way of thinking is always an ambitious goal – and sometimes quite unproductive. I recommend aiming for understanding instead of agreeing.
  • Practice the hardest and more important things you want to say. For me, sitting in tension is uncomfortable and I can get overwhelmed quickly. I always practice what I want to say, and sometimes even record myself saying it into the voice memo app on my phone. Then I play it back and listen to it a few times leading up to the conversation, so that if my mind goes “blank” I kind of muscle memory revert to what I’ve already heard myself say.
  • Listen more than you talk. Make it your goal to never interrupt. Instead of responding the moment after they are done speaking, give it a beat and see if they say something else. Typically they will, and it will usually be more helpful than the first thing they said.
  • Give what you want to get. Do you want to have a vulnerable and honest conversation? Then set the tone by modeling that yourself.
  • Remember your body. Take deep breaths, plant your feet on the ground (don’t cross your legs) and don’t clench your fists. If I’m at a table and the people I’m speaking with can’t see my hands in my lap, I open them towards the sky.
  • Think about how you want to be remembered. I recently had a tough conversation where I wanted the other person to, quite frankly, be impressed with how I handled it. Their impression of me was important. I wanted to come across as calm and understanding, so I made sure my voice was measured and low, and nodded while the other person was talking. I repeated back what they said to make sure I understood. (And to be clear, I truly was calm and understanding about the situation, but I didn’t want my anxiety to take over and make me appear defensive or anxious – so I kept that in mind during our interaction.)
  • Focus the conversation. If you get off the rails or start repeating yourselves, refocus by saying “I want this, and you want that – can you see a compromise or way to move forward here?”
  • Know when to end it. Ask what the other person needs moving forward or what their expectations are of you, and if the conversation doesn’t go well, it’s okay to say we clearly see this differently, we can agree to disagree and move on or we can return to this topic in a few days, weeks, months whatever makes sense for your relationship.
If you want to get in touch with me for any reason, you can find me, herehere or here.

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