How To Have Difficult Conversations About Money, Long Term Care Planning, and More

The holiday season is stressful enough on its own. When getting together for the holidays means having hard conversations, that stress multiplies. We’ve learned a lot from Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen about how to have those stressful conversations, and we’re excited to share our favorite tips.

Before the Conversation

Commit to Communicating and Make a Plan

The first step to having a difficult conversation is to commit to having it. Find a good, low-pressure time to start the conversation, determine a safe and comfortable location, and make a conversation plan.

A good conversation plan starts with self-reflection. Take some time sit down and write out your point of view. Write out what you feel the issue is, how you feel about it, and what solutions you’ve tried. Take some time to really delve into what you’re feeling – sometimes hidden emotions can cause problems later on if they aren’t addressed.

Once you have a good picture of the situation from your perspective, take another sheet of paper and try to imagine this situation from your loved one’s point of view. Write out what they might feel the issue is, some ways they might feel, any solutions that you’ve seen them try or that might make sense from this point of view. It’s much easier to do this step after writing out your own side of the issue.

Take some time to compare the two viewpoints. They’re probably quite different! It’s easy to believe that our way of seeing things is the truth when in reality there can be multiple, completely valid, conflicting viewpoints.

Build Confidence Through Preparation

Build confidence by knowing yourself and your limits. Sometimes, something can happen that throws us off of our conversation plan, such as an unexpectedly strong emotion that comes to light or a reaction that we weren’t expecting. Ask yourself some questions beforehand to help prepare you for the unexpected.

• What about this conversation am I concerned, worried, or anxious about?
• What will it feel like if my loved one says that I’m a bad person, or accuses me of a character flaw?
• What insecurities do I have that might be triggered by this conversation?
• How will I feel if I or my loved one has a strong emotional reaction, such as crying? What will I do?
• How will I decide if I need to walk away from the conversation or take a break?

During the Conversation

Don’t try to control their responses

It’s normal to not want to cause someone to feel sad, angry, disappointed, or any other negative emotion. When we cause others to feel badly, it can shake our faith in ourselves and our perception of ourselves as a “good person”. Problems can arise, however, from trying too hard to defend everyone’s feelings.

When we try to avoid the negative emotions of others, we’re trying to exert control over their response in an unhealthy way. Without realizing it, we may leave out important details, downplay our own feelings, or forget to leave space for the feelings of others. It may seem tempting to avoid negative emotions and shy away from conflict, but, often, real solutions cannot be found without facing difficult emotions on both sides.

Let Your Curiosity Guide You

When something important is at stake, it’s hard to step back and let the other person have space to share. Try letting your curiosity guide the flow of the conversation. Ask questions about how your loved one came to the conclusions they’ve come to, or how they approach decision-making in general. Learn as much as you can about how they’re thinking and feeling, and offer to share what you’re thinking and feeling in return.

Express how you feel, not how you think they feel

Not everyone is used to addressing emotions directly. It’s easy to fall into the common patterns of judging or problem-solving instead of acknowledging emotions and behaviors in clear and understandable ways.

Statements to avoid:

• “You’re so …!”
• “Why do you always assume that…?”
• “If you’re feeling…, then you should do this…”
• “It’s your fault that…”
• “You always…” or “You never…”

Instead, try:

• “I feel…”
• “I want…”
• “I need…”
• “I’m worried that…”
• “I’m excited about…”

Find solutions together

Solutions that work require everybody to be on board. Everyone can work together to brainstorm potential solutions. A great way to start the problem-solving process is to watch a video about the issue together, then ease into a discussion about each of your thoughts and feelings on the subject.

Next Steps

The Retirement Safety Zone YouTube channel has clear, informative, and thought-provoking videos that make great conversation starters. We’re also happy to answer your questions directly – click below to schedule a time to talk.