How To Have Difficult Conversations With People You Love

Sometimes, loving people means having hard conversations.

We're updating our original post, How to Have Difficult Conversations About Money, Long Term Care Planning, and More below with more insights and tips that you can use in many different situations - from talking about hard topics like finances and caregiving to negotiating whose house the holidays will be hosted at this year.

If you haven't read Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen yet, it's worth a read! It goes into depth about the art of having difficult conversations in a manageable and respectful way.

Before the Conversation

Make a Plan

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

A good conversation plan starts with self-reflection. Take some time to sit down and 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.

Then, take another sheet of paper and try to imagine this situation from your loved one’s point of view. What might they feel the issue is? How do you think they feel? What solutions have you seen them try? 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 many different ways to look at an issue.

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?
What emotions might this conversation bring up in me? How can I manage those emotions in the moment?
How will I decide if I need to walk away from the conversation or take a break? What will I say?

When thinking about emotions, it can help to consult an emotion wheel, also known as a 'feelings wheel':

*Image Source:* *https://feelingswheel.com/*

When using a feelings wheel to plan for or understand emotions, you can start in the middle with a more vague feeling, and then move outwards to identify something more specific. Even just being able to identify and name what you’re feeling can make managing strong emotions easier in the moment.

Other ways to prepare

You can prepare in other ways too, such as writing your concerns out as a letter. Some of us are just more comfortable putting down our thoughts in writing. You don’t have to send the letter - you can use it as space to brainstorm, express your thoughts and feelings, or perhaps read it out loud to your loved one as a way to start the conversation.

Consider talking your concerns over with someone else, like a friend or family member. This is great practice for considering other perspectives, and you might walk away with new ideas for the discussion. You can even have a practice conversation where you try out different ways of saying things and see how they feel.

It’s also important to know how to exit a conversation that’s gotten too heated. Make an exit plan - for example, if you’re meeting at a restaurant, you may prefer to bring cash to pay more quickly if you feel you need to walk away.

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…”

“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.

After the Conversation

Make time to take care of yourself

Difficult conversations are just that - difficult! Take a breath and remember that you've just done something challenging. Give yourself permission to take care of yourself - whether that means taking a walk, giving yourself some time alone with your favorite book, or keeping up with other people you love.

Following up

Sometimes our loved ones need some time to process what we've said. If you can, consider whether you can give them a bit of time - a few days, a week - before reaching back out or bringing the issue back up. In an urgent situation, this may not be possible, but even a few quiet moments to think something over can help a loved one collect their thoughts.

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.