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Navigating Tough Conversations with Family

Let’s be real: tough conversations with family are like trying to fix a leaky faucet while the water is still running. You know it must be done, but it’s messy, uncomfortable, and you’re probably going to get soaked. Whether it’s talking about aging parents, money, lifestyle choices, or long-buried tensions, these moments can feel like stepping into a storm unprepared. But here’s the good news: while these kinds of conversations aren’t fun, they can often lead to the most important connections we’ll ever have—if we’re brave enough to step in. 

Check Your Heart First 

Before you charge into that tough conversation, take a moment. Take a few moments. Breathe. Ask yourself, “Why am I having this conversation? What am I hoping will happen?” We often approach these moments with a subtle desire to be right or get our way. But if you’re honest with yourself, you probably want more understanding and connection. Let’s say you’re talking with a sibling about caring for your aging parents. Are you entering the conversation looking for a solution that works for everyone, or are you just trying to offload your stress? Jesus had a word for this: “First, take the plank out of your own eye, and then you will see clearly to remove the speck from your brother’s eye” (Matthew 7:5). In other words, do a heart check. Ask yourself if you’re more interested in being right or in being loving. It’s incredible how often the plank in our own eye clouds the way we see the other person. 

Set the Table with Kindness 

Picture this: you’re hosting a family dinner. You wouldn’t just throw food on the table, bark, “Eat up!” and expect everyone to have a good time, right? No, you’d probably set the table thoughtfully, maybe light a candle or two, and make sure everyone feels welcome. The same principle applies to tough conversations. When it’s time to talk about something sensitive—like finances or family dynamics—you’ve got to set the tone with kindness. Proverbs 15:1 says, “A gentle answer turns away wrath, but a harsh word stirs up anger.” It’s amazing how far a gentle start will take you. It’s like setting out a feast instead of throwing a soggy sandwich at someone. When you set the table with kindness, people are more likely to sit down and stay for the conversation. 

Talk About You, Not Them 

Here’s where things get tricky. In moments of high emotion, we default to pointing fingers. “You always…” and “You never…” are phrases that come naturally in these situations. In the words of Dr. Phil, “How is that working for ya?”  More often than not, it’s like pouring gasoline on a fire. Next time, try focusing on how you feel. If your teenager isn’t helping around the house, resist the urge to say, “You never do anything.” Instead, say, “I’ve been feeling overwhelmed lately, and I could really use your help.” This isn’t just good psychology—it’s biblical wisdom. Philippians 2:4 says, “Each of you should look not only to your own interests, but also to the interests of others.” By starting with “I feel” instead of “You always,” you’re inviting the other person to care about how you’re experiencing the situation rather than just defending themselves. 

Listen Like You Mean It

This is the hard part. If you’re anything like me, you’re great at hearing the other person, but actual listening? That takes work. We often listen just long enough to formulate our next brilliant point. But tough conversations aren’t about winning—they’re about understanding. And understanding requires listening. Next time you’re discussing something tricky—like politics or how to raise the kids—try this: instead of interrupting, say, “Tell me more about why you feel that way.” It’s amazing how that one question can open up a conversation. It doesn’t mean you’ll agree, but it does mean you’re listening. And real listening is one of the greatest gifts you can give someone. It’s the first step toward building bridges instead of walls. 

Progress, Not Perfection

Spoiler alert: not every conversation will end with everyone hugging it out, and that’s okay. Some issues won’t get resolved in one sitting. In fact, most won’t. The goal isn’t perfection—it’s progress. You don’t need to fix everything today. You have a win if you can walk away from a tough conversation and commit to keeping the dialogue open. Relationships aren’t a one-and-done deal; they’re a long, slow process of building trust, one conversation at a time. Think of it this way: tough conversations are like hiking up a mountain. It’s not comfortable, and there are moments when you’re tempted to give up. But if you keep going and talking and listening, you’ll eventually reach the summit. And what you’ll find there is worth every awkward, uncomfortable step. 

Difficult conversations with family are some of the most challenging—and most important—moments we face. When we approach these moments with a posture of humility, kindness, and a willingness to listen, we open the door to a deeper connection. It is never easy, but it’s the only way forward. At the end of the day, the relationships we build in those difficult moments are the ones that matter most.


David Simpson is the Community Care Pastor at Parliament Community Church in Regina, SK, Which is located near Harbour Landing. As a church, we offer programs for all ages, from children to youth, young adults to Seniors who are part of our Heritage groups. We are also diverse in cultural backgrounds but share a desire to grow as disciples of Christ together.