How to Have Hard Conversations at our Holiday Tables

How to Have Hard Conversations at our Holiday Tables

By Joe Bishop

We all have them, of course. The difficult relationships, the people who have hurt or disappointed us. The people we just don’t like or who are so different that we struggle to understand them and don’t even want to try. And for many of us, some of those people are called family.

The coming weeks will be filled with holiday meals and celebrations, office parties, and plenty of opportunities to interact with the people we love and enjoy the most. But also with our difficult people. Which means now is a great time to reflect and decide who we want to be with and how we want to be with them. 

Navigating difficult relationships is a common theme for any counselor. On a recent day, I had three consecutive conversations with clients that centered on a similar issue. They each wanted to talk about an upcoming encounter they would be having with a difficult person, someone with whom they had experienced deep hurt and brokenness. 

My first client’s difficult person was a critical and controlling parent, the next client’s was a formerly close friend who had betrayed their confidence, and the third’s was a co-worker who was undermining and spreading lies about them. All three admitted they had been avoiding their difficult person but said this only made them more anxious. They all wanted to talk about strategies for how to deal with the difficult person in a healthy way.

What does that look like? What do I want my clients to know, remember, and practice?  There are no formulas or quick answers or three easy steps, of course. Each person’s situation is different, and every story deserves to be listened to carefully. I don’t have all the answers because I am grappling with these same questions. But I believe some principles and practices can bring life and healing to us in the midst of these challenging relationships. Here are my thoughts on the three things most necessary for engaging well with difficult people.  

First and most important is to come from a place of security about yourself. Everybody struggles with insecurity; it’s just a matter of degree. We live in a world that is rife with comparison, competition, and codependency. We are bombarded with messages of scarcity, messages that want us to buy things so that we will be more loveable and attractive. This is, I think, the very essence of what the Psalmist calls “the counsel of the ungodly.”

In utter contrast, I want my clients to live out of the reality that they are deeply loved, fully valued, and delighted in by God. God’s love will never change; it will never be diminished or distorted. 

This is so easy to say but so difficult for many of us to believe. Yet, only when we believe we are deeply loved can we enter into a broken relationship with freedom and honesty.  No person can rob us of what is most important. The judgmental parent or betraying friend can hurt us, but they can’t destroy or define us because we are worthy of love and belonging, period.

That’s why the most important thing you can do to prepare for a holiday dinner at your older sibling’s house (the one who always makes you feel inadequate and likes to tell you why you’re wrong about everything) is to spend at least ten minutes every morning reflecting on God’s love for you and delight in you.

The second important idea for navigating difficult relationships is to be clear on your goal. My client who had been hurt by a friend knew that she needed to have a courageous conversation, but she was unclear on her goal. She initially said her goal was to get the other person to acknowledge her wrongdoing and apologize so that the friendship could be restored. 

But a good goal has to be within our control, and we can’t control another person’s response. Restoration was her desire, but she changed her goal to be this: she would say what she wanted to say in the way she wanted to say it; she would speak the truth in love. 

This is consistent with the brilliant and realistic statement in the New Testament: “Be at peace with all people, as much as it depends on you.” We can only control ourselves. Figuring this out took my client back to the fact that she wanted the relationship to be reconciled, but she didn’t need it. She could be whole and healthy regardless of the other person’s response.

The third necessity for difficult relationships is to practice healthy communication. This is what gets most of the attention and where most people want to focus. But if you are not secure about yourself and if you don’t have a clear and appropriate goal, you won’t be able to communicate well. It’s just not possible. 

Because healthy communication means:

  1. Making direct requests—being clear, open, honest, and direct with our words.
  2. Listening to understand, not to respond.
  3. Not interrupting—letting the other person finish their thoughts without needing to correct them or jump in with our truths.
  4. Not making negative assumptions—this is subtle but vitally important—not assuming we know the other person’s motives and not thinking the worst of them.

Much, much more can be said about these practices of healthy communication, of course. But they require the kind of courage and vulnerability that takes us back to security about ourselves.

It all starts there. 

As we continue through this holiday season, let’s approach all our relationships with the goal of listening and loving well, knowing that we are ok, in the deepest, truest sense, because of the security of God’s love. 


Joe Bishop is the co-founder and director of Respero and has been a pastor for over 35 years, serving in churches in Pennsylvania, Ohio, Indiana, and California. He has a deep-seated conviction that local churches are meant to be genuine healing communities and tangible expressions of the love and grace of Jesus. Joe received his academic training at Capital University, Grace Theological Seminary, Santa Clara University, and Trinity Theological Seminary. He and his wife Kathy have been married for over four decades and enjoy their adult children and grandchildren. Joe is also an avid reader, hiker, and lifelong sports fan who is still celebrating the fact that his favorite team, the Chicago Cubs, actually won.

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