7 Tips for Having That Difficult Conversation About Truth

By Caleb Kaltenbach  

Having conversations about truth will always be difficult. (That may be the understatement of the decade!) Whether it’s difficult conversations that address someone’s pride, selfishness, bitterness, or, well, you fill in the blank, we’ve all been the recipients and bearers of “tough love talks.” And an already difficult conversation becomes even more complicated and emotions increase dramatically when the topic centers around a lighting-rod societal issue.  

Unfortunately, many who are tasked with confronting another person can go to extremes when sharing truth. They might challenge a person too harshly or they might be too fearful and not be truthful enough. While truth conversations are challenging, they should never sabotage anyone’s spiritual health. Prioritizing such interactions creates opportunities for future dialogue and helps pave the way for the other person to draw nearer to God. 

Preparation for tough discussions is paramount. I contend you should spend as much time preparing for truth conversations as you’d spend studying for a sermon, lesson, or presentation. Preparation will help you to be clear and intentional with your words. Without this readiness, your difficult conversation will amount to sideways energy leading to nowhere but frustration. Worse yet, you’ll probably sabotage a tremendous amount of influence with the other person. Here are seven tips that might help your difficult conversations.  

1. LISTEN FOR CUES 

In a best-case scenario, the person you need to have a truthful discussion with approaches you to talk. More times than not, however, you’ll probably need to initiate the conversation. As such, timing is everything. In your everyday interactions with this person, listen for certain statements and questions that could indicate their openness to a conversation. Examples include these:  

• “Why is this happening?” or “Why did this happen?” 

• “I never thought I’d end up here.” 

• “I never thought _______ would happen.” 

• I don’t know what to do.” 

• “I’m not sure what’s next.” 

• “What do you think about faith and ______?” 

• “No one understands me or even tries.” 

• “No one listens to me.” 

• “I feel alone.”  

These statements and questions suggest the individual might be contemplating life issues and thus might be open to a deeper discussion. 

2. ASK QUESTIONS 

Assuming the worst about someone never brings out the best in any conversation. Everyone is different, so when it comes to having truth conversations, you need to “pivot” depending on whom you’re engaging with. Taking a strategic approach to sharing truth doesn’t necessitate making truth more palatable by watering it down. Jesus’ method of communicating to Nicodemus was distinct from his approach with the woman at the well. However, he conveyed the same truth to both individuals. Paul’s message to the Sanhedrin was very direct, but he set aside time in his message to relate with the Athenian philosophers. 

Just as missionaries and church planters must study contextualization, you and I are obligated to think more deeply about those with whom we have difficult conversations. This is where questions come into play—because questions are imperative for such meetings. Asking yourself questions about the meeting and about the person compel you to think intentionally. Examples include these: 

• What do I hope to accomplish in the conversation? 

• What do I hope they gain from the conversation? 

• How should I bring up the conversation?  

• What can I do to help them take one more step toward Jesus?  

• How can I best emphasize my love and God’s love for them? 

• What do I hope they feel after our meeting?  

Also, asking questions during the meeting can help squelch tense moments. Questions can defuse passionate emotions because they invite the other person to dialogue rather than defend themselves. Refusing to ask questions before and during the meeting produces wrong answers and ensures faulty perspectives. The conversation will start heading in the wrong direction, with each step taking you further away from a helpful solution. You will also find yourself more distanced from the person you care about. 

3. DETERMINE THE GOAL OF THE CONVERSATION 

Difficult conversations sometimes end badly because there was no goal (or no helpful goal) for the meeting. This might be obvious, but your goal in tough conversations isn’t to convince the other individual to praise your logic. The goal isn’t to debate or to win an argument. Leveraging the conversation to validate your personal feelings isn’t the goal. Ego-driven morality is never the goal. (Also, behavior modification for the sake of behavior modification never glorifies God—it’s so diametrically opposed to Christ-centeredness that it makes you appear legalistic and pushes the other person toward resentment). 

There are several goals for every difficult conversation about truth. Inspiring people to take another step toward Jesus is the ultimate goal, but you also want to maintain influence with the person so you can have another meeting. You should also have a specific goal for that particular conversation. The goal might be to bring a problem to the other person’s attention. It could be that you need for them to understand how their choices are impacting others. Maybe that individual doesn’t realize their attitude is unbiblical. Whatever the goal might be, don’t have more than one or two specific goals per tough conversation. The person you’re speaking with will likely be emotional, so the longer the meeting lasts, the more emotions will take over, and the less likely you will be to inspire them toward any goal. 

4. ANTICIPATE DIFFERING PERSPECTIVES 

Reality becomes messy anytime your beliefs collide with contrasting opinions from a loved one. Society pushes the narrative that it’s easier to manufacture villains out of those who disagree with you than learn more about them and invite them to dialogue. Without dialogue, Jesus’ followers will never become bridges for society. The idea of dialogue actually implies disagreement. So, as you prepare for your difficult conversation, you need to be ready for differing perspectives. Doing so can ease confusion during the meeting.  

In recent years, I’ve noticed a trend: depending on context and a person’s life experiences, a Christian may believe two different perspectives on the same issue. To say it differently, a believer might hold a biblical belief about a topic while having a seemingly contrasting civil view on the same topic. As an example, many Christians theologically disagree with same-sex marriage but, from a civil perspective, believe a person should be free to marry someone of the same sex. Also, a believer might believe getting drunk is a sin but wouldn’t support a countrywide ban of alcohol.  

While maintaining differing perspectives on the same issue might be positive or negative, it’s a way of life. Just as you can experience various emotions about an individual, you can have different perspectives on an issue. My intent isn’t to justify any specific view, but to help eliminate confusion during truth conversations. It could be that whomever you’re speaking with might hold contrasting views on the same topic while your theological view and other views on the topic are aligned. 

5. PLAN AN INTENTIONAL CONVERSATION 

As you prepare for the actual conversation, ask yourself more questions: 

• What’s the best day of the week for the meeting?  

• What’s the best time of day for the meeting? 

• How long should the meeting be? What time does it start and end? 

• Where should the meeting be held? 

• Should I have someone accompany me to the meeting?  

I cannot stress enough the importance of these details! For instance, the conversation is likely to drag on if you don’t set definitive starting and ending times. Again, the more it drags on, the more emotional the meeting will become. Also, it might be that you both work certain hours, so evening is the only time you can meet. On the other hand, if you can meet any other time, do so, because people are more emotional at night.  

On the meeting day . . . 

• arrive earlier than the person with whom you’re meeting  

• don’t change the agreed upon meeting place unless necessary 

• don’t meet longer than the meeting is supposed to last 

• pay for their meal or coffee (if you’re able to do so) 

• don’t keep notecards in front of you (that’s cringy)  

Attention to these minor details communicates your concern for the person and shows you to be invested in them and the meeting. 

6. BE FULLY PRESENT 

Being fully present with an individual means being physically present during the meeting. While this idea doesn’t offer a silver-bullet solution to the problem you’re addressing, it can be a catalyst to help you understand another individual’s perspective. Here are some ways to show you’re engaged in the conversation: 

• maintain eye contact 

• keep your cell phone off the table (or at least, turn it upside down) 

• don’t check your watch 

• try not to fidget 

• face them during the entire conversation 

• smile as much as you can (without being weird)  

Another aspect of being fully present is talking less so you can listen more. If you think listening is easy, you probably aren’t doing it well. My wife is a therapist, and she has emphasized to me time and time again how challenging it is to really listen. Yet, listening more and talking less has a tremendous benefit—people are more likely to feel safe when their concerns and experiences are acknowledged. So, during such crucial meetings, my strategy to listen well involves having their story playing in my head as if it’s a movie. Without knowing it, on a very low level, I start reacting to what’s happened to them (as portrayed in my head). This practice doesn’t work for everyone, but it personally helps me listen more and talk less. 

7. WRITE DOWN WHAT YOU WANT TO SHARE ABOUT TRUTH

Society’s trends and values are always shifting, but God’s Word never changes. Thus, the Bible can be trusted to guide you and the person you’re sharing with. I’d encourage you to write out the truth part of your conversation and ask yourself questions like these: 

• What is the person struggling with? 

• What does the Bible say about their struggle? 

• What lies might the person be tempted to believe? 

• How will this person best hear truth? 

• Where is God offering hope during their struggle?  

When you begin sharing truth, start that part of the conversation with Jesus and keep him at the center. Concisely share what you believe and don’t talk forever! Keep your comments to five minutes or less. I know five minutes doesn’t sound like much time, but when you listen to someone talk for that long (especially about a difficult issue), it can seem like an eternity.  

Throughout the meeting and after it ends, emphasize Jesus’ love for them. Reassure them of how much you care about them and always point them toward hope. More than likely, this will be the first of several meetings you will have with the person. Truth conversations are spiritual marathons, not sprints. So, love them in both grace and truth. 

Caleb Kaltenbach serves as research pastor at Shepherd Church in Los Angeles. He is founder of The Messy Grace Group where he helps churches love and foster community with LGBTQ individuals without sacrificing theological convictions. This article is adapted from his book, Messy Truth.