My denomination is engaged in a difficult conversation. But aren’t we all, and more often than we think? We’re always dancing around possible difficult conversations – with bosses and pastors, tough-to-love family members, obnoxious small group members, pestering employees, unhelpful custom service reps, and more.

As I prepare to facilitate a time to consider how we best have difficult conversations, I’m tapping into some categories I introduced in my book Toughest People to Love. Let’s look at some diagnostic categories for our difficult conversations.

  1. Is this a conversation I need to have? We’ve got to take a bit of time to consider this. Some difficult conversations feel extremely urgent in the moment. Answering this question often requires us to take a good, long look within ourselves first (which, of course, is a good “Jesus practice” – what’s in your heart?). I remember being triggered to near rage when a friend revealed to me a very harsh judgment by a supervisor of mine. I typed twenty different versions of a text blasting this person, but (thankfully) didn’t send one. I talked to a few friends in the days after, and my anger settled into a more sober sense of disappointment. As I transitioned from a more reactive to a more reflective place, I recognized that a conversation could come in time, but it was far more important to examine my own heart and my own reactivity. Principle: Rather than trying to change others, look to take the harder path of inner change.
  1. What do I fear and what do I need? When we relax our immediate ‘triggered’ prompt to react, we can tap in to our hearts where we find the “wellspring of life.” Our hearts tell us what we fear and what we need, and offer the wisdom to discern the path forward. The Spirit dwells within and becomes our conversation partner toward this end. When I learned of my supervisor’s comments, my rage took over my body. I felt blended with it. I could have punched a hole through a concrete wall. But as I descended into my heart and engaged a more reflective conversation, I experienced several fears – losing approval, being misunderstood, and a loss of joy in my work. I allowed myself some time to experience the reality of these fears and the concurrent sadness around the disconnect with my supervisor (all the while tending to the part of me that wanted to circumvent the entire process and rage!). In time, I began to discern the need for a calm and clear conversation with this person. I scheduled a face to face at that point. Principle: Rather than sabotaging relational connection with a quick response, honor your heart and discern what you fear and what you need.
  1. Exercise Curiosity. In Krista Tippett’s new book Becoming Wise, she notes that civil discourse requires that we identify the ‘good’ in the position of the other. This requires a posture of curiosity, a genuine interest in hearing from the other person and, even more, listening to their story. Much of our political and ecclesial discourse tends towards polarization – they are bad, we are good…their position is wrong, mine is right. We cite our authorities quickly – the Bible, the Constitution, the wise thinkers who agree with us. When we identify our fears and needs, we are able to approach a conversation with calm, compassion, and curiosity. I recall sitting down with my supervisor and beginning with conversation about life and family before getting into the tough discourse. When I mustered up the courage to engage, I said, “I’ve heard something about your perception of me that initially triggered great frustration in me, but I’m really curious to hear from you. May I ask you about it?” I didn’t sabotage my supervisor with my my frustrations and suspicions, but offered a chance to engage if my supervisor was willing. Of course, in that moment the other person’s anxiety ramps up, and I want to be aware of how I can cultivate non-anxious presence in that moment. My supervisor appreciated the opportunity to hear from me and respond, and while we did not ultimately come to the place of clarity I hoped for, we maintained a sense of connection and preserved a productive working relationship. Principle: Curiosity does not require us to agree, but invites us to listen non-anxiously and hear the heart of the other.
  1. Exercise Wisdom. Wisdom and folly are important categories when engaging difficult conversations. Folly implies hiddenness (Genesis 3), an inability to live in the light of truth, a tendency toward self-deception. Wise people are not perfect, but are capable of seeing their ‘stuff’ and repenting. Wise people do not tend to scapegoat and blame, but exercise curiosity with themselves and others. Those who tend toward folly blame-shift and deflect. They maintain positions with ultimate certainty and little curiosity and a fragile sense of their own inner authority. Now, I do wish Scripture was more clear and helpful to us on dealing with fools:

Do not answer a fool according to his folly,
or you yourself will be just like him.
 Answer a fool according to his folly,
or he will be wise in his own eyes. (Proverbs 26:4-5)

Even the writer of Proverbs is confused when it comes to have difficult conversations! Maybe that can allow us to practice some self-compassion and receive God’s grace when we find conversations difficult. I do think that Scripture paints, in broad strokes, a movement or continuum from foolishness to wisdom, from being hidden to living in the truth. In Toughest People to Love I offer three categories – Simple Fools, Self-Consumed Fools, and Sinister Fools.


Sinister fools have no capacity for self-knowledge, humility, or repentance. Likely deeply hurt at an early age, they have now become the “bully.” They win through intimidation, manipulation, and demanding ultimate loyalty. They are always right, and they claim the backing of Scripture, Polity, the Constitution, or whatever text or person they deem authoritative. Because curiosity and compassion are impossible, it is important to consider carefully how or if you will engage a Sinister Fool. There is no healthy conversation possible when you disagree, only war. And so, more often than not, I counsel people to protect themselves, and to tread with extreme care and caution.


As the title implies, this kind of folly is marked by an orientation toward self-interest. While not cruel like the Sinister Fool, the Self-Consumed Fool may employ charm, compliments, affirmation and seeming agreement before turning on you. The Self-Consumed Fool is deeply scared and insecure, and so protecting his truth, his position, and his rights is paramount. Sadly, the Sinister Fool is often barely capable of seeing this. Even repentance, when it comes, feels like a form of self-protection. You might experience a kind of Jekyll-and-Hyde effect with the Self-Consumed Fool, and in that you’ll be as confused as the writer of Proverbs as to how and when you should engage. Be wise as a serpent, innocent as a dove as you engage. On the one hand, I have compassion for the Self-Consumed Fool, because it is obvious that there is deep insecurity, shame, and over-compensation at play. I try to connect to his vulnerability and create a safe place to engage honestly. However, depending on how self-protected and hidden the “true self” of a Self-Consumed Fool is behind a false self of charm, competence, and certainty, you may not get very far. Choose what hills you are willing to die on very carefully with this one.


I hope that most of us, with gratitude to Jesus, are Simple Fools. We are simultaneously running toward the light of truth within and unware of ourselves in key ways. Yet, we are receptive, willing to see our blind-spots, eager to confess when we’ve blown it. Simple Fools are not wallflowers; they have deep convictions. However, they hold their convictions with confidence, not certainty (see Lesslie Newbigin’s Proper Confidence). They choose connection rather than certitude because they live from a deeper inner authority and do not need to attach their ego to power or a position. They confess that they could be wrong. They affirm, with John Calvin, that we are all like little children whose theologizing is like baby talk. More so, they long to become like little children – playful, generous, never taking themselves too seriously. It is more important to them to shed their ego than to win an argument, more important to maintain connection than demand affirmation. They hold their convictions with a depth and beauty that is attractive, not coercive. Simple Fools are grateful to engage difficult conversations, and model for the rest of us how it’s done.


We enter difficult conversations with fear and trembling because we long to live in relational harmony, justice, and goodness with one another. We are made in the image of a Trinitarian God whose relational harmony could only be described by early church theologians with the image of a dance. The “perichoretic” perfect choreography of the Trinity is our design, our inheritance, and our destiny. This is why union and oneness is central to the Upper Room discourse of Jesus. Jesus prays that we might be one as he and the Father are one. But oneness takes work.

TyporamaIn my various roles as pastor, therapist and professor over twenty years, I am mindful of how long it takes to move from ego-protective certainty to connection, from “I am right and you are wrong” to “I am curious to hear how you got there.” I see married couples for months in counseling before they can even lower their defenses and take a step toward one another. I see abuse victims whose pains runs so deep that the thought of living in any way except self-protectively feels all-too-vulnerable. I work with victims of racism whose bodies carry decades of hyper-vigilance and trauma, and who have little time and patience to hear the defensive excuses of others. I teach women and men whose theology was crafted in a particular context and with particular certainties who feel like doubt about one issue amounts to the collapse of an entire theological system. There is much that mitigates against wise, healthy, non-anxious, curious conversations.

But what is in us is more powerful than what divides us. The great equalizer is the imago dei. The one you disagree with remains an image-bearer. The one who hurts you, even still, is one whose being is the dwelling place of the Spirit. Our disagreement does not diminish God’s commitment to us. Our attacks against the other do not denigrate the dignity of God’s divine image. We commit to difficult conversations, amidst difference, because the One who dwells in us dwells in the other, because the way, the life, and the truth has taken up residence in each and every one of us – conservative and liberal, gay and straight, citizen and immigrant. God seems quite pleased to disperse his presence amidst difference. God seems quite pleased to cultivate unity amidst disagreement. Perhaps our penchant for uniformity and agreement can even be idolatrous, at times?

I enter into a difficult conversation with a heart to listening to the Spirit in the other. If all truth is God’s, our commitment to connection will allow us, in time, to discern together. It takes time, because the ego is most often in the driver’s seat with all its rightness and certainty and judgment. Committing to difficult conversations and to difficult relationships requires deep discipleship, because we will surely die along the way. The Communion Table became so central to our family because at it we die, we rise, and we return with and in Christ.

I have much more to die to. Do you? Every difficult conversation requires some kind of death. It invites us to the narrow way of Jesus. The easy way is the way of avoidance, judgment, distance, attack, categorization, and separation. The way of the Cross calls us to much, much more.

Additional Resources

Chuck DeGroat, Toughest People to Love

Marshall Rosenberg, Non-Violent Communication

Transforming Church Conflict, Van Deusen Hunsinger and Latini

Craig Barnes, The Pastor as Minor Poet

Dan Allender, Bold Love

Patterson and Grenny, Crucial Conversations

Life Together, Dietrich Bonhoeffer

Miroslav Volf, Exclusion and Embrace


3 thoughts on “thoughts on how to have difficult conversations

  1. Really good words, as always. It’s so easy to stay self consumed, and yet that keeps us stuck. The simple fool is much more honest, and therefore more attractive. But it requires a mini death. Powerful stuff

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