Dealing with Difficult Conversations

May 29, 2015 By Katherine Tyler Scott

In a recent encounter with a very able colleague lamenting about having “lost it” in a situation in which there was in her view highly unprofessional behavior, I was reminded of how difficult it can be to be in such situations, and the courage and skill required to confront the individual involved.  It is a particular skill that Ki ThoughtBridge brings to our work, and one we always include in our leadership and negotiation trainings. 

There are numerous instances in our personal and professional lives that can precipitate “losing it” but there are reasons why this doesn’t happen; the main ones being self-awareness and self-control, two characteristics of emotionally intelligent leaders. 

Whether it is a peer or a boss, friend or family, client or vendor, we will find at some points in life and work where the need to have a difficult conversation is necessary. What we can’t emphasize too much is that more is needed than requesting a time, making an appointment or hosting others to converse about a tough issue. 

An Invitation is Not Enough

We have to do more than invite an individual or facilitate a group when the issues are adaptive and call for difficult conversations. We need to have a strategy, a plan, and most important a set of adaptive skills. 

If you need to talk with someone you feel has offended you in some way you will be the person initiating the conversation. So if it is your need you will need to be assertive. If the need is mutual then you will need to negotiate. Before the conversation ask some questions:

  1. What is the reason I want to talk with this individual? What is my purpose? What do I hope to accomplish? What do I want to change?
  2. What is my relationship to this person? What kind of relationship do we have now? What kind of relationship do I want in the future?
  3. How do I feel and why? What are the emotions that I feel-angry, hurt, betrayed, misunderstood, labelled, etc.?
  4. How much of what I felt/feel is related to the actual event and how much is related to past experiences?
  5. What am I willing to risk to attempt resolution? What is the cost? What is the promise? 

In addition to such questions as these, all of which can lead to increased self-awareness and increased empathy, you will be prepared to enter into the conversation with a sense of clarity and centeredness. 

We Don’t See the Same Things

We all have partisan perceptions. We come to the conversations with different histories, education, training, values, beliefs, and experience. We can legitimately see and understand things differently. So rather than immediately assume that we are right and the other person is wrong the adaptive work is to elicit the other person’s perspective of the same issue or event, and to share yours. We recommend doing this to achieve understanding. Understanding can diffuse a potentially explosive situation, but its quest cannot be permitted to be an excuse for inappropriate and/or hurtful behavior; it is the entry to making you and the other person conscious of assumptions, thinking behavior and actions. This is not an automatic skill; it is one that must be developed. We use tools such as The Ladder of Inference© for this purpose. 

Establish Guidelines

Establish norms or guidelines for the conversation so that both parties will know the mutually acceptable parameters and will see the value of creating a safe space for the conversation. External controls that can be referred to help to encourage risk-taking and provide a first step toward creating trust and a sense of psychological safety. If the conversation begins to heat up, honoring the terms that both developed and agreed to enables both to hold one another accountable, and lowers the heat created by fear and anxiety. 

The more you understand human and group development the more of an adaptive advantage you will have in leading and managing difficult conversations. Knowing what developmental stage individuals and groups experience will alert you to some of the main issues to be aware of and how to best intervene in the situation. 

Know the Biology as well as the Psychology

We know from recent research that in the limbic system in the brain resides the amygdala, the emotional center of the brain. It serves as the early warning to us whether we are in danger and whether we are to fight or flee. When we perceive an event or experience it goes directly to the amygdala which does not distinguish whether this is a current threat or something from the past; or whether it is real or imagined. Without the reflective awareness and emotional regulation provided by the prefrontal lobes in the cortex we are subject to emotional hijacking or “losing it” as my colleague experienced it.  In Ki ThoughtBridge we teach techniques such as the “Red Flag Rule” and the “Elephant Rule,” to prevent or diminish the emotional eruptions that can derail productive and successful conversations. So whenever you have or host a conversation around an emotionally laden topic it is imperative that there be norms and it is essential to know how to deal with the biology. 


Difficult conversations can be highly productive and can lead to the resolution of conflict, increased insight and learning, changes in attitude and values. To have them leaders must be skilled in more than invitation and convening. In convening groups to deal with adaptive and “wicked problems” the goal is movement toward constructive outcomes not an emotional free for all.  It is about conversion, a conversation in which the least outcome is mutual understanding and respect for differences and in which the best outcome is transformation of the mind and heart. This requires intentionality and a level of consciousness that comes from careful planning and adaptive skills development.