Difficult Conversations: How to Discuss What Matters Most

“Once you understand the challenges inherent in the Three Conversations and the mistakes we make in each, you are likely to find that your purpose for having a particular conversation begins to shift. You come to appreciate the complexity of the perceptions and intentions involved.”

This quote emphasizes The Need for Self-Reflection and Self-Awareness. The reason we want to initiate a conversation might change when we begin to investigate the various reasons for the conversation. It is rare that a difficult conversation exists for single, simple reason; once the conversation is thought out in detail, one may discover a deeper reason for one’s discomfort, and the conversation can be attacked in a more constructive way.

“What we are saying does make sense. What’s often hard to see is that what the other person is saying also makes sense.”

The conversation in our minds begins from our perspective alone because that’s all we have. In dialogue, however, we have to remember that the other person has their own way of seeing the problem, and is likely attempting to make sense of it as genuinely as you. Truth isn’t relative, but there can be more than one side to what really happened.

“Inevitably, we end up noticing some things and ignoring others. And what we each choose to notice and ignore will be different.”

Even when people stand next to one another and see the exact same event take place, there might be two different stories and perspectives. Depending on what an individual considers important, or happens to notice by accident, their report of events may vary—sometimes even widely.

“Much of the first mistake can be traced to one basic error: we make an attribution about another person’s intentions based on the impact of their actions on us.”

We often equate intentions with the effect that words and actions actually elicit. However, intentions and impact are not necessarily the same thing: We may have the best intentions, but hurt someone’s feelings. Someone else might have wicked intentions, but we might misunderstand them and naively assume the best. In either instance, the distinction between the intention and impact needs to be acknowledged to accurately assess words and actions in conversation.

“Understanding how we distort others’ intentions, making difficult conversations even more difficult, is crucial to untangling what happened between us.”

We tend to give ourselves the benefit of the doubt when we assume the worst of other people. In order to determine what really happened and what’s really going on, we need to try and purge predetermined assumptions and take a clear look at the reality, not our (perhaps) distorted view.

“But even in situations that require a clear assignment of blame, there is a cost. Once the specter of punishment—legal or otherwise—is raised, learning the truth about what happened becomes more difficult. People are understandably less forthcoming, less open, less willing to apologize.”

The question of blame is not one that should be erased completely, but it should rarely be the first thing mentioned. Blame might eventually need to be assigned, but once the question of blame arises it will color everything that follows. Therefore, the conversation should remain as open-ended as possible for as long as can be reasonably maintained.

“Seeing yourself through someone else’s eyes can help you understand what you’re doing to feed the system.”

People are very good at spending time assessing others’ actions and attempting to discern their motives. In contrast, we are often very weak when it comes to honestly assessing ourselves. Attempting to see ourselves through somebody else’s eyes can open up new ways of understanding our own motivations.

“Feelings are too powerful to remain peacefully bottled. They will be heard one way or another, whether in leaks or bursts. And if handled indirectly or without honesty, they contaminate communication.”

It is a mistake to assume that we have a choice when it comes to relating our emotions. Our feelings will make themselves known regardless; the real choice is going to be when, where, and how. The most prudent path is to deal with emotions in an honest and straightforward manner.

“What does it mean to negotiate with our feelings? Fundamentally, it involves a recognition that our feelings are formed in response to our thoughts.”

We can trick ourselves into thinking that our feelings are dominant, and that we must abide by their rules. This is false. We have far more control over our emotions than we usually think, and we need to remain open to the possibility that further reflection and information will radically change them.

“Our anxiety results not just from having to face the other person, but from having to face ourselves. The conversation has the potential to disrupt our sense of who we are in the world, or to highlight what we hope we are but fear we are not.”

In many cases the idea of having a difficult conversation is made even more difficult because we have to be able to take a long look in the mirror. Often, we are afraid of what we might see. Difficult conversations tend to illuminate what we may fear seeing about ourselves; avoiding them means being able to maintain the illusion of an identity that we’ve concocted within our own minds.

“The biggest factor that contributes to a vulnerable identity is ‘all-or-nothing’ thinking: I’m either competent or incompetent, good or evil, worthy of love or not.”

It is almost impossible to avoid the kind of binary thinking that characterizes so much of contemporary thought. The problem with this paradigm is that it creates a world where we can only think in stark dichotomies. If we detect even a hint of incompetence, we overcorrect and assume that we are wholly and completely inept or unprepared. There is no room for nuance.

“We can’t change someone else’s mind or force them to change their behavior. If we could, many difficult conversations would simply vanish.”

In the end, it must be remembered that the art of negotiation is simply that: It’s an art, not a violent act whereby another person can be forced to submit. It is a skill that is acquired and cultivated, by which we hope to allow another to see the logic in our thinking and the validity of our feelings.

“The gold standard here is working for mutual understanding. Not mutual agreement, necessarily, but a better understanding of each of your stories.”

Difficult conversations are not principally about arguments or conflict. They are about how to better understand the other person in order to come to a position that can be mutually agreed upon as the best possible solution. Aiming to understand the other person, rather than aiming to win, is almost always going to yield better results.

“But while the beginning is fraught with peril, it is also an opportunity. It’s when you have the greatest leverage to influence the entire direction of the conversation.”

An age-old philosophical principle is that a small error at the beginning will yield a much greater error later on. The same is true in initiating conversations. The best chance at steering the conversation in the direction you want it to go is at the very start; if the opening interaction is wise and healthy, there is a great chance that the rest of the conversation will continue along the same lines.

“A real conversation is an interactive process—one where you are constantly going to be listening, sharing your view, asking questions, and negotiating to get the conversation back on track when it starts to go off the rails.”

Conversations are dialogue, which are by definition an interaction between more than one single person. In other words, conversations are not meant to be turn-based monologues, but genuine interactions where each builds on the last.

“Listening well is one of the most powerful skills you can bring to a difficult conversation. It helps you understand the other person. And, importantly, it helps them understand you.”

Listening skills are usually developed; they are not innate abilities. Listening well solves two problems at once: It allows you to understand the other person, and it allows the other person to acknowledge your engagement and sincerity, turning them into a more invested listener.

“If you don’t have a question, don’t ask a question. Never dress up an assertion as a question. Doing so creates confusion and resentment, because such questions are inevitably heard as sarcastic and sometimes mean-spirited.”

Sometimes we can ask questions that are simply accusations or assumptions wrapped up in the garb of a question. Leading questions, however, are not questions at all. When another person gets the sense that we aren’t interested in hearing their thoughts, the conversation is on the fast track to shutting down.

“Sometimes we can feel trapped between the belief that we should stand up for ourselves and a hidden feeling that we don’t deserve to be heard, that we’re not entitled.”

Here the authors discuss a duality; on one hand, people may feel the need to be assertive, and on the other they may feel insecure and unworthy of being listened to. The latter is the result of previous experiences, sometimes even from childhood; they need to be confronted and resolved if one is to be an effective communicator. Making oneself heard and understood is crucial to the dialogue process.

“A better approach is to make the subject clear and discussable by stating your thoughts straight out, while also indicating, honestly, that you are interested in whether the other person sees the situation differently and, if so, how.”

Nobody wins when the people involved in a conversation are not clear. It’s human nature to dance around sensitive topics, but this is destructive to honest and open dialogue that aims to make progress and solve problems. Only by being clear and explicit can we hope to satisfactorily express ourselves and receive real feedback.

“When the other person heads in a destructive direction, reframing puts the conversation back on course. It allows you to translate unhelpful statements into helpful ones.”

When engaged in conversation, someone needs to make sure the conversation is led in a proper direction. If it is allowed to meander and get off-track, the chance of it attaining its goal is slim. However, if the final goal of the conversation is kept in sight, consistently reframing the conversation in helpful terms will allow it to stay within defined terms and approach its goal.

“Most difficult conversations are not, in actuality, a single conversation. They are a series of exchanges and explorations that happen over time.”

With our desire to resolve problems quickly, we assume that we’ll be able to achieve our aims in a single go. Many times this is unrealistic. More likely we need to hold a number of conversations over a period of hours or days in order to adequately deal with a host of issues and anxieties. Nothing is worse that allowing a difficult conversation to go half-finished.

“The need to understand the basis of the other person’s story intensifies when the disagreement is about interpretations and judgments—about what the facts mean.”

On the one hand, it is difficult to find the means and time to agree on the facts. Even more difficult is establishing the proper interpretation of the facts once they can be agreed upon in the first place. Interpreting the meaning of words and events can be difficult, but it is worth taking the time to wrestle over.

“Being clear that something matters to you, and why, has an impact on the other person. It may or may not persuade them—that will depend on the strength of your argument and competing considerations—but it will have an impact.”

The expression of our motivations and intentions is crucial not just to the situation and conversation, but to our own sense of identity. We need to make sure that nothing is left hidden and bottled up; even if our expressions fail to persuade the other person to take our side, at the very least our story will be heard and acknowledged, resulting in mutual empathy and sensitivity.