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Difficult Conversations: How to Discuss What Matters Most


Getting along with others is the biggest challenge of our human existence.  Sure, there are easy conversations – but there are difficult ones, too.  Difficult Conversations: How to Discuss What Matters Most is a guidebook for walking through the conversations that matter.  It comes as a long line of writings from the Harvard Negotiation Project.  The most popular book to come from this work is Getting to Yes.  Douglas Stone and Sheila Heen also wrote Thanks for the Feedback, which describes how people can learn to accept feedback better.  This work is about how to give feedback and have the hard conversations.

It’s important to note that others have tackled this difficult problem as well.  For instance, Crucial Conversations and Radical Candor take different approaches to these same hard conversations.

Three Parts

There are three critical parts to any difficult conversation.  They are:

  1. What Happened?
  2. What Was Felt?
  3. What Does This Mean?

These are fundamentally the same feeling, meaning, and power that Bill Issacs speaks about in Dialogue, which builds on David Kantor’s work discussed in Reading the Room.  The different framing is that, here, the focus is on the parts of the conversation that are needed rather than the perspectives that someone can take in the middle of a conversation (or dialogue).

While the process starts with what happened, it’s possible that this is the least useful aspect of the conversation.  While it sets framing, it is almost never what the difficult conversation is about.  Difficult conversations aren’t about the facts.  They’re about the perceptions, interpretations, and values.

That’s where we move into the land of feelings, or affect.  The goal is to understand and validate everyone’s feelings.  There are no wrong feelings, though there are some wrong behaviors.  We must accept that people feel they way they feel for good reasons – even if we don’t understand it.

The third part is understanding the meaning to our relationship.  It can be something as simple as wanting to be heard or to create awareness or something more concrete and tangible.

Battles and Learning

Often people get into battles about what the facts of the situation are.  One person sees something from one direction and the next person sees it differently.  Instead of accepting both perspectives, an argument ensues to determine objective truth and reality.  This locks horns and prevents the conversation from progressing towards learning.  Learning conversations are fundamentally based on the desire to understand the other person’s experience – not to agree with it.

The key perspective change is for everyone to get curious.  When we move to a learning perspective and step aside from the need to agree, we can learn more about the other person and their perspective in a way that allows for greater unity – and better relationships going forward.  If we can’t get curious about the other person’s perspective, we may find it hard to get to any kind of a resolution.

Three Reasons

Difficult Conversations proposes there are three reasons for disagreement:

  1. Different information
  2. Different interpretations
  3. Self-interest

For years, we’ve been teaching conflict resolution, and we simplify this into two simple reasons:

  1. Perspective
  2. Values

We believe that perspective is inclusive of our information but encompasses the deeper meaning that we’ve assigned through our experiences.  We further believe that it’s values that drive our interpretations – primarily of the meaning.  We believe that self-interest is encapsulated in the concept of values.

We find that we can generally quickly identify what’s different in perspectives.  Values are harder to understand.  Using frameworks like Reiss’ 16 basic motivators from Who Am I? and Jonathan Haidt’s foundations of morality as explored in The Righteous Mind, we can generally identify the value systems that cause people to reach different conclusions.

Lack of Faith Leaps

Daniel Kahneman explains in Thinking, Fast and Slow that we’ve got a fundamental attribution error, which causes us to assign someone else’s behaviors to their character rather than the circumstances.  However, our leaps don’t stop there.  Chris Argyris developed a ladder of inference, and it’s how we infer things that aren’t in the conversation.  (See Choice Theory for more.)  It’s this process that moves us from bad intentions to bad character and, ultimately, condemning people as though they had wronged us.  We develop stigmas on irrelevant details in an attempt to protect ourselves.  (See Stigma for more on stigma, and Leadership and Self-Deception for more about protecting ourselves.)

Intention Switchtrack

In Thanks for the Feedback, Stone and Heen explain that a switchtrack is where one topic in a conversation suddenly becomes two, as someone introduces a second topic to the conversation – generally unintentionally.  This can happen when someone is expressing their feelings and the other person responds with their intent without acknowledging or reflecting the understanding of what the other person is saying.  In an ideal world, listeners would share an Effective Apology before sharing more context in the form of their intentions.

The problem is that the intent of the person may be of little solace.  Certainly, people feel the way they feel – regardless of the others’ intentions.  It’s also possible that the consequences of the interaction may mean that there’s a real problem to be solved – regardless of the intentions.  That isn’t to say that you should never share intentions.  It’s a good part of an effective apology when coupled with proposed actions to prevent further harm.  However, there are times when the practicalities may be more important.

The Blame Game

We’ve all been in the meeting where the question gets asked bluntly: “Whose fault is this?” or “Who is to blame?”  The problem, in addition to being unhelpful for moving things forward, is it focuses on the person or people who caused the problem.  In our complex world, there’s rarely one cause.  (See Focused, Fast, and Flexible and Cynefin.)  It’s more about contributions than cause.

It contains the implicit judgement that something or someone isn’t up to the standards of conduct.  It implies that some moral or societal code has been broken when this is rarely the case.  Finally, it implies the need for punishment if there has been a breach.  This may – or may not – be the case.

A better approach is to speak about the contributions that people have made to the problem.  It recognizes that many things are interacting systems.  (See Thinking in Systems.)  It’s only through the interaction of the system that the results were achieved.  If we change any variable in the system, we have the possibility to get different outcomes – without the need to identify that someone did anything wrong.

The blame game is a waste of time.  It doesn’t really work to get to the root of a problem, because there’s no psychological safety – and there’s no help in going forward.  (See The Fearless Organization and Right Kind of Wrong for more on psychological safety.)

Contribution to Trauma

In my post Trust => Vulnerability => Intimacy, I teased out the concept of making choices that lead to bad outcomes as compared to appropriate vulnerability.  The challenge with having conversations with people where trauma is involved is that it may not be possible to separate the sense of blame from the sense of contribution to the situation.  It may be that the person takes on too much responsibility – or not enough.

While it’s certainly not appropriate to “blame the victim,” that may be what someone hears when you’re trying to sort out contribution to a problem when trauma is involved.  (See Becoming Trauma Informed and People in Crisis for more about the tendency to “blame the victim.”)

Focused on the Wrong Thing

It’s a tragedy.  Kids are jumping out of windows and dying.  The cry goes out that we need to address the problem.  People are mobilized and inquiries are started.  Progress continues trying to convince kids to not jump out of the windows, until someone finally realizes that they’re jumping out of the windows because the building is on fire.  The negative outcome has us focused on the last step instead of looking at the broader factors and the bigger picture.

This myopic view prevents us from working backwards along the causal chain to discover what people really want (freedom from the fire) instead of the ends they achieve (a fatal fall).  (See Collaboration and Moral Disengagement for more on means vs. ends.)

Negotiating our Feelings

Most people believe there’s a great difference between their feelings and their thoughts, but neurologically speaking, they look identical.  When being scanned there’s no way to separate a thought from an emotion.  (See Feeling Good.)  While emotional reasoning can be bad – that is, allowing our emotions to determine whether something is good or not – negotiating with our feelings can be powerful.  (See How Good People Make Tough Choices and Moral Disengagement for the ethical implications.)

Cognitive behavioral therapy (CBT) is one of the most widely validated approaches to psychological treatment, and it’s fundamentally based on the concept that you can use your thoughts to shape your emotions.  We can’t think that our thoughts and feelings don’t influence each other, because they are intertwined.  (See Brief Cognitive-Behavioral Therapy for Suicide Prevention and Cognitive Therapy for Suicidal Patients for more.)


One of the biggest challenges with difficult conversations is the possibility of tripping over some aspect of someone’s identity.  (See Thanks for the Feedback for more.)  It’s difficult to identify how someone sees themselves and their identity, because our identities are multifaceted.  Some of our identities are born into us.  Some identities we choose.  Other identities are imposed upon us by our cultures.

The best intentioned of us can’t escape the chance that we’ll be shaken from our identity.  Consider the story: After observing Ōsensei Morihei Ueshiba, the founder of Aikido, sparring with an accomplished fighter, a young student said to the master, “You never lose your balance. What is your secret?” “You are wrong,” Ōsensei replied. “I am constantly losing my balance. My skill lies in my ability to regain it.”

I’ve frequently shared Richard Moon, an aikido master, saying that it’s not that the great masters never lose their center but rather that they discover it sooner and recover faster.  (See Dialogue: The Art of Thinking Together, Emotional Intelligence 2.0, Resilient, and Reinventing Organizations.)


The most important part of difficult conversations isn’t talking.  The most important part is listening.  The most important part is learning how to listen with curiosity and deferred judgement.  (See Motivational Interviewing, and A Way of Being.)  In the end, if you can listen well, you can handle all Difficult Conversations.