Attitudes and Skills for Having Difficult Conversations More Effectively

By Jay Einhorn, © 2013

We all need to be able to have difficult conversations effectively, and there are attitudes and skills that can help us do that. Here’s a summary I wrote, with a pitch at the end for consulting and training work.

Executive Summary

Communication fads come and go, but difficult conversations are here to stay, so information that helps us to have them more productively is welcome. The books, “Difficult Conversations,” and “Crucial Conversations” describe a number of ideas, attitudes and skills to help. I’m using key ideas, mainly from “Difficult Conversations,” in my consultation and therapy, and recommend the book. “Crucial Conversations” looks at the same territory in a somewhat different way, with one very important difference. I introduce ideas from both books, together with information from other sources, in my consultation, training and therapy.

Learning a concept doesn’t necessarily mean knowing it deeply enough to apply it, and there’s a tendency to revert to old habits and “them and us” attitudes in actual situations. So, in addition to presenting the information, I recommend supporting depth learning through experiential methods, including discussion of cases, role playing, and ongoing focus on the issue through a focus on pre- and post- difficult conversation work.

We All Have Difficult Conversations

Communication fads come and go–there’s a new one every few years in the worlds of human relations, education and organizational training–but difficult conversations have always been with us, and always will be. As a student of human nature, a therapist, diagnostician, consulting psychologist, administrator, and–of course–as a person living in this world, I have been in and around many difficult conversations!

Four impressions have become clear:

1. Many difficult conversations that go badly don’t need to be had at all. They occur because of a misunderstanding that could have been cleared up through simple inquiry, or because people acted on feelings and assumptions that they should have taken time and effort to understand and manage rather than “letting them out the door” prematurely.

2. Many difficult conversations that must be had are avoided, because the people who need to initiate and manage them don’t know how to. The result is that bad consequences are allowed to happen because no one is dealing with a problem that needs to be dealt with.

3. When difficult conversations are necessary, there are attitudes and skills that can help them to go better. Potential damage can be avoided or minimized, and relationships preserved and even improved. The participants in the conversation can learn things they need to learn. Such conversations can even be healing.

4. When difficult conversations happen without the necessary attitudes and skill, they can be counterproductive. Relationships can be damaged, people can be hurt–there can be “too much heat and not enough light,” in one of my favorite phrases–necessary learning won’t happen, and the consequences can be injurious to the people having them and their families, organizations, communities, and societies.

The book “Difficult Conversations,” by Douglas Stone, Bruce Patton, and Sheila Heen, of the Harvard Negotiation Project, takes an in-depth look at how difficult conversations can go wrong, and describes a set of ideas, attitudes and skills to support having the necessary difficult conversations of life more effectively and productively ( I’ve found it useful in my work in individual and couples therapy and organizational consultation and training.

Some Key Ideas From “Difficult Conversations”

1. Shift from a Conflict Conversation to a “Learning Conversation”

The purpose of applying “Difficult Conversations” methods is to move difficult conversations from being antagonistic or adversarial conversations, in which people are attacking and defending or trying to achieve goals through power or manipulation, to being learning conversations in which both parties are listening to one another as well as saying what they need to say.

2. The “Three Conversations:”

A key idea in “Difficult Conversations: is that every difficult conversation is really three conversations:

1. The “What Happened” conversation, consisting of “3 stories,”

2. The “Feelings” conversation, and

3. The “Identity” conversation.

3. What Happened: The Three Stories

There are three stories about “what happened” in every difficult conversation: each party’s story or narrative of events, and the “third story.” The “third story” is the story which might be told by an impartial third party, such as a mediator, which includes elements of each party’s story without casting any blame.

For example, in a school situation, a parent and teacher might need to have a difficult conversation about a child’s failure to complete his homework.

Let’s say that Johnny, a fifth grader, has stopped handing in his homework and is falling behind in class. The teacher’s story is that she is sending homework home with Johnny but his parents are not following through to make sure that he does it. Johnny’s parents both have demanding jobs and the teacher thinks that they are just too drained when they get home to have the energy to do the difficult work of making Johnny do homework, especially if he doesn’t want to do it. She also thinks Johnny’s parents might feel guilty about spending so much time away from home at work, so they might be overly permissive and allow him to avoid homework.

Johnny’s parents’ story, on the other hand, is that Johnny is being bullied by a bunch of kids at school, and he’s hurt, sad and angry about it, so he doesn’t want to even think about school once he’s out of there. So that’s why they think Johnny isn’t doing his homework. And they think his teacher is either accepting other students bullying him as normal behavior and letting it happen, or else that she is just too careless to even notice that it’s happening.

The “third story” is that Johnny is not doing his homework and falling behind in school, so now his teacher and parents need to look at this together to try to understand why he’s falling behind and see how they can work together to help him get back on track.

The “Difficult Conversations” authors suggest starting a difficult conversation with the “third story.” Johnny’s teacher might do that at the beginning of her meeting with his parents, to start the conversation on a good foundation that she can “reframe” back to if the conversation is in danger of becoming undermined or blown up as it progresses.

4. The “Feelings Conversation”

According to “Difficult Conversations,” every difficult conversation is powered by feelings, which are often not acknowledged. It can be very important to acknowledge these feelings without letting them undermine the conversation. For example, Johnny’s parents may feel angry about Johnny’s being bullied at school, helpless to do anything about it, and let down by his teacher. His teacher may feel let down by Johnny’s parents, and unfairly blamed. It’s important for both parties to acknowledge and respect one another’s feelings, while not letting them derail the conversation. If someone becomes too upset, taking a time out and returning to the conversation in a few minutes, or even rescheduling it to another day, can help to keep it on track.

5. “Reframing”

Reframing is one of the most important “Difficult Conversations” skills. If Johnny’s parents accuse his teacher of not caring about him, she could allow the conversation to get blown off course, by reacting defensively or counterattacking, or she could reframe the conversation by interpreting their comment as an expression of their concern, emphasizing that she is concerned too–that’s why she called the meeting–and getting the conversation back on track.

6. The “Identity Conversation”

The “identity conversation” could be described as the stake that each person’s ego or self has in their personal or professional role in the conversation. For example, if Johnny’s parents accuse his teacher of not caring about Johnny, they are attacking her identity as a teacher. If she then gets stuck in defending herself–”of course I care about him, I’ve been a teaching for a dozen years and I care about every one of my students!”–or gets too upset to remember her agenda for the meeting and keep managing her role as facilitator, the conversation is likely to become useless or counterproductive. And of course the same thing could happen if she counterattacks Johnny’s parents with: “If you cared about him you’d make sure he got his homework done!”

7. Reframe From Blame to Contribution

The “Difficult Conversations” authors regard the establishment of blame as not a useful strategy. Instead, they assert, it’s more useful to think in terms of the relative contribution of each party. In our example, it doesn’t really help anyone for Johnny’s parents blame his teacher or his teacher to blames his parents. But if, as a result of the difficult conversation, Johnny’s parents and teacher can have a learning conversation, the teacher might realize that she’s contributed to the problem by not being aware that Johnny was feeling picked on, and his parents might realize that they’ve contributed by not taking a firmer position with Johnny about doing his homework regardless of how he felt about his day at school.

8. Avoid “Intention Invention”

By “intention invention,” the authors mean that we make up reasons about why we think someone we’re in a conflict with is doing whatever they’re doing, when in fact we don’t really know why they’re doing it.

“Intention Invention” reminds me of two rather complicated ideas, which I’ll mention without going into in depth: “attribution” in cognitive psychology, and “projective identification” in psychoanalytic psychology. I’ve described how these ideas relate to intention invention in my blog,

The “Difficult Conversation” authors emphasize that most of what we do has multiple motivational sources. In our school example, Johnny may be falling behind in his homework partly because he’s being picked on, partly because he feels the teacher doesn’t like him, partly because he finds the work difficult and would rather avoid it, partly because there are more enjoyable activities for him to do after school, and partly because he can get his parents to let him; which then makes him feel special and able to control the events in his life, at least at home. His teacher and parents will have similar multiple motivations contributing to their own perceptions, feelings, and attributions. So it’s generally a mistake to think that someone we’re in a conflict with is doing whatever they’re doing for only one reason,; or that we ourselves are. We are almost always operating on the basis of a mixture of motivations.

“Intention invention” is a modern version of the old saying, “Give a dog a bad name and hang it.”

9. Authentic Listening

Authentic listening is a key skill in any difficult conversation. Everyone knows that you’re supposed to listen, but people often just go through the motions of listening, and sooner or later the other person usually gets this.

The Difficult Conversations authors don’t assume equal motivation on the part of both parties at the beginning of the conversation. Whichever party is taking the responsibility to facilitate the difficult conversation has to be ready to authentically listen to what the other party has to say. The purpose of listening is not to defeat the other person in argument, or manipulate them, or wear them out. I would say that authentic listening leads to existential engagement, and that often makes a difference in difficult conversations, because people often know intuitively when someone is, or isn’t, really engaging with them.

“Crucial Conversations” and Truth

Another book that provides insight, attitudes and skills for having difficult conversations effectively is “Crucial Conversations: Tools for Talking When the Stakes Are High,” by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler ( “Crucial Conversations” provides ideas such as “Speaking Persuasively, Not Abrasively” and “Making It Safe” in a conversation, and many others, covering much of the same territory as “Difficult Conversations,” in another way. But one key difference between “Crucial Conversations” and “Difficult Conversations” is in the attitude toward truth.

“Difficult Conversations,” holds that each person has their own truth, but there isn’t necessarily an objective truth per se. “Crucial Conversations,” on the other hand, both sees objective truth as existing in situations, and even sees the goal of conversational skill as to be able to speak the truth about a situation effectively, in a way that doesn’t attack or repel the other person(s) in the conversation, and in a way that they can hear. So, in “Difficult Conversations,” there’s my truth, and your truth, and we have to work it out. In “Crucial Conversations,” there’s the truth, and we have to be able to acknowledge it together.

I believe that there is an objective truth in all situations, but that it’s more important to some difficult conversations than others to acknowledge it explicitly. A related issue is how much truth needs to be acknowledged in a difficult conversation in order for progress to be made. There is, after all, always more truth than we can perceive or absorb at any given time. This has led me to coin the phrase, “the minimum necessary truth.” That means that, in any situation, there is a minimum necessary truth which must be acknowledged by all parties if things are to be made better.

“Them and Us:” Arthur Deikman

Psychiatrist Arthur Deikman ( makes an important contribution in his book, “Them and Us: Cult Thinking and the Terrorist Threat” ( Deikman discusses the effect of propaganda and how cult-like thinking can foster the illusion of debate of issues rather than genuine consideration. “In most conflict situations, disagreements are based on differences in interpretation and in the priorities given to different values, but these differences are seldom stated, and, lacking that clarification, we absorb highly selective information, are swayed to one side or the other, but end up no wiser…opposing propagandas do not assist the democratic process but produce partisans, each with the mind-set of a cult member…” It’s easy to see how the same attitudes undermine the necessary difficult conversations of life, when the participants try to win (however they define that) rather than have an actual conversation.

Deikman indicates four areas that can usefully be clarified in the discussion of a controversial problem:

“1. The key data. (Are they disputed?)

2. Interpretations of the data.

3. Value conflicts. (Reason for giving one value priority over the other?)

4. Error indicators. (What events or facts would indicate to each side that their belief or strategy should be changed?)”

Clearly these ideas, and the attitudes underlying them, can usefully be included in many difficult conversations.

Application: From Passive to Active Understanding

The attitudes and skills for having difficult conversations more successfully are not easy for most of us to acquire and use. We generally don’t learn them through our professional education, or even our moral, religious, or spiritual education. Doing difficult conversations well requires an enormous amount of cognitive executive functioning–that is, staying on task, not taking criticisms and attacks too personally, continually monitoring the conversation and reframing as necessary.

Psychologists distinguish between different forms of learning, such as semantic and procedural. It’s one thing to know the key ideas about how to have difficult conversations more effectively so that one can define them or answer multiple choice questions about them. It’s entirely another thing to know them deeply enough to apply them in actual situations. In my work with individuals, couples and groups, I’ve often found that people who seem to understand them pretty well when I discuss them, or present them in lecture and Powerpoint, often revert instantly to a “them and us” attitude when applying them in discussion of cases or role playing exercises.

Surely, there are different levels or ways of knowing, and it’s part of human nature that we know information that we don’t apply. One of my favorite teaching stories is about Ibrahim Ben Adhem, a prince who, like the Buddha, left his royal home to seek knowledge. As he was walking down the road he came across a stone on which was written: “Turn me over and read.” Turning the stone over, Ben Adhem read: “Why do you seek more knowledge when you pay no heed to what you already know?” (Retold by Idries Shah in his Caravan of Dreams, within the narrative, “Encounter At A Hermitage.” See listing at

There are multiple levels of depth to that story! We often find, as we look back on our mistakes, that we knew better than to do whatever we did. We may have had some sort of inkling that we failed to heed at the time, or maybe there was a principle that we ignored because we wanted to see the situation in some other way than it really was. In psychotherapy and consultation, I often contribute more by helping my clients clarify and apply what they already know, than by introducing new information; though some new information may be necessary to help them understand and use what they already know, like the “stone,” and some effort, like “turning it over.”

Emphasizing the difference between different kinds of learning, British educational psychologist Lawrence Stenhouse, in his, “Introduction to Curriculum Research and Development,” distinguished between “information,” by which he meant what we know passively (for example what we can define on a multiple choice test) and “knowledge,” by which he meant understanding that we can apply in situations in which the correct response can’t be pre-specified. ( American psychologist Robert Ornstein, in his “Mindreal” (, refers to his research on both halves of the brain in discussing how the left hemisphere is more involved in understanding words as such, but the right hemisphere is more involved in interpreting what they really mean.

This is why experiential learning is so important when it comes to learning difficult conversation skills (and many other relationship skills!). Discussion of actual case situations, and role playing of actual and simulated situations helps to bring home the meaning of attitudes and skills for difficult conversations. Even participants who just watch can potentially benefit from watching others actually engaged, as cats who watched other cats learn a maze were able to learn it more quickly later than cats who hadn’t.

Accordingly, there are several ways that I’ve been involved in helping people to learn skills for having difficult conversations more effectively:

1. An information presentation of basic ideas, attitudes and skills for having difficult conversations more successfully. This happens on a discussion basis in individual and couples therapy, and is supported by Powerpoint and handouts in group training.

2. Consultation reviewing case studies involving discussion of actual difficult conversations.

3. Experiential learning through role playing.

4. Ongoing consultation and training, including pre-planning before difficult conversations and debriefing afterward, extending over a series of consultations.

5. Actual involvement as a consultant-participant-facilitator in difficult conversations, optimally also including pre-planning and debriefing.

Even with training, we all learn in our own way and at our own pace, and sometimes we have to have experiences after training for the training we’ve received to actually make sense. But we’re all going to be involved in difficult conversations, so it’s important that we learn attitudes and skills that support having them more effectively. Knowing and using a more productive approach can make a great deal of difference, again and again.

(note: I want to emphasize that I haven’t met the authors of “Difficult Conversations,” haven’t received training from them or their colleagues, and am not an “official vendor” of “Difficult Conversations” training. I’ve been interested in helping people develop attitudes and skills for having difficult conversations and resolving conflicts more successfully for a long time, and “Difficult Conversations” is a valuable resource, as are the other sources mentioned.)