How to Have a Difficult Conversation

Phone message to John from his Department Head: “I’m sorry John, but you will have to teach our new capstone course next semester.  I know it’s a new course and you had another course you wanted to teach but look at it as a career enhancing opportunity.  I know I can count on you.”

Two ladies having a difficult conversation“Mary’s performance evaluation is down again this quarter.  I have to tell her she’s at risk of being fired.  I hate this part of being a supervisor.”

“I really deserve getting more recognition for my contributions in this grant project.  I need to talk to the other researchers about being listed last in the authorship.”

“We need to talk to our neighbor.  I’ve had it with him borrowing our gardening tools and not returning then.”

What Makes a Difficult Conversation?

The above conversations are fictitious, but they relate different types of pending difficult conversations. So, what makes some conversations so much more difficult than others?  One thing they have in common is a sense of negativity and emotional distress. Fear, worry of being disappointed or rejected, feeling hurt, embarrassed, or afraid of not controlling your anger are at the heart of many of these conversation. They also project an unknown outcome which creates a sense of feeling not in control of what will happen. Digging a little deeper and we find that difficult conversations conjure up underlying identity questions. What does this conflict say about me? I am good enough or worthy? How do others see me?

Compounding any conflict is the risk that the same situation will be seen differently by the people involved.  They will likely have different interpretations, perspectives, and motivations.  Take the example above about talking with the neighbor who borrows tools without returning them.  The neighbor’s perception is that he has permission to use the garden tools until the end of the week when his garden is planted and then intends to return them.  On the other hand, the homeowner expected to loan the tools to the neighbor only overnight.  Many difficult conversations begin with an unstated expectation that will derail the situation later.  Those expectations and interpretations form our perceptions of an event and that becomes reality.  The problem is that we form perceptions through limited vision.  Consider describing a living room in a house by looking at it through an outside window.  You see a chair, a coffee table with a book on it, and a lamp beside it.  You naturally form a perception that the person living in this house likes to read and could be intelligent.  However, someone else looking through another window sees a couch, big-screen TV, and popcorn dropped on the floor.  That person forms the perception of the homeowner being a lazy couch potato and a slob.  Of course, neither one of these perspectives may be correct, but they match what we expect to believe.  This leads to false assumptions and mistaken intentions.

Recognizing the pitfalls of difficult conversations sets the stage for surviving them.  Here are steps to take to make these discussions more manageable.  

Before the Conversation

Recognize your assumptions. 

Before starting a difficult conversation treat assumptions as questions and intentions as guesswork.  When facing a potentially difficult encounter, what assumptions are you making about the other person and the issue at hand?  Are these assumptions be based on facts or inferences?  Could there be other facts you are not aware of that may discredit these assumptions?  The same is true for another’s intentions.  We can only guess at their intentions based on what how they act and what we see.  But their actions may be motivated by factors we cannot see. 

Label your emotions. 

What specific fears creep up when you think about having that dreaded conversation with your department head, ex-spouse, or unruly neighbor?  Naming these fears and other emotions can take some of the sting out of them by making them transparent and not lurking underneath our thoughts.  Counter these fears with listing the benefits of this conversation.  Conversely, what would be the potential costs of not having this conversation?

Identify your goal and how to express it.

What is the core result you would like to achieve?  How can you say this clearly and concisely?  Instead of drafting a speech which can be derailed, jot down key words that relate to what you want to say.  Identify the core issue or central problem.  What is your preferred outcome?  Because the other party has their own agenda, look for possible alternatives or modified solutions prior to the meeting. 

Put yourself in their shoes.

What might be the other party’s agenda?  What needs do they have to fulfill?  Based on the challenges they face, how would they react to your request?  Can you address their needs? 

Set up the meeting

Ask the other party for a meeting.  When setting up the meeting, include the topic to be discussed.  If the nature of the conservation is troubling to you, it is likely to be difficult for the other party as well.  By giving them a chance to prepare, necessary information can be gathered in advance, thus saving time.  Blindsiding the other party is a good way to sabotage the meeting from the beginning. 

Practice stress management.

Take care of yourself well before the meeting by eating healthy and getting adequate sleep.  Learn relaxation and stress management techniques that work for you.  A quick universal technique is tactical breathing used by military personnel before they enter a dangerous mission. The technique only takes a couple of minutes.  Take a slow intake of breath for 5 seconds, hold it for 5 seconds, and slowly release it for another 5 seconds.  Repeat 3 or 4 times.  Prior to going into the meeting, practice this technique.  For better more long-lasting effects, practice tactical breathing 2 or 3 times a day as a regular stress management tool. 

Conducting the Conversation

Open with your perspective of the issue.

Thank the person for meeting with you to set the stage for a respectful encounter.  Then share your viewpoint and where your conclusions came from.  Be direct, respectful, and concise.  Stick to the facts as you know them.  If you need to give your opinion, state that this is your opinion based on the information (or assumptions) you have.  Interpersonal relationships are at stake in almost all difficult conversations, so sometimes it may be beneficial to acknowledge underlying emotions.  A good way of expressing your opinion and emotion is to say,

 “When you _______, I feel ___________.”  Or, “I get a sense of ____ when ____ happens.”

Contrasted with a statement like, “You always _________,” or “You never __________,” or “Why can’t you ____,” which feels like an attack and shuts down the conversation.  The “I feel” message is less threatening and opens the door to further dialogue.  It also allows for correcting misunderstanding or false perceptions. 

Ask how they see it.

To reduce misunderstandings, ask how they see things differently.  What is important about this situation to them?  If they seem confused or annoyed, ask if you have done something to upset them or mislead them.  Give them permission to contradict your view of the situation.  Likewise, respect their view whether you agree with it or not.  It belongs to them and shows how they see the issue, which is good for you to know.  Acknowledge their feelings if they express them.  It may surprise you how they feel the way they do. 

Finally, show them that you were listening by briefly summarizing what you heard them say.  If they correct your summary, good. It clarifies their point of view or corrects an assumption you may have had. Occasionally paraphrasing what you heard leads to better understanding and rapport building.  The other party wants to be heard just as much as you want them to listen to you. 

Expanding the Conversation

Provide your proposal.

After listening to the other party’s viewpoints, provide your position on how to resolve this issue.  It may be the same as you initially made prior to the meeting or may be modified after learning their perceptions.  If there are options, be prepared to negotiate. 

Problem Solve.

If the issue is unresolved, ask how we can move forward from here. Acknowledge their position or accept their uncertainty of how to proceed. Offer alternatives and seek options. Ask yourself if you have considered their needs in your proposal.  Explore how their needs and interests can be fitted into your proposal.  When your viewpoint and their viewpoint are combined, a big picture emerges.  Keep the big picture in mind when negotiating.  Whenever you are at a loss of what to say, summarize what you have just heard and then ask them their opinion.  Listen intently and follow up with open ended questions that cannot be answered with a simple yes or no. 

Concluding the Conversation


Shaking HandsSummarize what was decided and what will happen in the future. Who will do what to settle the issue?  If the issue is still unresolved, look at the progress that was made and can be implemented. Decide if another meeting is appropriate or what other avenues you can take. Regardless of the outcome, thank them for talking with you.  After leaving the meeting, review what you learned from this experience.  What would you do the same or differently in a similar situation?  Now that it is over, take a deep breath and relax.  Finally, congratulate yourself on going out of your comfort zone and confronting a difficult conversation.


Difficult Conversations (1999) by Douglas Stone, Bruce Patton, & Sheila Heen

How to handle difficult conversations at work (January 2015). Harvard Business Review, by Rebecca Knight

How to have difficult conversations when you don’t like conflict (May 2017). Harvard Business Review, by Joel Garfinkle