How to Set the Stage for a Difficult Conversation

Published: Jan 24, 2019
Modified: Mar 25, 2020

By David Lee

What you do before you talk with someone about a difficult issue will largely determine what happens during the conversation. How you spend your “thought time” prior to talking with that person has a huge impact on the other “make or break” moment of truth—how the conversation begins. If you spend your time thinking about the other person’s evil intentions—real or imagined—and getting outraged, if you spend your time ruminating about unpleasant things he or she has done or unpleasant conversations you’ve had with him or her, you’re likely to enter the conversation in a negative emotional state and with an antagonistic attitude. Doing so obviously reduces the odds that you will begin the conversation in a skillful, productive manner.

Questions to Ask Yourself as You Think about the Other Person and the Upcoming Conversation

  1. Are you mind reading? Mind reading is when we take our guesses about a person’s motivation, agenda, or intention as the truth— and then take action based on our assumptions. Since we can’t know what’s going on in another’s mind, our guesses are just that and nothing more—guesses, not facts. When we assume our guesses are facts, we can set ourselves up for unnecessary conflict by going into the conversation with a combative, antagonistic mind-set that might be based on a totally incorrect perception.
  2. Are you fortune telling? Fortune telling is a cousin of mind reading. Instead of taking our analysis of a person as fact, fortune telling is taking our predictions of what will happen as fact (e.g. “I know exactly what she’s going to say,” “I know what will happen if I bring that up.”) Just as with mind reading, fortune telling can set us up for unnecessary conflict by leading us to enter the conversation in a confrontational mood.
  3. Are you indulging in self-righteous outrage? Often mind reading and fortune telling lead to self-righteous indignation (“She’s doing that just to be passive-aggressive! I am so tired of her game-playing! I don’t have time for this!”) Self-righteous outrage puts us into an angry, resentful emotional state, hardly an optimal frame of mind to engage someone in a productive conversation.
  4. What’s your goal? Asking ourselves about our goal, what we hope the conversation will accomplish, helps us identify and eliminate unproductive, antagonism-generating agendas. If our goal is to tell someone off, show him why he's wrong, or other win/lose agendas, we set the stage for an antagonistic interaction. To help you identify possible unproductive intentions, ask yourself if your goal is to tell him off and set him straight, or to understand his perspective and help him understand yours.
  5. Are you willing to hear an alternative perspective and maybe find out your perspective is off base? Although it may feel good to see ourselves as right or blameless, if it makes us unwilling to get potentially useful input and feedback, it's an expensive indulgence. A clue to how sincere we are about engaging in a constructive conversation is whether we are willing to get a third party’s perspective—even if it ends up being very different from ours.

Actions to Take

  1. Focus on trying to understand the other person’s perspective.  “Seek first to understand” is the antidote to mind reading, fortune telling, and indulging in self-righteous outrage. By devoting part of your preparation time on seeking first to understand, you’re more likely to generate a balanced, reasonable perspective. Seeking to understand is different from mind reading. When we seek to understand, we recognize that our assessment is still an opinion, not a fact.
  2. If you’re really upset, vent to someone you trust—or several if necessary—until the emotional charge has been reduced to a controllable level. Doing this allows you to calm down enough to get into a more moderate emotional state and thus allows you to see the situation from a more rational, untainted perspective. Having “blown off some steam,” you are more capable of entering the conversation in a neutral or even positive emotional state. Keep in mind that the goal of venting is not to disparage the other person and make him look bad. It’s to discharge negative emotions––not build more. If we vent in a mean-spirited way, putting down the other person, and consciously trying to make him look bad, we only create more negative emotions in ourselves, which hurts us physiologically and hurts our chances of a having a constructive conversation.
  3. Ask someone you trust and respect for his or her perspective. When we’re upset, our emotions can distort our perceptions. We can remedy this by getting someone else’s perspective. Because that individual is not emotionally involved, he or she is able to see the situation in a more measured, rational way. If you do ask for someone’s perspective, make sure you really want it. We can measure how sincere we are about wanting to perceive the situation accurately—rather than indulge ourselves in self-righteous indignation—by our willingness to hear a neutral party’s perspective, even if it’s different from ours.
  4. Ask for feedback on how you propose to bring up the conversation. Ask one or more people whom you respect and trust how they would respond if you brought up the issue to them in the way you’re thinking of doing. Give them some background about yourself and the other person and ask them how they think the other person might respond to your opening.
  5. If appropriate and possible, establish some goodwill with the other person by doing something kind, generous, or thoughtful. When there’s goodwill between two people, they’re more likely to give each other the benefit of the doubt. They’re more likely to enter a difficult discussion with a willingness to hear the other person’s point of view, and they’re more likely to want to work things out collaboratively. Establishing goodwill can be as simple as paying the person a sincere compliment, doing him a favor or offering to help him out rather than waiting for him to ask you.
  6. If appropriate and possible, see if you can engage the person in one or more positive interactions before addressing difficult issues.  Besides making deposits in your “goodwill bank account with the other person,” think about other ways of engaging him in positive interactions. Again, such interactions don’t have to be big or dramatic. In fact, the simpler and more understated, the more likely he will be receive the gesture as genuine. It can be a short conversation about his favorite team or asking him about his kids. By taking the time to have positive interactions with him, you increase the odds he’ll enter the important conversation in a more positive emotional and attitudinal state.

    Returning to the point about your actions being perceived as genuine, make sure they truly are genuine. If you do a favor or make small talk purely as a strategy for “warming the person up” so you can have a productive conversation, he's’ likely to pick up on your insincerity. If you don’t yet sincerely want to understand and respect their point of view or you harbor strong negative feelings toward them, your first task is to do the work that will get you into a more charitable frame of mind

    If we don’t do that work first, engaging the other person in a positive interaction will be nothing more than a calculated manipulation. When we no longer see the person as an enemy or out to get us, when we sincerely do want to bridge the gap, our efforts to create positive interactions will be sincere and genuine, and the other person will pick up on that.
  7. If you catch yourself mind reading, fortune telling, or indulging in self-righteous indignation, stop. Remind yourself that mind reading and fortune telling are irrational thought processes Even if your guesses are dead on, even if you have a right to be outraged, you’re the one who pays the price, as mentioned previously.
  8. Make the Law of Reciprocity your ally. People tend to reciprocate. If we’re generous, the other person is more likely to be generous toward us. If the person you need to talk with believes you’re trying to show him he's wrong, he’ll reciprocate by trying to show you that you’re wrong. If you genuinely want to understand his point of view, he's more likely to want to understand yours. Keep this principle in mind by reminding yourself that “what you put out is what you get back.”

About the Author(s)

David Lee is the founder of and an internationally recognized authority on optimizing employee performance.  He is the author of Managing Employee Stress and Safety as well as dozens of articles.