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How to Have Difficult Conversations

Follow these guidelines for challenging encounters and fighting “fair.”

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Most everyone dreads the difficult, challenging conversation. This includes conversations in which we have to deliver unpleasant news, discuss a delicate subject, or talk about something that needs to change or has gone wrong.

Just thinking about having these conversations—whether with one’s partner, children (particularly adolescent or adult children), relatives, friends, or co-workers—can fill you with anxiety and trepidation, taking up space in your mind and distracting you from other important considerations that require your attention.

The anxiety can relate to concerns about bringing up a sensitive issue, being uncomfortable with setting or enforcing limits, or worry about how the other person will react. People may be fearful that the conversation will precipitate bad feelings or conflict. Because these kinds of conversations can create such discomfort, it’s natural and normal to want to avoid having them altogether. The problem with avoidance is that, in the absence of a situation resolving on its own, putting it off only allows it to continue and potentially get worse.

Planning and preparing can help turn down the volume of your apprehension and make it much more likely that the difficult conversations you need to have will be successful. As legendary UCLA basketball coach John Wooden put it, “Failing to prepare is preparing to fail.”


For challenging or difficult topics, it’s best to plan to have the conversation in advance: “I’d like to talk with you about..." or "We really need to talk about..." Then, mutually agree on a time and a place for the conversation, and agree to meet in a place with enough space for all participants to be “comfortable enough” and to see each other clearly.

It’s never helpful to collect and hold on to feelings of frustration, anger, or resentment for days, weeks, or longer, and then dump them on another person all at once. Whenever possible, try to discuss challenging issues as they come up or soon thereafter.

Ground Rules

  • As much as possible, stay at about the same eye level. In other words, it’s best if everyone participating is either seated or standing. It’s generally not helpful for one person to be physically “above” or “below” others.
  • Speak directly to the other person(s).
  • Speak as calmly in a matter-of-fact tone as possible. This maximizes the chances that others will hear the content of your message, rather than fixate on your emotions.
  • Avoid finger-pointing, whether blaming or literally pointing fingers. This tends to make the other person(s) feel that he or she is being lectured or put down.
  • Avoid name-calling, yelling, screaming, cursing, put-downs, insults, or threats (emotional or physical). When any of these happen, the only thing other people hear is anger and attack. As a result, they are likely to leave, shut down, or attack as well. Treating others with respect is essential to healthy communication.
  • In describing your concerns and the things you’d like to happen differently, be as clear as possible and use specific examples. Avoid the words “always,” “never,” “everything,” and “nothing.” These may express your frustration and upset, but they overgeneralize and are fundamentally inaccurate. As part of a communication process, they are unhelpful.
  • No interrupting. When the other person is speaking, consciously listen to what he or she has to say with the intent of hearing it. This is very different from waiting for the other person to finish speaking so you can respond. If you’re thinking about what you’re going to say in response, while he or she is still speaking, you’re not listening.
  • Make sure you understand what the other person has said before you respond. If you’re not sure what he or she said or meant, ask for clarification. “Could you please repeat that?” “I’m not sure what you mean. Can you please help me better understand?”
  • Approach the conversation with openness and an interest in problem solving, rather than needing to be “right.” Anytime we see it as a competition where we need to be “right,” it means the other person has to be “wrong.” This kind of rigid either-or, win-lose, or right-wrong mindset makes conflict much more likely and mutual understanding much less likely.
  • Keep to the topic at hand. Focus on the topic of this conversation. Bringing up issues or complaints related to other topics or past events always interferes with healthy communication during the current conversation. Save those other issues for another time. If they continue to be important to you, you’ll remember them.
  • Do not walk away or leave the conversation without the other person’s agreement. Allow for the possibility of time-outs. It’s important to discuss and mutually agree to the concept of a “time-out” as needed. Time-outs are not just for young children or professional sports teams. If things start to become too heated, it’s important for people to be able to take a time-out. Time-outs give people the opportunity and the space to calm down and compose themselves, making it possible to continue.
  • Take responsibility for feeling the way you do, rather than blaming the other person. No one can make you feel a specific way. Use “I” statements — as in, “I feel...” Be clear and specific about what the other person did that contributed to your reaction. Rather than saying, “You make me so mad,” focus on the other person’s actual behaviors.
  • Drop your assumptions. Just because you have been living or working together for a period of time doesn’t mean you know what the other person is feeling or thinking. People grow and change. What you want, need, or expect from each other changes and may need to be renegotiated from time to time.

Ultimately, you cannot control how the other person(s) will react to your efforts to engage them in challenging but necessary conversations. However, by being well prepared and following these guidelines, you can improve the skillfulness of your participation and maximize the chances that the conversation will serve its intended purpose.

Copyright 2017 Dan Mager, MSW

Author of Some Assembly Required: A Balanced Approach to Recovery from Addiction and Chronic Pain and Discover Recovery: A Comprehensive Addiction Recovery Workbook (available April, 2017).

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