How to Have Difficult Conversations

Author: Jordan Chong |

Blog by Recalibrate Therapeutic Services

Learning how to talk to people about difficult topics is an incredibly valuable skill, even though it can feel very uncomfortable. Throughout life, you may need to address sensitive issues such as breakups or marriage within a romantic relationship. In the workplace, difficult conversations often involve performance concerns, salary negotiations, or conflict with colleagues. There are also moments that require vulnerability, such as sharing when someone you care about has hurt your feelings or crossed your boundaries. These topics are challenging by nature because they often come with a fear of conflict or the risk of damaging a relationship, which often leads people to stay silent or avoid the issue altogether. However, difficult conversations are unavoidable in both personal and professional settings, making avoidance an ineffective long term solution. While it may feel easier in the moment, unaddressed issues tend to grow over time, leading to resentment and misunderstandings. Avoiding these discussions can also weaken your ability to be assertive and communicate your needs, leaving you to suffer in silence and miss opportunities to develop healthy communication and negotiation skills. With effective communication tools, difficult conversations can instead strengthen relationships, create honesty and mutual respect, and support emotional growth and maturity. This blog post explores the different stages of having difficult conversations and offers practical strategies for approaching each stage.

Noticing Something You Want to Talk About

Every difficult conversation begins with the realization that something is bothering you. Someone in your life may have hurt your feelings, crossed a boundary, or left you feeling confused. When this happens, it is important to consider whether the issue is worth addressing. In some cases, the situation may have been a one time occurrence, you may not interact with the person often, or you may recognize that they were having a bad day and that the behaviour was out of character. Deciding whether to speak up can be challenging, but reflecting on whether the issue is likely to repeat or whether addressing it could prevent ongoing conflict or emotional distress can be helpful. Levine et al. (2020) note that people often focus too heavily on the short term discomfort of difficult conversations while overlooking their long term consequences. They suggest that avoidance or lack of honesty can lead to unhealthy relationships or recurring uncomfortable situations. If you decide to move forward with the conversation, Prober et al. (2022) recommend several preparation strategies. These include identifying specific moments when the behavior occurred so you can provide clear examples and outlining the main points you want to discuss to ensure nothing is forgotten in the moment. It is also important to clarify your goals for the conversation, how you plan to communicate your boundaries, and what solutions you may propose.

Bringing up the Conversation

When initiating the conversation, it is important to ensure that you are in a calm and grounded mindset. Taking time to regulate your emotions beforehand can help prevent frustration or impulsive reactions from influencing the interaction and making you appear unapproachable. Let the person know that you would like to talk about something important and suggest meeting in a private setting to reduce distractions, interruptions, or the presence of others. Choosing an appropriate time is equally important, as neither of you should feel rushed, overwhelmed, or emotionally charged. At the beginning of the meeting, Prober et al. (2022) recommend sitting beside the other person rather than directly across from them, as this positioning can help create a sense of comfort and trust, making open communication easier. They also suggest addressing the topic directly but respectfully by clearly stating the purpose of the conversation and what you hope will come from it.

Having the Conversation

During a difficult conversation, several strategies can help the discussion go more smoothly. One key approach is focusing on your feelings rather than emphasizing the other person’s actions. For example, if someone made an insulting joke, you can explain that the comment made you feel hurt or upset instead of centering the discussion on the joke itself. Accusatory language often leads to defensiveness and reduces the likelihood of cooperation. When explaining the issue, be honest about your thoughts and clearly communicate what you hope will happen after the conversation before offering possible solutions. Levine et al. (2020) recommend using supportive language and viewing the conversation as an opportunity for growth rather than conflict. Framing the situation as a shared problem to work through together helps shift the dynamic away from blame and toward collaboration. After expressing your perspective, it is crucial to pause and actively listen to the other person’s thoughts and experiences. Kimball et al. (2013) emphasize that attentive listening plays a central role in understanding and decision making during difficult discussions. Whether the other person agrees or disagrees, try to consider their point of view, show empathy, and explore what outcomes they would like to see. Prober et al. (2022) add that remaining nonjudgmental while listening encourages openness and helps prevent escalation. Staying composed and listening without interrupting demonstrates respect for the other person, which would help both parties have a civilized conversation to discuss the issue.

After Speaking

As the conversation comes to a close, aim to end on a positive and respectful note. Thank the other person for being willing to listen, as these discussions can be uncomfortable for everyone involved. Summarize what was discussed to ensure mutual understanding and reduce the risk of miscommunication. Clearly state how you plan to move forward and demonstrate your commitment to the agreed upon approach. If you later notice the other person making an effort to follow through, acknowledge and appreciate their willingness to change in support of the relationship. Prober et al. (2022) emphasize the importance of self reflection after the conversation, including considering what went well and what could be improved. Although difficult conversations are challenging, they often become easier with practice and thoughtful reflection. Engaging in self care and regular self check-ins afterward is equally important. Pay attention to how you feel emotionally and respond with appropriate coping strategies to recharge your mental state. Leff et al. (2016) highlight that self care helps prevent burnout, particularly for individuals who frequently engage in emotionally demanding conversations. They recommend rest breaks, connecting with supportive people, and engaging in soothing activities such as taking walks, engaging in hobbies, or listening to music. While addressing difficult topics can feel uncomfortable, taking the initiative to do so is something to be proud of. Avoiding problems like these often allows them to grow and hurt relationships rather than protect them. It takes a lot of bravery to speak up to others, but doing so will help you become stronger, as you become more comfortable communicating your feelings and solving challenges that life throws your way.

References

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Robinson, M. E., Geller, G., Roter, D. L., Larson, S. M., Lenz, H.-J., Garcia, A. A., Braddock, C. H., Aminah Jatoi, Zúñiga, L., Montori, V. M., Koenig, B. A., & Tilburt, J. C. (2013). Listening in on difficult conversations: an observational, multi-center investigation of real-time conversations in medical oncology. BMC Cancer, 13(1). https://doi.org/10.1186/1471-2407-13-455 

Levine, E. E., Roberts, A. R., & Cohen, T. R. (2020). Difficult Conversations: navigating the  

Tension between honesty and benevolence. Current Opinion in Psychology, 31, 38-43.https://doi.org/10.1016/j.copsyc.2019.07.034

Luff, D., Martin, E. B., Mills, K., Mazzola, N. M., Bell, S. K., & Meyer, E. C. (2016). Clinicians’

strategies for managing their emotions during difficult healthcare conversations. Patient Education and Counseling, 99(9), 1461–1466. https://doi.org/10.1016/j.pec.2016.06.017 

‌Prober, C. G., Grousbeck, H. I., & Meehan, W. F. (2022). Managing Difficult Conversations: An

Essential Communication Skill for All Professionals and Leaders. Academic Medicine, Publish Ahead of Print(7). https://doi.org/10.1097/acm.0000000000004692 



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