Most people don’t avoid difficult conversations because they don’t know what to say. They avoid them because they’re afraid of how the other person will react or worried that they themselves will escalate the conversation, and so the issue festers until it’s harder to raise, not easier. In our coaching work across BC workplaces, the single most common thing we hear is: “I knew I needed to say something months ago.”
The good news is that handling these conversations well is a skill, not a personality trait. Here’s how to prepare for a difficult conversation, and how to keep it on track when emotions rise.
Why difficult conversations go sideways
A difficult conversation usually fails for one of three reasons: it’s avoided until resentment has built up; it’s sprung on the other person with no warning or safety; or it’s delivered as a verdict rather than opened as a conversation. In each case, how you deliver the message matters as much as what you say.
Before the conversation: prepare
- Get clear on your goal. What outcome are you actually after — to be right, to vent, or to change something going forward? Aim for the last one.
- Separate the facts from your story. Write down what objectively happened, and separately, the interpretation you’ve added. People will dispute your story; they can rarely dispute the facts.
- Plan an opening that lowers defences. A short, honest, non-blaming opener (“I’d like to talk about how the project handoff went. I think we see it differently and I want to understand your view”) sets a collaborative tone.
- Determine the assumptions you’ve made. It is important to consider where your brain fills in the blanks. Once you consider where you may have made up the other person’s words, intentions, or actions, you can now prepare questions to help you gain clarity on what actually was said or done and what the intention was.
- Choose the time and place. Private, unhurried, and not at a moment of peak stress for either of you.
- Consider how you will keep your cool. This is where three key self-regulation skills will come in handy. Managing your body movement will help you regulate your heart rate, blood pressure, and body temperature. Hold yourself the way you would if you were cool, calm, and collected. This includes a relaxed jaw, shoulders down, and good posture. When you notice a change in your body movement, such as your knee starts bopping up and down, you begin shifting from side to side, or a muscle begins twitching in your face, calm your body movement and return to your usual manner of holding your body. Next, consider listening on purpose. When we listen to other people on purpose, it stops our own negative internal story. The brain can listen or it can judge. When you choose to listen, you drop judging and, along with it, regulate your heart rate, blood pressure, and body temperature. It is also important, of course, to use the voice inside your head as your guide through a difficult conversation. Train your brain over the course of two weeks to repeat helpful statements to you. The brain is a patterning organ; what it hears the most of, it will repeat. That means if for two weeks you repeat positive statements to yourself, your brain will allow you to access these messages in difficult conversations. The reason for two weeks is that is how long it takes DNA to shake in a cell and form a wire and connect to other brain cells. Phrases you can tell yourself include: This will pass. All moments pass, the good, the bad, the ugly. How do I want to be when this is over? What are they trying to tell me? Just catch it and give it back to them. I got this.
During the conversation: stay in it
- Use a step-by-step process. Start by sharing your positive intention for engaging in the conversation. Then name what it is you wish to discuss/negotiate/sort out. Share your needs moving forward and gather the needs of the other party. Summarize and turn to outcomes/actions/next steps.
- Lead with curiosity, not conclusions. Ask, prove you heard what they said, and then consider a response. Key listening (proving) skills include agreeing where you can, sharing what the person said that makes sense to you, reframing what the person said to what actually matters to them moving forward, or simply paraphrasing back what you heard.
- Attend to your own internal signals. When you feel your heart rate climb or your jaw tighten, that’s the moment to slow down, not speed up. Remember to manage your body movement, listen on purpose, and trust your trained self-talk.
- Name the dynamic, not the person. “We seem to be talking past each other” beats “You’re not listening.”
- It’s fine to pause. If the conversation overheats, taking a break and returning is a strength, not a failure. In fact it is helpful to say “I am noticing I am struggling in this conversation right now and I want it to be productive. Let’s take a break and try again.”
What changes when people get this right
When a difficult conversation goes well, people settle, triangulation and gossip stop, productivity increases, and teams begin to merge together. When supervisors avoid difficult conversations, we know the team begins to step in and dish out justice. For example, a few months ago, we conducted an assessment on a large team where staff members had broken off into factions and cliques. Some staff members were focused on creating drama, while others were focused on avoiding it. Some staff members were refusing feedback and engaging in escalated behaviours, including anger, yelling, withdrawing, and watching movies on company time. The managers were aware of the issues, but, as is common, some had received no training in managing difficult conversations, and some were brand-new managers. Instead of having direct conversations to manage behaviour, the managers had created workarounds so they did not have to address the problematic employees. The problem was that the behaviour continued, and other hard-working staff members were fielding the majority of the work and getting burned out. Through the assessment, we made a number of recommendations, including coaching for managers to learn to navigate difficult conversations. Each manager engaged in five coaching sessions focused on managing escalated behaviour, setting limits, handling grievances and complaints, and saying no. With the support of their Human Resources team, the managers began addressing inappropriate conduct with greater confidence. Over time, the result was a more cohesive team that understood the expectations for workplace decorum and gained greater respect for their leadership. Alongside this, the managers understood their role in behaviour management and ensuring a psychologically safe workplace.
When to bring in support
Some conversations are too charged, too senior, or too entangled in history to navigate even when you know you have to. That’s where we come in. Conflict and communication coaching is designed to prepare you for high-stakes conversations. In a confidential, one-to-one setting, we use shadowing, real-life simulations with recorded analyses, in-the-moment feedback, and case analyses to build skills you can apply immediately. For example, recently, an organizational leader requested coaching sessions because she had found herself as the respondent in a few too many bullying and harassment complaints. The goal was to improve her reaction and listening skills in the face of escalated employee conduct. We focused on self-regulation, as well as key listening and assertion skills. Another individual was provided with coaching sessions by their employer to help them navigate client reactions as they transitioned from a female to a male with the pronouns he/him. This person was being misgendered repeatedly, finding himself getting angry constantly, and not knowing how to address not just client reactions but also the reactions of colleagues. We focused on mindset approaches, resilience, and assertion skills. A school principal chose to engage in coaching sessions to navigate what appeared to be a negative school dynamic. In this case, coaching focused on supporting the school administrator in conducting a school-wide culture assessment, identifying themes, reporting back to staff, and involving staff in determining next steps for the school. The principal needed support to hear what the staff needed more, less, or differently from the principal, and, with support, was able not only to digest the feedback but also to create a leadership action plan for change. Coaching is a process that allows participants to have a positive, future-focused learning experience.
Frequently asked questions
Preparation. Getting clear on your goal and separating the objective facts from your interpretation of them prevents most conversations from derailing before they start.
It is important not to take people by surprise, but rather to approach them first and ask to have a conversation about XYZ. It’s important to clearly state the topic and your positive intention for the discussion. Then, jointly set up a time and place to meet.
Defensiveness is a protective mechanism. If you can aim to help them feel heard and safe, you can get past the defensiveness. Certain skills can be great allies in difficult conversations, such as telling people they make sense, agreeing where you can, reframing what they are saying matters to them, or simply asking them to tell you what the main message is that they are conveying.
Yes. Our one-to-one coaching is confidential and practical, using simulations, feedback, and case analyses to build skills you can use right away, and it’s available virtually and in person.
Don’t wait for the conversation to get harder
If there’s a conversation you’ve been putting off, the cost of waiting almost always exceeds the discomfort of starting. We can help you prepare for it or build the skills so the next one comes more easily.
Contact Turning Point Resolutions and learn more about our coaching services.
Related reading: Workplace Mediation in Canada · Facilitating groups through conflict
About the author
Dr. Raj Dhasi is the President of Turning Point Resolutions Inc. and a faculty member at the Justice Institute of British Columbia’s Centre for Conflict Resolution. She holds a Master’s degree in Organizational Conflict Analysis and Management and a Doctorate in Social Sciences, with over 25 years of experience supporting workplaces, school systems, and communities through complex conflict. LinkedIn