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How To Have Difficult Conversations

By Marigona Binakaj | - September 18, 2025

Avoiding difficult conversations often leads to more harm than good. Conflict aversion is part of the fabric of most people’s DNA. A substantial amount of literature exists providing tips on how to manage difficult conversations. This article distills these tips into a concise plan of action to help enter difficult conversations, and exit successfully.

Step 1: Prepare

It is essential to prepare yourself prior to heading into a difficult conversation. Timing and location are critical. Never enter a difficult conversation in the heat of the moment. The place and time of the conversation must be carefully thought out. Both you and the other person(s) need to set the scene for a successful meeting. Start with finding a calm place that is private. If you are concerned that the meeting may turn hostile, then plan to meet in a public place like at a coffee shop or food court. Once the place and time have been established, begin visualizing the meeting. Plan on doing twice the amount of listening than talking. Plan to mirror what the other person is saying so that they know they are being heard. How do you want to be seen or heard? Be very aware of your body language and facial expressions. Prepare the points that you want to make and then practice them. You can even video yourself to see what you look and sound like. The more you are prepared, the higher the likelihood is that the conversion will be constructive.

Step 2: Eliminate Assumptions

Eliminating pre-conceived assumptions or negative feelings of your partner will help alleviate feelings of distress. Consider entering the discussion with a blank slate and remove the relationship from the equation. Holding precarious feelings about your partner will work against you as you try to maintain control of yourself. The better control you have over yourself, the better able you will be to deliver your message. No matter how well the conversation begins, you will have to remain in charge of yourself, focus on your intentions, your purpose and your emotional energy.

Step 3: Be Self-Aware

It is necessary to look inward and try to recognize any personal trigger points that may result in outbursts. This requires you to be cognizant of your tone and calm demeanor. Emotions can lead to unwarranted reactions which may open the door to retaliation and further conflict. Also, consider how the other person reacts during the conversation. Consider allowing your partner to process their emotions. If she begins to seem agitated or stressed, then give her time and space to relax and collect her thoughts.

Step 4: Be Curious

Successful conversations come about when the parties have a genuine desire to understand one another. It helps to assume that your conversation partner has an abundance of information that you have yet to uncover. Trying to ascertain his interests, in addition to his desires, will prove to be helpful. Inquiring about your partner’s underlying interest will uncover solutions and it may be reciprocated.

Step 5: Acknowledge Feelings

Remember that acknowledgment does not mean agreement. Acknowledgment is a means to display that you have heard and understood a point. People may be more willing to compromise when they feel heard and understood.

Step 6: Advocacy

When your partner has finished making her points, ask if there is anything else that she wishes to say. If you have listened attentively and acknowledged her words, you now have the floor and can make your points. Recall what you practiced. Be succinct and clear. Do not overstate or understate. Use polite language. Propose solutions to the problems. Invite alternative solutions.

Step 7: Problem-Solving

Demonstrate a willingness to reach solutions together. Look for common ground and determine what is mutually acceptable. Park the more challenging or controversial subjects until later. Try to resolve any short-term and easy issues first. As for the more difficult topics, consider turning the conversation to discussing a method to resolve them such as counselling, parenting coordination or mediation.

Step 8: Be Mindful

Successful outcomes to difficult conversations typically depend on your emotional state. To optimize your participation in a difficult conversation, it is necessary to ground yourself through mindfulness and introspection. Choose to be calm and self-aware. Inward calmness will translate into positive body language which will hopefully be mirrored by your partner.

The reason why difficult conversations occur is because you are invested in the relationship and are worried about what may occur during and after the meeting. The conversation would not be difficult if you didn’t care about the relationship. Given that you do care, you want to have the conversation, even though it will be challenging. That is why it helps to follow these tips on planning them, mindfully participating in them and making these difficult conversations rewarding.

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Editorial note: This article was first published on LinkedIn in January 2023 and is republished here on the Benmor Family Law Group Blog for reference.

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