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Mastering Difficult Conversations

Mastering Difficult Conversations
Communication Skills Conversations
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Author Photo Hend Saleh
Last Update: 12/10/2026
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At the time of writing this article, I was in a Zoom meeting, talking to a screen full of black boxes, trying to hear voices coming from the void.

Author
Author Photo Hend Saleh
Last Update: 12/10/2026
clock icon 10 Minutes Communication Skills
clock icon Save article

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Note: This article is based on the blog of Adar Cohen, who tells us how to have difficult conversations.

All the other callers are members of the Executive Board, and they are in turmoil about the strategic direction they will take for their company. Many of them were no longer on good terms, and employees and stakeholders were not spared the drama that was taking place as well. At best, these calls are tense, but more often than not, they are like a grinding war. My camera is the only thing working, and I watch myself on it, trying to sound optimistic.

I've been a mediator and helped people have difficult conversations for over 20 years—in conflict zones, in living rooms, with corporate leaders, and even with people in my community. If you've avoided or put off a difficult conversation, you're not alone. We all avoid conflicts, whether at home or at work, insofar as we contribute to their outbreak in the first place.

Conflict is not inherently bad. It provides us with information on how to work with others more effectively, improve our relationships, and grow as individuals.

However, conflict is not inherently bad. It provides us with information on how to work with others more effectively, improve our relationships, and grow as individuals. It is far worse to try to avoid it. This is because you end up creating a new conflict, which ends up being more insidious and costly than the original problem.

When we help people in difficult conversations, we always aim for one of three outcomes: a solution, a plan, or a mutual understanding. The solution is considered a big deal, and it can be considered a great victory or a comprehensive decision that is expected to bear the pressures of all unknown future challenges, and this can be achieved with the presence of a mediator. But it remains a rather big ambition. We all tend to hope for a dramatic and lasting solution, but that often leads to new problems.

Creating a plan is more realistic. It is like a map that leads to finding a solution. The plan leaves open the conditions that determine the decision, but it secures a way forward and realigns the relationship with new boundaries, revised standards, and shared expectations for how to handle the more difficult parts.

But the most realistic outcome, especially in the beginning, is to focus on reaching an understanding. Understanding is a new awareness of what the other person has experienced in the conflict. It is a mutual appreciation of each other's needs, fears, and hopes. Understanding is possible, provides great comfort, and can lay the foundation for a plan, solution, and new relationship.

In my work as a mediator, I have learned that successful conversations almost always involve what I call a “core statement.” When two parties listen long and hard to each other and make an effort to listen with curiosity and empathy even when they strongly disagree on opinions, someone eventually reaches a “gem” that is not priceless. This "gem" usually takes the form of a short, powerful statement, like these two I heard recently:

  • "We've continued to struggle partly because neither of us is willing to give up on this friendship, which is great."
  • "Even when we don't get along sometimes, I never doubt your good intentions. I know you only want the best for us."

It happens almost every time, for out of the rubble of blame and anger, someone picks up a beacon and holds it high, and then I seize the opportunity and hold up the "gem" for all parties to see. That lights the way toward a new conversation centered around compromise, solutions, and good intentions.

We don't actually resolve other people's differences; we create the conditions in which people feel heard and valued.

This guide is intended to help you do just that without an intermediary, and intermediaries can be helpful in difficult times. But we don't actually resolve other people's differences; we create the conditions in which people feel heard and valued, and this increases the quality of their communication and problem solving.

When you're having a difficult conversation, you don't really need a mediator; It needs the conditions that we are good at creating and taking advantage of.

If you do not feel safe or your situation involves illegal activity or any kind of abuse, then this guide is not for you, in which case you should seek help from a professional immediately.

There are also some situations that don't require more conversation. Some relationships or difficulties are best left in the past. You should trust your instincts about whether a conversation is the right move for you, but if you think talking can be helpful, it can be. This guide gets you started.

Tense virtual board meeting representing workplace conflict

Perhaps you feel misunderstood or unappreciated at work, or perhaps you are stuck in a repetitive pattern that causes you pain and drives you away from the people you love. If you feel hurt or angry at the thought of a difficult conversation you need to have, there is a good possibility that this relationship is significant to you. Whether it's a relationship within your family, at work, or in your community, it's becoming difficult because you care deeply, or it could be that your future is somehow intertwined with the person you need to talk to.

If you feel that the situation can improve if someone genuinely listens to what you have to say, there is hope, and if you feel willing to make an effort to truly listen to someone in return, there is more than hope.

Effective steps to follow for a difficult conversation

Remember, your goal here is not to find a quick fix or plan on the spot. It must be tempting, but it is unrealistic and may backfire. Your goal is to reach mutual understanding. So what should you do?

1. Get ready for the conversation

The first step is a thought experiment: think of the person you want to talk to and allow yourself to imagine that you have just had the best possible conversation with them, and they have listened to you completely and dealt with you to your satisfaction. If the apology is right for you, imagine that you have received an excellent apology.

It is a difficult thought experiment. But you will feel comfort and gratitude for the person you had a disagreement with.

Person preparing mentally before a difficult conversation

2. Search for the “gem”

What will you tell them at that moment? Remember in this exercise that you heard the other party well, and you received an apology from him, and it went well, so what would you say to the other party if all of this happened? What lies behind this conflict? And what is the right direction when negative emotions do not drain you?

Write the first substantial statement you come up with. You can write other statements as well, but usually your first statement is the one with the real meaning. Your statement should be a true expression of how you feel, but it should also have an important meaning and a positive effect on the other person.

For example, two other substantial statements I've heard recently are: "I can tell you that you care deeply about achieving our team's goals, and I respect you very much." You can tell that this phrase carries a "gem" when you're so inclined to see through a complaint.

3. Ask yourself if you are ready

Are you willing to make a statement to them? We hold back from being generous and kind when we feel that the other party does not deserve it, and furthermore, making such statements can put us in a more vulnerable position.

If that's the case, it may be worth thinking about it another way, and uttering your statement may temporarily push you out of your comfort zone. However, the benefits that will return to you will be permanent and profound.

At this point, you should share this guide with the other person. Even if you don't follow these steps to the letter or strike up a conversation right away, it can be helpful to simply read the guide and think about it. If you do get into a conversation, having this guide in advance means they will go through the same process and reveal their permit to you, which is likely to ease your vulnerability and discomfort.

4. Call a friend

Tell a friend who is not involved in the conversation what you are going to do. The point is not that you both agree to formulate a substantial statement or even get their advice. Instead, say the four sentences below to your friend:

  • The biggest emotion I feel for the person I need to have a difficult conversation with is...
  • The biggest emotion I expect a person to feel towards me is...
  • The essential statement I would make to them is…
  • My hope from this conversation is…

The fourth sentence—defining your hope from this conversation—is an important part of your planning. Remember that the best initial outcome is a new and shared understanding rather than a comprehensive solution or detailed plan. The new understanding can comfort you and allow you to make room to move forward without expecting a miracle that resolves all tensions and conflicts in a relationship.

Chatting with your friend can relieve some of the pre-conversational tension; you'll likely get some support and sympathy from them, and you may discover a revision or adjustment you'd like to make to your substantial Statement.

5. Start the conversation

This can be done in person (if you feel comfortable), over the phone, or via video call. For many, this is the hardest part, but it will be over before you even know it.

Make your statement, immediately followed by: “I say this because I think if we both really tried, we could work this out.” It will be a little weird, but do it anyway.

Time and time again, the people I mediated with would describe feeling like they had a phobia in the moment, but it turned out to be a huge relief.

Two people having a calm face-to-face difficult conversation

Once you both have your say, ask your counterpart four questions:

  • What do you feel now?
  • We're both here because we think we can work it out; what's still a roadblock for you?
  • What can I do to help you?
  • Is there anything else you want to say to me?
Read also: How to Turn an Awkward Conversation Into an Easy Chat?

6. Listen and speak

Listening to someone you are in conflict with or avoiding conflict with is annoying, frustrating, and painful. When it gets tough, remember your purpose. Why are you having this conversation? And what hope did you draw, write, and tell your friend about? Keeping this in mind will help you keep listening.

There is no more productive and effective activity in the midst of a difficult conversation than listening.

I recently helped a group of siblings who are struggling to take care of their ailing father. They were so adept at dealing with his complicated medical problems, each so attentive to him, and all willing to take the time to care for him. But the hostility and mistrust created by decades of conflict made even the smallest form of communication and coordination impossible for them.

As they listened to each other, I saw the pain on their faces, even though they shared the same goals. They give their father the best possible care and avoid the emotional anxiety of seeing them fight, yet they can rarely bear to listen to each other at all.

During our sessions, that began to change, and they did not reach a comprehensive solution, and of course they were not familiar with each other. But they came to a powerful understanding that has the power to support and guide the way forward. They all agreed that they would keep their father out of their quarrels and that they would deal with their differences more directly. This meant that their father would suffer less and not find himself in the midst of their fraught conflicts, which is a major goal for all of them.

Active listening during a conflict resolution conversation

Moderators trust the conversation process because they have seen the powerful effect of listening over and over again. Listening—when it's difficult—puts people on the fastest track to problem solving. There is no more productive and effective activity in the midst of a difficult conversation than listening. Just as you need to be heard, you must also listen to the other person.

In fact, there may not be a viable external solution to your conflict, but just listening can greatly improve the situation. Listening fully prompts people to release their long-standing demands and grievances. In other words, there is no problem to solve if the problem goes away.

When it's time to speak up, there are some guidelines you should follow, and you may need to express frustration, pain, and anger.

Here are ways to help your conversation partner listen to you:

  • Describe your experiences and emotions rather than listing your own and the other party's mistakes. This reduces arguments that produce negative results and can unleash sympathy between the two parties.
  • Show your grievances. If there is nothing that could be on your top three list of grievances, leave the whole topic out of the conversation. Conflicting people are at their worst when it comes to their ability to listen, absorb, and respond productively to criticism. Therefore, you must use the limited scope of your partner's work efficiently.
  • Go back to the list and show it to your friend, and think carefully if there is anything you would like to share. Has anything changed since you wrote it? Was I surprised by anything? Can you point to something that happens in the conversation that gives you hope?
Read also: Mastering the Art of Ending Conversations with a Talkative Man

7. End the conversation

As the conversation draws to a close, ask each other, "What has changed for you after this conversation?" Perhaps you feel that you are being heard in a new way, that you fully understand the other person's experience, or that you don't feel the same amount of harsh feelings you did before.

Read also: How Do You End a Conversation Without Offending Anyone?

Express your gratitude towards the other person, no matter how small, and there is no need to be a compliment in every detail. What do you value in your partner, or how did it come into play in the conversation? Finally, share one commitment you'd like to make when you finish this conversation. Communicate but be realistic, and remember that the siblings have made progress without completely resolving their conflict.

Disclaimer: This article is not allowed to be copied as it is or used anywhere else under legal liability. However, paragraphs or parts of it can be used after obtaining official approval from Annajah Net administration.

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