The Secret to Having a Good but Difficult Conversation

How to successfully engage someone when the conversation is uncomfortable.

Many of the people I coach tell me, “If the conversation is difficult, people don’t open up to me.” I then ask, “How are you listening?”

Time is NOT the greatest gift you can give someone. The gift is what you do with the time you are together.

Do you fully receive what the person says and expresses with respect and care? When you accept and honor people for who they are and what they are experiencing, they are more likely to open up and explore with you.

Receiving the person fully, not just listening to them, is the secret to a having a successful difficult conversation.

Here are some guidelines to help you prepare, enter, and engage someone to increase your odds of having a good outcome:


1. Consider why the person would want to make a change. When people feel you only want to talk to them to fulfill your needs and goals, they won’t engage with you. They have to feel that the change you want them to make or the point of view you want them to perceive is tied to something they value, too.  What’s in it for them to have this conversation with you — to have a good relationship in the future, to be better respected by friends and colleagues, to have others see them as a great leader, to reach specific goals at home or work, or to have more peace of mind?

What have they expressed to you in the past that is important to them? Sincerely tie what you want to what they want to ensure a good outcome.

2. Check your feelings. If you enter the conversations feeling angry or disappointed, the person will shut down or react defensively. You need to feel respect and hope.

Respect doesn’t require admiration. Can you appreciate and acknowledge the innate worth of the individual? Remind yourself that the person is an intelligent being doing his best with what he knows right now. Visualize how you will stay respectful in your tone and hopeful that you can work this out together.

3. Let go of knowing. Instead of thinking you know how the person will react, try believing anything can happen. You might be surprised. Be curious about what the person thinks and what solutions might emerge.


Start the conversation by sharing what you want for the person that you hope they want too. Then share what occurred that you think could hinder this goal. Remember to:

1. Release the need to be right. Be curious and ask questions to understand their perspective and how they see themselves achieving their goal in the future.

2. Be sincere. Don’t just show care and respect; feel it.

3. Listen to their explanations. Not only do they need to feel heard before they will explore with you, you need to hear their views to know what to say next. Appreciate their perspective before you ask if they would be willing to look at other ways to achieve the goal.


1. Once you open the conversation, acknowledge both their words and feelings.For example, say, “You seem very upset that your efforts were ignored. Is that right?” Many people walk through life believing no one cares or understands them. Demonstrating that you hear and understand their feelings may be all they need before you can ask what they need to do next.

2. Don’t rehearse what you are going to say while they are talking. Don’t get distracted by your thoughts. Remember, you can’t connect with others if you don’t stay present to what they are saying.

3. Resist reacting to defensive or rude behavior. Stay calm and model the behavior you want from them. Notice when your stomach, chest, shoulders, or jaw tighten up. Breathe, relax your muscles, and choose to feel compassionate, curious, patient, or hopeful instead.

4. If you can’t get over feeling angry or disappointed with their reaction, tell the person why you are feeling that way. Then follow up with hope for the future should they choose to work toward achieving the goal.

5. Help them think for themselves. Summarize what they say and ask questions that might help them question their own logic and decisions. Based on what they tell you, say, “So you believe that… “  or “You think other people believe…” Then ask if another reality is possible.

6. Listen for the unmet expectation. What did the person not get or afraid they won’t get, such as recognition, acceptance, or inclusion? Many people cover their fears and disappointments by complaining, blaming, and criticizing others. Try to understand what the person really wants. Feeling understood can diffuse negative feelings. Then you can help the person determine how to get the need met.

7. Recognize unwillingness. If the conversation is going nowhere, call it out. For example, say, “You don’t seem willing to look for a solution. Is that true?” If they agree, then you need to determine what action you need to take next based on their expressed unwillingness to move forward.

Difficult conversations can be the most meaningful times you spend with others. Instead of trying to fix people, help them feel seen, valued, and understood. Then maybe together, you can find a way forward.


Originally published at Psychology Today