10 Ways to Handle Difficult Conversations

Posted by Todd Smith

Delivering unpleasant news, correcting misunderstandings, confronting a friend or family member, and dealing with hard-to-talk-about issues are the kinds of conversations most of us dread. They’re a part of life, however, and you can’t avoid them. Although you may never be 100 percent comfortable in these situations, there are a number of things you can do to make these necessary talks as productive and painless as possible.

When handled calmly and with respect for the other person, even the most challenging conversations can lead to an improved state of affairs for all involved. When you practice the art of handling difficult conversations, you learn valuable lessons about interpersonal communication that can be applied in many different circumstances. In addition, your ability to influence others grows and so does their respect for you.

Below are ten guidelines to help you confront challenging situations. If you are intentional about implementing them, your results will improve and you will be more likely to reach your desired outcome.

1. Choose the right time and place. If you are initiating the conversation, take the “emotional climate” into account. Don’t hold the conversation when the other party is upset or angry. Respect the other person’s privacy by minimizing the chance that you may be overheard. Whenever possible, have these conversations face-to-face.

2. Anticipate that you may not be on the same page. Different perceptions of intent, interpretations of the facts, and judgments about what is right or best are usually at the root of all sensitive conversations. When you begin with this in mind, you will not be surprised when these root issues arise. Remember, what may be logical to you may not be logical to others.

3. Use a respectful tone. The tone in which you communicate is as important as what you say. Speak calmly with kindness and respect. Your tone should reflect your willingness for a good outcome which increases the likelihood that your message will be received in the manner in which you intend.

4. Genuinely desire a win-win outcome.  If you begin the conversation with the intent to win the other party to your point of view, you’ll often be disappointed. Instead, aim for a compromise or resolution that satisfies your goal and the needs of the other person.

5. Be empathetic. Try to understand the point of view as well the emotional state of the other person. Ask questions to learn their perspective.  Understanding the other party’s position helps you make better decisions on how to address the situation. I have found that, in most cases, the other person is aware of what happened and usually accepts responsibility to correct the situation. When you show genuine interest in understanding the other person’s side of the story, you are more effective in resolving the matter.

6. Maintain eye contact.  As in any constructive face-to-face communication, maintaining eye contact helps you gauge the receptivity of the other person throughout the conversation and demonstrates your honesty and desire to listen to the other person.

7. Stay in control. If you express anger, it is natural for the other person to respond accordingly to match your emotional state. Do whatever it takes to remain calm.

8. Write it out. If time permits, it is helpful to put the details of the situation in writing. Include what you wish both parties to achieve. Doing so gives you an opportunity to consider all views and nuances of the situation. Taking the time to properly prepare for any important conversation yields better results.

9. Don’t interrupt. When the other person is speaking, never interrupt. Show the other person the respect you want to be shown when you are talking. In addition, don’t appear like you are anxious to respond. People who can’t wait to speak generally aren’t listening because they are so focused on what they want to say.

10. Don’t team up. Avoid saying things like “Everyone in the department feels the same way,” or “I have heard about this from countless people.”  When I hear these kinds of statements, I immediately discount what is being said because in most cases they are exaggerations. If there is an issue that needs to be addressed, resist the temptation to strengthen your position by including others. If the issue is so serious that you need to bring others into the discussion, make sure they are present.

If you are a person who dislikes confrontation, difficult conversations of any nature can be stressful. You can, however, be proactive in reducing this stress when you accept that such conversations are inevitable from time to time and that you can improve your skills in dealing with them by putting some of the above recommendations into practice.

Let me also encourage you to never try to resolve a conflict through email. Demonstrate your desire to address the situation properly by picking up the phone and calling the other party.

This lesson is intended for the type of issues that most of us have to face from time to time.  If you are dealing with a serious situation, seek help from a trained professional.

How are you at handling difficult conversations? Please share your tips and insights in the comments section below this post.

To be a competent communicator, you must strive for excellence to master the little things that go into effective communication.

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About the Author:

Todd Smith is a successful entrepreneur of 43 years and founder of Little Things Matter. This blog contains over 200 of his timeless life lessons.


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