Strategies for Difficult Conversations

By Maureen Kanwischer

Weíve all been there Ė the need to initiate a conversation with employees, your boss, your spouse or your friends about something that youíre not particularly comfortable with. And unfortunately, the usual action is no action. We put off having the conversation hoping the issue will resolve itself or simply go away. But it doesnít, and there comes a point when you know you have to suck it up and begin communicating.

A difficult conversation does not have to be a horrible experience. There are strategies that you can use to create a positive outcome and reduce the adversarial or uncomfortable feelings associated with difficult conversations. Following are a few strategies that you can use to mitigate the fear of initiating and following through on a difficult conversation.

Prepare Yourself

The first step in tackling a difficult conversation is to prepare yourself. If you go into the conversation already convinced it is going to go badly, then it probably will. Take some time to think through your motives and establish what you hope to accomplish. Try to get to the point where you can begin the conversation with a supportive and positive tone. You have more control of the situation than you think- work to maintain your supportive and positive tone in order to avoid the conversation becoming adversarial.

Initiating the Conversation

Start out by asking questions. Get the other person to share as much as possible about their point of view. Be curious, listen and let them talk until they are finished. Resist the temptation to interject your opinion about their statements. In this phase, you should be listening and learning all you can about the situation. You may be surprised to learn that your preconceived thoughts on how the other person views the subject may be different than what you expected. By allowing them to share their thoughts, you will gain a keener insight as to how to approach your points.


As you learn in any sales or negotiation training, you have to be able to understand where the other party is coming from. Donít confuse understanding their point with agreement on your behalf. You must make sure the other person knows that you heard and that you understand their position. Acknowledge what you heard from them.

Your Turn

Keeping the same tone from the Acknowledgment phase, bring up some points from your perspective. Clarify your position without minimizing theirs. Maintain control of your emotions and do not be come adversarial. One of the biggest influencers in the outcome of the conversation is how you deliver your message. If you are supportive, understanding, and centered, you will have a much better outcome. Avoid punishing, condescending or critical statements.

Problem Solving

Try to get agreement with the other person about how you got to this point. You donít have to agree, but you both have to recognize the intentions and events that got you to this point. Remind yourself of the original question: What do you hope to accomplish by holding this conversation? Bring yourself back to the original intent. At this point, both parties should be introducing options to address the situation, trying to find solutions that meet both sidesí interests. You should also lay the groundwork for ongoing steps: communication, reports, etc.

Integrating these strategies into your conversation will help drive toward a successful outcome. If the conversation becomes contentious, remember your original intent and get yourself back to a supportive stance. Begin your conversation in a friendly, inquisitive manner. Be an empathetic listener. Donít let fear of a bad episode prevent you from engaging in a critical conversation.

Difficult Conversations, by Douglas Stone, Bruce Patton, and Sheila Heen
FAQs about Conflict, by Judy Ringer. (

Copyright 2011
Feel free to publish this article to your own site as long as you give credit: Maureen Kanwischer of Momemtum Business Consulting and link to my website: Thank you.