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Conversational Intelligence

Dreading an Upcoming 'Difficult' Conversation? Here Are 10 Tips That Can Help.

Asking questions up-front and then really listening to the answers can prevent a whole lot of grief later.
Dreading an Upcoming 'Difficult' Conversation? Here Are 10 Tips That Can Help.
Image credit: Klaus Vedfelt | Getty Images
Guest Writer
Author, President of DialogueWORKS, Inc.
7 min read

When I conducted research for my book, Overcoming Fake Talk, I was interested to discover why so many people were afraid to talk about certain topics -- what I call undiscussables. Undiscussables include anything that we think and feel but choose not to share. In short, undiscussables are something we keep to ourselves. 

Related: Straight Talk: How To Have Good Difficult Conversations

What my research uncovered was that people I observed were often afraid to talk about what matters to them most.

Some were afraid there would be negative consequences resulting from speaking their minds. Others were afraid of how people might react and the conflict that might result. Still others would argue that they didn’t know how to hold a difficult conversation. They just didn’t know how to do it “right.” Others feared that their listeners might not like them if they shared their concerns.

Whether there were grounds for any of these reasons or not was irrelevant. Because, when something is real to us, we end up believing those thoughts, even if they aren’t based in facts. If we try to hold a tough conversation, and it doesn’t go well, we use that negative experience to support our initial belief that discussing that topic was futile in the first place.

Or, worse, we never even make the attempt to talk about a tough topic. The result? Everything stays the same or may actually get worse.

Here are 10 tips to help you overcome your fears and successfully navigate a difficult conversation:

1. Prepare yourself. Identify how you feel and what you are thinking about the current situation or person involved. Once you surface your thinking, ask yourself, “Is my thinking absolutely true?  What facts or data support my perception?” If you can find evidence that challenges your thinking, then it’s time to reevaluate your position.

Related: 7 Ways to Have a Difficult Conversation Without Losing Your Client

This reassessment should take the edge off of your feelings or your negative judgments about the situation. It should also help you adopt a spirit of discovery going into the conversation that will help you be more attentive to learning what you may not know or understand.

2. Identify your purpose. Identify what it is that you would like to achieve by holding the conversation. Be as specific as you can. Remember that if you don’t know what you want, then you cannot achieve what you have not clearly delineated as your ultimate goal.  

3. Think through the context. Here are some questions that should help you prepare for a difficult conversation by understanding the context:

  • Topic -- What is the topic of this conversation?
  • Person -- How might this person respond to the topic?
  • Purpose -- What do I want to see as an outcome of this conversation?
  • Past -- What do I know about the situation? What are the facts?
  • Plan -- What is the plan for achieving the desired objective of this conversation?
  • Assumptions -- What assumptions am I making about this person in this situation?

Taking a minute to answer each question will help you anticipate the other person’s reactions and remain in control throughout the conversation. Reviewing the context will also lessen any fears you may have about just “winging it.”

4. Gain your listener’s attention. To do this, you will want to use an Attention Check. An attention check entails simply saying, “I would like to talk about ... Can we do that?” Make this initial statement in a calm, non-judgmental way so as to gain the interest of your listener.   

5. Share facts first. Begin by sharing the facts using an “I-statement” such as, “I noticed that you haven’t given me the report that you said you would give me first thing this morning.” In this way, you can distinguish between what is fact and what is interpretation or opinion.

6. Share thinking second. Follow your fact “I-statement” with an “I-statement” that includes your thinking, such as, “I am wondering if something came up that kept you from delivering the report on time.” Always give the person the benefit of the doubt when sharing your thoughts. For example, it would do no good to say something like, “I think that you are lazy and instinctively poor as a planner.” Say that, and the conversation is over. Your listener’s brain will move to self-protective mode and the conversation will degrade into a defensive battle for supremacy where both parties lose.

7. Ask questions to gain understanding. After using an Attention Check and sharing facts and thinking, you are ready to engage in discovery. The purpose of this step in the conversation is to learn what you know or don’t know. For example, in the previous scenario, you might ask, “What happened?” or, “What kept you from being able to meet the deadline?” Try to ask as many questions as you can to completely understand the other person and his or her point of view.

8. Clarify your understanding. In order to clarify, simply summarize the other person’s point of view first and then your own. After summarizing, end in a question by asking the person if you have understood correctly. For example, “You were unable to get the report to me this morning because another manager asked you for the budget. You initially felt that you could complete both requests, so you didn’t ask for an extension. Is that correct?”

The reason to summarize the other person's perspective is, first, to gain his or her attention; then, the person will listen to you talk about your perspective. By ending in a question, you'll be asking the person to confirm or disconfirm what you have understood. This creates respect and signals that your understanding of the other person is important to you.  

9. Build a plan. The whole reason for talking about a tough topic is that you want something to change. It is helpful if you have a plan in mind before holding the conversation. This will reduce any anxiety you may experience due to a lack of preparation. However, don’t be surprised if you find your original plan won’t work due to what you've learned by asking questions. Apply your learning and adjust your plan as needed to benefit both parties going forward. 

10. Gain commitment to the plan. Discuss your plan; then ask your listener if he or she is committed to the course of action you have created together. And watch for a reaction. If the person hesitates, takes a long pause or offers an eye-rolling statement about personal commitment, something is amiss.

Go back to asking questions to understand the response you just saw. Make sure that both of you are dedicated to your plan of action so you aren’t talking about the same topic again weeks later. Also, don’t hesitate to follow up to see if the plan you've agreed on is working or needs to be further adjusted.  

Related: Difficult Conversations: What Not to Say

Overcoming your fear of difficult conversations can be alleviated by taking a few moments to think through and prepare for the conversation beforehand. Doing so will reduce any stress you feel and help you develop a plan to help you and your listener carve out a mutually successful outcome. Taking the time to follow these steps is well worth the effort and will almost surely yield better results.  
Opinions expressed by Entrepreneur contributors are their own.

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