6 Tips for Making Difficult Conversations Easier

The challenge in learning to hold difficult conversations begins by learning to understand yourself. You must be willing to take a look at your thinking and feelings and examine them for accuracy.

I have surveyed leaders, managers, and individuals about why they won’t speak up when they have something important to say. Years ago, when working for a company, I came out of a budget meeting where upper management told us we had to slash our budgets by half of what we projected for the next year. When I asked my manager what he thought about this edict, he replied, “That won’t help anything! They do this every year. It’s their tactic to show a profit to the shareholders.”

I asked, “Why didn’t you say something?”

He responded, “I value my life!”

No one trimmed their budgets. In seven months, the company filed for bankruptcy.

I often have reflected on this situation over the years and talked about it with others. In talking about people’s reticence to speak up when they feel it’s important, I have been surprised by the responses people often give when asked why they don’t want to say anything.

Here are the most frequently offered replies:

  • “I don’t know what to say.”
  • “I don’t want to hurt their feelings.”
  • “I don’t want to damage the relationship.”
  • “I don’t want to lose my job.”
  • “I don’t want to make matters worse.”
  • “People might not like me.”
  • “I don’t want people to think I don’t appreciate them.”
  • “If I am the only one who brings it up, they might make me do something about it.”
  • “If we ignore it, eventually it will go away.”
  • “I don’t like dealing with conflict.”
  • “People don’t want to hear the negative.”
  • “Rather than talk about it, it’s just easier to deal with it myself.”

You likely have had such thoughts when considering whether to speak up or not. However, in an attempt to increase your motivation to speak candidly when it is important, there are two dynamics of which you should be aware.

First, for each of these statements, there is an underlying assumption that may or may not be accurate. For example, in the first response, “I don’t know what to say,” is the assumption that there is a “right” way and a “wrong” way to say something. Perhaps this is true, and perhaps it is only the limited perspective of that individual. Behind the second response, “I don’t want to hurt their feelings,” we find the assumption that when we speak up, we will hurt someone’s feelings. Such an assumption is incomplete or inaccurate, depending on the person and the situation. Because our thinking and the assumptions we make drive our behavior, such statements predict our unwillingness to speak up in certain situations.

Second, if you examine each of the previous statements, you will recognize they are projections of what may happen in the future. Ironically, with each statement there is usually no evidence in the present that what the individual is thinking will ever occur except that they thought it might. When I have pressed individuals for evidence to justify their thinking and the accuracy of their projections, it is rare for them to be able to offer any supporting data.

To make matters worse, such negative thinking usually gives rise to negative emotions that provide us the justification for inaction. It isn’t uncommon for us to hear ourselves say, “Yikes! Even thinking about saying something makes me feel extremely uncomfortable!” Obviously, if we don’t feel right or comfortable about speaking up, then we usually don’t.

Why Does This Matter?

Part of being willing to change or improve anything is to be able to talk about what is not working. Our unwillingness to speak up is a cheap trick our brains play on us all too often when deliberating whether or not we should throw our two cents into the pot.

As the author of “Overcoming Fake Talk,” I would suggest that there is all kinds of talk going on in our lives that is intentionally or unintentionally vague, ambiguous, unclear, or unspoken that contributes to our lack of results. There are also those conversations that are so filled with emotion, aggression, abuse, or disrespect that the listening party becomes hijacked to the point that they lack the rationality to process the message or even to engage. When we don’t get the results we want, that’s when we learn our conversation may have gone awry.

If we want to achieve the results we desire, then we need to learn to hold REAL conversations. Here are some tips for improving the quality of the conversation and the quality of your results:

1. Identify your stories. The stories we tell ourselves are full of assumptions and projections we make that we use to explain how things are and what will occur in the future. If you can start to listen to yourself and hear the stories you tell, you will put yourself in a position to make a more conscious decision about whether you should speak up. If you decide your story is inaccurate, then perhaps you might venture to share something others need to hear.

2. Look for evidence. As you start to surface your thinking, ask yourself what experience or evidence exists that would support the assumptions you are making. Remember that your brain is trying to protect you from what it may perceive as impending danger. This is usually a good thing. However, you may wait to make a conscious choice about what course to take. You might ask yourself this question, “Would speaking up improve the current situation when weighed again the benefits of remaining silent?” It is also worth remembering not to believe everything you think in the absence of supporting data. If you are thinking negatively, then you most likely will decide not to speak up. However, if you firmly believe there will be negative consequences for speaking up, then perhaps keeping your thoughts to yourself is duly warranted. Being conscious about such a choice is what is most important.

3. Check your feelings. When we begin to feel uneasy, that is a sign that our brain is feeling uncomfortable. That is because we are starting to think some things that it doesn’t agree with. This is a good thing because it signals we might learn something that will help us to improve. Check your feelings and don’t believe everything you feel. Accurately assess what you know outside what you feel in the moment. Then make the decision to share based on some degree of rationality. Negative emotion signals that something is going on in our heads; use the emotion to check out your thinking.

4. Use REAL skills. These skills are:

Recognize and suspend your judgments.

Express your thoughts, ideas, experiences, and feelings in ways that invite others to express theirs.

Ask questions to understand and clarify.

Listen and attend to all the verbal and nonverbal messages that are being sent.

These are the skills or behaviors that are present in all effective communication. Learning how to use them will greatly increase the likelihood of conversational success.

5. Prepare the context. Preparation ensures that you will be able to manage the conversation effectively. Here are some questions you will want to answer before holding the conversation:

  • 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 of these questions will help you to know what you want to talk about, anticipate the other’s reactions, and to remain in control throughout the interaction. Preparing also will lessen any fears you may have about just “winging” it.

6. Go with the flow. Realize that a conversation is not something you can control. There is a current in a conversation. You have to be willing to jump in and go where the conversation will take you. You can prepare ahead of time and learn to manage the dynamic or flow of the conversation, but you have to be willing to jump in and learn as you go. Noticing where the conversation is going, asking questions to gain understanding, and knowing where you want to go will greatly help you to achieve the desired objective.

The challenge in learning to hold difficult conversations begins by learning to understand yourself. You must be willing to take a look at your thinking and feelings and examine them for accuracy. Learning to use the REAL skills for any conversation and doing a bit of preparation will go a long way in helping you to hold a conversation about what matters most.

John Stoker is the author of “Overcoming Fake Talk” and the president of DialogueWORKS, Inc. He has been in organizational development work for more than 20 years, helping leaders and individual contributors learn the skills to assist them in achieving superior results. He has experience in the fields of leadership, change management, dialogue, critical thinking, conflict resolution, and emotional intelligence, and has worked with such companies as Cox Communications, Lockheed Martin, Honeywell, and AbbVie.

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