12 Don’ts for Holding Difficult Conversations

John R. Stoker is the author of  “Overcoming Fake Talk” and the president of Dialogue WORKS, Inc.  His organization helps clients and their teams improve leadership engagement in order to achieve superior results. He is an expert in the fields of leadership, change, dialogue, critical thinking, conflict resolution, and emotional intelligence, and has worked and spoken to such companies as Cox Communications, Lockheed Martin, Honeywell, and AbbVie. Connect with him on Facebook, LinkedIn, or Twitter. 

After a recent presentation, someone approached me and asked, “I noticed that when you share your learning with us, you often give us things to do rather than telling us what not to do. Why do you do that?” I responded by stating that when someone tells you what not to do, your brain focuses on that, often leading you to do what you are told specifically not to do. For example, if you were teaching someone to ski, you would not tell them, “If you lose control, don’t look at the trees!” Making this statement would lead people to look at the trees. Rather you would say, “If you lose control, remember to look down the hill in the direction you want to go.” 

However, it is instructive to share the “don’ts” when they are followed by better options. Here is a list of 12 things to avoid when holding difficult conversations along with what to do instead. 

Don’t be vague

If no one knows what you are talking about or what they are supposed to do, then you will not achieve the results that you desire. Be specific and clear in your communication. To allay any doubt as to whether the person has understood, ask questions to assure the clarity of the person’s understanding. 

Don’t insist on talking when emotion is high

If you begin to talk about a difficult topic and negative or “hot” emotions start to emerge, it would be better to postpone the conversation until people have time to reset and calm down. Emotion tends to hijack the meaning in conversations. It becomes difficult to talk when the content of a conversation is overpowered by emotion. When emotion begins to surface, acknowledge a person’s feelings and ask questions to understand the meaning hidden behind the emotions. If possible, allow the person some time to compose themselves before continuing the conversation.

Adopting an attitude of discovery will go a long way toward increasing understanding of the current challenge.


Don’t be oblivious to your own behavior

Sometimes when talking about tough topics the other person will begin to display a number of defensive behaviors such as raising their speaking volume, talking quickly, using animated hand gestures, rolling their eyes, or using a sarcastic or cynical tone. They may also get very quiet, glare, start to frown or look upset, or respond in monosyllables. When this happens, stop and take note of your own behavior. What are you doing that may be causing a defensive reaction in the other person? People often reflect our behavior back to us. So if you notice some of these behaviors in others, check yourself, then adjust your own actions as necessary to help create a more positive tenor in the conversation. 

Don’t avoid holding people accountable

If you are holding the same conversation about a person’s behavior more than once, you are probably not holding them accountable. The reason for holding a difficult conversation is because you want something to change. If the change is not occurring, then you need to examine whether or not you are being specific about the desired changes and how you will hold that person accountable.  Setting deadlines and goals together for what will change and when will help them have a specific plan of action and allow you a defined checkpoint to then follow up. 

Don’t begin with the end in mind

Sometimes leaders approach a difficult conversation with a preconceived solution to a challenge. This is not necessarily a bad thing as long as you are open to considering the other person’s perspective and being flexible in the final outcome. Always pushing for what you want or what you think is best to the exclusion of others is a recipe for missing what is really going on and keeps you from finding a more complete understanding of the problem. Adopting an attitude of discovery will go a long way toward increasing understanding of the current challenge. 

Don’t play Mr. or Ms. Fix-it

When things go awry, sometimes leaders or managers think that they have to fix the problem or offer a solution. Look for opportunities to empower people to solve their own problems and then let them resolve them. 

Don’t be a control freak

Beginning a difficult conversation by trying to control the final outcome will most likely not create the results that you desire. A conversation that is based on the principles of dialogue demands that there be a mutual sharing of ideas and understanding. Then what is learned during the exchange can be applied to create a mutually agreeable outcome. Don’t be afraid to begin a conversation and to follow the flow of the conversation to its logical end, allowing the other person time and space to contribute.    

Don’t begin a sentence with “you” 

Starting a sentence with the word “you” can be equated with blame or accusation. Temper the use of the word “you” by using an “I” statement instead. Notice the difference: “You don’t know what you are doing,” versus, “I wondered if you know what you are doing.” Using “I” statements can have an immediate softening effect when speaking to others about potentially difficult topics. 

Don’t start a difficult conversation with your opinion or judgment

Many people tend to make this mistake when giving feedback. For example, if you said to someone, “Your presentation this afternoon was not good; you looked really unprepared,” you are leading with an opinion or judgement of the individual. This approach encourages a dialogue, rather than a possibly emotionally-charged response.

Don’t use sarcasm when speaking to others

Monitoring your tone of voice is critical in holding successful difficult conversations. Your tone is the emotional energy that you have about a topic and can make or break a conversation. The words you use in a conversation may be respectful, but your tone of voice will have a stronger impact on the outcome than your words. Being able to recognize and monitor your tone of voice will have a great positive impact on the effectiveness of your conversations. 

Don’t use “we” when you mean “you” 

We call this the use of the royal “we.” I had a boss who always used to use “we” when he was referring to me. Such as, “We really need to get that report done today.”  “We need to get that guy on the phone.” Every time he said “we,” I found myself thinking, “What, do you have a mouse in your pocket?” His use of “we” was his attempt to soften his directives, but he really did mean me and me alone. Call it like it is, and don’t patronize or demean the other person. 

Don’t assume anything

Just because you are in charge doesn’t mean that you know everything. There are other perspectives that need to be explored and understood, particularly when it comes to addressing challenges that others may have. Taking the time to ask questions and carefully listen will not only help you broaden your perspective, but also help you to create a solution that will get to the heart of the situation at hand. 

Difficult conversations are usually painful because we don’t know how to hold them, so we avoid them or we bungle any attempt to have them. Taking the time to avoid the “don’ts” listed above by choosing positive alternatives will help you be more effective in talking about what matters most and generate positive results.    

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