Tips for Handling Challenging Conversations during the Holidays

Everyone is challenged at some time or another during the holiday season with spending  time with family members or friends who seemingly lack any sense of decorum or civility.  That’s why you really only see them once a year or try to avoid them whenever possible the rest of the year. There are a number of typical scenarios that may occur. In each situation there is a principle that when applied will help you to improve your ability to manage a potentially frustrating situation.

“The Competition”—When some families get together everything seems to turn into some kind of a competition. The competition unconsciously turns to who can be the loudest, who can tell the best story, or who can tell the worst story. The whole conversation dynamic seems to focus on “one-upmanship.”  Once everyone gets pulled into this dynamic, the whole conversation ends up spiraling out of control, people become disrespectful, or even downright nasty.

What You Can Do - To manage the conversation and achieve a more positive result, you must learn to recognize what is happening in the moment—become an observer. This requires you to not only participate in the content of the conversation, but also observe what is being said by whom and how the message is delivered. Once you can recognize what is happening, then you can take steps to shift out of this dynamic. You can do this by asking any number of questions to create a different dynamic.

For example you might ask any of the following: 

  • “What was the greatest learning for you this past year?”
  • “I have had a real challenge with X this past year. I wonder if anyone would care to give me some advice to address this problem.”
  • “Would anyone be open to playing a game, watching a movie, or telling their favorite holiday story?”

Notice that you have to recognize what is going on in the conversation and then do something to change the dynamics in the situation. You can’t manage the dynamics that you can’t see.

“The Put-Down Artist”—Sometimeswhen familiesget together, there is one person who takes it upon him or herself to provide negative feedback to others. They seem to believe it is there solemn duty to provide constructive feedback, offer criticism, or make denigrating remarks in front of everyone present. Such behavior definitely creates an atmosphere of discomfort for everyone. It also fosters disrespect, frustration, and strong emotional feelings on the part of the recipient. Such behavior also forces family members to take sides.  I have often wondered why some individuals would engage in this kind of behavior. Most of us would have the common sense to offer others the benefit of our perspective in private rather than in public. Perhaps this is a tactic for gaining a sense of superiority of self or an attempt to put the other person down with the intent of elevating oneself in the eyes of others.

What You Can Do - When being around this type of person, it is important to select and remember an intent or purpose for engaging in any conversation with this individual. I decide beforehand that my purpose is to maintain a respectful relationship with that person and their family members. Then, when they engage in their usual antics, I am not reactive to the negative feedback they offer. I can then thank them for their feedback and not be affected by their negativity.

You should also remember that when people offer negative feedback, what they offer says more about them than it does about you. They are sharing their perspective of a situation. You might try asking for facts, evidence, or specific examples of the feedback they offer. Don’t be surprised if they don’t have any support for the feedback they offer. If this is the case then what they are sharing is based more on their opinion or view than what current reality may be. 

“The Winner”—Someindividuals have to be right no matter what. It doesn’t matter if you have information or evidence that runs counter to what they are proposing. You are “wrong” and they are always “right” particularly when it comes to topics like politics. Sometimes such conversations make you wonder if these individuals are capable of any type of rational or critical thought. You need to recognize that they are not. To be wrong would run so counter to what they think or who they are that they just can’t accept any other view outside their own view.

What You Can Do - Don’t take what they say personally. Recognize that they may be incapable of rationally reasoning through an issue because of their personal commitment to that idea. When I find myself discussing an issue with such an individual, I find it easier to offer some fun statements and to abandon any notion of coming to a more shared rational perspective.

Here are some fun statements:

  • “That’s interesting!”
  • “Oh, I’ve never heard that before. Can you send me a link so I can read more about that?”  (Of course they never will.)
  • “I really like to know how you arrived at that conclusion.”


The holidays with family and friends can be a great time of year or can be quite challenging. If you can remember to observe the dynamics of any conversation, to have a positive intent, and to accept the irrationality of others, then you can not only maintain your sanity, but also maintain the respect necessary to build more positive relationships.  

Happy Holidays!! 


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