How to Handle Difficult Conversations Over 50

By Susan “Honey” Good

Handling a difficult conversation on the telephone or in writing usually spoils the best-laid plans of reaching a positive conclusion. Words during a phone conversation between people often get lost in translation and written words, read over and over, can live in the back of one’s mind indefinitely. Therefore, an actual face to face conversation, though potentially difficult to handle, is your best chance for a positive and constructive outcome. This is essential in learning how to handle difficult conversations over 50.

A difficult conversation takes a certain skill and mindset because, obviously, no one wants to hear something negative about themselves and it is even harder being the bearer of that type of news. There are also particular situations that one may find unforgivable in which your best action is less reaction.

I have tried having phone conversations, face-to-face conversations, and writing notes personally. I always find that I am more in control and positive when I sit down across from a person with a positive goal, that both of us will walk away feeling emotionally happy and unencumbered.

These are my best tips for having a productive conversation:

Intention. You want to begin the conversation in a non–confrontational manner and discover if maybe, just maybe, you have misinterpreted their actions. If that is the case, be sure to tell them that. People do have different viewpoints, and after the conversation, you will have time to decide if you are able to blend your viewpoints.

Validate. You know you are eager to know ‘why’ they said what they said or acted as they did. Validate their feelings by telling them you want to understand where they are coming from and their unique point of view, but never attack.

Eye Contact. The importance of eye contact is critical. You are telling the person you care, and you are looking into their eyes as they share their feelings. Listening to a person’s every word and acknowledging their expressions actually empowers you.

Handling Their Story

Be open. Be present. Actively listen to their every word. Do not interrupt. Be respectful. Listen to your heart; it knows. Now you have an understanding of the other person’s views.

Ask questions and answer questions. Never hedge on your questions and listen to their answers, especially what is not being said.

Telling Your Story with Honesty 

This tends to be the most difficult part of handling difficult conversations and expressing feelings that are uncomfortable. However, I do believe there is a correct way to go about it.

Be Frank. State your message in a straightforward manner by focusing on the effect the situation has had on you, not the other person. This is key to handling a difficult conversation.

Express emotion. Share your feelings; tell the person you are angry or hurt or sad or in disbelief.

Always speak your truth. You don’t want to give the other person negative food for thought. Their perception of you may change because of your silence. So, work up the courage to learn how to handle difficult conversation over 50.

Unfortunately, there may always be situations with your family, co-workers or friends that have deteriorated, at least at the moment, to the point of no return. Situations that have gone on for years that have exposed you to too many hurts, too many unkind words, too many betrayals or too many intolerable disappointments. When this is the case and your tolerance level is exhausted, walk away. Recognize that any further discussions may lead to more upheaval and that your only option to protect yourself from harm’s way is your silence. Listen to your heart. It knows.

And then there will be situations when you so dearly want to have that difficult conversation in order to resolve all problems but the other party chooses silence. In other words, they close down and want no part of a relationship with you. That’s okay, too. I have been told by others facing this sad situation that after a time they have come to realize this is not about them. It is about the other person.

So, darlings, relationships must be watered and nurtured in order to grow like a beautiful flower. When they begin to droop it is important to ‘talk,’ no matter what the situation. Be the bigger person by confronting all the relationships that mean the world to you. Learn how to have that difficult conversation over 50.

Susan “Honey” Good is the founder of HoneyGood.com where this blog originally appeared. The site is a collection of lessons learned, life advice and insights from not only her, but from a fantastic group of contributing writers, each adding their own spice to the recipe. Honey Good.com representing “a family tree of women” — wives, mothers, daughters, granddaughters, mothers-in-law, daughters-in-law, sisters, aunts, cousins and girlfriends — coming together to talk about what makes them tick as well as what they have in common. Honey Good discusses life experiences with wisdom, humor and intellect, enabling all to attain a “Honey Good Style of Life.”