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Four Things You Need to Do Before Starting a Difficult Conversation

Besides, of course, taking a deep breath . . .
Photo Credit: Andrea Rose

Photo Credit: Andrea Rose

A few months ago, I found myself anxiously scouring the web, looking for answers on how to prepare to have a difficult conversation with my mom. As a 25-year-old woman, I still lived in fear of my mother’s opinions and judgments when it came to things such as my love life or even how I spent my weekends. I knew I needed to set clearer boundaries between my life—and the way I chose to live it—and hers, and the longer I let those needs go unspoken, the more our relationship suffered. Even though the topic was simple, it had so much potential to go wrong.

Despite my fear of this talk, I also knew the upside would far outweigh the immediate pain and discomfort of having it. Things needed to change between my mom and me in order for us to have a healthier relationship, and the only way that was going to happen was to confront it head-on. But that didn’t make it any easier to go through with. I would go back and forth, volleying between chickening out and heedless impulses to just call her right then and there. I overanalyzed every possible outcome of the situation, and the tension and dread only continued to build.

If you’ve ever faced a difficult relationship sit-down—you know, the kind that makes you feel vulnerable and makes the other person feel vulnerable and usually ends in tears—you can sympathize with the anxiety I felt. But with careful planning and preparation, I was finally able to face my mother and have that much-needed relationship talk. What I have learned since is that having a difficult parley does not have to turn out badly and certainly does not have to be a source of so much stress. There are things you can do to prepare for those conversations that can help you achieve your desired goal: a happier, healthier relationship.

I asked Aldo Civico, Ph.D., founder of The International Institute for Peace at Rutgers University and lecturer on conflict resolution, to weigh in on the best ways to prepare for a tough relationship talk. 

01. Wait until you have cooled down.

You may be extremely angry, hurt, sad, or frustrated. These emotions are the typical catalysts for a relationship powwow, but it’s important to not let these emotions hurt your chances of having a calm and collected conversation. Dr. Civico says that in his coaching, he always reminds his clients that they can and should feel their emotions, but they shouldn’t let their emotions take over and get the best of them. “Whether you are dealing with a difficult boss, facing a crisis in your romance, or your kids are giving you a hard time, losing your cool only signals your weakness,” he says. “The risk is that you are giving your power over to the other.”

So give yourself time to sort out your feelings before initiating a talk. “Get some detachment from the situations, and try to become more aware of what’s going on within you and around you,” Dr. Civico says. Instead of calling the person up right then and there or addressing the issue in the heat of the moment, do something that helps you wind down and relax. Try exercise, meditation, or any craft or hobby that allows you to mull things over and gives you a sense of peace.

02. Write a letter.

Don’t worry, you won’t actually be sending it. But this was a really helpful way for me to get all my emotions out of my head and down on paper, instead of lying awake at night with a racing mind. 

After cooling off, take out a pen and paper, and begin writing whatever you feel. Getting everything out will not only help you pinpoint what you want to say, but it will also help you determine what things you would like to avoid during your discussion.

“Once you write it, I always suggest letting it rest for a couple days and then examining it,” Dr. Civico says. “What’s actually true of what you wrote? What have you exaggerated? What assumptions are you making? What have you left out? What is it that you really want to get out from the relationship with that particular person? Responding to these questions will increase your self-awareness and in turn make you more resourceful to have a difficult conversation.”

03. Know what you want out of the conversation.

Before heading into my conversation with my mom, I asked myself, “What do I want out of this talk?” I felt overwhelmed because I knew I couldn’t control the outcome—I didn’t know how my mom would react or what she would have to say—but knowing that the talk had a purpose and that I had goals for our relationship (i.e., to have a healthier one) helped keep me focused and unafraid.

Dr. Civico agrees with this approach. “Being able to identify well-defined goals allows you to focus on what it is that you want to get out [and] what your priorities are,” he says. “Having well-defined goals will help you keep the eyes on the prize, which in turn will also help you manage your emotions. When you know what you are after, you are more in control of yourself.”

04. Seek counsel.

If you are feeling unsure or feel you need to practice what you want to say during your conversation, call on a trusted person in your life, or seek professional help. “Sometimes, instead of going through trial and error, it’s advisable to get some coaching in effective communication and emotional intelligence,” Dr. Civico says. “Most of the time, there is no need to go into therapy. Some training and coaching will give you the confidence and the skills you need to be empowered and effective.”

I find that it is especially helpful if the person you are practicing with knows the person you are going to have the real conversation with. It will save you time and energy in explaining context, as she or he is probably aware of tension and conflict you’ve had with this person. Your confidant can also be a great resource for refining what you want to say.

Moral of the Story

Taking the time to follow these steps helped me have a productive conversation with my mom, and I know it will help me overcome my fear of having these difficult talks in the future. They say “practice makes perfect,” so if there is a tough conversation you should be having, just go ahead and have it—trust me, there will be plenty more of these relationship confabulations in your future. Approaching each oh-so-needed relationship talk with intentionality and preparation will make you increasingly confident that they don’t all have to end in tears.

For even more helpful tips, check out this eight-minute video lecture by Fred Kofman, Ph.D., from on managing difficult conversations.