How to Make Hard Conversations a Little Easier

Tips on how to handle tough topics

Posted Oct 15, 2020

iStock/ fizkes
Source: iStock/ fizkes

Difficult conversations: We all have them. They come up because things change, especially during a pandemic. We’re dealing with layoffs, work from home, back-to-school, forced isolation or forced togetherness, and a controversial presidential election. Our life goals have probably been reviewed, renewed, and revised. We may now want to start a family sooner, or later, than we did before. We may find we’re in the middle of a turbo relationship that’s moving too fast or a relationship too distanced to reunite. And talking about any of this with someone significant in your life will not be easy.

But no matter how difficult the topic, here are some strategies that can lower your anticipatory anxiety and help you feel better about the outcome. Let’s start at the beginning.

Preparing for a hard conversation

1. Be honest with yourself about yourself. If you become intimidated easily, try too hard to please, become aggressive when you are contradicted or tend to take things personally—own it. Know it so you can spot it and control it. But don’t feel defensive about it. You’re a package deal and so is everyone else. 

2. Remember who you are talking to. Don’t expect your Uncle Milton’s politics to be different this year than last year. Don’t expect your grandmother to understand IVF. Don’t expect your sister to suddenly become an activist. Be real about them and the conversation will be realistic.

3. Make a list of the points you want to make and keep the list short. Underwhelm the discussion or it will drown in opinions, emotions, and rhetoric. Besides, a few good points will be remembered, a long list of points will not.

4. Have a solution for every problem. Take a look at the list, and for every problem on there, include a solution or two to suggest. It lets the others know you are interested in a satisfactory conclusion to the discussion, not a forever fight.

5. Practice, practice, practice. The rehearsal will make you sound more confident and feel more comfortable.

6. Control the environment. If you can, pick the time and place for the conversation so you will feel more in control. And don’t put off talking about the problems because it will cause you to worry more than you need to.

Having a hard conversation

1. Set and have a calm tone. Do this for yourself and for your conversation partner to help ‘set the mood’. You can do this by saying, “I’d really like to hear what you think about…”, “I’d really like to understand your thoughts on….” or, “I’d really want you to know what I’m thinking…”

2. Try to start discussions with “I” statements, not accusing “you” statements. I need more support” invites empathy. “You don’t give me enough support" invites defensiveness.

3. Set up ground rules. These can help if you’ve tried this conversation before with the same person and want a different outcome. For some, taking turns becomes the ground rule. For others, no interrupting, no yelling, or no name-calling are ground rules.

4. Try ‘active listening’. That means you repeat back what you’ve heard. You are not only letting the other person know you understand their position, but you’re also giving them a chance to hear themselves.

“So you would never vote for that person.”
“You feel you could never consider ovum donation.”
“You say you will never forgive him."

Don’t be surprised if they amend or even take back what they have said once they’ve heard it out loud.

5. Take the ‘active listening’ one step further and ask for more. Use this debate technique: ask them to tell you even more, and be attentive. You will now be leading the conversation and can introduce your point of view or information as part of the discussion. They will usually follow your example and try to listen with interest rather than debate with hostility. Hopefully, the conversation will then end the way you hoped it would.

Problems that may arise during a hard discussion

Suppose the hard discussion triggers accusations, arguments, or even tears. Suppose it’s even harder than you thought it would be. Here are three emergency strategies:

1. Pretend you are an observer, not a participant. Pretend you are writing a book or film script and you will use this conversation in the book or script. Pretend you are already telling your best friend about the discussion. In other words, step back emotionally and give yourself some psychological distance when up close and personal becomes too intense.

2. Don’t take it personally. Recite this poem to yourself:

Everything they say and do
Is information about them, not you.

In other words, don’t take their reactions personally! The discussion may be disappointing, hurtful, or surprising, but you’ve now learned more about them and sometimes, in personal and political discussions, that knowledge is the hardest part!

3. If you become upset or hurt, acknowledge it. In other words, label the other person’s statement:

“That sounds harsh…."
“That really hurts my feelings…”
“That is not what I expected….”

Until you give feedback, your discussion partner may not even realize how they sounded or the effect they are having on you. After all, their response may reflect cultural differences, generational differences, informational differences, personality differences, or experiential differences and not their feeling about you.

After a hard discussion

Most of us get more perspective on hard conversations after some time has passed, so pretend it’s six weeks, six months, or even six years after the difficult discussion. Will it still matter to you? Will other opinions or others’ advice still be relevant? Will those others still be part of your life? If the answer is “yes,” try to understand their point of view. If the answer is “no”, compartmentalize the hard conversation and label it “over."

If you want to maintain an easy relationship with someone after a hard discussion, follow-up with a call, text, or email to let them know that they have given you a lot to think about. I find, in my practice, that the happiest friends, family, and couples don’t always agree on life decisions or politics, but they agree to disagree or avoid areas of disagreement completely when they can. So even if the discussion didn’t end well for you, the relationship can go on if you choose.

And finally, ask yourself what the hard conversation taught you about yourself. Are you more sensitive or less sensitive than you thought? Are you more patient or less patient? Do you now think you would handle the conversation differently—or not? Did you learn any good approaches to hard conversations from whomever you were talking with?

Having hard conversations is part of life. With patience and practice, it can be something you do with ease.