How to Start a Difficult Conversation

How to Express Negative Feelings Without Harming Your Relationship

Imagine you’re a small business owner. A difficult issue comes up and it involves one of your most valuable customers. You know each other for years and they’ve been there in the good times and the bad times.

5 Tips for Starting a Conversation that You’re Dreading

But something has come up and you need to have a sincere talk with them. So you pick up the phone. Then what?

Do you start yelling at them?

You could.

You might even get away with it for the time being. But odds are they won’t be your customer for much longer.

My guess is, you might want to try something else first.

Maybe first you will ask them how they’ve been. Perhaps you remember something they told you the last time you spoke, and ask them how that went. Maybe you even ask them how their kids and spouse are doing. Is their mother better now?

Then, you might say something along the lines of, “Listen, maybe it’s not a big deal, but…” And then you would explain the issue. No need for sugarcoating. You’d just be mindful by taking their feelings into account before getting to the chase.

Do We Treat Our Loved Ones the Same Way?

Couples in trouble tend to handle disagreements in the wrong way. Usually, one starts criticizing and of course the other feels attacked. They start defending themselves or hitting right back. More often than not, they end up even more frustrated and angry at each other, while solving nothing.

When they figure out this doesn’t work, they try the same thing, even harder. Eventually they give up on the idea that things can be solved calmly without one or the other getting upset.

So with time they start avoiding talking, even about smaller issues. Unresolved conflicts start to pile up. This is not a good plan because this is what happens when small problems are being swept under the rug.

Coming back to our analogy from the example in the beginning of this post, it simply isn’t fair to treat your spouse less kindly than you would other people, in our case your valuable customer (who, by the way, doesn’t share the same bed with you).

Successful couples have learned to approach to each other in a non-threatening way, while inviting insight, cooperation, and understanding.

You can do that too. Here’s how.

Calm Down

Avoid starting a conversation when you are stressed or angry. Calm down first. Don’t let your ancient brain—the amygdala—run the show. It never ends well.

Start Slow

Say something nice first. Thank your partner for something or simply share a kind (and sincere) observation.

“You looked nice in that shirt today,” is an example of such a nice little thing.

Sometimes you’ll feel that a conversation might be particularly difficult for your spouse. In that case it’s always good to be mindful and further soften up your opening by using something that I call Lt. Columbo’s humble disclaimers.

Talk About Yourself

Focusing on the other person invites resentment because “you” sentences lead to implied criticism and blaming.

Instead, talk about how YOU feel.

Bad: “You didn’t pay the bills again!”.
Good: “I feel upset when you miss paying the bills because…”

See the difference?

Be Specific

It’s a good practice to be as specific as you can about what bothers you. This way you will avoid criticism automatically.

Secondly, when you are specific, it is easier for your partner to relate to a specific event or series of events in the past. It will be easier for them to pay closer attention next time, and adjust their behavior in the future. By the way, this works with kids too!

One way of doing that is by using phrases that contain when you and combine them with stating how you feel about it.

“When you do _______ I feel like _______.” Or you can start the other way around “I feel _______ when you _________.”


Bad: “You are always late!”
Good: “When you are late without giving me any advance notice, I feel taken for granted. I’d like you to….”

The “when” makes your complaint specific because you avoid words such as “always” and “never” that build resentment. They tend to attack the personality, rather than addressing the behavior.

Talk About What You Want

Talk about what you want, instead of saying what you don’t want. That’s because our brains are not designed to deal with negations very well.

Instead of saying what you don’t want, say “I would like you to …”


Don’t: “I don’t want to go to shopping today.”
Do: “I would rather go to the beach.”

Don’t: “You need to be more responsible about spending money.”
Do: “I would like to know that we are on track with our savings so we can buy a new house as we agreed.”

Read this post if you want to learn more why negative statements (about what you don’t want) actually lead to more of what you don’t want.

Your Turn

Think of the last time you were complaining. Close your eyes, and imagine how you could approach your spouse differently, following the five tips in this post. Commit to trying this the next time you want to complain to your spouse.

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