How to Have Tough Conversations Without Losing Your Cool

Of all the sobering texts that’ll stop you in your tracks, “we need to talk” may be the most jolting of all. It’s ominous, non-descriptive and emotionless. Worst of all, the recipient most likely has an inkling to what it’s about.

Maybe you’ve noticed a cool, distant attitude from your significant other this past week, or maybe you heard your roomie sigh with exasperation last night when she saw the dishes piled up in the sink. No matter what it is, those four little words never seem to be good.

And as for the sender, that dread is equally (if not more) apparent. Whether it’s your roommate, coworker, significant other or a family member, having an especially difficult conversation is hard. And that difficulty is amplified when the exchange is with someone you care about.

While confrontation is never comfortable, there are several approaches to make it a little less awkward and even more productive.

Decide what you want to happen

When someone in your life upsets you, it’s natural to move through the whole spectrum of emotions. You care about them and don’t want to jeopardize your relationship. However, you’re also flustered and champing at the bit to purge your frustrations and tell that someone exactly how you feel.

But according Chris Armstrong, a relationship coach of The Maze of Love, that approach couldn’t be more dangerous. “Understand what you want out of the conversation,” he says. “What is the end-state, or what do you want to happen from the conversation? Second to this, how will the person you are trying to talk to react to that end-state, and what’s in it for them? We often go straight from our version of what’s right and what needs to be said to emotional expression without thinking.”

Resist the temptation to approach the person you’re having difficulty with right away. Instead, collect your thoughts a few days prior and map out potential outcomes. If your roomie refuses to chip away at those piling dishes in the sink, will you offer an alternative solution (i.e. if you offer to do dishes each week, would she be willing to vacuum the common area)?

Bottom line: don’t go in unprepared.

Avoid the awkward set-up

When it comes to approaching the convo, passive-aggressive pre-meeting texts should be avoided at all costs, says Nicole Richardson, an Austin, Texas-based licensed professional counselor and marriage and family therapist. “Sending texts and emails like, ‘We need to talk,’ will get people anxious,” she explains. “Instead, invite them to take a walk with you or bring them to their favorite coffee in the morning. Set up an environment of care and openness.”

Instead, ask: What are they doing right?

Yes, your bestie continually bailing out on plans at the last minute is bumming you out—and for good reason. And while your gut instinct may be telling you to begin listing off each and every wrongdoing right off the bat, try focus on what they’re doing right first.

“People are more open to difficult conversations when you build them up while still addressing the issue at hand,” explains Dr. Nikki Martinez, a psychologist and licensed clinical professional counselor. “By telling people their strengths and what they are doing right, it will make them more open to hear the difficult topics that you are needing to address.”

Your friend being flaky is the issue at hand. But, you’re so bummed she’s missing out on plans because she’s truly the life of the party. Make sure she knows the latter first.

Address the issue, not the person

From the way he chews his food to his poor cubicle cleanliness to his lack of accountability, you have more than a few bones to pick with your coworker. But instead of launching an all-out personal attack, isolate what’s truly bothering you and leave the rest alone.

“Attack the issue and not the person. Only address what is wrong, not what is wrong about them,” advises Dr. Martinez. “This lets them know it is not a personal attack but rather an issue of resolving a matter to make a more harmonious work environment or relationship.”

The real culprit here is the fact that your coworker, in one way or another, might be impeding your work with his lack of accountability. Those harmless but annoying personal habits (the chewing, the hygiene) shouldn’t enter the conversation once.

Assume the first-person narrative

In addition to addressing the issue at hand rather than the individual, Richardson suggests alleviating much of the pressure you’re putting on the person you’re approaching with simple “I” statements. “Try phrases like, ‘I feel like our common area is getting a little messy’,” she suggests. “Avoid ‘you’ phrases like, ‘You are such a slob!’”

Transitioning the focal point of the conversation back to you will help to open her eyes to those wrongdoings in a much gentler, more democratic way.

Stay flexible

Although entering your difficult discussion with someone with a strategic game plan is pivotal, the real winner will understand that not all arguments are meant to be won, according to Stephen Frost, founder of   

“The person with the greatest flexibility wins,” he says. “By encouraging yourself to adapt your behavior within a situation, rather than allowing yourself to become channeled with a descent into anger and frustration, you can gain a significant edge. Just that knowledge about adapting is enough to start the sway in your own favor.”

So, when you approached your roommate about the piling dishes, maybe you didn’t anticipate her gripes about your loud music on weeknights. Or maybe when your significant other’s spaciness seemed to be the only problem, you didn’t anticipate that he was denied a promotion at work. Bottom line: Prepare for the convo, but try to stay as flexible as possible.

Of course, confrontations can be one of the clearest ways to pinpoint a relationship that may not be going so smoothly or that has simply run its course.

“You have a choice about whether or not to continue a relationship,” says Richardson. “ If you cannot come to a compromise that could work for you both, it may be necessary to evaluate if the relationship is healthy and able to meet both of your needs.”

Julia Sullivan is a freelance writer and editor in New York City. When she's not picking heavy things up and setting them down again (more commonly known as weight lifting), trying to prepare healthy meals in her doll-sized Manhattan studio or writing about the latest fitness craze, she chronicles her zany adventures as a new New Yorker in her blog, Jules & the City. You can also follow her on Twitter.