How to Transform Difficult Conversations Into Healthy Connections

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While sharing the dinner table with others is usually a time for chatter and connection, mealtime conversations amongst family or friends can at times become awkward. The potential is always there for friends and co-workers to say or do things that make us feel a host of negative emotions and even physical discomfort. The racing heartbeat, indigestion and headaches triggered by conflict can give way to more serious health issues.

Psychotherapist Terri Cole reframes the notion of boundaries to help her clients thrive, and she’s captured those insights in her book, Boundary Boss. Cole recognizes the significance of the brain and body connection, and often advises clients to check their physical reactions as a first step.

“A lot of us are very disconnected from our body wisdom,” Cole says, “And when someone says, ‘I don't know why I'm so mad right now,’ I ask them to think back. Maybe someone took credit for your idea in a meeting, and then you got a pounding headache.” 

Cole continues, “You felt threatened, and you wanted to say something, but you didn’t. Your body responded anyway.” A surge in cortisol, adrenaline and other hormones derail your body’s equilibrium, and you feel it physically, along with a host of harmful follow-on effects. 

How to have that conversation

In addition checking in with your body for clues about where boundaries are needed, Cole suggests reframing the notion of boundaries as “personal rules of engagement.” She says, “They are there to let other people know what's okay and what's not okay with you.” 

Cole knows from seeing patients for decades that it takes more than a formula to change the way we think and act, but it helps to know what works when you’re ready to try. Boundary Boss, where Cole provides more insight, includes these steps to success.

Figure out where a boundary needs to happen, starting with a “resentment inventory.” Cole says wherever you are holding resentment in a relationship, usually a need is going unmet, a boundary is being violated or a boundary needs to be established.Make a list, and then categorize those items as preferences that allow for compromise; limits, for which you might make an occasional exception; or deal-breakers. 

Deal-breakers are things we can’t live with—or without. Cole says, “You need to know what those things are to even try to get your needs met,” she says, adding, “Your preferences, your limits and your deal-breakers are not a burden to others. They make you uniquely you,” and denying them to please someone else also denies who you are.

Decide the best time to have a conversation. Cole gets straight to the point: “If the person you need to speak with is not a morning person and you are, don’t start texting at 6 a.m.” 

Practice, before you have the conversation. “Script it. Role-play with a friend. Do it in the mirror,” Cole advises. “Left to your own devices in the moment, you might freeze, or you might explode, or you might get run over by emotion,” and find yourself unable to talk.


When it’s time to ask, keep it simple. Cole recommends starting with the sentence, “I have a simple request.”  

Skip the preamble, and once you’ve made your request, don’t over-explain it or justify it. Cole recognizes that it can be hard to not to elaborate, especially when you want the other person’s approval. 

Let the other person have their reaction. “Give them the space to digest and respond to your request. What they think of you setting a boundary is on their side of the street, not yours.” From Cole’s perspective, the conversation is “the most loving thing you can do—you’re protecting the relationship by not silently staying angry or complaining to someone else.”

What makes a Boundary Boss

Cole has more tips for “hard” conversations and signs that you’re making progress (even when you think you aren’t).

Check your expectations. Cole advises against anticipating what the other person’s reaction could be. She explains, “Boundaries are not like levers to control others. Your healing lies in the fact that you’ve decided to say how you feel, what you think and what you want, and it matters enough that you’re willing to feel a little uncomfortable and do something you're afraid of.” 

Letting go of anticipation can turn a hard conversation into an opportunity for honesty, acceptance and even empathy. Nevertheless, Cole says that a little pushback shouldn’t be surprising, and it doesn’t mean you’ve failed. “Have faith that you and your relationship are not that fragile,” she says, “If you assert boundaries gently, with love, and your relationship blows up, then it was built on your compliance, not authentic compatibility.”

Reconsider “conflict.” When there’s disagreement, Cole suggests revisiting what your boundary is about. If it’s a preference, that’s an area where you’ve already decided you could compromise. Cole gives an example: "If I really want to leave something at 10 and my husband really wants to stay until 11, I can compromise on that if it’s important to him, and it’s not degrading to me.” 

Redefine success. Cole says as long as you’ve followed through on your side of your boundary, you’ve succeeded. If your request isn’t honored, revisit it. “Acknowledge their reaction and explain your reasons for the boundary by providing more context,” says Cole. “Maybe you’re exhausted, or you didn’t have the money to do something. You can say it’s your job to do what you need for yourself.” 

It's never too late. Cole also wants us to understand there’s no statute of limitations on requesting a boundary. All it takes is a brief preface, like one that Cole suggests: “I was thinking about what happened last week. At the time, I felt like I couldn’t say anything, but now I’d like to make a simple request.” 

It takes practice. Cole offers this perspective on “successful” conversations: “Think about boundaries like a foreign language that nobody ever taught you. You wouldn’t feel bad about not knowing it. You’d take a class or get a book or take other steps to learn it, and you’d give yourself time. Boundaries are the same: You don’t need to master everything all at once.”