A field guide to hard conversations

The hard conversations are the necessary conversations.

Kristin Calabria
Those That Inspire
6 min readFeb 3, 2019

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Photo by rawpixel on Unsplash

People love to talk when it’s easy and light, when the stakes are low and there are very few opportunities for feelings to get hurt or people to be offended. Once you begin to ratchet up the intensity of the conversation, once you elevate the states, all of a sudden, words disappear — or more likely, people disappear.

Though I have become fluent in speaking through my own discomfort, thank you BFA Acting, I still struggle with the conversations that I think might not be what the other person wants to hear. It hurts my heart to know that I might instigate some not-great emotional or cognitive responses in another human. In times like these, I remember Brene Brown and her words of wisdom: clear is kind; unclear is unkind.

So how do we begin? How to we muster up all of our courage and engage in what we think might elicit an immediate negative response from the other person?

Do the prep work.

You must do the work. If you want to have the conversation you need to know why. Why are you bringing up this difficult topic now? Was there an inciting incident? Specifically, are there behavior patterns or concrete examples that might help the other person in understanding what you are talking about?

Write a list of talking points. Particularly when things get difficult, ideas run away from us. On your phone or in a notebook, have a list of things you need to say in the conversation. These might be things that you will regret if you don’t mention. You don’t need to say them all at once; naturally segway into each point. Allow the other person to respond as you introduce ideas. You must, however, know what your goal is, what you came here to do.

I also encourage you to brainstorm a few compassionate and kind ways to say uncomfortable observations. Instead of accusatory language (“you did this”), reframe those ideas into “I” statements (I feel X when you Y). These simple reframings will also help both parties to understand, even empathize, with each other.

You will never truly know what another person thinks or feels.

Let’s begin with a simple reframing. The belief here is that, especially if this is an intimate relationship (emotional closeness here being the key as opposed to physical intimacy), you understand the person you are engaging with. You can guess their thoughts and feelings and reactions because of the amount of time you spend with them, the hard work you put into learning who they are, the countless days and nights and months and years of building trust, of building that intimacy. So, when you are about to bring up a topic that feels like it will fall into the “negative” category with the other person, of course the initial reaction might be to avoid the conversation at all costs.

But, you can never truly know what another person thinks or feels. Thanks grad school for this learning. The other day in a psychopathology class, we had a discussion about lying and liars. We all lie. Some lies are bigger than others. Sometimes we lie to ourselves. Many times we lie to other people about how we feel or what we think because it is vulnerable to be real. Ultimately, the only person who knows what they think, how they feel, the way the might respond to a situation or conversation is the person themselves. We are just taking educated guesses and believing what the other person tells us.

Take the responsibility of determining how the other person feels off of your own shoulders. If you do enough prep work and approach the difficult conversation with the intention of coming to a resolution collaboratively, any guilt you might feel about inciting “negative” emotions in another person can dissipate rather quickly.

Be Honest.

We’ve gotten over the first roadblock to actually having the conversation and have decided to initiate. This is awesome. Congratulations — in a totally non-patronizing way. It is truly hard to muster up the courage and integrity to converse about challenging subjects.

But now, we’re in the thickest part of the woods.

Inside of the uncomfortable territory of having hard conversations, emotional reactions from both sides of the dialogue will most likely occur. This is natural. It’s a hard conversation. Tension was a given. What will not help is lying to soften the blow of the information you are trying to impart.

Lying is purposeful obfuscation of the truth. Lying is dancing around the hard conversation to preserve the image you think the other person holds of you. Lying is backing away from the challenging conversation because of fear.

Lying does not serve anyone.

But there is a massive difference between being cruelly blunt and tactifully, sensitively honest. This does not mean that the other person will not get emotional. Honestly, I find that vulnerability, truth-telling, dredge up more emotions. They are, however, the ones that lead to acceptance and healing and moving forward gracefully. In my observation, spite only happens when there has been lying.

This all comes back to Brene’s principle: clear is kind; unclear is unkind. While it might be “nice” or convenient to lie, you did not engage in the hard conversation to only half-find a resolution. This is what you will get if you only half-tell-the-truth.

Check in. Constantly.

Check in with yourself. How is this going for me? What am I feeling? Can I take a deep breath? Do I need to refocus? Am I being heard? Do I need to come up with a different way to impart information? Am I hearing the response of the other person or I am ploughing through my agenda? Can I be more responsive and present here?

Check in with the other person. How are they doing? Have the shut down? Are they engaging with me in a way that inhibits or continues conversation? Is there something I can do to encourage honest dialogue? Does the other person feel close or far away from a solution?

Why is the check-in critical? It allows both sides of the conversation to stay highly attuned to the other person. Dialogue is always about the other person. Conversation is always about the other person. Resolution seeking is always about the other person. When it becomes centered around “what I need”, “what I want”, “what I will say next”, the dialogue becomes a monologue.

The word-vomit, as I call it, in a heated conversation is a natural response when we think about biology. If the conversation is our stressor, fight/flight/freeze is a the body’s response to stress. Word-vomit, monopolizing a conversation, can be thought of as a fight mechanism. Therefore, if we check in with ourselves and take a breath, it will allow the other person a chance to speak. Mindful breathing can also help to neutralize our stress response.

Very few times will a resolution be reached if the conversation is one-sided. Open up the pathway for honest dialogue. Reach a resolution.

Reflect.

After the conversation finds a conclusion, take some time to reflect. I highly recommend writing everything down or using a voice memo to record your thoughts and feelings immediately following the interaction.

How did you feeling leaving the conversation?
Are there things you wish you would have said?
Is there something you wish you could take back?
Do you feel the need to apologize for any behavior?
Do you feel you are owed an apology?
Does the conclusion you reached feel good to you?
Do you need to do something else for closure?

These are all questions to start unpacking the event. Of course, as your mind works beyond the peripheral answers to these questions, more thoughts and feelings will arise. You do not have to take action on any of these items. Rather the aim is to understand your emotional and cognitive pallet in the aftermath.

The hard conversations are the necessary conversations. More often than not, avoiding these conversations will leave the other person more damaged when they inevitably find out what you were trying desperate to conceal. With practice, the hard conversations become less terrifying. Your body and your heart know what to expect. Like anything you do repeatedly, you become more skilled in time. So dive in. Get a little messy. Get better with every conversation.

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Kristin Calabria
Those That Inspire

Yoga Teacher, Wellness Expert, Clinical Psych @ Pepperdine, Founder of The B.R.I.D.G.E.