Sign In Forgot Password

How to Have a Hard Conversation

09/01/2021 01:03:12 PM


Rabbi Brent Spodek

We are fast approaching the Days of Awe and the public celebration of Rosh Hashanah and Yom Kippor. 

In many ways, those holidays are the culmination of work that we are called to do all during the Hebrew month of Elul - the work of teshuva

Teshuva is often translated as repentance, but more accurately can be thought of as return, particularly in the context of our relationships. 

Right now is a moment when you might be able to do teshuva, might be able to bring some beauty and repair to an important relationship that has been strained, or even ruptured. Whether the person is sitting next to you or on the other side of the world, here are some resources to help you have that conversation.

1. The final action is in the first thought. 

סוף מעשה במחשבה תחילה

Before picking up the phone, it’s essential to do a little heshbon ha-nefesh (חשבון הנפש), or soul accounting. What do you hope this conversation will accomplish? It probably won’t be useful to have a goal of getting your point across or declaring who is right. Simply “speaking your mind” is unlikely to be helpful; can you try to heal and grow the relationship. Is that something you really want to do? Do you have the time to invest in a long conversation? Does your partner have the time?

2.  Compassionate Curiosity

אֵיזֶהוּ חָכָם? הַלּוֹמֵד מִכָּל אָדָם

Engage in a little compassionate curiosity about yourself and your partner. The mishnaic sage Ben Zoma famously teaches “Who is wise - one who learns from everyone.” Even their opponent, even themselves.

Be honest with yourself. What “buttons” of yours are being pushed? What assumptions are you making about your partner’s intentions? You may feel intimidated, belittled, ignored, disrespected, or marginalized, but be cautious about assuming that this was the speaker's intention. Impact does not necessarily equal intent.

Now think of them. For a moment, think in the voice of the person receiving your call. What stories, accurate or not, might they be telling about you? How might they feel hearing your voice? You don’t need to abandon your thoughts, experiences or feelings to have – for a moment, at least – compassionate curiosity about their experiences. 

3.  Make the call

וְלֹא הַמִּדְרָשׁ הוּא הָעִקָּר, אֶלָּא הַמַּעֲשֶׂה

If you are ready, don’t plan to start the conversation tomorrow. Now is the moment of adrenaline. Imagine what are you going to say when they answer the phone. Here are some possibilities:

  • Hi, it’s Josh. Do you have a minute? I’ve got something I’d like to discuss with you.

  • Hi, it’s Jessica. I’ve been feeling some tension between us and want to try to make it right. Is now good for you?

  • Hi, it’s Bob. Listen – that thing that happened? I think we might have experienced it in different ways. Is now a good time to talk about it?

  • Hi, it’s Stephanie. Do you have a minute to see if we can see eye to eye about that thing that happened? I really want to hear your feelings about this and let you know where I’m coming from.

Let your partner talk until she is finished. Don’t interrupt except to acknowledge. Whatever you hear, try to not take it personally; simply absorb what they have to say. Try to learn as much as you can in this phase of the conversation. You’ll get your turn, but don’t rush things.

4.  Self Control

אֵיזֶהוּ גִבּוֹר, הַכּוֹבֵשׁ אֶת יִצְרוֹ

Can you be your own master? Ben Zoma goes on to teach, “Who is mighty? One who has self mastery.”

No matter how well the conversation begins, you’ll need to be aware of yourself, your purpose and your emotional energy. Before you start the conversation, breathe and locate your center. Notice when you get knocked off center – and take those opportunities to teshuva and to return to your own center. This is where your power lies. 

You might want to scream at your partner, and you might have every right. Perhaps they attacked you or betrayed you or abandoned you. Perhaps they are terrible people. This might be the hardest step of the whole process - if you want them to hear your truth, you have to hear theirs. Even if they are deplorable. 

Centering is not a step; centering is how you are as you take all these steps. 

5.  Acknowledge

אלו ואלו דברי אלהים חיים

The most important story in the Talmud teaches אלו ואלו דברי אלהים חיים. These and these are the words of the living God. You might be right - and they might be right too. 

Let your partner know you’ve heard and understood her. Try to understand her so well you can make her argument for her. Then do just that. Explain back to her what is really going on for her. You might begin by saying, “It sounds to me like….” Honor your partner’s reality, so that they might honor yours. Remember that acknowledgment is not the same thing as agreement, and it might be worthwhile to keep them separate. Saying, “this sounds really important to you,” doesn’t mean “I think you are totally right.” 

6.  Say Your Piece

אמת מארץ תצמח

When you sense your partner has expressed all his energy on the topic, let them hear you. What don’t they see about your reality? Clarify your position without minimizing theirs. Can you imagine yourself saying, “I hear where you’re coming from; I’d like to tell you how this feels for me”?

7.  Next Steps

הבאת שלום בן אדם לחברו

So now what? There is special merit in achieving peace between people, and it can be done – but is not easy. After you’ve heard from your partner and shared from your heart, there might be room to think about next steps. There also might not - this conversation might be as far as things are going to go. Can you ask your partner what they would like to see happen next? Can you articulate what you would like to happen next? 


In the essay “Women and Honor: Some Notes on Lying”, Adrienne Rich teaches that “the possibilities that exist between two people, or among a group of people, are a kind of alchemy. They are the most interesting thing in life.  The liar is someone who keeps losing sight of these possibilities.” You are talking to your partner because you believe there are yet unrealized possibilities for connection between you and them. Good luck in re-building those connections.


With gratitude to resources which were useful in preparing this guide:

Mon, October 18 2021 12 Cheshvan 5782