A Jewish Professional’s Guide on How to Have Hard Conversations

During a time of division in the Jewish community, these suggestions will allow us to see the humanity in one another while honoring our differences.

It’s no secret that we’re living in polarized times. Studies have found that America is at its most divided point since the Civil War. A poll after the 2016 election found that 16% of Americans had stopped talking to a close friend or family member over politics. That suggests the unraveling of 50 million relationships.

It often feels like every day, there’s something else in the news that leads to some sort of rift, whether about gun control, abortion, immigration… the list goes on. For the Jewish community in particular, the sharpest divides often center around Israel/Palestine. Jewish communities on campus are splintering and friendships are ending. Jewish professionals are asking themselves if they can work in an organization if their views don’t align. Parents and their adult children find themselves wondering if they should just stop talking about the conflict to save their relationships.

As program director at Resetting the Table, an organization committed to dialogue and learning across charged political differences, I have worked with communities across the country embroiled in these very conflicts. Over the past decade, Resetting the Table has developed a rigorous facilitation model rooted in research and practice from an array of disciplines, and oriented toward supporting people to investigate their differences and transform them into a source of stronger relationship and communal and social cohesion.

For many of us, including at Resetting the Table, the year since October 7 has brought into sharp relief both the profound need and massive challenges for the work of building productive communication across differences and divides. In the face of trauma, shock and grief, many of us have been anguished by the war on the ground and the proxy war that has erupted here, on campuses, on social media, between groups and increasingly within the Jewish community.

Based on my experience facilitating and training constituents at campuses, synagogues, young adult spaces, Jewish Federations and more, I’d like to share some tips from Resetting the Table’s facilitation model that you can utilize in your own life and conversations. The tools I will discuss can be applied in many types of conversations but, given the questions and requests Hey Alma has received from its readers, I’m going to frame advice around an intentional conversation you are seeking out with someone you care about.

I couldn’t possibly talk to them…can I?

In our increasingly siloed world, it is rare that we engage with people who hold beliefs and viewpoints that are different from our own. Moreover, when our social circles and the media we consume reinforce our own deeply held convictions, it can make the ideas and the people with whom we disagree, unintelligible to us, often leading us to wonder, “how could they possibly believe something like that?”

It is particularly painful when the person with that difference is someone you love. It can be hard to believe that this person could be in such a different place on an issue you care about. It’s possible that you might feel they have crossed a red line and having a conversation would be too difficult.

First and foremost, take care of yourself and assess your own desire and ability to take in what the other person has to say. You do not need to enter into a conversation that puts you at risk. Setting healthy boundaries is important.

That being said, we are in a societal moment where many of us are holding our red lines pretty close to ourselves, unintentionally conflating the people with whom we disagree with the worst possible actors. See if you have some space to push beyond the conversation you think you can have and may be able to listen to someone share ideas that feel a bit outside of your comfort zone.

Know your role, know your goal

Before you enter into a conversation, consider your goals.

We have found that there are many goals that might draw someone to a conversation across differences: the desire to heal a relationship, to be witnessed and heard, to learn, to persuade and more. All of these are valid reasons. In order to set a conversation up for success, it’s important to know your own goals as you enter.

If your goal is to convince someone to see the issue your way (which again, is a legitimate goal!), you must be open to listening to them if you want them to listen to you. If you do not have the capacity to listen and take in their point of view, or you will feel like the conversation will be a complete failure or waste of time if they do not agree with you in the end, then you may want to hold off for now.

Once you have clarity on your goal and buy-in for yourself, extend an invitation to the person you have in mind. Ask them if they would be willing to discuss the topic and tell them you’re interested in hearing what they have to say. Informed consent on both sides will increase the likelihood of a satisfying conversation. 

Do some prep work

In advance of sitting down to talk, it can be helpful to gain some understanding of what ideas and information others might be bringing to the conversation. In our highly polarized world, it’s imperative that we make the effort to seek out information from multiple perspectives. Take stock of your own biases and perception gaps, of the political slant of the material you consume. Seek out the best versions of the arguments on both sides (yes, even the side you can’t stand). Then find the ugliest versions of the arguments on both sides (yes, even your own), so that you discover where your own opinions might fall short. Reading information and arguments from an opposing viewpoint might feel tough, but exposing yourself to others’ perspectives in advance will help you not only be more effective in your conversation but critically it can help you understand the concerns, convictions and beliefs that someone else is sitting with.

The conversation

Here’s a roadmap, drawn from our framework at Resetting the Table, to guide you through a conversation across difference. As I mentioned before, you can utilize these tips in a multitude of settings, whether you intentionally set up the conversation or you find yourself in one accidentally.

Step one: Invite your interlocutor to share their perspective. Do your best to pause your own reactions and stop preparing your next argument. Slow down and listen.

Step two: Shift from a leading posture to a following posture. Ask questions to draw out what matters most to them. This will mean not saying what you think in response to what they said. It also means not asking a question to challenge them or poke holes in their argument. Your goal is to get inside their lens and ask a question to understand more about how they see the issue at hand and why it matters. If they said something was frustrating but didn’t say why, ask about it. If they keep repeating a word, ask about its importance. Try to uncover what matters most.

Step three: Demonstrate that you have understood them as they wish to be understood. Go beyond saying “I hear you.” Prove to them that you understood the heart of the matter — reflect the points that are most important and the reasons they care. It might sound like, “Let me see if I get it. For you, it’s this, this and this. Did I get that right?” Keep at it until they confirm that you got it right.

Go into the conversation expecting that you will not get it right on the first try! More important than “getting it right” is communicating that you want to understand.

Step four: Share that you see this differently. Share your opinion, offer a challenge or ask a question. And then try to identify the primary difference in your viewpoints and how you each relate to that difference.

Step five: Talk about that difference(s). You may be surprised that when you identify your actual differences, you realize that you are not as diametrically opposed as you thought. You’re not stuck in a pattern of “us and them.” You see something differently and you can explore that together. Return to steps 1-4 as new topics arise in the conversation.

What’s next?

Following these guidelines does not mean that you will agree at the end of the day. Nonetheless, this process maximizes the likelihood that you can understand what is at the heart of the issue for another and express what’s at the heart of it for you.

At Resetting the Table, we have found over and over that when people take the time to pause their own reactions, follow what’s important, demonstrate that what’s important has been rightly understood and then go toward their differences, they come out of conversations with a more accurate understanding of one another as well as of their differences. Our differences remain but lose their power to divide. More often than not, they walk away feeling closer to each other, learning from each other, even laying the foundation to stretch, to impact each other’s thinking, or to work together to solve problems.

In this time of teshuvah, may these suggestions help us return to our loved ones and communities, and allow us to see the humanity in one another while honoring our differences.

Rebecca Powell discussed these principles and more with Rabbi Rena Singer, Ginna Green and Emilia Diamant during our panel, Repairing Relationships in a Post-October 7 World. You can watch a recording of the conversation here.

Rebecca Powell

Rebecca Powell (she/her) is the Program Director at Resetting the Table and a long-time facilitator and experiential Jewish educator. When she's not navigating tough conversations across divides, you can find her spending time with her husband and two young kids or seeing as much theater as babysitters will allow.

Read More

A Yom Kippur Blessing for the Future

Even those who are living outside of the societal norm of “partnered-and-parenting” care about Jewish meaning, history and legacy. This prayer is for us.