Lesson 8

Master difficult conversations

Lesson 8

Master difficult conversations


Gain practical skills to turn the most difficult disagreements into productive conversations. Learn techniques for listening, communicating, and getting conversations back on track if they start to go awry.

Our Picks

Recommended Videos

  • Hugo Mercier, How can you change someone’s mind? (hint: facts aren’t always enough, TED-Ed (4:39). Mercier, a psychologist, explains how learning about our conversation partner allows us to speak to them more persuasively. “Arguments are more convincing when they rest on a good knowledge of the audience, taking into account what the audience believes, who they trust, and what they value,” he explains. In order to communicate most effectively, we ought to make sure our message will resonate with the values held by the person we’re speaking to.
  • Crucial Conversations, VitalSmarts Speakers (14:57). Joseph Grenny, the bestselling author of Crucial Conversations, provides insight into how to successfully navigate difficult conversations. Grenny emphasizes the importance of recognizing that “how you feel during a crucial conversation is not a direct function of what you just saw, heard, or experienced.” He urges us to recognize the way we interpret events and intervene before we are led astray by our emotional responses.
  • Why facts don’t convince people (and what you can do about it) Social Good Now (2:46). This video summarizes several forces that make it difficult to have productive disagreements. It reminds us that we can set ourselves up for greater likelihood of success by focusing on our similarities and demonstrating intellectual humility, 

  • Being a good listener, School of Life, (4:57). It’s easy to find advice on how to become an excellent speaker. But how can we listen better, and why should we bother? This video spells out how good listeners make other people feel heard and appreciated.

  • Kid President is over it!, SoulPancake (5:09). In this funny video, Kid President (a.k.a. Robby) reminds us that “you don’t have to see eye-to-eye to work shoulder-to-shoulder” with people you disagree with. He helps us put our disagreements in perspective and focus on everything we have in common with each other, in spite of our differences.

  • Celeste Headlee, 10 ways to have a better conversation, TED Talk (11:44). In this entertaining and informative video, writer and radio host Celeste Headlee provides ten useful tips for avoiding arguments and having more productive conversations.

  • Katherine Hampsten, How miscommunication happens (and how to avoid it), TED-Ed (4:32). This fun video explains why effective communication can be so challenging. Communication is a transaction between two people who are each interpreting what they say and hear through their own subjective lens. To avoid miscommunication, we can practice active listening (as opposed to passive hearing), use all the signals at our disposal (including signals about our own state of mind), take time to understand, and get to know our own biases.

  • Robb Willer, How to have better political conversations, TED Talk (12:01). Willer explains how we tend to voice our opinions using language that reflects our own values. But we can reach each other more effectively by crafting our message in terms that resonate with the values of the person we’re speaking to.

Essays and Articles
  • How to have a conversation with your angry uncle over the holidays by Karin Tamerius (2018). This article introduces Smart Politics’ “Angry Uncle Bot” – a helpful tool anyone can use to practice honing their conversational skills. This program simulates a text conversation with a relative who disagrees with you about politics. At each juncture in the conversation, the program offers pointers on how to steer the discussion in a productive direction. 
  • How to save Thanksgiving from political arguments by Zaid Jilani (2018). This article explores why it can be especially difficult to navigate ideological disagreements with family members. Jilani helpfully rounds up practical advice from experts on conflict resolution and bridging divides, which we can put to use at the Thanksgiving dinner table and beyond.
  • People will like you more if you start asking follow-up questions by Rachel Layne (2017). Layne summarizes recent research indicating that individuals “who asked follow-up questions were better liked than those who didn’t.” The article explores why people respond so positively to being asked questions, and offers advice on how we can create a habit of asking questions.
  • How to Win Friends and Influence People by Dale Carnegie (1936). This is the timeless classic in how to develop relationships and persuade people to see things your way. It clearly and concisely lays out the fundamentals, such as listening more than speaking and taking care to learn people’s names. Every student should read this for instruction in specific techniques to respectfully engage others with different points of view. For a quick overview, see this one-page summary of principles.
  • Breaking Through Gridlock: The Power of Conversation in a Polarized World by Jason Jay and Gabriel Grant (2017). Authors Jason Jay and Gabriel Grant provide six easy steps to open up pathways during seemingly intractable conversations. Through exercises and examples, the authors demonstrate how we can translate our differences into opportunities for innovation and positive change.
  • Crucial Conversations: Tools for Talking When Stakes Are High by Kerry Patterson, Joseph Grenny, Ron McMillan and Al Switzler (2002). This influential business book provides useful tools for effectively handling high-stakes conversations. It provides specific techniques for achieving positive outcomes from difficult yet important conversations. The lessons in the book can be applied in a range of settings, from in school, at work, at home, or with friends and family.
  • High Conflict: Why We Get Trapped and How We Get Out by Amanda Ripley (2021). New York Times bestselling author and award-winning journalist Amanda Ripley offers “a mind-opening new way to think about conflict that will transform how we move through the world.”
  • Nonviolent Communication: A Language of Life by Marshall B. Rosenberg (2015). This helpful book outlines a four-step process we can use to communicate with people more effectively in all facets of life. According to Dr. Rosenberg, we can learn to handle any difficult conversation with compassion by expressing our observations, feelings, needs, and requests, and listening for this information from others. 
  • The Way Out: How to Overcome Toxic Polarization by Peter T. Coleman (2021). Social psychologist Peter T. Coleman “explores how conflict resolution and complexity science provide guidance for dealing with seemingly intractable political differences.”
Academic Articles
Other Sources
  • Allsides.com provides news stories from different political perspectives to help you “think for yourself.”
  • Better Conversations: A Starter Guide by On Being (2017). This guide, created by Krista Tippett and her team at On Being, combines wisdom and practical tips on how “to create hospitable spaces for taking up the hard questions of our time.”
  • Bridging Divides Playbook, Greater Good Science Center, UC Berkeley. This is a fantastic resource for any one who facilitates conversations between people with different points of view. With all of these skills, you can become a “Bridge Builder” who helps people connect and relate to one another, even across significant divides.
  • Effective communication: barriers and strategies, Centre for Teaching Excellence, University of Waterloo. This document provides an explanation of barriers to and strategies for active listening, accurate perception, and verbal communication.
  • Essential Partners provides training and resources to facilitate difficult, yet important conversations.
  • The Village Square is a non-partisan nonprofit organization devoted to civil and factual discourse across the partisan divide.