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This criminal justice reformer’s secrets to tough conversations

Piper Anderson taught theater to middle schoolers before facilitating discussions on mass incarceration. Discomfort, in her view, is crucial to really communicating.

This criminal justice reformer’s secrets to tough conversations
[Photo: motapet/iStock]

Piper Anderson is no stranger to difficult conversations. As an educator and cultural organizer, she’s spent over 17 years facilitating discussions about some of the most hot-button issues facing U.S. society. In 2016, for example, she gave a TED talk about Mass Story Lab, her storytelling series focused on how the U.S. criminal justice system impacts communities of color. “Yes, I’m the person who brings mass incarceration into polite dinner conversation,” she quipped.

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In a time when two black men can be arrested at Starbucks just waiting for a friend, it’s clear that these conversations need to happen. Yet as the coffee giant learned the last time it encouraged people to “race together,” discussions about race, social justice, and other sensitive issues often require thoughtful moderators like Anderson. To that end, here are a few of her top strategies for facilitating the most difficult conversations.


Related: What “facilitation” really means, and why it’s key to the future of work


Need to build trust? Share stories

Trust, obviously, is essential. But it isn’t always easy for moderators to build it in multiple directions at once–both between themselves and the group, and within the group itself. Whenever Anderson kicks off one of her “story labs,” she asks participants to turn to their neighbor to tell a two-minute anecdote about a moment when they became aware of the prison system. “At first they’re like, ‘What, you want me to talk to someone?'” Anderson says. “And then, four minutes, five minutes go by and I can’t get them to stop because they just want to keep talking.”

Anderson believes sharing stories builds trust more effectively than discussing opinions. She finds that people often adopt and harden their beliefs about certain issues over time–typically without critically reevaluating the premises of those beliefs. While it’s easy to get defensive when someone challenges your opinions right off the bat, Anderson points out, it’s much harder to react as strongly when swapping stories. Storytelling fosters empathy, the crucial precursor to trust.


Related: What happens when you ask kids in prison how to fix the justice system?

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Embrace conflict, don’t downplay it

People often avoid tough discussions because they’re afraid of discomfort and the potential for conflict. When I asked Anderson how she handles situations when someone blurts out a controversial idea and brings conversation to a halt, her response surprised me: “I love those moments!” she said. “Those are usually the moments where the conversation really starts and really gets good.”

When you’re leading a discussion about something contentious, whether it’s the criminal justice system or annual budget planning, ask the group to lean into the discomfort. If people can stay in a place of “being curious and being open,” Anderson says–even when they hear something uncomfortable–they’re more likely to take the conversation in a constructive direction. “We need people who appreciate conflict as something that can be generative, that can build and deepen relationships,” she explains. “That is sometimes the right pathway to understanding and solving problems.”

Personally, at least, I often jump too quickly into peacemaking, and I’ve worked with plenty of people who share that instinct. Chances are we could all benefit from working through disagreements thoughtfully without getting combative–a mark of emotional intelligence as well as a skill that takes practice.

Adapt the plan to fit the people

Great facilitators need to have a plan, Anderson believes, but they also need to be ready to throw that plan out the window. In her experience, the true magic happens when the facilitator feels comfortable with ambiguity, rather than worrying that they’ve lost control of the room. “I taught theater to middle schoolers,” Anderson shares, “and what you learn from that experience early on is that you have no control. The more you attempt to control the process, the more resistance you’ll come up against. What you do is just follow the flow.”

To some facilitators, this may sound uneasily similar to winging it, but it’s anything but. If a group clearly isn’t connecting with the agenda she’s set, or failing to respond to a question she’s posed, Anderson will switch things up–moving on to a related idea or introducing a new question altogether. Alternatively, she’ll take a suggestion from the group about where to shift the conversation or even invite someone else to lead it while she hangs back.

This isn’t about ceding control, she says. “When people get a chance to integrate what they’re learning into their own experience–to practice it, to feel like what they bring and who they are is valid–they’re more likely to learn and use the information they gain,” she explains. Ultimately, it doesn’t matter who’s at the front of the room or at the middle of the table; great facilitation–the kind that really leads to great conversations about difficult topics–is all about learning and understanding. And that, Anderson says, always takes active participation, not passive absorption.

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About the author

Jason Shen is the author of The State of Tech Hiring Survey and the cofounder of Headlight, a talent assessment platform. He is completing a residency at TED and previously served as a Presidential Innovation Fellow under the Obama Administration

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