Don’t say the word “debate” around Bill Woodson.
He’ll politely clarify that a debate implies two sides disagreeing. At Woodson’s Sarasota-based nonprofit, Conversations Across the Aisle (CATA), there aren’t any winners or losers — just a group of people from varying ends of the political spectrum trying to understand one another.
“People who are curious are not the mainstream,” Woodson said. “If we gave value and valence to getting both sides of an argument, I think it would lead to better policies and better quality of life for everybody.”
Woodson founded CATA about three years ago as a deeply personal response to a question that has come to define modern political life: What happens when people stop listening to one another?
Through a series of facilitated dinners, CATA seeks to “rehumanize” people on all sides of the political spectrum, bringing together those with different political beliefs not to debate or persuade, but to sit at the same table, share a meal and try to understand how a reasonable person could see the world so differently.
The first such dinner took place in October 2023, and the organization has held six more since then — one each quarter, tackling topics like “the evolving relationship between church and state,” “the war on woke” and “what is due process; is it a universal right?”
“I've always been curious about how a well-informed person could come to a different conclusion than I've come to,” he said. “So this notion of [CATA] being about curiosity is very much an extension of my own personality and my own inclinations.”
All this comes at a time when political division feels less like disagreement and more like estrangement. This polarization has led to eroded trust in institutions and fewer shared spaces where people encounter opposing views without feeling attacked or dismissed.
As word spreads about CATA and interest grows beyond Sarasota, Woodson and his team are also confronting questions about scale and sustainability. There’s an apparent demand for the work CATA does, but there’s also a challenge in getting more and more people to let their guard down and want to listen to the other side.
For Sue Jacobson, former CATA planning member and facilitator, that challenge is exactly why CATA workshops are a necessity.
“We're not going to get rid of all the people who think differently than we do, so we need to learn how to live together positively and respectfully, and we need to appreciate each other,” Jacobson said.
Inside CATA’s dinner-based model for civil political conversation
There’s no shouting, no scorekeeping, no winners or losers..
Instead, CATA workshops begin with a shared meal, meant to slow people down before they tackle topics that usually inflame rather than invite conversation.
After dinner, a featured speaker provides a neutral perspective on the topic of discussion. Then, each table, filled with six to eight guests, discusses the topic through guided questions that require nuanced responses rather than simple black-and-white answers.
A question might explore whether the cost of deporting millions of undocumented people should be considered when discussing illegal immigration, or if the human impact should be a factor in immigration policy at all.
Tables are led by a trained facilitator — a neutral presence whose role is to make sure no one dominates the conversation or shuts down someone else. Facilitators don’t argue or offer their own opinions; they guide the conversation, manage time and step in when things veer toward confrontation.
Jacobson, who spent two years as a facilitator, recalled a conversation her table was having about institutional racism. One of the participants stated that “racism was over” and a thing of the past. It’s easy for some to have a knee-jerk reaction to that statement, but Jacobson said she saw something deeper.
“A lot of people at the table disagreed with him, but you could not disagree with his life experience,” Jacobson said. “He'd never really been around many people of different races, and also told me that he wasn't really terribly curious when he was watching the news or reading the paper. What you can say is, ‘My life experience is really different than that.’”
The structure creates room for those respectful and uncomfortable conversations, Woodson said. Getting there took time. Before inviting the public to the first workshop, he and his team spent nine months building and stress-testing the model, working through how to encourage conversation without inviting hostility.
It has proven remarkably effective. So much so that they’re replicating it as CATA looks to expand to other cities, including Venice, Florida, and San Angelo, Texas. The growth is notable, as Woodson expects to go from hosting one workshop a quarter to four or five in that same time period.
Now, it isn’t a question of whether the model works. It’s whether the nonprofit can achieve true success beyond its Sarasota roots — a success that Woodson defines as seeing “CATA Communities” thrive from coast to coast, remaining accessible to anyone who wants to participate.
The personal journey that led to Conversations Across the Aisle
Curious brains don’t take retirement lightly.
That’s what Woodson learned when that time came. He kept thinking: “What can I do that I already haven’t done?”
The answer drew on a lifetime of experiences during his professional career — like assistant dean of community outreach at St. Thomas University; dean of outreach for New College of Florida; vice president for Diversity, Equity and Inclusion (DEI) at Hobart and William Smith Colleges in New York.
But Woodson’s love for outreach wasn’t the only force that led to CATA.
He had also spent time with organizations like Marnita’s Table in Minneapolis and Miracle on the Key in Longboat Key — groups whose missions echoed what he would later build through CATA. They inspired him to form something with the best components of each.
Woodson tossed his idea around to people he knew and trusted. In return, he received multiple offers to help.
Before he knew it, Woodson had a planning team, a three-person board of directors and a grant from Charles and Margery Barancik Foundation to cover the first CATA workshop at the Academy at Glengary.
John Annis, senior advisor at Barancik, is among those who understood the importance of Woodson’s vision early on.
“Despite the divisiveness we might feel all around us, it’s pretty amazing what can happen when people sit at a table together, listen and try to understand one another,” Annis said. “Clearly, we need to have the conversations that Bill and his team are facilitating. … Barancik Foundation supported early efforts by [CATA] to help facilitate that kind of dialogue.”
CATA also got a grant from the Gulf Coast Community Foundation to help with operational and marketing costs and keep the workshop free for people to attend.
While these grants are crucial in helping the 501(c)(3) nonprofit thrive, Woodson said it’s the engagement from the community that sustains it. CATA receives donations big and small from local residents and draws repeat participants who return after being inspired by the conversations.
Tracking whether curiosity carries beyond the dinner table
With its eighth workshop set for Feb. 12, demand for CATA hasn’t waned.
Sessions draw as many as 60 participants. But attendance alone isn’t the point. The real test of success is whether participants carry CATA’s lessons into their daily lives.
To gauge that impact, Woodson said CATA conducts surveys before and after each event, asking about participant satisfaction with the workshop, as well as their willingness to engage across differences.
Examples include: "How often, outside of the workshop, have you intentionally engaged in a conversation on a topic where you knew the other person held an opposing point of view?" and “Has participating in CATA workshops had a positive impact on your comfort and confidence when engaging across ideological or political differences?"
Responses vary, but the trend is clear: Participants report being more open to hearing perspectives different from their own.
That openness is something CATA is looking to strengthen internally. Woodson acknowledged his team leans more progressive than conservative.
“Being actively curious tends to be a liberal trait,” Woodson said, but he tries to be intentional about recruiting people with different political viewpoints to stay true to the mission.
Political affiliation alone, however, is an incomplete measure of perspective, he said. What matters more is a willingness to question the status quo, remain curious about thorny topics and have uncomfortable conversations, regardless of their political party.
Woodson recognized that CATA isn’t for everyone, but he believes it resonates with those in the middle who are often overlooked in society and online.
“I know people who have strong and well-informed opinions, but really just don't have any taste for being surrounded by people who have a different opinion,” Woodson said. “[When] we’re giving all of our rewards, all of our affirmations to the loudest and most extreme voices, we're not giving any nurture, any space for the people who are more in the middle.”
Jacobson, who has a degree in social work, was the chairperson of the New College Foundation Board of Directors during Woodson’s time on campus. That’s how the two met.
While on the 12-person planning team, she said, it was strange yet encouraging to see so many people in the same room who valued open and constructive dialogue. The team, which met once or twice a month, wanted to ensure mutual respect was a central theme of each workshop. That goal, she said, was accomplished.
Expanding beyond Sarasota while staying true to the mission
Working through “taboo” conversations is why CATA is so appealing, said David Wilkins, a retired corporate lawyer who attended two workshops with his wife.
He said he would like to see people more freely speak their minds and dive into topics that might lead to uncomfortable conversations.
“I think the biggest challenge is that you've got to get people on both sides of the aisle who are comfortable, respectfully engaging, but being prepared to speak their mind and defend their positions, even if it gets to be a little uncomfortable,” Wilkins said. “I think that's the genius of the idea, is that people can disagree reasonably, still speak to one another and come back for another dinner.”
Wilkins first learned about CATA through Woodson, whom he met at an event for the Manasota Association for the Study of African American Life and History, where Wilkins is a former chapter president. When Woodson introduced the idea, Wilkins saw it as a “critical starting point” in moving beyond today’s political divisiveness.
“It's obviously a small microcosm of the larger political ecosystem,” he said, “but it's vitally important.”
CATA’s lessons aren’t just for participants; they’re personal for Woodson, too. Whether navigating political disagreements with his brother at Thanksgiving or responding to comments on social media, he said CATA has taught him how to sustain conversations that otherwise might combust.
“It's not just from watching [CATA workshops], it's really from understanding that it’s hard for the other side to even hear what you're saying when you say it this way, but if you say it another way, they can stay in the conversation,” Woodson said. “It's training me to create respectful space.”
This year will be a big test for how much growth CATA can handle as it expands to other cities, and Woodson is ready for it.
Or, as Woodson put it: “Now strap up, we're gonna see if we can pull it off.”
This story was produced by Suncoast Searchlight, a nonprofit newsroom of the Community News Collaborative serving Sarasota, Manatee and DeSoto counties. Learn more at suncoastsearchlight.org.
Suncoast Searchlight says it does not use generative AI in its stories. If you have questions about their policies or content, contact Executive Editor-In-Chief Emily Le Coz at emily@suncoastsearchlight.org
