The paradox of persuasion

A few offerings for a season when so many of us are trying to change hearts and minds

Last week, the crew at The Daily, The New York Times’ flagship podcast, issued one of its now semi-regular dispatches from Wisconsin. The topic was the Presidential election, because of course it was. Like all American political obsessives, staffers at The Times are desperate to decipher the mood on the ground here in one of America’s three-to-five purple-est states.

This particular episode focused on a single canvasser, Pete Huff, the chair of the Dunn County Democratic Party. Two Times journalists, Jessica Cheung and Stella Tan, tagged along with Huff as he talked to swing voters in a working class neighborhood in Menomonie. Typical for canvassing shifts, most of the trio’s knocks went unanswered, but they were able to talk to two women— both undecided, one who usually votes for Democrats, the other of whom generally supports Republicans.

My primary emotion, while listening to the episode, was intense vicarious anxiety on Huff’s behalf. Having spent my fair share of time at doors, I can’t imagine what it’s like to have the collective listenership of one of America’s most popular podcasts— many of whom are likely rooting for a Democratic victory— counting on your specific persuasive powers to save American democracy from Donald Trump. And to be clear, Huff is good at his job. He wasn’t too pushy. He asked a lot of questions. After each door, he reflected honestly about what went well and what he might do differently. Most of all, he clearly has a great deal of affection for his community. Any town would be lucky to have him coordinating their field office.

Through no fault of Huff’s, though, the format of this particular podcast episode was always going to put any canvasser, no matter how skilled, under a microscope. After Huff finished each conversation, Tan stayed back with the two voters to ask them a few follow-up questions. And in both cases, the contrast between the two conversations was massive. When both voters talked to Huff, their answers were guarded. No mater the topic, they offered curt replies, deliberately keeping him at arm’s length. They weren’t rude, and neither fully dismissed him, but both conversations were awkward and stilted. There was clearly plenty left unsaid.

By contrast, when Tan hung back for a follow up conversation, both women immediately opened up. They talked at length about their despair at the state of political discourse, struggles that they were seeing in their communities, and fears for their daughters. They also offered the kind of authentic insight into how Harris could win their vote that they didn’t offer when Huff was at the door. Emily, the regular Republican voter, talked about how caring about her kids’ friends had soured her on the GOP’s anti-LGBTQ rhetoric. The Democratic-leaning voter, Kate, pleaded “I don’t care what somebody else is screwing up. How are you going to make it better?” while running her hands through her daughter’s hair and expressing fears about what awaits both of them in a post-Dobbs world.

Now, there are likely a number of variables that may have influenced Emily and Kate’s relative comfort with Tan compared to Huff. Perhaps it’s the former’s skills as a journalist— she is clearly a deeply perceptive, empathetic listener. Or perhaps it was an issue of gender— it’s understandable that the two women might have felt more comfortable opening up to a female reporter than a male political staffer. But from my experience both studying and offering trainings on persuasive organizing, I’d offer one more factor. While both Huff and Tan are good at their jobs, it’s much easier to trust the person (the journalist) whose job is primarily to understand you and your point of view than it is to trust the person with an agenda, the salesman, the person who is clearly trying to influence you.

This is, of course, the core paradox of political persuasion, and one of the primary reasons why many people wrongfully believe that it’s completely impossible. You can’t change hearts and minds unless the people you’re trying to influence actually trust you enough to fully share their stories, including their doubts about their current belief systems. The problem is, we as human beings are less likely to offer trust and vulnerability with somebody whom we know is trying to change our mind. Think of the times you’ve found yourself in an argument with a person on another side of a political divide. More likely than not, they’ve either blown up (showcasing the sheer force of their recalcitrance) or clammed up (like the curt responses that Huff got from Kate and Emily).

This is not an article about “one cool trick” that can immediately transform you into the best persuasive organizer in the world. Nor is it just a clunky plug for the trainings I’m running this fall (I’ll share some more about those in the end notes, but this essay isn’t sponsored content for myself— if I’m a helpful resource to you, either as a writer or trainer, terrific; if not, that’s ok as well).

I will say, though, that this question, namely how you build trust when the other party knows that you’re trying to convince them, has been the single most animating professional quest of my life. I’ve spent years reading every piece of literature I could find on persuasion, hounding respected organizers on what they’ve discovered, studying the ins and outs of the most effective persuasive techniques (like deep canvassing). And you know what I discovered? We’re a tricky species, us humans. There’s no single technique that works 100% of the time, and definitely nothing that works with any messenger and any audience (have you ever discovered that you’ve been more patient and curious in “conversations across the divide” with strangers than your family members? there’s a reason for that!).

There are, however, a few principles I’ve discovered that often make a profound difference in the quality of conversations I have with people whose viewpoints I’m hoping to influence. And because I know that we are in a season of persuasion— where some of you will be knocking on doors for your preferred national candidates (likely Harris-Walz for the majority of my audience), others will be trying to build coalitions for Gaza and still others will be working on vital local issues, I wanted to at least tease a couple of them.

Before I share these principles, though, a caveat, especially for the canvassers and phone bankers among you. It’s highly likely that many of the campaigns you’re volunteering for this season would prefer you to stick to the scripts they’ve developed rather then try something new. There are only 80 days or so until the election, and they don’t want you experimenting with more longitudinal approaches. At this point, they’re likely to be concentrating volunteers on “safe” doors, primarily doing get out the vote work. That’s fine. Perhaps now is not the time. But if you have a hunch any of these thoughts will be useful, keep them in your back pocket.

Don’t pretend that you’re agnostic

Wait a second? Didn’t we just determine that the whole reason why Tan was more able to get her interviewees to open up than Huff was that, in this particular setting, she was a relatively agnostic reporter with no immediate agenda and Huff wasn’t? Sure, but you don’t build trust by pretending to be something you aren’t. So unless you do happen to be a reporter at a major national outlet who, in this case, isn’t trying to persuade (hi to the handful of you who I know read this newsletter!), you don’t get to say “hey, I’m ______ from The New York Times and I just want to ask you a few questions to understand your perspective.”

That’s why, In my experience at least, it’s vitally important to make sure that the other person knows that you have a clear opinion. If you’re a die hard Harris-Walz supporter, you need to say “I’m strongly for Harris-Walz and I’d be lying if I wasn’t hoping that you’d make that choice too.” If the name of the game is trust, we can’t start with lies, either of omission or commission.

But (and this is equally important), you don’t stop there…

If you want the other person to eventually be open to your viewpoint, you must be willing to not try to persuade them, especially in the first conversation…

Damnit! I’m offering counterintuitive (and perhaps even contradictory) advice. I know! Stay with me.

Remember the way I introduced myself up above? Well, that’s only the first half of it. After sharing that I have a strong point of view on whatever topic we’re discussing, I add “… and while I’d love to have you eventually agree with me, that’s truly not what I want to do in this conversation. I’m wondering if instead I could ask you some questions, because regardless of what I believe, I really am curious about how other folks are experiencing this moment?”

I hesitate to write all that out, in a way that sounds like a script, because what matters most here isn’t the specific words I say. It’s about whether or not I actually believe them, if I can give up the hopes of converting the other person (definitely in the short-term, but perhaps at any point) because I actually feel that there’s something to be gained for understanding more deeply the way others are metabolizing the world we share. And that’s hard! I have to gut check myself on whether I’m truly in that space before every single political conversation I enter into. And to be honest, there will always be some people that each of us can’t offer that level of grace (for folks I've trained, sometimes that’s because of power dynamics and intersectionality, interpersonal baggage, or specific topics that hit too close to home for them). And that’s ok. Your uncle who you can’t discuss politics with might be exactly the kind of guy with whom I can offer some authentic curiosity. Meanwhile, the mom in my PTA who makes me feel insecure as a parent might be a tough lift for me (I’ve got to work through my stuff with her first), but you might be an incredible conversation partner for her.

Ask questions that you’re actually curious about, rather than questions that will just result with the other person rattling off their stump speech

Again, a quick reminder: Everything I’m currently offering here is a wildly overly-simplified, newsletter-length teaser. There are skilled organizers from so many disciplines (the labor world, the community organizing world, etc.) who would love to offer you more comprehensive trainings on what it looks like to really build transformative relationships with other people. What I’ll say right now, though, is that the difference between the most successful and least successful conversations I’ve ever had (on any topic, but definitely where organizing is concern) always hinges on how authentically curious I am, and the extent to which my questions reflect that curiosity.

Put more directly, when I ask boring questions, I get boring answers. Ones that don’t betray any vulnerability. Ones that falsely present the other person’s life as being free of doubt, insecurity, or cognitive dissonance. Ones where both of us pretend to be purely rational political actor who have crunched the numbers and landed on our diametrically opposed opinions.

For me, curiosity is a renewable resource. The more conversations I have that are actually vulnerable, interesting, and which give me insights into how people— both those with similar backgrounds from me and those with very different identity markers— are navigating our shared world, the more energy I have for more of those conversations. And you know how I get interesting answers? By asking interesting questions, ones that the other person is more likely to answer honestly and reflectively. That’s why the first two steps are important— I need to actually care more about the quality of our conversation than whether I convince them.

What specific questions do I ask? It depends on the person! And I don’t think you actually need me to tell you how to ask an interesting question. Whenever we brainstorm questions in my trainings, I’m just delighted with how the energy and idea flow naturally from people, regardless of their organizing experience.

But with that said, sharing questions are fun, so here are a few I love:

So, I already told you that I’m on ________ side of this issue. What pisses you most off about people like me?

So, you told me that you believe _______ politically. What were two big moments in your life that influenced that belief?

What’s one thing that government either is or isn’t doing right now that, if it were to change tomorrow, would have the largest positive influence in your day-to-day life?

What are you most afraid of your government doing— either to you or somebody you care about? Where does that fear come from?

When you think of somebody in your community who is actually making life better for others, what are they doing?

When you hear me say “I wish that you’d take my stance on _____ issue” what feels most risky and scary about doing so? What would you have to give up? What would you risk? What about your perspective are you worried I might not understand?

Are there any moments, on this particular issue, when you doubt the position you’ve taken? Why or why not?

We’ll stop there for now. But I hope you get the point. None of these are leading questions. I have no idea which direction the conversation will turn after I ask them. Sometimes, the two of us discover some surprising common ground. Other times, they reveal the length of the gap between us. Quite often, (even with strangers I meet at the door) myself and the other person leave the conversation with enough mutual energy and affection that we agree to keep talking, to continue puzzling through it together. Some of those conversations, in turn, have resulted in changed hearts and minds (both from the other person and from me). Other times, I’ve eventually said “this isn’t happening now, but I hope both of us have felt good about the interaction.” In virtually every case, I leave the interaction invested in the other person— perhaps I’m rooting for a material change that will make them life better, or maybe that they might find a peace they’re currently ranking. More often than not, they’re rooting for something for me as well.

Yes, there’s an art to how to eventually transition to asking the other person to take a step out of their comfort zone. Yes, there’s an art to when and how I share my own story. But none of it is manipulative. In every case, I’m staying true to my principles— of course I have a point of view, but I’m always focused on the person in front me more than my brilliant arsenal of arguments.

Through all of this, you have to believe in the potential of the other person

I couldn’t end this essay without a reference to Jane McAlevey, the legendary union organizer who passed away this year after a long fight with cancer. McAlavey was the most effective organizer of my lifetime. She was the driving force behind the labor movement current mini-renaissance, and inspired thousands of organizers, myself included, whom she never met. If you’re not familiar with her work, you’re in for a treat. There are so many lessons to be learned from McAlavey’s career as both a practitioner and a scholar of organizing, but when I’m lost, there’s a single quote that I come back to with a frequency that borders on devotional.

“I’m looking for people who… genuinely respect ordinary people…[because] people will see though somebody who doesn’t really believe in them in about five seconds… I start out every day genuinely believing that people can make radical changes in how they think about and see the world.”

Again, I’m not saying that every single person reading this has to single-handedly organize every other person in the world. I’m a straight cis White guy. It’s easy for me to preach a deep belief in the liberatory potential of a stranger at the door, in a church pew, on a neighboring barstool, or even at your family’s Thanksgiving dinner. So few of those spaces offer me any acute threat to my personhood. Dynamics of power and safety are real.

What I am saying, though, is the moment that you do make the decision to try to organize another person— either a stranger or somebody you know— that decision is an act of hope and faith. You are saying, in essence, that you believe in a version of that person whom you may not have encountered yet More so, you are saying that you believe in a version of your relationship that hasn’t been built yet. One that’s trusting. One that’s vulnerable. One that calls both of you to the most caring, most big-hearted, most community-minded version of ourselves.

End notes:

1. Yes, I do offer trainings on all this (through my organization, the Barnraisers Project). Sometimes I offer more comprehensive ten week trainings. Other times I offer a whole lot of smaller mini-classes. This fall, I’ll be offering the latter. I haven’t announced dates yet (soon!) but you can sign up here to join the interest list for the next sessions and read more about them here (they’re free, by the way, though donations are solicited at the end).

2. But for real— I’m not just plugging myself here. There are a lot of great organizing trainings out there. A couple sources I trust: The good people at People’s Action have upcoming info sessions about deep canvassing. Also, while she was alive, Jane McAlavey was an incredibly generous trainer, and she archived many of those trainings on her website.

3. Speaking of getting insights from rural Wisconsin, I’m on the road today to canvass with Sarah Keyeski, a Wisconsin State Senate candidate from Lodi (you might remember that I wrote about her a few months ago). I’m likely going to be writing about Sarah’s campaign (as well as another candidate, Emily Tseffos, who lives in the Appleton area and is running for the Wisconsin State Assembly) so stay tuned! I’m excited to further introduce you all to candidates whose campaigns are deeply grounded in the places they’re running and the people whom they’re hoping to represent.

4. Why can I offer organizing trainings for free? And also offer newsletters like this? Because of the support of generous readers and donors. With that said, it’s still a precarious balance, keeping all of these balls in the air. How does it become more sustainable? If more folks who find value in my work and who have a few bucks to spare chip in to help out. Currently, there are nearly 11,000 folks who read this newsletter, but only a few hundred are paid subscribers. Would you be willing to join them? That link below will work. Alternately, you can support by buying a book (it’s good! and outlines a lot of the junk I had to get over to be able to organize in this way!) or donating directly to the Barnraisers Project. Thank you, sincerely.

5. No song of the week this week, as I need to catch up on updating the playlist (it’s been a while!). Updated or not, that playlist is available on both Apple Music and Spotify. Also, as I keep milking this brief moment where the nation’s attention is focused on dads in the Upper Midwest, I keep threatening to make a Walz-Core playlist. You’ve been forewarned, I suppose.