Every Leader Needs a Listening Tour

Annie Rappeport, who brings 15 years of dialogue design and facilitation experience at various universities, explores the professional friction between immediate productivity and deep, collaborative engagement. She has frequently navigated a specific disagreement: critics argue that a new leader should focus on rapid execution and desk-based visibility, while Rappeport insists that the initial priority must be meeting and listening to every team member. She maintains that relying only on past experiences or theoretical research rather than the lived experiences of a new environment risks leading a group astray. By prioritizing connective conversations and collaborative imagination, she advocates for a leadership model rooted in building resiliency and bridging practices rather than just speed.

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Transcript

Michael Lee : [00:00:00] When We Disagree is a show about arguments, how we have them, why we have them, and their impact on our relationships and ourselves. You'll likely forget the to-do list you wrote this morning, but you'll remember the purple elephant wearing an orange tutu that I just made you imagine. You're welcome. Our brains are wired to privilege bizarre, unusual, and distinctive information over common, everyday practical data.

This is the bizarreness effect, a survival mechanism where our ancestors evolved to notice anomalies, strange events that might represent a hidden danger or a sudden advantage. In modern life, this bias shapes what we remember, what we believe, and how we argue. News media and social media algorithms exploit this ruthlessly.

Man bites dog always beats dog bites man in the attention economy, which means our sense of reality is often constructed on memorable extremes rather than statistically salient truths. [00:01:00] If it bleeds, it leads, as the journalistic saying goes, and algorithms learn to surface the most absurd content because they know outrage and absurdity stick in the mind, while nuance and normalcy are simply scrolled past.

In our personal lives, the bizarreness effect can be devastating to a relationship. We tend to remember that one strange out-of-character fight from three years ago, while forgetting hundreds of days of consistent, quiet support. We can define our partners and our coworkers by their most unusual moments rather than their long-term habits and patterns.

Breaking this bias requires conscious appreciation for normalcy. When a disagreement feels like it defines the entirety of your relationship, ask yourself whether you're fixated on a bizarre outlier or a genuine trend. That one weird thing they said might just be a trick of your memory's natural bias towards the strange.

I'm Michael Lee, Professor of Communication and Director of the Civility Initiative at the College of Charleston. Our guest today on When We [00:02:00] Disagree is Annie Rappaport. With 15 years of dialogue design and facilitation experience at various universities around the nation, Annie Rappaport is interested in building community resilience through connective conversations, collaborative imagination, and peace-building practice.

Annie, tell us an argument story. 

Annie Rappeport : Hello, Michael. Thank you for having me. Yes, I have an argument story, and it's an argument that's followed me throughout my life. So it hasn't happened just once, it's happened almost every time I've started a new project, whether it's at a university or in another setting.

And when I'm asked to start a project I always say I want to meet and listen to every single person I'll be working with, and almost always, not always, but almost always somebody disagrees with me and says, "That's not a useful use of your time. That will drain you. That is not a wise choice, Annie. We picked you to be a leader to get things done quickly."

"And that's too time-consuming and [00:03:00] too distracting. And what we really need you to do- ... is to be in your office at your desk and be visual in that way." And I just firmly disagree with that and feel that the need to listen and to also get out of the office in order to do that and meet people where they are.

So that's a co- that is a disagreement I've had so many times. 

Michael Lee : So just to take your side on this, and then we'll do devil's advocate and take the other side for just a second. You come into a new project, new situation, new job, whatever it is, and you say, "I wanna learn as much as possible from other people's points of view.

I wanna take as many meetings with people, ask them a bunch of questions, and learn so that then I can figure out what I wanna do." 

Annie Rappeport : Yes. Yes, what I wanna do- ... and more importantly, a lot of times when I'm leading, it's what the we wanna do.

Because if I come in and I'm new at a place, and I assume based on my last experience or based on only what I've read and not the lived experience, then I can really lead a group astray.

And so I take that leadership element really seriously. I'm there to lead a we, and it's not just about my vision [00:04:00] it's the whole community if I want it to work the way I think it, it works well. 

Michael Lee : Yeah. And then are there n- known unknowns as you approach these meetings? In other words, you need information about X, Y, and Z that you don't currently have.

And then are there also unknown unknowns, stuff you just have no earthly idea that you should know stuff about when you're having these 

Annie Rappeport : meetings or have- Oh, my goodness. I love that term. I'm gonna adopt it, Michael. Unknown unknowns. It m- it, it's just filled with unknown unknowns. 

Michael Lee : Yeah. Yeah. I j- I just know it from the great documentary about Don Rumsfeld that Errol Morris did, so that's where I stole it from, just to give fair credit.

Annie Rappeport : Oh. Oh, yes. And usually it's the stuff that really matters at the core that isn't the stuff that's gone through a filter that makes it into the handbook or makes it onto the website or makes it into the- ... the pretty polished thing that we create, which is needed and wanted and great, but a lot of those unknown unknowns are so key to things that I view as so important, like morale mission alignment, ... and [00:05:00] just people looking forward to contributing and feeling valued and feeling seen and heard. And it really, I've seen it transform places I've been over and over again, so I'm just gonna keep doing it. Though each time I've, I really welcome the challenges that are brought to me about that time consumption.

For example I was asked to scale up my work rather quickly at Virginia when I was helping lead a dialogue program. We were expecting 30 students. We ended up with- A couple shy of 300, and I was like, "I'm gonna meet with every single student and listen to them." And my colleagues they weren't disagreeing with me from a, from those, the instances I had in the past from other organizations I worked at.

They just... That was caring for me. They said, "How on earth are you going to do that?" That's a lot of meetings. And so there's... And they had a really good point. At some point, if I wish to scale up my work, I need to rethink how I accomplish that without leaving anyone out, but also realizing I am human and getting to know that many [00:06:00] people rather quickly- Yeah

I was not I'm ha- I'm not happy to say, but I should say they were right. Even with me being stubborn, I met with about a third of the hu- 300 students. I met with about 100 of them one-on-one. 

Michael Lee : And there is a kind of with any big project, and I know this from researching and writing and advising lots of research projects, that there's a point where you can just research this thing to death, and it actually leads to a place of paralysis, where you're spinning your wheels but you're not actually producing.

And so now we're transitioning into the downsides of- Yeah ... being a little bit too research-focused and a little less leadership-focused. So let's take the sharp edge of the spear here. What are the best arguments against your approach that you've heard? 

Annie Rappeport : The best arguments that I've heard and experienced- Yeah

so I've really liked them, right? I've liked the arguments 'cause I'm like, "Oh, that's what that person said. That's what's happening right now," and I'm, I have this awareness that I might not have [00:07:00] otherwise. And one of the ones that comes to mind is at Maryland, I was elected into a position where I was representing at first 10,500 students, and then the year after I was elected to represent 172,000 students across the state of Maryland.

Michael Lee : Okay. 

Annie Rappeport : And so those are that big scale-up, right? So I didn't even go in with the illusion that I was gonna listen to every single student in those things, but I was brought in for specific fights, in-fighting that were happening, and people wanted me to step in and help. And for those groups I wanted to listen to everyone.

But what I noticed happening, to other people's credit of what they told me to warn about, is when people are in mid-conflict, depending on who you listen to first, that, even that step is seen as taking a side, and people are trying to more so persuade you to a side than help you learn the holistic approach if there's a fight currently or a conflict currently going on with their, when there's a lot of emotion or high [00:08:00] stakes.

And so when I was having those meetings, instead of it being a genuine, we're all on the same page, we want everything to go forward. It was like, "Hey there, new person. Let me give you the real scoop. This person's a problem- ... this thing's a problem, that thing's a problem." And it turned into of listening to a lot of frustration and blame- Yeah

which can be detrimental, right? 'Cause I'm hearing them before I hear the next person. Yeah. 

Michael Lee : And that's an issue of your ability to stay objective and- Yeah ... listen with some curiosity, but also with some critical thinking this is just one point of view and I shouldn't have my whole judgment of somebody I've never met before colored by the comments of this person who I'm just meeting for the first time, and so forth.

You said something earlier, too, that I was getting as another critique of your approach, which was, "We hired you to lead. We didn't hire you to listen." 

Annie Rappeport : Yes. Isn't that fascinating? I would... 'Cause for me they are one, it necessitates [00:09:00] the other. They're, they both buoy each other up. But yes, sometimes I was brought in or I was seen by usually those in a context with more decision-making power- as, "We wanted you. You're easy to get along with. What are you going out there and doing?" "That you're bringing these perspectives that we were hoping you would filter out for us," right? And I think filtering out the, what I view as very constructive criticism, doesn't actually help the organization or the group as much as maybe they're hoping if they don't look or see or hear that negativity.

Michael Lee : Yeah. 

Annie Rappeport : It can lead to a worse place down the line, even if I'm a fairly easy to work with person in the here and now. And I want to be that person that says, "Hey, we need to pay attention. People are hurting, or people want to be heard." And so I view that as... I still keep my argument up for that one, but yes, it has been said to me. Because they were hoping- Yeah ... that I would just come in and bring my personality which is known [00:10:00] very much as peaceful and so they think that means not conflict, that I would fully disagree. It's... Conflict is needed and it's a matter of how we handle that conflict, not avoiding it entirely.

That's just detrimental. 

Michael Lee : It sounds like there's a larger, and maybe unspoken dispute happening about competing theories of leadership- 

... 

Michael Lee : That really undergirds this argument about how you should spend your time at the beginning of a new project, with you thinking that leadership begins and is thoroughly braided into and within listening, collaboration, cooperation, et cetera.

And then another view of leadership that sees it perhaps as more domineering- visionary or is at least worried about a leader being overly deferent. 

Annie Rappeport : Yeah. Truth. I think that's absolutely true. 

Michael Lee : Yeah. 

Annie Rappeport : And I'm so grateful for that tension- 

... 

Annie Rappeport : [00:11:00] Because it's made me be a better leader, to take who I am at my core and how I do the approach, but keeping in mind those criticisms because they do have some m- they have merit.

Michael Lee : Yeah. 

Annie Rappeport : And it helps balance my personality and my approach to leadership. And then on the flip side, I hope that when people encounter and interact with me, and I disagree with them on this, I hope I'm helping to balance them out, too. 

Michael Lee : Do you find the aspects of your role in your leadership roles, do you find either of these to be difficult constitutionally?

And from your experience and with your personality, which you describe as peaceful, one a leaderly approach that requires a big-picture vision and then moving with some speed and with some devotion to that vision, consequences be damned or two, inevitable conflict, whether that's big-picture vision stuff or small-scale "Hey, we need to course-correct on your behavior," or, "We need [00:12:00] to see eye to eye on this better," which involves some conflict.

Annie Rappeport : Definitely. Definitely. Yes, I think one of the most difficult pieces is finding that balance to still be effective or to maximize how effective we are being. 

Michael Lee : Yeah. 

Annie Rappeport : Usually, I'm leading with a group. I'm one person one leader meeting in a room with other leaders, and we all have different roles in that leadership.

And I would say one really powerful example of what we lived through... I actually, I was reminded by this listening to one of your prior, one of your episodes. Okay. And it was somebody talking about trying to make business decisions for their employees during COVID about vaccinations. And see, I was also in a leadership role related to university response across the state of Maryland, research labs, student health, faculty wellbeing related to COVID. 

Michael Lee : Yep. 

Annie Rappeport : Finding that balance was so important in that case. There were really time-sensitive decisions that needed to be made, [00:13:00] and there were people with really big feelings and thoughts that mattered, too.

And so we could work together to find that middle ground, 'cause I would be somebody who said, "We need to have more town halls. We need to hear why people are reticent, why they're not trusting this. Why is there an erosion of trust? We need to get to at the heart of the matter." And others were like, "You know what?

We need to get... We need to practically figure out, are we keeping these research labs open?" Are we not? Yeah. Are we gonna let people work from home? Are we not? Are we going to have flexible grading? Are we not? And those things had very specific timelines that push up against a desire to really listen through a conflict and bring it that holistic way through.

And those forces are real and I'm so appreciative for people who are different than me, because we can kinda come together and I think come to maybe not the best result, but we can do the best with what we have. And people know that, 'cause we're fairly transparent. 

And so I think we, through that process, people can see the humanity in their leaders, which then [00:14:00] helps whatever decisions happen not feel inhumane or without care.

Michael Lee : Yeah. In these experiences, have you come up with a kind of a theory of effective leadership? In other words, if Rutledge or some big press came to you and said, "Hey, look at these big experiences you've had. You could find an audience if you wrote Annie's Guide to Leadership 101." Or have you come up with a series of ex- of practices that work for you that you wouldn't necessarily be willing to generalize about in terms of effective leadership across the board?

Annie Rappeport : That's a great question, 'cause sometimes people ask me for advice- Yeah ... and I always come back with, before giving advice, I have a whole series of questions. That 

Michael Lee : sounds 

Annie Rappeport : like 

Michael Lee : you.

Annie Rappeport : That sounds very on brand for you. For example, I was with somebody who's, he's a professor in a philosophy, and he was coming to me.

And this is, has to do with leading... Leadership is facilitation, right? Facilitating others to come and [00:15:00] lead their group together, and that can happen in a classroom too. And this philosophy professor was coming to me 'cause they were just, they wanted to figure out how to get their students to engage, and they have these classes, and only four or five people out of 20, 40 students engage across the entire semester.

And they said, "Give me advice. You seem to always get folks engaged." And so before I could give advice on how to help facilitate that or lead that as a professor better, this exploration of a very difficult topic, this person does metaphysics, I had all these questions for him. Why do you think that is?

Are you incentivizing answers over questions? Do people, are people really concerned about having the right answer and it's a difficult topic? Are there ways to help the introverts in the room know those questions before they get in the, in there so they can process before they're in the room? So it becomes an exchange rather than a here's the 10-step guide, and no matter who you are or where you are, this 10-step guide is gonna lead you to leadership success.

That would feel really inauthentic for me. Though I enjoy books that I read like that. 

Michael Lee : [00:16:00] Yeah. You have come up with, maybe it's not intended as such, but a pretty catch-all definition of leadership, of effective leadership for you. You say- Leadership is facilitation. And as you were talking, I was trying to come up with what the counter interpretation of leadership would be that would, from that perspective, have some suspicion about you going around and listening to all these people.

And I think if we were to give it a n- give it a bumper sticker, this alternative interpretation of leadership would be leadership is expertise in action. 

Annie Rappeport : Ooh. And 

Michael Lee : so- Okay ... what about leadership as expertise in action strikes you as something that you wouldn't be comfortable enacting? 

Annie Rappeport : Okay.

Leadership is expertise in action. The only thing that would strike me as uncomfortable, I actually like that concept as I'm visualizing 

Michael Lee : it-

Annie Rappeport : okay ... would be, for me, [00:17:00] it would just be pluralistic. It would just be expertises, and it would be a group again, and how do we figure out what our strengths are and bring the group together as a whole.

But I like- ... that idea, and I like that idea of recognizing that in individuals and what we give. 

Michael Lee : Yeah. 

Annie Rappeport : And I, and that engagement to action being an interaction because I feel so strongly. One of the things that's, that has really, the... You have certain things that are set or traditional or conventional, and one of those throughout my time at work has been viewing presence as at a desk, and if you're not at a desk, you're not working.

You're not actually- ... working unless you're at that desk with that computer or you're in that- ... and I've always challenged that. I continue to push up against it because I think that exact philosophy, at least in the role of higher ed, is what leads to divisions between town and gown or leads to divisions between administration and professors or professors and students, is this idea that, of where we can be a leader or where we can [00:18:00] show that we're getting our work done.

If it's limited to these physical spaces that are quite tethering, I think we're gonna miss so much, and I know I've felt the pressure. I've felt the pressure to be at my desk or I might lose my job. "Where's Annie all day?" Oh, and they'll be- ... and then I can show where I've been, but it's almost like a defensiveness that I don't appreciate because I can see that the work is done better together when you go and meet the people where they are.

And yes, that means sometimes they come to my office, but it also means I go to them in their spaces. 

Michael Lee : Final question is a big one. L- Let's talk about leadership. The subject of leadership is everywhere, and it's a billion-dollar book industry probably all on its own. And how many courses and short courses and workshops and retreats, and you name it, are focused on leadership.

How many scholarship programs and municipal programs are focused on cultivating leadership? [00:19:00] Is it possible that we as a culture are talking too much about leadership to the exclusion of other topics we should be focusing on? 

Annie Rappeport : Yes. 

Michael Lee : In other words can we all be leaders? Or is it literally possible for every one of us to be a leader at the same time?

Annie Rappeport : I do think we talk about it too much. I think it goes into that buzzword area. 

Can everyone be a leader? That's a really hard question. I think certain circumstances do call upon people to be leaders, but I truly have met people who the idea of leadership does not interest them, so unless they were forced to be one, I don't think it would come easily or be accepted.

Yeah. So I think part of it is a showing up and wanting to do the work, 'cause this work that I do, that I find so... It fills my cup and energizes me. For others, even when I've interviewed they'll... I get questions about, "How do you listen to people all the... That is just so draining. Like, how do you take care of yourself?"

And I s- And for me, truly, honestly, it fills me. [00:20:00] So for me, sitting around, and I gave an example, I said, for some people, they love organizing stuff on spreadsheets. I've had jobs where I have to do that, and I am ready. I am so drained. So I think we all have different things that kind of call to us, and for me, it's this connection with humans, fellow humans, and I really wish, as much as people talk about leadership, I feel like we're taught so much about how to analyze, how to answer, how to do public speaking.

And I feel like there's a really undervalued piece of thinking that listening is not passive and something you really need to practice and learn about. As well as crafting questions. We're taught so much to care about the answer that I wish we cared more about and incentivized the questions.

Michael Lee : Yeah. Listening, and this is that other perspective, right? Li- listening or leadership as expertise in action means action as opposed to listening, and expertise as having knowledge as opposed to asking questions to acquire knowledge and the kind of deference that implies. And [00:21:00] you tweaked my alternative definition to make it more of a group, right?

Yeah. 

Annie Rappeport : All 

Michael Lee : of us as experts, perhaps situational and contextual, and then you also pluralized it to talk about expertises as opposed to just the singular person, the sage on the stage, who is the expert that you all listen to. And perhaps we can do the same thing to pluralize this notion of leadership, which is to talk about leaderships instead.

Annie Rappeport : Yeah. I like that. I like that. 'Cause yeah, I want my leaders... You don't want me running a hospital. You do not want me running a hospital. The timeframes needed, the decision-making that needs to happen, you don't want... I don't, I- ... I know that's not a good fit. But when it comes to things like community building elected positions- Yeah

doing this dialogue work, I'm a great, I'm a great fit. So I do think, I like what you're saying, like leaderships.

Michael Lee : And you may not have the expertise in medicine at all. 

Annie Rappeport : Oh, not at all. [00:22:00] And it's so great for other people do. 

Michael Lee : That's right. Annie Rappaport, thank you so much for being on When We Disagree.

Annie Rappeport : Thank you, Michael. 

Michael Lee : When We Disagree is recorded at the College of Charleston with creator and host Michael Lee. Recording and sound engineering by Jesse Kunz and Lance Laidlaw. Reach out to us at whenwedisagree@gmail.com.