18: Ethical Leadership in Business and Life with Willys DeVoll

Willys DeVoll is a professional writer and co-author of the book, Leadership is a Relationship: How to Put People First in the Digital World, with Michael S. Erwin. Willys is the founder of Will Digital, a writing and design agency. As an expert at the intersection of language and technology, he’s spoken at a wide range of industry conferences and on podcasts. Willys earned master’s and bachelor’s degrees from Stanford University, where he studied English and philosophy.

Willys helps us to think about the following questions: What traits make for an effective leader today? How can we build authentic relationships in our increasingly technology mediated world? Is it necessary to squeeze every ounce of productivity out of ourselves? 

Episode Transcript

Seth Villegas 0:04
Welcome to the DigEthix podcast. My name is Seth Villegas. I’m a PhD candidate at Boston University working on the philosophical ethics of emerging and experimental technologies. Here on the podcast, we talk to scholars and industry experts about pressing issues in data, business, technology, and society from an ethical perspective. In this episode, I have the pleasure of speaking with Willys DeVoll. Willys is a professional writer and co-author Leadership is a Relationship: How to Put People First in the Digital World with Michael S. Irwin. In addition to book projects, Willys is the founder of Will Digital, a writing and design agency. As an expert at the intersection of language and technology, he’s spoken at a wide range of industry conferences and on podcasts. He also co-hosts and produces An Inconvenient Blueth, a podcast about the New York Giants. He earned a master’s and a bachelor’s degree from Stanford University, where he studied English and Philosophy. Willys and I met when we were both undergraduates at Stanford. Our interviews informed by this mutual experience we have had with the peculiar culture of Silicon Valley. Since I have been in school for the past eight years after graduating, there were some times I thought about what it may have been like to go work at a tech company. Talking to Wyllis was a big reminder of why I got into studying the things I’m studying now, related to the ethics of technology. For those who have already read Willys’s new book, Leadership is a Relationship, that angle on our conversation may be surprising, unless you yourself have encountered some of these things, specifically in Silicon Valley. And as I mentioned to Willys, I believe that this book is really aimed at addressing the challenges of our new work culture, including the transition to a largely remote environment. Before getting to the interview itself, I want to highlight a few things in the form of our key questions. First, is it necessary to squeeze every ounce of productivity out of ourselves? Second, how can we build authentic relationships in an increasingly technologically mediated world? As a final thought, I was reminded of the quantitative self movement, which is dedicated to measuring and optimizing every part of one’s life. For instance, it is about tracking one’s heart rate and calories everyday for the sake of peak performance. While that isn’t necessarily a bad goal, it can be exhausting to live that way. Even more, so it can be exhausting to have that kind of performance expected all the time. Paradoxically, the short term gains in this area can lead to long term dysfunction. I know I personally wrestle with this, and that’s partly why I was interested in talking to Willys in the first place, because I’m hopeful that we can find a cultural and relational solution to some of these problems. And of course, I would love to hear from you about whether you agree with Williy and Michael’s old-school solution to leadership. This podcast would not have been possible without the help of the DigEthix team Nicole Smith and Louie Salinas. This episode was cut and edited by Julia Brukx. The concept art for this episode was designed by Julia Donahue. The intro and outro track Dreams was composed by Benjamin Tissot through bensound.com. You can find more information about us on our website, DigEthix.org, and on Facebook and Twitter at DigEthix and on Instagram at DigEthixFuture. You can also email us at digethix@mindandculture.org. Links to Willis’s book and information about him can be found in the description for this episode. Now I’m pleased to present you with my discussion with Willys DeVoll.

Thank you so much for joining me Willys. I was really excited to see that you had written a book. So I was wondering if you could first just tell us a little bit about what the book is, and a little short synopsis of it.


Willys DeVoll 3:33
Yeah, absolutely. And thanks for having me, Seth, this is a pleasure for sure. So Mike Irwin,and I co-wrote a book. It’s called Leadership is a Relationship: How to Put People First in the Digital World. And really, it’s a book of stories. So we interviewed roughly 20 people. And the common denominator among all of them was they’ve thought very consciously about how they’re a leader and consciously about how forging really substantial, meaningful relationships with other people on a personal level is part of that leadership and integral to that leadership. So other than that, there’s quite a bit of diversity in what their leadership looks like. Some of them have very conventional leadership backgrounds, either CEOs, or very high in the military structure, or things like that. Some of them are much less traditional, but leadership nonetheless. So leading within their family, leading informally in organizations, often leading without much or any codified status or authority. But yeah, the idea was, what does it look like to really prioritize people and their well being? And how does that not only lead you to kind of behave yourself in an ethical manner, but how does that also produce results? And so the ladder we wanted to be really careful about, because we don’t want this to be a cynical, hey, if you do this, you’re going to look really cool. And people are going to think you’re a really great person, but it’s really for the bottom line, it’s not so much that the results are in and of themselves, but that you can kind of do the right thing. And those will often lead to the kind of results you’re going to need to deliver anyway. And so that was the idea. And then we go like that from all of these people we interviewed but then also several themes that we kind of saw coalescing over the course of these interviews.


Seth Villegas 4:55
Okay, perfect. I would say going through the book, it definitely seemed geared towards businesses, and maybe business people. I mean, not exclusively, of course. But there seemed to be a sense of really valuing the kinds of help that you have, and really taking opportunities to deepen those relationships for the sake of a better whole. Am I kind of getting that right?


Willys DeVoll 5:14
Yeah, absolutely. And I think at some level, we’re thinking of that as a corrective for the defaults that we’ve heard people talking about. And you know, that Mike and I have experienced firsthand where, and I don’t want to get too deep into the weeds and the kind of structural issues, because I’m certainly not an economist. But there’s definitely a sense, especially in businesses, and I think this is probably why it comes through for you that there’s kind of a business emphasis in the book, that unless you’re proactively deciding to prioritize people and make them meaningful in how you think about and value things, that there going to be all these structural incentives that push you in other directions, and those other directions are often going to be counterproductive to people’s well being and to the well being of your relationships with them. So yeah, I think it kind of starts with properly valuing properly, properly, acknowledging the people that you might not be forced to value and acknowledge otherwise. But then hopefully, that’s only the first step. I mean, hopefully, from there, you have much more substantial interactions, behaviors, ongoing routines and trends with them. And that’s the purpose of the book is that we’re pushing for a much more sort of egalitarian footing for people. And that doesn’t mean that you need to go into your organization say, oh, you know, no one has a title anymore, everyone makes exactly the same amount of money, everyone has exact- that’s not the point. But, if you have some kind of authority structure, you can still say everyone in here is equally meaningful as a person, everyone’s presence and experience is equally meaningful. We might have to have other kinds of hierarchies in order to get things done and accomplish our goals, but these two things can exist at the same time.


Seth Villegas 6:30
I don’t know if I’m reading too much into this. But it seems then that both for you and Mike, there’s kinds of surrounding experiences that are kind of informing how you view this kind of a problem, would you mind taking us through – they don’t have to be like super specific examples – but the kinds of things that you experienced that seemed to run into this default stance that you’re trying to correct?


Willys DeVoll 6:54
Yeah, absolutely. You know, I don’t want to speak too specifically for Mike. I know, his thoughts on on the issues, obviously, just we’ve talked so much, but I can speak more from my perspective on the kind of personal experiences that they certainly informed the ideas of the book, but I think maybe even more than anything inform the kind of energy and motivation to pursue this particular project, as opposed to others as well. So my perspective coming into this book- you and I are the same age, right? We’ve been out of school or out of undergrad for what, seven years or something, right? So early 30s. I have been working as a writer in tech the entire time. And already that’s meant kind of bridging a couple of eras in technology, which is strange, because it’s not that long, but it kind of moved from when social media was hot, hot, hot, the absolute next thing, essentially what crypto is now is like what Facebook was at the time. Now, all of those things, all of those kinds of social media, and the grand ideas around them have kind of become highly stigmatized, and that’s probably generous. You know, within those experiences, and I think this is common to basically everyone who’s had a job in this kind of economy, you get a lot of talk about the high minded ideals in tech. And I think to some extent, that’s genuine, I think a lot of the people who started, run, and even kind of rank and file people, if it’s tech companies, to some degree, do believe in that authentically. And I think to some degree, there is meat on the bone there. On the other hand, the day to day functioning of a lot of these firms, and this has become increasingly clear, even in public, for people who aren’t anywhere near the industry, is very, very different. There’s a lot of the kind of exploitation, there’s a lot of taking people for granted, there’s a lot of really not even considering people as people, the classic means and ends distinction. And so you can appreciate that in the abstract, and then actually working in that and seeing whether it’s you or people you care about, people you know do good work, kind of be on the end of that spear. And then you know, sometimes you’re the ones holding this spears even, can be very discouraging. And so that’s the kind of animating energy for how do we create a framework for saying that we have really important goals, we have really important animating missions, but that has to be blended with a sense that the people we’re involving in all of those things, either directly or are being affected as externalities are just as meaningful, because if we’re going to have these goals without taking people into the equation, I mean, what’s the point? And there probably is an answer to that. I think the point for some people will just be financial outcomes, or highly quantifiable bottom line metrics that they care about, which will ultimately probably be financial in one way or another all the time. But then you’ve given away the game, if you can see to that being the only thing you care about, then that’s a meaningful concession.


Seth Villegas 9:11
I’m really glad you’re kind of putting it this way. Because I think as I was reading through the book, I really got that sense of backdrop of the tech industry without it being spoken about. But I think that kind of speaks to our common experience of being educated in Silicon Valley at Stanford, living in Silicon Valley. And then kind of seeing the same patterns repeat over and over again, of oh, hey, like, we have all this stuff for you to take breaks whenever you want, so long as you’re working 60 to 80 hours a week, or there’s all these kind of undercurrents of really pushing people to work as much as they possibly can and to extract as much work as they possibly can because of the timing of everything. And I’m really glad you mentioned social media too, because those kinds of games of trying to take hold of the algorithm or to run the algorithm or doing all these big analytics, people in big data wars. It really is a matter of how much data you can get how much you can process and analyze CPU power. Like all that stuff’s kind of in the background of this. And I think it’s hard at that point to see that the data points often refer to specific individuals or people even as you’re doing any kind of internal analytics. And I kind of got that sense, too, of when you’re trying to push for productivity and efficiency through even the application of data processes on your employees, that’s maybe not necessarily good for your employees. And I couldn’t help but keep thinking about that, as I was reading the book, I don’t know if that’s something you were thinking about.


Willys DeVoll 10:32
Yeah, absolutely. And there are kind of two opposing forces in how we structured this book, audience and content-wise, which is, on the one hand, I think, when you’re talking about the workplace, and businesses, and maybe businesses isn’t even the right term, because like a large 501c3 will kind of have similar kinds of things going on in this respect, you have kind of large organizations, they have to be managed in certain ways, you have things like performance reviews, and you have complex sociological networks inside of the organization. But that kind of corporate, in one way or another, organization is a really good petri dish for a lot of these ideas, because they have these cultures and subcultures. And these things manifest themselves very clearly. But on the other hand, we want it to be very clear that you could do this in essentially any realm of your life. And so that could be in relation to your family, it can often feel very uncomfortable for people to think of themselves as a leader in their family, but that’s clearly the case for people in either romantic or familial relationships. It could also be true in groups of friends. And it could also be true that each friend in a group of friends is stepping into this position of leadership at various times in various ways, often simultaneously. And so we wanted this kind of diverse and highly accessible image of leadership, because as soon as you make it about valuing other people, it doesn’t need to be about instructing people to do things or setting grand strategies. Now it can include those things, but it doesn’t necessarily need to. As it relates to what you’re saying about the sort of exploitation of the workplace, at some level, we structured this book as a very back to basics book. So it has, as its backdrop, these business concerns with technology, with every accelerating technology. But almost everything that we’re talking about explicitly in the book, the context is the technology, but then the actual kind of prescriptions that we have, to the extent that they’re explicit prescriptions, are quite old fashioned, in many ways. They’re about building relationships, as the title suggests, they’re about kind of building these very classical ideas that are important between people like trust, like accountability, stability, I mean, these things are not new. And so in that ways, it’s really kind of back to the basics concept. And so yeah, how do you get these ideas in the context of a world that looks increasingly foreign to where a lot of these ideas came from?


Seth Villegas 12:36
Yeah, it certainly does. I don’t want to spoil too much of the book, but I think in- the word that comes to mind, for me, is something like character, something like virtue, and even as you’re talking about kind of the conclusion of the book, about things that are unquantifiable within relationships that make them work. That it’s not a matter of oh, if I do X activity per week, for my partner, it’ll just be good or something right, you can’t run some sort of an algorithm to get the kind of outcome that you’re trying to achieve. And I think that when you’re talking about that, I also do some some virtue ethics, and that’s partly why I’m framing it that way, of being the sort of person that can operate a little bit differently, or that can understand different circumstances in people’s lives or difficulties that come up, because a lot of the stories that you share, often, there’s some pretty harrowing ones in there, right? Of people overcoming some pretty serious things, lots of military people, I think in particular, I was noticing a lot of that sort of stuff, having to push through really difficult circumstances and having to find people to rely on to get out of those sorts of things. And if you only have these sort of shallow relationships on the basis of economic transactions, well, you’re not going to really have anyone there in your corner, necessarily, if things suddenly turn on you. So I was definitely thinking a lot about that. But rather than getting to that, I’d love to hear a little bit about your relationship with your co-author, if you wouldn’t mind sharing, how did you meet Mike, and how to do to start to dream up this particular book?


Willys DeVoll 13:59
So Mike, and I first met in September 2012 at West Point, you know, it’s it’s Military Academy. He, at that time, was active duty in the army. He’s a graduate of West Point, and he was on the faculty there. So he was responsible for organizing what is now the McDonald Conference for Leaders of Character, and that was the inaugural meeting of the conference. I attended. At that time, I was still at Stanford, and Mike and I met. It was a relatively small conference, a relatively small number of attendees. He and I met kind of started our relationship and kept in touch over now, it’s been almost 10 years, but we had talked about various projects that we might be doing, so it had taken different guises. But we had started talking seriously about doing something together several years ago, and it kind of slowly shifted into this book. It was a couple of other things before this book that were quite different in form and in content. But once we kind of zeroed in on this, it happened pretty quickly. So we did the interviews, we did some initial interviews, turn that into the proposal and once we were able to get picked up by Wiley, who was the publisher of this book, then we kind of rushed full speed into the full set of interviews, and then it was just kind of aggregating those, finding the common themes, and then drafting it into the book that it is today. So yeah, at the most fundamental level, the book is a product of something like what we’re preaching in the book. It’s a product of valuing people, staying in touch with people, not having a particular material goal in mind with that relationship, but then it’s often the case that if you have that underlying bond, that something might come out of it that’s not just that underlying brand kind of started with happenstance really, and has kind of coalesced and solidified over time.


Seth Villegas 15:31
Okay, that’s, that’s really great to hear. I think that also explains a bit of- the interviews kind of have a wide range of people you have like Olympians, which is really cool to see, you know, Kerri Walsh, Apolo Anton Ohno, really great to see as well as lots of military people; I was actually wondering if Mike had some of West Point background, but I think that definitely makes a lot of sense, given the the content of the book. And I guess I’m sort of noticing there is, if I’m imagining these kinds of more old fashioned relationships in which there’s a real person to person connection between who is the leader and you, and I mean, to go back to these kinds of more corporate settings, but in those, you can actually have leadership structure that’s so stretched, that those people are so far from you, and so removed from your experience, that you can’t really have that kind of relationship with them at all. And as I was trying to picture the sorts of businesses I would be able to implement this or the sorts of groups that are- I always imagined them, and it can only be stretched out so far, I guess, with this kind of advice, just because there has to be that kind of direct knowledge of who the other people are and what they’re up to. Is that kind of what you two are imagining?


Willys DeVoll 16:35
Yeah, I think- I think that’s true, I think there are probably, you know, harder to immediately imagine because they’re just less obvious, but but nonetheless, valuable versions of it when you have the kind of structures that you’re talking about. So the closest person, I think, in the book, who addresses this directly is Dan Streetman, was the CEO of a large company in Silicon Valley. And he’s well aware that he’s not going to be able to talk to every single person in his organization every day, of course, of course. And so he talks about the various strategies he uses, you know, as soon as you hit a critical mass of people, and that’ll probably vary based on your personality type and exactly what kind of organization you’re in, it could be 10 people and then hits a limit, because you just need to be interacting with so many people so rigorously that, you know, above 10, it’s impossible to continue doing that. But maybe it’s much larger, maybe you don’t need that kind of interaction, maybe it’s 100, whatever it is, I think the principles remain exactly the same, because the principles are, again, very classically, and quite simply, we even say at various points in the book, like, hey, what we’re saying here is not complicated. We just want to give different examples and different glosses on it. But the idea is, essentially, Mike is very fond of this phrase, that other people matter. And so how do exactly you enact that in a company of 20,000 people? Well, I think the principles are going to be largely the same, you have to treat people as ends in and of themselves, you have to treat them with the kind of inherent dignity that isn’t necessarily obvious and often can be disincentivized, especially in corporate structures, you have to take people’s opinions into account, you don’t need to do everything that everyone ever provides feedback, of course, you still have to be decisive, and you have to make difficult choices. But you know, again, kind of going back to this basics of if you proceed from other people mattering and you proceed from everyone is inherently valuable, then exactly how you enact that is going to take all of these different guises. But I think one particular step you can take, if you’re in this kind of huge organization structure, maybe you’re at the top of it, or near the top of it, is of course, you’re going to want to treat the people around you well, but you can also make proactive steps to kind of talk to people at very different levels of the organization. And if you’re at the very top, that’s probably going to mean something close to the very bottom and actively soliciting their feedback, actively understanding what they’re dealing with, what is their experience coming to work every day? What is their experience interacting with these other people? And taking that as seriously as you would take a briefing from a vice president. And again, you want to be careful, because this can sound very pollyannish very quickly. But that’s really the strength of having this interview format, from our perspective, was your people who’ve done this at a really high level, and here’s exactly what they’ve done in their idiosyncratic experiences to enact this. Because otherwise, it can really just sound like platitudes. And so the particular examples matter.


Seth Villegas 19:04
What you’re saying this responsive to a real phenomenon, and part of the reason why I brought up bigger structural things, I think of something like Undercover Boss, for instance. It’s a show that its whole premise is based off the fact that the CEO doesn’t really know the on-the-ground experience of employees. The whole basis of the show is around that. You know, often there’s some sort of a release of some kind that comes from, oh, this person’s having a tangible problem related to money that the CEO can help with that they know about as part of the show. But kind of as you’re describing, though, we wouldn’t even need to have a show, though, if something like that was already happening. So when I think about that sort of stuff, I do think that’s really important. But I’m also thinking of things like remote work these days, of kind of the changes in the workplace that might lead to an increasingly distributed experience of work in which it’s even harder to get to know people because you don’t necessarily have those unplanned interactions. It’s you meet with somebody in the coffee room, or maybe you grab drinks with other people after work. And if you have a different kind of a work popping up, then I would think especially post COVID, even this sort of thing, I think there are new challenges to that.


Willys DeVoll 20:13
Yeah, 100%. And we talked a little bit about that in the book, because we’re lucky enough that this book was turned around quickly enough by our publisher that we’re relatively responsive to current events. And we didn’t want it to be kind of a minute by minute take, for obvious reasons. But we’re able to talk a little bit about that remote work element. I think, you know, one thing that’s very clear about remote work is there’s the obviously really bad version of it, which in some ways, is not new at all. And it’s essentially, hey, let’s say I can have three people in the office coming in every day as full employees getting full benefits, being a part of this network, and contributing in ways that aren’t always necessarily quantifiable, or at least ostensibly, I can get someone somewhere else, I don’t even really care where it is, to do ostensibly the same work faster by one person, or the kind of financial equivalent of one person, and not only am I gonna have the same work for less money, but I’m not gonna have to deal with all this other stuff, which is essentially the kind of messy work of relating to other human beings. That’s obviously bad. I don’t think any living breathing person is going to disagree with that to the extent that they do, again, it’s kind of giving up the game, that the only thing that matters is kind of pure financial efficiency. And at some level, anyone who’s going to say that and is going to concede like yes, all I want is pure financial efficiency, then I don’t think there’s even enough common grounds to continue the conversation. So there’s that version of it. I think, one thing that I saw in my own personal experience, but then also heard from a lot of other people who are kind of similar age working in tech, or- it doesn’t even matter that it’s the technology industry because at some level tech has kind of become so similar across so many different industries at this point, especially in the knowledge sector, at least, that there were a lot of efforts by companies to maintain the quote unquote, culture, especially during the beginning parts of the lockdown when people were very upset, understandably. They have very little social connection, were extremely lonely. Morale was very low, particularly in a work setting. And people running these big organizations were very concerned that this was going to result in both severely decreased productivity and potentially turnover and attrition and the ladder we’re clearly seeing with the whole great resignation theme lately. Now, I think those are both reasonable concerns, productivity, probably less so especially when you have this once in a lifetime cataclysmic event, but at some level, you do need people to continue doing something. Attrition, that’s a whole complex topic that would probably warrant its own episode. But what people did in response to that, I think, is quite telling. So there were a lot of really contrived ways to get people to talk in ways that completely missed the point, at least in my view. So this might be my own kind of personal hobbyhorse. But the kind of icebreaker before a meeting of whatever kind, and again, this doesn’t necessarily need to be corporate, but we’ve got people who like kind of know each other, maybe don’t totally know each other. So we’re going to ask one like, really contrived question that because we’re in a kind of professional or at least somewhat diplomatic setting, people can’t really answer honestly, anyway, it’s a relatively superficial question. But it’s also a kind of, quote unquote, offbeat question. And so kind of answer the question, and this will allow you to better relationships with the people in this room, and then we’ll get back to business. On the one hand, I think that’s clumsily charming in intent, but seems to miss the point of actually having substantive relationships with people. I mean, you really have to get to some level of intimacy, you really have to get to some level of time spent, something we touch on in the book is some kind of formative experience is often very helpful. That doesn’t mean you need to go through the most traumatic thing in your life side by side with someone, but something a little bit beyond a random question that you can only answer somewhat honestly in the course of a workday, you know, something a little meatier than that is often very important, maybe not necessary, but certainly helpful. And so yeah, I think it’s a huge challenge of how you bridge this, because it’s really clear that in person interactions are going to be more effective at creating these kinds of relationships; I don’t think there’s any reasonable argument against that. But at the same time, at least to me, that is not dispositive that remote work is bad. I mean, quite the opposite. I think you could say, hey, remote work is a net positive for basically everyone involved, and at the same time, that leaves out this really important piece. And so some of the obvious solutions are, you know, we meet in person and do something at regular intervals. Is that going to be possible for everyone? No, but I think that’s, you know, one possible way to do it. You know, the other is to like, actually have time for people to have the kinds of conversations, even remotely, that form relationships. And so that could be, like at the end of the book, we have questions that you can ask someone that are not deeply, deeply probing and probably won’t make too many people uncomfortable, but are a little more than like, what’s your favorite color? Or like if you were going to be a dinosaur, what would it be? Because they allow people to say something about their own personal lived experience. Some of the questions are about kind of maturity and regret, like if you were to go back to high school, what would you do differently? And the point is not to be overly nostalgic about high school, but kind of what have you learned and then what does this say about you and what you value, these kinds of questions. And you know, it’s uncomfortable. You don’t want to put people in an uncomfortable position, especially if they’re in a professional setting where there is, no matter how great the organization is, an element of financial coercion. But you know, I think that’s where emotionally astute people kind of up and down the organization, who think of themselves as leading, whether formally or informally, come into play of, hey, how much can people handle? How much is opening a door to vulnerability and intimacy without putting people in counter productively uncomfortable situations where they feel like they have to answer these questions, they have to put too much of themselves on the line, they feel kind of affronted in particular ways? And that’s the sort of thing that you’re not going to know unless you know the people involved quite well, and are constantly taking their experiences seriously, you can gauge this as too much, there’s too little, and you can constantly adjust. But you’re not going to get that from quantified measures, or just full stop best practices, you really have to be on the ground to understand that.


Seth Villegas 25:33
Last year, a lot of the trainings I had to do as part of my university responsibilities were all remote. And as a result, the people I was working with, I just didn’t know as well. And this past year, as BU’s had a chance to transition a lot of that stuff to in-person. And it’s hard to describe how much better it was. Like all the information obviously is a lot more convenient to just be taking in passively, you know, whenever I have time, maybe I just want to blow through all of it. But being there with other people even kind of goofing off during a training or something, I hope none of my supervisors are listening to this. But just during those kinds of moments, the breaks and attention, are really humanizing in a strange way. And you get to see different sides of people. And to me, it seems like you have to kind of get past those niceties a little bit. You know how like, oftentimes, this is especially true for first year grad students, freshmen in college, probably first day at the workplace, you have kind of the same conversation with everyone that you meet that day. And it takes other interactions after that before you finally get the stuff and you actually never know what you’re going to connect with someone on, right? I actually found that one of my co-workers was in similar music kind of random. It’s just sort of stuff that it wouldn’t even think to ask about, but you just kind of discover. And as I’m thinking about the sorts of stuff in the book, it seems like that process of discovery, of intimacy, of picking up on those things, as people start to reveal different parts of themselves is really core to having a more holistic view what a person is. And I think that goes for all the different contexts that are missing, not just business, right? Family, friends, of that’s what makes those relationships worthwhile is the kind of surprises that can come out of that.


Willys DeVoll 27:13
Yeah, 100%. And it also makes me think of the emergence of the concept of personal branding. And I don’t know exactly when this started, but it’s relatively recent. I don’t know that it’s made things better or worse, on the whole. I mean, I think it’s easy to say, Oh, this is kind of a deleterious thing that’s kind of eating away at us. I’m not sure that’s actually true. I think that’s probably more technology pessimism than anything. But I do think that people across essentially every line of work, and certainly even in just platonic and social relationships with the way social media is now, there is a much stronger emphasis on kind of how you categorize and identify yourself in a relatively pithy way. And so yeah, I think that kind of superficial conversation, the small talk conversation, the stock questions that you’re that you’re talking about, the niceties as you as you phrased it, not that there’s anything wrong with that, but I suspect those are less effective than ever precisely for this reason, like people have their talking points and their kind of self identification message discipline better than ever. Again, I can’t prove this, but I’m relatively confident. It’s true anecdotally. And so we all kind of know how to go through those questions, because we do it so often. We have to put it in a Twitter bio we have- you’re always doing this in a way that I don’t think previous generations did. And so in addition to those not being especially meaningful or full of content, I think now just the actual experience of going through them of both listening to them, and especially reciting them yourselves is kind of distanced and detached because it’s it’s robotic, its so wrote as to not be kind of meaningful speech act anymore. This might be a little too abstract and academic, but I do think there is a sort of, someone asked me this question I know how to respond to I will pull the string on my back and zone out for 45 seconds until I’m done with the spiel.


Seth Villegas 28:46
I’m really glad you’re bringing this up, in part because I think for people our age in the 20s to 30s today, there’s so many informal contexts in which you have to do that, especially if you live in a city. Just thinking about my experience here in Boston, where lots of people come and go, so every year too I kind of need to meet new people, make new friends. So there’s always kind of people coming in and out. And so you don’t have like a clique kind of, for better for worse. And I think anybody who’s tried dating apps, but also the same sort of things, like you run these kinds of profiles of yourself, or you can even try them out in different contexts as you’re meeting so many different people all the time. And it’s just very strange that it’s like that, whether it’s going to some sort of a sports league or going to some sort of a bar event, those kinds of interactions have really changed even from the time that we were in college precisely in part because of the ubiquitous nature of the digital trail that sort of follows us or even Oh, look, I need a good picture of this event even though I hate it for my Instagram page. And because that’s the the contradictory thing about personal branding is it’s supposed to be polished, refined, accurate, but also authentic at the same time. It’s a- it’s your business and your businesses you, right? So you kinda have to put forward this, this good face all the time, right? Even if it’s not necessarily how you’re feeling and whatnot. And I remember this because even as I was trying putting forth of the podcast and stuff, you know, personal branding is obviously a part of the things we’re doing. I was like, oh, I should probably actually tell people what I’m doing in my life, so I’m not just shilling my podcast every week on my social media, maybe that would actually be better. But I think that even speaks to the kinds of things that you’re advocating for in the book of oh, I need to think about the kinds of relationships that I have with the people in my social network so that they don’t feel this sense of, I’m just peddling something that I have at this particular moment. Because I do know people like that. I don’t know, if you have this way, you know, I’ve definitely been shilled some pyramid schemes in my time. So like, people do view each other like that sometimes. And I’m personally not wanting to do that, but we also live in this weird time in which to even manage that kind of social media verse of our self is itself such a chore.


Willys DeVoll 30:55
Yes, I completely agree with everything you say. And to that very last point of yours, there’s something very interesting to me, and maybe this is just the sort of like writerly tendency, but it’s all of that and it has to be almost constantly updated. Because if you have the experience of you know, maybe it’s your best friends, I mean, you know very well, and you see one of their profiles online, and it’s clearly from three years ago, maybe not even the content, right, so let’s, let’s just say it’s a, it’s their Instagram profile. Maybe they’re putting up a picture every single week with consistency, and it’s up to this week. So there’s no kind of staleness there. But then even just the bio or description part of that profile is clearly a sort of strategy of self presentation from a previous version of that person. At least to me the experience of reading that is very jarring. And I don’t even know exactly why other than to say that, clearly, my brain assumes that all of these things are going to be constantly updated, and fresh and consistent with the current personal positioning.


Seth Villegas 31:50
Right, including all the past stuff, which sometimes has to be cleaned out to be consistent.


Willys DeVoll 31:54
It’s kind of a- like you mention, you do become a sort of personal business, because this is exactly how you would talk about a rebranding for Nike or something. You know, it’s like everything has to be kind of revised, removed or added and then positioned in such a way that there is a coherence. And in some ways that bears resemblance to pretty old philosophical ideas about the cell. But it does have a pretty substantial aesthetic and psychological burden for people.


Seth Villegas 32:17
One of the things you do talk about in the book on this topic is related to CrossFit. You give the example of people kind of really putting their money where their mouth is, so to speak, really disagreeing with the broader CrossFit company in relationship to I believe it was BLM, please correct me if I’m wrong on that. People who are very prominent making their money off of CrossFit deciding to actively distance themselves from that brand. And there’s something very poignant mentioned there about going beyond social media activism, which I think is also a big part of this projected image that’s a big part of our current social sphere. It really kind of hit home for me because it was nice to see like an actual example of people doing something like that. Whereas I am a little bit cynical of writing ideas about petitions because it never seems to do anything. So I guess I was wondering, were you thinking about similar things when you were interviewing those CrossFit athletes about what they were going through?


Willys DeVoll 33:15
Yeah, so the two CrossFit athletes that you mentioned that we talked to Chandler Smith and Noah Olson, and then they also were in communication with and inspired partially by a third athlete who didn’t talk to, Katrin Davidsdottir. So Noah and Chandler had an existing relationship, and they’re both very, very prominent in the competitive CrossFit world. So in the book, we have the full story, but basically, there was a huge controversy and rightfully so around the reaction of the head of CrossFit after George Floyd’s killing. It became really clear that people who supported the Black Lives Matter movement and also were, if not specifically BLM supporters, very uncomfortable with downplaying the George Floyd killing, that it was not going to be consistent with their values to continue supporting this organization insofar as it was not only not responding to the George Floyd killing, but kind of really actively insulting people who thought that this was a problem. So Noah and Chandler had these large social media followings, still do, and basically combined the social media activism with pretty old school coalition building. I mean they’re in the coalition building chapter of the book is examples of how you do this. But I think to a lot of people who were interacting with them primarily as consumers of their content, it would look like they put up these posts, and they had these thoughts exactly what they were doing wasn’t entirely clear until they said, Hey, we’re not even going to participate. So that in and of itself is far beyond what you see in a lot of this kind of purely social media activism, because both of them had money and a huge amount of career prestige wrapped up in the CrossFit Games, which is kind of like the Olympics of CrossFit. That’s by far their biggest opportunity to advance their career, secure and potentially get more sponsors things like this. I mean, it kind of largely hinges on their performance at this event. And so they said, you know, we just can’t participate at all, we can participate in this event that is hugely in their personal interest to participate in. So that in of itself was quite bold and and beyond just kind of superficial social media material, but then they went beyond that even and basically worked the phones to get more and more CrossFit athletes to do the same thing, to boycott the games entirely until they reached a point where it wasn’t going to be tenable for the CrossFit Games to happen at all. And so I think this is the best case scenario for how you get some kind of activism or real action in the real world based on social media where at some level, the social media element starts the whole conversation. And you know, starting a conversation is such a kind of vacuous phrase, there’s no actual conversation that occurs and nothing is started. But in this case, there really was a number of finite meaningful conversations that happened because of social media content. And then it was just essentially kind of the way politics happens, talking to people one on one, understanding what their concerns were. Chandler talks about, he would get on the phone with different athletes who had heard a version of why the boycott was happening, or why CrossFit was problematic, and it didn’t resonate with them, for whatever reason. And so he would talk them through in great detail his story, what his objections were, what was important to him, how this wasn’t aligned with what was important to CrossFit, how the boycott played into that, and that just gave people different valances by which they could find personal meaning in the action. And so then they would join the boycott, because Oh, you mentioned this one thing, I hadn’t really thought of it that way before, that’s really important to me, that’s something I think about every day, I hadn’t realized it was related in XYZ ways. When the whole book is probably, at the very least, it’s one of if not the most startling examples of how you get this online-offline interaction that that actually does produce something. And it’s not just another Twitter fight. I mean, it’s really changing how the material world functions.


Seth Villegas 36:34
The thing that comes to mind for me now is what you had mentioned a lot earlier about high minded idealism and not really living up to that. And I think in this case, it sort of shows that if you try to live by those yourself, as these two people did, you can actually be persuasive in other circumstances. And these are offline conversations, which I think is also probably important to mention, not something that’s happening between two people on Twitter with 100 people commenting on each reply, it’s some other kind of conversation. And even the small story that you’re just sharing here of people aren’t even getting the right story, as it would be told by the original person as it filters out to these other people. There’s actually information loss that’s occurring on social media, which I think is really important these days where the the message, and we don’t need to get into communication theory, the message gets distorted somewhere along the way, and it doesn’t reach people in the way that it’s supposed to. And I think if we’re thinking about larger networks and stuff, whether that’s, a family is kind of network, across any organization has these kinds of elements to it,. That communication is so vitally important, but unless you have some context to actually realize that people aren’t even getting the correct message. there’s no way to correct that. And I think that’s one of the hardest things to assume. But for us, we know how hard interpretation is so hard, it destroyed a discipline, we could say, at least one discipline, but all these kinds of misunderstandings and miscommunications could be worked through in some other circumstance, but that actually takes effort, it takes energy to really make those things work.


Willys DeVoll 38:09
Yeah. And it’s, I think it’s important to say, this particular story, the problem really wasn’t misinformation, which is if you read the Washington Post, the New York Times, and you think the number one issue in society by far every single day of the year. And I don’t mean to downplay the importance of misinformation, or the deleteriousness of it. But as you say, the problem is not misinformation, it’s just you have an opportunity to express a highly attenuated version of what you want to say, because of the nature of the platforms. And so if you want to put something on Instagram, you can say a strong message, right? But you’re not going to have every single nuance that we have as human beings who have complicated feelings and are thinking about complicated issues. And so in some ways, I think that phenomenon of, Hey, there’s this thing that can be the kind of inciting incident. In this case, it’s a social media post, but unless you’re willing to go in and excavate it with people individually and kind of find the common ground and understand what people care about, and get into these often quite uncomfortable conversations about how people think about things because of their really particular circumstances and how they grew up and how they got here, and where they are now, and all of these idiosyncratic situations that we bring to how we think about things. Then if you’re not willing to do that, you will always exist at this surface level interaction, not only with ideas, but with people and with kind of the whole world in some respect. And so I think that story, I never really thought about this until now. But the way you’re talking about it Chandler’s story of doing that two tiered interaction with people, like megaphone and then the telephone. is really a useful heuristic for how we’re talking about the entire book. You can’t just stay at the megaphone level forever. You have to spend time often very inefficiently, which is one thing we talked about, like relationships are not inefficient, they don’t scale. If you’re not genuinely interested in them, it will often feel like you’re wasting time because in some sense of the verb waste you are. That’s just the case, right? Like this is not the most efficient way to do anything in most cases. But that’s not the point. You are not going to be able to have these relationships with other human beings unless you take them as full human beings. And when you take people as full human beings, it’s full of all the contradictions. It’s full of all the frustrations. It’s full of all of this stuff. But that’s where, that’s where all the richness lies as well.


Seth Villegas 40:08
That sounds like a really good summation. So I just have a couple of questions left then. The first would be, was there any interview in particular, that really made a big impact on you?


Willys DeVoll 40:19
Great question. The one that stands out to me when I just think about the whole process of the conducting the interviews, drafting the book, editing the book, the whole process of creating this product is Dr. Virginia Hill, who appears quite early in the book. And she’s an educator, she’s a principal, and she’s in our forgiveness chapter because she approaches education in what you might consider a kind of old school way, not that it was ever the de facto way of educating. But she is much less concerned about incrementally moving test scores than making sure that when kids come in the building, they know that the adults in the building love them. Again, that feels very kind of old school, and maybe to some people overly sentimental, but it informs all of the choices she actually made. It wasn’t again, just talk of saying like, I love kids, it was enacting that in essentially every stage of her leadership. So it was having an opportunity for kids to go get some fresh clothes, if they came into school with dirty clothes because of whatever happened at home. It was providing better access to mental health assistance, it was all of these things. And then also, because you’re an educator, because you’re dealing with children, it was also baking in this is how we’re going to talk to the kids. Obviously, there’s still rules, there’s still things that the kids need to do, right? But we’re going to constantly reinforce that we care about you as a person. And whatever else happens, however else, other people talk to you, whatever else happens in your life, like when you come to school, you will be talked to and cared for as someone who was clearly valued and loved. And we talked about how she also integrated that into how she dealt with other adults on her staff, teachers, people working around the system, and how if you bake in a kind of forgiveness, then you allow people to do great things, because they know, hey, I’m not going to try to fail, but if I try something really ambitious, and it does fail, that’s part of the process. I know that these people have my back, I know that this level of forgiveness and allowance and intolerance is part of this system. And so kind of worked on the multiple levels, with kids with the adults, with the overall strategy of the school. And, you know, I think it’s really striking because one, it’s not in a business environment that we were talking about before. And at some level that almost feels like the best way where these kinds of relationships, these kinds of behaviors can you know, I kind of hate this word, but can scale because if you get kids at this formative age, we’re in school for several hours a day learning this kind of culture, learning these kinds of behaviors, being in an environment where I mean, look, I’m very fortunate to have gone to great schools when I was growing up, but they weren’t nearly as supportive and loving as this. It’s very hard to believe that that’s not going to have a positive impact on a lot of those kids probably for the rest of their lives. And so that really stuck with me. If you apply these principles to people who are one or more of young, vulnerable, in a position of need in whatever respect that that can really, if not change someone’s life, then inflect the way that they go forward with their lives.


Seth Villegas 43:00
I think it also speaks to the power of trust, when you have that sort of trust between people- you’re speaking of kind of experimentation, knowing you can fail, but you can actually have some ambition and ownership over what you’re doing within an organization if you feel that. And I think a great part of that too, and this is something you speak about in the book a lot, is when you’re just not worried about that all the time, you’re actually kind of freer to work as well. I found that to be very poignant, as I’m kind of thinking about competitive circumstances in my own life, I’m sure you’ve thought about it as well of, It’d be nice to be in that kind of environment more. I think that that kind of cooperation can be really, really powerful. And I really do see it as a cooperative relationship between, say, the person who’s trying to lead and the people who are there trying to help them.


Willys DeVoll 43:49
Yeah, and I think that’s one where if you extrapolate out what that means, at the end of each chapter, we have two things, we have a kind of big takeaways from the chapter, which is meant to summarize learning from what you’ve read, and also can serve as review later. But then I think more importantly, we have questions for reflection. And so there are three or four questions at the end of each chapter relevant to what you’ve just read, but there are no particular correct answers for and are meant entirely for introspection. They’re not really bookclub questions like you see at the back of some paperbacks. They’re meant for you as the individual reader in silence, or at least alone, to reflect on how this might affect your life, how you probably already come in thinking about these concepts based on your previous experiences, but then also how you might enact them later. And so that was a huge point of emphasis for us was that this book is only going to work prescriptively if the prescriptions are largely from the individual reader. And so we can contextualize that and give you some sense of what you can learn from these individual people, but you always have to be in this sort of reflective state if you want this to mean anything to you. And we were pretty intentional about that because if we came in just firing from the hip of, do these 10 things, that felt completely antithetical to the message of the book. That it was always going to be anecdotal. It was always going to be particular. And so we wanted to prod the reader enacting that process all the time. And hopefully that also gives rise to a diversity of approaches that we certainly could not have written into the book because we couldn’t have even thought of them, let alone categorize them all.


Seth Villegas 45:10
It’s funny, the- what was it, I Hums, the Intro to Humanities class that I had to take was Contemplation versus Action. And I can’t help but think about that as you’re speaking of introspection, and about how valuable that is, because when I do think about other books, I’d say that are in a similar genre to this one, I don’t think they’re usually prescribing introspection as much as they are, do do do. So I think that’s a really great contribution to the space. And I hope that people will take advantage of it.


Willys DeVoll 45:36
Yeah, I hope so too. And at some level, it might be less attractive to some people. But I think a lot of people want to read these life hack type books, where you just get this is how you do this, download this app, do these five habits, whatever it is, and this will be a way for you to like unlock your potential, or however it’s particularly phrased. It’s not at all what we’re trying to do. And again, I think, to some people, that’s going to be less attractive, for sure. But in many ways, it follows from some my co author, Mike wrote a previous book with a federal judge in state of Michigan named Ray Kethledge. That book is called Lead Yourself First. And like our title is fairly descriptive of what goes on in the book, but it’s historical examples of people who have essentially prioritized the degree of both introspection as we were just talking about and self knowledge in essentially difficult leadership positions. So if you’re always reactive, if you’re always kind of going off of other people’s prescriptions, you’re just not going to be nearly as effective. And you’re not going to be nearly as informed by your own experiences as someone who is more geared toward a self awareness and introspective sense of self. And so that’s something that’s not a direct pull from his previous book, but it’s kind of in the same vein of you need to individualize these things, because there’ll be so much more powerful to you if they are than if they’re just generic thought that you read in the book.


Seth Villegas 46:47
Right. I think that’s a great thought for us to end on, Willys. So where can people find the book?


Willys DeVoll 46:52
So you can find the book pretty much wherever books are sold. We’re fortunate to have pretty good distribution on this. I obviously encourage people to buy through an independent bookstore, but it is also available on the typical internet options as well.


Seth Villegas 47:04
Okay, all right. Well, thank you so much well, so appreciate you taking the time.


Willys DeVoll 47:07
Yeah, thanks Seth, this was a great time.


Seth Villegas 47:13
Thank you for listening to this conversation Wyllis De Voll. You can find more information about DigEthix on our website DigEthix.org and more information about our sponsoring organization, the Center for Mind and Culture at mindandculture.org. If you’d like to respond to this episode, you can email us digethix@mindandculture.org. Or you can find us on Facebook and Twitter, at DigEthix and on Instagram at DigEthixFuture. Willys and I touched on a number of topics. Listening back, I can’t help but think about the issue of personal branding, and what it means to maintain a digital presence. Willys gives the splitting insight about having to share the same anecdote over and over again, at work. I’ve run into this myself, and sometimes, we can almost be on autopilot because we have so many of the same kinds of interactions over and over again. Not only that, but we can’t seem to communicate all the nuances that we want to get across. As a result, we can flatten what it is that we were trying to say in the first place, especially so that we don’t get into any tricky, controversial territory. But if we avoid getting into thorny topics, then we don’t end up making any progress on those same issues. I hope that you can take some inspiration from the stories that Willys shared about really instilling value in other people. To me, it would seem that it’s only within the context of those relationships that we can do that kind of deep, collaborative thinking necessary for solving big problems. I know so many students and young entrepreneurs who are attempting to address really significant issues in society today. For some of these, technology really could be the answer. But my biggest immediate takeaway from my discussion with Willys is that it is important to invest in the people around me so that we can work collectively through the challenges that come our way. Sometimes, we will only dare to succeed when we feel that we’re actually safe enough to fail. And that way, maybe we can help each other to grow as well. This is Seth, signing off.


Transcribed through Otter AI. Edited by Julia Brukx.