Latest / Expertly Said / Jay Sullivan on Critical Thinking in the AI Era
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- Kristen Sweeney: My guest today is Jay Sullivan, consultant at Exec|Comm, LLC. Jay's the former managing partner at Exec|Comm and currently leads the firm's law firm group. He joined Exec|Comm after nine years as a practicing attorney and was previously an adjunct professor at Georgetown Law Center and Fordham University School of Law. Jay has worked as in-house legal counsel at Covenant House, a crisis shelter for runaway and homeless teenagers, and spent two years in the Jesuit International Volunteer Corps teaching English. He's an award-winning author of several books, including Raising Gentlemen, Lives at the Orphanage Edge, Simply Said, Communicating Better at Work and Beyond, and The New Nimble, Leading in the Age of Change. As a coach for senior professionals, Jay has helped leaders in academia, law, consulting, finance, and other disciplines focus on the needs of their audiences, frame their arguments, and lead from a place of authenticity. His approach is direct, his guidance is specific and tangible. Love that. Leveraging his background as a lawyer, writer, and teacher, Jay helps his clients focus on the task at hand, articulate their position, and guide others toward action. Jay, welcome to the show. Jay Sullivan: Thanks, Kristen. Appreciate being here. Kristen Sweeney: Really looking forward to our conversation. I know we've got a wide-ranging conversation planned for today, but I'd like to start a little bit with your origin story. Can you tell us a little bit about how you got into law and then how and why you made the transition over into communication? Jay Sullivan: Sure, had always one of those people who always knew what I wanted as a teenager, sort of I knew I was gonna head toward law and was glad to go to law school and and learn all the the aspects of the legal world that that exist. And being a lawyer, you can do myriad things. As a matter of fact, I'm on a panel in a couple weeks for people who used to practice law and now do something else because there are so many of us. And you'll see people use their law degrees in lots of different ways. Loved being a lawyer, enjoyed my time at Covenant House doing working directly. With runaway and homeless kids and helping them resolve a whole host of problems. And then enjoyed my seven years as a corporate attorney and working with large corporations and entities about their own legal issues. So I enjoyed all those aspects of it. At the time that I was practicing corporate law, my wife and I had just gotten married and we had four kids in five years. So we had a very packed household early on. It was pretty busy, busy Kristen Sweeney: Holy moly. Jay Sullivan: days. I had very long hours. My clients were based in London, but the matters I was monitoring for them were in California, so I had a very long day and and also was traveling a little bit and it may sound crazy, but I felt it was really important to be home for dinner and I wanted a life where I could be home for dinner. In the job I have at Exec|Comm which is a communications consulting firm, as you mentioned, I travel occasionally, well frequently, but when I'm home, I'm home for dinner. And I thought that was gonna be really important when the kids were younger and taught. and whatnot and my wife needed the physical support because it's you know it's a very busy time for your kids and it turned out to be more important when they were teenagers to have that family dinner every night and so that was a driver behind changing my pattern. I then work after dinner. I I have a pretty busy work life but I'm home for dinner and that was important to me. Kristen Sweeney: Yeah. love that. I have a similar kind of pragmatic career pivot. I have a background as a performer, I was a yoga teacher, and I was a freelance writer on the side. And when my first daughter was born, I kind of looked at my schedule and my husband's schedule and the realities of this tiny new person taking up a lot of our time and was like, you know what? I want the thing that's a little bit more stable and boring, if I'm being honest. Like can work from home and and so, you know, that is one of the big factors. I love what I do today, but definitely that how does it fit into the rest of my life was, you know, something I can relate to, part of my decision making as well. Jay Sullivan: Yeah. And I hadn't planned to leave the law. I contacted somebody who'd been the career advisor at Fordham Law School where I went, and thinking she could give me advice as to what other options in the law existed, and she had just joined Exec|Comm and she said, no, you used to be a teacher, you should come over here. You enjoy doing this. And so so recruited me there, and Kristen Sweeney: Ha ha ha she recruited you. Nice. Jay Sullivan: it had not been my intent to leave the law, but once I looked at the option of teaching adults how to communicate more effectively, I thought, this is where I belong. And I've Kristen Sweeney: Yeah yeah. Jay Sullivan: Although most of my clients are law firms. Kristen Sweeney: right. You you run the law group practice now. Jay Sullivan: Right. Kristen Sweeney: Do you find that there's a lot of transferable skill from, you know, obviously communication, but in a very specific way is a a big part of legal practice. Was there a lot you had to sort of relearn or did your teaching background sort of inform the approach just as much? Jay Sullivan: I think one of the biggest pieces of advice I give younger people is when they're when they're talking about what you know what what should I do in terms of thinking about my career and how to approach my career. The number one thing you need to do is just pay attention. If you just like pay attention, like get some of the clutter out of the way and pay attention to what's in front of you, then what happens is you start to notice stuff and things become more intuitive to you. So you asked about this, though, is it applicable to the law? When and at Exec|Comm by the way, most of my clients are law firms, but I also have corporate clients have in clients in finance and consulting. But most of Exec|Comm's clients are every industry there is, because we only work with industries where people need help communicating better, which means everybody. So we have we have a lot of and what we do is when we're talking to somebody about their own career. So if I I get a call from somebody who is a scientist and or an economist, I just got a call a couple weeks ago from someone who's an economist. His challenges as a communicator are not that radically different than a lawyer's challenges, and not that radically different than somebody else. There is a difference between people who sell products. So if you're selling a phone and you have something tangible to talk about, there's a different way to communicate than if what you're selling are ideas. And most of the people that I work with sell ideas. They're in finance, Kristen Sweeney: Same. Jay Sullivan: they're selling the difference between one financial product versus another, but that's really those are ideas. Those aren't constant, those aren't tangible things people can hold in their hands. Kristen Sweeney: Mm-hmm. Jay Sullivan: And helping people cut through the clutter to just talk about what they do and what their product or service is is what most of the job is about. Kristen Sweeney: Yeah. Do you find it easy did you find it easier to teach students or to teach executives? Jay Sullivan: Executives have a lot of the same issues that students do in terms of Kristen Sweeney: Uh-huh. Jay Sullivan: attention span. They are and when I was teaching, when I taught in Kingston, Jamaica, I had teenage boys. So it's a boys high school there, and I had 40 teenage boys in the room, and they have all the same issues that every teenager everywhere has in terms of attention span and interest in gram I was teaching grammar, and their level of interest is somewhat muted. For the executives, I tend to only deal with people who want to be in the room. Rarely Kristen Sweeney: Yeah. Jay Sullivan: am I teaching a class where people are just saying, I gotta come here to check a box and some kind of training. And they recognize pretty quickly that a marginal improvement in their communication can have a significant improvement in their effectiveness and impact. Kristen Sweeney: Yeah, I love that. And I really like your approach. I resonate with the idea of seeing the patterns. I think in a moment and and I do see this shifting a little bit right now, but sort of over the last, I don't know, many years there's been a lot of focus on right, like industry expertise, that kind of specialization and this idea that every you know, vertical, every sector is like special flowers, right? But our work certainly with content cuts across a number of different industries and the commonalities like complexity of ideas, big thinkers who don't have the bandwidth or skills to share their messages on their own. and I tend to focus more on this what they have in common than what's different about them. And I hear that in your approach as well. Jay Sullivan: The the challenge for everybody is pretty much the same. And that is that as human beings, we are all basically self-focused. And that's not selfish, that's not a criticism, that's not Machiavellian, that's just human nature. We're wrapped up in ourselves. And the biggest challenge with communicating is that we tend to think everybody else thinks the way we do or approaches problems the way we do. And we tend very often to think they already have all the knowledge we have in our head. So when I'm explaining something, of course they should get it, and of course I'm clear. And that's where the big disconnect is. And we've talked about this before a little bit. Kristen Sweeney: Absolutely. Jay Sullivan: When we're talking to somebody, we can really only talk about one of three things. We can talk about ourselves, we can talk about our content, we can talk to the audience about the audience. Those are the only things we can ever talk about. So it's ourselves, the content, the audience. Well, nobody cares about us, nothing personal, but nobody cares about me when I'm talking, they don't care about you when you're talking. It's never about us. They don't really care about our content either, and that's a really hard thing for us to hear because we're all Steeped in our content. We love our content. Nobody cares about our content. They care about how our content impacts them, which is different from the content itself. So if a lawyer is explaining to a client the tax code changed, and here are the changes in the tax code, the client doesn't care about the changes in the tax code. They care about how is that going to impact my ability to get my deal done. So instead of talking about the changes to the tax code, you talk to the person about the impact to them. Kristen Sweeney: Yeah. The you know, in writing, I think this is often referred as like the so what, right? Like, okay, here's something, so what. I prefer so that. So in my yoga teacher training, we would talk about lift your leg, your right leg up so that you can stretch your muscles or so that you can do like really giving the the why of it right embedded Jay Sullivan: Right. Kristen Sweeney: with the instruction or the which would be the content in this case. So yeah, makes a lot of sense. Jay Sullivan: a Simple example, 'cause it's it's easy to say, focus on the audience, but what does that mean? Because we're always telling people You always ask yourself, why is she reading your email? Why is he listening to your talk? Why are they attending your meeting? And if you think about what the other person's trying to get out of it, it changes the way you structure the information. And just a simple example as to what that means in execution. Most people go into a meeting and the when it's their turn to share their item or their issue, the first words out of their mouth are what I wanted to share with you today is this. Or what I wanted to tell you. Wanted to make sure you knew what I want to make sure you walk away with. Now you start with the words what I want, as if anybody cares what you want. You know, nothing personal, but nobody cares what you want. So if you get away from that language and instead stu substitute in what I thought might be helpful to you, you're not only making the issue about the other person, but you're challenging yourself to say, if I'm going to start by saying what I thought would be helpful to them, why do I think this is helpful to them? And how Kristen Sweeney: Yeah. Jay Sullivan: do I time it? Meaning, do they need this now or tomorrow or yesterday? How do Kristen Sweeney: Ha ha Jay Sullivan: I share it in a way where I minimize the details or only share the details that they care about? And then how do I share it in a way where I eliminate the jargon and the acronyms so that people can understand it? So just go from Kristen Sweeney: Actually follow along. Yeah, absolutely. Jay Sullivan: what I what I wanted to share with you to what I thought might be helpful to you. Makes a difference. Using the different words makes a different impact in how we then think about the issue and share it. Kristen Sweeney: And I love how you follow that up with okay, and now you actually have to consider what is helpful to you. Yeah, yeah. Jay Sullivan: Right. Yeah, it's not just it's not just semantics. It's not just semantics. It's and you it's not just I'll I'll use that language. No, you actually have to think about why is this more helpful to you. Kristen Sweeney: Yeah. I I was just going through it's similar different but similar about the idea of finding the true substance of it. A client and I were going back and forth and it was like, Okay, we're using this term sort of in two different ways in back to back paragraphs. And it was like, Well, which should we use? And was like, Well, what is your opinion on this? That's what we have to start with. It's not Which phrase sounds best. It is what do you actually think? Let's make sure you crystallize that because we are working through something in real time. And then now I know exactly how we need to wordsmith it accordingly, but it's gotta start with that clarity of what you're trying to say. Yeah, Jay Sullivan: Absolutely. One thing that might be helpful to your audience. When you go to give a talk to somebody or you've got to give a presentation, I hesitate using the word pres presentations. First of all, if you're giving a presentation, do not use the word presentation. Nobody wants to be presented to. I'm not here to present to you on the latest developments in AI. I'm here to talk to you, or we're here today to talk about this issue. So get Kristen Sweeney: Mm-hmm. Jay Sullivan: away from that presentation word. But when you do have to go give an an official like, I gotta get in the room and I gotta share this piece of content, always ask yourself if this audience only remembers. One sentence of what I'm saying, what is it I want them to remember? Like what do I want them walking out of the door and what's resonating in their head? So when I teach a program, I always think about who's the person who signed up for this but then couldn't make it to the session? And when the people in the room leave and they bump into Jack who couldn't make it to the session, and Jack says, so what was that about? If the person says, I don't know, the guy just rambled on about communication skills, then Kristen Sweeney: Ha ha. Jay Sullivan: I had zero impact. Zero impact. But if they walk out the door and they run into Jack and he says, what was that about? If they say the main idea is you've got to be less focused on yourself and really focused on your audience, then they got the main message. And then hopefully they got 15 things to do to implement Kristen Sweeney: Yeah. Jay Sullivan: that. But they got the main sentence. So what's your Kristen Sweeney: Yeah. Jay Sullivan: main sentence? What's the one sentence you want them to remember? Kristen Sweeney: It it really is so much simpler than I think we try to make it you know, we work with folks in a lot of very technical and comp there's a lot of complexity in what they do. And it is so easy to get lost in the sauce, right? And say, yes, all those details are important. As you said, they have a time and a place, and some people need to know every last detail, and others for others it's not as relevant. But you do have to be able to articulate. something quite simply and I'm gonna I'm gonna use that brilliant segue to give you a chance to talk about your book a little bit because I know you shared some of these ideas. Your book Simply Said has a second edition or an updated edition coming out. Can you tell us a little bit about the book and what's new in the update? Jay Sullivan: Sure. So the book simply said, Communicating Better at Work and Beyond came out 10 years ago. And it is, although it has my name on it, it is the collective wisdom of everybody at Exec|Comm over the last 50 years on how to connect with people better. And so we talk about how to structure your message, we talk about your physical delivery skills, your listening skills, certainly. We talk about writing. So there's a whole section on how to write more effectively, and I'll comment on that a little bit when we talk about AI. Then there's a section on the different settings. In which you communicate. So giving people feedback. So if you're a manager and you've got to delegate delegate an assignment or give feedback. Or if you're running a client meeting, how to make sure that client meeting goes most effectively. If you're giving a toast. So three years ago, three of my four kids got married within 12 months of each other. And we were given a lot of toasts. Yeah, yeah, yeah. So, Kristen Sweeney: you guys really like to batch things up. Jay Sullivan: yep. There are all different settings. And the last section is all about leadership. And but the main idea is how in all of those settings, the theme that keeps coming through is how are you less wrapped up in yourself and your content and more focused on how the audience needs to use that content. That's what makes a real difference for people. And so the book it's been out for 10 years. I check the stats every morning, every Friday morning I get the stats from the week before and still sells about 80 copies a week on Amazon, which is fantastic, but it's over 100,000 copies. Kristen Sweeney: Nice. Congratulations. Jay Sullivan: And the publisher said, it's time for an update. But you need to, when you do a second edition of something, you need 25% new content, which is not a problem. There were references to fax machines in the original version, and now it's all about not just in-person meetings, but this kind of setting. How do you interact Kristen Sweeney: Yeah. Jay Sullivan: with people virtually? How do you think about AI? How do you incorporate the crazy ways in which we communicate now? Kristen Sweeney: Yeah, I love that. I am gonna be picking up a copy of the new edition when it comes out and checking it out. So I'm really looking forward to that. Jay Sullivan: Appreciate it. Comes out October 13th. Kristen Sweeney: awesome, awesome. hearing your bio, there is a humanitarian theme kind of running through your career. And I'm curious what you've maybe brought from those experiences to the work that you do now, which is, you know, much more corporate working with executives. and I'm guessing you're gonna have a great answer for this because you are a pattern identifier, right? Who sees like those common threads. So can you connect the dots for us a little bit there? Jay Sullivan: Sure. So when you think about the theme of what we do at Exec|Comm it's less about you and more about the other person. We didn't invent that. Like we did not invent that concept. Like that's been around for Kristen Sweeney: Sure. Jay Sullivan: a very long time. It's all about in the immediate world that w that business professionals work in, how does that play out? So I am thrilled that I've had 27 years at Exec|Comm where all I do all day is teach people how to be less wrapped up in themselves and how to think more about other people and how those people, very specifically how those people are digesting your message. At i in a corporate setting in particular, people think that they're valued because they're smart. Now, there are lots of smart people out there at your organization, whatever organization you're at, if for your listeners, there are lots of people who are smarter than the people who seem to move ahead of them. At work, we don't get valued for being smart. We get valued for having impact because we're smart. But if you can't take how smart you are and turn it into something meaningful to someone, someone else, then your career stalls after a while. But that idea of you asked about the humanitarian end of things. Kristen Sweeney: Mm-hmm. Jay Sullivan: You know, I spent two years living in a convent in Kingston, Jamaica, helping these nuns run an orphanage, which is what I was doing while I was also teaching at a different school. And that formed a lot of who I am and how I think about things. And then the two years I got to spend at Covenant House working with homeless kids on their legal issues really forces you to say, I have to think really carefully about the language. I use because it has to resonate with whoever I'm talking to. I have to listen better because I can't be of service to someone else unless I understand that someone else. And that means understanding their experience in the human experience and how we approach the world. And all of those things remain true when you're coaching a business professional. So that idea of saying, I need to step back, and by the way, because we're communications consultants at Exec|Comm people think. we spend all our time teaching people how to talk. We teach spend far more time teaching people how to listen. It's all about gathering the information so when you're talking to somebody, you actually have the right impact. Kristen Sweeney: Yeah, I love that. what I'm kind of hearing is I think a thread underlying this is the concept of you know, empathy, considering others' needs. I'm hearing something that it's not just transactional free, right? It's not, I consider what they need so that actually I can get what I want out of this, but it is more that truly in service of others. and I think s you know, certainly your human humanitarian work affects that, but I'm hearing that that is how you approach this, you know, versus more of a cynical, like, all right, we gotta tell what what's in it for them and you know, so that we can get what we need out of it. yeah. So Jay Sullivan: Right, right. But that's where that's where the asking questions and the listening comes into play. And no matter how good anybody thinks they are at this stuff, we all need to work on our listening skills. It's just we're we have to constantly improve these things. My wife and I have been married for 35 years, and on occasion she will still say to me, You teach listening skills? Because like I'm clearly not listening to what she's saying at a certain point. But the idea of being present to other people and trying to understand their needs is really important. And one of the challeng one of the most effective aspects of being a good leader. Or if you're a leader in your organization, I get I'm blessed to have the opportunity to work with a lot of senior leaders, is they tend to come across as somebody who listens really well. So I did a program recently for senior consultants at one of the big four accounting firms. And we were talking about executive presence. And I asked them, what does executive presence mean to you? Like what adjectives, and I want you to think very specifically about somebody you know in your business life who has really good executive presence. Start throwing out adjectives for me as in terms of what those people have. And whenever I've done this, uniformly, the first thing people list is that those people listen well. And it's always they listen well, they take the time and spend the time with you, they are willing to understand your position. the words that never make the list of who has executive presence are really loud voice, really forceful delivery. It's never that. It's always the empathy. And that's what gives people, if you're conveying that, that's what tends to give people better executive presence. Kristen Sweeney: That's awesome. I'm thinking about you and I talked offline about this, but I went through the Goldman Sachs 10,000 Small Businesses program. And we did not focus on thank you. Jay Sullivan: And kudos to you. Kudos to you, 'cause that's not easy to get into. Yeah. Kristen Sweeney: the big culmination for our group was we went to the headquarters for a few days and when you say executive presence the many of the folks there. And I I think it is a very intense process that molds them in gives them that kind of charisma that they have but those folks certainly stand out to me. And it is it's a calmness. even in those fireside chats, it's like a listening and really answering the questions that are being asked, like having that kind of engagement. being thoughtful. Jay Sullivan: It's a certain self possession. Kristen Sweeney: Yeah. Absolutely. Jay Sullivan: And actually, since you're on that, if I can throw in one idea for your listeners. Kristen Sweeney: Please. Jay Sullivan: So a lot of people will say that they are well while most of us are loath to admit a weakness. A lot of people are. I'm fine with it, but a lot of people are loath to do that. One that people are always very comfortable saying is, I hate public speaking. I'm not comfortable with public speaking. And so they will immediately put that. I think people do that as a preemptive to make people not ask them to get up in front of the room and talk. But a couple things for your audience to consider your listeners to consider. Number one, except for singing in the shower, it's all public speaking. There's always somebody there. Unless you're talking the other alternative Kristen Sweeney: Ha ha ha. Jay Sullivan: is you're talking to yourself. So if you're speaking to another human being, that's public speaking. But the second is I think the reason that most people are nervous about public speaking is they get on the stage or they're sitting at the head of the table and they're thinking, my gosh, everybody's looking at me. They're looking at me, and we become very self-conscious. So one way to dispel that is anytime you're saying, my gosh, they're all looking at me, recognize no one came to the meeting to look at you. They are all looking through you to get something of value for them. They assume they are listening to you because you're going to be the conduit of valuable information for them. Again, they're self-focused, just like we all are. So if you say to yourself, nobody's looking at me, they're looking through me for something of value to them, and I have this content that I really do believe in and will be helpful to them, and I want to be helpful to someone else, then how dare we not? get in front of the room and share that value that we have. So Kristen Sweeney: Yeah. Yeah. Jay Sullivan: get away from that thought of they're looking at me, make it they're looking through me and think about what is the value I bring to this conversation. Kristen Sweeney: Yeah, thank you for that. That's awesome. That's a really excellent reframe. before we get to the one big idea, I wanna take a brief detour, personal Jay Sullivan: Yeah. Kristen Sweeney: detour, something that wasn't in your bio. you are a Tony Award-winning Broadway producer. I'd love to hear and have you share with our audience a little bit about this experience, obviously as a musical theater performer. close to my heart. So I was so delighted to hear and have the chance to talk with you about this a little bit. Jay Sullivan: Yeah. And I'm not sure how recently we spoke, because we spoke a while ago, but we just won our second. So we won a Tony and and this is all came out of nowhere in a way. A friend of ours in who segued into retirement said in retirement he puts together teams of people who invest in Broadway shows. And I said to him, Kevin, I I don't know anything about this area, but if what you're looking for is somebody who has interest in learning, because that's really what it is, it's an interest in Learning about something Kristen Sweeney: Uh-huh. Jay Sullivan: new. Then Mary and I would be glad to talk about that. And he sent us an email the next day, and the email said, Don't do this, it's a bad investment, you'll lose your money, you'll hate me, we'll damage our friendship. I don't want you to do this, don't do this. But here are nine shows that you might want to think about investing in. Kristen Sweeney: Ha ha ha ha. Jay Sullivan: And so our first year we invested in Cabaret and The Outsiders. And Cabaret did fine, but closed not too long after it opened, and The Outsiders won a Tony. And what was fascinating was watching the energy and enthusiasm among people in the theater and how they bring every ounce of energy to every day's work. If most people had to bring that level of performance energy. That'd be really hard for a lot of people. Th there are days that all of us sort of phone it in. You can't phone it in when you're on stage and all these people are up there. And in those cases, they are looking at you. But they're looking at you to get something of value to them, which is again to understand whatever story you're telling. Kristen Sweeney: Yes. Jay Sullivan: And what's what's really impactful about that in in the theater, what I've learned about the theater is, and it's not, it's very similar to, I don't know, do you ever watch cooking show the Bear, the TV show at the restaurant? Kristen Sweeney: Yes, I haven't seen the new season yet, but yes. Jay Sullivan: okay okay okay so or you l listen to these I'll just call them what they are psychotic chefs who are like acting like the whole world exists on this plate they're putting out there but then you realize that that's very similar to being an actor on the stage because you could if you're an actor on the stage you could have a thousand amazing performances but in performance a thousand and one if you phone it in That was 100% of that audience's experience of that event. And the same is true for every restaurant tour. Every plate put in front of somebody, and if I'm at a really nice restaurant, I don't care if you've got a five-star Michelin rating or whatever. My meal is important to me. And if my meal it isn't amazing, that's a hundred percent of my experience there. And the same is true like at Exec|Comm we go and deliver a This is the hundredth time we've taught presentation skills in the last six months. This is this person's only opportunity to get a learning and development opportunity and grow. And they need it to be great. And so that level of commitment to the audience's experience is something that really resonates for me. Kristen Sweeney: I love that. I love that. can you tell us more about the second Tony? Jay Sullivan: sure. we invested in it's at Lincoln Center. It's got two more weeks. I'm sure it'll be closed before this comes out, but then it's going on tour ragtime, which is an amazing story, Kristen Sweeney: Wonderful. Jay Sullivan: so powerful and so relevant to right now. It's about immigration, race relations, gender relations. it's just an amazing show. Kristen Sweeney: I was in a production of Ragtime up in Boston years ago. And so yeah, love the show. It's just really such a masterpiece, it's so epic and yeah, great. Awesome. Jay Sullivan: Yep. And very well done. So that that was fun. Yeah. Kristen Sweeney: I'm curious, it sounds like there was, you know, a bit of serendipity involved. but I am curious if you see any connection. You know, what stuck out to me was this idea of like Everything I read about is, you know, investment in technology right now. and here you are choosing to invest in something very human in the arts. is there any intentionality in that or anything that like upon further reflection you kind of see as maybe even subconsciously like a thoughtful choice? Jay Sullivan: Sure. I would suggest it was tied in many ways to the way most of us make decisions. That if Kevin, my friend who was over for dinner, who shared with us that he was doing these things, if he had just invented some new tech product and was looking for backing on it, because I trust Kevin, I would have said, Well, Kevin, tell me more about this. I want to learn about this. And he happened to be talking about Broadway shows, not technology. what where I think most of us make our decisions, and this goes to a lot, we teach a lot of critical thinking now at Exec|Comm. And what where this goes to with critical thinking is some people have what we call the halo effect. There's something about them that we've worked with them, we trust them, we know them, we just have infinite trust really is what it comes down to. That word trust can't be said enough. That is what drives our decisions most of the time. That connection to somebody else, that sense of, I don't know much about this, but I'm willing to take a chance because I trust Jack or Susan, whoever it is I'm talking to, the person who's close to me, who seems to make rational decisions, is thoughtful, is doing something really well. Now, if he was selling and he has offered shows, then I'm thinking, I don't like that kind of show. I I wouldn't go to it, so I'm not interested in investing in it. And by the Kristen Sweeney: Sure. Jay Sullivan: way, in Broadway and in theater, the options are endless, like of the types of shows people try to put on. But those shows take can take ten years to go from an idea to getting into a theater. But I think what it comes down to is the serendipity of that's what he happened to share with me. If he had said, I've got this new tech product, I may have gone that route. Kristen Sweeney: Yeah. Yeah. I love that. The trust as really the the anchor there. Jay Sullivan: I you know, I tell all of the, particularly if I'm I'm working with new lawyers or new accountants or new consultants, I'll say, you may think you're in the legal industry, but you're not. You're in the relationship business. We are all in the relationship business. And you've got to have those relationships and make sure that you're creating those relationships for yourself in order to be successful professionally. Nobody succeeds on their own. Kristen Sweeney: Jay, you seeded a little bit for us, the one big idea. So I want to make sure we have time to talk through that now. This is our segment where we get into the nitty gritty of one insight, experience, or aspect of your work that's had an impact on how you communicate. So today's one big idea that we discussed is the need for critical thinking in the AI era. you shared that, you know, we'll get into this more. This is something you're doing more and more at Exec|Comm. Can you talk a little bit about what you're seeing and what the sort of new ish problem is? the concern that companies have right now around critical thinking. Jay Sullivan: We are getting more thanks for asking that. We are getting more and more requests for our courses on critical thinking. And as a matter of fact, we just had a a session for learning and development professionals at our office on critical thinking in the age of AI. And you can't have a conversation these days without mentioning AI. It's comes into everything that we're doing. And that's fine. it's the new thing and it's not gonna go away anytime soon. You know, it's like the internet. I hear that's gonna be big. You know, it's like it's just ubiquitous in everything that we do, right? and AI will be the same way. With regard to AI, one of the challenges I have with it, and being a little more old school, is some of the younger people that I interact with say, it's okay, I'm gonna default to start with AI because that does a lot of the little decisions, because I really think about the big decisions, which is always a funny thing to hear from a 22-year-old. I think that you're like what big decision, but they went to it. And what they seem to miss is that the way you learn to make the big decisions is after you make thousands of little decisions. And so if you're defaulting to AI to do your thinking for you, that's a problem. Because it's only going to pull the information that it thinks is relevant and it will not understand all the nuance to the human experience that go into our decision making. So AI can write a great memo for you, but I always distinguish between artificial intelligence and genuine wisdom. AI can write the memo for you, but it takes the human wisdom to say, should I send that memo? Or should I hold off? Or should I change Kristen Sweeney: Yeah. Jay Sullivan: the tone? Or I I know that's how I'm thinking and it's what AI put in the memo, but do I really want to say that? Because I know the impact it's going to have on somebody. I know somebody's trigger word, and it's in this because AI wrote it. So the other factors, and again, this is not criticism, it's just human nature. We're all lazy. Like most of us will take the easy path over the hard path nine times out of ten. Exactly, exactly. And we should Kristen Sweeney: Is that's your brain trying to conserve calories, right? It's like very survival instinct, yeah. Jay Sullivan: be. Why not do things the easy way? Absolutely. But when you default to letting something else write the minutes of the meeting, whoever had to do that before AI did, Even though nobody wanted the job of taking the minutes or sending them out. Like that's just thankless. But that person actually had an advantage to everybody else who'd been in the meeting. Because everybody else finished the meeting and went immediately to their next meeting. The person went to do the minutes had to think through it and say, does this accurately capture what we've said? And then they sent those out. And so they spent more time thinking about the issue. And that's what we have to spend more time doing. So here's one way to think about it. We also all make snap decisions. And then we're all stubborn. That's so that's nothing. So I'm really cheery here, right? It's all about we're all self-focused, we're all like Kristen Sweeney: Ha ha Jay Sullivan: selfish, lazy, like that. No, it's just human nature. But when you look at a situation and we get very stubborn, The minute we say, and this goes to a lot of critical thinking issues, the minute we say to an idea, so Bill at the meeting throws out an idea. The minute in my head I say, no, no, no, no, no, no. And I might be saying it because it's Bill and I think he's an idiot, or because he rarely has good ideas, or I just I like Bill, but that's not a good idea. The minute we say to ourselves, no, not doing it, we dig in and we go very, very quickly from no to hell no. Like we are adamant now we are not going down that path. So one of big things you can do is go from what I call going from no to whoa. Okay? So that idea of pulling back the reins on the horse. If you every time you hear yourself say no, just immediately go, whoa, let me give it a minute. Let me reflect on it. Just because it's coming from Bill, I'm not going to knock it. I'm going to listen to it. I'm going to figure out what there. I may at the end of after thinking it through still say, no, that's a bad idea. But I might also say, not what Bill said, but just a little tweak, like taking it from here to maybe here, I could still use Bill's idea. I remained open to it. So a big part of critical thinking is not to put the the blinders on. And immediately trust our own judgment of saying no, that's a bad idea, and then digging in our heels. So go from no to whoa biggest things you can do and by woe I mean W H O A, like the whoa, slow it down. Kristen Sweeney: Yeah. Yeah. Yeah. Jay Sullivan: go from no to whoa, and that slowing down of our decision-making process can be invaluable for us. Kristen Sweeney: I think you're getting at something that, and you mentioned it in a couple different ways that's so important, which is, you know, we talk so much about speed as relates to AI, and how can we be more efficient and how can we be faster? our brains, though, time is part of the crucible of how we think and understand. Like we need actual time to process. you know, I even think about things like nervous system regulation, right? Everyone's stressed, everyone's overwhelmed. And then you're kind of like, what shortcut can I flip to right now to calm down? And it's like actually like sit quietly for longer than you're comfortable doing. Time is not you know, we tend to view it as such like a finite resource and can feel scarce for many of us but It is not something that you can sort of engineer out if you're gonna actually interact with something it with your own thinking. Yeah. Jay Sullivan: And Nor should you. Yeah, nor should you. So yes, there is the I just did a column for I sorry I wrote for Forbes for eight years, now I write for Inc. magazine. the last one I just did is about how to slow down. One of the ideas is going from no to whoa so I slowed down that decision making. The Kristen Sweeney: Right, right. Jay Sullivan: other is when you start a meeting with somebody, particularly a client, I get in the call and I say, client, thank you very much for meeting with me to go over the latest draft of the document. Let's get into the document. That's efficient. It also misses a huge opportunity. What I should be doing instead is saying, thanks for meeting with me to talk about the document. Before we get into that, What else matters to you today? And just taking that pause so that it's not a transaction of the document. What you're really saying to your client is, if you say to the document, thanks for meeting with me to talk about X, let's talk about X, you're telling the client, I am small and narrow and in a silo. But if you start by saying, thanks for meeting with me to talk about X, before we get into that, what else is going on with you that would be helpful to discuss? What you say to the person is, I'm not here for a transaction. You just have a smart person on the other end of the call. how can I be a resource for you? And that ability to slow down that meeting, and most of the time your client will just say, No, no, no, let's get it done. Let's get it done. Great. But every once in a while they're gonna say, you know, since you asked, I'd love your thoughts on this. And that changes our relationship with the person. And it changes the way we add value. And again, it goes back to it changes our impact. So I can be really smart, but if I kept the conversation limited to this little silo thing, I never opened up these other opportunities. Kristen Sweeney: Yeah. Jay Sullivan: Yeah. Kristen Sweeney: One of the things I've come to recognize as the sign of a client relationship going well and that it's really strong is that we talk about things that are very general to the business, high level. Sometimes I am surprised by the things that are disclosed to me. Sometimes it's things that they would not tell their team members that are still like evolving in the end. You know, while certainly I like feeling like in the inner circle on that, it it also is one, it actually makes all of the content work we do better because it's informed by this backdrop of what's really happening. So I'm huge on context. It's extremely valuable for the work, but again, it's also a sign that there's a lot of strength in the relationship that it is more than that transactional piece. And I don't think like a younger me would have thought of it in that way. I would have thought of those things as very separate. Jay Sullivan: Right. I think the best line any consultant or business professional can hear from a client is when the client calls and says, I'm not sure you did this, but do you know anything about X which tells you that the client no longer views you in this very narrow way, they've said, you know what, let me call Susan. She's smart. she might have an idea on Kristen Sweeney: Yeah. Jay Sullivan: this. Even if they're thinking this isn't her role or this isn't her expertise, but every time a client says to you, I'm not sure if you'd do this, but and then they ask about something, that's a huge sign of success for any professional. Kristen Sweeney: Yeah. The best Jay Sullivan: Yeah. Kristen Sweeney: person I've ever seen do this was the estate planning attorney, where I got my start. He hooked me up with some of my very first like ghostwriting clients, ghostwriting columns for physicians. He was doing people's estate plans and they would come in and ask him about anything. And he was just like, I will introduce you here. I will introduce you there. And for someone who, I mean, normally that stuff for people is so like. I do it. then I don't think about it. For him to be so central in their lives was really I just still think about that as such an accomplishment. Jay Sullivan: Yeah. He created the relationship. It wasn't transactional. And he was focused Kristen Sweeney: Absolutely. Jay Sullivan: on them. Kristen Sweeney: so let's spend just another minute or so, a couple minutes on a little bit more on critical thinking. How are you helping companies and team members engage more deeply, intentionally, choose to think critically, improve those skills alongside the reality of that LLM sitting right there, just waiting for you to pop off a question? Jay Sullivan: Right. The ability to keep your own voice in the conversation is really And I think you know like AI is moving so crazy fast. in the new version of Simply said, I even mentioned at the beginning of the writing section that AI has great tools, you should use them, you should help them where it's gonna save you time organizing different ideas, great, please use AI. I'm not a ludite, I believe in technology. I think that people should leverage AI to the extent they can. They shouldn't abdicate the responsibility for making the decisions in it. So you want to keep that as part of your process. And the ability to use AI and think critically means how do I use AI and when do I use AI? And if I do the first draft and then I have AI check it, that is much better than if I have AI do the first draft and then I check it. Because we're lazy, so what we're gonna do is AI is gonna say this and I'm gonna miss that there were two or three other things I would have included in that Kristen Sweeney: Yeah. Jay Sullivan: or reformed it and or use better language. And like absolutely have AI check your work. I think that's great. just don't make it the default that you go to. And there are two books that might be helpful to your readers to think about as well. And I'm sure one of them they might know well, the other may not. one is Thinking Fast and Slow by Daniel Coneman, very well-known business book. He won the Nobel Prize for Behavioral Economics. Really teaches us about the two elements of our brain, one that makes quick decisions and one that requires more thoughtful analysis and how those two things interact with each other. And so we use a lot of the concepts from that book, things like anchoring and hurting and the halo effect and confirmation bias to teach people where these things arise at work. And none of those things are problems. They're only problems if you don't realize you're doing them or that you're being sucked into them. So if somebody anchors the conversation by setting out a certain number that is what we're going to talk about in terms of the sales or in terms of the number of people I need, somebody anchors a conversation there. That's okay if there's some thought behind it. But if I just let it go and I don't recognize that's what's happening, I miss an opportunity. So one is that. The other book is a book called The Elephant in the Brain, and really well done. And it's about why we're thinking we're coming up with the decisions we come up with are not the real reasons we're doing it. That there's always something else involved. So there are three questions that you always want to ask yourself when you're really in a tough situation with work and things that you're struggling on something. The first is how much is my ego involved here? And ego is always involved in everything, but how much is the ego driving my decision. So I'm in a meeting with six other people, I throw out my idea, they throw out their idea. I listen to them and some of those ideas, I'm saying those are yeah, those are better than my idea. I get that. But I keep pushing my idea because I want my idea to win, right? That's ego. The second one, so have to ask yourself, how much is my ego getting in the way? The second is how much is my self-interest getting in the way? So I push my idea, two other people push other ideas. I actually, now that I think about it, do better under Jack's idea. So now I start advocating for Jack's idea, not because I think it's the best idea, but because it's best for me. And that's problematic. And the third question is, and this is the tough one to ask ourselves, is how much am I part of the problem? And to every once in a while back up and say, am I making this stuff more difficult? And should I just pull back a little bit? Should I change my behavior? Should I try interacting with somebody differently? Or ask them how can I do this better? And asking yourself, am I part of the problem here? it's a really tough question, but it's a really important one to get us to pull back and think more critically. Kristen Sweeney: I love those. Those are great questions. Thank you for those recommendations. they're certainly going on my list. So really appreciate this conversation on critical thinking. Jay, definitely appreciate, and you know, we heard this in your bio, like the really practical examples. As you talked about those small decisions, I was thinking about I just really believe that in the weeds is where all the big strategy, all the big vision is executed and where you really learn. so I appreciate all of the nuggets that you have shared with our audience. Before we go, I want to wrap with our lightning round section. This is the last word. Every Jay Sullivan: Okay. Kristen Sweeney: guest gets the same five questions to answer. So you could just go with your gut on these. Are you ready? All right. Jay Sullivan: Okay, yep. Kristen Sweeney: Question one: What is your favorite word to say out loud? That's nice. Question two. What's a word you know from reading, but you are not quite sure how to pronounce it? Jay Sullivan: not sure but I'll I'll throw you a curveball on that one instead. I Kristen Sweeney: Okay. Yeah. Jay Sullivan: listen to a lot of podcasts and it takes me forever to get through them because I'm constantly stopping and saying, I don't know what that word means. And I leave the podcast, I go look it up, I come back and then I keep listening to the podcast. So I'm sure there are lots of I thought about it like that I don't know how to pronounce but I'm more focused on the ones that I don't know what they mean and looking up. Kristen Sweeney: All right. Yeah, I love that. what's a phrase saying you wish could be retired for good? Jay Sullivan: I'm out of pocket for the next few days. And I'll tell you why. So out of pocket, people use now to mean they are unavailable. Out of pocket means you paid for something yourself. It like came out of my own pocket. That's what out-of-pocket means. And every time somebody says, I'm out of pocket for the next few days, I'm like, that doesn't mean that. What you want to be saying Kristen Sweeney: Interesting. Jay Sullivan: is I'm unavailable for the next few days. there are a lot of those phrases nowadays that people are misusing. Kristen Sweeney: Yeah Jay Sullivan: And part of this is the the English teacher and the grammar teacher in me. I'm Kristen Sweeney: Yeah. Jay Sullivan: just like, that does not mean what you think it means, and it doesn't make any sense that way. So Kristen Sweeney: thought it was like related to pool like a pot like pocket yes yes Jay Sullivan: No, out of pocket means I had to reach into my own pocket, the company didn't pay for it, I am out of pocket this amount of money. Or I had to like I didn't get the value I thought. I am now out of pocket this amount of money. And Kristen Sweeney: I see, I see. That yeah, 'cause you'll be on your own. Yeah, yeah, yeah. Yeah. Jay Sullivan: and people are using it to mean that they're unavailable. Just say I'm unavailable. So I'm out Kristen Sweeney: Out of office. Jay Sullivan: of office, exactly. Kristen Sweeney: Question four, what's a communication practice or principle that's non negotiable for you? Jay Sullivan: Please and thank you, and apologies when you do something wrong. I'm not I'm not somebody who believes in going around the world going, may a couple, may a couple, everything's my fault at that. But when you do something wrong, say you're sorry and move on. But if you don't say you're sorry and acknowledge that the mistakes were made, the person you're talking to has no appreciation for the fact that you actually understood that what you did was wrong. And so that simple, I'm sorry. clears up a whole lot of stuff and lets a lot of people let go of whatever's their bugger boo is. And then obviously Kristen Sweeney: Yeah. Jay Sullivan: pleases and thank yous are necessary all the time. Especially in email. Especially in email. Especially in email. Kristen Sweeney: Yeah, as I as I tell my girls. okay, okay. Jay Sullivan: Yep. Email can come across as very abrupt and transactional with people. So extra pleases and thank yous there are needed. Kristen Sweeney: Like it. What's the last thing you read, heard, or watched that really stuck with you? Jay Sullivan: I just finished a book, so my wife and daughters have an ongoing race to do 50 books a year, and now they're up to 60 books a year, which I don't never come close to. Yeah, Kristen Sweeney: Holy moly. Jay Sullivan: one year I asked her, I said, Well, I wrote a book this year, how much credit do I get for that? She said, I'll give you three books. I'm like, wow, okay. but one I really enjoyed recently, and I listen to a lot of fiction and nonfiction, is the story of CO2 is the story of everything. And it's about carbon dioxide and how our world is built on carbon dioxide. And a lot of our global climate change issues are happening because of it, but also how the world works. And it was a fascinating book. So it's called The Story of CO2 is the story of everything. Kristen Sweeney: I have not heard of that. Thank you. That's a great recommendation. Jay Sullivan: It's a no, it is it's not on the top I don't know well, I I may have gotten it like the New York Times best books list, but Kristen Sweeney: Yeah, yeah. Jay Sullivan: and by the way, I listen to a lot of I don't read And in our family, if you didn't read it, you listen to it, you can't say when I read that. People are like, No, you listen to there's a lot of shaming going on for listening to books, but I listened to it. Kristen Sweeney: Okay, okay. you get half credit or do you get full credit? Jay Sullivan: no, you got the concepts, but you can't say you read it. Like you didn't put in that effort, so tough family. Kristen Sweeney: Okay. I can't say you read it. Nice. Jay, thank you so much for being here. really appreciate this conversation. Yeah. Jay Sullivan: Thanks for the opportunity. Kristen Sweeney: If our listeners or viewers want to learn more about you, where can they go to find you? Jay Sullivan: Sure, you can find me on LinkedIn, Jay Sullivan. I post every column when it comes out, I post them right on my LinkedIn page and they're all about leadership and critical thinking and communication skills. So if you want to get those, you can get them online by linking to me on LinkedIn. And they're all on my LinkedIn page. So right. Kristen Sweeney: Awesome. All right. Wonderful. And we'll keep an eye the book should be out or just recently out by the time this episode airs. So we're yeah, Jay Sullivan: In October. Yeah. Great. Kristen Sweeney: excited and congratulations on that again. Jay Sullivan: Thanks, Kristen. Pleasure talking with you. Have a great day. Kristen Sweeney: Likewise.