Thinking Clearly Under Pressure: Adrian Wolfberg on Decision-Making, Leadership, and AI
Send us Fan Mail Send us Fan Mail In this thought-provoking episode of Living the Dream with Curveball, we welcome Adrian Wolfberg, a former naval flight officer, national security practitioner, researcher, and author. Drawing on four decades of experience and research across national security, sports, health care, law enforcement, and business, Adrian explores how people make decisions under pressure—and why more information doesn’t always lead to better action. Listeners will gain insights ...
Key Takeaways
- Adrian Wolfberg draws on four decades of national security and research experience to explain how people make critical decisions under pressure.
- More information does not necessarily lead to better decision-making, as organizations often drown in knowledge while struggling to take action.
- Experienced and intelligent leaders often struggle when new realities challenge the assumptions and frameworks that previously made them successful.
- Wolfberg's book, Who Leads When AI Thinks?, emphasizes preserving human qualities like critical thinking, empathy, and accountability in an AI-driven world.
- Taking small, incremental baby steps aligned with your passion can help you overcome uncertainty and achieve your long-term dreams.
Send us Fan Mail
In this thought-provoking episode of Living the Dream with Curveball, we welcome Adrian Wolfberg, a former naval flight officer, national security practitioner, researcher, and author. Drawing on four decades of experience and research across national security, sports, health care, law enforcement, and business, Adrian explores how people make decisions under pressure—and why more information doesn’t always lead to better action.
Listeners will gain insights into:
- What leading a seven-person crew on aircraft carrier missions taught Adrian about teamwork, trust, and understanding people’s capabilities
- How a clear, concise explanation helped alert senior military leaders to a potential risk during an overseas operation
- Why experienced people can struggle when new realities challenge the assumptions behind their success
- How organizational culture, psychological safety, and uncertainty can keep people from taking action
- Practical ways to question old assumptions, recognize change, and take small steps toward meaningful goals
Adrian also discusses his book *Who Leads When AI Thinks?*, which examines the human qualities leaders must bring to decisions involving AI, including critical thinking, empathy, and accountability. He shares details about his forthcoming book *Drift*, focused on how our understanding of reality can fall out of step with changing circumstances. For more information, visit www.oic.org, connect with Adrian on LinkedIn, or search for his books on Amazon.
Frequently Asked Questions
Who is Adrian Wolfberg?
Adrian Wolfberg is a former naval flight officer, national security practitioner, researcher, and author who studies leadership, decision-making, and how organizations move from knowledge to action.
What is the premise of Adrian Wolfberg's book 'Who Leads When AI Thinks'?
The book explores how leaders must maintain essential human qualities like critical thinking, empathy, framing, and accountability when integrating artificial intelligence into decision-making processes.
Why do experienced people sometimes fail under pressure?
Experienced individuals often interpret new and novel situations through the outdated mental frames that made them successful in the past, making it difficult to adapt to changing realities.
Welcome to the Living the Dream. If you believe, you can achieve. Welcome to the Living the Dream with Curveball Podcast, a show where I interview guests that teach, motivate, and inspire. Today's guest is Adrian Wolfburg. He is a former naval flight officer who launched missions from carriers in the Middle East, from flight carriers in the Middle East, where the wrong decision can cause lies. Adrian did a lot of research in leadership and decision making across national security, elite sports, healthcare, law enforcement, and business. And Adrian uncovered a powerful truth, and that is that more information does not necessarily lead to better decision makings. So we're going to be discussing thinking clearly when under pressure, overcoming uncertainty, and taking action when life doesn't provide a clear roadmap. So, Adrian, thank you for your service and welcome to the show.
SPEAKER_01Thank you, Kerl Ball. It was a very nice introduction. I look forward to our uh conversation.
SPEAKER_00Well, why don't you start off by telling everybody a little bit about yourself?
SPEAKER_01Okay. Um, well, really for the last uh 40 years, I've been working uh in a practice way in national security. I I started off as a naval officer, as you mentioned, uh flying off aircraft carriers and later worked in the Pentagon and became a civilian intelligence analyst after that. Um and during that time, uh really from the beginning, I was always interested in me as the person who was developing knowledge for uh uh for the protection of for national security. That knowledge would was something that somebody would read and and do something with, either um decide to act or decide not to act. So it was kind of a really uh kind of a unique and uh I guess thinking back on it now, kind of a powerful experience to be in that situation. And of course, I was just on the transmitting side, on the knowledge development and the transmitting side. And I and I got interested in how the receiving side um was part of that part of that equation. And that I got a chance to do when I worked in the Pentagon and elsewhere in DC when I got to interact personally with very senior people like cabinet officers, uh, three and four-star general officers, um, things like people like that. And that got me interested in the whole dynamic of how information and knowledge is created, what the barriers are or what facilitates the the understanding and the acting upon that um in in different kinds of contexts. And I that motivated motivated me to get a PhD in that very subject. And for the last 20 years, while I've still been a practitioner, I also conducted uh research in the various areas that you identified to try to get a um deeper understanding about what really goes on as anybody, no matter what their situation, uh, has to make decisions based on uh incomplete information or ambiguous information and and so forth. Because if I guess I had to put a bumper sticker on what has interested me over my career and what I continue to write about and write books and so forth, it's the journey from uh knowledge creation to action, and that's uh that would that's kind of sums up really the what I'm interested in. Anyway, so that's kind of an overview of of me.
SPEAKER_00Well, I know that you spent years launching off aircraft carriers where lives can be at stake. So talk about what was an experience in your military career that fundamentally changed the way that you make decisions.
SPEAKER_01Well, one thing was um uh in this aircraft carrier operation, I was the mission commander of a seven-person crew, and our job was to find out what adversaries were doing, which of course they were trying to hide what they were doing. But the context was you know very very unique and provided me with a uh kind of a deep understanding of what teamwork is and also what um kind of the beginnings, my awareness of what um kind of knowledge creation was. So just briefly, this this is one example. I'll give you another example. Um so in the aircraft, um there are seven people and they all have different skills, they're all trained differently, they have different uh ages, different seniority, and yet we were all in the same boat, so to speak. Uh it was kind of very dangerous um operations flying on and off aircraft carriers. And as the mission commander, I had to make sure that number one, I had a you know a deep understanding of what everyone's capabilities were and what their limitations were. I also had to develop confidence in what they said they could do and what they actually were able to do. And that by achieving that competence, the more I could achieve that competence, and I was able to eventually do that, the more I could focus 100% on the mission itself. As what I discovered is worrying about one's safety and this kind of dangerous situation then reduces one's attention to focusing on the mission. So that's one story. Um, another story is um I I would I've got a few stories, but I'll just pick one. Um I I had an occasion to um to be involved with the planning of an operation that involved US forces that um both air and and naval uh forces were were exposed to potential harm. And I was involved in the planning of that, and I was also involved, this is while I was in Washington, D.C. for an overseas mission. Um, I was also uh part of the monitoring crew to uh be aware of what actually was going on during the operation. And the um this required months of months of planning, I think it was three or four months. And during the operation, I noticed something something unusual was happening. And I mentioned it to the people who were above me, and they they didn't believe me, they actually laughed at me. Um, this knowledge that I had created, this kind of goes right to this theme you're you're introduced to. You know, there was it wasn't a question of, I don't know, I don't think it was a question of trust. It wasn't that they didn't trust me as a person, but they somehow didn't think that I could come up with this kind of conclusion myself, that it was too complicated, too complex, too sophisticated, something like that. I'm not sure, you know, thinking back what exactly it was. Um, but fortunately somebody on the planning team became aware of this. Um, and I was getting quite frustrated that the knowledge that I had was not being received, um, was not being um ingested. It was received, but it was dismissed. And um, so this person who was uh with me on the planning process said, Okay, come here. I want you to come with me. We're gonna walk to this room and I want you to tell the story that you have to tell. And I said, Okay, well, can you tell, you know, so as we're walking, I I asked, can we can you just tell me, you know, who I'm gonna be talking with? I said, no, I'm not gonna do that, but I will tell you that you need to convey this information in one minute or less, and you cannot assume that this person knows anything about what you're talking about, so you have to uh express it in a way that like your grandmother could understand. Um, so during the walk, I was able to put all that in perspective. I had had previous experience doing the same thing at in other contexts, but this was a very, very different, unique context. So I got into the room and it uh it was a very small room, and uh there was kind of a um a raised uh deck there um on the in the small room, and there was three chairs, and there was one central chair, and there was a man sitting in the central chair, and he was the chairman of the joint chiefs of staff. So this was the most senior military officer in the in the United States, and so I was able to um, so I knew who he was, and I was prepared, and I was able to convey the story in less than a minute so that he uh not only could understand the words that I was using, but he was able to comprehend the implications of what I was talking about. And so I departed and I learned later that he immediately informed the um the forces that were operating overseas of what was going on so that they would be uh not surprised by any adversary behavior. So that is just another example of how you know information itself may not may not land where you want it to land.
SPEAKER_00Well, after spending four decades studying leaders across different industries, talk about the biggest mistake that you see experienced intelligent people make when under pressure.
SPEAKER_01Well, that's something that I've studied, um, other people have studied, but but I've done a lot of that study. And I I don't know if I'd frame it as a mistake. Um, certainly retrospectively, it's it can be considered a mistake, but it's that because we are human, if if we don't have um the preparation and the prior experience with the situation that we're now being exposed to, that we're under pressure, that we're not going to have time to think critically about it or creatively about it, we're only going to be able to draw from our our mind what we've already been able to conceptualize in words and sentences about that past experience, which we think might apply today. And so there's a huge, depending upon um you know how much experience you have and um how much preparation you have, what you actually bring to the table in such pressure um may be very incomplete, maybe and usually is incomplete, and you usually is is off-center and not directly uh going to address at um at a deeper level what's going on. Um so that's you know the part of that mistake is depending upon the the type of pressure, um, you know, how much time you have to react, uh, whether the time it may be not, maybe it not it may not be a time pressure, it could be a an agenda pressure or a personality pressure, but depending on how much time one has to operate in response to the pressure, you know, will determine there'll be a lot of different factors, um, how well you can actually see reality as it's occurring now and um being able to come up with ways to deal with it. This, if it if you need to have a reaction within 10 seconds, you can only do it by by what you've integrated in terms of your past experience and your preparation. If you have a longer time, you know, then you can start asking questions. You can ask questions of people around you for their ideas and so forth.
SPEAKER_00Well, I know you talk about how organizations drown in knowledge but joke on action. So talk about why you feel it is that people know what to do, but they struggle with taking the first step.
SPEAKER_01Well, I think um this comes to the in organizations, this comes to the culture of the organization, um, the uh personalities involved, uh people who are uh supervisors, managers, leaders. And uh there are there are going to be constraints and barriers in typically in organizations. There this could be in form of policy, formal things, policies, rules, regulations, but also you know, informally. There could be trust issues. Um there could be issues where there's not enough um psychological safety to ask questions for clarification. That's a common um need. Uh, and and if there's not that safety um or or whatever like that, then um someone could um go off and address something in in totally the wrong way. Um yeah, so yeah, I think that kind of in a at a summary level talks about it. Um even if the person um knows what to do, they they still have to assess what the right thing to do is. And so if the context, and this could be whether you're talking about making a decision as a family member or in a team or an organization or in society, um, depending on the risks associated with um taking action in in in the face of um constraints and barriers, um, you know, will determine how that individual is going to act. I I hope I've uh sh given some insight into responding to your question, Herbal.
SPEAKER_00Yep, you sure did. So you often see smart people fail and people that aren't aren't so successful succeed. So just talk about um what why you feel that is and and tell us a story if you have one that um you know of that makes a person triumph or successful in a difficult situation.
SPEAKER_01Yeah, so you asked two questions. I mean, you asked a question about people uh who are successful and don't succeed, and people who are not successful and succeed. Um, of course it all depends on the context. Um, but I'll put speak to the the first one because that's often a topic that um is studied and and we also see that in in organizations. Um there's this you know, people who are who become very successful in what they do really have an exquisite understanding about um the kind of knowledge they need. Um, they have exquisite um uh uh experience, uh you know, preparing for they basically have a handle on everything that's going on um with respect to their world that they're living in. And this is something that is just human nature, it's something that is true with um leaders, but it's also true with say functional experts, um, you know, people who are um just technically or um you know otherwise very knowledgeable about what they what they do and what they know. The the when things fail, um it's usually when something new comes out of the blue or comes comes to face them, um, and they have to figure out whether they don't do this consciously, but they're going to interpret this newness, this novelty from the frame that they've developed over their years of success and expertise. And one of the dangers of being in that situation is that it's very hard for whether it's leaders or or experts, um, to learn something new. And so why do I say that? Well, they have a picture of the way the world works according to what they've done, their say that their their career field or their um their management uh history, their experience. And sometimes it's very hard, it's quite often very hard to get out of that frame to incorporate something new because their frame is what exactly made them successful. And now we're now reality is asking them to sh to make a modification to that frame of looking at the world. Well, that creates a contradiction in their own mind. Now, this is not something that people are consciously thinking about, but here on the one hand, reality has changed, but on the other hand, the thing that is changing is causing them to possibly no longer be successful because it'll be a challenge or a change to what's made them successful. So we often see that in um teaching adult learners in in graduate school who come to learn, but have maybe 10, 20, 30 years of pure expertise, and now all of a sudden they're exposed to uh something that's totally out of their expertise. As far as you know, the second situation where someone who's um not knowledgeable or not expert and does something successful, I don't I haven't really studied that. To me, my my you know initial feeling is that's luck, um, or maybe being in the right place at the right time. But most of the time, what we see around us is people who believe they have expertise, and and often they do, of course, the issue becomes um you know very different if they actually don't have that expertise, but yet they appear to be knowledgeable. And I think a lot of people have witnessed that in in organizations and in society or even in family life, that there's a presentation of knowledge or expertise about the reality that's going on, but the individual or the group uh presents themselves as being confident uh where they really are not. So I'll I'll leave that as there for you to yeah, I'm ready for the next question.
SPEAKER_00Well, many people have dreams that they want to pursue, but are afraid of making the wrong move. So what advice would you give someone who feels stuck because they can't predict the outcome?
SPEAKER_01Yeah, no, that's a really good question, Kerve Ball. Um I think you have to um you know think about what's important to oneself and what gives one satisfaction one joy and what and and what kind of excites oneself and the the what I've always found and this is not just you know what what I'm saying but the there's always uh the journey that it takes to get to that outcome so it's very very hard to predict the outcome in the way that it'll actually materialize i mean this is not only a personal issue it's an organizational issue as well and I think I think things progress with I just call them baby steps or small steps and you build on success and the world is always changing so the path that um you start this journey on this kind of initial step may change as as you go forward so I think the um you know the the thing to keep in mind is to follow the passion um follow follow the interest and let that be your guide as opposed to uh evaluating whether the um outcome is going to be achieved uh from the start well I know you've studied similar decision making problems in national security sports healthcare and business so talk about the warning signs that tell us that our normal way of thinking is no longer working yeah well that that is um something that we would like to have that knowledge but from what from my research and and others we often don't know what the warning signs are until there's some kind of cataclysmic failure and this could be at the organizational level it could be at the relationship level um uh society level um but and I think you know I we all probably have had these kind of experiences where we and I'll just talk about it for my own you know that we think things are going on as expected as normal when it when all of a sudden boom it's not and things fall apart um what what is desirable and what we need to develop ourselves and our organization is to have a a clear idea of what's happening in front of us at the time not just when we made a decision two weeks ago two years ago two two decades ago about how we saw reality then and chose how to move forward and again this could be in a family relationship spousal relationship teamwork a team relationship organizational society the trick is to be able to uncover pull the wool over your eyes so to speak and and um be aware of the conditions that are around us and how they've changed um this is this is not easy to do and and the way that people um you know are able to do this more successfully is to ask questions these questions can be asked of themselves is are the assumptions still operating the way I thought about the way I thought about it back when two weeks ago two months ago etc two years ago um what is it that that is occurring now that could be shaking that um uh assumption uh that I had long ago um uh do I need to um how do I need to think about this um who do I need to talk about perhaps to um you know validate um my my understanding of reality so it's all about um being able to evaluate change that's occurring which is always occurring because we're people and we're interacting in whatever context and sometimes that's difficult to do because we're we're you know working and we're working a thousand miles an hour and if we have family you know our time is occupied and our our ability to pay attention to ourselves to have that self-reflexiveness um that metacognitive ability to think about how we're actually operating in the world um can suffer um this certainly is true in in in the case where we were talking earlier about operating under pressure and um that that it that certainly confounds uh one's ability to understand what's what's going on in the present so the answer is that it's hard for us to do this but to to be able to do um to be able to be more successful in this realm we have to be more reflective we have to manage time differently we in a sense have to think above and beyond time to ensure we've set the priority to um not only not only to see the world as it is but also motivate and model that behavior for others so that especially in an organization they also will do that. Well talk to the listeners about your book you know tell us uh you know about them and what we can expect when we read them and where we can get them okay thanks for that um I I recently published a book um this year called Who Leads When AI Thinks and this is not a technology book at all it's really a uh a user uh or leadership um thinking book about how to approach the technology before it's actually used and it's really about bringing those human qualities to the forefront to be part of the engagement process with AI. And the reason I wrote this book is because so much of the discussion that either is in writing or people talk about is mostly focused on the technology itself, what it can and cannot do, what we hope it can do, what we're afraid it can do and kind of about you know governance issue what we should or shouldn't do about it. And I wasn't seeing anybody talk about how we as humans should um react or engage with AI. And so this is a book that gives um a kind of a bunch of frameworks about how to think about this but it's mainly based on um the following kind of human attributes that we need to preserve because AI cannot take those over it cannot duplicate or replicate these things and those things are how we frame problems. You know framing is is really about figuring out what the reality is and then what we consider that is important in that reality what and what may not be necessarily important. So we've kind of created a box of what we just need to focus on. We also need to we also need to frame things multiple times. So there's this notion of reframing as time moves on as the world changes we need to reframe as well um also you know one thing that um research has been showing recently um not only with um ai but also with smartphone usage which has AI embedded in it now is retaining and um using critical and creative thinking and not um defaulting that or giving it up to AI large language models um like chat GPT and Claude. So in addition to those there's also empathy that's uh required um you know as we move forward um decisions are gonna from now on uh are gonna have some combination of AI and human involvement what that combination is uh will be dependent upon the nature of the problem and the context and that will change of course over time um but there will always be the human making the final decision but now um there will be this AI component in it in it so it's really going to be incumbent I mean it's always been incumbent on leaders before AI but it's become more incumbent on leaders because of the AI contribution that leaders that we uh whoever using AI is uh uh aware of or can appreciate the consequences of our actions to our fellow human beings um and why this is important well because uh to some you know some degree or another could be small could be large there will be an AI contribution and AI is not good at understanding uh human uh reality human context as it's occurring in the present so empathy is going to be really important as well also accountability um will it that's something that we the weak we humans uh must not give up to um AI. We're the final decision maker we're going to be accountable and not AI. So it kind of weaves all these human qualities into an approach for um in engaging with the problem that you're dealing with with figuring out the right mix of um machine and human um intelligence and also kind of the new competencies that are going to be needed for leaders moving forward. Tell us about any upcoming projects that you're working on that let's need to be aware of well I'm just finished a book um that probably in probably mid-27 or so will come out and it comes from my thinking during this uh the book that is just now published um Who Leads When AI Thinks and it it comes about um the this issue about um having to continuously update our understanding about reality or you know what's actually occurring in the context that we're we're living in whatever that is family work or whatever and so this book is about why why we um drift away from our initial understanding that that we formulated whenever we started focusing on an issue or a problem whatever that was two weeks ago two months ago two years ago and why we we drift away and don't um can and and don't adjust our understanding um to what what reality to the way things are today and the book is called drift and and so the the importance of that why did I write that is because um so many of today's problems occur in terms of um outcomes that are disappointing or catastrophic because our understanding of reality has um shifted has drifted has moved away from reality as it's playing out and so the kind of the resources that we've allocated or the decisions that we've made originally are no longer going to be effective as much in in solving the problem. So there may be a lot of activity by individuals and family or organizations or society that seems to show that yeah progress is being made but it's going to be progress towards some reality that occurred in the past and not in the present well that's a that's a recipe for inefficiency ineffectiveness and total disaster and while it's not a book about AI one could imagine that um being more effective in reducing this drift would be beneficial in an era of AI when there's so much pressure to do things in a timely fashion. So that's what I um just finished doing and I have another book um in the planning stages to then go more deeper into how we understand context as it's occurring uh in the as as it occurs according to how it appears to us so the context the you know what's the reality what we figure out should be included into it what we what needs what can be excluded according to the problem or or the issue that we're facing well so people can keep up with everything that you have to though that's your contact info well yeah so um you know I'm searchable in Google and and ai um LinkedIn is uh a very easy way to uh find out about me and get a hold of me I have uh my web my professional website called um organize um organizational insight consulting and uh those are well all ways that people can find out about me and uh the book is available um uh who leads when ai thinks on Amazon um springer is the publisher um it's easy to uh just do google or or Amazon to to find that so your website is organizational insight consulting dot com well yeah insight it's um dot org dot org so organizational insight consulting dot or g or yeah and so it's o ic the short version of is is just o i c um but just with the long version people should be able to find it okay so so we can put in oic dot org and get it yeah I think so yeah I do it it comes to me yeah okay we'll close us out with some final thoughts maybe if that was something I forgot to talk about that you would like to touch on any final thoughts you have for the listeners um well um just that's you know I listened to one of your podcasts uh before I I contacted you and um it was a really interesting one about there's a guy named Tony uh 10 uh tenegle um talking about um kind of how you approach work and and that really resonated and I just wanted to just um you know add to that that I I've I've always done something where I've been excited about doing stuff and if the opportunity or the condition hasn't been there to do that I've always uh found a way to to make it exciting um uh under rare occasions has that not been true but there's always things that need to be done that people have not focused on and not paid attention to and so that's always kept um work as being something exciting and not a a drudgery all right ladies and gentlemen there you have it o-o-i-c dot or g to keep up with everything that Adrian's up to please be sure to check him out on LinkedIn check out his books he has a wealth of knowledge and follow rate review and share this episode to as many people as possible also to keep up with all things living the dream please visit www.curveball337.com if you haven't already done so sign up for the newsletter so you can see every time we release a new episode thank you for listening and supporting the show Adrian once again thank you for your service thank you for all that you do and thank you for joining me thank you curveball it's a it's a pleasure talking with you for more information on living the dream with curveball podcast visit www dot curveball337 dot com until next time keep living the dream
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