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Who Leads When AI Thinks? | Adrian Wolfberg, Author & CEO, Organizational Insight Consulting LLC

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In this insightful episode of The Brand Called You, we are joined by Adrian Wolfberg, author of Who Leads When AI Thinks?, founder and CEO of Organizational Insight Consulting LLC, and former U.S. intelligence professional.

Adrian shares defining moments from his leadership journey, explores the evolving role of human judgment in the age of AI, and discusses the leader’s dilemma of balancing machine capabilities with human values.

Discover why framing, judgment, learning, and orchestration will become increasingly important leadership capabilities in an AI-driven future—and why viewing AI merely as a tool is a misconception leaders must overcome.

Adrian also introduces his compelling metaphor of the human–AI dance and explains why hybrid problems require hybrid leadership.

Whether you are an executive, team leader, entrepreneur, or simply interested in the future of work, this episode offers valuable perspectives on leadership, decision-making, and the evolving relationship between humans and AI.

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Who Leads When AI Thinks? | Adrian Wolfberg, Author & CEO, Organizational Insight Consulting LLC

The Brand Called You

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The Brand Called YouWho Leads When AI Thinks? | Adrian Wolfberg, Author & CEO, Organizational Insight Consulting LLC. Machine-transcribed; use the interactive transcript above to jump the player to any line.

Welcome to another episode of the brand called you, what Kastan Patkashore, that brings you leadership lessons, knowledge, experience and wisdom from thousands of successful individuals from around the world. I'm your host Ashwath Oshkar again today. I'm delighted to welcome a senior and a competent professional and author with a deep understanding of AI from Washington DC, USA, Mr. Adrian Wolfberg. Adrian, welcome to the show. Thank you Ashwath. Very nice to be here. Thank you. Adrian is the founder and chief executive officer of organizational insight consulting LLC. He's an author of a book titled Who Leads When AI Thinks. He's a researcher, author, organizational scientist and a former US intelligence professional. So Adrian, before we come to your book, a few questions for you, your career has taken

you from being a naval officer and intelligence professional to becoming an organizational scholar and a consultant. Looking back, what have been the defining moments that shaped your thinking and leadership? Yeah, that's a great question Ash. I look back and I think at my time as a naval officer, I think of a couple of incidents or time periods. I was a mission commander on a seven man jet aircraft that flew off of aircraft carriers tasked with national security missions and that taught me teamwork. As you can imagine, everyone's role is really critical, needs to be integrated. But yet it also taught me the importance of understanding other people's roles and responsibilities. And nurturing their roles as well in order to accomplish the task as a team.

Another defining moment was still while I was a naval officer assigned to the Pentagon. And I participated in the planning and monitoring of a big operation with US personnel who were in harm's way. And during the operation, I noticed an abnormality in the threat environment. It was unexpected and could have surprised personnel involved and caused them to be attacked and physically harmed. So my analysis of the changes of that threat was based on months of pre-operation analysis and preparation of very technical data. Knowing I had this knowledge and this conclusion, I was escorted to a room, a small room in the Pentagon. I had no idea who was in there. And my escort told me, I asked him who was in there. They wouldn't say, they said just communicated in less than a minute and in a non-technical

way. And the room was occupied, it was dark and there was a ledge and there was a man sitting in a chair in the middle. And it was the most senior military officer in the United States military. The chairman of the Joint Chiefs of Staff. So I was standing in front of him maybe three or four feet. And so I communicated successfully what needed to be communicated in less than a minute as my escort had told me. And US personnel, well, the allied personnel in the field were alerted immediately. And the sort I learned from that incident was that information that's communicated with leadership during critical or crisis moments needs to consider the leader's decision space and time. So that, both of those have stayed with me my whole career. Fascinating. Adrian, you created the knowledge lab at the Defense Intelligence Agency to help people

learn how to learn. Why do you believe learning has become one of the most important leadership capabilities today? Yeah, because you know, problems that we face today or anytime that it's been faced, they're never really fully defined and they're not neatly packaged. And when I helped create and lead the knowledge lab, the core idea was that people closest to the work needed the ability and the permission to figure out what was really going on. Yeah. In other words, to be able to describe fully all the factors and the interactions and not just push every medium or hard question upward through the hierarchy for some leader to solve who typically is not focused down to that level of detail. Or focused on more strategic issues, perhaps. Well said.

Yeah, well, I'm going to continue. Yeah, please go ahead. And you know, what oftentimes leaders misses those small tactical problems can have strategic effects if they don't pay attention to them. So that lesson has only become more important in the age of AI. So leaders have access to systems that they can produce answers quickly. But learning helps us question those answers, reframe the problem, adapt as conditions change and helps questions those answers. So in a sense, learning is not just a development activity. It's a leadership discipline and competency for staying capable when the situation and change because reality is always changing. Very interesting. Let's come to your book, Adrian, who leads when AI thinks the title itself is provocative. Who in your opinion should lead and why?

Well, the short answer is that humans must lead. But not because AI is unimportant or because humans always know best. It must lead because leadership involves these very human capabilities that AI does not have. So what are those judgments? The ability to come to a conclusion with uncertain or ambiguous information, responsibility for one's actions, adherence to values in the organization, understanding context, which is really, really a critical important factor that I don't think AI will ever be able to fully understand context and ownership of consequences. So what AI can do is it can analyze, it can generate, predict, recommend it, speeds that we cannot handle.

But it doesn't have the accountability, responsibility for what comes next. So the real question is not whether humans or AI should dominate. The question is who should lead and for what purpose. And in some cases, AI should lead because it can detect patterns, can process volumes of information in very stable situations. But when the problems are required interpretation of meaning, when there's a choice between trade-offs and the decision about action is not clear, that's when human needs to be involved. So that's why the title asks the question who leads when AI thinks. It's not that AI thinks, that's not the problem. The danger is that leaders could stop thinking about how human judgments should remain in the lead. Very interesting.

Edwin, you described the leaders dilemma. What exactly is that dilemma and why is it different from previous technological disruptions? Yeah, that's a really good question. Well the dilemma is that we now have, leaders have access to AI systems and it's becoming ubiquitous now. And it's used to help us think and decide and act faster. That's kind of the motivation for it. But at the same time, these systems also weaken the very judgment that leaders need most. And here I'm talking about critical and creative thinking. So the dilemma is not simply whether to use or not use AI. It's, we will, leaders will use AI. And in many cases, they should. The harder question is how to use AI without allowing those human qualities to drift away to become hidden and to just default to whatever AI says.

And this is different from earlier technologies disruptions because, you know, earlier, any technology was always considered a tool. Here with AI, you cannot consider AI a tool. It's really a relationship that requires a collaborative thought between two minds. This has never happened before. This is the mind of the humans involved, the leader and others in the leadership team. And by leaders, I'm not necessarily meaning those in C-suite positions. I mean, anybody who's in a position where you're a 22 year old or not, of leading people according to vision to accomplish some kind of goal. So this means that this notion of human and machine intelligence or cooperation enters

this space where cognitive dependence cannot be defaulted to machine only produced information. So really what I use the metaphor in the book of dance. And so the leadership dilemma is really about orchestration. You can kind of think about a symphony orchestra. How the leader orchestrates when music comes up and goes and so forth. That's what the leader needs to do and not just delegate. Very interesting. You also emphasize that judgment cannot be delegated. Why do you believe judgment is becoming more valuable precisely because AI is becoming more capable? Yeah, that's kind of a paradox in a sense. That's actually quite true. So it's just because that AI is becoming more capable of producing answers that seem

confident and clear and very quickly. But it's not necessarily that they understand what those mean in a human context. So while AI can produce these answers and identify patterns and generate scenarios or options or even recommend courses of action. But it's the judgment that determines whether the problem has been framed correctly, whether the recommendation, the option fits the context, whether the trade offs matter if they've been considered appropriately according to the context and who must live with the consequences. So the more capable AI becomes, the easier it is for leaders to mistake a fluent answer for a wise one. So that's why judgment can't be delegated. Leaders, they can delegate analysis, data processing and even scenario generation.

But they can't delegate the responsibility for what it means or how it adheres or not to values or the timing of how it fits into a decision space or the analysis of risks and the consequences. So in the age of AI, judgment becomes the leadership capacity and competency that keeps human intelligence connected to purpose, mission and values. I'll say it. One of your central themes is framing. Why do you believe framing is the leader's most important responsibility? Yeah. Of framing determines everything that follows. So framing is deciding what's important, who are the right players, what's their roles, their relationship, what's the interaction, what's the politics involved.

I don't mean political parties, but just agendas. What are the consequences? What are the risks? That's what it's involved. Excuse me. Understanding the entirety of what's going on and the framing then is taking that into consideration to pursue what needs to be done. Next. So if the frame is wrong, even brilliant analysis by humans or AI can move the organization in the wrong direction. So even though AI can produce faster analysis and better patterns and so forth, if leaders have defined the problem too narrowly or off-hiltored, then you're going to move quickly with the wrong understanding. So it's not just a communication skill. It's how leadership connects judgment, context, values, and action, which is actually the topic

of my next book that's coming out, which is called Designing for Adaptability. So the leader's job is to make sure the organization is asking the right question and that's where framing comes in. So that's amazing. As I was flipping through your book, I just loved your metaphor of the human AI dance. Why did you choose dance as the organizing metaphor for the book? Thank you for that question. Well I've been studying and decision making for the last, from a scholarly perspective, the last 20 years and for the previous 20 years in a practitioner role as a naval officer and so forth. And what I've always seen is that the outcome of decisions and the decision process is

never a one time thing. It never just occurs at the time of the initial decision. It has to be so that's kind of where I think there's a big problem with people who are making decisions. They think a better decision, okay, implement, execute, done, move on to the next decision. But it's way more dynamic than that. It's more like a continual cooperation. So that's how the idea of dance came. The dance is kind of a thing in activity where it all depends on the moment, so on the rhythm, on the setting. So sometimes one partner leads and another partner supports and another time the other partner leads and the other supports. So I thought that kind of was a very similar metaphor to what needs to happen here that it's not only a continual process, it's not only roles change, but it's a continual process

that roles may change. You also distinguish between routine problems and what you call hybrid problems. What are hybrid problems and why do they require different approaches from leadership? Yeah, so let me first talk about routine problems. Routine problems are those that are very familiar, a method is well understood. The inputs and outputs are well understood. Success just largely depends on getting the right expertise or the process. You can think about financial audits, manufacturing, line, fast order, cooking established, arrangements. Hybrid problems are on a totally different scale. They combine familiar and unfamiliar elements. They combine technical and human elements and they move as soon as we get involved.

So in a hybrid problem, part of the work may be suitable for AI at some point because AI can analyze the data, look at patterns and so forth. But at another part, human judgment needs to be more involved because the leader has to interpret context, understand competing values, manage uncertainty and decide what action actually fits the situation. So the situation is always moving. So that's the key. I think that's what we often forget. We think, I've done with the situation. Now let's move on to the command and control and the hierarchy and execute. But that doesn't work when the situation moves, which it always does. So they can't just hand off to AI. There's this notion that hybrid problems, therefore, require hybrid leadership. So there's part analysis, part judgment, part learning and constant attention to fit. And so what I mean by fit

is the constant alignment or the constant monitoring to keep an alignment, what the situation is, what decisions should be taken and the action as a result of those decisions. Very interesting. You argue that overusing AI may actually weaken critical and creative thinking. Isn't that a rather controversial position? What evidence convinced you of this? Yeah, it's not actually controversial. It may be not as widely known. But I'm arguing that it's not the use of, it's the overuse and the overdependence. That's the key. And that's where it can weaken thinking, especially when people begin to accept AI answers before they've done the hard questioning, interpreting and reframing for themselves. So what convinced me was what we've seen

in older technologies and what I'm talking about is smartphone usage. So we've seen the research and ask any educator, for example, what's been going on over the last 20 years with smartphone usage. And it's become a matter of overdependence. And what we know from research and just asked anybody who's a parent, that there's the ability to pay attention to clients, that critical and creative thinking declines as questions that are needed to be asked, maybe for school or work, are defaults of the use of search tools to answer them. And that anxiety increases with a higher risk of substance abuse. And there's others as well. With AI, the research for the last few years have already shown, which has mostly been focused on university students and young adults in working environment, that the same thing is happening

with a defaulting of critical and creative thinking to using AI to answer questions. So with AI, this risk moves closer to leadership because when a leader outsources activity to AI when analysis and writing, then we lose judgment like behavior. So the concern I have is not, I'm not anti AI. I'm not pro AI. It's something that we use, but I am pro judgment. AI can absolutely strengthen, it can play a role in helping us when we use it to challenge assumptions and generate alternatives and to test. But if it's used mainly to shortcut

the discomfort of thinking, over time, the people in the organization and the organization may become faster, but they're not going to become wiser. Interesting. It will have time for two more questions. If there's one misconception about AI leadership that you would like every executive to abandon after reading your book, what would it be? Well, I think it's this idea that if you think it's to stop thinking about AI as a tool. In other words, don't ask questions like what platform should we buy? What process should we automate? Where can we gain efficiency? I mean, those questions are important, but they have to come after the leader has asked, what kind of problem are we facing? What kind of judgment is needed? And what are the consequences

that we're willing to own? So AI leadership is not simply technology management. It's a discipline of keeping human judgment, machine capability, and organizational purpose in the right relationship and the right alignment. So the real leadership question is whether the organization knows where and when AI should lead, where and when humans should lead, and how the two should work together under what condition has the problem changes. Amazing. And my last question for you, looking ahead a few years, what leadership skills will become dramatically more important because of AI? Yeah, I mean, this is a good question, Ash. Well, from writing this book to me, these human elements, so human is what I mean by leadership skills,

framing, judgment, learning, and orchestration. So just let me give a quick one sentence for each of those. So framing is important because leaders will need to define, to scope, to articulate the right problem before AI produces answers. Judgment is going to be important because someone still has to weigh meaning, value assessment, risk, timing, and consequences in the context of time and space. Learning isn't going to be always going to be important because the pace of change will make any kind of fixed or established expertise less reliable. There's going to be so much change. Yeah, so you just have to stay on top of

the environment as it changes. And that leads to this last aspect of adapting to the conditions as they changed. And that's kind of where orchestration comes into play because the leaders are going to have to know how to combine human and machine thinking without confusion, without confusing speed as a proxy for understanding. That's going to be a real problem. So leaders who thrive will not be the ones who know the most about the technology itself, but it's the ones who know how to keep people, technology, and purpose aligned as the situation keeps moving. Great response. And on that note, Adrian, I just want to say, what a fascinating conversation this has been with you. Thank you for sharing with me your own journey. But clearly, the amount of understanding you have on AI, which is now ubiquitous. I mean,

everyone seems to be using AI in some form or the other in their life. And it's going to be here to state, just a question of how well we are able to manage. This new tool that's available to all of us. I remember we went through similar kind of exercises when the internet came in in the late 90s. And even before that, when word processing came in in the early 80s. So there are lots of changes that happen. But thank you for talking to me and for giving me your perspective all the way best. Thank you very much, Ash. It's been a pleasure. Thank you for listening to the brand called You, Video Cast and Podcast. A platform that brings you knowledge, experience, and wisdom of hundreds of successful individuals from around the world. Do visit our website www.tbcy.in to watch and listen to the stories of many more individuals. You can also follow us on YouTube, Facebook, Instagram, and Twitter. Just search for the brand called You.

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