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James Taylor and Howard Teibel on AI, Creativity, and the Future of Work

In 1997, Garry Kasparov lost a chess match to IBM’s Deep Blue. The easy story was that the machine had won and the human had lost. The age of human superiority in chess was over.

Kasparov saw something different and asked a more useful question: What if the future of chess was not human versus machine, but human plus machine?

He called it advanced chess, or centaur chess. And when skilled amateurs using ordinary computers began outperforming both grandmasters alone and machines alone, a new possibility appeared. The strongest player was not the human. It was not the computer. It was the quality of the partnership between them.

That is the question now facing higher education.

AI is no longer a distant technology conversation. It is entering the daily work of institutions — finance, enrollment, advising, research, communications, planning, operations, and student support. The question is not whether AI will matter. It already does.

The leadership question is different:

  • How do we use these tools without surrendering judgment?
  • How do we increase capacity without weakening trust?
  • How do we move faster without losing the human connection?

This week on Navigating Change, Howard Teibel sits down with James Taylor — global keynote speaker, former music industry executive, and one of the leading voices on creativity and artificial intelligence — at the WACUBO Annual Meeting in Las Vegas.

James works with leaders around the world on what AI means for creativity, work, and organizational life. In our conversation, he offers a useful reframing for higher education business officers and institutional leaders: the future of leadership is not simply management. It is orchestration, openness, and curiosity.

At a time when institutions are under pressure to do more with less, James reminds us that technology alone will not create the future. Leaders will.

But only if they learn how to create stronger partnerships between people, tools, judgment, and purpose.

Links & Resources

  • James Taylor’s official site
  • WACUBO (Western Association of College and University Business Officers)
  • Teibel Education Programs
James Taylor:
If you look back at any great ancient civilization, it was always felt that we were vessels for ideas and inspiration. They flowed through us. Now, depending on your belief system, it could come from a higher power, it could come from the people around us, our tribes, our communities that we’re part of. In fact, even places have their own creative genius. The Romans called it the genius loci. And I think colleges and universities at their best have a genius loci about them.

The role of many of the leaders in this room is going to have to change. It’s going to move from where they’re managing other people — you know, they may be managing 10, 20, 50, 100 people — to where they’re going to be now managing both humans and AI agents that will in turn manage other AI agents.

You can create a digital twin of your boss. Let’s say I’m going in to pitch for additional resources with that boss. I can say, okay, here’s my draft presentation, my draft pitch. Imagine you are that boss, critique it. What are the questions he or she is going to ask me? Where are they going to challenge me on different things? It means that when you go into that meeting, the conversation you’re able to have, if you can work that into it, is at a much higher level.


Howard Teibel:
Thank you, Pete. James, it’s great to be with you in person here at WACUBO.

James Taylor:
Well, it’s lovely being here. Always wonderful being in Las Vegas as well.

Howard Teibel:
You’re talking about AI. Your work is in that space. You and I had a brief conversation yesterday, so I found some of your writing. I went on ChatGPT and I did a psychometric on you. James Taylor comes from a high openness, future-focused, conceptually agile, emotionally assuring, innovation-oriented communicator. His talk is designed to help leaders move from uncertainty to agency by reframing AI as a partner in creativity rather than a replacement for human judgment. For a WACUBO audience, the most relevant psychometric theme is Taylor’s work invites business officers to shift from operational expertise alone to creative orchestration. How close is that?

James Taylor:
I think that was very close. And the word that was striking out to me there was openness. In my work around creativity, it’s one of the main traits you tend to see in people that are very creative in their work — this sense of openness, the willingness to question, to learn, to unlearn, and relearn.

Howard Teibel:
So let’s step back. Tell us a little bit how you got to where you are today.

James Taylor:
So I started in a very different industry. I started in the music industry. I used to manage rock stars. That was my old job.

Howard Teibel:
Anyone we may know?

James Taylor:
Yeah, so I worked with members of the Rolling Stones, a lot of Grammy Award winners, in all different styles — jazz, pop, opera, classical. And then in about 2010, I got this request to move to Silicon Valley to work in tech. At that point, I don’t know if you remember, things like Spotify were just starting at that time, but the music industry was in a funny place. So I thought, let’s just change things up. I moved to California with my wife, and I got heavily, deeply involved in tech and artificial intelligence.

Then I was speaking at an event one day in San Francisco and someone came up to me and said, you realize you can do this for a living. You can speak for a living. Really? How does that work? So today I deliver between 50 to 100 keynotes a year, 25-plus countries, for many of the global Fortune 500 companies. This is what I do, and primarily I speak on creativity, innovation, and artificial intelligence.

Howard Teibel:
I’m sure there are some consistent themes that you share wherever you go, because this is a phenomenon that no matter what industry you’re in, this is relevant. The work we do is primarily with education institutions that are now looking at this, and they’ve got in some cases this FOMO, like, should we be doing this? Talk a little bit about some core themes that you really think people should be thinking about, that you talk about wherever you go.

James Taylor:
Well, one of the things I’ll be talking about here — and this is not just me saying this, it’s based upon research by Boston Consulting Group and lots of other organizations — is if you look at why most organizations fail in deploying AI, regardless of industry, only 20% of it is the technology itself: the large language models, the tools that they’re using. Eighty percent of the reason these initiatives fail is because of people, processes, playbooks, things that are running in their heads.

So what I’m going to be speaking about here at WACUBO is, yes, I’ll be talking about the technology and all the amazing things that are going on, and just taking people a little bit into the future, also what organizations are doing just now that are really working on the edges of using AI. But also to bring it back to the cultural piece and to the human side. And that’s where I tend to find that my message resonates with a lot of people, because it blends the human and the technology, the human and machine side.

Howard Teibel:
One of the things, as I was reading some of your writing and thinking, you talk about being an orchestrator. Can you say more about orchestration?

James Taylor:
Yeah. With the period that we’re going into just now — and I have to remind this to audiences because you mentioned that word FOMO — AI’s been around since 1956. The concept has not been new. We had machine learning, deep learning, and then the big change that happened was about 2017, 2018: large language models, things like ChatGPT.

We’re now moving into this period called agentic AI, or AI agents. That is fundamentally different in a number of aspects. One is that these AI agents have much higher levels of autonomy than previous generations of AI. They can have access to other tools, they can use websites, APIs, IoT sensors, and they have much better levels of prioritization and planning.

So the thing I describe — and I’ll be describing this in my talk — is that the role of many of the leaders in this room is going to have to change. It’s going to move from where they’re managing other people, you know, they may be managing 10, 20, 50, 100 people, to where they’re going to be now managing both humans and AI agents that will in turn manage other AI agents.

There are different ways that they can work with this. A report came out about a year ago talking about these two main ways that we’re seeing people work with technologies like AI. One is what we call a cyborg way of working, where an individual is intertwining everything that they do with AI, constantly refining and molding its responses. It’s like if you see a guitarist, that guitar almost becomes part of who they are, it becomes an extension of themselves.

Then the other side is a centaur, and that’s probably more for this audience here. A centaur is this idea that as an individual you look at a project or a piece of work and you’re able to say, these are things that the AI is going to do, and these are things that myself and my human team will reserve and will do. Whether you decide to be a cyborg or a centaur in your work doesn’t really matter. The point is you start to augment.

Where it’s going to move to is this idea that we will become like a classical conductor. You’re conducting this orchestra. Some of them will be humans, some of your team will be AI agents. If you look at a company like McKinsey, for example, they have 25,000 human employees, but they also have 35,000 AI agents now. So for that manager — and this is the good thing — if you’re a good manager of people, studies show that you’re very likely to be a good manager of AI agents as well.

Howard Teibel:
Recently I was in this promo, and the social media person within 10 minutes created this video, this music video of all of us. There’s a place that concerns me about what happens for people who have made a living creatively — photographers, musicians. I love this principle that you’re bringing, which is that this is about augmenting what we do, that we’re orchestrating a bigger conversation. But what do you say to folks who are concerned about this link between their imagination and creativity and the technology? I have concerns about us losing a certain agency in the creative space.

James Taylor:
Yeah, there’s a couple of levels on that one. One is, are the people who created the information that trained the AI being recompensed? Let’s say in music, for example. I can go to a tool like Suno or Udio and say, I want a song in the style of Elvis but singing about this thing here. And it will produce that. Is Elvis’s estate being recompensed by that? Are any of the musicians that the recording sounds a little bit like — are they being recompensed? So there’s that part of it, which goes to the ethics side of AI.

When it comes to what you’re talking about, it’s something that you’re seeing a little bit in medicine and in healthcare just now. The best way you can describe it is it’s like a skill atrophy that’s going on. You see it — one of my clients is Medtronic, who make robotic surgical equipment, and what they’d noticed is some surgeons becoming a little bit overly reliant on some of these tools in some ways, and their own human skills become a little bit atrophied after a while. Once you point that out to people, then they can think, oh, I’ll figure out how to remedy this.

I think the good news, though, more broadly, is it will democratize, let’s say, music creativity — it will democratize music making. I can go and create something, an orchestral piece now, and I’m not a creator in that way. So it definitely democratizes. But there is a big difference between getting something out there into the world — like, oh, that’s good — to being something to being truly world class. That is a different level. That requires a sense of taste, a sense of touch.

Bringing it back to something very physical, if you go to the Lexus factory in Aichi, Japan, they have these people called takumis. A takumi is someone — in America, you have the 10,000-hour rule, someone has done 10,000 hours in their job. A takumi is someone that’s done 40,000 hours in their chosen profession. So these are usually very, very skilled, very experienced people. Even though these cars are being primarily made on production lines by robots, at the end of the production line, you have these people standing there called takumis with white gloves on, and they’re touching and they’re feeling, and they’re spotting errors that the machines cannot spot. They have a sense of taste, a sense of touch.

For us, in the work that we do, we have a sense of gut feel. We have that gut — that doesn’t sound quite right, that doesn’t look quite right. And that’s something you only can really develop with experience.

Howard Teibel:
You said to me yesterday something that I really appreciated about the nature of coming together as human beings — that in some ways there’s going to be an increasing desire to have this face-to-face contact while this technology continues to improve. Say a little bit about what you’re discovering in talking with people about the nature of becoming additionally isolated and being able to sit on our phones and not connecting with each other, and why this is going to be increasingly important.

James Taylor:
Yeah. When Steve Jobs created the iPhone, I genuinely believe — I did an event the other day with Steve Wozniak, who’s the co-founder of Apple — Jobs and Wozniak created these devices as tools of creation, but they’re really now primarily tools of consumption. So we kind of have to think about how we deal with some of these tools.

It’s difficult, because as we use these tools more and more, I think we’re going to have to figure out how we want to use them. It’s going to make us have to reflect on what is the competitive advantage, let’s say, of humans.

So coming back to the in-real-life, the IRL — why I think events like this are so important is because everything can be faked now. We have deepfakes. We see it all the time. Politicians are having deepfakes made of them. I say this also to many people here that work at universities and colleges where you have generations coming in — they are, in some ways, the first generation that they can’t really trust anything.

Coming together — I’ve been having a conversation with a number of events companies recently where they’re seeing a move toward a more festivalization of events, where an event, whether it’s a conference, whatever the event, internal event, is not about delivering content. It’s about bringing people together, bringing a sense of community.

I think about something like this. When we’ve been doing this kind of thing — you could argue for thousands of years. I mean, 2,500 years ago you had something called symposiums. Ancient Greeks — they would sit around, people debate, discuss, challenge ideas. The word symposium just comes from a Greek word which means to drink together, because the Greeks knew a little bit of wine was quite conducive to the creative process. So when people are having some cocktails here in Las Vegas, they’re in symposium.

So many ideas do require proximity. You need a little bit of what we call creative abrasion, where people and things need to rub up against each other. Sometimes that can be — your work, you have difficult conversations. Sometimes you need those difficult conversations for creative things to come out of them. If you don’t have that, then we’ve all probably been in places and organizations where things have been going along okay, fine, but there’s nothing truly creative or innovative coming from that organization.

Howard Teibel:
What you’re saying is so much more relevant for higher ed, because the future professor is one who is able to bring people together to have the right conversations, as opposed to trying to continue to hold on to individuals having all the knowledge. The knowledge is not really living anymore in the individuals, because it’s also changing so fast. So this principle of a festival, this principle of convening people to be in conversations, is a shift away from what we think our value is. Because I think most of us as we get older, we hone in on our expertise. My feeling is it’s so much more about the capacity for how you can engage in guidance.

James Taylor:
Yeah. I think that’s quite a modern notion. We had someone this morning talking in terms of the Native American tribes here. And if you look back at any great ancient civilization, it was always felt that we were vessels for ideas and inspiration. They flowed through us. Now, depending on your belief system, it could come from a higher power, it could come from the people around us, our tribes, our communities that we’re part of. In fact, even places have their own creative genius. The Romans called it the genius loci. And I think colleges and universities at their best have a genius loci about them.

There’s a lot of thought going into this just now. Talking about the individual piece — that really came about in the Renaissance. Giorgio Vasari, the artist, wrote a book called Lives of the Artists. He was the first person to say, you know, Leonardo and Michelangelo as the creative genius. If you look at before that, it was always felt we were creative genius. I think that shift is now moving from recognizing that genius doesn’t just exist within individuals. You have what we call scenius — almost a collection of people, a grouping of people that have their own genius. We call it scenius.

So something like this — and that’s the value of coming to in-person events — is you have a sense of that scenius. You have a sense of people coming together, debating ideas, discussing ideas, and it goes way beyond just the individual. That’s the community.

Howard Teibel:
What’s a practice that you would suggest to leaders to create what I think you talk about as a super creative team — one that blends what I would call human judgment, collaboration, and intelligent machines? What can they do to start moving in that direction to create those kinds of teams?

James Taylor:
Well, here’s a very practical one, and I’m seeing this happen a lot just now within organizations. I was just in Atlanta and I was talking to someone from Siemens, the German engineering company, and what he described to me is something I’m seeing a lot of people do. I think this is very useful for people in this world of business officers and administrators.

It’s something you can do in any of the tools — Copilot, ChatGPT, doesn’t matter. You can create a digital twin of your boss. You just need to feed it a little bit of information about who your boss is, maybe some email correspondence you’ve had, some documents that they’ve written. Like you did right at the start there, it gets a sense of that.

And then let’s say I’m going in to pitch for additional resources with that boss. I can say, okay, here’s my draft presentation, my draft pitch. Imagine you are that boss, critique it. What are the questions he or she is going to ask me? Where are they going to challenge me on different things? It means that when you go into that meeting, the conversation you’re able to have, if you can work that into it, is at a much higher level. This is the bit about the elevation and the augmentation of humans. It’s not necessarily just about replacing those things. It’s about really elevating, because you can get right to the nub of the matter much earlier in the conversation and say, listen, I know this is going to be one of your key concerns about this, so let me tell you how I’ve thought about how you can resolve that.

Howard Teibel:
I’d be a little afraid to figure out what my team would find out about me if I fed a twin. I actually might learn something about myself.

What are you having fun with around this topic? It’s so immersing, it’s changing every day. You’re at the leading edge and thinking about it a certain way. What about this jazz is you?

James Taylor:
Yeah, it’s a fascinating area. It is moving so fast, and one of the joys of what I get to do is, because I speak in so many different countries and so many different industries, I see what’s going on. Maybe I have a little bit of a look into the future, with some organizations a little bit further ahead than other industries.

One of the ones that came out, which I think is a very interesting thing to think about now, is the one-person billion-dollar business. It just happened about two or three months ago — a gentleman, Peter Steinberger, an entrepreneur from Austria. He started a business in October last year, and it was basically building AI agents to be able to build this business. Within the space of four months, he built a business and sold it for an estimated $10 billion. That is a one-person multi-billion-dollar business created in just four months.

There was another one that happened in the New York Times after, which actually wasn’t true entirely what it was — selling GLP-1s. There’s a whole story; I won’t go into the details of that one. But the general trend is this movement of one-person billion-dollar businesses.

The reason I think it’s interesting, more from the work of institutions, organizations, corporations, is you’re not necessarily going to be building a one-person billion-dollar company. But it does make you think, how could I run this organization much more efficiently than I have in the past by using AI agents? This is a thing that’s happening at the moment, and you’re seeing it in quarterly reports by companies. Some companies are just going straight for the lever that says, let’s fire 3,000 people. Other companies are saying no. IKEA, for example, is a good example. They had an opportunity to lay off 8,500 people because they brought in a new AI agent to replace a particular customer service role. Instead, they upskilled and redeployed those people, and they built an entirely new part of the business with those people that generated $1.3 billion last year alone.

Howard Teibel:
You’re recognizing the limitations, but you’re also pointing out how this can really augment and improve our futures. We could talk forever about some of the risks and the downsides. But what you’re doing is offering something to folks to give them some hope that they can engage in this. I’ve discovered — we do an AI, we invite people to do some research on culture — and we still hear people saying, I have never even tried it. There’s still a fear that by engaging in it, somehow they’re going to end up getting closer to feeling like they’re obsolete. So finding a way to do this that is not intimidating — that to me is the key.

James Taylor:
Just get started, play with it. Go into it in a mode of playfulness. I was talking to someone last night, and he said he just went into it. He hadn’t really used any of these tools before. He had one particular thing, he had a big data set, he was trying to figure out what to do with it. Over the course of three days, he said, I got the work back that a PhD student would have struggled to produce at that level of work. A light bulb went on for him. He thought, wow, if I can do this just with a very basic understanding, what can I do if I really lean into it a little bit more? How could this improve my life, the work I do, how can it improve the lives of the people that my work touches?

Howard Teibel:
Thank you so much for bringing this. Really excited about what you’re going to be sharing with us tomorrow.

James Taylor:
It’ll be my great pleasure. Thank you.
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