James Taylor (00:09)

Welcome to the Super Creativity Podcast where we explore the intersection of technology, humanity and innovation. Today we’re honored to have with us Kate O’Neill, renowned as the tech humanist. Kate is a leading expert in aligning business success with human-centric technology. As the founder and CEO of KO Insights, she has guided organizations like Adobe, Google, Microsoft and the United Nations towards more meaningful and effective digital transformation.

Her latest book, What Matters Next? A Leader’s Guide to Making Human-Friendly Tech Decisions in a World That’s Moving Too Fast, offers a roadmap for leaders to navigate the rapid pace of technological change while keeping humanity at the forefront. So let’s delve and dive into Kate’s insights on making technology work better for business and importantly for people. Kate, welcome to the Super Creativity Podcast.

Kate O’Neill (she/her) (01:04)

Thank you, James. Great to see you.

James Taylor (01:06)

Well nice that we’ve met a few times before now and it’s just wonderful because I know this is your, is this your fourth book I’m guessing? Third, fourth.

Kate O’Neill (she/her) (01:14)

It’s my fourth

book in the business and tech space. I have six overall and I’ve contributed to a few others, but so it’s always kind of a funny question. Like how many are there? Well, it depends on how you count them. But yes, four in the business and tech space.

James Taylor (01:26)

Now, what were you doing before you became known as a tech humanist? Because I’ve always known you as a tech humanist, and that’s the title that you often get, you is used. What were you doing before you were out there giving speeches, writing books, consulting?

Kate O’Neill (she/her) (01:35)

Yeah.

You know, so my career has been in technology for…

30 years now, but it’s been in different fields of technology. in different fields that didn’t have names at the time. before we were calling it information architecture, I was doing information architecture. Before user experience and before customer experience, was doing that content management, content strategy. So all these different fields that are, in some ways, the interesting thing about them is that what they all have in common is that they are this interesting synthesis of understanding language.

and the way humans organize in our brains and the way technology best organizes. And so it’s kind of always bringing those things together. And then over time, realizing that I was always, in every organization, the person who was the sort of fiercest advocate for the customer or the user or the people on the other side of the equation. And that became sort of my go-to role. I just became the person who

who realized like, need to make sure the business is successful, that the business objectives succeed, but we also need to make sure that in doing that, we’re providing for human success as well. And so that became that morphed into this field over the last 15 years of speaking and researching and writing around tech humanism.

James Taylor (03:04)

Well, it’s interesting, you use that, the tech humanist, it’s an interesting phrase because I don’t think of you as a futurist in that way. I think I’ve seen you talk about futurist adjacent, which I thought is quite nice because when I often think of traditional futurists, it’s like intellectual Red Bull. It’s just like a high, a sugar high, and there’s nothing really much there. But you kind of go deeper.

Kate O’Neill (she/her) (03:19)

Yes, yeah.

Yeah.

James Taylor (03:34)

this, tell me about this, the tech, the humanist start, was there a particular point that you decided, because you could have gone and just done the typical futurist thing and gone down that route and break shany thing syndrome, but you chose a slightly different path to face it a little bit more around ethics, around humanity, was there a particular point that you went that this is the direction I want to go with this?

Kate O’Neill (she/her) (03:59)

Yeah, I think like you, I see the whole futurist space.

as one that’s filled with a lot of conjecturing and a lot of posturing that doesn’t really feel like it pays off in many respects. It doesn’t necessarily feel like it benefits business leaders either. You know, the people who most need to consume that content are the people who are trying to make the high stakes decisions and want the most guidance. And what it feels like is much more relevant is what I would think of as more like foresight strategy. And so that’s one of the things that I really lean into in this book is the difference between futures

them in foresight, really trying to use a model where we’re using insights thinking that yields foresight along the way so that we can triangulate our decisions for what we need to do now with what we need to do next. But that came about because I did work around the future space for a good bit of my career. I worked around fields that were very much trying to be on the cutting edge of things. And sometimes it worked and sometimes it didn’t. And the times when it worked, like

You know, I know that in my bio you probably have for For viewers to have seen by now that I was one of the first hundred employees at Netflix It was a really incredible experience But what was for me the most incredible part of it was getting to see the visionary leadership at that company So for example, this is in 99 2000 2001 Netflix is still very much the very tiny company for compared to blockbuster, which is the 800 pound gorilla

in the video rental space in the US and largely internationally. And even at that time, Reed Hastings and the executive leadership team made decisions to invest research and development, money and resources into what we were then calling set-top boxes, which was the predecessor to streaming as we now know it.

And so you, just, it’s so mind blowing to me, the confidence and the vision to be able to say, here we are struggling to actually gain any kind of market share whatsoever. But we’re also going to be doing this research and putting money into what we’re going to be doing if and when we succeed in sort of dethroning the, the king and becoming the dominant player in the space. We know that there’s probably going to be new technologies, new platforms, and we have to be ready for that.

And to me, that’s far more useful than sort of an intellectual exercise in futurism. It’s really trying to think ahead and trying to put your resources where they most will make an impact.

James Taylor (06:37)

Now there’s a lot of, I guess, people kind doing what you do, but internally within an organization. You mentioned your work at Netflix, and there’s a documentary I remember seeing years ago called 16 Feet from Stardom, I think it was called. And it was about the backing singers in Famous, and there was a line, I think it was maybe Bruce Springsteen said, that 16 feet from the back of the stage where you’re the backing singer or the drummer or the bass player to the front of the stage where you are the main person.

Kate O’Neill (she/her) (06:51)

yeah.

James Taylor (07:05)

where the spotlight is on you, that’s quite a distance to go. What gave you the confidence to go from that backstage hero within organizations like Netflix to going onto the front of the stage and to really being that thought leader we know you today?

Kate O’Neill (she/her) (07:21)

think you just called me Darlene Love and I like that. I’ll take it. I’ll take it. No one gets those vocals like she does.

James Taylor (07:25)

We love Darlene. Yeah.

Kate O’Neill (she/her) (07:32)

But I think for me it was just the exposure to good leadership and good decision making like what I saw with Reed Hastings. I saw a number of other instances of good leadership. I also saw some bad leadership and I think you learn even more from a bad example than from a good example. So getting to see some choices being made that I would like to have seen made different. had a kind of a…

life-altering interaction with a CEO I was working with one time who who was frustrated with my Consists constantly trying to guide the decisions on what I how I saw the the market and the field playing out And he sat me down once and he said Kate I know you think you could lead this company better than I do I said no I think you could lead this company better than you’re doing and that’s really where this comes from. It’s not it’s not arrogance I don’t think it’s it’s really the sense that

In my last company, Before KO Insights, which I’ve now run for 11 years, I had an agency before that was an analytics and strategy agency. And we evolved our values through actual work with clients. And one of those values that we came to was speak truth to power, but confront with compassion. And I really feel like that second piece of that,

that idea is an important one because I think people are just doing their best sometimes. They’re really trying to figure out how to solve the problems in front of them and they’re intractable problems and especially today and that’s really what comes into fruition with What Matters Next. I think a lot of leaders are really struggling with how much complexity there is, how much acceleration there is, how much they feel like the field is changing all the time, how much it seems like technology is just constantly in flux.

And there’s a lot of anxiety about, what if I make this investment in this technology and try to, you know, update my customer service function and three to six months from now, there’s an entirely new technology space and we’ve made the wrong investment. And that’s a, that’s a valid concern. It’s one that I have an answer to. And that answer usually is you’re going to be so much better off because you’re not stuck in inertia. Just having some momentum around change actually makes you more agile and you can begin to swap out for whatever you

you

find that the more important latest technology needs to be much more readily than if you were still stuck in your previous implementation in most cases. So I think the compassion though for that situation is what I learned along the way is to be able to really empathize with the fact that these are complex decisions and leaders are in a really difficult role. And I like to find myself in a role where I can actually help.

affect that change in ways that scale, in ways that make pretty significant impacts because it’s downstream from those decisions that most people experience what the company has to offer and what the impacts of those decisions are going to be.

James Taylor (10:27)

Now, one of the things that you do in this book, I know you have a love of language, the use of language. We were speaking earlier, you speak ridiculous number of languages as well. You are definitely beating me on the Duolingo stakes at the moment. One of the things you talk about in this book, which is a useful thing, and I think it’s good someone with an understanding of language really calls us out, is the difference between innovation is that term that we hear all the time gets used.

Kate O’Neill (she/her) (10:33)

Yeah.

Yeah.

Yeah.

James Taylor (10:57)

but you kind of make a definition between transformation versus innovation and how these are not necessarily the same things. We think of digital transformation being used all the time, innovation, and they’re used in the same phrase, same thing often, but you make a distinction about that. can you just talk to about when did that idea come to you? Where did you see that as a problem in a lack of clarity in what people were trying to do?

Kate O’Neill (she/her) (11:04)

Yeah.

Yeah.

Yeah, I think that I was seeing that in the questions and answers and interactions I was having with with executives and business leaders after keynotes, you know, having these sessions where in many of it, and this probably happens for you too, where in many of the conferences I speak at, one of those sort of perks that an organizer might set up is you get a 45 minutes alone with with the VIP attendees and you get to sort of field their questions in a much smaller group. And those kinds of things are just their goal. They’re so

useful. And I think the attendees really enjoy that too. So note to the event planners, that is a really nice feature. But in those kinds of sessions, I would often hear much more candid kinds of questions than I would hear, you know, in a 3000 room audience, 300,000 person audience, because you don’t want to speak up with those those personal questions. But the kind of thing that I was hearing, eventually made me realize that what was happening was that leaders who came up to the CEO role or to executive

leadership roles in a field other than technology, which is most of them. We have only recently begun to see technology executives make their way into the top senior roles in organizations. So most CEOs come from a field other than technology. And the way that they’re thinking about the technology imperatives was conflating what needed to happen in terms of bringing the organization up to current standards with what they needed to do to look ahead and

be ready for the future. And I just found it very useful to make this distinction to say, look, what you’re talking about most of the time when you’re talking about digital transformation, you’re talking about catching up. You’re talking about looking at what the market already expects you to do.

What you’re talking about, what your competitors already do. You’re talking about what there is an sort of existent set of models and technologies that you can use to get to where you need to be. Look at COVID, for example, digital transformation was incredible during COVID, but it was a lot of things that existing companies could already do, like, you know, the mobile ordering and things like that. so retail and fast food and these kinds of services had to quickly implement those kinds of things where lead

in the space already had them, like Starbucks or Dunkin’ Donuts or those kinds of companies were already ahead of the game. So that’s a catch up. But innovation is different. Innovation is looking ahead. Innovation is standing firmly in this moment and looking ahead and saying, again, like the Netflix example, what might the next series of changes be? If we ask the meaningful questions about this moment, what people need, what looks like it’s changing, what kinds of trends are actually sort of changing and evolving the landscape?

around us, where do we probably need to be or where might we likely need to be in 10 years or so? And how do we think about the kind of meaningful and significant changes that we need to make over the next few moves that position us there? And I actually have a few models that help people conceive of that better, and some of them are in the book and some of them are more conceptual consultative models, but…

I think that distinction is one of the clearer, more useful ones in the book and that for a lot of, especially for non-technology CEOs, I hope that’s going to be a really disambiguating, very helpful clarifying type of model that will help them give better headspace to the kind of decisions that they need to make.

James Taylor (14:55)

I guess that’s one of the benefits of bringing someone like you in, whether it’s in consulting or speaking, is there’s that phrase, you can’t, you don’t know what’s inside, you can’t see the label from the inside. There’s something like that, that phrase, that type of phrase where I think with transformation, it seems to be a lot of the time that people within the organization, they kind of know the questions that they should be asking. They might not have a process to think about that, about how you use those.

Kate O’Neill (she/her) (15:07)

Right.

Yeah.

James Taylor (15:23)

but they kind of know because they’re quite close to it and they’re quite close to the customer versus the innovation part where they don’t know what they don’t know, they don’t know the questions that they don’t know. guess bringing someone like you in allows them to ask, help them ask better questions.

Kate O’Neill (she/her) (15:37)

Or you, right? I mean, you find that as well, I would imagine. Don’t you find that transformation and innovation to be conflated ideas that happen so often when the discussions you encounter?

James Taylor (15:47)

Yeah, it’s funny, it often comes back down, I think it comes back down to the curiosity, having curiosity about asking questions. I think it’s really hard to innovate within an industry. If you’re embedded, if you look at Nobel Prize winners, many Nobel Prize winners are boundary crosses. They have expertise in chemistry, but then they kind of, I’ve got this interesting biology thing just now. And I think, know,

Kate O’Neill (she/her) (16:09)

Hmm.

James Taylor (16:16)

my brother-in-law owns a taxi company. And taxi companies were changed dramatically with Uber because the average age of a taxi driver was 58. And they’re not sitting around making apps really. So I think it’s quite hard to innovate within an aside. And I’ve seen different companies try to attempt different ways of doing this almost like having a kind of a, almost a separate part of the business that’s focused on

growth, going 100 % for growth while they have another team that’s focused on that kind of just transformation, getting the business to work more efficiently, more effectively, because it’s slightly different head spaces. And I think it’s very difficult sometimes to be boundary cross in that way.

Kate O’Neill (she/her) (16:59)

Right, right. But the value is there. think it’s so right. The one thing that you and I have in common is that we bring these different fields of interest to the work that we do, know, music and language and everything else. And you and I both have an interest in animal rights. And, you know, I think just having those those radar, those antenna up for different fields and what’s meaningful and relevant in those fields, you know, this ties into the title of this book, What Matters Next is that I think one of the things that we miss is that

what is fundamentally human is our sense of meaning. What is meaningful is what matters. Meaning is always about what matters at every level. So whether we’re talking about semantic meaning, how we communicate through language or patterns or purpose or significance or truth or relevance, or all the way out to the biggest, most macro, big picture, what’s it all about? Why are we here cosmic, existential kinds of meaning?

It’s always at every level we’re talking about what matters.

And I think that distillation is really handy as a shortcut for asking the right kinds of questions in an environment, whether you’re crossing boundaries in an organization or not, inside of a silo in an organization or crossing across many layers of the growth people, the retention people, the people who are thinking about the two moves ahead, what matters and what’s going to matter. And what I advocate for in this book is really about

not timid incrementalism, where you’re too timid to take bigger steps, but the right sized incrementalism where you’re moving yourself a step at a time into the next thing and the next thing, because you’re making very sensible choices about how to navigate between what you know matters now and you’re balancing that perspective with what you can see about the future, what you can see about what is likely to be the priority, what’s likely to matter well ahead of you. And I think that’s

That’s what helps make those blended perspectives really helpful too. When you’re bringing together people from across the organization who have different metrics for success, different OKRs, different priorities and ways that they’re gauged for success. But if they’re able to bring it together at a higher level and say, what matters across everything that we’re talking about is this fundamental concept, then you start having really meaningful conversation.

James Taylor (19:25)

that word idea of meaning, I always find it interesting talking with clients sometimes and they’ll say we’re thinking about this, this is what we want. And then just asking the follow up question, what do you mean by that? Because me being the outsider, I can ask dumb questions and I have no problem about asking dumb questions. And what it does is it makes them just have to pause and to think about what do they mean by that? And I guess this is the great thing that you and I get to do, we’re not academics.

Kate O’Neill (she/her) (19:37)

Yeah

Yeah.

James Taylor (19:55)

So we are getting to have real deep relationships often with clients and have that iterative process on our work and finding what’s working, how do we need to refine that, how do we need to define that in a slightly better way. As you’ve been working with clients, I’m interested to get an understanding of, in the book you have these set of tools to really help leaders make decisions specifically about the future.

and you mentioned the kind of insight foresight. Was there a particular occasion that when you were working with a client, it really helped you distill any of these particular tools or it made you kind of rethink actually what they think I’m thinking, I’m saying is not that thing, but actually that’s interesting or just that kind of little quick feedback loop that you meant, actually this is, I’m gonna change this tool because it’s gonna be more useful for them.

Kate O’Neill (she/her) (20:45)

Yeah, yeah, it’s something that’s evolved over the years and it-

It’s my own insights, my own process that I talk in the book about keeping an insights inventory, you something where you’re, you’re keeping a log of the most meaningful insights and revelations that you’ve had about your business, about your life, about your priorities, you know, whatever they may be. But it was something that over the years of working in different industries, different countries with different types of leaders, ⁓ I would just hear the, these kinds of patterns.

of feedback. For example, one of the observations is that we think that we learn by asking questions and getting answers and that’s how we make decisions, but that’s actually only the very first step and that usually results in when you ask a question, I’ll ask this of your listeners and viewers right now, when you ask a question, how often do you get a different answer from every single person in your team or in the room, right? It’s probably every time.

And

the reason for that is not that everybody’s wrong, but it’s that proverbial elephant that we’re all on different sides of, right? We’re all seeing the trunk or the nose or the tail or whatever. And it’s really important that what we do is synthesize that, that we take all those partial answers, which are part of a truth, and look for what the whole truth is. At the best we can. We’re still human. We’re only going to be able to see what we can see. But what we do is we try to make some kind of whole list

sense out of that and then use that kind of clarity that we get from that insight.

That is an insight, know, the sort of compressed truth of those partial vantage points that then becomes this prism, this lens that lets us see more clearly into the decisions we’re making. So we may be able to then take it and say, look, this decision we have to make today about, you know, implementing this call center software, we have to decide what our taxonomy is going to be. Like, are we deciding between this breakdown and that breakdown? It’s going to help us to be able

to say, well, one of the insights we have about our company is that we truly value design and experience. Branded design is a really important facet to us. So we’re going to skew toward this decision over here. It helps us make decisions more readily. What happens along the way, though, is so interesting is that we sort of have this exhaust of

foresight I call them bankable foresight because what you don’t have to do anything with them right now you can set them aside but it starts to give you a clue about things that are going to matter like even in that decision that taxonomy decision it’s totally made up and not

not very vividly depicted, but you can even see how maybe saying, well, we’re going to make this decision toward this organization of our content because we’re a design and experience oriented company starts to say, well, but also we need to reconcile at some point, what do we do about this other organization? If people have a more natural inclination to that, we need to address that at some point and figure out, does this mean a partnership? Does this mean, you know, a referral type of situation? Those are just the

types of opportunities that become much clearer and more cogent by working through this process diligently. And I’ve just observed that through road work, right? Like you said, it’s just that the routine of being in the room and being in boardrooms and…

having the privilege of being on a whiteboard with customers again and again, and being in a room, being asked the questions and being able to turn the questions back around to people and ask for clarification, ask for what that means to you, et cetera. And you just start to see these patterns. And so hopefully the distillation of these patterns to be able to share them with others through the book is going to help there be a lot more clarity as people are making these important decisions about.

technology deployment that affect us all.

James Taylor (24:51)

sounds almost a little bit like Charlie Munger has his mental models, you’re creating these kind of mental models that you can see. it’s, I’m reading a great book just now about Vienna during the, I guess, the end of the Weimar Republic before and then before kind of early 1940s, it went through this, it was called Red Vienna and then Black Vienna. And it’s one of the things that was pushed back on because it was known as being empirical, you know,

Kate O’Neill (she/her) (24:54)

Yeah.

James Taylor (25:20)

Can we test this? Because that, and that was probably the greatest thing that Vienna gave to other parts of the world. It’s a sense of, is this testable? Is it repeatable? And if it’s not, then it’s just, that’s a nice idea, but it’s not real. It’s not like a mental model. So what you’re saying is you’re able to kind of create those insights from that, and then you’re able to test them with different clients and say, is this true at the end of it? Is the response we’re getting, is that correct?

Kate O’Neill (she/her) (25:27)

Mm.

Yeah, yeah.

Right, right. Or does it lead to clarity? think, you know, some things are testable in a quantitative way and some things are testable in more of a qualitative way. And the qualitative sense of, you know, does a leader sort of sit up more in his or her chair and go like, that makes so much sense. I suddenly have a new insight. I was doing a guest lecture for my friend at Harvard who teaches a class there with executive leaders. And so, you know, the really wonderful thing about

doing guest lectures in schools where executives are going to get further education is they’re coming already with experience and business projects and some examples that they start to think about as you talk through these scenarios. And I was sharing this process. so at each step of the process, I was asking these executive learners, do you have examples in your organization that you can see how this might apply? And every time somebody would go like, my gosh, yes.

share an example and how it was immediately helping the clarity of their thinking to be able to put these these steps in place. And I just I remember having this incredible sense of being able to affect change like through that moment and witnessing people coming back with very vivid examples, in some cases, you know, way too long a story, but very helpful to get to hear, like here’s the

Here’s the way that we’re gonna be able to take the questions to partial answers and distill it into insights. Immediately I can see how the many respective peoples on my team, that their perspective is going to be at odds with one another unless they have.

This was something we did at Netflix. each had our own area of measurement for what we needed to affect as a team, sort of at our team level. But those needed to roll up holistically into a metric that we all cared about as a department or as a company and so on. It’s almost like a taxonomy of metrics.

And I really found that process to be so helpful. It’s one that I share a lot with clients, you know, to be able to have that one unifying metric, but then everybody has their own version of it or something they feel contributes to it. So you’re not only looking at your one metric for your own team, you have to have some way that that resolves to something more significant than your own work, something that has more wholism than that. But it is, so wonderful to hear the real life

lived experiences of executive learners in those kinds of situations who are in the moment applying these insights into their world and figuring out how they’re going to solve problems and take them back to their organization.

James Taylor (28:38)

I guess one of the other interesting things we’re starting to see now, I you have a, I know you’ve written a lot and you’ve spoken a lot about the use of data for good and for bad. And a few years ago, I was introduced to this idea of synthetic data. And I thought, oh, this is fascinating. Where, let’s say San Francisco, where I I used to live and I used to be based as well. If we want to change something around, let’s say policing in this area, then there’s a certain amount of

Kate O’Neill (she/her) (28:46)

Mm-hmm.

James Taylor (29:07)

data that we have, we could think about how could that affect the crime rate in that place. Or what we can also do is we can add synthetic data in order to get a wider data pool in order to test it. And then we get some different results. So I guess what’s interesting, what you’re talking about now is, some of these things, you just have that conversation with that CEO or that senior leader and trying different things. But I guess what we can also, going a few steps forward,

Kate O’Neill (she/her) (29:17)

Mm-hmm.

James Taylor (29:35)

is you can take some of these ideas and you say, listen, rather than actually test it out on the real business or this real department, let’s create the digital twin of that with some synthetic data and let’s see what actually happens. Let’s test our assumptions.

Kate O’Neill (she/her) (29:49)

Yeah, that’s interesting. I had seen that kind of thing in practice in a couple of different areas. So when I read my previous company, the analytics and strategy company, we were doing a lot of experimental kind of modeling and helping companies figure out how to model their company in data.

sort of say, are the meaningful things we need to capture here? We need to know about inputs and we need to model what’s happening kind of internally and then we need to know about outputs and what the overall system looks like. And along the way, in order to synthesize or to be able to simulate that, to know if a change over here would affect the outcome over here, you would often have to create synthetic data. You would have to create kind of bogus use cases and inject synthetic data into different places

of the model. yeah, as it relates to the insights and foresight, I hadn’t thought about that parallel. It’s pretty interesting. I also think, you know, synthetic data is something that comes up a lot when you’re dealing with AI ethics and, you know, counterbalancing some of the bias in data sets and so on. So that, again, circles back to many of the underlying

sort of dilemmas that we’re trying to deal with when it comes to using these models in the first place, using the insights and foresights and the now next continuum and the harms of action and harms of inaction. All the other models that I’ve introduced in this book are very much intended to deal with the reality of the challenges that a data-based and algorithmically optimized and technologically advanced.

a society is leading us to. You know, we’re leading, we’re being led into or leading ourselves into a world where many of these, decisions that we make have scale and capacity and consequence well beyond what many leaders were ever taught to deal with in business school.

Or if they didn’t go to business school, what they learned through years and years, decades of being in the trenches. But the consequences are just so much bigger. So they need new models. They need clearer thinking and they need the ability to have some sense that what comes in over here is going to have this kind of an echoing impact over there. And the only way we can really do that is by trying to demonstrate it with different use cases, different examples as we’ve done throughout

the book, showing with some clarity how some of these past to present to future consequences play out, trying to give some clarity around some of these ideas around like transformation and innovation like we’ve already talked about. You know, all of it just comes down to clearer thinking. And at the end of the day, if someone is approaching these technology decisions with clearer thinking, I’m really hoping that they’re going to be making better decisions overall.

James Taylor (32:48)

So you’re brought in by these companies to help them with that clearer thinking, that decision making. Where do your ideas come from? Where do you go to get inspired? How do you go about developing your ideas? there things that have tried and tested for you that you kind of caught you in your kind of box of tricks that you tend to go to?

Kate O’Neill (she/her) (33:08)

Yeah, you know, I, like you, I am drawn to many fields and I agree with the notion that innovation or, you know, new ideation comes often from the juxtaposition of ideas from different spaces. Like you were talking about Charlie Munger’s sort of mental models and I also am a fan of the Zettelkasten, you know, the idea of kind of a thought process, like a thought cataloging process. So I read a lot of across a

lot of different fields, economics, history.

physics and so I’m constantly recognizing these meaningful sentences or something that someone says that I go like, that’s really interesting. I wonder if that’s true in another space. I wonder if that would be true if you applied it over here. And just keeping a set of interesting observations that maybe sometimes you encounter randomly as you’re looking for something else. A lot of that is cataloged in my notion. I use notion as many people probably do who are listening here.

And so you go to search for something if I’m looking for if I just search for the word insights in Notion, I might come back with a whole lot of different documents that I wasn’t looking for, but it might go like, yeah, the Amsterdam engagement that I had, that was an interesting one. And thinking about smart cities and AI ethics and, you know, the responsible deployment of tech as it relates to multiple stakeholders, that could really apply in this health care company example that I’m thinking about right now. And so I think you do.

you just kind of, if you design your workflow well, you sort of build a certain amount of serendipity into it. And you get some of these cross-pollinization opportunities sort of just by the way it happens. And so that’s what I look for. And sounds like that’s probably somewhat similar to your approach too, is it not?

James Taylor (35:02)

Yeah, I mean, I have a lot of fun. I used to have, I’m listening to a book just now, The History of the Notebook, going way back into the Egyptians and then the Venetians and the Tuscans. And so this idea of like just keeping a note, things are obviously important you want to reflect on. So I’ve always done this. I’ve always an idea, a thought, or I read something or I see something, I carry my notebook everywhere with me.

Kate O’Neill (she/her) (35:10)

yeah.

James Taylor (35:31)

But then I decided to go with AI, because I’m fascinated about how we can use AI to become more super creative. I then said, okay, so this is the concept, this is the idea. So I then I use an AI to then say, take this idea, this concept, this phrase, and turn it into a visualization, a visual representation of this idea. That could be a graph, it could be something else. Okay, now give me something in terms of a metaphor that I could use.

that relate to that story. Then give me a phrase that pays. Then give me the data that supports that. So what I’m trying to do is because often we’re speaking to different types of learners and different types of audiences, I’m trying to figure out at what stage am I better, like just with a real sharp phrase that really just kind of lands. And then what point am I better actually with something visual that represents that or a metaphor or…

Kate O’Neill (she/her) (36:13)

Right.

Yeah.

James Taylor (36:29)

a key data, a key graph or something as well. So that’s why I have a lot of fun using AI just now to help take that idea, that notion, that thing, and then kind of go across. And then that kind of builds that intellectual property, like kind of database that I can go. And sometimes then that feeds on something else and I can say, actually that image, I can do something else. I know that a lot of, you know, especially like you and I, speak to lot of global audiences and

Kate O’Neill (she/her) (36:42)

Yeah.

That’s fun.

James Taylor (36:59)

One of the downsides, we have a mutual friend called Sylvie Di Giusto, and she gets booked all the time. And one of the benefits being a German speaker, a native German speaker speaking English, is often she’s much more direct in her language. Whereas as us, as native English speakers, we can get a little bit overly flowery, a bit fancy, I guess, which is a detriment sometimes when you’re speaking to people whose English isn’t their first language. So if I’m speaking in parts of the world with English, like Vietnam,

I knew it was much easier to get my message across with a very strong visual rather than like two paragraphs on a particular idea. So I do kind of what you do, like taking these notions, finding a way to capture them and then thinking how can I expand that so it’s multimodal in some way.

Kate O’Neill (she/her) (37:48)

Yeah, that’s great. I love it. That’s so fun. And I love that it ties back to this history of the notebook thing, because that is very much my kind of nerdery. we’re very aligned on that.

James Taylor (37:51)

So in this.

Yeah, yeah. it’s

fascinating reading all the what the Venetians used to do. They used to have like five different notebooks and how they would keep these notebooks. And if you’ve ever read any of Leonardo da Vinci’s notebooks, we used to write right to left. So you didn’t think anyone would copy his work. So a lot of things are particularly new. But what I find so amazing just now is how, especially with generative AI, we’re able to help that.

even richer, even fuller as a way to be able to do it. And for me, that’s the exciting thing. And I hope that we go a little bit more towards that because my biggest concern, talking about the ethics, is we end up going the same way that we went with social media, where it had so much optimism, know, when it initially started many of these social medias, and we kind of went to a slightly different place with it. There probably wasn’t, and a lot of people that were starting those businesses didn’t really

envisage. And that’s my thing with AI is like having people like you speaking events, talking about the human side and talking about what are the questions that we’re not maybe asking that we should be asking. think that I think is a really powerful thing to do. So you mentioned Notion, are there any other tools or apps that you just find indispensable for the creative work that you do?

Kate O’Neill (she/her) (39:06)

Right. Right.

Yeah, yeah, mean, the writing obviously takes place across its own set of tools, Scrivener and Notion and Evernote and so on. But I’m a big mind mapper. I love MindNode and I love the ability to sort of sketch out in MindNode, whether it’s to just get at a crude level, you know, sort of like organize, what are the component parts of this thought? Let me break them up and see them, you know, visually.

Or in some cases, it’s for really trying to catalog something that I’m not as familiar with. Like for example, if there’s an opposing viewpoint to my own, like if I see someone put out an idea that they’re advancing that I think ideologically, philosophically, like we’re not on the same page, but I need to understand what their perspective is.

in order to refute it even, you know, or if I want to have some standing, if we’re on a debate panel together or something like that, I want to be able to understand their perspective. And so I may just have to take it apart in my note, I find as a really useful tool for me to do that and just plot different aspects of it. But I use AI a lot as well. Sorry, go ahead.

James Taylor (40:30)

think

that’s great. Someone told me the other day when they write a book, they do the first draft and the second draft and then the third draft that they actually show to people and then they also do another draft. Well, what they do is they use AI to basically strong man, I guess, against the ideas in the book and read it from the perspective of someone who is the absolute opposite who is going to destroy the book and the ideas in the book. Yeah.

Kate O’Neill (she/her) (40:51)

Yeah.

I did that. I did that a lot

with What Matters Next. Strawman, I think, is what you’re looking for, right? The idea like here, walking through this, there were a few places where there are people I name who have different ideas. Mark and Andresen, for example, holds different philosophies to mine, and they’re opposing philosophies in some respects. And so, yeah, I would use generative AI sometimes to say,

James Taylor (41:02)

Sure man, that’s the word.

Kate O’Neill (she/her) (41:24)

pretend you’re Mark Andreessen and you’re reading what I’ve just written, how would you push back on this? And it’s so helpful. It’s so helpful. Because you can think what that might be, what the objections might be. But when the tools that have actually been trained on lots and lots of documents that understand Mark Andreessen’s point of view, know, like that come from a…

come from myriad perspectives of Marc Andreessen’s writings over the years, it’s just gonna be better. It’s just gonna be that much more able to distill what the pushback is likely to be. And so it helped me to say either I need to shore those things up or I just need to not care.

And one way or the other, it doesn’t matter which way you choose to go. It’s just very helpful to understand what those objections are likely to be. So yeah, that’s a really helpful tool in the process. But also just using generative AI, like you described a really wonderful rich process for modeling different types of learning. I also use it to distill many times across the sort of digital Zettelkasten where I might have the…

the physics clips and the economics clips and politics clips and all sorts of things all in one space and have AI kind of summarize. If you go through and look at all these notes that I’ve saved, what seemed to be some of the common themes that maybe I’m missing, that I seem to be drawn to? And it might say like, you seem to be drawn to the concept of entropy across all these different systems. Like, yeah, that’s true. I am really drawn to that. Good observation, AI. So maybe now I’m actively going out and reading about entropy.

James Taylor (42:55)

Yeah.

Kate O’Neill (she/her) (42:58)

more directly so that I understand what it is my mind is instinctively drawn to. I just think that there’s such opportunities, as you say, for us to use these tools in ways that just make us better at what we’re already doing and take us leaps and bounds, you know, fields down the road so that we can just do what we’re doing and do it much more effectively.

James Taylor (43:21)

Now we’re going to have a link to your new book, but I’d also love to know, is there a book you think our listeners should be also checking out, maybe some that’s been influencing you over the course of the past few months, you just kind of been returning to, it’s kind of, maybe you reassess an area or got really interested in a particular area.

Kate O’Neill (she/her) (43:40)

There’s so many. I think that in this book, the ones that, these are classics, but the ones that I taped up the tables of contents of Good to Great and Blue Ocean Strategy as two of the really most effective business strategy books of the last few decades. And I wanted to make sure that,

Conceptually, there was a flow that was happening in the book that would bring readers through that transformative process of, you know, sort of starting at a more abstract argument and working your way through to how do you implement, how do you operationalize and how are we going to take step by step through that? So for me, those were books I returned to many times. I just flipped good to great or bluish and strategy open to any page and sort of read a paragraph over it.

and thought, all right, I’m not hitting that level yet. I need to level up what I’m doing. And it’s funny, because it actually sort of, for me, I know you and I have music in common and songwriting in common, and it was similar to a process I learned from Pat Patterson, the really wonderful songwriting instructor at Berkeley University in New England. He has this idea that if you’ve written a verse and a chorus,

And then another verse in the chorus that you might look at one of those verses, maybe your second verse, because the second verse usually is weaker than the first, and you’ll kind of go like, oh shoot. He usually says something different than oh shoot, but oh shoot. Like now I’ve written a better verse and I need to go and write a better second verse. So it’s always whatever is your level that you’ve hit with one section, your other sections need to level up too.

And that’s what I find across my writing. It’s a trick I’ve learned from my songwriting that if you really hit it out of the park, it’s like, shoot, now I just made my job harder across the entire rest of the book. I have to level the rest of it up.

James Taylor (45:45)

that’s great. I mean, I think

it’s, you know, because there was an, I remember there was an Ezra Klein from NPR said something along the lines of, you know, that idea where you’re sitting at one level and then, you have great taste and your craft or your art is not at the level of your taste yet. But there’s that constant, that’s constantly what you’re trying to do. And I think it’s very hard in what you and I do in the world because

Kate O’Neill (she/her) (45:58)

Yeah.

James Taylor (46:11)

There is an artistry towards what we’re trying to do, but then there’s also very much the business side of it as well. And one of the hardest things, last night I watched a great movie again, because I was talking to someone about it called The Big Night with Stanley Tucci about a great meal. And the movie is basically really about this idea, yeah, this idea like this tension we have between creating great art, something that’s gonna live beyond us and really influence other people to doing the stuff that pays the bills, as you would say in the States.

Kate O’Neill (she/her) (46:24)

yeah, yeah, yeah, And Tony Shalhoub,

Right.

Yes.

James Taylor (46:41)

And there’s that constant tension that we have to do. And I guess, know, where I see amazing companies sometimes is that they have this aspiration to create great artistry in what they’re doing with the technology just disappears. You’re not really thinking about the technology, but then they have the execution and the quality of execution and planning and strategy behind that to be able to make that happen. And that’s where it gets really exciting when you see that as well.

Kate O’Neill (she/her) (47:07)

Yeah.

James Taylor (47:09)

Where is the best place for people if they want to learn more about you, want to bring you in to come speak at their event, want to bring you in to consult, where’s the best place for to go and do that?

Kate O’Neill (she/her) (47:18)

My website is KOinsights.com. My company is KOinsights. KOinsights.com is the best place to find me, my work, the book, other books, and speaking information. I also spend a lot of time on LinkedIn, so I’m Kate O’Neill there, on Blue Sky, Kate O’Neill there, and so on, so you just look for me. There’s a lot of Kate O’Neills in the world, but if you search Kate O’Neill tech humanist on Google, you will usually find me.

James Taylor (47:46)

Well, what matters next? A leader’s guide to making human-friendly tech decisions in a world that’s moving too fast is out now. Kate O’Neill, thank you so much for coming and being a guest on the Super Creativity Podcast.

Kate O’Neill (she/her) (47:59)

Hey, thank you, James. I really appreciate it.

Hi, it’s James Taylor here, and welcome to another episode of the SuperCreativity Podcast. Now, last month, I had the incredible opportunity to deliver a keynote in Dubai for duTech, a company at the forefront of Hyperscale Data Centers, Cybersecurity, IoT, and Cloud services. As I spoke to their leaders about the future of innovation, one concept that really resonated with them was the power of mentorship—not just as a way to develop talent but as a driver of creative thinking and problem-solving in organizations.

And today, I want to share that idea with you. It’s something I call ‘The Barbell Guide to Creative Mentoring.’ And it could just change the way you think about mentorship forever.

If you’ve ever lifted a barbell in the gym, you’ll know that to create balance, you need weight on both sides. And that’s exactly how I think about mentorship. Most leaders understand the value of having a mentor—someone older, more experienced, someone who’s been where they are now and can offer guidance when they face those career-defining decisions. This mentor acts like a sounding board, helping you navigate challenges with the wisdom that only experience can provide. They’ve been in the trenches, they’ve made the mistakes, and they can help you avoid the pitfalls.

But here’s where many people stop. They focus only on having that one mentor who’s ahead of them, but they forget the other side of the barbell. And that’s where things get interesting.

Why You Need a ‘Reverse Mentor’
Confucius once said, “Respect those younger than yourself.” And I think he was onto something. If you really want to supercharge your creativity and stay ahead of the curve, you also need to have a mentee—but not just any mentee. You need someone younger or less experienced than you, someone who sees the world through fresh eyes and isn’t tied down by ‘how things have always been done.’

At first, it might feel like you’re mentoring them, passing on your knowledge, guiding them in their career. But here’s the secret: in the process, they start mentoring you. Their questions—sometimes naïve, sometimes surprising—can challenge your assumptions, expose your blind spots, and help you see opportunities you might have otherwise missed. They bring fresh perspectives, energy, and ideas that can shake up your thinking in the best possible way.

I’ve personally experienced this time and again. Some of the best insights I’ve gained in my career have come not from the seasoned experts but from those just starting out. Their curiosity and willingness to question ‘the way things are’ help me stay sharp and innovative.

The Reverse Mentor Challenge
So, here’s my challenge for you:

1. Identify someone younger or less experienced in your industry or organization. This could be a junior colleague, a recent graduate, or even someone outside your usual network.
2. Set up a 30-minute conversation, but instead of you giving advice, flip it around. Ask them about their thoughts on your industry, how they see the future, what they think could be done differently.
3. Capture at least one insight from that conversation that shifts your perspective. And I promise you, there will be one.

Closing Thoughts
So, the question I leave you with today is this: Are you balancing your barbell? Do you have a mentor who can offer guidance from experience? And do you have a mentee who challenges your thinking and helps you see the world in a new way?

Great leaders—and great creative thinkers—do both. Because when you have weight on both sides of the barbell, that’s when you find balance. And that’s when the real innovation happens.

If you take on this challenge, I’d love to hear about it. Drop me a message on LinkedIn or tag me on social media with your biggest insight. Let’s build more creative pairs and drive innovation together.

Until next time, keep learning, keep creating, and keep pushing the boundaries of what’s possible.