Is AI a Technology or a Leadership Challenge?

Alison Woo: Welcome to the zest for more podcast.

Gwynne Oosterbaan: where we are all about finding joy beyond the job. I'm Alison Woo and I'm Oosterbaan

Alison Woo: I'm Alison Woo And we're two former communications colleagues and friends found ourselves asking a lot of the same questions. ⁓

Gwynne Oosterbaan: Like, can you have a big job and a big life all at the same time? And what do you do and how do you keep that big job when big disruptions like AI happen?

Alison Woo: So our latest guest has actually one of the zestiest lives around. She's actually ⁓ a friend and a colleague and someone I've known for more than a decade and someone we so respect and admire. Li is the legendary leader, I consider her the Bono of digital innovation and transformation. ⁓ started as a journalist, then a researcher at Gartner, and she's ⁓ the leading authority on how to use digital for leadership purposes. Like, how do you think about it as a leadership challenge? She's the author of six books. You may know her very first one, which was called Groundswell that out in 2008 and was the foremost authority ⁓ to That the social media thing is real and listening to your customers was non-negotiable. ⁓ She now written her latest book called Winning with a AI, the Day Blueprint for Success. Charlene, we're so to have you here. Welcome to the show.

Charlene Li: Thank you for having me.

Alison Woo: So you have been through the first wave of transformation with digital when it first began. Is AI different now? And if it is, how?

Gwynne Oosterbaan: Bye.

Charlene Li: It is different. it feels like I've been hit by a Mack truck in some ways. It is so fast. It is happening. And the adoption is so easy. It's anybody with a browser can pick it up. And what's interesting is that I find that people are using it more in their personal lives than in their corporate lives. So you're having this disconnect to where people are familiar with it, but they haven't quite figured out how to use it for work and in many cases are being banned from using it at work. So there's a big disconnect. mean, so it's happening at a speed and scale that is very different from other technologies out there. It's not this diminished the other ones, but this one feels more seismic.

Alison Woo: And you talk a lot about, even from before in the roots of digital, that it's never been about the technology, right? It's really about the leadership and the way leaders think about these things. You're absolutely right. Some people are like, do not use that here. Don't put any of our work here. And then the other side of the spectrum is we have to use AI for everything. So we know there are people and companies who, in their objectives, it's you better figure out how to use AI for something. How do you counsel leaders to help them think about where they should be in that spectrum?

Charlene Li: that one of those approaches helps because one is just ignoring the reality that it is here and that it will be a part of the way work is done. The other one is directionless. ⁓ is ⁓ It's being abdicated to say, I don't know how to use it. You go figure it out. And in cases, leadership is needed and leaders create change and change is really hard. And leaders typically like to have the answers. They like being the experts. That's why they were promoted. with AI, ⁓ of us really have all the answers. All of us are ⁓ by our fingernails, and that's a very uncomfortable place for leaders to be. And so we just procrastinate our way to not have to make any decisions around AI because we don't want to be wrong. So this is a new leadership skill that I think we have to exercise to be able to make decisions to point people in directions. And the way to think about it is to say, I don't have the answers. I'm being very honest about this. I ⁓ know exactly the way to go. But I have a direction of travel that we want to be in. This is our strategy. This is where we want to be heading. This is what our customers need. We have a vision for that. ⁓ know the business really well. This is what we need to be doing. How do we use AI to accomplish those things? I don't know the answer. but I know this is what we have to do with it. And that gives just enough structure for people to be focused because the number one problem with the technology, it's a bright, shiny object. And we go, wow, what a great hammer. What nails can we hammer with us? That is not a good way to approach it. So I think it's a leader responsibility to give people direction, to give some sort of structure to help us think about how to use AI to achieve our biggest strategic objectives.

Gwynne Oosterbaan: So it sounds like when you're talking about bringing people together, there's a skill of collaboration and good listening that would be inherent to that. How much of that do you think leaders today are trained to do? And are there ways that you're trying to invite them to engage in this scary word called change?

Charlene Li: I think that we have in our cases, mostly managers, managers of the status quo. Leaders are a very different ilk. They create change. And so really good leaders are comfortable leading change because that's what they do. so how do we prepare those managers to become leaders in the same way you ask anybody to take on change and small steps. ⁓ it's not to say we're going to make it easy and comfortable for them, but we're going to provide some scaffolding. We'll provide some foundation, some training wheels to make the process a little bit less scary. And where I think structure is so important. Right? Guard whales, white why strategy is so important. It's like, we're not talking about the universe. We're talking about going in this direction. And these are the choices we want you to make. And these are the changes we want to make. Yeah, it's going to be scary. We're going to be here holding your hand. Come on this adventure with us. that is what leaders have to do for each other for themselves. In particular, ⁓ know that leadership, the number one thing that number one thing you have to lead first is yourself. If you can't master that. then forget about leading other people. how do you lead yourself into this scary place? How do you help yourself be curious AI to practice it, to carve out the time in particular to learn it and to use it? AI is so important to develop, and you don't ⁓ do by watching YouTube videos. ⁓ You AI fluency by practicing it. That's how you become fluent with anything.

Gwynne Oosterbaan: as someone who's worked with AI teams and mostly in like a pharma setting, but for at least six years, like even before chat GPT, there was a lot of angst and then a kind of like, have to get on this bandwagon, we have to be first, we have to show people we know what we do. and was very FOMO. You have a counter to FOMO. Can you explain what that is and how it relates?

Charlene Li: Sure. Yeah, I love this. I call it FOGI: fear of getting in. So you have FOMO drawing you in and FOGI going, no, I don't want to go there because it is just going to be this black hole of confusion. And it's very uncomfortable. So we're pulled in both of these directions. I feel that way every time I come across something new, like the hot thing right now is open claw. I'm so curious about that, but... Getting into that whole space is like I don't want to get into it. So we all experience it to some degree or another I think that it's recognize this is not to fight against it. We all experience FOMO and FOGI and it's to find that path down the middle that makes a lot of sense for you and to block out all those noise again, there's much noise. What's the latest model was going on with Claude mythos and It's all a distraction for what are the biggest strategic choices you need to make as a leader right now today. So focus on that because that's something you know, and you can control and then use that as a starting point for everything else that you do.

Alison Woo: You talk a lot about AI fluency, right? And you talk about the formula for helping people get fluent. Can you talk about those three T's and help people understand where they can begin? Because for a lot of people, think there's a lot of people we certainly know who are even afraid to say, yes, I've heard about AI, but I don't know how I'm supposed to start using it. What's your suggestion?

Charlene Li: The three T's are ⁓ access to the tools the training and then the time. So we find that organizations for the most part are giving people access to some tools. ⁓ if it's copilot from Microsoft, good. It's getting much better, especially the new version coming out called Cowork. ⁓ It's really and it's very safe, secure, it's enterprise-grade. But that isn't just giving people a tool. You need to provide them with training and in particular top-down training that gives you an idea what AI can do, but just as importantly, what it cannot do. What are its limitations and understanding that responsible and ethical use of AI so you don't get in trouble and that you make good decisions. But then there's actual training that comes from using it, knowing how to use AI in your job and how to effectively use it. ⁓ again, potentially taking some courses, learning from your colleagues, having that sort of sharing that comes back and forth. ⁓ I've learned constantly from the people around me how to do this. And the time. Are we protecting time for people to learn and to experiment? This is not about pilots. This is about you practicing. And I think of AI fluency similar to learning how to use chopsticks. The first time you use chopsticks, again, this is if you don't come from an Asian household, you're looking at how do these two, how, like what? And you figure it out and then it's really awkward. And then eventually one day you're just picking up food without thinking about it until you get to a slippery noodle thing. Like, how do I do this again? AI fluency is the same way. At some point it becomes natural. And very importantly, you learn how to use AI to tell you how to use AI. That's when you break through and you figure out, I'm not just using it as a search engine. I'm using it as a thought partner. I'm using it as my tutor. I'm using it to help me get my job done. And you turn to it. You rely on it. You trust it. the same time, you know what its limitations are. And you realize very quickly that if it's not giving you the results you want, it's not the AI. ⁓ That's the problem, it's you. It's the way that you're using it. you have to change and adjust and that's where that fluency, that comfort, that flow, that's you go, I'm really with this. I still have a lot to learn, but I'm very comfortable with it now.

Alison Woo: Well, you're actually learning from this yourself and actually in the book, the chapter I turned to at the very beginning was actually really at the very end where you talk about your own journey of using AI with you and your co-author to write the book. Can you talk a little bit about what you experienced and why people should not be afraid that humans will no longer be necessary?

Charlene Li: Well, AI is doing so many things. It can do things that we cannot do. And what we found with the book, it was great at taking all this masses of information, our interviews, our conversations with my co-author, and it helping us to structure it, create outlines, do research. I mean, we would have had teams of editors and researchers to do this in the past. But ask it to write a chapter, and it's not very good at it. It defaults to things like write sentences. It's not this, it's that. It uses ⁓ dashes even when we tell it not to, like in bold letters, like do not do this and it still does it. So it's just, it has a hard time holding a particular thought and structure across an entire chapter because of the way it works. It is a probabilistic It just figures out what the next word is. It's not necessarily thinking about the entire arc of the chapter. So it loses track, it repeats itself. So it's not great at that right now. said, it's getting better and better. AI is good some the execution aspects of things, but what made the book ⁓ really good was our thinking, the way that we ask And there will always be a role for us to bring our individual experiences, our humanity, the way that we synthesize things into a particular problem. AI can only be as creative and innovative as the questions you ask it. And so if you want to be more creative and you want AI to be more creative, then you have to be more creative too in the process.

Gwynne Oosterbaan: So. Which raises the question of how do you teach someone to be creative? And back to the earlier conversational thread around leadership and then how do we train leaders to be better at either taking risks and embracing change and bringing people along. I love that point you made about the probabilistic design of AI is only going to tell you the next thing and not the arc. Do need help thinking about the arc on what they can only do as humans versus the AI.

Charlene Li: I keep coming back to leaders create change. Leaders see an opportunity. They see something that no one else surrounds them and galvanizes themselves and other people to help create that change. And I think it's the same thing when it comes to AI. What you see, what you're curious about is like, wonder if AI can do this. I wonder, can AI answer this question that hasn't been asked before? So it's this curiosity. ⁓ the questioning. It's the ability to look at the world differently than anyone else has and to ask the question that no one else has or to ask it in a different way. by asking the question, you're directing people towards a particular ⁓ And ⁓ last, very last epilogue of the book, we talk about the world of imagination. We have absolutely no idea what AI is going to create. ⁓ people call me a futurist. I'm like, I have. No idea. I can talk about everyone else, but we can't even imagine what the Internet was going to create back in 1995. we're now in 2026. We have no idea this is going to look like in four years time. In 2030, but I know it's to be different, and this is our opportunity as people as leaders to that future. It has been written yet. And so often we think, ⁓ AI is just happening, regulation, everything is just happening. There's nothing I can do. Absolutely no. We shape the future of this technology and whether it's going to be helpful and beneficial to us or harmful to us with every action and decision that we make. And so when you're talking to a vendor, ask, how are you doing this responsibly and ethically? share with them, these are my strategic objectives. Don't even listen to their pitch until they understand what your problems are. your state legislators, how we protecting these interests? Are you thinking about them? We have a role to play in what AI does in our communities, and we have absolutely a role and opportunity to shape that.

Alison Woo: So one of the things that people have been very reticent about, right, is the potential loss of jobs. So there's a lot of fear about what is the role of work? What is the new work that will happen? Can you talk a little bit about what are some of the realities or possibilities of how people should be thinking about framing that up?

Charlene Li: Yes, I think if a leader were to say to people, don't worry, AI is not going to take your job. First of all, it's not necessarily true and they won't believe you. They just simply won't believe you. our People want us to do two things. They want us to be honest with them and fair with them. So the honest response is, I don't know if AI is going to take your job or my job. And honestly, I can't guarantee that any of us are going to have a job. What I will do as a leader is say, I do know that AI is going to be impactful in the future, and we're going to do everything possible to give you the tools, the training, and the time to prepare you for that future so that you can maximize your potential and while you're at this job to contribute in the best way possible to our strategy. And it'll also be better equipped to go wherever you go and to maximize your employability. So that's, that's the agreement, right? That's being honest and that's being fair. And the reality is there are some jobs where it can be talked about all the jobs that AI would create, but there will be jobs that AI take also as well. So I was talking to a bank and they said, AI has gotten to the point now where we used to have 90 people reading checks. we only need five. That's 85 people out of a job. We, we trained about half of them and we skilled them into other positions, but half of them, ⁓ whatever reason, there wasn't a fit. They didn't want to be retrained, ⁓ took the buyout. and decided to leave. will have an entire group of people for doing that. And organizations will adjust. We will redefine what entry-level job means. We will ⁓ them. We will give training around that. But think the thing is, as an organization, is to have a roadmap of how AI is going to be used in your company, lay out as far in advance for people so they understand how their jobs will be impacted. And the responsible way to deal with that is to say, your job is going to change in this way. It may even not be here. And this is what we want to do with you instead. IKEA, when they put in their new customer chatbot, 8,500 people were impacted. But instead of just laying them off, said, you know so much about our company and our products. We're going to retrain you to become design consultants. And we're going to open up a whole new revenue area where going to just be design consultants for people and they generate a billion dollars in revenue. Now that's a new way of thinking strategically and reinventing what business you are in and preserving this incredible asset that you have in people ⁓ saying, ⁓ am just going to write this down as an efficiency play. I think you win with AI by just doing that. You win by ⁓ not doing the productivity, but also then saying, What else can we do now with this combination of the technology and these incredible people we have in our organization?

Gwynne Oosterbaan: So that IKEA example, that case study is really exciting. I like dying to know if those people who preserve their jobs and opened up a whole new kind of career pathway for themselves, did they find more joy? So our podcast of joy beyond the job, like that seems like a really amazing way to give people a new, not just a lease on life and like a new way to think about work, but like, how do we know if they're actually like thriving? It seems awesome, but do you know more about that story?

Charlene Li: I don't know, but I think first of all, they really enjoy working with customers. And again, we think about jobs as getting paid for doing a certain amount of work, but there is tremendous psychic income that comes from knowing that you are contributing, that you're making an impact, that a validation of the value that you create. And so people, some people are saying, well, you should just have universal basic income for people who are impacted by it. I go, that doesn't replace. that intangible aspect of work. People want to work we want to be contributing members of society. So how do we do that in a way that is gratifying, rewarding, ⁓ also just preserves the way our economy works? ⁓ AI is going to take over a lot of the production, but people don't have a way to make money to spend on the products that AI is making, the whole thing doesn't work. So ⁓ need to figure this out. as organizations and as a society. And I think a lot of it again comes down to organizations thinking much more creatively and imaginatively about what that future could look like. And it requires leaders to think about change. Let's circle back to this. we only look at efficiency and productivity and we don't look at customer engagement and especially looking at reinvention, then this is not going to help us be And I think our goal here is to be better with AI, not just more efficient. That's not very inspiring. It's not very motivating.

Alison Woo: So your book, well, your book is about this 90 day plan. So let's talk about what's possible in 90 days, truly.

Charlene Li: not saying you're going to have a full transformation in 90 days. That's what I'm talking about. ⁓ But should be able to create a roadmap that shows you how you would create value with AI over the next 18 months. And you're that over 90 days to focus on your strategic outcomes that you want. One leader I was talking to recently said, ⁓ we have seven objectives. The first six are your usual suspects, ⁓ revenues, or these Number seven is use AI to accomplish the first six. And I think that is the perfect example of how to think about AI. It isn't a separate strategy. It's in service of your existing strategy. And so over those 90 days, you're figuring out what is our strategy and how are we going to use AI to support that? Do we have the people, the culture, the technology, and the governance to execute on that? Who's our leader who's going to be waking up every single day and saying, I am accountable for driving value with AI in my organization. Do we have a responsible and ethical AI policy? And so the blueprint takes you through each of those steps that you need to have at least an initial idea of how it works. And then you're just constantly iterating on that. I like to say, and some people say, that's insane having an 18 month roadmap. Things change like by day. How do you have an 18 month roadmap? Michael, the strategy may be written in ink, like where you're headed, long-term vision, but the roadmap is written in pencil. You can adjust that and be actually built in a quarterly adaptive review where at the end of every quarter, you're looking at that roadmap for the next five quarters, making adjustments, and you're adding another quarter. Because AI transformation does not happen overnight. You need to be thinking about where you want to be. in the future and taking the steps today to make that a reality. But if you're only looking at a quarter, you're not going to do anything strategic. We're just going to do like, okay, are the bushfires that I have to put out ⁓ being strategic and saying, how am I investing today for what I need to be doing 18 months from now?

Alison Woo: Just back to the idea that AI will do some of the redundant predictive work and we will leave us for more time with joy. How has AI helped you in your life, personally and professionally, leave more time for joy and what are you spending that time joyfully doing?

Charlene Li: We actually talked about this in the very last chapter, chapter 12. We talk about this idea of superhumans, where we have integrated intelligence, where AI is doing a lot of that heavy lifting, the tedious data intensive repetitive work. And that, we could just say that frees us up to do things, but is it freeing us to do more work? Or is it helping us be more human? To do the things that AI can't do. So we talk about being more empathetic, to have self-reflection, intuitive. judgment, wisdom, and I would love to add joy into that. How do we, because joy is something, it's an emotion that AI can't experience. But I'll give you an example. It sounds so silly, but in so many ways, it created such awe and wonder in me. I had to create a script for a webinar that I was going to read off a teleprompter, and it was all ready and everything, and then I'm practicing it, and I'm realizing, It doesn't sound like me. So I said, AI, go and find examples of me speaking and change the script to match the I speak, because I can't write the way I speak. And it came back, I'm like, ⁓ this sounds so much like me. couldn't be me, but AI could be. And that was ⁓ a revelation to me that I'm like, wow, AI is helping me be more me. And that was, you know, to be, to help me. express myself in the way that I would normally be, but I could never have done that on my own. So that was a bit of awe and wonder and joy to realize that I could be a better version of me in that moment.

Gwynne Oosterbaan: like AI as the mirror and the coach at the same time like reminding you of what you've already said and just giving you permission to do it, you know, because it kind of packaged it in this I'm always thinking that AI packages things in a beautiful way like ⁓ you could just do all my formatting for me.

Charlene Li: Yeah. Yeah, it's. what's great is I feel like I'm talking to myself and it's me and it's a better form of a stock is remembers everything reminds me of doing things ⁓ just helps me again be the better person of me and get it's not as far from perfect and I'm still working on this version of it but it's helping me every day I have a briefing from my AI that lays out for me every day and it sends me reminders of things. and checks in on some of my intentions and helps me my values better. So just like all these things that ⁓ not disciplined to do myself, but my AI helps me do that.

Alison Woo: Charlene, where can people find out more about you and get the book and connect with you where you are?

Charlene Li: You can find the book at winning with AI book.com. I am on LinkedIn. So please follow me there and engage with me there. And my website is charlineli.com.

Alison Woo: Charlene, thank you so very much for writing the book, helping people kind of figure out what's next in this world, but it's certainly going to be ⁓ a very interesting evolution.

Charlene Li: Thank you so much for having me

Gwynne Oosterbaan: Thank you so much.

Alison Woo: Okay, ⁓ Gwyn, what's your thoughts? to It's a super hot topic, this AI impacting the world, and now AI impacting joy. I don't think we ever thought of it that way.

Gwynne Oosterbaan: No, sure not. I love this idea of the psychic income that IKEA was so Scandinavian and thinking about we're not going to get rid of all these people because we introduced a chatbot, we're going to figure out how to re

Alison Woo: Yes.

Gwynne Oosterbaan: I don't want to say use, but how to reintegrate them into a different opportunity. And so that idea of creative long-term planning, I love that she said, you can't do anything in a quarter that's strategic. We need to hear that in every corporate boardroom. In a way, AI is forcing people to think on different timescales. And I loved that insight, both the psychic income and the way you think about time and planning.

Alison Woo: Well, this idea about the psychic income is a really important one because that is where you will get your joy, right? This idea that it's beyond money. You work for beyond money. You work for these other intangible and joy is one of them and the satisfaction of doing a good job and working with your colleagues and all of that. And then the idea that there is a separate contract, right? That companies have with employees. that they are not meant to be fungible. So if you use AI as the, is an efficiency cost, this is an efficiency play. and not think about the time and knowledge your employees have about your product. not use AI to be the bludgeon to say, well, this is why we're cutting off X amount of people. The key examples are really great one of them valuing their employees and saying, how do we take that great knowledge and help them redirect that in a new way that could be even more profitable ⁓ more enjoyable!

Gwynne Oosterbaan: That is the joy at the job, I think.

Alison Woo: Absolutely, right? We've always been key to that just because we talk about, you know... zest for more. It's not about leaving your job. It's about also infusing your job with more joy. And how do you do that? And you do that when you're passionately doing the thing that you love. And I mean, my personal hope is that AI will take out the repetitive, boring things that nobody likes to do. I remember as a journalist, we used to transcribe tape by sitting and listening, and it was the most tedious thing you can imagine. Now your iPhone will save a voice memo and give you an instant transcript before you have to do anything. I mean, this is really, you've saved two hours of your life. You were never getting back again.

Gwynne Oosterbaan: Yeah, for sure. mean her comment at the end about how she's using it as her daily Like almost meditation here's what you got to do. This is your intention. That is very meditation focused To keep her accountable and also to free her up to think I get you know outside of your immediate tasks of the day. I thought that was really By ⁓ eye opening was like, I've never thought of using AI that way ⁓

Alison Woo: But I do think she's really right because lessons learned from digital, right? You really can't think about how to use digital or transform your company using digital if you're not a user yourself. I remember doing this for many years, people who are not texting, using Facebook. And that's a badge of honor to say, I'm not on those tools. It's too late for that. Like you really need to, if you want to think about how to use AI, our colleague Mike Presson was my great example of like, I use AI for everything. He uses AI for, you know, complex, you know, different of information we would come across or how to promote his band ⁓ or how to a rec room or a man cave. I mean, there's so many different things. I was doing it for container gardening this weekend. Like what plants should I put in my container garden? really do, in order to be fluent, it has to be part of your everyday. And you start seeing amazing things like how to make better slides and how to do analysis and forecasting. And then you can start really imagining what it could really do for you.

Gwynne Oosterbaan: Yeah, no, for sure. It was really eye opening and I just wish we could have dug into the whole idea of creative. how do you help leaders think creatively and get them out of the trap of thinking that it's more just the efficiency. So maybe in next time we talk to her.

Alison Woo: ⁓ there'll be more. be much, much more. So is it for this episode. Please join us now in our newly launched YouTube channel, which is youtube.com slash @ zest for more, or you can visit our website zest for more.com or pick us up on Apple or Spotify podcasts, anywhere you get your podcasts. What a great conversation. More to come. Gwynne, thanks so much. ⁓

Gwynne Oosterbaan: Thank you, Alison. ⁓