Jill Reilly: Your AI Strategy Isn’t Enough

0:00Got your AI strategy or you want one. Do you have an AI culture? Do you have people who actually feel in live and by this, who feel interested and engaged with the ways in which it can help you grow your business, or are they sitting there actually really afraid that it's about to replace them? Welcome to Start With A Win, where we unpack leadership, personal growth and development, and how to build a better business. Let's go! Coming to you from Area 15 Ventures and start with the Win Headquarters its Adam Contos with Start With A Win. What are the rules you've been following your whole life about work, success, and how to live, we're actually written for a world that no longer exists. My guest today, Jill Riley has spent 30 years on the front lines of change, from post-apartheid South Africa to AI era classrooms, helping people break out of outdated systems and rewrite their own scripts. She's an author, a global change strategist, and the creator of something called the Ten Permissions. Jill, welcome to Start With A Win. Thanks Adam, it's great to

1:05be here. I'm looking forward to this. This is going to be a fun conversation I think, and our listeners are really going to enjoy this because we talked to a lot of entrepreneurs, we talked a lot of solo pernurs, and it seems like that type of human being has to give themselves some really, really deep permissions to take chances, to go places they've never been before. So I really want to jump into that, and of course, you have a book called The Ten Permissions. Let's step a little bit back because we all had to learn things in order to get ourselves to where we're at today. Where have you been and where have you come from and how did you get to where you are? Well, I'm originally from the States. I grew up in the Midwest, born in St. Louis, and went to University in Chicago and kind of started to get interested in change that was going on in the world. So it was way back when 1993, South Africa was on the cusp of its first democratic elections.

2:08I was bright-eyed. I was wanting to change the world. I was sitting in Chicago going, that's where I want to be, because I want a front row seat for a social transformation. Like, is it possible? Can they do this? What's it going to look like? As you can imagine, much to my parents, Shagrin, I graduated from Northwestern University and came because I'm based in Cape Town. I came to South Africa thinking it was six months. I was going to be here. I was going to help people prepare for the election. I'll be here for the election. I'll go home. I got hooked. I'm still here. There were a little, you know, I talk about in my book going astray. I have gone astray. I have been in many places in between here. But yeah, I'm still out in this part of the world and I'm still working on themes of transformation and reinvention and how we navigate profound

3:10change in our lives, in our businesses, in our communities. That's kind of been the subject that's you know, been driving my career since way back when. Wow. I mean, the world has rewritten the rules quite a few times over the last 30 years. So what? Yeah. Obviously, the whole post-apartheid situation, that's probably one of the largest rules being rewritten. And now it's fascinating to watch those changes happen. What do you think has been the biggest impact on your life when it comes to these rule reconstructions? Yeah, that we don't name the unwritten rules, right? We don't name sort of the conditioning that got us to this place. So, you know, while South Africa was busy reinventing itself, it created this beautiful vision of this new South Africa. And it hoped that that vision would be the driver, right? That people would see it and be inspired by its boldness and by its inspiration and it's

4:13kind of ethical grounding. What it knew it had to contend with, but what I don't think it necessarily contended with all so much was the history of, you know, human conditioning that had created the apartheid system that had gotten them to that place. So, you know, I kind of describe it as a whole lot of unlearning that has to take place. And that's a piece of change that I think we often miss when we're in these, you know, moments that profound change that we've got to unlearn the own rules. And then we've got to using my language, give ourselves permission to write new ones. And, you know, that's a piece of things that often gets lost. And, you know, when we talk about the book and where we are right now, I think it's equally relevant today in a world where, you know, the rules are being rewritten around us right now. And we've got to unlearn the old ones, allow ourselves to write new ones and then decide collectively how we move forward.

5:14I love that. And you talk about look for the right fit rather than fitting in. That seems pretty appropriate here. How can we take that today? Let's say we're running a business or something like that, you know, we do get stuck in our ways because it becomes comfortable. And I guess we have to get comfortable being uncomfortable, right? I mean, yeah. How do you approach that thought? Well, I think a lot of us, I mean, you'll hear me talking about conditioning a lot, but you know, a lot of us are conditioned to look around for the opportunity, look around for the role, the job, you know, and fit into it. And that worked for quite a long time, you know, when there were ready made roles in stable systems that, you know, I become doctor, I become accountant or I sell bread or. And so we had more fixed identities that, you know, shaped our sense of who we were and who we were allowed to be. And part of the discussion of the book is, you know, that fix itness is becoming much more fluid. There's more opportunities emerging.

6:19The old opportunities are disappearing. So it's not so easy to just look around and go, I'm going to be that or I'm going to do that or that's who I am and that's who I'm always going to be. So we need a much more sort of adaptive, you know, almost vendors mindset. I talk about the world right now as a marketplace. You're putting your stall out and you're constantly getting feedback about who wants what you have to offer, who's out there that you might be able to work with cell to. It's a much more responsive adaptive approach that's required in a world that's changing as quickly as this one is. And the point of the book being that if you don't sort of embrace that way of operating, you're going to miss out because there's lots of opportunity right now, but you've got to give yourself permission to operate differently in order to take it. That's, I mean, I think it's been true to my life also. You and I, you know, as I haven't been through what you've been through with, with a, you know, exploring some of that social change,

7:20but you know, leaving a government job after a decade and going, gosh, I have security. I'm going to go to not non security here pretty quick. That's a, that's an interesting thing. But and I love all the little takeaways in your book. You have so many little takeaways, you know, the whole I can is greater than I am. I think that one hit me really hard because it, it keeps you from getting stuck. Right. Right. Well, you know, the editor asked me to envision a reader. And although there were many, my, I eventually left on to my elder son who's 18. And I envisioned him now on the cusp of university and a career kind of, I don't want him to be searching around for a fixed identity right now because that's going to limit his potential to take advantage of this world. I want him and I tell him, you know, you've got a backpack on and you're filling it with skills and experiences and capabilities and you're heading out into the

8:21world with that backpack full of I can. And you are showing up as you just referenced looking for the right fit, looking for the ways in which what you can do serve somebody else out there. Um, that's the mindset that I want him to take into the world, not I'm going to get an accounting degree and become an accountant for the rest of my life. It's okay, fine. I'll learn accounting. And then I'm going to have to go and figure out what I can do with that in a world who needs it, why and where. So yeah, as you say, I can versus I am, frees you up to be more responsive and adaptive. And as I've said, that's the whole cut through the book. I hope you're enjoying these conversations and finding value in them. If this episode challenged your thinking, encouraged you or gave you a tool you can use to become a better leader, share it with one person who needs to hear it. Leadership isn't learned alone is passed from person to person, conversation and conversation and action to action. If you're listening on a podcast platform, I'd be grateful if you'd leave

9:25a review also. If you're watching on YouTube, make sure to subscribe so you don't miss future conversations. And if you have a question, a thought or a topic you'd like to see us cover, leave a comment please. I read them and I'll do my best to respond. Thanks for being part of the start with a win community. Keep learning, keep growing and keep leading. I mean, you talk so much about future readiness in this and and be honest here because you've worked with a lot of different leaders. Are most leaders actually ready or are they just really get a pretending they are? I'm not even sure they're good at pretending. I mean, if you look at the statistics, there's a massive migration out of corporate leadership right now because I think they're looking at the next decade and going, you know, they're standing on a threshold of something it's not hyperbole to say it's somewhat unprecedented. What within our lifetimes, you can't compare this to the internet, you can't compare this to anything of the last 20 years. So no, they're not ready. How could they be?

10:27You know, and I think that's part of what I'm trying to do with the book and the theme of permission, which is instead of pretending, as you say, that you've got the answers that you've got the plan, that you've got the strategy, let's go, maybe if we own a collective sense of, hey, this is a threshold moment and nobody knows what's happening. So what becomes possible when that's your mindset instead of quick, let's come up with a plan so that we can all pretend we know what we're doing. So no, they're not ready and I think it's time for us to acknowledge that and work with that, not from a position of weakness, but from a position of cool. Okay, so what do I need to learn? How do I need to respond? And that's tremendous pressure on leaders who probably spend their whole careers feeling like they had to have all the answers. But I think there needs to be a social conversation and it's part of what I'm contributing to around, it's not feasible anymore. We've got to operate differently as leaders and business owners and admit that this is uncharted

11:30territory and we're learning quickly as we go. Are you seeing something, a commonality that you're running into as far as a wall with leaders? You know, is there a common resistance point that you've cited in, you know, the 10 permissions or is it, I mean, it seems like, you know, when you talk to leaders, there's there's some message that's on replay with all of them. Are you seeing something in particular that's jumping out to you? Yeah, and it's sort of, actually, I just wrote about it today is the common reach for the strategy. I need the strategy and it's part of that, you know, in moments when everything feels overwhelming and uncertain, you want to reach for certainty before you've actually earned it. You know, so everybody's racing around right now trying to get those ideas on paper, trying to have the best shiny because they think that's going to be the thing to solve the problem and I keep going back these days to the good old culture eats strategy for breakfast. Like, and I'm telling my clients like, okay, yeah, fine, you've got your

12:34AI strategy or you want one. Do you have an AI culture? Do you have people who actually feel in live and by this who feel interested and engaged with the ways in which it can help you grow your business or are they sitting there actually really afraid that it's about to replace them? So I think the, the wall is if I have a strategy, it's going to save me and that's where I'm afraid we're going to run into a lot of problems. Interesting. Yeah, it's like we try and put some sort of a rule set down with our strategy and ultimately we're just blocking out the things we don't want to do. So, and the things we don't know that we actually need to learn and explore and spend just a little bit more time, you know, I also speak about it right now as a lot of people kind of coming at this moment with this efficiency mindset of like, okay, cool, how do I, how do I do this better faster? Whereas I want to encourage a kind of, you know, growth of what's possible?

13:36You know, when that's the starting point for the conversation, well, you have a totally different conversation, don't you versus cool, how do we use this to just cut costs? No, they can coexist, they should. But, you know, if you're just looking for shortcuts and simplicity and, you know, ideas that you think are going to be a box checking thing, this is not a box checking exercise, this is something much more foundational. I love what you said about, do you have an AI culture? I want, let's dig into AI a little bit here because it, it seems like every other sentence or every other conversation we have is about AI, particularly with leaders. And I'll be the first one to say, you know, I love utilizing it. I think it's, it's a fantastic way to explore new perspectives in business and operations. Tell me, what is your perspective on AI? And then let's kind of walk that path together of how can we build it into our culture a little bit more than we have? Yeah, well, I mean, it's quite clearly one of the most revolutionary, disruptive,

14:44technological forces that we've encountered. It's a generational technology that's fundamentally changing what we think is possible. It's, it's rewriting our understanding of human value, it's rewriting our understanding of intelligence, it's rewriting our understanding of what we need in a workplace in order to thrive. So, you know, it's asking us big fundamental questions and I think because of, you know, everything we've dealt with for the past five to ten years, we're tired right now, right? Like, I don't know a lot of people who are open to a lot of big exploratory thinking if they've, you know, sitting in Cleveland or Nairobi or anywhere else. It's like, goodness me. So, I think, unfortunately, you know, people are looking for quick ways to kind of weave it in and move on. And I think we're missing the opportunity here. It's also an incredible mirror. You know, it's an incredible mirror once you start bringing in of, of who you are, of how you treat

15:44learning of how you treat the new and the novel. And, you know, there's data. It's like a, I see it as a mirror giving people feedback to them about your own culture. And the reality is to get the full value of it. You need quite an exploratory culture. You need a place where people can ask questions, throw out half-formed ideas, challenge the status quo, run small experiments. That's not how most corporates are baked. They're baked to execute on plans and keep doing the same thing over and over. So, the strain that it's putting on cultures and people is that to get its full value, you've got to play around and be inventive and adaptive, really. And using my language, that's not most people, how most people feel allowed to behave in corporates. So, you know, I think it's requiring of us something that has previously not been allowed. And the,

16:45the winners are going to notice that and work with that from a culture perspective. And they're going to have people who know how to use this tool to keep growing over time versus people who know how to use it as a shortcut for what they don't want to do. Yeah, it's interesting when you take a look at different businesses. First of all, the first question I always see arises, who owns this? Right. And I think that's the wrong way of looking at it because everybody wants to own a project in a company or something in the nat nature, as opposed to, like you've said, how are we integrating this into our culture, which means it's the environment that we're operating in. It's how all of us agree to try things instead of just, you know, who owns this hammer? You know, let's go find some nails to hit with this hammer. And that's really not what AI is. It is, it's where you live. It's how you, you know, conduct your day, things of that nature.

17:48How have you seen anybody really successfully harness this and and implement it in their culture and your your consultation with different businesses? Successfully, you know, I think it's early. I see people who I think are going out of the right way. As you say, not to treat it as a project you own or just a tool that you implement, but, you know, a growth, accelerate. Like so for me, as I said, it's kind of how you approach it and how many conversations are you willing to have about it and not have an answer that arrives to, okay, fine. So, you know, now we know what we're doing. Cool. Let's go. So if you allow yourself a period of exploration and experimentation and one of my clients had a, you know, a sort of game, if you will, of, you know, come, let's come up with what we could do with it. And I like conversations that framing framed around what are we going to build?

18:50What are we going to create? You know, come at it with a builder's mindset, a generative mindset of what does this allow me to do? What does this make possible? Those are four great questions to frame conversations that don't have to arrive at an immediate product and immediate solution. And the ones that I know that I think are ultimately going to really see this as a tremendous growth lever are the ones who are doing that and allowing their teams to play around to engage in an exploratory way with what's possible to try and fail to do things in a half-bake manner and not get judged. And that's, that's for me to bigger or lesser degrees depending upon what your culture can handle, the approach that I think you need to take. But when you are racing through it and treating it like, okay, you know, we need a plan, we need an answer, we need an implementation roll out,

19:54you know, you're going to do the easiest, most familiar thing. And that means it's going to probably undercut your capability rather than enhance it to the extent that it could. I love that. You know what's interesting is, you know, in listening to you, we talk so much about AI and corporate environment, things like that. You mentioned AI in the classroom every now and tell me, you know, how we need to be, you know, bringing our kids up. Now they're, we hear digital natives, things of that nature with, you know, like millennials were digital natives or Gen Z. But how are we creating AI natives now when it comes to kids? Is that something that's, is that a real thing or what do you see it from your perspective? Yeah, I think it's a real thing it has to be. I mean, you know, in my work, I talk a lot about doing remarkable things at points of reinvention. And I've been lucky enough to be in countries and with people at a point when they were really on the

20:56threshold of fundamentally rethinking how they operate, who they are. And I don't see a way forward that doesn't involve some fundamental rethinking of how we educate children. I mean, they can't be, because intelligence now has been redefined, right? So the ability to acquire and regurgitate information and be judged through a lens of right or wrong, you know, so the shift now moves from accumulation of knowledge to use an application of it. It, it moves from, you know, your ability to kind of memorize and understand your ability to effectively use what's already out there. So I think we're looking at a shift, you know, I am a big agency geek. I talk about it all the time because for me, it's, it's such an under explored concept around, you know, human empowerment that we need young people who feel allowed using my language to take information and apply it in all

21:58sorts of different ways. Are we there? Sorry, Adam, you froze. Oh, yeah, you're, I'm here. Okay, sorry, you completely froze and I was worried that we'd cut off somehow. So yeah, I think that what we're looking at is a decade of reinvention of education and the classrooms that I'm entering into. I think there is, you know, a lot of fear and uncertainty around for teachers, for administrators, for everybody who's entire way of living has been shaped around an old model to understand what the new model looks like, but it certainly is coming. And I think the question is how, again, how we begin to explore and experiment and move in that direction. Fascinating. Yes, I totally agree. I mean, it's the day of, hey, everybody get out your textbooks. Is pretty much

22:58gone. Now it is, break out the computer. Let's get into AI and talk to it about this. So, I mean, it's, it's very much game changing for how kids are learning and how society is evolving. So everybody, this is a fascinating conversation with Jill. Make sure you check out Jill at her website, 10permissions.com. The book is amazing. It really, it causes you to hold up the mirror and find out where can I expand my thought, my process, my future. And the permissions are very much obvious to you, but have been hidden in your life. So I love how Jill has, has developed this thought process. Check it out. Jill is also all over YouTube and the internet. She has a lot of great information out there. Jill, I have a question I ask all the great leaders on this show. And that's how do you start your day with a win? I go for a walk. Like, again, I think for me,

24:04making one conscious decision to get myself out into the world is a win. Because I think it's super easy to just drift into work and desk based and in my head and in my house. And I think for me, that is just critical time to kind of reengage with myself in the world. To remind myself of the beautiful world that's out there in my ability to move through it. And I always come back feeling lighter, clearer, more energized, more capable. And I think that somehow just making one simple choice to do something you want to do that takes you out into the world in whatever way shape or form that might be is my definition of starting with a win. What a great way to start your day. That's fantastic. Thank you. Jill Riley, author of the 10 permissions, global change strategist. Thank you for being with us here on Start with a win. Oh, such a pleasure and I'm saying so was a great conversation. I appreciate your time.