Simon Waller (00:01.998)
Hello and welcome to episode 10 of the Future With Friends. We’ve hit double digits and today I’m being joined by a very good friend of mine and someone I’ve actually worked with for a very, very long time, the incredible Leanne Williams. Welcome Leanne, thank you so much for coming on the show.

Thanks Simon, it’s good to be here.

It is good. Now, the reason you’re here though is a little bit, it’s interesting in and of itself. Cause basically you were dared to come on the show. Is that right?

Leanne Williams (00:34.176)
challenge was set for me to do a podcast. So yes, I reached out to you and it as we were just chatting, it kind of forms a little bit of the basis for the scenario as well.

Yeah, so you’re doing some work with another friend of ours and a previous guest on the show, Michelle Newell. And Mish basically set the challenge. But interestingly enough, you were actually on my list anyway. I have a list of future guests and staff and I think you just got elevated a few spots. And I was like, oh, how cool that people reached out to be part of it. Because 100 % you still hit the brief because this is the future with friends and

As much as a lot of our relationship has been a professional one, think I still very much deem it has been a professional friend relationship. I hope this is not news to you and that you feel similar.

Yes, my friend Simon.

Otherwise we’d have to cancel the recording right now and move on to a new guest. And do you remember how we met?

Leanne Williams (01:37.144)
Yeah, I’ve actually been thinking about this because I’ve been listening to these podcasts and I’ve been most recently listening to the one with you and Jason Fox and actually how I got your name was through Jason. So I saw him speaking up in Albury once and he gave me your name. So I was then trying to think about, pretty sure I reached out, we had a chat on the phone when I was working and living up in Bright. So…

But then when I came down to Gippsland to work for West Gippsland Libraries, I reached out so that we could work together.

I think we ran into each other again before or after that. There was another event that Jason ran in the city and I remember running into you there and I can’t remember if that happened before or after because you reached out to me when you were at Alpine Shire and then I think you left like a month later and it was then you went to… that’s right. It was like, hey, you should come and work here and then I’m gone.

Yeah, but I know that, like there’s been a few events that I’ve seen you at, but there was one, I’m not good with Melbourne suburbs, but there was one, and oh, I can’t remember. I remember seeing you at an event, but I know that we had already met and worked together, so I think that was like a few years later. So the one that you might be thinking of.

Yeah, all I gonna say was I remember being upstairs in a really cool bar, as I said, but then again, that could be anywhere in Melbourne.

Leanne Williams (03:10.008)
Yeah, I think that was after we’d already done the first bit of work.

Okay, yes, we work together at West Gippsland Library Corporation. then over the last, I suppose, three years or so, we’ve or four years or so we’ve worked together heaps. And in that time, both I suppose, technically, you’ve been my boss.

when I’ve been consulting back into MYLI and then I got to be your boss when I joined the board and then became the chair. And so yeah, we’ve had a beautiful working relationship. And in that time, as much as that’s been a professional relationship is one where to me, I’ve also really enjoyed the conversations, almost like lot of the side conversations that we’ve had along the way. We have a tendency to kind of speak when we’re on long car journeys, which

if you’re based in kind of Gippsland, happens a lot. And yeah, it’s been a really beautiful, it’s been a beautiful experience by working and building this friendship with you. And now here we are on the podcast. I there’s anything that we could do to cement a friendship, it’s to do this.

Simon Waller (04:18.55)
It doesn’t get more real than this, Okay. And now you mentioned also that in some ways the dare that you got given by Michelle to come on this also feeds into the topic that you have chosen today for the future. Now, I think we have made different versions or different titles for this. What’s your version of the title of this episode, Leanne?

Fuck.

Leanne Williams (04:48.014)
I’ve got some words, but I’ve probably changed them. for me, it’s about risk and it’s about discomfort and leaning into that. I think more about, it’s about my, the idea came from me being.

bit crazy with my mountain biking and people really having this view when I speak about what my hobbies are, people will be like oh that’s that’s a bit crazy but I don’t see it as a risk in the way that other people do.

Yes. So when I, I think my interpretation of it was the future of doing stupid things. And although, well, okay. this is the, this is, mean, kind of look at it. Well, what is that? I mean, even when we started talking about this topic and I was thinking about it and ruminate on it myself, I was kind of like, well, what is the difference between riskiness and stupidity? Because

I’m not gonna say that about myself

Simon Waller (05:57.262)
In some ways from the outside, they look like the same thing. Do you know I mean? Like the type of behaviour that we would describe as being really quite stupid behaviour. So like say jumping, like cliff diving for instance, to the outside observer looking at people who dive off cliffs. You go, wow, that looks really stupid and it’s risky and it’s also courageous. And so it’s almost like our capacity to assess these things from the outside is difficult.

So my interpretation was the future of doing stupid things. And not, but not look through the lens of that being a negative, but almost like this idea of, you know, how, how is it that we can do things where we’re willing to risk ourselves and, challenge, challenge ourselves without knowing exactly what the outcome is going to be.

Yes, but I think it’s also about perspective. So something that, as you said, looking from the outside in can look very risky or stupid. I took the opportunity in this scenario or what spawned the thought for me was around if I use mountain biking, I don’t see it as risky in the way that others do. It’s about your level of comfort, but it’s about how we challenge ourselves to make sure that we do step outside of our comfort zone and how we can do that.

when we do find ourselves getting too comfortable.

All right, so we’re gonna jump into the scenario in a little sec. So tell us though, you’ve set this at some point in the future. What’s the year do you imagine that this future plays out in?

Leanne Williams (07:33.582)
2049.

And is there some significance of that? we’re talking 24 years from now. What is it about 24 years from now that matters to you?

It’s not so much that that year specifically matters. It was more around how long does really subtle changes take over a period of time to have a significant impact. So really small ripples over a long period of time. If you’re then in 2049 and you’re looking back, you would actually see that’s quite a significant change. But when they happen in small incremental amounts over a long period of time,

change can sneak up on us and it doesn’t feel like change.

Yeah, so I think there’s a Bill Gates quote that said something along the lines of we will always overestimate how much we can achieve in the short term and underestimate how much we’ll achieve in the long term. And it’s almost like that is compounding impacts of change. And it’s almost like that is, yeah, what you’re suggesting is that the little small things in the short term don’t feel like much. But when we look back from the long perspective, actually, we see a lot that we can shift cultures in a meaningful way.

Simon Waller (08:44.142)
And not in this case, when we look at this scenario, potentially not always for the best, which is cool. And I think just to add to that as well, I think that when we kind of talk about this from a scenarios and a futures perspective, like certain things change slower than others. So technological shifts can be quite sudden, but cultural shifts do tend to take longer. So we can actually, as you said, imagine quite a significant cultural shift within society when we start to look at that kind of 20 year horizon.

All right, is there any other context or anything you want to give us about this or do you use reddit to jump in?

I’m just ready to jump in.

Okay, well, the camera is all yours, Leanne. Please share us your scenario about the future of doing stupid things.

Leanne Williams (09:30.542)
Love it. The world had changed, but not in the way she feared, in the way she refused to accept. Go on, I’ll follow, she calls out, pushing her bike up the slope. You’re still allowed to do this, right? Her son jokes, checking over his shoulder. Did you disable the risk monitor? She laughs, but they both know he’s only half kidding. In 2049, mountain biking on unapproved trails without a state issued risk override permit is technically noncompliant.

But she’s never been one to outsource judgment on an algorithm. It wasn’t always like this, but the shift came gradually. First with school camps quietly canceled in the late 2020s, then came the mandates, mandatory risk assessments for all public activities. AI generated, behavioral alerts, a society so obsessed with avoiding harm that it forgot how to live. Now every smartwatch is a safety warden.

Every child wears a biometric wristband from the age of three. Walk your dog without a risk consent, warning issued. Ride a bike without a pre-approved route mapping, red flag. Share a controversial opinion, emotional harm risk elevated. Risk itself wasn’t the problem. The fear of being blamed for it was. It began with insurance data feeding generative AI systems. Systems that reshape not just decisions, but entire cultures.

Tech companies, under siege from litigation, defaulted their platforms to prevention mode. Any action without potential negative consequence, physical, reputational or emotional, was flagged, discouraged and eventually forbidden. The outcome, a society of brilliant minds, paralysed by programmed hesitation. A generation that could simulate every outcome, but no longer knew how to experience one. Her company had been on the brink.

Innovation stalled, strategic risk was seen as a negligence. Employees sought permission for everything and waited until one day she’d had enough. That was the spark for the graduate adventure camp. What begun as an underground experiment, a secret leadership immersion off grid and off record became something bigger, something bolder. It was more than mountain biking and obstacle courses. It was unlearning fear about recovering instinct.

Leanne Williams (11:54.25)
about reminding people that mistakes weren’t moral failings. They were the raw materials of growth. The program’s success spread like wildfire, even after the regulators pushed back. But it was too late. The tide had turned. That’s when the role of chief risk taker emerged. No polished credentials, no AI vetting. Just one question. When was the last time you took a risk and what did it teach you?

Now as she watches her kids disappear down the trail, eyes lit, shoulders relaxed, she feels something most haven’t felt in years, pride in doing something unapproved. A rider crashes further down and no alerts, no digital triage, just dirt, blood and laughter. You okay? Her son shouts. I’m alive, the rider grins. And in this world, that still counts as a radical act.

Simon Waller (12:48.194)
love it. What a great scenario. And I love how personal it is for you. I know that we have had countless conversations the last few years about your bike stacks. Though I think most of them been on road bikes, haven’t they, rather than mountain bikes? What’s the ratio of road bike stacks to mountain bike stacks for you?

for me, well, the ones that have serious injury, road bike is the one where I’ve had all of my serious crashes. So I think, you know, two head injuries in the last sort of six months, but I’m, the mountain biking, strangely enough, actually feels safe for me, which is part of, guess, what I mentioned before that it’s crazy how something that’s seen as so dangerous actually feels really safe for me. I only have low speed crashes on a mountain bike.

Yes, so this is super interesting. I love how personal it is. And so I almost get that in this scenario. So this is you talking almost in the it was in the first person where it’s basically you are doing this with your kids. So how old are your kids now?

Oh, now they are 9, 11 and 13.

9-11-13. So in this scenario, they’re going to be somewhere in their kind of mid-20s to mid-30s. Is that about right? Yeah. Yeah. And so I love that. I love the personal aspect of it. Can you tell us a little bit how, like where the inspiration came from? What may be some of the signals and stuff that you picked up on that fed into this for you? Like where did the, where’s the kind of the seed of this scenario in terms of what, where the Genesis comes from?

Leanne Williams (14:30.326)
Yeah, good question. I’ve got there’s lots of little signals. So one of the things that I talk a lot about in as a leader is around strategic discomfort and leaning into that discomfort and fear. And in terms of the brief that you and I spoke about where you encourage me to like come at this from a personal angle. I

I guess reimagine what that might look like, brought that mountain biking element into it, as I said, because it’s something that I don’t think is that particularly risky. But the other signals that I had seen, where I mentioned in the scenario about school camps, I’m already seeing that. So school camps are already being shortened. Unfortunately for me, I’d quite happily send my kids off for a whole week. So there’s this conversation around kids.

not wanting to go on school camps. And so I started to think about that from the point of view of what’s the impact of that on our children today, if there were no school camps and what the impact in the long term is. But the other little seed that I had was in your podcast with Megan Davis, when she talked about the actors, young actors coming through not wanting to experience that full range of emotion and that

you that’s a core requirement of being an actor and you talk about that 22 living life at 22 degrees Celsius. So they were all signals that came through where it’s, you know, gave me that idea around what could risk taking look like.

in the future. Yeah, I certainly felt a bit of that even in our conversations before this, but also in the scenario itself about how we’ve, feels like we have a narrower band of what is acceptable levels of risk now than when we were kids. And again, I don’t know if that’s some form of immediacy bias and we have like no perfect recollection. And you know, when I go the title of, you know, the future doing stupid things, my memory of being young was doing some really stupid things.

Simon Waller (16:36.884)
And it wasn’t in a calculated risk way in the way that you talk about it in your scenario. It was actually probably just stupid. you know, like stupid things like driving a car way too fast, then I should have, or, you know, deciding that it was a really great idea repeatedly to, you know, climb up onto people’s roofs and that would be the best place to drink beer. Or I think remember one time when I was like 13 years old, like…

deciding to ride my bike, head first into someone else riding their bike. It was almost like it was, I don’t know, some medieval jousting thing, but without the sticks. And it’s like all those things I go like, there was no, like they were not calculated risk taking events. They were just stupidity. But that stuff seemed to happen a lot. And I don’t know what shifted. I don’t know whether my

kids are just smarter than I was, or whether there’s actually, has actually been a genuine cultural shift in terms of behavior, or also, and this is a, I think that probably boys may be slightly more biased towards doing stupid things in their teenage years than girls. I’ve got two girls. I’m not sure that they’re wired in the same way that myself and my brother were.

Yeah, I grew up on a farm so risk taking was probably a bit more of the norm and so when you talk about those cultural shifts in society I actively encourage my kids to be taking these risks and I think that whether it’s the environment that we grow up in, like I said coming from a farm, know, I was constantly doing stupid things and so I guess there’s this line as a parent where you

want to make sure that you’re taking these risks and you’re encouraging your children to take risks, yet at the same time you are not wanting your kids to put themselves out there too much where they’re going to get hurt.

Simon Waller (18:44.812)
Yeah, I agree. think that the band of acceptable risk or acceptable stupidity has got a lot smaller than when we were young. And I know could just be like,

immediacy bias, know, immediacy bias is whereby the things that are happening now feel more real than what happened in the past. And somehow we think that our kids are not as cool or as risky or whatever, or that they watch way more TikTok or TV than we used to. But I did some crazy stupid things when I was younger. And I don’t even think I could describe them as being risky, because there was no calculation attached to it. It was just like doing things like

You know, driving a car way too fast down a suburban street or deciding that the best place possible to drink beer would be on, you know, my best friend’s parents roof and then somehow cut in an Esky up there and sit up there for a couple of hours and then trying to work out how to get back down again. Or I think at one point I did a jousting thing, like where my 13 year old, I just like rode my bike.

into somebody else’s bike. We didn’t have the sticks or anything like that. But like, again, no calculation whatsoever. Like there’s zero upside to be had here. It was all just pure stupidity. But I also don’t know as well like whether there’s a difference between boy stupidity and girl stupidity. Because I’ve only got two girls and I’m judging their behavior against the behavior that I had with my brother. And again, I probably may not even have been the stupid one.

Yeah, and I think I was definitely the stupid one in my family. So I think the boys girls thing, I don’t think it’s so much about that growing up on a farm. I grew up riding horses. And I would say when you talk about it not being necessarily a calculated risk, my mindset was actually more the opposite. It was almost like I actively thought about like what stupid stuff that I can do. And I would always be there was little

Leanne Williams (20:32.906)
minimal reflection that would go on. Sometimes I was like, that was a close call where I managed to, you know, not have a massive stack of a horse. But I think it links to the environment in which we grew up. And I look at my kids and think, I actively try to push them to take more risks so that they build that confidence within themselves. But I also, as a parent, don’t want them doing the stupid stuff that I did.

Yeah, and this is interesting, isn’t it? Like, I do believe that there is definitely a culture around risk management in organisations and even within our life that certainly evolved over the last 20 years or so or 30 years or so since we were doing that type of silly stuff. And I think that’s kind of partly what you’re capturing in this scenario. So maybe we’re going to jump into that a little bit and dive into a little bit deeper. There’s a couple of things in there that really stood out to me in the first

One is this role of insurance in terms of shaping the culture. And this idea that if this insurance data was ingested by AI and AI has been used to assess us and assess what is acceptable behavior, suddenly we could find the boundaries of what. So it’s two things. It’s what is insurable almost becomes what is acceptable, which I think is a really interesting dynamic.

Yeah, and it’s interesting when you talk before about what were some of the ideas or signals that helped with this. This is something that growing up horse riding, I’ve already experienced. So when insurance premiums back when I was a teenager started to go up, I remember that at all of our horse competitions, there was actually the introduction of insurance waivers. Insurance got too much, organisations couldn’t afford to pay it.

And every event you went to, you were assigning a manual piece of paper, this insurance waiver. So part of this scenario is actually exploring where you’ve got AI taking that to probably the next level or way beyond. But again, those signals have already happened in society. And if we would reflect back on how they shaped us at that time, I certainly remember it was all about, you know,

Leanne Williams (22:55.362)
don’t fall off, risk avoidance. And so we do have these periods where in society it gets a bit lumpy and we have big waves of risk avoidance, but then we sort of calm down for whatever better word and it sort of levels out, but then we’ll have another spike.

One of the lines you use in the scenario is this idea that she has never been one to outsource judgment to an algorithm. I found that a very interesting line. I know that you don’t mind a little bit of chat GPT in your life. And part of its strength in theory is in making these types of judgments. So,

we have a limited capacity as human beings to be able to take vast amounts of complex data and use that to ascertain a judgment. So we use a whole bunch of kind of cognitive shortcuts to be able to arrive at an outcome which can potentially be quite biased or inaccurate. And the theory of it is that AI allows us to actually take into way more data in a way more transparent way that we could possibly do ourselves.

So I find it very interesting that you would choose to actively dismiss it in the sense that it’s been kind of written here. What is it? Is that a, that a throwaway line or is that something that you actually feel at the moment in terms of your own use of AI?

Leanne Williams (24:29.582)
Well, I think in writing this scenario as an example where I actively did not want to use AI. So I resisted it. But then also the curiosity gets the better of you. And I did put the scenario in, make a few little tweaks. And I guess surprisingly,

I was happier for the purposes of the scenario with the AI version. But I think if you then take, it really depends about context because if you actually take about assessing risk, say in a mountain bike setting, for example,

you’re overriding, or my experience is, I’m overriding my own mindset frequently when undertaking the activity. So it’s not just about overriding AI from a future point of view when it comes to this scenario. You still have to consciously override your own mindset to actually make sure you’re leaning into fear because fear is, you know,

where your learning and development and growth happens. And if we don’t push our boundaries and we don’t step outside our comfort zone, well, you know, where’s the adventure, where’s the excitement, where’s the learning?

Mm. Yeah, I think that’s an interesting idea. This idea that there’s a space of fear, which is beyond the level of acceptable risk. However, we’ve calculated that. And that to actively seek out that space is a really interesting way of looking at the lens of risk in the sense that, yeah, we’ve still done the calculations and then we’re just going to go a little bit further. I do wonder though, like given your own personal experience, I know you mentioned it was more with road bike.

Simon Waller (26:22.894)
bike accidents. And I think the last time I caught up with you in person, you were sporting a massive black eye, because you’d come off a road bike and then you shared photos have been taken away in an ambulance. Yes. And yes, looks like, look, let’s look at it through like, there’s also an asymmetry that potentially exists in terms of that risky behavior. Like at the time,

I mean, you were just moving on from your role as the CEO of Miley and you’ve taken on a new role in a larger organisation. What you are putting at risk is substantial. Like you’re putting at risk, you know, the financial well-being of your family. Yeah. I kind of look at that and go like, you know, in terms of that risk assessment,

That’s a really good example.

Simon Waller (27:15.894)
the upside versus the downside aspect of that, like how much is at stake versus what is the benefit that’s obtained from the riskiness.

Also, to add to that is the risk assessment before and after the event. So going into that particular event, it was no different than any other bike race. mean, reflecting on it, there were a few differences, you know, more street furniture, more likelihood for crashes. But me going into that, I was like, I didn’t see that as any more risky.

But it’s not until then the consequence came to fruition, crashing, knocked unconscious, being taken away in an ambulance. But interestingly in that, and this is also a theme in previous crashes I’ve had over the course of my life, is that I guess it’s one’s view of how they view the world, how they view risk. And I’ve always had this element of optimism and…

It is what it is. you get back on or so people who ride horses, you just get back on the horse and you give it another go. But

I should write a proverb like that.

Leanne Williams (28:27.95)
It’s the status quo when you ride horses, you just got to get back on, you get fucked off all the time. people who… It’s the external environment that started to influence post-incident in this particular case. So, my family and friends, well, I really emphasise that the consequences could have been much worse and I should take the risk more seriously.

and I should take future steps to avoid finding myself in that situation. And at the time, it’s about taking in all of that information, assessing the risk and then making decisions for future activities. And I guess what I found with the passage of time after that was that the influence did start to creep in and I possibly may not participate in a race of that type.

again, because there has been a pattern emerging and maybe the risk isn’t worth the consequence whereby, particularly when it comes to head injuries, they could be much worse. And so then what does that mean for the rest of your life? So it’s quite a complex thing and there’s other people at stake. It’s not just me. Like you said, it’s the family.

think this is the thing that probably came up to be almost most clearly through this scenario was this concept of asymmetry when it comes to risk. So using the example of the bike race is the the risk of harm is immediate. The the benefit of the risk is long term. So the risk of harm happens in the race at that moment in time you come off your bike, you have a head injury, you end up in hospital. Like that’s an immediate risk. Like all of the cost is

born in the present. What you’re talking about though, in terms of the value of risky behavior, and in this scenario, you talk through it through the lens of things like innovation and, you know, in organisations as well. Well, that actually happens over the long term later. And it’s more nebulous. Like this is the challenge with a lot of stuff around innovation in organisations is how valuable is our innovation program going to be? And we’re like, I don’t know. Like we can’t possibly know because that’s the whole point of the risk.

Simon Waller (30:45.934)
And so I kind of saw that in this, like I saw that in the conversation you just had, but I saw it a lot through this scenario about this concept of asymmetry. I think it even plays out when we talk about insurance. So if you are an insurance company, your job is to insure against the short term impact of risk, i.e. you came off your bike and there’s an injury and you have to be hospitalized and taken the ambulance. The insurance company receives zero benefit.

from the ability for you to overcome fear and employ risky behavior inside a business later on to drive innovation. So you see like this asymmetry of like, they would obviously wanna drive you to not be risky, because they’ve got zero, they don’t get to partake in the upside part of this later on.

Yeah, and I think the, obviously, insurers are always trying to take that conservative approach because it’s about their bottom line, their profits. But I think what I also tried to push within this scenario is when we don’t take risks, innovation is is sacrificed. And when over a long period of time, there’s small

changes from a conservative point of view, like what would innovation look like in the future if we’re all completely risk averse? And so then what does growth look like for organisations? It really starts to dial down, or for me, it makes me feel quite sad. It’s like, where’s the excitement for…

that next innovation and what the future could hold. And I think there’s a little bit of that we’re experiencing now with when you take chat GPT, we’re in this phase of with the AI, it’s the unknown, every those who are embracing it, they’re really getting in and exploring it and playing with it. And then I know for myself, I get really excited about, you know, what it spits out and that’s great. But at the same time, there’s this conscious awareness of what are the unintended consequences? What are the things that we don’t know about now that are going

Leanne Williams (33:02.862)
that in our excitement in playing with it, and yes, innovation is great, but we still have to consider, I feel like I’m contradicting myself here, we still have to consider the risk about what those long-term impacts look like that we haven’t thought of, but making sure we can still achieve innovation and not sacrifice that.

Yeah, this is one of the interesting things I’ve done a bit of work at the intersection of futurism and risk management, because we use some similar language around how risk is identified and rated. But there’s also this kind of intrinsic differences. So we both often have a scale of impact, like how big is the consequence?

And then we have a scale that may look something like a likelihood or a probability. And in futurism, we use this idea of certainty, like how sure can we be that such a thing may happen? And it’s a little bit different from probability in the sense that with probability, we have the capacity to assess something because it’s happened before, because it’s happened a number of times, we can understand the probability of it happening again. Whereas often in futurism, we’re talking about things that have never happened before.

So we can’t assess a probability as such and they don’t fit well into kind of traditional risk management matrices. And I think that when you talk about some of the risks around artificial intelligence, I think that’s the challenge is the impact is unknown. The probability is unknown. It sits outside of traditional risk management practice. And sometimes that means we may just choose to ignore it then as opposed to actually managing it. Now,

In theory, this is interesting now when we talk about going back to your scenario around mountain biking. Because if someone has never mountain biked before, their ability to assess risk in that scenario is severely limited. Their fear is very, very high. If you’ve done a lot of mountain biking, your ability to make an assessment of the risk of a particular path in certain conditions and all the rest of it becomes, I suppose, entirely elevated.

Simon Waller (35:13.176)
And I think that’s kind of what you’re talking about in this scenario is that you’ve been doing this a lot and so the risk to you is less than perhaps is to someone else. One question I have to you though is, do you think that risk capacity that you’ve built is transferable? So given your ability to manage the risk associated with mountain biking, how comfortable do you now feel with cliff diving?

You know. So I think.

But there’s people who do a lot of cliff diving, right? Like, and they would be making their own risk assessments. And so part of this is that, you you talk about this ability to lean into fear and both of you are leaning into fear at some point. So it feels like something is transferable even if it’s not the same skillset and not the same risk. Like, do you know I mean? Like there has to be something that we can take from one to the other. Cause that’s also a core to the concept of innovation, right? You’re saying that the riskiness that I have the ability to take on in my personal life

is transferable into a business setting.

Yeah, I think it’s about, can’t, you saw my reaction to going to cliff diving, but I think it’s about, you wouldn’t just go and jump off the top of a cliff and do your first cliff dive. There’s going to be a process with which you dip your toe in the water. It’s like mountain biking. You don’t go to the top of the hardest, steepest run.

Leanne Williams (36:38.018)
and that’s your starting point. Your starting point is something much more tame, allows someone to get their comfort, and then you go from being uncomfortable and trying something new to building a level of familiarity, and that’s when you will able to then go, okay, right, now it’s time, I’m feeling comfortable, now it’s time to take that next step. And I think part of what I was trying to talk about or trying to highlight in this scenario is about we can’t lose

the opportunity or we can’t lose that element within our lives of making sure we’re continuously stepping outside of our comfort zone because I do see that happening in all aspects of my work, personal life, in society is that people are erring on the side of, that’s too risky, I might not try that. And so I will, you have to have a go. And I think it’s people don’t like that feeling of discomfort rather than actually thinking about

discomfort’s good. So we’ve framed it in a way that is in a negative. And I guess part of, you know, the way I go about things and same trying to coach my kids is that that feeling of discomfort is good and you’ve got to lean into it. And it’s just because the fear of the unknown makes us uncomfortable doesn’t mean we avoid it. So it’s not something to be avoided. It’s something that you have to lean into and try again.

Yeah, I actually think that’s really interesting, Liam, because I do think that a big challenge around this is the language that we use. So you talk about discomfort and you say discomfort is good. It’s actually really hard to imagine though, that discomfort is good because discomfort is something that is the opposite of comfort and comfort is comfort is good. And the same thing even when you talk about risk. Risk has a connotation attached to it, the language itself has a connotation that is something to be avoided.

not something to be embraced. Now anyone who’s done the AICD course knows that risk is an inherent part of reward. You know, that there is no, there’s no solution. There’s only trade-offs in this space. But do you think that the language itself, I mean, what’s the alternative to discomfort? Like how do we lean into something that feels almost like more positive?

Leanne Williams (38:53.94)
that’s a really good question. think it’s that feeling, it’s also a skill to be able to assess what that feeling within ourselves is like. So as you said, we’re wired to avoid it, yet we have to actually frame it through a positive lens. And I think it’s how, yes, you have to be able to assess the risk, make an educated decision around,

which way you go because as you said, strategic risk, taking risks is good and can lead to really great innovation. At the same time, we also can’t be stupid and we can’t just say, no, disregard that. I mean, and some people do. I think it’s about not having that avoidance feeling kick in and then want to take the easy road because

I think it’s a dialogue we have to continuously have to make sure that we hold each other accountable. We do lean into strategic risks and we take calculated risks. But I think sometimes we just get that nervous feeling within ourselves as an individual and don’t know what to do with it. And that takes skill and practice because if you’re constantly avoiding it, then that’s going to be the natural path you take.

But if you actually are self-aware and lean in and give it a go, I think a lot of the time people would be surprised about what the end result is.

There’s so many interesting lines in this in terms of what we perceive to be acceptable or unacceptable or good or bad. And I generally have a hesitancy about lines and binaries and like to think of things in spectrums. But if I kind of look at the flip of what you’re talking about is things like, you know, things like emotional trauma or physical trauma attached to these things.

Simon Waller (40:58.266)
One thing that came up for me a couple of times when reading your scenario was how comfortable are we though when the people die? I know that seems like a like a very dystopian view on the dystopian scenario that you put forward. I know you said this was the dystopian version of the scenario and I obviously saw a little bit to the other one as well. But in this one, obviously you’ve got a rider at the end and it’s kind of like but they didn’t die.

Simon Waller (41:28.856)
But that is, that happens in mountain biking. Yeah. It happens in road biking as well. It happens in all different parts of our life, but we seem to have this real aversion to people dying. And I know that that, I know in itself sounds weird, but first of all, we all die is one thing. It’s just a question of when and how. We often feel this need to hold on to old age as opposed to, you know,

going out doing something that we love, but we have a diversion around death and around injury in modern society, which I don’t know, like, on one hand, if it was my kids or me, I don’t want that outcome for them. But somehow, weirdly, even at that kind of collectivist level, there is this, I know, it feels like there’s a real tension there. Do you sense that as well?

I but I think if we pair it back a little bit and talk about a broken bone, for example, I think it’s about how we frame it prior. So if we, you know, I’ll think to myself around how do I feel about, you know, my son flying down a downhill track, knowing that dying is a risk, breaking bones is a risk, like

that there are a huge amount of risks, but I think sometimes we forget to have perspective and understand the likelihood and not just fall into extreme versions of one way or the other. So pairing it back and saying, okay, he’s actually very good at what he does. And he does himself assess the risks and knows when to utilise his skill or

to go maybe it’s time to call it a day and I kind of think okay well there’s going to come a time where he breaks a bone. How do I feel about that? Well the enjoyment and the lessons that he’s learning from that are also really really important because how do we know where those boundaries are? We only learn where those boundaries are by actually pushing them, nudging them. Sometimes we go too far but then that’s the way that we can pair it back for next time and I think it’s

Leanne Williams (43:46.592)
elements of that that we need to apply across our lives, work, home, the activities that we pursue. But the only way you stretch that, someone’s version of stretching, it’s going to be very different to mine, for example. But it’s about being aware that they’re the conscious choices and decisions we’re making and making sure we’re choosing to push it rather than just always take the safe line.

Yes, I dealt with this in a very real example when I was working with Rio Tinto and obviously a big mining company and your safety is such a huge part of the culture. Mining oil and gas though is such a big industry within Perth in Western Australia where I was based and where I grew up. That culture of risk aversion has actually permeated large chunks of society. Like quite literally, if I across the walks like jaywalked,

I could get fired or taken an unnecessary risk. were some of the directors or general managers at there that would have used that and seen that as an offense that was warranted basically being laid off. There was an extreme version of that risk aversion. And I do believe that that actually had, or I’ve used it as a story in terms of articulating the difference

that I found when I came to Melbourne versus Perth. So one Perth that there’s a very much a bit of a monoculture around mine oil and gas. It was like, you yeah, what industry are you in? It’s one of the three. Whereas I came to Melbourne and saw this richness and diversity of different industries and sectors that I was really, I kind of felt like with my kids growing up, it’s like, wow, you could be anything in Melbourne.

That was one thing that really attracted to me. But the other thing was around this, sense of risk aversion that was happening in Perth. I come to Melbourne again. Um, there’s this real, I use the example of the, the alleys, the lanes and the, and the streets within Melbourne. Whereas if you’re like a really established business, you, you set up on the street and if you’re not quite there, but you’re up and coming, you’re on one of the lanes. And if you just really just kind of trying to kick a new idea around, you could be in one of the little alleys.

Simon Waller (46:05.122)
And I literally saw a guy open a coffee shop where it was literally just lined with plywood and had milk crates to sit on. And he was down an alleyway with a massive queue of people out there waiting for their coffee. Like obviously the guy made great coffee. It’s like, yeah, one day you’re going to take that little risk and you’re going to grow that business. And so there has to be avenues for us to be able to take small risks to be able to grow ourselves. So I definitely saw that in Melbourne and Perth. So I see there’s a difference in that kind of cultural aspect of it.

Do you see it though here within Melbourne? Do you see like there’s certain areas where risk is more broadly acceptable? yeah.

Well, I think I just want to go back to your point though, where what you described in Perth and, you know, crossing the road, you know, not on pedestrian crossing. I see that as an example where we’re influenced by our external environment and by what the collective are doing. So if the whole environment is taking a really risk averse approach to everything, then that becomes the new norm.

And so, and I guess that’s what I nudged within this scenario was that over a long period of time, these small influences actually then start to nudge us into what that new norm is, which is she described say in Perth. Whereas when you come back to Melbourne and that diversity, it’s about, you know, it being so different and having all of those different examples around, you know, the laneways and streets and then, you know,

milk crates having coffee. It’s about how we continue to celebrate and push those opportunities so that we make sure we don’t just all become vanilla. I guess is how I view it. It’s being consciously aware of what are the things we can do to make sure we

Leanne Williams (48:09.464)
continue to celebrate the opportunities that come with a whole variety of opportunities that are presented and continue to push those boundaries. your guy selling the coffee down the laneway with the milk crates, that’s a perfect example of how he’s giving something a go. He’s put himself out there and taking a really big risk that’s then paying off and how he then continues to evolve that over time.

Hmm. Yeah, so a couple of things like one, I think that’s interesting about the scalability of risk. So how do we actually find it at different scales than when we’re ready for it? It does also bring in again that sense of asymmetry, which is that he’s got not much to lose. It’s like worst case scenario, he’s down a few mill crates, you know.

As opposed to when we talked about the story before about you in the bike accident, it’s like, well, suddenly there’s a lot to lose. And we do see that within organisations that as people progress, this kind of their their ability or willingness to risk things becomes lower, they become more risk averse as they kind of move up the hierarchy, because there’s not so much upside left in their kind of career, but there’s a lot more downside to lose some of the things that they become accustomed to.

I want to just play a slightly contrarian view for a second. And like a lot of the premise around this scenario, like, is there not a point where we can be okay with not having to consistently push ourselves? Like, and I talk about this both individually and as a society. So one thing that’s come up in this podcast as a theme is this kind of conflict between individualism and collectivism.

And possibly the load, challenges that we face within modern society is this, that our sense of individualism has been preyed on through a consumerist lens to get us to buy shit that we don’t really need. And that we need to somehow be reconnected with our collectivist view. Do you see that like this idea of risk taking and pushing boundaries is an extension of individualism or is that a different, do you think there are two things that are entirely unrelated?

Leanne Williams (50:29.292)
do think of things in parallels. think there are lots of influences that shape it. I don’t think it’s a one or the other. I think there are so many.

There’s so many influences that will go into how we approach risk. It’s to do with our upbringing and it’s to do with our environment. It’s to do with the approach to the organisation. It’s to do with what people’s experiences over the years have been, whether they’re positive or negative. It’s, you rewarded for taking risk? Are you penalized for taking risk? But then there is, I believe, a sense of as an individual,

Some will have a much greater appetite, I think just naturally. My mom would always say to me, she would, and she still says that she’s like, you have no fear. She will always say as a kid, I had no fear. So therefore if you view things from a perspective of having no fear, you’re gonna be a lot more likely to take stupid risks. Now what I would say is that fear lens has developed

over a period of time, because as you said, the stakes get much higher. So whether the stakes are high because you’ve elevated through the ranks of an organisation, you’ve got a lot more to lose, or whether you’ve had children and therefore you understand the responsibilities that come and you can’t afford to be lying in bed with broken legs. it’s, I think it’s such a really complex question. And really what I’m

digesting is that we have to consider all of those elements that come into it and make sure that we’re conscious and that we don’t just blindly accept, I guess, what a norm might be when it comes to heading down a path of risk aversion.

Simon Waller (52:31.541)
And with this, another kind of reoccurring thread in this is almost like this concept of the pendulums that swing from various extremes to other extremes in different aspects of our life. And, you know, there’s the individualism to collectivism view. There is kind of like, you know, at the moment we kind of almost have this extreme quite right wing, like…

governments being elected around the world, there’s actually been a response to actually has been previously quite extreme levels of global cooperation. If we were to look at that, that pendulum type of an approach and apply it to concepts of risk. So going from almost extreme levels of risk aversion, which is almost, it feels like you feel like we are facing. And in this scenario, we start to see the pendulum swing back.

to this idea of people employing chief risk takers, which there’s a certain risk attached to even employing a chief risk taker, especially without using AI to vet them. mean, like there’s an irony in that of itself, who came up with the idea of employing the chief risk taker and taking such a risk. Like, what do you see though, as being where does the pendulum go? Like, what’s the point whereby do you see, like say, take us another five or 10 years past this scenario.

What is the point where we go, whoa, I think we may have overstepped the mark here.

Well, I think that’s a great question. I love the way you framed it from a pendulum point of view, because we see this over history. And before I consider what it might look like after this scenario, my mind went back to we all remember growing up as kids and all of these playgrounds within the schoolyard. then some kids would have some accidents. And I don’t know about your school, but I remember all of the equipment got removed.

Leanne Williams (54:25.11)
Yet now we’ve gone back the other way and we have adventure playgrounds and you know, it’s about that risk taking. So I think the same thing would happen if you looked beyond the 2049 in this scenario. We do have that pendulum swing backwards and forwards and there’s a period of time where we find the equilibrium in the middle and we go, yeah, this is about right. But then there’s something else that happens that becomes a new trigger.

for shifting the pendulum back the other way. So all I would say is in that scenario, from a risk point of view, that I could anticipate that being the journey, know, decades into the future. It really comes back to what are the side triggers that are gonna signals that are gonna come in and swing us backwards and forwards.

Mmm, actually, you reminded me one story that came up for me when I read the scenario or even just eliminating on the topic itself. My aunt Lizzie and it’s not my aunt, it’s actually my wife Naomi, it’s her aunt. So Lizzie, absolutely amazingly beautiful human being, but she built the St. Kilda Adventure playground back in it must have been I suppose, you know, 70s 80s. And so much of it is

was actually her ethos around building it was actually to build real risky play into it. Like really risky play, like Tarzan swings and a whole bunch of stuff, you know, like, but there was enough and she was adamant about this, how important that risky play was for kids, but also in their own capacity to then build up that capability to assess the risk and to enter into those activities in a pretty safe way.

Sure, some people burned themselves on the fire pit, but then they learned to not burn themselves on the fire pit. Unfortunately, that got taken off her and then the council took it over and they actually took away a whole bunch of the riskiness. They were so risk averse that suddenly everything had to be either made shorter or rounder or kind of safer.

Simon Waller (56:38.214)
And there was a real frustration, I think, it probably quite upsetting for her to have created this space. It was such a mecca for kids because kids loved it. I think that’s the other thing. Kids are actually attracted to risk. They’re attracted to testing their boundaries. And it’s only now somewhere around 30 odd years later that they’re now actually starting to reinstate or there was a movement around playground design in the world about reinstating the riskiness to playgrounds with this idea that that is exactly the type of experience that kids need. So

maybe in some ways that pendulum is starting to swing. And where we’re looking at it from, you know, from a perspective of, you know, 30 odd years later, we kind of, we’re looking at us and the people around us and saying, oh, there’s risk aversion that wasn’t there when we were younger. But maybe there’s already that coming back in again.

Yeah, and I think also the point you raised there, like kids love the risky play. And I think maybe an important question for us to consider ourselves as adults is that we don’t, how comfortable are we as parents or adults with the risk that they’re taking? So rather than letting the kids assess it for themselves and then they learn and then they grow is that we’re imposing our risk aversion.

on them before they get the opportunity to learn that and then that influences what they do or don’t learn. But then the point I was making in this scenario is over time that continues to get diluted. you know, growing up kids don’t even get to experience that at all. And it’s really around us, like just considering that as a signal for going, hey, how are we wanting to approach

these aspects of kids growing up, making sure they’re assessing risks. Because, you know, I think I have a bit of a different view. I’ve had many broken bones in my, you know, growing up as having horse riding and I have had to stop and ask myself, am I comfortable with my kids breaking their bones? And so we just have to constantly ask ourselves these questions. I think it’s we can say, are we

Leanne Williams (58:50.99)
comfortable with our kids getting hurt? No, but we need to ask the question, but what if they’re not able to learn those things? Then what’s the consequence? It’s going, I guess it’s reframing the question or asking it in different ways and then there is possibly a different outcome.

Yeah, I think it goes back to that conversation around language that we use. So there is an outcome of the risky behavior, which is could be described as resilience is would we withhold the capacity of our kids to build resilience? Would you actively do that? Would you actively withhold that from them?

And most parents, think, would say, well, no, I wouldn’t. There’s no way I would actively withhold resilience building my kids. And it’s like, well, part of that resilience building is facing adversity. Part of that adversity comes with risk. So it’s almost like, yeah, I think there’s an ability for us potentially to reframe this in a way that allows us to engage in the conversation differently. Now I know that like you, it’s very clear from this that you draw on your own personal experience and are quite proud of your own risk taking behaviors.

even when the consequences have been significant. I kind of holding that in you, like holding that kind of potential for bias in you, you also have a belief, kind of deep belief around this space in terms of the direction that society should be nudged in. If people like listening to this podcast wanted to take, to want it to be nudged,

what would be the couple of things that they could do that would actually open them up to positive riskiness or resilience building.

Leanne Williams (01:00:35.47)
I like that. I think it’s one thing, and this is advice has been given to me over the years too, it’s about saying yes. So we’re very quick to say no when an opportunity presents itself that allows us to step into that risk zone. And I think the example that people give all the time is public speaking and people will say no before they say yes. And I think it’s being the…

I would encourage people to think about what’s the consequence of not taking on the challenge or what’s the consequence or impact of not stepping outside our comfort zone. Because when we reframe it like that, then all of a sudden we expand our perspective on whether we might choose to say yes or not. And so,

I am mindful of my own biases. I recognize that I sit on the different end of the spectrum to many other people, which is why I guess I embrace this scenario with such enthusiasm because I think it’s recognizing that I see tendencies of society going the other way. And I really wanted to, I guess, pose that question that saying yes and stepping into that risk space

isn’t necessarily bad and it isn’t going to see a downside in the way that people might expect. But I’m also not saying people need to go out and just be stupid.

I think, yeah, the same I picked up in what you’re saying is almost this idea of I’m a yes for now. You know, where was kind of like, I’m yes, until I can find a reason to say no. Like until and like I think about, you know, my mental imagery, it could be like you’re talking about in terms of downhill mountain biking, or it could be, I’m going to go on a flying fox. I’m yes, but now I’m going to buy my ticket. I’m a yes for now. I’m going to climb to the top of the tower. I’m a yes for now. I put the harness on me.

Simon Waller (01:02:40.11)
And there’s still the moment right when you’re actually in the harness on the phone. If you were saying no at that point in time, you can still be out. But like you’re actually testing yourself every step along the way just to say yes for a little bit more and a little bit longer. I really liked that as a premise that you could be a yes for now and just have a lot of micro yeses knowing that there is a no in you still if you need to play it.

Yeah, and I think I would go, I love that. And I would also just encourage, because I have a very distinct memory in my mind on the mountain bike trail once where I got to a hill that was so steep and I’d never done it before. And I remember being so present in the moment, so fearful, but had this little switch go off that told me to trust my skills and capability.

And I literally held my breath and thought the consequence could be quite significant in a negative way. But when I actually did it and achieved it, I was like, so I think it’s about, it’s yes for now, as you said, but I think it’s also making sure the message is trust yourself, trust your skills, trust your capability. And I know I say that from a women’s leadership point of view too, in the women that I coach, we have to have trust.

And we have to reinforce that to ourselves to help us nudge in that direction as well.

lot of this for you, I mean, coming on this podcast has been around being challenged and just saying yes. And, you know, a lot of the message that you’ve shared through this is that there’s sometimes either intended or perhaps even unintended or unexpected benefits of this. Just share a little bit.

Simon Waller (01:04:27.106)
Like from the moment that we chatted, I think it was now about a month or so back about the premise of you coming on here and we floated a couple of different topics we could talk about and you’ve gone through this process of research and getting some feedback and shaping this scenario and having this conversation. What do you take away from this? What have you learned either about the topic or about the process that you think will help you in the future?

Well, this is the perfect example that like coming on this podcast was literally the saying yes for now. It was also trusting my skills because I was pretty sure when Michelle suggested you need to go on the podcast with Simon and I was like, no. And I think, but again, what I learned from the process was yes, that fear of the unknown.

uh, is something we have to navigate on a daily basis. But at the same time, you know, I know you, I knew that I felt really comfortable if I was wanting to go on a podcast, it was going to be with you because I listened to your podcast and I love the humor that comes in and that, you know, that comfort that comes along with that. So I think it was about, I felt like I was stepping into a safe space. Um, at the same time, I really

liked being able to frame it through that personal lens made it bring a very different perspective that reshaped how I might frame the scenario. But then it’s brought in something that I’m quite passionate about as well.

Yeah, I find it really interesting. And one of the things I find is potentially the benefit of this conversation. We’ve had a bunch of conversations, so many conversations over the last four years, we would have spent like, literally days, if we’d add it all up, it’d be days that we spent on the phone or in person talking to each other. Yep. And in that we have touched on some of the stuff around the biking and the accidents and everything and

Simon Waller (01:06:28.744)
This is the first time though that we’ve actually got to reveal what’s actually behind this for you in terms of the childhood experience, in terms of this deep held beliefs that you have around, know, resilience building as opposed to risk taking. And I think that’s also really revealing in terms of, you know, the power of having a conversation as friends rather than just having to be entirely framed in the context of, you what we do in our work.

or what we do for our jobs. This has been great. I’ve really loved having you here, Leanne. I’m so glad that you reached out. As I said, it’s a conversation I really wanted to have and it has not disappointed me.

Thanks, Simon. It’s been fabulous to be able to come and have this conversation. Thoroughly enjoyed it.

Awesome. Well, that’s all for this episode. We’ll be back in a couple of weeks. Until then, take care and don’t be risky.

Bye.