The AI mistake no one saw coming

What happens when you introduce AI to “help” your people… and they all go on sick leave?

In this episode of Who’s Elvis Around Here?, Chris sits down with leadership expert Joe Hildebrand to explore the human side of AI — and why so many organisations are getting it wrong.

As AI rapidly reshapes the workplace, leaders are facing a critical choice:

👉 Use AI purely for efficiency, cost-cutting, and productivity
👉 Or use it to unlock human potential, creativity, and growth

Joe shares real-world stories (including one AI rollout that completely backfired), powerful leadership frameworks, and why psychological safety, storytelling, and co-creation are more important than ever.

This conversation dives into:
- Why removing “mundane work” can actually harm employees
- The hidden stress AI can create in teams
- The “Red Pill vs Blue Pill” decision every leader faces
- How to balance structure and freedom in modern leadership
- Why the biggest risk right now is losing the human connection

If you’re a leader, founder, or simply navigating change in the age of AI — this episode will challenge how you think about work, people, and the future.

Transcript

SPEAKER_01 0:08

So, welcome to the Who's Elvis Round Here podcast. This is where I get to hang out with some of the coolest folk on the planet and learn about what makes them tick and how they can help us all understand how to release the genius of our people. And I'm delighted to have with me this week Joe Hildebrand. Welcome to the show. Hello, Chris. Thank you for having me. It's an absolute pleasure. So obviously, we've we've been kind of in each other's orbits for a little while, but a lot of people won't know who you are and what you do. So give us a bit of context to who Joe is. I will.

SPEAKER_00 0:39

Well, it's great to be here. I have spent all of my career in the leadership and culture space. So my biggest passion and interest is thinking about why people do what they do and helping them do things in new and different ways. So spent my time in consulting at Accenture and Deloitte, a bit of time in-house at BT, a joyous few years at What If Innovation, where that's where our orbits collided, Chris. And then funnily enough, What If got bought by Accenture. So I returned to the fold. And then more recently, I've left and I've set up my own business focused on the human side of AI.

SPEAKER_01 1:17

Wow. So all that leadership experience and now colliding it with AI, which is ever present on everyone's minds. So I'm sure we're gonna we're gonna get some good good learnings from today. So great to have you on. So uh first first question of the day. Um tell us the story you love to tell that people love to hear.

SPEAKER_00 1:33

Well, I was thinking about this, and obviously, working in the world that I work in, we're looking not just at the tech, but predominantly at the people, and I find the anecdotes to make a point really powerful. And often I spend time with clients talking to them, hopefully convincing them about the importance of humanity, which I know you and I agree strongly on. And the story or the anecdote that I heard that I think is really powerful is there was a client that uh we were working with a long time ago, well not that long ago, um, and we were looking at how to implement AI. And one of the questions was how might we put AI in place that improves the customer experience but also helps those human agents that we speak to on a regular basis do more and add more value to the business. And so the business case was created, and we put in this fantastically high-tech AI chat box to take different calls from customers. And the story that we told or that was told to the employees was what we want to do is we want to free you from those mundane, those transactional tasks so that you can really do what makes you thrive. So, really powerful intent and a genuine intent as well, and so that all went into place. And what we found is those human agents they all went on sick leave, and they went on sick leave because those transactional tasks that we'd removed away from them was their deathbite. It was their opportunity to take a breath, of course, and no one thought about it, and it it really painted that picture, I think, of how important it is to consider humanity and how we operate and how we breathe and live, not just our heads but our hearts as well, especially in the age of AI.

SPEAKER_01 3:18

And look, it's it's a it's a fascinating insight, isn't it? And you know, we're doing quite a bit of work with call centres. I mentioned this to you the other day, and you know, a lot of people's uh ambition is to obviously make most of that AI because of obviously the cost savings, but they they always hold back the humans for the tricky stuff. So you your job suddenly goes from you know, it was 10% tricky to it's a hundred percent tricky, which is a very different way of being, right? So I can totally understand why they found the stress through all a bit too much. And isn't it isn't it funny? You don't get that stuff until you've done it, and it's really obvious.

SPEAKER_00 3:50

Exactly. And I think it's those stories, those kind of war wounds that we go through that we've really got to acknowledge. But I I think sometimes we can avoid those things in the first place by co-creating and having the right conversations with people. All too often, leaders and companies, we sit in a dark room, we're smart, intelligent leaders that have done great things in the past, and we think we know the answers. I know everyone watching this will probably know this already, but it's such a misstep. Like avoiding those conversations or going at pace and forgetting to have those conversations is a real challenge. And I think, especially with the pace at which AI is happening at the moment, we need to be spending a hell of a lot more time having those conversations and spending time with our people.

SPEAKER_01 4:34

Yeah, definitely. And and you know, and doing things a bit more fleet of foot, trying things out, experimenting, learning as you go. Uh, because if you if you go in too fast, things like that are gonna hit you in the face, that's the no doubt. Uh we're learning so quickly, uh, it could be a rather disastrous, expensive mistake.

SPEAKER_00 4:49

Yeah, quite right. Absolutely. I think it's it's it's such an important part. I think we'll probably talk about this as we go on, but the whole, you know, having people's fingerprints on everything that you do, it doesn't mean that as a leader you need to kind of empower everyone to the extreme where you've got no control and people are running around like maniacs, you don't want that. But giving the people the opportunity to put their fingerprints on the decisions that you make, it solves for stuff like that. And it also means they're so more invested in making the solution successful. Um, but we we miss it too much.

SPEAKER_01 5:21

Yeah, yeah, but yeah, for all sorts of reasons. So that might lead us into this next question. So um, if there's one single thing that you think is vital in releasing the genius of your people, what would that be, Joe?

SPEAKER_00 5:33

Well, I was I was gonna cheat a little bit because I always say there are three things. Um, can I start with three and folks?

SPEAKER_01 5:39

Yeah, come on, we can shoehorn two more in.

SPEAKER_00 5:41

Thank you. You're good, man. Thank you. I so I I think the the key to anything to help people thrive in an organization, whether you're shifting culture for this reason, that reason, or another reason, the first is is psychological safety. You've got to give people the safe space to try new and different things, because if you don't, they're gonna be having what they've always done. So, how do you do that? Well, you mentioned there's experimentation, you give people the space to try those things in a safe way where they can celebrate the successes but also the failures and the learnings as well. And as you do that, I think the answer to my question is the third one, which is storytelling. I think the capturing of those stories and the propagation of those stories across the organization is one of the most powerful things, and it's not just stories around we've sold more or we've acquired new clients or customers. It is what was the journey as a human being we went on to move from here to here? What do we learn? And you create this virtuous circle because the more stories there are, the more safety there is for people to do new and different things, so they experiment more, which gives you more stories, and around around you go. I think storytelling is one of the biggest gaps in the leadership as well. I think it's undervalued, I think it's underinvested in, and I think it's a game changer when you get it right because it creates those human connections, and you get it really right, and you get leaders who are happy to be vulnerable and not pretend they know all the answers, especially today, because no one knows all the answers. Anyone who says they do is a liar, right? No one does. It makes a big, big difference.

SPEAKER_01 7:20

Love it. I love it. So um it sounds to me as if in that situation, what you're doing is you're creating the conditions for your people to step up, own the future, make sense of it in their own way, so they can put their fingerprints on more things. But but but it's it's the balance there of how much direction does the leadership need to give uh versus how much freedom do they need to create? Because actually it's the it's the combination that that is is going to be the kind of breakthrough. Well, have you got any any tips on how to do that? Because I get I get asked this question all the time, because everyone sees me as this massive hippie and go, oh, you just want people to just run their own lives. I'm going, no, I'm not saying that. We do need some leadership direction, but you know, for me, the end goal is that your people show up every day, they make sense of their world, they learn what to focus on, they review themselves and get feedback. Ultimately, they should be able to reward themselves, you know, when this is all working. Um, but obviously, there is a leadership job in that, which is a lot more about support and coaching and helping them with the capability and the confidence to do so. So, do you as you've played in this area quite a lot? Um, I I'm just trying to steal answers from you. What do I say next time when I'm asked that question?

SPEAKER_00 8:30

It's a great question. It's funny. Whenever I talk about this, I have similar questions. Sometimes I'm looking at someone, a client that I'm working with, and I think when we talk about experimentation storytelling, I don't know if you've ever seen that clip in The Simpsons where there zooms in on Homer's brain and there's two cats like hitting each other on the head with mallets. That's what that's what these people are thinking when we go, let's experiment, and they're going, No, it's going to be anarchy. How are we possibly going to control it? So maybe there's two answers. I think the first is if you are a really good leader and you can set a really robust and compelling strategy. I think the story that bees that's built off the back of that and the amount of fingerprints that you get on it is quite a six you know, straightforward thing to do because you kind of set the parameters, you've made it clear what you want people to do. I think the other answer is maybe sometimes it's the top leader's role to set the why, maybe the what, but the fingerprints piece is the how. So if you've made really clear why we need to do what we do, the purpose is clear, everyone understands it and is bought into it, you've given them some guardrails about the three or five things that we need to do as an organization to achieve that why, and you give people the skills they need to go and achieve all of that, then how should be down to them because they're closest to the front line, they're closest to the work. And again, you you pivot. Sometimes they'll go off, and one person will go in this direction and that direction. But if you set the parameters narrowly enough, those different directions aren't going to be broadly and far from each other. Um, and if they are, you course correct, and and you can only course correct if as a leader you're keeping your fingerprint, your your excuse me, your finger on the pulse. So I talk a lot about um great disconnect. So there was um you you'll probably remember the great resignation, right? It was a term that was used during co-juncture where people made really interesting decisions about their lives and their work because something existential had happened around them they had no control over. And I think the great resignation was a thing, but when you really scratched beneath it, it was actually about the disconnect between leaders and their people, and that manifested in mental work as well. All of these big leaders coming out and going, right, we demand everyone back in the office five days a week, and their employees were going, No, thanks. Actually, you're not listening to me, you're not listening. I've changed my whole life as a result of COVID, and now you're asking me to revert back to a different way. Now there's a happy medium to be found, and there's lots of research out there that talks about is it synchronous work, is two days a week, asynchronous three days a week in the office, whatever you wish. But it was another example of where that disconnect was so big. And if you're not spending your time connecting your people as a leader, you're never going to be able to get to the right outcome.

SPEAKER_01 11:23

Yeah, and and uh you know, I've seen this in examples of companies that are like night and day, ones where literally there is no conversation whatsoever, and um people are taking the dart, they're they're they're operating from a very traditional leadership framework, uh, sweating assets, all that good stuff. You know, it's almost like it's controlling people, largely is what it is. Um, and obviously their salaries, because that's a big uh part of whether successful or not. And then and then other places where they are so fluid in the way they show up because they're talking on a daily basis, they can they can flex depending on what's needed here. And um I I still cannot believe the first one is still in existence, but it's still out there, and actually, more often than not, that is the kind of norm. Um, what what what is it do you think that that is um is the reason for that hanging? I mean, you know, this is this is a model that was this, I mean, people shot it apart with amazing research in the 60s, right? And and it's still hanging on there, going actually, no, this is the way business should be. What is it do you think about that particular model that certain businesses and certain leaders find so hard to let go of?

SPEAKER_00 12:36

I think it's probably comfort and pressure. So I think it's a comfortable place for many leaders to be in, but I'm I'm being really broad in my statements, that's not true for everyone. And I I would wonder whether it's quite different for different generations. True. So honestly, I think you know the older generation of leaders are comfortable in doing that, and that's why they continue to do it. It's their it's their comfort zone, you know. Why why would they change? Uh, for younger leaders, I think, because they've grown up in a different way and have potentially different values or different beliefs, I think it's probably less prevalent. But the pressure piece is probably one of the more important pieces, you know, particularly if you're in a PLC or you've got shareholders to answer to, that pressure often I would suggest leads to leaders kind of almost contracting, if it were. How do I cover my back? How do I make sure I can answer upwards or sideways to the people around me? And often the default answer is control. Um, maybe again because that's comfortable, but it's probably the wrong answer as well, quite the opposite.

SPEAKER_01 13:44

Yeah, I mean, well, a lot of the structural ways that businesses put together definitely encourage people to avoid risk and to become more controlling over decisions and stuff. I mean, you know, just quarterly reporting to the city, yeah, you know, you've got it's hard to overcome that. I know Paul Pollman stopped doing that at Unilever, and that was a massive kind of revelation. And it and it changed, you know, certain dynamics within the business. But it's quite hard for people to escape those sorts of institutions because that's kind of how they get funded, right? So you know, there are structures that push against it. I guess the better place is the ones that go, well, it's not perfect, we haven't got this right, but in those circumstances, we can still show up with humanity and we can still create those conditions, and therefore, a lot of it comes down to your first bit, which is this identity thing. How do I, well, how do I think about myself as a leader? How do I add value in the best way that's appropriate to who I am?

SPEAKER_00 14:34

Yeah, yeah, totally. And the identity piece is fascinating, particularly in current times. I've been playing with what I'm calling AI EQ. So let's assume in the AI model that we've been, yeah, people people are really confident with the tech, and then you hear lots of conversations about literacy. So, how do we build capability to use AI to prompt engineering, learning about LLMs, all of those good things? I would classify that as AI IQ, and that's quite a comfortable zone for most organizations to be in. We're quite good at kind of doing cheap debt training. The EQ piece, the humanity in AI, has got components to it, many, but one of which is identity. Um, and that identity piece you triggered a thought. I think that's true in the context we're describing, but actually, identity is evolving dramatically as well for all of us, because what we were valued for, what we were paid for, what we were performance managed around, a lot of that, no matter where we are in the organization, is moving away to AI. So, what becomes of us? What is our identity? What are our values? What what why do we exist in an organization? Pretty dramatic shift, more so than I think we've seen in the past.

SPEAKER_01 15:45

It's huge. Yeah, and of course, you know, shifting identities is the hardest thing I think we can ever do. And uh, you know, when one feels as if your identity is slightly threatened, you know, and it's not a choiceful thing, it's it's actually being pushed upon you, people often just restrict and they start to avoid even more risk. And therefore, you know, I'm seeing this all the time with people who are hunkering down, you know, they were quite cool leaders five, ten years ago, and actually in today's climate, they're they're actually they've gone back some steps, and and they're starting to you know just protect them and their teams as much as they possibly can because they're just gonna know what's happening, and I think that's that and it seems to be a big issue with a lot of the clients that I'm working with. I mean, it's a fascinating time, Joe.

SPEAKER_00 16:27

It is a fascinating time, it really is, and it's it's something and I wonder whether sometimes that that kind of hunkering down and as you describe it, it's pretty natural. So, you know, I think the work you and I do is really important that we can empathize. I'm sure we're experiencing it ourselves. Like it's a natural, but how how do you solve for that? How do you really embed curiosity? So it's an opportunity to go, but you know, I feel threatened, but let me learn, let me see what the alternatives could be. That's hard to do as an organization where the hardware, you know, we're talking a lot about the soft wiring, if I can describe it like that, but the hardware still incentivizes old ways of working or the reporting to the city or whatever, it's really difficult to move away from that.

SPEAKER_01 17:14

It is, it is, and you know, I I think I mean there there is some benefit in saying, well, what can I control? Where can I experiment? Where can I be myself, which uh which will hopefully give us the growth and and you know the advancements that we're after? Which bits can't I play with? And actually just getting some clarity on where to do that, I think is important. If you're playing with everything all the time, it's exhausting. So yeah, and a lot of it comes down to kind of you know definition of zones, I guess. Um, but look, with all this stuff going on, and there's a lot going on, and I know that you're part of a lot of this big change coming. Um what gives you hope, Joe?

SPEAKER_00 17:51

I am actually quite hopeful. I when we when you and I first were talking, I shared this with you. So I think leaders are making a choice right now. They can either take the blue pill or the red pill. So the blue pill, if they were to take it, they would see AI through the lens of cost, productivity, and efficiency. It's the default way that most leaders look at new technology. It's why AI is becoming a hammer looking for a nail at the moment, which isn't serving as well. Or they take the red pill, and if they take the red pill, they see AI through the lens of freeing their people from the drudgery of the day-to-day, giving the opportunity to truly thrive, to help your organization reinvent and acquire new customers. And I'm out and about, you know, in a fortunate position, having really great conversations with great clients, and I'm hearing a lot of them who really want to take the red pill, they really want to go down that second route, they understand it, they believe in it, they care about it. Um, it's not easy, and a lot of them are still taking the blue pill. Many of them are looking for a purple pill somewhere in the middle, which I think is a fair problem. Of course. Why not? You know, but I'm I'm hopeful for that reason. I'm I'm not hearing anyone going, oh, you know, human humanity and AI, that's a waste of time. Not hearing that quite the often.

SPEAKER_01 19:09

Yeah, and and and uh, you know, I did this piece the other day, I think we chatted about it, uh, and and the ethos of it was that actually technology is neutral. It's the way we deploy it that that is uh whether it's positive or negative. And I was sharing my story of, you know, obviously I work with these huge companies, um, and you know, they've all outsourced their billing now to play a place like Candex, uh, which is great because actually it should make things more efficient, it should save time and money, and all that kind of stuff. But the way it's deployed, it basically means that they're trying to instill 120-day payment terms on me. And and every time I pay a bill, it's two percent more to pay for Candex. And it's kind of like, well, the idea of the tech is fantastic, but the deployment's not on your values, and it's nothing to do with humanity that you talk about on a daily basis, and it's just it's just one of those quite close-up versions, but we're gonna get a lot more of that, you know, where actually you have to kind of look at yourself and say, is it just about optimization, efficiency, you know, profit, or actually, is this gonna help people live better lives and help humanity survive better on this wonderful planet? And those are gonna be some big chats we're gonna have to have, right?

SPEAKER_00 20:13

Quite right. Yeah, and I think again, it was probably true a little bit in COVID, but much more so now. I think this the role that big organizations play and their leaders in society is pretty fundamental. I mean, that again goes beyond contributing to an AI skilling program for the government, although that's really important, those kind of things are great. But genuinely, the choices that leaders are making now, not wishing to place more pressure on leaders, but I think it's intriguing is fundamental. Like it's gonna change the fabric of society, and we need to be really mindful of that and purposeful about it. And I know and truly believe we can get to a positive outcome with it, but not if we kind of sleepwalk into it. I think it's got to be really deliberate.

SPEAKER_01 20:53

Yeah, yeah. Well, again, that really resonates. So, um, so you've got some exciting stuff coming up. Um, so what so what's in the future that gives you loads of energy, Joe?

SPEAKER_00 21:02

Uh well, I so I I was I launched my business last week, so kind of thank you, Chris. Um, been doing some good work, so formally out and about, um, building the world of Humari. And so that's the most exciting thing for me right now, and probably the most exciting thing I've had the opportunity to do for a very long time. Um, having these conversations that we're talking about right now with clients, helping them think about how they might take the red pill rather than the blue pill, and then going to help those organizations genuinely transform in service of humanity, not just in service of technology. So it's really exciting, and there's lots to be done in the world out there, I think, at the moment.

SPEAKER_01 21:46

Yeah, a lot to be done. I look, I if people listen to this podcast, chances are they want a red pill. So um so we'll make sure we share your links. Uh, because some people will be looking for your help for sure. But Joe, look, thanks for coming on. I've really enjoyed the chat. I mean, um uh You know, your insight into leadership is obviously fantastic, but the way you're connecting up the dots with where we're going with tech and AI specifically is is wonderful. So thank you for that. Uh look forward to hanging out more uh in in the same kind of uh stratosphere. So go well and good luck with the business. Thank you, Chris. Nice to see you. Take care.