AI Leadership & Culture: Why Rollouts Fail Across Borders

Speaker A: AI rollouts in global organizations succeed when leaders focus on trust and authority, not just the technology. That's the part of the story most people are not telling. And many times leaders say my team is resisting the AI tool and what they're actually asking for is a real diagnosis. Teams want to learn the tool. They are also trying to figure out what it means for them. When leaders explain explain the why and the how, momentum follows. When that signal is missing, the team waits, and the wait gets read as resistance. Closing that gap is what saves years of stalled momentum.

Speaker B: You're about to hear a conversation that goes well beyond the usual AI narrative. In today's episode, I'm joined by Rui Bashir. He leads up HR at a Fortune 500 multinational which is with scope spanning more than 20 countries across the globe. He's built a career over nearly two decades sitting in the rooms where the global playbook meets reality. His unique zoomed out view across cultures and time zones gives him a rare inside perspective on how AI rollouts really land on the ground. We explore why identical strategies produce completely different outcomes across cultures, how leaders misread resistance, and what it truly takes to lead change at scale in 2026. He also shares powerful insights on the apprentice gap orchestration between humans and AI, and why Nelson Mandela remains his most admired leader. If you're leading transformation right now, this is one for you. Well, good morning. Thank you for coming on the Level Up Leadership podcast. Would you like to start by just introducing yourself and saying what you do?

Speaker A: Thank you, Lee. I'm Raoul Beshear. I lead global HR in a Fortune 500 multinational and my scope spans across more than 20 countries. I am trilingual in English, Portuguese and Spanish. I've built my career across the globe nearly two decades sitting in the rooms where the global playbook meets local reality. What I want to put on the table today is this. AI rollouts in global organizations succeed when leaders focus on trust and authority, not just the technology. That's the part of the story most people are not telling.

Speaker B: So you're leading a HR across 20 plus countries. Is that something that you always had as a career path in mind or what was your leadership journey and how did you end up doing what you're doing now?

Speaker A: Great question. That was part of my North Star, uh, definitely. I always worked for global organizations and being in regional or, uh, global roles. I started my career in South Africa and then I had opportunity to spend some time in Mexico as well, leading HR within the Latin American region. And for the past five years I'm based in the US Where I hold a global role in hr. So definitely that was part of my career planning. That's where I am now.

Speaker B: And it's the human part of human resources, which really captured my interest when we started talking, because I spend a lot of time talking about AI. I'm an AI enthusiast. I've written books on it, and I talk about it all the time. And more and more, I'm coming to the realization that it's the human in the loop, which is so much more important than the shiny new tech. The tech, obviously, is important as well, but it's about getting that balance right. And I think that's what sparked my interest when we started talking offline around AI rollouts. 2026 is the year of AI rollouts, as I suppose 20 was as well. And you mentioned some of your thinking around what makes a rollout successful and what are some of the common themes when a rollout isn't successful. So would you like to say a little bit about what your take is on what makes for a successful or unsuccessful AI rollout? Sure.

Speaker A: What I see is the standard way to run an AI rollout is to treat it like any other change. Right. That what I have noticed, train people, communicate, measure, adoption. I think that works on the surface. What is going on underneath is trust and authority. When any big change happens, people quietly do their own math. What might I lose? What might I gain? Whose role gets bigger? Whose gets smaller? Do I still matter? Uh, the trust question is whether they believe someone will handle all, all that fairly. The authority question is whose role is being changed and whether anyone asks them. AI rollouts bring all of this up faster and more visibly than almost anything else. So the rollout deck, the training plan, the announcement, all of that comes after. When you handle, uh, the trust and authority piece first, the tool actually delivers what it was supposed to. That's how I see a successful rollout. And many times leaders say, my team is resisting the AI tool, and what they're actually asking for is a real diagnosis. Teams want to learn the tool. They are, uh, also trying to figure out what it means for them. When leaders explain the why and the how clearly, momentum follows. When that signal is missing, the team waits, and the wait gets read as resistance. Closing that gap is what saves you the years of stalled momentum.

Speaker B: So in many respects, we're talking about classic change management rather than a new style of change management. Obviously, it's about deploying AI. But the fear factor of the unknown is still there. You know, when Something's new and unfamiliar that can breed a kind of resistance purely because unknown things are a bit frightening. So we're talking about basic communication. What exactly is it? What does it mean for you? And why are we doing it?

Speaker A: Definitely. And I want to link this thought process also with something you write in your book, the bionic leader. The leader who keeps the humanity at the center, uh, and uses AI as augmentation, kind of saying that humanity first framing is exactly right. But it is harder than it sounds that framing is exactly right as a destination. The part is where I get stuck. Human first, then augmented assumes, uh, you have a stable human starting point in a global organization. That human starting point looks different on every floor, every country, every function. The same bionic idea works beautifully at headquarters and needs translation three time zones away. That is the part I keep coming back to. Which brings me to the piece this conversation almost never gets to. Which is a cultural piece.

Speaker B: Yeah. And so you've got a really good zoomed out view of this working across 20 different countries. So I'm really interested to hear, you know, what are the commonalities, but also what are the unique things around cultural differences. Also, um, cutting across those different landscapes and different cultures. What are the limitations or the biases in the system? This is something I hear quite a lot of as well. How do we safeguard against biases or lack of cultural nuance? So this is very much the specialism I was hoping to hear. So please share your thoughts on this.

Speaker A: Yes, definitely. Authority and empathy are, uh, intention in every leader. Uh, what changes across cultures is which side reads as strength. So let's take a single word, courage. Uh, in Anglo American corporate culture, courage is the lone voice at the table. Dissent as virtue speak truth to power. We celebrate. Executive woodbreak rings and says the thing nobody else will say in Portuguese. Courage is different. Courage is something you draw from the group. Collective resolve. You go to the front because the people behind you go with you. The lone voice is not quarraging. The lone voice is suspect. Why is that person alone? In Spanish, there's something called coraje estrategico. Calculated, often invisible. Knowing when not to use is part of the skill. The courageous thing is sometimes the thing you do not say in the meeting. So, three languages, three definitions, one word. Now design an AI rollout that asks teams to speak up if they have concerns. Three teams hear different things. Three. The American team complies. The Brazilian team interprets the silence as deference to the metrics. The Colombian team performs adoption while quietly killing the Initiative, same M product, Same training, same KPIs, completely different outcomes. The headquarters analysis is always change management problem. That's usually the first, uh, observation. The standard read is that the local team is struggling with change. The local team is not struggling with change. The local team is doing exactly what the culture taught them to do when they sense the calculation is not safe. Uh, what sounds decisive in a New York boardroom, um, can read as domineering in Sao Paulo and dismissive in Bogota. None of that nuance is in the standard AI rollout playbook.

Speaker B: You've just slightly blown my mind there and I'm going to look forward to playing this back and really getting my head around some of this. It's going to take a bit of time to process it. I think playing out on a global scale there is a step beyond something that I've ever been involved in in terms of uh, a change program. But what I'm hearing parallels in is that that's a more amplified and more challenging scenario of what perhaps sometimes plays out where there's different communication or learning styles and different behaviors even within a team, which is a similar national culture. But across a large. If you've got a thousand, ten thousand individuals, you'll have your introverts and your extroverts and you'll have your auditory or you'll have your people who prefer written communication. And so sometimes those different reactions can be interpreted differently even just within a single culture. So I guess I always like to try and give some advice and particularly aimed at frontline leaders who have to wrestle with this every day. What would be maybe one or two tips for how leaders can navigate those kinds of differences to try and help their teams on a change journey?

Speaker A: Sure. Uh, most leadership advice was written in one dialect and exported as if it were universal. I'll go back to your book where you talk about the captain and the Android. The captain has the nuance, the Android is the logic. Most of what we are calling AI rollout is Android logic applied to captain problems. What I'm describing is even more uncomfortable. The captains nuance itself as dialects. So going back, the advice is usually written in one dialect and exported as if it were universal. So um, I always go back to the translation. Not language translation, cultural translation. The same leadership move reading differently in different rooms. Which leads to the biggest opportunity I see in any change management initiative and even in AI and leadership development, the diagnostic piece. It's very important, my advice is very important to go deeper, uh, and close the diagnostic gap. Let's picture Two leaders both say the same thing. They cannot trust their own judgment. Same words, same energy, same way they show up. But what they need is completely opposite. Leader A was promoted because they are technically brilliant. Uh, they never had to make a hard call under pressure. They have never built that muscle. What they need is practice. Real decisions, real stakes. Build it from scratch. Let's go to leader B, used to have that muscle. They build it over a decade of hard calls. Uh, then they watch it weigh down. Years of being second guessed, overridden decisions reversed. Uh, that muscle is still there. It is just worn out. They do not need more practice. They need to be trusted again so they can trust themselves. Same words on both of them. Completely different problems. Get the diagnosis right and the help lands fast. Get it wrong and you waste six months. With leader A, you keep telling them they are great when that they need is actually make the call. With leader B, you keep pushing them to make calls when what they need is someone to say the judgment was always sound. It just got beaten down. Either way, you make things worse. So the diagnostic piece, it's very critical. And that's my advice. Spend time on the diagnostic piece.

Speaker B: So that issue is the metaphorical tip of the iceberg that you can see. And for both of those leaders, it looks the same, but it's what's under the surface, which is sometimes drastically different. I see this play out sometimes, I believe, and I'm not the first to say this, but all great leaders are great coaches. And when you take a coaching leadership style, you ask questions before you rush to advice. And maybe you don't even get to advice at all because you use the questions to encourage the thinking. So that's some advice I would give to any of our newer, uh, leaders who perhaps, uh, and I see this play out where people maybe get asked a question, someone in their team needs support or advice. And those leaders who aren't perhaps used to coaching, they'll rush to an answer. Uh, because maybe they used to be the expert. They're the oracle. They have the information. And sometimes it even feels good to be able to give that information quickly and, um, you know, individual. But if I would give one piece of advice off the back of what you've just said, Drew, is that if you just ask those few more questions to start with, scratch the surface, you'll then see that actually the issue maybe isn't coming from the place that you thought it was coming from. And by asking some more powerful questions, you can really diagnose. And then that will lead you to a much surer place when it comes to actually trying to fix the issue. So thank you for that. I guess that's a really helpful way of um, framing it. Have you, is, have you got any examples that you've seen where this has done well across your cross cultural lens where people have actually adapted their communication style and had some success?

Speaker A: Definitely there are a few examples that I have seen where this is done well. And in many organizations one of them is always adopting that learning mindset. Move away from the know it all mindset and adopt that humble learning mindset. Being able to connect and complete that diagnostic across the world if you are part of a uh, global organization. And adopting that learning mindset I tend to see is always a powerful tactic to make it successful.

Speaker B: So we spent quite a bit of time talking about the humans in the equation. I think maybe we should also spend a little bit of time talking about managing the AI or the agents. And a word that I know that you've used is orchestration, which I think makes a lot of sense. But perhaps for those who maybe aren't in this space as often as you or I. Do you want to say a little bit about what your thoughts are on orchestration of hybrid teams?

Speaker A: Definitely. Let's look at the coaching industry. I think it's a great example. There is a lot of discussion about AI being deployed in coaching and leadership development at scale. I think AI is great at scale. It is great at spotting the symptom humans bring, the depth humans can tell whether the muscle was never built or got worn down. If we go back to the two leading examples that I just shared, when you put the two together, ah, the human and the AI intentionally you get something neither does alone. People are still arguing about whether AI replaces coaches. The more useful conversation is how AI and humans together change what it is possible. I think that's a very important aspect of this combination. So the deeper taste is whether AI ever ask the right question in the first place. Right. If we go back to the question piece and asking those powerful questions when you coaching or you involve in leadership development, uh, with leadership development the wrong question routes you to the wrong intervention and the wrong intervention can take years to undo. We have seen this with or without AI. We at the risk of scaling the wrong question into thousands of leaders, uh, leaders development plans without anyone noticing the diagnosis was wrong from the start. So that's why I speak a lot about orchestration and that's a place where I keep coming back to what is the human actually doing when the machine handles so much of the work. For me, it comes back to that same word, orchestration. AI, its execution. Increasingly the doing is automated as we know what remains for the human is the allocation problem. Let's say where does direction need to be given versus absorbed? Where does trust needs to be granted versus withheld? Where does connection needs to be invested versus protected? Or where does courage needs to be spent versus saved? AI is not going to make those statements, distinctions. The human is going to make those distinctions. And humans or leaders, we make these calls every day. Most of us are doing it instinctively. The opportunity is to make those calls more visible so as leaders, we can deliberate about where each scarce resource goes to. So that's orchestration between humans and AI.

Speaker B: Can I zoom in on the word trust? You've mentioned trust, not just in that answer, but earlier on as well. And I think hopefully we all know what trust looks like in a human relationship. What does trust look like in an AI augmented team?

Speaker A: That's a powerful question, Lee, and thank you so much for asking that. AI generates a lot of information. I believe trust is something that humans still have mastered as a skill or as a trait or behavior, or as a tenet of this relationship between AI and humans. What happens is that the amount of information that we are able to extract to AI or to any tool and how we use makes or breaks the trust. So it's very important that we also spend time looking at the information. And I'll go back a little bit about using this cross culturally because it's very important that uh, when we take that information and we translate that information across cultural cultures, we also making sure that trust is preserved if we want to be successful.

Speaker B: You're listening to the Level Up Leadership podcast. If you found this episode, that probably means you're a leader looking to level up their leadership game. If that's right, make sure you follow us and subscribe wherever you find your podcasts. We're available on all major platforms. If you subscribe to our YouTube channel, you'll see we regularly have additional bite sized mini clips of the most important points. And if you subscribe to our main hub on Level Up Leadership, that's all one word. Levelupleadership.uk you'll have access to the articles that come with each episode, as well as additional bonus articles, some of which are guests or collaborations with other writers. Make sure you follow and subscribe to Level Up Leadership now. Okay, back to the episode.

Speaker A: Things are moving very fast. Definitely this is evolving significantly. 2026 is, uh, key and critical year in AI deployment. There's a lot of energy across organizations in deploying effectively AI. I also want to connect this question with something I think you write about, which is the apprentice gap. Right. The idea that AI is eating the entry level work that taught people how to do the senior work. So this is kind of going into like a deeper version of that. The apprentice gap you describe is real and it's becoming real every day. And I think it's really bigger, uh, at entry level. I think we are losing the apprenticeship in the calls. We can only learn by making them ones where we decide who to trust today, where to push back, when to wait, when to spend that connection. And AI is already taking the operational work off the plate. Right. And I believe that in the next 12 months that's going to be even more intense in the way that jobs are starting to get shaped, including entry level jobs being reshaped across the industry, across the organization. Uh, companies are investing more in bringing in talent that do have some level of AI native skills. And I think the biggest opportunity to close that apprentice gap is for high schools. Universities also start investing in the curriculum, some of those AI native skill building. Otherwise that gap is going to be bigger, uh, and adjustment is going to be very costly to the society.

Speaker B: Yeah, I think this is the biggest area that we all need to be collectively focusing on. And thank you again for mentioning enhanced leadership. The apprentice gap is one of the biggest points that I want to make in that book and I genuinely think we need to be worrying about this and working on this right now. And it's a multi layered issue because the AI is taking away some of that foundational work which shaped knowledge and skills and that's no longer happening in that way. But also the knowledge and skills that you need to do the role is changing in ways that we can't yet predict. So to some extent the easy answer is it's a back to basics skills gap analysis, a good old fashioned training needs analysis starting from a blank page to figure out what we need moving forward. But it's not quite as simple as that because it's a moving goalpost because of how AI is changing the future of work. And I think there is a real risk that future leaders will be lacking in some foundational skills that we currently know are essential and they may or may not be essential in future. So it's something I think about a lot, it's something that I try to talk about often. And yeah, thank you for raising that. I know it's obviously as A HR director. It's something that you're going to be very tuned into.

Speaker A: Definitely.

Speaker B: So, Ru, before we come to a close, is there, uh, anything you would like to say in terms of how people can find out what you're up to or connect with you?

Speaker A: Yes, I am active on LinkedIn. If, uh, people and folks want to connect with me, just send me a connection. The request on LinkedIn is aruipashir. Uh, and I'd be more happy to connect and engage.

Speaker B: Fabulous. And we'll make sure there's a link in the show notes for that. I have one final question for you. You knew it was coming. It's the same question that I ask all of my guests. So, Rui, who is a leader you would buy, and why?

Speaker A: Wow. It's Nelson Mandela. I lived in South Africa for 12 years and watched the country he built up close. But the moment I keep coming back, it's not from his presidency. It is from the late 1970s, his 15th year on Robben Island. He started learning Afrikaans, the language of the people he was politically opposing. Those around him did not understand it. They saw it as a strange use of his time. He understood something most leaders never figure out. If you want to change the people you disagree with, you cannot do it from the outside of their worldview. You have to enter it, read, uh, their books, learn their words, understand what they value, understand what they are protecting. He did that for years before any negotiation began. By the time he sat across from the apartheid government in the late 1980s, he knew the political philosophy and the cultural inheritance better than they did. He had earned, um, the right to be in that room and to be heard. That is the move I think about every time I watch a leader try to push something through without first learning how the other side hears the words. Mandela taught me that the most expensive thing a, uh, leader can refuse to do is study the room they want to change.

Speaker B: I think having spent half an hour or so getting to know you, Rui, the fact that you've mentioned a leader who takes the time and attention to understand the difference and the point of view in the cultural nuance and is a great communicator, I can't think of a better person that you could have mentioned than Nelson Mandela. What an iconic leader and communicator. So that's a great example. Thank you. Rui, thank you for coming on the podcast today. It's been an absolute pleasure. Thank you very much.

Speaker A: Thank you so much, Lee. Honored to be here. Uh, and thank you so much for the opportunity.

Speaker B: Well, that was a great conversation and I hope you enjoyed it as much as I did. It reinforced a simple truth, which is that yes, technology can fail, but often if a major rollout fails, it's got more to do with leadership the than the technology itself. And what struck me the most was Rui's point about cultural translation. The same leadership move reads differently in different rooms. What sounds decisive in New York can read as domineering in Sao Paulo. None of that nuance is in the standard AI rollout playbook, and that's where so many initiatives can stumble. The diagnostic advice is equally critical. He said that when two leaders say the same thing, they might need completely different solutions. One might need practical advice and support, the other one might just need to be trusted. Again, if you get the diagnosis right, the help lands better. Get it wrong and you waste months possibly making things worse. The conversation also connects deeply with ideas in Enhanced leadership, particularly around the Apprentice Gap. AI is taking away foundational work that shapes knowledge and skills, while the knowledge and skills needed for roles is also changing at the same time and in ways that we can't really predict. Future leaders risk lacking essential foundational skills, and this is a multi layered issue that needs collective focus right now. If you found this episode useful, you will definitely get a lot from my book Enhanced Leadership where I explore these ideas in depth, including the Apprentice Gap and uh, what it means to lead effectively in an AI augmented world. I'll make sure there's some links in the show notes. You can also find more episodes, articles and insights@levelupleadership.uk where I, uh, publish regularly on leadership development, AI and strategic disruption. If you want to connect with Rui, I'll make sure his details are in the show notes as well and he welcomes connection requests. If this episode has made you think differently about AI cultural nuance, or how you diagnose leadership challenges, share it with someone else who's navigating change right now. These are the conversations that help shape better leadership. Uh, until next time, keep leading, keep learning and keep leveling up. You've been listening to the Level Up Leadership podcast. If you found this episode, that probably means you're a leader looking to level up their leadership game. If that's right, make sure you follow us and subscribe wherever you find your podcasts. We're available on all major platforms. If you subscribe to our YouTube channel, you'll see we regularly have additional bite sized mini clips of the most important points. And if you subscribe to our main Hub on Levelupleadership.uk that's all one word. Levelupleadership.uk you'll have access to the articles that come with each episode, as well as additional bonus articles, some of which are guests or collaborations with other writers. Make sure you follow and subscribe to Level Up Leadership Now.