Whynde Kuehn | How the AI Strategy Trap Derails Trust and Results
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Ep 295 How the AI Strategy Trap Derails Trust and Results

Business strategist Whynde Kuehn joins Bernie Borges to discuss why the AI strategy trap derails trust and results, and why fulfilled employees, not just AI tools, drive real business performance.

Most companies have an AI strategy. Task forces, governance frameworks, a growing list of use cases. And most of them are stalling out, not because of the technology, but because of where they started. Whynde Kuehn, founder of S2E Transformation, has spent decades closing the gap between strategy and execution. Her take on this moment cuts right to it. You don’t need an AI strategy. You need a business strategy that knows how to use AI. That one reframe changes who’s in the room, what questions get asked, and whether your people trust you in what comes next or if they feel like collateral in a cost cutting exercise. And that’s exactly why this conversation belongs on the Life Fulfilled podcast. When employees are fulfilled in their work, they perform better, and that performance is what actually drives the business results leaders are chasing with AI in the first place.

Who This Is For

This episode is for the business leader who is under pressure to show results from AI and isn’t seeing them yet. You’ve got the task force, the governance framework, the growing list of use cases, and still something isn’t landing. Maybe you’re watching your team get faster without getting more fulfilled, or you’re starting to wonder if the strategy itself was built on the wrong starting point. If you’re trying to lead people through this transformation and not just manage a technology rollout, this conversation is for you.

Five Key Takeaways

  1. The AI strategy trap starts the moment AI becomes its own strategy. When organizations build a separate AI strategy instead of tying AI back to the business strategy, they end up with a long list of use cases that never move the needle. Whynde’s fix is simple to state and hard to do: ask how AI expands the value you already deliver, then target use cases against the performance you actually want to move.
  2. The real risk is below the surface, not above it. Bernie calls this the iceberg effect. Above the waterline is everything leaders are already focused on: tools, automation, governance, security. Below it is what actually determines whether the transformation works: trust, clarity, and whether people feel like they’re part of something meaningful or just being managed through a cost cutting exercise.
  3. Human led AI transformation rests on four pillars. Reducing fear, creating clarity, preserving meaning, and building adaptability. Whynde’s addition to this framework is to put the human at the center from the start, not as damage control after the strategy is set, but as part of how the strategy gets built in the first place. Address these four and employees have room to feel genuinely fulfilled in their work, and fulfilled employees are the ones who deliver the performance leaders are counting on.
  4. Three human capacities AI cannot replace. Discernment, the judgment to know what AI output is accurate, relevant, or viable. Relational intelligence, the trust and connection built between people. Purpose driven judgment, knowing why you’re deploying a given technology in the first place. Whynde and Bernie both point to companies rehiring employees after AI didn’t deliver as proof these capacities are not optional extras.
  5. The real competitive advantage is an organization designed to adapt. Whynde’s closing challenge to leaders: what are you doing to intentionally design your organization to sense change, interpret what it means, imagine a new direction, and act on it faster than before? A strong strategy today is not enough if the organization can’t keep adapting tomorrow.

Summary

Whynde Kuehn joins Bernie Borges to challenge one of the most common assumptions in business right now, that AI transformation starts with an AI strategy. Instead, this conversation makes the case for starting with the business strategy and the people inside it, arguing that the leaders who get this right will build not just more efficient organizations, but more adaptive and more human ones. The conversation moves from the AI strategy trap to the iceberg effect to the human capacities no algorithm can replace, closing with a single question every leader should be asking about their own organization’s ability to adapt. Underneath all of it is the same idea this podcast keeps coming back to: a fulfilled employee is a better performing employee, and that connection is what makes the human dividend a business strategy, not just a people strategy.

Learn more about the Human Dividend Assessment
https://fulfilledatworkacademy.com/human-dividend-ai-transformation-assessment/ 

The ⁠⁠⁠Fulfilled Leadership YouTube channel⁠⁠⁠ helps growth-stage leaders replace burnout, disengagement, and turnover with a fulfillment-based operating system without sacrificing results. 

Connect with Whynde Kuehn 

LinkedIn: https://www.linkedin.com/in/whynde-kuehn/
Books & Website: Strategy to Reality and The Execution Challenge
S2E Transformation: https://www.s2etransformation.com/ 

Connect With Bernie Borges

Website: https://fulfilledatworkacademy.com/
LinkedIn: https://www.linkedin.com/in/bernieborges/ 
Instagram: https://www.instagram.com/bernieborges/
TikTok: https://www.tiktok.com/@bernieborges  
Speaking: https://fulfilledatworkacademy.com/speaking/  

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Bernie Borges, Host, The Life Fulfilled Podcast

Music attribution:

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Old Bossa⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠Twin Musicom⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Suno⁠⁠⁠⁠⁠⁠⁠⁠⁠ 

Episode Transcript

Bernie Borges [00:00:00]:
Every company I talk to right now is working on its AI strategy. They’ve got task forces, governance frameworks, consultants, and a growing list of use cases. But most of them are stalling out. Not because of the technology, because they started with the technology. My guest today, Wendy Keen, has spent decades helping organizations close the gap between strategy and and execution. And her take on this moment is direct. You don’t need an AI strategy. You need a business strategy that knows how to use AI and that reframe.

Bernie Borges [00:00:41]:
Sounds simple, but it changes everything from who’s in the room to what questions get asked and whether your people end up feeling like they’re part of something meaningful or just collateral in a cost cutting exercise. That last part is where this conversation gets personal for me. Because when the career pillar of your life is unstable, when you don’t have clarity, purpose, or a leader who’s being straight with you, everything else suffers. This is a conversation about strategy. It’s also a conversation about people, because those two things are more connected than than most organizations want to admit. So in this conversation, we’re going to discuss things like why having an AI strategy might be the wrong starting point, a practical business first approach to identifying where AI creates real value, what leaders owe their people when transformation is underway, and how efficiency without purpose leads to the kind of unfulfillment that we talk about on this podcast, the Life Fulfilled Podcast. Wendy. Welcome to the podcast, Bernie.

Whynde Kuehn [00:02:00]:
It is a pleasure and honor to be here. Thank you for having me. I can’t wait.

Bernie Borges [00:02:11]:
Well, thanks for joining me. I’m excited for this conversation. Let me just give you an introduction. You are the founder and managing director of S2E Transformation. It’s a global consulting practice and you are devoted to connecting strategy to execution. You are widely recognized as an authority in business architecture and the author of two books, Strategy to Reality and the Execution Challenge. And you work with business leaders across five continents. I don’t know how you manage all those time zones, but you help them navigate digital transformation by starting where it matters most with the business.

Bernie Borges [00:02:53]:
So, Wendy, in this conversation, let’s go beyond leadership theory and into what it really means to lead people in a fast changing, AI driven world. Let’s begin, Wendy, with the AI Strategy Trap. What is that?

Whynde Kuehn [00:03:10]:
Yeah, great question. And I think you teed it up really well in your introduction, Bernie. You know, the AI Strategy Trap, I think is born when organizations take a technology first approach. I hear a lot of what are we going to do about AI and what are others doing to AI? Instead of starting with the business. And that’s really the trap. When we have transformative things, organizations tend to create a specialized strategy for them. It seems legitimate, right? So we had things like digital strategies, sustainability strategies. Now we have a lot of AI strategies.

Whynde Kuehn [00:03:52]:
But what we’re really trying to do is focus our innovation, our capacity building, our investment to stand up this new thing. And that’s really what we’re doing with AI. And there are a lot of pieces to put into place. The governance, the data, the technology platform. But that all is important things. But if we only go there and not tie it back to the business strategy, this is where we fall into that trap and can ultimately deliver this set of use cases. That’s a lot of good stuff, but that doesn’t really move the needle for the business. So the key is bringing it back to the business strategy in two things.

Whynde Kuehn [00:04:34]:
The first is with AI, how can we expand the value that we deliver today? What new strategic options does it give us that never existed before? And then secondly, what do we really want to move the needle on? Where do we want to really see increased performance in that strategy? And let’s target the use cases around that to really support the business strategy.

Bernie Borges [00:04:59]:
Interesting. Okay, so there was a third question that I was expecting you to say, and maybe it’s baked in there. So you tell me, Wendy. And that’s the age old question that lives in probably one of the most classic business cases in whether it’s undergrad or graduate school. And that’s the railroad, right? The railroad company who thought they were a railroad company when they sat down one day and realized they’re really a transportation company. So are companies asking themselves what business are we in?

Whynde Kuehn [00:05:28]:
I think you nailed one of the most important things that is not necessarily happening, but that every organization needs to think about. AI doesn’t just help us with the operational stuff. It can help us to entirely reimagine who we are and who we want to become, as you say, and even reimagine the system that we operate within. There’s a book called Reshuffle that I think illustrates this really well. And it talks about, you know, when new technology is introduced, the people that win are those that take on the role of reimagining the system and also, you know, taking on a greater coordination role. So if we just take the example of the Google map, that’s a technology wonderful, but that in itself, itself is not the game changer. Where people really reimagined is, let’s say, creating a brand new ride sharing economy. So you are spot on, Bernie.

Whynde Kuehn [00:06:26]:
It’s time to reimagine.

Bernie Borges [00:06:28]:
So with all of the work that you’re doing across five continents, managing those time zones, working with companies in so many different industries, share a little bit about what you’re seeing inside organizations. What are your observations when you’re talking to leaders? Maybe begin with who are you talking to? I don’t mean names, of course, I mean what roles are you interacting with and then what are you hearing in those conversations as it relates to this whole AI strategy trap?

Whynde Kuehn [00:06:58]:
Absolutely. So C level leaders, business leaders across various functions, Strategy transformation, cio, cto, those are my sort of primary, primary audience. And architects, enterprise architects, business architects, architecture teams. From a business leader perspective, it’s always hard to be a business leader. It’s a massive role to play, but it feels really demanding right now. There’s a lot of uncertainty. There’s a lot of what does AI actually mean? How do we react to this? There’s expectations often publicly, that we do react to that. I think there’s a lot of, you know, not wanting to admit we don’t know what we don’t know, which by the way, nobody can.

Whynde Kuehn [00:07:48]:
We’re all navigating this uncertainty together. And you know, for some leaders, I think it’s, it’s also what’s my legacy going to be as I lead this company through this next change? Are we going to be the blockbuster or the, you know, the, the Kodak case studies out there that didn’t navigate this shift? So it’s a lot of pressure. And Bernie, I also will say I just delivered a two day C suite leadership program and every single one of them, they’re balancing this and that, meaning I’m managing and leading a business through a very hard time with supply chain disruption, geopolitics, you know, lots of increasing change while also trying to have to really transform the operating system of my company to be able to be adaptive and where I need to be in the future. So it’s, it’s both of those things and it’s, it’s a tricky time to navigate, but also very exciting because the opportunity is unprecedented.

Bernie Borges [00:08:49]:
Now, Wendy, we are having this conversation on the Life Fulfilled podcast. And as you know, I come at it through the lens of the impact on people. And so let’s talk about what I’m calling the, the iceberg effect. And I’d like to know to what extent you’re seeing what I’m seeing when I am out there doing what I’m doing and I’m talking to leaders the iceberg effect, as you know what I mean by that, and that is that leaders are looking at what’s above the surface. Hence the metaphor of the iceberg, which is to focus on the tools, the automation, the governance, the security, the desire to deliver results. That’s above the surface. But below the surface are human issues, people issues. I’m seeing a lot of that.

Bernie Borges [00:09:44]:
Are you seeing that?

Whynde Kuehn [00:09:46]:
I am the same. And I think the way you articulated it gets right back to what we talked about as the AI strategy trap. Feels like we’re doing the right things, we’re focusing on the technology, the governance, the above, the, you know, the waterline things. But it’s the people, it’s the clarity, it’s the purpose below that makes this work. And you know, it’s how is this organization designed to deliver what it’s going to deliver? Those are the things we don’t think about when we just look at the top. I also think, Bernie, and this is very much related to fulfillment. I know there’s a lot of conversations on, you know, people losing jobs and automation and a big concern there. And you know, as I said before, I think going into this era and not rethinking your strategy and just assuming you need to, you know, automate jobs away is not the right way to look at it.

Whynde Kuehn [00:10:41]:
There’s a lot of strategic options there. But I also think there’s so much possibility to create even better purpose and value with our organizations and to restructure our organizations more around self management, more empowered people. That’s the big opportunity, really use it to unlock all of that in a very different way. Not industrial era people are cogs in a machine, but sort of organization as living organism.

Bernie Borges [00:11:11]:
Okay, now you’ve really got me going, Wendy. Now you’re talking my language. Because look, history is full of examples of industries that have been disrupted and reinvented and evolved into a new version of the industry. One of many, many examples is the horse and buggy industry went away, but the automotive industry became a humongous industry that created lots of jobs. And there’s many other examples. That’s just one of the more obvious ones. But on the human side of where we are right now, I think we’re at sort of an early pivot stage in the adoption of AI. And this is what I’m seeing.

Bernie Borges [00:11:53]:
And I want to get your perspective on this because when I talk to leaders, I talk to them about what I call human led AI transformation. What I encourage leaders to do is to acknowledge that there’s fear in the employee population. So one objective should be to address it and to reduce the fear. And another one is to give clarity to the employees of what their role is, what their job is, what the expectations are. And then a third one is to give employees the ability to preserve the meaning that they have with the human capacities that they bring to their job. And the fourth one is what I call building adaptability. And that’s communicating the expectation that, you know, the company is not going to transform, become AI literate or AI anything overnight. It’s a process and we have to be willing to adapt and not just declare ourselves an AI company overnight, whatever that means, but to have a process that is adapting over time.

Bernie Borges [00:12:56]:
So those are sort of the four pillars that I’m communicating to leaders, and I’d love to get your perspective on that and how those conversations are happening in your world.

Whynde Kuehn [00:13:07]:
Yeah, I think those are beautiful. And the only thing I would add is put the human in the center right in the beginning. That’s where I say, rethink your purpose, rethink your business model, rethink your strategy. And I’m not naive. I understand all the pressures, particularly public companies, and we have to make profit and we have to, of course, do a lot of things, but it also gives us this chance to really reflect and say, what’s the role of business in society? And if we’re not doing this for people, what are, what are we doing this for? You know, who, who buys our products and services? And what if we thought about organizations as not just value creation for customers, but also the people that work within them? So I love everything you said, and I just also think this goes even more so right to, right to the heart. And I will also say, as we’re making change, I like the very like, honest, open, you know, way that you describe that. I also think there are a lot of disciplines out there that are really good, like human centered design and organization design and organizational change management that I find are often afterthoughts. They need to be right there in these conversations and strengthened to be able to help people through this change.

Bernie Borges [00:14:30]:
Yeah, because a lot of people in the workforce are struggling with this demand, this sort of declaration of we need to be more efficient, we need to be more competitive, we need to, you know, expand our market share. Those are all business goals. But back to what you said earlier. If I can kind of maybe paraphrase the. The meaning of what you said, and that’s what’s the purpose behind it? What’s the purpose of us driving all that efficiency, if it isn’t meaningful to both the business, because it has to be good to the business, as you and I both acknowledge, but also to society, what is the purpose of that? And when employees feel like they’re given AI tools to become faster. Right, Wendy? To be able to do more in the same amount of time than they might go home at the end of the day or at the end of a week feeling like all I’ve done is just gotten faster at my work. I’m able to do more work, but I don’t feel any different in my contribution because I’m being asked to do is to do more and more of it because I’ve got tools to do that. Most AI initiatives don’t fail because of the technology.

Bernie Borges [00:15:53]:
They fail because leaders don’t plan the human side. There’s a fear tax and a meaning gap that’s draining your team’s performance right now. And most leaders don’t even know it. Our Human Dividend assessment measures both across four reducing fear, creating clarity, preserving meaning, and building adaptability. It’s a structured diagnostic that you take online a alone or with your team. It includes a debrief call, a custom report that’s built around your team, and specific next actions that turn insight into ROI for your business and your people. To learn more about the human Dividend assessment, visit the link in the show notes.

Whynde Kuehn [00:16:42]:
And Bernie, this goes right to your I believe your human dividend point, which I think people aren’t talking about. And I love that you bring this up because there’s two parts of this. One is purpose and when you are connected to purpose. And like you say, we’re doing meaningful work, we’re going to be better employees and that business is going to work better and we’re going to have retention and all those good things that we know that we want. This to me is also under the iceberg. This stuff has to work because unhappy, unfulfilled people are not going to be driving right as the results that we want. But the other part of this is what do you do with that extra time? And if you just feel like I just only got more work and I’m just. Even as the work shifts, you know, I asked myself how interesting is human in the loop and you know, like just reviewing stuff.

Whynde Kuehn [00:17:31]:
So I think we have to really think hard about how the work shifts and how the roles shift as well in meaningful ways and what we do with the extra time.

Bernie Borges [00:17:43]:
Yeah, there are more and more examples. I just read an article this morning about a big company, big brand, global brand, who rehired a bunch of employees because they weren’t getting the results that they expected to get with AI. And they needed to bring all those humans back to provide all of that expertise that those humans have up here in their head, not only from an intelligence standpoint, but from an experience standpoint, because it wasn’t happening the way they were expecting it. And that really leads me to what I call the three irreplaceable human capacities. And one of them is discernment. Knowing what questions to ask, knowing what information you get from AI that is or isn’t accurate, or is or isn’t relevant or meaningful, or is or isn’t viable. That’s human discernment and also relational intelligence. Wendy, you and I working together, that’s a relationship.

Bernie Borges [00:18:37]:
And AI is not going to do that any better than you can. You and I can do that, or a group of us can do that collectively. And then the third one is purpose driven judgment, and that’s really just being able to deploy technology for a specific purpose and not for the sake of technology. These are irreplaceable human capacities that I just. I want leaders to embrace these because they’re too blinded by the sex appeal, if I can use that metaphor, of what they think AI might do. Like this story that I just briefly mentioned of a company that rehired because they thought the AI was going to do more than it really could.

Whynde Kuehn [00:19:18]:
And I love that story so much because it reminds us, slow down, take a conscious pause, figure out the right thing to do so that you speed up later. That example has brand impact. It has financial impact, it has employee satisfaction impact. Feel, think about how it feels to be an employee rehire. I mean, so those things are, again, below that iceberg, and we have to get them right.

Bernie Borges [00:19:50]:
So what do you think leaders can be doing, should be thinking about during this time? What I’m hearing you say in this conversation and other conversations we’ve had outside this podcast is start with the business strategy. But you and I, in this conversation, in addition to that, we’re talking about the people strategy as well. What do you think leaders should be thinking about as it relates to integrating the people strategy into the myriad of challenges that you had? Because you said earlier they’re faced with a lot of challenges. You listed several of them, and we need to acknowledge that, but we also can’t ignore the people side of it. So how do you encourage leaders to actually make sure that that’s in the mix?

Whynde Kuehn [00:20:36]:
Well, when I think about unpacking strategy. There’s sort of a key connecting glue there, which is capabilities of the organization. Strategy requires capabilities, things that organizations are good at, like customer intelligence, customer insights, things like that. So if we can understand the capabilities we need to be good at, we understand that capabilities are enabled by the people, the process, the technology that gives us a focal point. I think one of the biggest things that leaders can do is actually be intentional about the design, design of what the future organization looks like to carry out an AI enabled strategy and what the people, right, what the people layer like that, what the people layer is going to look like. There’s a lot of, here’s generally where we’re going now. Everybody create your laundry list of initiatives sort of in a very siloed way. And that’s kind of where things go sideways.

Whynde Kuehn [00:21:31]:
So it’s just really kind of being methodical about strategy to capability. And what does the future state design look like? Then we execute together.

Bernie Borges [00:21:39]:
Do the human skills then become even, even more valuable? I, I, I mentioned, you know, the, the three, right. The, the discernment, relational intelligence, purpose driven judgment. Those are all human skills. I mean in my mind is, I think it’s a rhetorical question. They become even more valuable because the technology, when used with technology, they’re powerful. But, but without the technology or the technology without those human skills is, is an incomplete puzzle in my mind. Your thoughts?

Whynde Kuehn [00:22:12]:
Absolutely. And it’s almost, it’s a mechanical, right? We want the experience, we want the human interaction and we want the human creativity and discernment. You know, I almost think about, and I think this is a good thing and in some respects AI is going to force us to become even better. Right. If we kind of look at a pyramid, right. So AI is automating a lot around operations and development and things like that. Well, that leaves us to the top of the pyramid, how we design the system. System, right.

Whynde Kuehn [00:22:45]:
I’m meaning the organization and business ecosystems and then strategy and direction. So who do we want to become and what are the options? So to your point, the human is even more important not just for relational experience, but to do the really smart stuff and continually to decide who are we going to become, how are we going to evolve? Because AI and our whole digital connected world is making everything move faster. Our strategy has to move faster. We have to react all, all of that so much quicker and make decisions, right. And translate them into execution quicker than ever before.

Bernie Borges [00:23:20]:
So as we come close to wrapping here, we’re not there yet. But what would be one overarching question that you think leaders should be asking themselves as it relates to AI transformation as they’re again leading through multiple dimensions of challenges. What’s one overarching question leaders should be asking themselves?

Whynde Kuehn [00:23:46]:
Only one, Bernie. No.

Bernie Borges [00:23:49]:
Can be multifaceted.

Whynde Kuehn [00:23:51]:
That’s right. Exactly. Multiple parts. Well, we’ve talked about the capability driven AI strategy and we’ve kind of talked about legacy and being intentional, you know, about the company that we’re building and what we’re doing with our people. So I would ask the question of what are you doing to intentionally design your organization to be adaptive? Because I think that is going to be even more important tomorrow, as I was just alluding to a brilliant strategy today. Fine. But we have to be able to react and change to all sorts of different possibilities that are going to move at lightning speed. And so an organization that can sense what’s going on, interpret what that means to them, imagine new direction, and then be able to decide what to do and translate it into action.

Whynde Kuehn [00:24:46]:
That is a muscle we all need. And I think that is a new competitive advantage. So again, the question is, what are you doing in your organization to intentionally design it to be adaptive?

Bernie Borges [00:24:59]:
So I totally agree. I’m going to. Yes. And you.

Whynde Kuehn [00:25:03]:
Yes.

Bernie Borges [00:25:04]:
So, so, yes. And think about the people strategy. What are the old famous Jim Collins quote, right, from his book Good to Great, you know, what are the right people on the bus from a skill standpoint? What are the skills that the business has today and the skills that are needed over the next two, three, five, ten years? And because what I’m also hearing, even though we, we hear a lot about people losing jobs, but I also hear a lot about skill shortages, companies that have open jobs that they can’t fill, as well as new jobs that are being created as companies are going through this AI transformation that they didn’t anticipate needing and now they need to move people into those jobs, Wendy. And maybe some of those people didn’t previously see that in their career path, but because of the adaptive nature of this whole AI transformation journey, it’s reality, it’s happening. So I think leaders need to be thinking about the people skills. And I think there needs to be executives that are constantly thinking about that. What are the people skills we need this week, next month, next quarter, next year? Maybe you can’t look too far, far how much further out than that. But having that top of mind, I think is a critical question to be asking.

Whynde Kuehn [00:26:32]:
Well said, Bernie. And drawing attention to the fact that it’s not just about job loss. It’s job creation and adaptive reimagining and there’s a lot of that. And those are also good stories to draw attention to.

Bernie Borges [00:26:45]:
Exactly. Wendy, this is a great conversation and I know we’re going to continue it. In fact, fact, I’ll do a little bit of teasing here. I know you and I have talked about maybe doing a webinar on this topic. So more to come on that at another time. But for now, why don’t you share with my listener how people can connect with you and learn more about you and get into your world.

Whynde Kuehn [00:27:08]:
Yeah, I’m open to connect anytime. Contact me on LinkedIn. Wendy Keen. Very easy. And I also have two books, as you mentioned, Strategy to Reality, the Execution Challenge. You can find find those Amazon and all sorts of places or on website S2E transformation.com Thank you, Wendy.

Bernie Borges [00:27:28]:
All of that is going to be linked up in my show notes. My listener knows that. And I just want to thank you for joining me today for this conversation. I love this conversation. I think it’s only the beginning. I think we’ve only begun this conversation. There’s a lot more to be had and I’m excited to continue it. So thank you so much for joining me today on this episode of of the Life Fulfill podcast.

Whynde Kuehn [00:27:48]:
Thank you so much.

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