Founder's Story - The Costly Mistake Leaders Are Making Right Now | Ep 313 with KeyAnna Schmiedl Chief Human Experience Officer of Workhuman

Episode Date: February 24, 2026

Daniel Robbins interviews KeyAnna Schmiedl of Workhuman about the growing fear of AI in the workplace and why leaders must stop treating AI as a workforce replacement strategy. KeyAnna shares a practical, human-centered roadmap for adoption, arguing that people are the true differentiator in a world where companies may all have access to similar AI tools. Key Discussion Points:KeyAnna explains that many organizations are making a foundational mistake by investing heavily in AI technology while barely investing in the people expected to use it, citing a 93 percent versus 7 percent imbalance discussed in the episode. She argues that leaders should involve employees in defining where AI can reduce friction in their day to day work, rather than forcing top down solutions tied to layoffs and short term margin pressure. The conversation also covers how CEOs can move from being “careful” to “thoughtful” with AI by allowing responsible experimentation, learning from real usage, and avoiding overrestrictive policies that slow progress. Daniel and KeyAnna then explore what great culture looks like today, emphasizing transparency, employee voice, and trust building during times of high skepticism. In a powerful personal reflection, KeyAnna shares how authenticity, humility, transparency, and curiosity shaped her leadership journey and helped her grow into a role she once viewed as almost unimaginable. Takeaways:This episode makes a strong case that AI adoption is ultimately a leadership and culture challenge, not just a technology rollout. KeyAnna’s message is clear: organizations that treat people as a cost center will miss the real opportunity, while those that equip and include people will create stronger innovation and better outcomes. Leaders can start immediately by sharing where AI is working, where it is not, and normalizing experimentation across teams. Her framework around thoughtful leadership is especially useful for executives navigating board pressure, layoffs, and uncertainty. The episode also offers a deeply human reminder that curiosity and consistent authenticity can open doors that once felt completely out of reach. Closing Thoughts:This Founder’s Story conversation stands out because it blends practical AI leadership advice with a deeply personal leadership philosophy rooted in trust and transparency. KeyAnna leaves listeners with a more optimistic view of the future of work by showing that the companies that win with AI will be the ones that invest in humans first. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

So, Kiana, it's great to have you here. I think we just had a phenomenal conversation about our experiences recently at the World Economic Forum in Davos, Switzerland. And I was so sad that I didn't get to see your talk there at the Wall Street Journal House, but I've heard it's incredible. And I saw also the other places that you spoke like female quotient. And I know you talk a lot about AI in the corporate environment. And from what everyone I know that's in that environment, they're telling me all the same thing. There is this massive AI anxiety around, is AI going to replace them? Is AI supporting them? But also, I'm not sure of leaders are truly explaining because I don't know if they know, right, the full benefits of AI, but are they really explaining to their teams how this can be a supplement and support versus replacement? So, one, thank you so much for having me here. again, I really need you to work on that Delorean so you can go back and know me then. And then we can catch up on all the things that apparently I missed out on at Davos because there is a lot to do but also a lot to miss. To your question, though, look, I think some really interesting research was put out by Deloitte, I want to say, in December of last year.

And essentially what it said was all of the spend, right, billions of dollars in spend was being put into the technology versus the people to the percentages of, I think it was 93. percent investment in technology and AI and only 7% investment in the people. If you have not already started, this is your wake up call to make that shift, both in terms of theoretical investment, but also in actual investment. The reason why we've been seeing so much money put into AI and now this question of, is there an AI bubble, is because we haven't focused on the people first. The people are the ones who are going to leverage the tools to either see the productivity gains, or not. And by not starting with them, you're not giving them an opportunity to co-define what success looks like. And instead, so much of what was talked about was AI should mean that we can

decrease the workforce by X percentage of people. And you saw that happen with layoffs because now we have AI. But you're also not seeing those productivity gains. And in a lot of areas, it's just not the kind of golden arrow that everybody thought it was going to be. I will tell you it still has the chance to be, but only if you get your people involved. Your people know better than you, better than me, what they are doing on a day and day out basis that are inefficient. They know the places where if you gave them the power, they would fix this tomorrow. And so you need to be empowering them to leverage the tools to fix the things they would like to fix in order to feel better about their jobs, which then makes them better at their jobs. So it's got to be more a conversation

with the people and saying what technologies, how would you like to use that? Where do you see in efficiencies? And then really gearing your solutions towards those things. I'm glad you bring that up. I mean, 7% about the people. I can see that. There's not a lot of conversations really about the people and how do you get them to even be comfortable? Besides the fact that they have so much to do in their job, they now have to learn something and do something on top of it. But I think you and I know at least for me, the learning curve is not that big. I mean, me, my team, we use so many tools on a daily basis. And it doesn't take that much time because they can do so many things now with like,

remember it was like you need to be a prompt engineer before now. You just write a sentence. It's so easy. So what would you tell to leaders? Like what can they do right now? Is there something a step they can take so they can get started? Yeah. One is share where you're using it.

and where you're seeing it work, also share where you've tried it and you saw it not work, right? I will tell you, nobody is dreaming of their future being a prompt engineer. They're dreaming about what about their job gets better because they have AI working alongside them. How do they get to be more of themselves, more creative, et cetera? And so those are the examples that leaders should be giving. I will tell you that we had a leadership team retreat for my team last year, and I asked everybody to go around and raise their hands if they were using any, you know, GPT, if you will, whether it's chat, GPT, whether it was clod, whatever it was. And you saw people looking around at each other.

And I raised my hand to be like, look, I'm trying to push myself on more AI first drafts because I'm a much better editor than I am the person to write the thing. always be too lengthy. It will be too wordy. Half the time I'm kind of just finding a different way to restate the thing that I already said. But to whittle it down from a good starting point is where I feel like the sweet spot is for me. And also it taking away that time. Now, do I need to get better at prompting so that I get there faster? Sure. But am I over agonizing on becoming a prompt engineer and putting in the perfect prompt also no. And so I think that some of the shift is a little bit more subtle, but it's also putting out there, hey, here's where I tried this and it just did not work for

me, but here are the places where I'm going, I absolutely will be using it in this way. And now we have jokes on the team about whether chat GPT will be our Lord and Savior and if we need to actually tip it or say thank you for the time when it takes over. But when you get people more comfortable with this is another tool in the toolbox, then you're going to see them get comfortable with also sharing, hey, here are some of the benefits that I've found. And you just got to think of it as like broadening the skill set across the team, right? If I'm here as the leader of a team, my job is not to know an intimate detail down to, you know, the grass seeds exactly how to get these things done. It's to make sure that we have the right people on the team who know those things, that when you

combine their skill set, we get lots more done. And this is just another tool in the kit for people to use to broaden their skill set and to be able to partner and collaborate more effectively and more efficiently. When you think about it like that, then it's easier to think about, so then how do you integrate a new technology? How do you think about how processes shift when all of a sudden these things become more efficient? And it's less about then measuring productivity as an output of how much time is gained. And instead, measuring the end goal of what got accomplished. And that's always what gets people excited.

We're going to go tackle this big thing. Let's chunk it up and let's go accomplish it. And I think having more of the conversation that people are used to for transformation, for change, et cetera, is the way that you just start to embed this more into it feeling like an everyday thing as opposed to an existential threat in a sink or swim for the business. I'm so glad I didn't go back and get my four-year prompt engineering degree. So I know you specialize in moving leaders from careful to thoughtful. How do you see a CEO being thoughtful around AI?

Because we already know a lot of times they're under immense pressure around bottom line, right? Like they are under pressure almost. I hate to say it to replace people to increase profitability. and we know people many times are like the biggest expense and cost for many companies. So how can a CEO be thoughtful around this? Look, I think what's helpful here is probably giving a bit of the definition of how I think about careful versus thoughtful that then probably answers your question, but I'll go further. So to me, careful is let's think about all the ways this could go wrong and put in all of

the policies to ensure it doesn't go wrong. Thoughtful is, look, there is some amount of risk here. It's good to have a general sense, but we know that it's risky. If we just work with it and then start to see how people are using this and where there is some risk, we can flag that early enough that we don't scale the bad, but also that we're not hindering the good, right? That's a more thoughtful approach. It's like, let people try it.

If we believe that intention is always good, it keeps the business in mind, then let's see where they start to go with this and then say, oh, okay, hold up. let me pull you back there as opposed to assuming that they can only have a thin slice of lane to go down. And so when we think about this with AI and what CEOs can do, I think it's having the conversation with the board to say, the first thing that we need to do is invest in the tools and technology for the people to use right now. And then give that a year, give it 18 months and see where we're at before we can have any truly intelligent conversations about what are the net gains here. If you think about it as people are the largest cost that a business has, okay, what happens when you cut out the people?

You don't have a business. And so we need to stop thinking about people just as a cost, but actually as the engine that moves a business forward and that denotes whether it's going to be successful or not. Because in the equation of humans plus AI, across every business doing a similar thing with the similar AI tools, humans are your differential. your people are your differentiator. And so this is where the intelligent, thoughtful conversation needs to come in about what's reality versus where do you just brute force something in and how often does that actually work for you? And what happens if you do that here? You're starting to see

articles now asking organizations, are they having regret about some of the layoffs that they've had, especially in places like engineering, et cetera? I don't know whether or not, they do or whether or not they should, but I'm telling you right now that the shift needs to be who are the people that are here that are making a difference every day and how do we continue to give them the tools so that they can differentiate themselves that then differentiates our business. I really like that idea of not using people as a cost, but really using people as an added benefit to the organization. It's like it's like the added revenue because if there's no people, I mean, how will you get revenue?

How will you get anything done really at the company? As of right now, AI agents can't replace everybody in this current moment. Right. And I mean, think about that if they did. Right. So think of a scenario in which it's like, oh, it's all AI agents here. Do you really think you're going to get the same level of innovation that you get with a mix of technology in people? Absolutely not.

So I think it's flipping the conversation and honestly pushing into a conversation. that I believe people people, HR, chief people officers, talent leaders, whatever you want to call them, have been trying to have for years, which is stop looking at how much your people cost, start looking at what business your people are driving. And is there a delta between what they're doing and where you need to see the business go? And then how do you solve for X? Yeah, I mean, right now, AI just tells me everything I want to hear where people, I want them to challenge me. I want them to tell me things, not just what I want to hear. I know you've, you've led culture at massive brands throughout your history. And I, I wonder nowadays how,

like before how you looked at, okay, this, what was your gauge of like, this was a great culture to now, this is a great culture when we think of not just technology changes, but generational changes, different people of different ages now coming up into the workforce. Was there a difference between then and now and on top of that, like what made something a great culture? Yeah. Look, at the end of the day, I would tell you that it's whether or not people feel like they have a stake in a say. So people want to feel connected to the work that they do, whether that is ensuring during the

pandemic that folks who had homes and living spaces were able to create the spaces that allowed them to be the most efficient with their time, depending on what all they were doing, or whether that's, you know, my finances are in order, or whether that's, I feel good about the work that I'm doing every day. And I feel like my company sees me and appreciates what I'm contributing. And so to me, it's about where are you, again, being thoughtful about the places where leaders, should not be trying to he-man something over onto and imposing something onto the people, but rather putting the question out there or putting the thought out there of, it seems like we're needing something right now.

I'm not exactly sure what that something is. I've got ideas, but I want to know from you all where you have ideas and let's build something together. So when I think about that, I think about, you know, my time at Wayfair and when we created the change starts at home conversation. That wasn't a dictated by leadership. It feels like our people need something and it needs to just be a conversation. And then if they want to define what the asks are, they should be allowed to do that. And then for leaders to take that, digest it and respond. Right. Similarly here at work human in this moment that we're in right now, when I think about

things like the hackathons that we have, it starts with what are the ideas that people have. not what does tech say have to fit the right parameters or what does the business say beginning with these ideas that we've prethought of that we think will get us that will earn us additional business but rather what are the things that are interesting to people right now that they believe if we were able to solution for them it would make their job easier it would make things move smoother in the organization which then at the end of the day if you extrapolate that out, then means better margins for the business, right? A better business outcome. And so the more you can involve your folks so that you know how they're thinking about things,

where there might be a gap between their understanding and how leaders are thinking about this, it then allows you to close those gaps. That does not always mean that you're always saying, yes. But I think the more you share transparently, here's what we're hearing. Here's how we're then thinking about this as a business, here's where we want your voices to help shape a solution, then the more wiggle room you have in those moments where it's like, I hear you, the answer to this is no and here's why, and people will trust that, as opposed to thinking about they didn't really care about our opinion, they just wanted to say that they asked us, right? And so in this time of heightened insistence on AI as a technological solution, you have to imagine that there's heightened

skepticism about the why behind that. And so are you meeting your people in a place of high skepticism to continue to build and scale that trust that you're going to need to move your organization forward? Exciting times. I was kind of pessimistic before our conversation, but now I feel I feel genuinely more optimistic. So I appreciate that. I can't help but think about in my time when I worked for larger corporations, as I continued to move up, I had to adapt and change a lot of things about myself, how I went about things, how I said things, how I showed up. For you, I mean, you've obviously had an incredible career. And I think a lot of people would look at you and say, wow, like you inspire me. I want to be like you one day. I want to get

to the level you're at. What did you have to change within yourself or how you went about things as you moved up? Well, I'm going to answer this honestly, but I'm also mindful that it may not land well, and so I'll clean it up on the back end if I have to. Honestly, what I had to be open to was hearing from people what they thought some of my superpowers were. Like most people, I am my own biggest critic. And so I will always tell you about the things that I think I could do better. And I'm happy to tell you about the millions of things that I believe I got wrong, yet still somehow I'm here. Right. And so other people have been able to call out to me the things that they think I do well or naturally that are a different definition of leadership

skill set. And so what I've come to kind of define those things as are, you know, my foundational ethos or my key principles, which is authenticity, humility, and transparency. It's really important for me that folks understand where I'm coming from. The way that my brain works, sometimes I think it's very unique, but the more that I connect with people, the more I understand, no, there are a lot of folks that think in these ways, but it's just not always clear. And so me doing a better job of articulating that, here's what's behind that thought. Here's why I'm asking or actually, even though that sounded like a statement, I meant it more as a question that's open to pushback, is so that folks understand where I'm coming from, because that allows me to authentically show up as

myself, no matter what conversation I'm in. The way that you and I are talking right now is the same way that I talk with our CEO is the same way that I talk to our new hire employees when they join. And that's really important for me to feel like I'm consistent in how I show up in various discussions so that people don't feel like they have to read the tea leaves to understand what did I really mean by that. And that's the transparency piece, right? I think the humility is also just admitting where I get things wrong. Sometimes I'm a little bit too quick in rotating on a decision and going, okay, I think this makes sense. And then as I think about it a little bit more, I'm like, you know what, I do still think that makes sense, but I think there are other ways to go about that.

I tell people that when I get it wrong, I will go into our HX global team Slack channel and be like, hey, y'all, we got really excited about this thing. I presented it and I didn't have all of the information, which has caused some confusion. Let me step that back a bit. Here's what I promise to get to you in this timeline. We're all going to get things wrong. That is okay. I am more concerned about the people who get things wrong and then feel like they have to cover it up and make it still seem like they got it right, because those are the things that will get us in trouble. At the end of the day, we're all trying to do our best work, but it's about matching those intentions to the impact that you're having and understanding where those two things are

different so that you can make it better than next time. And I think being open to that allows you to become more of a holistic leader than you think because I will never have all of the answers. But I make sure that I surround myself with people who I believe can get us to the right answer. I can tell that you are authentically real. And I have also been told that I have a unique brain. I don't know if that was a good thing when they told me. However, though, not everyone gets it, but when they get it, though, they get it. And I appreciate that. My final question, I wrote this book here, unlimited possibilities to talk about the things that I thought about when I was a kid, teenager, young adult, the dreams I had and then I was able to accomplish those dreams.

What for you, when you look back to when you were younger, what was what you would say was an unlimited possibility that you, you know, it's so big that you didn't know if it would ever even come true, but at some point it did. Okay. There are two ways for me to answer this question. The first is, I think growing up the way that. I did in a black family that was one of a handful of black families in the town that I grew up in meant that from an early age I can pick up on when sometimes just my presence itself made people

uncomfortable. And additionally, where they weren't expecting much of me, where they may be expecting more from my peers. And so that allowed me to maybe more fearlessly question why and how and what. then my peers would feel comfortable doing, right? And so I think being insatiably curious and having more of a systems thinking mindset means that I feel comfortable asking the questions that on the surface may seem like, shouldn't we know that? But really what's meant by them is, are we all on the same page about this? Are we picking up similar signals?

And that helps a group to recalibrate or at least feel like they can recalibrate. I think the second thing is, look, it's going to sound cheesy and people are going to be like, that's BS. I promise you it's not. You can call back into LinkedIn posts. I remember showing up to my first work human live and seeing their head of people on the stage interviewing. I can't remember exactly who it was and I don't want to get it wrong. But they were interviewing someone. And I was like, how do you even get that job? Like that I can't imagine how you get that job. It seems like the perfect job. It is wild that roles like that exist. I didn't say to myself, I want that job.

I said, how do you even get that job? And I'm sitting here right now. That's something that on a fairly consistent basis, I wake up and I go, I don't even understand how this whole exists and how I am in it, but I am going to try my best to keep it and to make good happen on a regular basis. So I think, listen, don't be afraid of where the question just kind of leads you down a path that actually may lead you to the thing that you never thought was possible. I wasn't the type of person that dreamed about my career will be this and I will get married

and have children. I will tell you I'm married. I have children and I have a great career. I did not think any of that was in the plans for me. It was just about making decisions that made sense, maybe scared me a little bit, but also made me feeling like I was doing something worthwhile day in and day out. I love that. Your curiosity and I can tell that I'm always a big proponent. I feel like I'm the same way. Curiosity I think really drives people more than what other people believe. And then the fact that

you saw something and that you were able to then go do that is incredible. I mean, chief human experience officer. That's incredible. Work human, but Keanuidel, This is amazing. If people want to get in touch with you, how can they do so? They can reach out to me on LinkedIn. I'm at Kianna Schmeadle. I'm not really on the socials because I like real, true connections in space and time. So I am hyper responsive if you reach out. Otherwise, if you have my email addresses, reach out to me. I'm happy to connect. I'm happy to connect you to others. Whatever makes sense. Well, thank you so much for joining us on Founder's Story. Thank you for having to see you in 2027, Davos. That's right.