Inside CTOx with Yoemy Waller (Part 2) (Final).m4a Mon, Nov 17, 2025 0:00 - Yoemy Waller You might be this close to getting a solution for somebody, but if you don't Read that book or you don't figure out what was in that article or something like that, you might miss it. You might simply miss it and have months and months of struggle when somebody else already found. 0:17 - Donna Welcome back to Part two with Yoemi Waller. In the first Part, Yoemi shared her journey with CTOx, gave us some great advice, and we continue to dive into AI, her leadership advice, and as always, our special Chat GPT question. Enjoy. 0:34 - Yoemy Waller I've been, you know, in the industry for so many years. Most of the time was working for somebody else, right? For the last past 10 years, I have been working on my own. Sales process is very long because the healthcare industry takes a lot of time. They might want your services, but they have to wait for the next budget cycle to be able to get you in and things like that. Found Lior, and it seems like everything clicked. But also understanding that you have to get out of your comfort zone. If whatever I'm doing is not going to provide any benefit, what is it? Then it's no use for that. If I'm going to be able to save somebody's life, if I'm going to be able to predict that somebody might get sicker and you have to do some intervention, if those things are meaningful, right? So it's Part of that understanding that it's not just technology per se, it's also what are you serving that technology for? 1:35 - Donna Yeah. And how has AI influenced your leadership in this past kind of year or so? 1:41 - Yoemy Waller I think that I have become, I wouldn't say cautious, but I have opened my eyes to understand I may not have the answers. I might have to reiterate something or I might have to change something to try to find that answer. Nothing is infallible, right? Not even AI. So you'll get to be able to understand and be humble enough to understand we try it this way. You got to do it somewhere another way because this is not getting want to go, right? You know, it's like Alexander Graham Bell. How many prototypes of the telephone he did? Thousands and thousands and thousands. So everything is like that. It's an evolution process. So the same, that technology and AI is evolving and it's evolving really fast. And some people think that because it evolved, it's already going to solve all your problems. Not necessarily, right? It might improve the way you work today. It might improve your outcomes, but it's not the cure-all, fix-all, tomorrow nobody's sick, and all that kind of thing. It doesn't happen, right? And managing and having the leadership to manage those expectations is key. Because, you know, for the people that are totally excepting, then you say, okay, let me help you understand what's going on. And to the people that are, go home, let's do this, everything AI And it's like, wait, hold on. You can't just jump in the water like that. So it's a lot of managing the expectations of people in the technology field, and also understanding the capabilities of the technology itself. Because somebody that is just too accustomed, and that happens a lot for technologists, they are going to, oh, the next shiny thing, now I got the new thing, and it's, you know, it's super duper and everything will work. Not necessarily, right? Especially in the field that I am, which is healthcare, you cannot just jump like that. Oh, let's use the latest and the greatest because it might not be the greatest. So it is that process and iteration of understanding what this tool can do for me. Is it really so maybe I have to do some tweaks because it might not be the actual solution that I'm looking for. So it's that process and having that humility to make it happen without feeling betrayed, right? It's like, no, you got to work with it. It's not like magically things are going to happen. 4:34 - Donna No, and you're right. The leader aspect of it, I think, is so important. And that's really what we try to do here at CTOx is take those CTOs and be like, your leadership is now more important than it's ever been. Exactly. Since the invention of the internet, this has been the most crucial moment for CTOs. So, you know, it's not just about, to your point, it's not just about the technology, but it's like, how do we manage people, manage expectations? You know, how do we stay humble? How do we treat this? Manage the client. Manage the client. Of, yeah, there's so many factors to it. And all of that is leadership, um, with, with, with background in technology. And that's why I know one of our most, I think popular is the level up leadership with Lior, where he looks into this and a lot of his advice is exactly what you're saying, which is like, yeah. You know, sometimes you're not going to know everything and that's okay. It's not that you have to know everything, but it's like, you have to be able to lead, lead people, the people above you and the people below you and the and the clients and all the different aspects, but being that leader is... 5:41 - Yoemy Waller Absolutely, absolutely. And I always believe that you got to understand that you don't know everything. I always have this thing like, maybe I don't know something, I got to figure it out, right? And being that constant quest, you know, for more information, to better understand to figuring things out. Because you might be this close to getting a solution for somebody, but if you don't Read that book or you don't figure out what was in that article or something like that, you might miss it. You might simply miss it and have months and months of struggle when somebody else already found the best way to do it, right? So I'm always, to me, it's super important. Also Part of that leadership is the learning. You never stop learning. 6:38 - Donna Yeah, that's why we're in a program here. All right, well, speaking of AI, this brings us to our Final segment. This is the most fun I get to have. And Yoemi doesn't know anything about this, neither has the previous guests we've had on. So a little nervous. I feel a little nervous here, but don't worry. So I'm going to ask ChachiPT live right here, right now for a question generated on the spot. I don't know what it is. You don't know what it is. We're just going to ask. Um, whatever it throws at you, I mean, the challenge is for you to ask, to answer it. 7:21 - Yoemy Waller Are you up for a challenge? I'm okay with that too. 7:29 - Donna ChatGPT, here we go. And I'm going to say, hello, ChatGPT. We love a bit of spontaneity. So we thought who better to challenge us than AI? What question would you like to ask a fractional CTO at this exact moment in time? Okay. It's searching, it's searching. It's thinking. Oh, it's really thinking about it. Okay. Okay. You know, Amy, this is your question. What's one sacred best practice in engineering leadership you secretly believe is slowing companies down, but no one dares a challenge because it's politically risky? 8:24 - Yoemy Waller Thinking outside the box. Most people want to stay within the box because this is what we always have done, this is what we need because this is the way we've always done it for whichever amount of time. And if you tell a CEO or you know CIO No, you're not supposed to do that. Think outside the box or you're in the box. You're not seen, you know, farting off. People are scared of that. People are very scared of doing that. In my case, I think I just throw it out. You know, I just think, you know what? You are having too much of a narrow thinking. You've got to expand the opportunities. You know, you cannot be thinking that you're going to go to the future, just looking right here in the middle, right there, because that's what you, is your comfort zone. So I think that's, that's what would be the breakthrough. 9:30 - Donna The breakthrough. 9:31 - Donna And how would you advise people? Cause I can imagine people out there thinking, well, that's all nice for you to say, but how do I, next time I'm in that room, in that board meeting, in that C-level suite, and I something that's outside the box, how should they approach that so that they're not screamed at or thrown out of the room? 9:52 - Yoemy Waller I think, number one, before you ask the question or you say something, you have to be in good terms with yourself. Whatever happened is OK. Whether they accept your out-of-the-box idea whether they don't, it's okay. So ask it anyway. You might, you know, start, for example, saying, this is outside of the box, but my suggestion is A, B, or C. If it brings in an overall, how are you going to say that? Well, let me explain. And then you try to explain each one of the things. If they say, We have always done it this way. And I say, it's okay. That means you will continue to have the same results because you are tapped in this level, right? The boss is not letting you grow. The boss is not letting you solve the problems. The boss is not letting you see the future. So you start by making them understand, oh, maybe I should open my eyes to bigger things, better things, you know, especially with when I'm this unknown that, you know, it might be not politically correct, right, to say it, but, you know, sometimes, and I have said it in a conference actually in front of 500 say, AI is like teenager sex. Everybody says they're doing it, but they're really not. You know? And then with that, the eyes and people say like, oh wow, yeah, she's right. Everybody's bragging about it. Everybody's saying they're doing it. Everybody's saying I got the greatest and the bestest thing. But they're really not. 11:44 - Donna They're really not. 11:45 - Yoemy Waller Go back and analyze where are you with your data? Where are you with your infrastructure? Where are you with your computing capability? All these things are not aligned. So you're not doing AI. You believe you are because you don't know the insights of it. That's a big revelation, you know, for CIOs and CEOs. And yeah, you right there said it, you know, people get shocked when you say like, out of the box like that. And of course, you know, it is super, you know, to me, to be able to introduce, you know, crazy things like AI. It's like that. I give that little story about, you know, teenage sex and everybody goes, they're shocked. What did you just say? Totally politically incorrect. 12:32 - Donna And everybody went like, Oh, you've got their attention. You've got their attention. 12:38 - Yoemy Waller And it makes sense about their own teenage time, you know? And they say, Yeah, I was bragging that I did a bad and whatever. And it was not doing anything. You know, so there you go. So I think is is to be brave. Yeah. 12:53 - Donna Yeah, I like that preemptive saying it because then it kind of softens the blow. Listen, this is going to sound completely off the wall or this is completely out of the box. And then people kind of brace themselves for it. And then whatever you say, it's never going to be as hard hitting than if you just came straight out with it. So yeah, set that scene. I like that. That's great advice. And then yeah, just be brave, follow through, have the information ready to go. But yeah, get rid of this best practice of thinking Inside the box. Love it. 13:27 - Yoemy Waller Yeah, especially for innovation and technology, you got to be able to, you know, to go that, that, that further, you know, there's there are companies that are too attached to their legacy systems. Oh, we develop ourselves this system. And you know, we got it for 10 years. And we have made a lot of money with that. Yeah, that was the end. 13:49 - Donna Yeah. 13:50 - Yoemy Waller You want to grow in the future, you want to do that's another box from completely, you're all positive, it's all, that's it. 13:58 - Donna Yeah, I think we might need to change you from AI evangelist to change evangelist, just bravery. 14:05 - Yoemy Waller It's Part of it, it's Part of it, you know. Some people also, you know, when I'm speaking, they also call me the data czar, right? Yes. So being the data czar, what does the czar does? Dictates. This and that and the other. And I say, you become the data center until you are able to really believe that you're doing the correct thing. It's not that I am doing the correct thing, that you and your company are doing the correct thing. Because if I'm evangelizing something, and let's say, you know, whichever idea, and I'm telling you this is the way or what not, no, it's got to be a consensus. It got to be that they believe, yes, I think that we need to go that way. And then, then I become their data star. Then they say, Oh, yes, we know that you know it. Yes. 14:59 - Donna And then they then they change anything that you tell them to change, right? 15:03 - Yoemy Waller Because it proves the point, right? It proves the point. And you have to be able to to maneuver all of that, you know, and the most important thing and I and I believe is that each of one each CTOs have to know their value. Sometimes people have worked for an employer all their lives, and they don't know. For them, it's like an adventure because, yeah, I might want to have some more money or I might want to expand myself. But that means that they also have to expand their own personal self. Yes. 15:47 - Yoemy Waller and have their own value and understand, you know what, I'm worth this amount of money. 15:52 - Yoemy Waller I am. 15:54 - Yoemy Waller If they don't believe that, they're going to be giving away their work. 15:59 - Yoemy Waller They're going to be charging pennies, you know, and they're going to be taking advantage of having to work too much stuff for very little money. 16:08 - Yoemy Waller That's not how this works. 16:10 - Donna You know, that's not the CTOx way. 16:12 - Yoemy Waller It's not how you should work, you know, and And change of mentality is super important for the fellow members, I think. 16:23 - Yoemy Waller Understanding that, you know what? 16:24 - Yoemy Waller If I want to make it to the next level, I have to grow to the next level. 16:29 - Donna Yes. 16:30 - Donna Yes. 16:31 - Donna And be brave. 16:32 - Donna I love that. 16:32 - Donna Thank you so much. 16:34 - Donna I could talk to you all day long, but I know that you're so busy. 16:37 - Donna But thank you so much. 16:39 - Donna Thank you for sharing. 16:41 - Donna Thank you for all of your knowledge and insights. 16:44 - Donna and wonderful advice to anybody listening here. 16:47 - Donna So thank you very much. 16:50 - Yoemy Waller Thanks. 16:50 - Yoemy Waller Bye bye. 16:51 - Donna Stories, experiences, and advice you hear today are incredibly valuable, not just for CTOs, but for the broader tech community and leaders. 16:59 - Donna To our listeners, thanks for tuning in to Inside CTOx. 17:03 - Donna Don't forget to follow us on social media, tag us, and share your favorite insights from the episode. 17:08 - Donna We love hearing your feedback. 17:10 - Donna Make sure to subscribe and check in again for next episode where we'll continue to explore the stories behind the tech leaders shaping the future. 17:18 - Donna Until next time.