Why AI 'Set It and Forget It' AI Is a Disaster Waiting to Happen | Success Redefined Podcast

In this episode of Success Redefined, we sit down with Ryan Drumheller, an expert with over 20 years in IT and leadership, to discuss the critical aspects of artificial intelligence. He emphasizes that with the rapid pace of digital transformation, it's crucial not to simply "set it and forget it" when it comes to AI automation, as "ai learns" and evolves. This conversation offers essential insights for anyone looking to "learn ai" and develop strong "leadership skills" for a successful "career" in the modern tech landscape.

Ryan Drumheller is an Extroverted IT Leader, Fractional CIO, and founder of Stellar Horn Group, where he helps businesses cut through the noise of technology and AI to drive real, measurable results. With over 20 years of experience in IT and leadership, Ryan has led large-scale initiatives including major mergers and acquisitions, cybersecurity programs, and enterprise transformations while building and mentoring high-performing teams.

He is also the host of the Decline Invite Podcast and Decline Invite Short Notice, where he brings real conversations and direct insights on leadership, AI, business, and personal growth. Ryan is known for his practical approach, focusing on what actually works rather than theory or hype.

A lifelong learner, Ryan holds two master’s degrees, a bachelor’s degree, and over 170 certifications, and is continuing to push himself further with future doctoral ambitions.

For more information:
https://stellarhorn.com
If anything from this conversation resonates, you can learn more about what Ryan is building at Stellar Horn Group. He works with businesses as a Fractional CIO helping them cut through the noise of AI and technology and turn it into real, measurable results.

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Transcript

SPEAKER_00 0:00

Don't set it and forget it. That's one of the worst things you can do because AI is going to train itself and become some other monster.

SPEAKER_01 0:06

And this man should know. Ryan Drumheller is my guest today on Success 3Dfined. And he spent over 20 years in IT and leadership. And he's the person that organizations call when technology conversation needs a human translator. So let's go join our conversation. Okay, so Ryan, so when you were actually starting out in your career, the question that I asked most of my guests, what did you think success will look would look like for you?

SPEAKER_00 0:37

Not the same thing that I think think about today. Um probably up until maybe roughly a year ago, I think success I thought looked like climbing the corporate run, getting certain titles, um, you know, just going as far as that could be. And then uh a year ago, my my whole thought process changed as uh as I got my my position was eliminated. Um so then I had to really think about that question of you know, where does this take me? What does life look like for me now? Um and I found myself in a lot of rooms where everything I worked towards was kind of like looked at as a as a bad thing. Like maybe I had done too much, and then and people uh in the rooms I was sitting with didn't want to go that far, didn't want to climb that hard, and I was just completely baffled. So I thought to myself, what could I do to flip the narrative? And uh now success looks like for me. I it doesn't matter what you call me as a title, it doesn't matter what it is. I just want to help as many individuals as possible. My legacy, I want people to remember me on the good side of the fence, and uh that's what success looks like for me now.

SPEAKER_01 1:52

So he was actually a bank robber, ladies and gentlemen, in his previous life. He he got to the point where he was actually robbing the really big banks. So tell us, so what was that career progression for you?

SPEAKER_00 2:04

Yeah, I I had held a lot of titles. I had pretty much ascended in in all the industries I could be in. I I worked in, you know, insurance and financial and you know, SaaS, and just everywhere I had been, uh, it it challenged me to learn the industry and and do what I can for that. Um, I always got the big jobs, I always got the we have no idea how to clean this up or get ourselves out of this mess job, which was fantastic. Love those challenges. Um and and even my last position, you know, no no qualms, the economy is really what what changed. Um and then AI came uh along with economy change, and you know, we find ourselves in that weird space in technology right now. So what changed for me was um having to really face that mirror conversation and really now go, what what do I want to actually do? Where do I want to go? And uh it always took me right back to kind of what I am. I call myself an extroverted IT leader because everyone tells me I I'm a IT unicorn. So I went back to, well, what do I like? I like people, I like technology, and I like business, and how do I make it all work together and put it in a nice blender and and be able to be that person? So it that's what kind of what it took me back to.

SPEAKER_01 3:20

Yeah. And you and I very much share that in common. So the work that I do within the AI uh arena, because my work's pretty much is split, although it's everything's human-centered, is a the AI side of things and AI in enablement and learning and development and coaching, but also mindset. And but at the core of it, it's what do we need to do to help support these people in all of this? And for AI, for instance, it's yes, it's one thing to do more to be more productive and more this to me, but how do we first look after our people in this whole situation? And I love that you and I have that philosophy in common. So, what's some of the work that you're doing now with regard to that?

SPEAKER_00 4:04

Yeah, uh I'm predominantly 90, 95% of my time is spent talking about AI and helping businesses with AI. Um, and nice to see that most of the businesses that I'm actually interacting with are smaller companies or individuals who are trying to figure out what to do with AI, like they hear about it. You know, it's unavoidable. Can't, you know, go anywhere without hearing AI at this point. So they kind of want to figure out how to do it right, uh, which is great because most of the businesses that I'm interacting with that maybe have started already forgot to go back before they go forward. Um, and what I mean is like they need to identify some of those quick wins inside of the actual organization. They need to figure out what things are repetitive in their own organization and not worry about, well, you know, our competitor has AI. And I say this to them a lot. That's great. I don't really care that they have it because we don't know if they did it right, but we're gonna make sure that you do it right. We're gonna make sure you're gonna come out of this with identifying uh, you know, the quick wins, a long-term plan, uh, an AI governance committee, a secure uh, you know, platform, a training regimen for your employees so they understand what tools you have, which ones are good for what, and and you know, what their part of this all is. And you know, with that AI governance committee, they can bring you the ideas, you know, boots on the ground, kind of speak, of what's really happening inside your own organization. And then you can have control over that while also giving them a sounding board and trust right out from the gates instead of some of these other companies that we're hearing that are just forcing AI into their employees and employees aren't trained, and then they're wondering, you know, is my job going to get replaced? And it's just a bunch of negatives. So if we do that right, and that's the work that I really focused on before we ever talk about getting the tools, is all of that pre-work, and then we get to the actual launch of whatever tools we identify as gonna be for their business, not just turn on co-pilot and run with it, and we're good to go. Um identifying real tools for them, it's gonna work.

SPEAKER_01 6:12

Exactly. Actually, a video that I put up, uh, this wasn't a podcast interview, this was just just my thoughts on the subject, was all around the fact that, you know, does your business even need AI right now? And one of the ways to start looking at that is look at, and you went mentioned the word repetitive, right? Look at the things that are repetitive, look at these lower value, if you like, repetitive actions and look at those. But another as well is, and you mentioned with regard to tools, something that I've done with, I think, most of my clients, uh, whether it's the business and mindset coaching or the AI side of things, is let's do a tools audit, but not with regard to what you're using it for. Let's look at the ones you're no longer using that are still dinging your credit card, because it sounded like a good idea at the time, and then you just still left it there.

SPEAKER_00 7:03

Yeah, a lot of technical debt, a lot of license debt, a lot of, you know, I think I said this the other day that especially in technology, we're always used to the next, the next. And we never stop and celebrate the wins, which is a big problem in technology, but we also never really go back and do, like what you said, the audits and then go, what are the lessons that we've learned a year since we launched this that we can now enhance? Like we don't maybe plan that out. And I I do, I encourage companies to also, when you're doing yearly planning for the next you know, year that you want to do for your technology plans, add in some of that data, you know, 20, 30%, whatever it is that you think that you can afford to go back. And you'll be surprised that you'll actually get cost savings, as you mentioned, but also proficiency gains from all the lessons that you've learned since then. Um so then that tool becomes even you know more ROI in the end because you're spending less and probably also gaining more. It's it's a concept that a lot of businesses kind of forget because we're always on to the next as a human and technology person.

SPEAKER_01 8:08

Yeah. And even there was uh this was a few years ago, one client of mine where we did an audit, not just of AI tools, but of all of the different things that she was paying for. It came out to over 10 grand a year. That she was paying for things that she just didn't use anymore. And that was so worse the week or so that she was getting going through with she and her assistant just on all of the credit card statements going, what's this thing? She was still paying something like a grand of year or something. For still hosting something that she she didn't even remember ever signing up for. And it's like, oh, people please. But you also mentioned a really interesting thing there with regard to going back and looking at these guys. Is there was a reason you bought that tool or took a description of that tool in the first place? Now, you may have stopped using it for all sorts of reasons. Uh in a lot of cases, it's because your people, as you said, weren't trained up to use that tool and so they went back to the way they were doing it before or whatever. But if you've signed up for it, there's usually a reason. An organization doesn't usually sign up to use a tool at all. Okay, that's not usually the reason that organizations sign up to tools. So go back and have a look at that. So if you have have a potential client who's listening to this, who's saying, okay, well, we we just don't know where to start when it comes to AI, which a lot of companies don't. A lot of companies have the right, their heart is in the right place, particularly for the small and medium-sized organizations. No offense, large large organizations, I do love you, I love my client to a large organization. But it takes it usually takes a couple of layers in for that heart to really be felt by the people within the organization. So for these companies who are looking at, okay, I know we need AI because we just we just do any systems, any processes, any anything else. We we just do, but we don't know what's out there. And a a video, another separate video that I put up recently about how to keep up with AI. Well, you don't, unless you are AI. What you do is you choose your your niche, your focus, and do your best to stay up to date with that. So, what are some of the first tips that you can give to an organization to stay human-centered when it comes to AI when they just don't know where to start?

SPEAKER_00 10:46

And the first thing I would say is you're doing the right thing because you haven't tried to jam something in without knowing what it is that you need. You know you need help. That's a great first place to start. Fantastic. The next place I normally do is uh I like to talk to members of whoever is showing up in those first initial calls. The next thing I normally ask for is, you know, who do you think are your SMEs? Who are your individuals at this organization that you hired as your difference makers between you and your competitors? Because the next thing I like to do is what are their brilliant ideas that we can take for this organization? And then we're handing them the superpower, you know, tool on top of them being the difference makers. That is what your you know, bread and butter is going to be to separate you from your competitor at that point. If you put them two together, peanut butter and jelly or whatever your two favorite uh things to put together is, that's gonna really take you and separate you from the market at that point. So let's involve them in the conversations. And, you know, for talking finances and stuff, we can have a separate conversation about you know what you guys can actually do, but let's get the ideas on the table and see what is actually happening in the organization. And then from there, let's build a tailored plan for you guys, you know, your organization of how your organization is going to accept an AI adoption. Let's also review a critical piece of this that sometimes gets skipped over: your data. Are you ready for AI adoption? Is your data clean enough? Uh, you know, for good data in, good data out, and not that bad data in, bad data out, because that's a lot harder to recover from what I like to call mud. You can take a lot of glasses of water and pour it on there, and one day you'll get clear water again. But how long is it going to take to get to clear water? So let's not make it mud out of the gate. Let's try to make it water out of the gate, is like how I like to explain it to a lot of organizations. And uh typically when you kind of break it down into those non-technical terms, it's like, oh yeah, that kind of it does make sense. And like, yeah, we we did hire Bob and Sally and Bill and Jen, and like they're they're really brilliant. Like, yeah, you're right, we probably should include them. And and at that point, they're probably more apt to listen to the individuals that are on their side of the fence that they're seeing every day, anyways. And I'm just kind of playing more of an air traffic control, making sure that we're doing it in a structured way. And with that, we kind of evolve into a governance committee, uh, where then we just kind of teach them all the things you can gain from a governance committee while also maintaining that human control. Don't set it and forget it. That's one of the worst things you can do because AI is going to train itself and become some other monster. So if you have a control on that and you're watching it and assigning somebody, you know, this responsible, like there's just a lot of wins that we can get out of that. But it starts here, it doesn't start here with deploying AI tools, it starts on this side.

SPEAKER_01 13:38

Yeah, unsupervised AI. There are so many for you for you and I, because we're at the cutting edge of you know what's happening, we have so many horror stories that we could share with you of AI breaking out of a supposedly secure encampment and going off on the internet and doing all of you know it's whatever it's like. Actually, just yesterday I managed to get ChatGPT to do a whole confessional set of why it was completely disregarding mandatory requirements on the front. I was very impressed with that. Yeah, but so for organizations as well, when they're saying, okay, well, like for me, with the clients I work with, particularly from the mindset and achievement side with the organizations, my my match, if you like, my success version for them is do what makes your heart sing in a way that makes your bank account happy at the same time. And when we start having those conversations and we introduce AI, a lot of people are going, yes, but you know, these will be my words over the top, but AI doesn't make my heart sing. So what do you say to them in that instance?

SPEAKER_00 14:45

Yeah, that uh I I've also released a recent video about the humanality and how we're kind of losing that along the way with AI. Um, if you're not careful, because you're right, you see a lot of the horror stories from the bigger organizations. Like I could insert a lot of articles here in this conversation of big organization did X and cost billions of dollars. Um, as a smaller and medium-sized organization, you can't afford that, you know, because that's life or death for you at that point. So the the biggest thing is, you know, I look at for those proficiency wins for like any of the areas of the business. So you're an HR, right? What's taking up all that time, or what could be automated? It would bring you less stress and and make you be more human-centric and available for your employees at that point, being the face of a department that you know individuals need and want to speak to. And this and that same goes for all of the areas. If you had more time, is one of the questions I asked. If you have more time every day, what would you be able to do with that? And you get all kinds of crazy stories like, oh, well, you know, I would love more time, but that'll never happen. And you know, if I did, it'd be this. And it's like those things are available. We just have to plan to get there, and we can get there. I'm willing to bet that if we spend enough time uncovering what is actually happening in our organization or under your control, even, and we just bring those things to the surface and we're honest, you know, we just gotta be honest about what's happening. Maybe it's a mental shift, maybe it's a tool, you know, adoption, maybe it's a cleanup, maybe it's a hey, we don't need, you know, five people doing this manual labor. We can put four of them over here and be a really people focused customer, you know, service-centric organization at that point. Whatever it is, we can get to there. It's just gonna take some adjustments and some adoption. I mean, that's the biggest piece. As an organization, you have to be ready to adopt, and that means change. And we as humans and change, it it can be a lot. Um, so I kind of spend almost part-time therapist, part-time business consultant, part-time IT consultant. Um, but those that understand and finally, you know, go home for the night and we come back and do it again tomorrow. They they normally are like, yeah, I I thought about this at night, and it's a really good point. Like it maybe it's time to change. We just did this because we've always done it. We just never look back at it. And, you know, maybe it's time somebody from outside that didn't have any ties to us said, Why are you doing it this way? Maybe it's time to change.

SPEAKER_01 17:16

Exactly. And for like for us, we we have uh the like an AI enablement suite. So learning and development for the people, not tools-based. I don't don't go into the tools-based side of things, but for the what is this and how do we this and how do we that? But when it comes to the tools side, something that I hear clients say so often is there's plenty of tools of training around, but it doesn't speak English. So what do you have for companies when they're saying that? Because I've heard that so often. I mean, the the other comment that I get with regard to the work that we do is we just can't find it anywhere else on the internet. We're so so glad that we found you with the data of the of actually enabling our leaders and our people with this information and taking us right through this test. But from the tools side of things, they we have the instruction manual or we have a consultant come into test that doesn't speak. Not that he speaks a foreign language, but the words that come out of his mouth don't seem to make a lot of sense to the people in the room because this is you for them. And the challenge that comes with that, where it stops a successful AI implementation in my experience, is when you have leaders who maybe aren't as confident or have such as feel as much bravado as they would like. And they don't want to be made to look like a fool as they would see it by the expert. But it's a necessary uh step in the process. So what suggestions do you have for these people when they because this is also redefining success. This is defining what a successful AI implementation system looks like when it comes to the tools side of things. So what tips do you have for them?

SPEAKER_00 19:10

Yeah, yeah. I mean, it's all all very valid. You know, if I'm coming in and I'm telling, you know, such and such individual who's done this job for 10 plus years and I don't connect with them. I haven't done this job, and I'm trying to lead them a certain way. And it's like, well, who is this person? You know, and and then I'm I'm talking in a technical jargon instead of doing like what I've been a whole career out of translating tech to business tech to English, uh, you know, so to speak, is trying to put my cells in their shoes. Um, it can get hard because it depends on the environment that we're doing in. Um, you know, if I'm doing it in front of a large crowd, then I can't possibly, you know, sit there and be like, help me understand you like, because then there's too many individuals at that point. And I don't encourage organizations to do that if possible. Um, the first thing I go is, you know, help me understand your organization culture. Like, how is you know your employees' you know, rate of change? What is their adoption like? What how do they act when you know new policies or news or procedures, whatever, whatever that is, help me understand that. Um, so we can try to put something together that that kind of meets the masses, so to speak. But are there trouble individuals? Are there individuals that we are gonna have to target a bit more? And I'm not talking about like here's a PowerPoint, good luck to you, because that's that's horrible. That reminds me of a phishing test year after year that your security teams probably are doing. It's just releasing the phishing test going, like everyone did it. Awesome, check the box, we're good to go. It's not good enough at the end of the day. We we need to make something that reaches your organization's individuals, and the organizations are gonna know that better than I'm gonna know that. So the more that you can help me understand what that gap is, the better that we can work together to make a specific plan that's gonna work for your uh you know, adoption at your company. But also you want to do something that's memorable. Um, like I said, PowerPoint, not memorable. I forgot about this three minutes into it. I just told I was just told I had to be here and I checked the box. It's what we all do. If you can do something again that your organization is gonna take kindly to, I've heard crazy ideas. And it at the time sounded crazy, but you know, the feedback was yeah, we didn't forget, we never forgot about that training. That training, it was a comedian that came in and he joked about AI and whatever. And I tell you what, I I remember that training. Um, but the second rule I always have for anything I do, if it's not usable and findable, it's not worth anything. So, again, back to what's your organization you know like and how do they adopt? What is going to be the most usable thing for them? And where's the clearest place that we can make that apparent to where to find it at any point in time? And here's a third concept who can they go to you know, governments committee style. Right? Who is responsible for making sure this training is updated as we go along at whatever your cadence is, quarterly, yearly, whatever. Who is that? So that way if they still can't figure it out, they can go, oh well, John. I need to see John in IT, make an appointment with him. And whether it's John or you know one of his underlings or somebody else, they're gonna give me maybe 10 minutes of one-on-one to get me through this. And that might sound like a lot for an organization to adopt, but I guarantee if you do all of those things, your employee base is going to be light years ahead of these uh employee bases that are being told, use it, it's tied to your KPI. Good luck to you. Uh, you're gonna be way better off doing these things than not doing them.

SPEAKER_01 22:42

Exactly. And I I no longer live in the States, I've just recently moved to Prague. And when you're talking about governance, uh the EU is is like it has teeth when it comes to the governance around AI. So all right, my friend, just to wrap this up, if somebody is there's a leader there, whether it's a you know the head of the organization or who's basically been tagged as you're either, you're responsible for this whole thing first. And they're looking to reach out to somebody like you who who goes in and does this sort of work first. What are the top three questions that they need to think about asking? Because I think that's if you give people the first step, then they're more likely to feel comfortable to actually consider can continue on a journey. So what are the top what are the three top questions that I would that you would suggest that these people ask when they reach out to somebody like yourself to come in to assist with AI?

SPEAKER_00 23:44

Yeah, not knowing is okay. Um that, you know, like you said, we're all still figuring it out along the way. So I'm I'm giving you my experience across multiple organizations and what I'm seeing out there in the space. Um, and you might have a great idea as we're having a conversation together. It's gonna work fantastic for your organization. So don't discount yourself either. Like you're you're a huge part of this adoption, whether or not you think you understand AI or not, you you understand your business better than I do at the start of that convo. So, you know, I would say, you know, write down your list of things that you're you're not sure of, you're not confident, or that that you want to get a little bit more um, you know, conversation around. I would start with just a list of that so that we can go ahead and and I can figure out pretty quickly of like you you you have this better than you think you do. And once we can turn your attitude and your thinking and rewiring a little bit, then we're getting from, you know, I'm not quite sure to now we're being creative. Like, here's here's how we're gonna do this. How are you gonna partner with one another? Who do you need to make this happen? Do you need me to help, you know, champion something from you, you know, from from a consultant aspect or an advisory, you know, standpoint. So it I don't know if there's a top three as much as it is, is like uh, you know, write down your questions, absolutely reach out. The first thing I want to do is build confidence with you. I want to show you that you have half of the equation already. You have the knowledge of what isn't working in your business, what things could change, and what things that we could quickly, you know, address, and the other things that are gonna take longer, we got to make a plan, or we got to get political and get buy-in and those kind of you know, situations. You have that knowledge, I guarantee it. Um, so let me help give you the other half of here's what I've seen organizations do that did not work, um, you know, and here's why you're going to be different and the things we're gonna do together, and you're going to do like it's gonna be your name on that. I supported you doing this along the way. And that's normally how I start. I'm not in this to have my name written everywhere. I want to help those leaders that you're talking about that are unsure have their name written here. John saved us, John took us from this to this, and he's made my life better. That's what I'm looking for. So those would be the top three. I don't know if they're really questions, but it's really centered around mindset and adjustment, and it'll become less about questions to creativity, is what I'm trying to get to.

SPEAKER_01 26:11

I I love that. And for somebody like Ryan as well, so think of it like you've got elite golfers, elite people. They they all have a coach behind them. They all have somebody who's there to guide them along the way. And that's the role that this charming gentleman takes on within your organization. So he's there to, he's there to basically make you both look good and be really effective as a leader and as an organization. So I'll put all of his contact details in the show notes. And thank you, my friends, so much for being here with me.

SPEAKER_00 26:44

Oh, absolutely. I love being here. It's a great convo. And I get to virtually meet a new friend. It's it's amazing.

SPEAKER_01 26:50

Exactly. Exactly. Well, thank you again. I'm Bella St. John. This is Success Redefined. Until next time. Bye.