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Overcoming Resistance to IT Modernization Initiatives

NinjaOne
06/15/2026
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All right, I think we're recording. Welcome in, everyone. We are here with another IT Leadership Lab live stream. I think this one is going to be a really interesting topic to discuss. But if you are new to the IT Leadership Lab, if this is your first event, welcome in. The IT Leadership Lab is a community dedicated to IT leaders. It's a place for you to share content, learn from your peers, build community, things like that. And then in that vein, we also host bimonthly webinars to discuss various IT leadership topics. We bring on leaders within the space that can actually share their expertise. Because I've never been an IT leader, but all of these people have. And they have some really great feedback on a variety of different IT leadership topics. So, today we are talking about driving modernization. So, as an IT leader, you're kind of in charge of basically everything that plugs in, or at least to those around the organization. It also means that you are the one that notices when things are running too slow and need improvement. But a lot of the time, that is not the shiny new thing. That is not an AI platform. It's just back end improvements that kind of help the organization run. And a lot of executives can be distracted by shiny new things. So, today we're going to talk about how you can drive modernization when it can be anything but a shiny new toy. So, I'm going to go ahead and pass it off to my speakers to introduce themselves, talk a little bit about how long they've been in IT, what they're doing now, things like that. So, I'll go ahead and let Jason start. Perfect. Hello, everyone. I'm Jason Granite. I am the Director of Information Systems for Wish Farms, a small agricultural, well, not even small, but agricultural company. We deal with produce. So, I've been in this director role now for almost nine years with Wish. And I've been in industry since, oh, gosh, early 2000s. So, I've been all around. I've done just about everything in the industry. And I definitely enjoy kind of talking. Obviously, you'll find that I enjoy talking. And I like driving innovations. So, definitely excited to be here with the team and talking today. Yeah. It's always great to have you on. I appreciate you joining again. Thanks. Tim, do you want to go next? Yeah, sure. Hi, everyone. Tim Lanning. I'm the Vice President of IT for SGRC Texas, a nonprofit in the San Antonio, Texas area. I started out as the IT manager in September of 2022. And through a series of mostly fortunate events, I'm now the VP of IT going on over two years now. I get to say that for real. It's been a really interesting journey. Basically built the IT department from scratch out here, have an incredible executive team that supports what we're doing. And with that comes some challenges, because like I said, I am a nonprofit. So, when Brittany brought this topic forward, I said, hi, as the resident expert in driving modernization in less than ideal circumstances, I'm happy to be part of this. So, hopefully, my struggles have been, will result in some usefulness for those in a similar boat. But yeah, awesome. Brittany, thank you for having me again. Yeah, thank you. All right, Nate. I'm Nate Payne, and I've been in IT about 30 plus years now. I held pretty much every role from help desk to IT director. I currently run an MSP called Better Business Technology. Though I spend most of my time doing IT leadership consulting. And like Jason, I spend a lot of time talking about IT leadership and writing about IT leadership. The goal is to help IT leaders kind of move from that support role into more of a strategic partner. How do you do that specifically? And so, that's what I spend most of my time doing. I love to jump on these live streams and hear other people's input as well to solve some of these very common problems. And I can tell you after 30 years, this is not a new problem. Okay, so it's not going to go away. And it's a very good topic today. So, thank you, Brittany, for having me. Yeah, thank you. I'm going to drop a couple of links in the chat here in a second. Nate's done some really good presentations, both, you know, just like these live streams, but also in our recent summit, we have a workshop recording and the actual presentation. So, I'm going to drop those in the chat in a second, but wanted to get the conversation going first. So, first things first, I kind of want to set kind of a definition on resistance. What does resistance usually look like whenever you introduce some sort of modernization initiative? Is it an outright no? Is it are they kind of wishy-washy and not wanting to commit to anything? What does resistance look like in those kinds of situations? Yeah, so I'll hop first. So, while we're not a non-profit, like Tim, right, we do come from an industry that is, you know, produce and agriculture, right, is an industry that is, you know, filled with generations of farmers, right? Like, they know how to do what they do, and they've been doing it that way, right? So, there is definitely a resistance, specifically around technology. A lot of times to say, you know, hey, I've been growing on this land for, you know, 30 years. My family's been here for 60, right? Like, I know what I'm going to get out of this. I know, you know, how we're going to make a beautiful looking, you know, piece of fruit that comes out of it, and it's going to grow, and it's going to be tasty. So, for us, a lot of it is this, like, sort of vertical, like, almost like industry kind of resistance to that. You know, obviously, we're no different than any other industry where margins are starting to become tighter and tighter around, you know, profit and, you know, cost of goods is going up. So, for me, it's really just the first part of this, and there's all kinds of different resistance, but for me, it's usually like an industry-related item. You know, there's a lot of that feeling like, hey, we've always done it this way. You know, we kind of would like to keep doing it this way. So, that's sort of where I kick there. There's obviously a whole additional things there, but I'll talk for, like, an hour about it, and I don't want to do that. I'm going to chime in on what Jason just said. It's for context. We are now, my company's now a 700-person organization, officially. Yay, I did it. I'm not a Withered Tusk in the corner like I thought I would be. So, there's that. By the way, this is Andrew, for those who didn't read my message. This is Aragorn's sword reforged from the Lord of the Rings films. Greatest sword ever made. I just have a replica of it. My wife is amazing. Anyway, best birthday gift I could ever receive. Beside the point, okay. It very much is a we've always done it this way. We started as 75 people in this organization when I was brought on board. I think I was employee number 95, if I remember right, and I was the encountering the system as it is. The, hey, the reason they made certain decisions were almost always because they were forced to. They severed from a national entity that gave them, you know, now they have autonomy, and all of a sudden they have to make a bunch of decisions about what technology systems to use because they can't just use what this national entity was using. And so, there's always this like inciting event that happens. And then, the thing that they've always done since like 2016, right, so always, you know, that's like a decade ago. Holy cow. Anyway, it really is just they've always done it this way. Always, since 2016. Always. Okay, great. But systems have improved since then, whether they're hardware, software, anything, anything that you're looking to change, for whatever reason you're looking to change it to, chances are somebody is going to hit you with the, but I really like, okay, great, yes. I want to work with you on that one. So, resistance is not anything necessarily malicious, unless it is, and you know when it is. I think it's just that people are comfortable. Why, if it ain't broke, don't fix it, is the perception. What they don't know is that it's probably massively broke. That's what I'll say there, in my experience. Yeah, good point, Tim. If you guys have heard me before, I always say that people act in their own self-interest. I always start there. When you want to understand resistance or behavior, just start there, and you say, well, what does that mean? Well, what it means is there's something about what you're proposing, the modernization, the person is always going to say, how does this affect me? That's really what they're saying, and if they have a perception that these changes are going to negatively impact them or bring about a certain amount of discomfort, then they're going to be resistant to it. So, even though they're saying we've always done it this way, here's what they're really saying. What they're really saying is, I'm concerned because there's something about the way we've been doing it that is predictable for me, that feels solid, that I really have a grasp on, and I feel I'm going to lose that if we make those changes. So, I mean, it's resistance, but not against you or your idea. It's really, I don't want to lose something, and that's the position a lot of us, as human beings, we sort of make our decisions, right? It's a fear of losing something, whether that's control or autonomy or whatever it is. So, I think just kind of keeping that in mind as you frame your approach is very helpful to kind of reassure them that the things that they care most about will still be there in place, and that they can actually help you shape the direction of the evolution of the technology in the organisation. Yeah, that is a great point, and kind of goes into my next question, which was about the most common excuses or the most common responses you get when it comes to resistance, or the reasons why people don't want to make those modernisation efforts. I know that, obviously, a lot of people get comfortable in what they have, but I know that there is also an aspect of money, and so that's another thing that people are resistant to, they're resistant to spend money. What are some of those common reasons that you see people resist modernisation, and what is kind of the most frustrating to deal with? Go ahead, Tim. We just played the mute game. So, it depends, right? It really does, because who is the non-technical leader? And kind of what we elaborated on in the resistance bit just a second ago, that is it, right? Finance, I have found, is obviously very interested in why am I spending money? The specific quote is, why am I lighting money on fire for you? That is verbatim what I have heard at times, and it's a good question, right? I know why they're asking it. They want to make sure that it's a real reason. It's not just because you want to. There's a valid reason, and they need to know it. So, that's been the biggest thing for me. I work directly for the CFO, so I get that a lot, and there's benefits and drawbacks to reporting to any executive in the organisation, but then you've got, I think, we're weird because we have programmatic staff that are caseworkers, right? So, a lot of that is, so many of them came from a state agency. How they've done it, that's the way they expect it to be done here at the non-profit that does not have the same constraints or the same limitless budget where they can just go to the legislature and say, money, please. We don't get that. So, you know, and that's the comforting thing there is it's not just IT that's feeling the resistance to, honestly, in a way, I'm going to extrapolate just for a brief second. The entire organisation is hitting all of these caseworkers with modernisation because they've been doing things the state way for years, decades, and all of a sudden we're asking them to come in and be part of a nimble non-profit with different mileage constraints. All these things, it's reassuring to me that I'm not the only one that's facing resistance, but okay, I've dissembled long enough, right? Like, finance, why spend the money is, I think, a large one, and I don't really want to take anybody else's answer, so I'll just stop there. I think that's the big one that I run into a lot. So for me, I think that to play a little bit off of Nate's answer for the last one is, I think that especially in this time, right, as we're talking about generative AI and all I think that especially in this these new tools, right, and there's a lot of talk about all these things that are going to make us obsolete, or these platforms that are going to turn us into just something else to not have to be able to have my job, right? I think there's definitely a feeling of that modernization, where it gets lost sometimes in the, well, we're modernizing to reduce headcount, right? Where they say, I'm bringing in new systems, they're going to be more efficient. And the workforce immediately says, well, what does that mean for me? Right? You know, what does that mean when I now can do my job and, you know, in 25% less time or what have you, right? So I think that it's really important for businesses to be able to communicate and align with their own staff to say, yes, we know that these things are going to bring efficiencies, right, to do that. It doesn't mean that I'm looking to reduce headcount. I'm looking to move you into other things you want to do, or to be able to find new avenues of revenue streams or whatever that looks like, right, for your business. But I think that just modernization in general, I think especially right now, I'm picking on the AI bubble, right? I think that there's a lot of that discomfort from the workforce that says, well, modernization is going to make me obsolete, right? So and I think that it's easy to pick on that bubble right now, but I think that you've had that over the years anyways, right? If it wasn't AI, it was, you know, the machine learning or it was big data or self service BI or it was virtualization, right? So it's just all of these things that as our industry moves forward from an IT perspective, that those taking advantage of that technology and that modernization has to be communicated that it's there to make your job better, right, and to make the job easier or more effective for you, not to make you an obsolete piece of the puzzle. So for me, I think it's just employees being concerned about job security, right, I think is a big component there. Yes. Also, to Tim's point, so Tim, like you, I reported to the CFO a number of times, and it's a blessing and a curse, OK? So it really teaches you how to look at the business as a whole and not just IT. And of course, you know what the curse part is, because everything has to be justified. But the point around the cost I want to make is this, you have to remember, within IT, we're making decisions as leaders, and we're prioritizing, right, because we don't have an unlimited budget. But the organization as a whole, every department is also presenting a budget of things that they feel are high priority for them. And so the executive staff, the CFO, whoever, they have to weigh those things because they're all high priority to the leaders of those particular business units. So that's one. The reason that that matters is because within the context of IT, even though there's a justifiable reason and you can make the case it's not enough, because you're not up against other IT projects, you're up against other organizational projects. And so you have to frame your recommendation, this modernization project, quantifiably. What does it mean to the business? In numbers, we're going to go from being able to punch out 50 widgets to 500 widgets. Which means X. And we have to speak more in those terms, because it's being weighed against other high priority projects as well, and they can't choose them all. So sometimes it's not even a cost thing, it's just your cost against another cost, and they're weighing priority, but they're pushing back on cost. So just also something to keep in mind, the competition gets stiffer as you move up the ranks there. If I can chime in here with one of Tim's life lessons that will probably go into my autobiographical memoir in the future, this is directly to that point, though. You can't really know what the other organizational priorities are unless you're directly told, which I doubt you are. If you are, can I come work for you? Because that's not how my business works. Two, you have to go put your nose in everyone's business. If you don't report to the CFO, get in the CFO's business. Not in a way that's like, I need to know what you're doing. I'm saying build rapport with these people. Don't treat them as enemies. If someone's being hostile to you, that's one thing. But don't like, oh, those people over there, I'm not going to talk to them. You are making a grave mistake, my friend. Get in with the people that may be competing for your budget. Understand them. Say, hey, can I see what you're up to? There may be ways. You're not even aware of what these guys are doing over here, but I am. Let's tie all that together. I probably stole something that you were going to say in the process of this, but it's been something that you've taught me is be the glue. You be the one in all of the rooms so that you can serve as that expert on what all the organization's doing. Take that upon yourself. I have implemented that very successfully where everyone, it's like a switch flipped. Everyone's like, oh, Tim, you get to be in this room, in this room, in this room, in this room. And now I know so much more. Whereas baby VP that was untested, kicked out of the nest, they weren't going to do the same thing with him. But when you prove your value, because you prove that you're competent, there you go. So that's what I would say. Get in, build rapport with these people. They are people, too, by the way. I'm sure if you have a conversation with them, they may even end up tolerating you by the end of the conversation. What Tim just described, I just want to jump in here because it's very important. What he just described is that transition from being support to being a strategic partner. It's very subtle because here's what happens, right? We start off, we're in help desk, we're in desktop support. We're working from a position of we're waiting. You come to me, you give me a ticket, I respond. What Tim is describing is something a little bit different. We want to move from being viewed as support to the organization to we're part of what sustains and grows that organization. We cannot do that if we are not aware, as he said, what are the priorities? What's important to us? He's right. Most of the time, the leaders of those other business units are not necessarily going to proactively come to you. Many of them are just unaware of the connection, the relationship between what they want and what you provide. They just don't know to ask. This is why it's important for us to be proactive, to just get on their calendar, to have those relationships, to figure out what's important to them. Now, when you go to present a project, it's a different type of vibe in the room because I'm here to help the organization as a whole, not just respond to tickets. Yeah, it's like y'all were reading my notes. You sent us the script on this one. I don't know if you normally do that. Oh, yeah, I totally forgot. I said the wrong line. I'm sorry. We'll go back. Yeah, that was mine. Yeah, they can't know that. They can't know that. Yeah, that was kind of one of my next questions, and it's mostly been answered, but it was translating technical necessity into business value and how you do that with non-technical people in the organization and those people that have that kind of decision-making power. Yeah, so I think from our perspective, we did really hammer this, right? Obviously, really great points on all of those. You know, I tell my team, as you continue to move forward, it becomes less about me being a break-fix person, right, and more about me with optics and helping to remove roadblocks and then drive strategy, whereas I'm not saying, hey, you know, yeah, your laptop's not working. Let me hop in and start hammering on it, right? I can, but that's not where I am as I move forward. So I think the big thing here, right, is to cultivate those relationships, as both Nate and Tim have talked about going up, but I also think it's an interesting and a good opportunity to cultivate relationships going down the other direction. You know, we have an environment where we've got a production floor, right, and manufacturing on site, so I'll go and I'll walk around manufacturing, right? Like, I'll go and I'll spend, you know, an hour or so kind of just watching the line, right, and seeing what's going on, you know, I'll ask some questions, you know, I'll pull a supervisor off the line and say, hey, what, you know, what do we have, you know, what's going on? I see we're blocked up here, you know, what's happening? And I just sort of, as you say, kind of put my nose, right, I just sort of wander around, right, with it looks like I'm just wandering around, but like I'm purposely looking to say, you know, we've got people that are picking things, we've got forklifts driving around, and we have people in the shipping office that are doing things and receiving side. And I think the key thing that I would make to help, you know, because those individuals are not necessarily technical, right? The individuals that I'm working with going that direction are not those where you say, hey, I'm sitting down and let me talk to you about the benefits of single sign on and why it's very important for you as a user, right? Like, they're not that right audience, but they're an audience that I can at least talk to. And I can say, hey, what's your what's the problems that you're seeing here? Is there a technical solution that we can help with? Is it something that we just, you know, the team doesn't know to ask about? Or is it something that we're just completely unaware of? And people are taking care of it and fixing something and like kind of glossing it over, not knowing that they could ask for help about it, right? So, so I think it's very important to go to go both directions, right to go to go up and also to go down to be visible, right? Because as I'm walking through people, you know, people say, Jason, hey, I'm doing this thing. So perfect. Let's talk about it, right? Because then I can take that and continue to be that that advocate to move that up the chain for them as well, right? So, so I really relationships are just super important. And I think it's to me, the key is I don't just look to go up because obviously it is good to go up. But I definitely am a proponent of going the other direction as well, because I want to be able to talk to everybody, whether, you know, they're an executive, whether they're, you know, a part-time worker that's in the office for us. I want to be able to talk across that. Okay. The mute worked. Okay. That's really weird. All right. Probably me. I should put in the ticket. There's a hidden benefit to what Jason just said as well, which is when you properly get to implement things, right? You know, a hundred percent of the time that we get to properly do everything, right? Of course, that's how that works. That's why we're here. We're just all sharing in the panacea that is, you know, us working amazingly. Panacea, great word. But if you go and you understand both the up and the down, like Jason just said, you get a sense into what these people are going to need because you literally see what they're doing. So let's take documentation for an example. You make a change and you're documenting it and you're giving people documentation. You know that if you have a forklift operator, they are not strictly sitting there at a desk with a keyboard and a mouse able to do X, Y, and Z. So you automatically inform how you're writing these things that, oh, okay. Hey, on your phone, write this and this and this, or they have a very basic account. So your use cases, everything gets informed by the situation on the ground, which is so much simpler for you rather than trying to educationally solve a use case. You can just look at what's happening and solve that. Genius point. That's a great point. Yes, I'd like to chime in on that as well. I think what Jason's saying is incredibly important and almost the other side of the in terms of taking ownership and moving from support to a strategic partner. And here's what I mean by that. The most important thing, you're in business to solve a problem for someone. How do you do that? So a lot of times we forget this as IT leaders, but also just leaders in other business units. We're so focused on our domain of expertise that we forget what we're really there for. We're only really there to support systems that help our organization solve a problem for their customers. And by going and having relationships, as Jason said, up and down, I get a clearer picture of what that looks like. How are we doing that? And it's really only then can I get a sense of what I call ownership as we're not the CEO. We run IT. I get that, but it's really taking that ownership. If this were my company, if this were my organization, I would go out. I would go out and stand at the line for an hour. I would talk to the people who are closest to the work because those are the people that are also helping us solve a problem for our customer. And so the greater sense that I have of how all those parts fit together, guess what? When it's budget time and I'm making recommendations for modernization, I have essentially these use cases that tie in relationally, not just technically. Right, it's going to help the people on the line because here are the workarounds that they're dealing with all the time. How much time are they losing by doing those workarounds and we have a simple fix? But you know what? If we do this simple fix, it also helps HR because they're having this problem, right? And they're doing this workaround. So you miss all of that if you don't go out and build those relationships. Anyway, I think the point has been made. Oh, that's, that is great. Yeah, I think that Bernard said in chat, I really enjoy your content and could listen to all of you all day. And I second that. Also feel like y'all have a lot of really great feedback. So I just wanted to make sure that y'all saw that. Okay, so whenever you are in the process of advocating, you can talk about the positives of acting on this modernization. Do you ever focus on the negatives of inaction? If you were to not do X, Y, and Z, what negative impacts would that have? And it looks like Tim, you have a very specific example potentially. Yes, what do you, how do you know? I like, okay, we have a campus that is 40 years old. They are the reason we exist. They are what we were doing before we took on all these state contracts and the focus of the business kind of shifted. They are still our flagship campus. We love those folks. It's out in Bolverde, Texas. Awesome drive, awesome vibes out there. But from a fiscal perspective, they are not operating at anywhere resembling a profit. So not knowing this, in comes plucky VP of IT. Hey, everything at this campus is super old. All the network equipment, everything. We should do a complete refresh because yes, not even any other reason than just it's really old, 10 years old. They bought it all when they had to split. Anyway, they used some of the buyout to do that. It was great. Anyway, this stuff is super old. Okay, so I go in and I say, hey, here's how it'll cost you $120,000. Not bad, I have great vendors, amazing. I get told, no, not until they turn a profit. I say, okay, I hear you. I do, I really do. Just so you know, this is what this means. Like reflex, like, and here's the thing, here's the tip that is kind of embedded in this. I like showing my hand, I'm horrible at poker. I immediately had that information ready because even though I didn't know it, I prepared for that eventuality. That somebody was gonna have resistance. Some gotcha that I didn't know about. The only way you win in that situation, at least at all, even if you don't get what you want, which I still haven't gotten, by the way, that's fine. It's been a while. The reason I won in the end is because I prepared for that. And I said, look, here's the cost of inaction, right? If you don't do this, the network's gonna get worse out there. If you wanna have big events out there, we're not gonna be able to do it because you won't even let us put in the right equipment that we need. You keep tacking buildings on and that's not great. That means that, yeah, I'm buying new infrastructure, but like, it's just for this one building. The switch back end and everything is horrible. By the way, it's a 200 megabit connection to the entire site. So you can see there's a lot, like that's not dedicated fiber, by the way, lest you think that's good. I'm trying to fight these fights. Point is, how do you quantify the cost of inaction is one thing. You have to be prepared for it. So do your research ahead of time. Don't say, oh, I don't know, because then you've lost. Even if you don't get what you want, I guess that's the thing that's undercurrent all here. Like it honestly, if the organization truly takes what you're saying and decides, no, we're not gonna do that. That's because they survived the gauntlet of you being a persistent burr in the saddle the entire time saying, here's what's exactly going to happen if you don't do this thing. And I've done that. And if they still roll the dice, like, okay, this isn't anything that's like organizationally, like I'm liable for anything. It's just that their network's gonna suck. And then I'm gonna get a lot of tickets as a result, but they're all okay with that. So that's fine. The risk, I'm not gonna die on the hill is what I'm saying, because ultimately at the end of the day, it's not a big deal. So please do your research into what exactly the ramifications of your actions are before you make a recommendation. That was a baby IT manager thing I did in a separate incident and I got thwacked for it. And now I will never do anything without researching exactly what'll go wrong. So I'm gonna play the devil's advocate here for a second. You can blame my old CFO for this. So here's how I'm gonna look at it. I'm gonna say, well, okay, I have a bill over here for 120K and then I have a maintenance increased tickets. Is that more than 120K? And if the answer is no, the CFO doesn't care that you guys get more tickets unless those tickets lead to a cost, right? Head count or whatever. That exceed 120K. I mean, it sounds kind of cruel, but that's how they have to make the decision like that. And it's unfortunate, but like you said, it's not a hill to die on. It's like, okay, fine, if you're willing to deal with it. But just sort of, again, there is going to be an impact. Right, and I always say, well, compared to what? So we can do this and if we don't, this is what it looks like. But sometimes here's what you can do. Sometimes you can get a sort of a lightweight commitment to say, can we revisit this? Like, okay, I'm not gonna die on this. I get what you're saying. How do we help them get to profitability? Can we do part of it? Can we at least do X, right, on our way there? Maybe we don't do the full 120, right? What do we have available? What would make you feel comfortable? I'm always trying to negotiate something on the way because I forgot this book about negotiation, but I'm just trying to get you to say yes to one thing because once I get you used to that, somebody in the chat earlier said, the hardest one is getting from zero to one, you know? And that's kind of what this is. It's like, can I just get you to say we up the bandwidth or can we just buy one core switch or just something? But anyway, that's the logic that you're gonna be fighting. And I don't know if it's bad logic because again, you know, they're looking at the whole organization, which is why, as Tim said, it's very important that we do our homework before we move in and have these conversations. Don't worry though. I did get a little bit of a budget item to Nate's point. I got $6,000, so we're good. Awesome, rock and roll. That is, I think, one switch. But hey, better than nothing. More than nothing, yeah. One's gonna turn into two, Tim. It's just a matter of time. It's already not enough. I have like three places that switch needs to go. You know, again, I will briefly interject here. There's, and then Jason, I know you're probably gonna chime in with something, but the analogy that I really have found that explains my situation to my technical staff because they asked me for everything. I had one ask me for 50, 70s. I'm like, there's like 10 different ways I can't give that to you. Like what? Anyway, it was one of my junior techs. He's a great guy. Victor, if you're watching, I'm sorry. I didn't mean to call you out. But just, okay. You know, back in like the days of muskets, right? They had the powder horn. That was a thing they carried on them that had a finite amount of powder in it. Are they going to load their musket and shoot at the can on the fence when the enemy is attacking? No. I have shorthanded this to say, I'm not spending my powder on that. I'm not pouring in a shot and shooting at a can on the fence when there's a massive battalion of mounted cavalry coming my way. I kind of have to send the powder that direction. That's been huge to like help my technical staff and honestly, some of my like executive colleagues kind of understand like, look, that hill I'm dying on, right, I have to evaluate all of these little intangibles and this is a shorthand to do, you know, to explain, yeah, no, I'm not wasting the powder on that one. Just feel free to steal that one, attribute it to me or not, I don't care. But I'm kidding, don't. Please don't. No, that's good. That's good. And I think, you know, obviously you two both really covered this well. I think the only thing that I specifically would chime in with here is, I try not to use like that fear and uncertainty to say, well, hey, if we don't do this, here's something that's gonna happen. But to kind of Tim's point, if there is something that can happen with a negative effect, right, whether that's something like a compliance or fines or even something that other companies have dealt with when they've had to clean up similar messes, coming in with that information to say, look, I'm not saying that this is going to happen, but for a company our size that ran into problem X, here's what the typical costs are for that, right? Or on the other side of that to say, hey, as a business team, what if I told you that we just couldn't, we couldn't ship any product for three days? What does that mean for us, right? What does that mean for our bottom line? What if I, you know, here's what that means if we're in like an off season, right? A slower season. Here's what this means when we're right in the peak of a season, right? So I think it's going in with that right information, but being able to express it in a way where you don't get that like chicken little that happens, right, where you are suddenly become that person that's always like negative and that individual that always says, well, I'm spending money and here's the downsides to everything and just everything is terrible unless we start throwing money at it or throwing processes or systems or whatever that looks like. So it is a really fine line because you do obviously want to be able to say, hey, here are hard sunk costs that others have talked about during this, right? This isn't just numbers we've made up, right? You know, these are organizations that have disclosed these. So I just think that those are items to go in with and that can definitely be a tricky kind of item to navigate. Some of your executives will be very much not concerned by that, right? Or they'll have a little bit more openness to say, well, yeah, that's definitely something I've seen that. I know what happens when somebody's antivirus software goes out and we don't have planes for a week, right? So like they're like very much open to that. And obviously others that say, well, that's not gonna be us, right? We're too small for that, right? People aren't interested in that. They're not gonna target us, right? So I think it's going back to building those relationships and knowing your players, right? But the two of you obviously covered that well, but that's just my two cents on that. Yeah, yeah, no, that's great. I wanted to answer some of the questions in chat too, because I think that there are some really good ones that we could talk about, you know, not just in chat, but on the stream. Ryan says, when working with a fully remote environment, what are ways to help increase that rapport with the other departments since you can't walk down to someone's office? I'll say what I said in the chat. I have, yes, my calendar takes a hit, but it is so worth it. 30 minutes a week, biweekly, monthly, quarterly, I would probably go as far as monthly. Like that's about as recurrent as I would let it slip. Having that cadence, even if it's like that 30 minute meeting is five minutes of you just, hey, anything come up that you're aware of? No, same on my side. All right, great talking to you. How's the family? Right, those types of things. Seriously, that has been huge. Number one, I've made a lot of friends in this organization I didn't know before meeting like this. I have actively repaired relationships with departments that have been suffering. When I first came in, there were some preconceived notions about me that I couldn't really help because of the circumstances to my coming up to VP. I beat that into submission because I just got in front of them and showed what I could do. And then, obviously it is just nice to see people face-to-face. If you're fully remote, yeah. I mean, if you don't have an office you can go meet in, then it's really good to just get in the same room with a digital room with somebody like we are here. It's great to see everybody here and in the chat too, just for those reasons. So, 30 minutes on a calendar, make it even 15, right? But it depends on what it is. But it depends on what it is If it's HR, maybe give it a little more time because they're gonna have some you know Hey, can we tweak the process for terminations or finance? Hey, we got to talk about budget cycle But if it's you know, your QA department, maybe you don't need a full hour But it's nice to see them and it's also you're just showing that you are passionate about what you're doing. That's huge Just in and of itself Yeah, oh, sorry go ahead night So I was just gonna say was just so sort of an offshoot, yeah, we'll play the mute game, right I was gonna say a real offshoot So when I worked completely remotely with a with a consulting firm, obviously we were spread all over the place One thing that actually sounded really lame when we did it was like happy hour stuff. So we would Like every Usually like every two or three weeks We would essentially put like a half hour on the calendar and everyone would go grab like their favorite drink, right? And we would just kind of sit around and we would say hey tell me something cool that somebody worked on this week Right, so it got like sort of that water cooler and it eventually became more than just like tell me about this project You were working on it suddenly became hey, you know last weekend I was working on laying papers from a patio right and here's some craziness that I happened and then suddenly everybody is like Oh, yeah. No, I did that and oh, here's some gotchas and things. So It sounded and admittedly I was I was very skeptical about it So I was like, oh this seems crazy. Like I'm gonna sit on a zoom call. Like it's just another meeting But it was actually really kind of fun and the group really resonated Because they the same kind of feeling that you mentioned in the chat was how do you do that remotely, right? Like I don't I can't just get up and walk across the way to have a you know Business conversation a conversation about what I'm working on or even just a personal one, right? Like it's very difficult to kind of build those relationships Especially if you're not actively reaching out to say hey team I just want to put some time on your calendar and just talk right so it's kind of a cool way to do that You know your mileage may vary depending on your your your individuals, right? It may it may resonate it may not but for us it resonated once I realized that we were talking about things that weren't work-related You know, even for that, you know half hour or 45 minutes. It was just really interesting. So my comment there Yes Zoom I I use it all the time My entire team is all over the place in different time zones I want to touch on a point that that Tim made that I thought was very good and this comes from My whole nature and living systems. It's important that those feedback loops are as short as possible And the reason for that is because you cannot respond to something that you don't know about So if it's taking you a month or you only check in every quarter, then you can only respond within that time frame So so that's one's very important. It's the cadence It's that rhythm get on that calendar if it's just 10-minute check-in zoom with each member of your team or each department head Doesn't matter so much But it has to happen and you have to stick with it as Tim said is really worth it number two in those conversations My question sort of goes something like this. What's the number one problem? That you're dealing with right now that if we could solve it Would take your headaches away you have to understand what's really important to that person that you're talking to and It may not have a technical as Jason said earlier. It may not have a technical solution to it at all But but that's what's building that relationship that I'm actually here to help you solve your toughest problems And really that's what a strategic Partner does that's why you hire them so Number two, that's what we want to do is really get a sense of what's important to them And if you can't do anything, then you go, you know, I go. Okay. Well if we can't do anything There's not a technical or IT solution Give me something else. Well, what's number two and what's number three once you get this all what moves up into that next that next spot? And again, the most important thing is it's the cadence, right? Just make sure that once you start it that you keep it going you keep the distance between those conversations as short as possible It's not micromanaging. It's just again. I can't respond and I can't plan effectively if I don't know what's going on Yeah, absolutely another question That Tim you had responded to but Duncan said Right now we're using five different programs by consolidating down to one We would be able to do more than those five separately, but it's also a little more expensive I can explain and they understand why it's good to have apples to apples if it's cheaper But how do you explain the difference in cost for things the original five programs don't even do? There's a ton of new things that we aren't even doing that. We should be doing right now that the one program would cover So I'll just jump in on this one. So there's two ways to look at this one is operationally Okay, so We aren't there some things we're not doing And so the question I'm gonna play the devil's advocate here is so what we're not doing them. What does that mean? So the way you answer that question, what does it mean to the business? Either in time or Money, right attention. What have you that's what they care about So if we aren't doing these four or five things and that's costing us X doesn't always have to be money It could be time. It could be in productivity, but it has to be in some measured way Why does it matter and so that's the question at the end of the day that they're always gonna want to know The answer to it's not always just that it's cheaper because the there's a difference between price and cost Okay, right. The price is kind of what you pay up front. The cost is what you pay over time So sometimes the solution could actually the price is more But the cost over time is cheaper because you can now do these other five things that were costing us because of extra time spent or lack of efficiency or or so forth And to kind of chime in there as well you know with having multiple systems right that you're thinking about doing consolidation for one of the big questions that I would ask to this is Who's driving that discussion, right? Is that discussion being driven just like Nate said by like their Desires or what they think is like broken Because you also have a better opportunity when the business unit is driving that Then you would from your perspective depending on levers that you're pulling and pushing on If you're partnering with the business and the business is the one coming you to say Hey, it really stinks that I have to go into three different programs to do my job and you know Tom over there He goes into five different programs to do these individual components boy That's a real pain in the butt right and they can help with building that case and then also getting Getting you the opportunity to say the right things and to put together Hey the business actively wants this so then it becomes more of a business and strategic driver than it does about a technical Hey, I'm trying to help You know minimize program usage or sprawl that we have in the environment the advantages It has the effective opportunity to do both of those things But I think it really drives you really drive that from the business side I know we said that and it's it's really an ongoing theme that we have here. But I think that's what That's what makes the difference between a successful Successful relationships that allow for you to keep your seat at the table and to continue to grow So that you're not just that person that's hammering in a solution into a hole that may not necessarily fit Right or that individual that you know, we've all Potentially talked or heard about people in the past where you say hey, yeah I really like this platform and everywhere I go I implement it Right regardless of whether they have something else regardless of whether they like what they have, you know There there is that opportunity for individuals to say I've used this before we're just jamming it in right? And I think that that does that that does the potential for a disservice for a business, right? And that may have something else that already is doing that or is a good fit for another reason So I think it's definitely something that you want to keep in mind right optics optics optics I tell the team all the time right my job is is managing optics, right? I I am here to help you guys get what you need and to remove roadblocks And unfortunately that also means I need to make sure that perception matches reality Right because people's perception is their reality and when those diverge, right? That's that's where then I have to come in to help kind of drag those back together from that perspective, so I Lastly just share a real-life use case. I Was working at a nonprofit so I understand you're paying Tim and the computers in the accounting office were 10 years old and they didn't want to buy new computers and The computers were slow all the accountants complained about it all the time And I would go to senior management and say, you know, they're really slow. They're 10 years old They're slowing down the work. They're slowing down the work Nothing they didn't care because it wasn't their computer So I tried something different. I went and talked to the accountants and I said How often are you rebooting these machines every day when they install? Well, at least once or twice a day So I said, okay, I'll take once a day and I sat there and I timed it and I said, okay Once you do the cold restart, that's okay. So we're talking about 10 minutes So what I did is I just did the math I said, okay 10 minutes a day times 10 accountants times five days a week Times right, whatever 2,000 hours. However and did the math said so this is the total time that we're spending rebooting Then I went to HR Redact all the other stuff, but I need to understand what are we paying annually in salary when I did the math? I realized we're losing thirty thousand dollars a year rebooting computers You know how much new computers cost? 30k. So when I go in now, I'm saying look They're rebooting at least once a day sometimes twice a day Annually, it's costing us 30k in Productivity the computers are 30,000 and after year one It's all gravy years two three and four. It's a freebie, right? So just the savings and productivity paid for the computers So sometimes it's just framing it in a quantitative way and sometimes getting creative To get to get the funding but that's how they needed to see it because when I just talked about it operationally nobody cared I'll point out some of the things that just happened there in that in that process, right? And I promised eight and I didn't coordinate this He went and saw the problem firsthand right that it's not really even enough to look at the ticket history Go see the problem for yourself Once you do that you understand, okay, I see whether you genius stuff, but then Notice that we kind of transcended the bounds of what us IT leaders are usually comfortable with of like I we need new computers Because hardware lifecycle policy, you know caveman speak, right? Yeah No, we need it to salt like that calculation that happened is not something that we normally do I'm I'm with I am arguing for Nate probably so Nate feel free to repudiate me, but we should be doing that We should be arguing From perspectives that are not necessarily. Well, that's the tech guy Am I I'm pulling pen out of my pocket protector and tell you like that's that's the quickest way to get ignored, right? But if you start speaking their language and you start exactly what Nate did and reply to it in here's the man hours wasted You're number one you're speaking your language number two, you are exercising creativity that is noticed and seen and I Think it's all about just being different than the norm And and in a positive way like you're trying to be a positive change agent here. You're not trying to just Unilaterally like Jason said unilaterally import your favorite stack I serve as the great filter here because I have people come in and say I literally had one of my technicians I'm picking on them Hey, can we switch everybody to proton mail and use the company phones with graphene OS? Like look, but I hear you 100% if I had everything I wanted and if I was in the shoes back in 2016 and Proton existed right they didn't use it, you know, then yeah, that's a decision we could consider. I Can't do that right now. There's a hundred thousand reasons for that I'm I'm the great filter here, right? I am because I understand the business I can't Let certain things happen Even if technically all of these things they make perfect sense Because they're just not a good fit for what the organization is trying to do It's my job to understand those constraints and operate in all sectors internally with your team Externally with the rest of the business. That is your job. I Promise you you'd like to take that Understand that that is as an IT leader. That is what you are here to do Not just manage people not just you know Make sure budget spreadsheet equals zero and of you know, like that zero and of, you know, like that's, that's, there's those parts of it. You are the vibe checker, I guess. Um, maybe don't put that as your title. No, sorry. Go ahead, Jason. Oh, no, I was just going to say, I think that's a great comment, right? Like the, our, our goal, right. Is to help evaluate whether it's a system, a stack, a platform, and to help merge that with, with the business and what they, what they need. So I think that's just a great call out, um, there, right. Being the great filter. Um, I love that. Yeah, I, I think that's great too. Um, I'm feeling we're going to get a lot of great content from this, from the stream. So, um, yeah, uh, we are at time, so I appreciate y'all, uh, uh, joining us. Yes. Changing signature to vibe checker. I, I honestly think that's great. I mean, my, my thing in here is community manager slash chaos wrangler, because that's, that's just what I do at, at Ninja. So, um, I'm all for fun titles like that. Uh, but yeah, um, I think that is, uh, that is all we got for today. We'll be back in a couple of weeks. Let me double check which event this one is. Oh, it's about vendor relationships. So from, from problem to partner and actually Tim, uh, when we were backstage was talking about how he got to go to a Spurs game, um, on behalf of a vendor. And, uh, I, I think that's one of those things that you can get from a vendor relationship. So, um, yeah, we'll be talking about kind of building those positive vendor relationships. How you source vendors, what you should be looking for, what you should be looking to stay away from things like that. So we'll be back in a couple of weeks for that one. Um, but in the meantime, I hope you'll have a good rest of the day and, uh, thank y'all for joining. I really appreciate it. All right. Take care y'all.

TL;DR

  • Resistance to modernization stems from fear of losing control, predictability, or job security—not opposition to IT—requiring leaders to address "how does this affect me?" concerns through clear communication about role evolution rather than elimination.
  • IT leaders must build relationships across the organization through regular listening tours and firsthand observation of workflows, partnering with business units to let them drive modernization discussions rather than imposing technical preferences.
  • Quantifying the cost of inaction is essential for overcoming budget resistance—one speaker demonstrated $30,000 in annual productivity loss from daily computer reboots, reframing a hardware refresh as an investment that pays for itself in year one.
  • Successful modernization requires incremental wins, regular communication cadence with leadership, and knowing which battles to fight—IT leaders must act as strategic partners who speak financial language and understand business constraints.
  • The "great filter" role means evaluating whether technically sound solutions fit organizational culture and constraints, transcending comfort zones to operate across IT, finance, and executive domains while maintaining trust through transparency.

Understanding Resistance to Modernization

The panel opens with a candid discussion of the most common forms of resistance IT leaders face when proposing modernization initiatives. Jason Granite from Wish Farms describes industry-specific resistance in agriculture, where generational farming practices create a "we've always done it this way" mentality. Tim Lanning from SGRC Texas shares his experience at a 700-person nonprofit where staff came from state agencies with different technology expectations. The speakers emphasize that resistance isn't malicious—it stems from people acting in their own self-interest and fearing loss of control, predictability, or job security. Nate Payne reframes resistance as employees asking "how does this affect me?" rather than opposing the idea itself. The discussion highlights how modernization anxiety has intensified with AI and automation concerns, making it critical for IT leaders to communicate that efficiency gains won't lead to headcount reduction but rather role evolution.

Building Strategic Relationships Across the Organization

The conversation shifts to the importance of building relationships beyond the IT department. All three speakers stress that IT leaders must understand business operations firsthand—not just through tickets or reports. Nate advocates for regular "listening tours" where IT leaders spend time with different departments to understand their workflows and pain points. Tim shares how his direct reporting relationship to the CFO shapes budget conversations, requiring him to justify technology investments in financial terms. Jason emphasizes partnering with business units to let them drive modernization discussions, noting that when the business actively wants a solution, it becomes a strategic driver rather than a technical preference. The panel agrees that IT leaders must transcend their comfort zone of technical specifications and learn to speak the language of finance, operations, and executive leadership.

Quantifying the Cost of Inaction

A major theme emerges around preparing for resistance by quantifying both the benefits of action and the costs of inaction. Tim recounts proposing a $120,000 network refresh for a 40-year-old campus, only to be told "not until they turn a profit." He emphasizes the importance of having cost-of-inaction data ready before the conversation, showing exactly what degraded performance means in operational terms. Nate shares a compelling case study from a nonprofit where 10-year-old computers in accounting required daily reboots. By calculating the time spent rebooting (10 minutes daily per person) and multiplying by hourly salary costs, he demonstrated $30,000 in annual productivity loss—exactly the cost of replacement computers. This reframing transformed the conversation from "expensive hardware refresh" to "investment that pays for itself in year one." The speakers stress that CFOs compare the modernization cost against the quantified impact of doing nothing, making preparation essential.

Practical Tactics for Gaining Buy-In

The final segment focuses on tactical approaches for moving modernization initiatives forward. The panel discusses the importance of incremental wins—getting from "zero to one" by securing small commitments that build momentum. Nate suggests negotiating partial implementations when full budgets aren't available, asking "what would make you comfortable?" to find middle ground. Tim advocates for regular communication cadence with leadership, recommending weekly or biweekly check-ins to maintain visibility and avoid surprises. Jason emphasizes the role of IT leaders as "the great filter," evaluating whether technically sound solutions actually fit the organization's constraints and culture. The speakers agree that persistence matters, but so does knowing which hills to die on—some battles aren't worth fighting if the organizational risk is manageable. Throughout, they stress that successful modernization requires IT leaders to act as strategic partners who understand business context, speak financial language, and build trust through consistent, transparent communication.

Chapters

0:00 - Welcome & Introductions
5:25 - Understanding Resistance to Change
12:37 - Common Excuses & Objections
21:15 - Building Strategic Relationships
30:58 - Cost of Inaction Analysis
48:28 - Communication Cadence & Transparency
53:42 - Real-World Case Study: Productivity ROI
59:08 - Wrap-Up & Next Event Preview

Key Quotes

9:51 "People act in their own self-interest. When you want to understand resistance or behavior, just start there. What it means is there's something about what you're proposing, the person is always going to say, how does this affect me? ..."
10:35 "Here's what they're really saying. What they're really saying is, I'm concerned because there's something about the way we've been doing it that is predictable for me, that feels solid, that I really have a grasp on, and I feel I'm going to lose that if we make those changes."
15:50 "I think there's definitely a feeling of that modernization, where it gets lost sometimes in the, well, we're modernizing to reduce headcount. The workforce immediately says, well, what does that mean for me? ..."
32:36 "I go in and I say, hey, here's how it'll cost you $120,000. I get told, no, not until they turn a profit. The only way you win in that situation is because I prepared for that. I said, look, here's the cost of inaction."
54:32 "I timed it and I said, okay 10 minutes a day times 10 accountants times five days a week. I realized we're losing thirty thousand dollars a year rebooting computers. You know how much new computers cost? 30k."
55:44 "Sometimes it's just framing it in a quantitative way and sometimes getting creative to get the funding but that's how they needed to see it because when I just talked about it operationally nobody cared."
56:53 "We should be arguing from perspectives that are not necessarily, well, that's the tech guy pulling pen out of my pocket protector. That's the quickest way to get ignored. But if you start speaking their language, you are exercising creativity that is noticed and seen."
58:11 "I serve as the great filter. I understand the business. I can't let certain things happen even if technically all of these things make perfect sense because they're just not a good fit for what the organization is trying to do."

FAQ

How do I justify modernization costs when executives say "if it's not broken, don't fix it"?

Quantify the hidden costs of inaction in terms executives care about—productivity loss, time waste, or operational inefficiency. One effective approach is calculating time spent on workarounds (like daily computer reboots) and multiplying by hourly salary costs to show annual losses. Present modernization as an investment that pays for itself rather than an expense, and prepare this data before the conversation so you're ready when resistance appears.

What should I do when I propose a modernization initiative and get rejected due to budget constraints?

Don't treat rejection as final—negotiate incremental wins by asking "what would make you comfortable?" or "can we do part of this?" Getting from zero to one is the hardest step, so securing even a small commitment (like one switch instead of a full network refresh) builds momentum and demonstrates value. Also establish a regular communication cadence to revisit the proposal as circumstances change, and know which battles are worth fighting versus which you can defer.

How can I overcome resistance from employees who fear modernization will eliminate their jobs?

Address the "how does this affect me?" question directly by communicating that efficiency gains will lead to role evolution, not headcount reduction. Partner with business units to let them drive modernization discussions, showing how new tools will make their jobs easier rather than obsolete. Build trust through regular listening tours where you observe workflows firsthand and involve employees in shaping solutions, demonstrating that modernization serves their interests rather than threatening them.


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