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397- Six Times Private Equity IT Playbook w/Bradley Stokes · You've Been Heard

• 0:09
  Speaker A: All right, everyone, welcome back to. You've been heard, really stoked Today to have Mr. Stokes on the show. Four times CIO, six times private equity digital transformation leader. I think you probably have the best headline that I've seen on LinkedIn for a CEO. You introduce yourself, Mr. Bradley Stokes. Let's go, man. Talk to me. What does six times private equity mean for you? What are you doing? How do you get started? Give me the short story.
• 0:36
  Speaker B: Yeah, so obviously been in IT for a long time, kind of fell into private equity through technology startups back in the day and have now done that, as you kind of mentioned, six times. So currently in a private equity opportunity. Right. And so, Jillian, my sort of mo, if you will, is brought on to private equity owned businesses to either help with relaunch, course correction, standardization, consolidation, and then sometimes obviously brought in for more just business enablement. Right. Business value generation. So just a. It's a model I've been in now a long time and so just kind of used to the template I follow and it's a good thing and people seem to appreciate it, hence why I've done it six times now. And so, yeah, so the goal for me always is to provide value, drive transformation. And I think for a private equity standpoint, that's what they're looking for. Right? Like how do we get quick wins, how do we build value quickly so we can exit companies and make a lot of money and I hope enable that.
• 1:35
  Speaker A: This is actually really exciting and just in the vein of what we want to try to. I guess as far as the podcast goes, you've been heard is really amplifying IT voices more from a business standpoint and making sure that they not only just have a seat at the executive roundtable, but are actually heard and respected and their advice matters and should not be skipped over because when we skip over the people that touch every aspect of the business, we end up with problems. So, so much to ask. Just from that initial piece, you said you have a recipe, so to speak. If there was three steps, five steps, seven steps to your IT leader playbook, what would that be? Where do you typically start? And from a technology slash business standpoint, here, right, there's we're trying to get rid of this, us versus them, the department of it. Then there's the business. Right. It's really not that. And I think you have a lot of experience with again, preparing companies to probably exit or sell or move on to the next amazing part of their life. What would those three steps be in your recipe or Five steps.
• 2:37
  Speaker B: Yeah. So to your exact point, like, the first thing I do is what I call the goodwill tour, which is going and visiting all the leaders, executive team, board members, and then start to work my way down to other leaders, subject matter experts, and then eventually do get down to the boots on the ground, right. And I typically visit all the sites, right. As well. So like my current company, six companies, we own 13 or 14 sites across those six companies. So I start on the relationship building part, right? Because to your point, like, at the point in my career and at the point where I think it is now shifted to where the business enabler, right, Like, I have to make those relationships work. I have to understand what the business needs are, not only from a strategic standpoint, but like, again, how do I enable the people, boots on the ground, folks that really, to some degree are the change agents, you know, for the business. And so that's where I start at. So that's number one.
• 3:33
  Speaker A: Just to break that down. Sorry for interrupting you. But the goodwill tour, are there like, is there like a template for that or specific questions that you like to ask or anything?
• 3:41
  Speaker B: Yeah, absolutely. So, yeah, they differ, right. Based on the audience, right. So, like, I have, I start kind of at the board and executive team and the questions there more around strategic view, what are their goals from a business standpoint, whether it be revenue, whether it be efficiency gains, whether it be ebitda, whatever that is. Right. Like, so I have clear understanding of what they're trying to achieve. So I can then start to think about what can I do to help that process along. And then I kind of move down to the sort of next level of leadership, which is a little more tactical, right. Like, people have problems with a certain tool set, have problems on the shop floor, things like that. And then I get down to the last level, which is sort of the boots on the ground, which is enabling those folks to be more efficient, to have some vision back up to the top, right. Which seems to always be lost, right. Like boots on the ground folks don't seem to have a lot of time, good understanding of like, the work they're doing and how it actually contributes to the larger strategic focus. Right. And so I try to marry those things together because the better we do that, when I do go to push like a new technology, right. That adoption is much easier, that change management is much better because I've enabled people at the boot level, right. To kind of get engaged and be a part of that process.
• 4:56
  Speaker A: This is really, really good. Really good. I think where there's a big disconnect sometimes. I mean, you tell me if you remember this from the past or whatever it is. Even technology leaders not understanding really what the main goals of the business are or what's keeping their C suite up at night. Most IT leaders don't have an Internet problem. They have a management problem. Multiple locations, multiple providers, multiple, multiple bills, different contracts. We help IT leaders make Internet boring again by consolidating visibility, billing support and monitoring without changing providers or forcing upgrades. If nothing needs fixing, we'll tell you that's vendor neutral advisory. Just go to you've been heard.com and answer the seven questions to simplify, streamline and save.
• 5:45
  Speaker B: Yeah, absolutely. No, that's. I mean I think that's where as we get into this industry, like as technologists, like we tend to sometimes chase shiny objects, right. And the latest whiz bang tech and aren't thinking about the alignment to the business right. As much as we are thinking about trying to solve technical problems. And again, as things have changed across our lifetime, like, right, like the technology is enabler, but like now those things are closer together. But if you don't have the business understanding, like you're lost, right? And so like I took some interesting questions, so I took some kind of curious steps around that. So I felt like I was in a place in my career where I felt like I understood the business, but I didn't see my job journey that I was really getting the roles that really kind of demonstrated that knowledge. And so I actually went back to school and got a business degree, even started my MBA because it was almost like I'm trying to check some boxes to demonstrate further, like I know the business. I think it helped in some ways. But in some way I think it was more like I checked the box, right? And so not sure I would do that again. And then my background. But like at the time I was desperate to demonstrate to the business, like I understand the business, right? And so I think that is always a gap, right? And has been historically, as we have reported to CFOs and CEOs and CEOs and anybody and everybody but the CEO. And so I think trying to again be more of a business partner kind of drives that.
• 7:05
  Speaker A: Okay, so a lot of people make that mistake, young people make that mistake. I need to go back to school versus maybe get a job and just work really hard and make some money. I learned all that stuff the hard way. And by the time I was whatever 28 or 30 or something, then I was like, oh, I Wish I had not done this. So I guess what was the big aha moment for you? Was the going back to school helpful or did that not bring the business focus or the business knowledge that you needed? Or was there some kind of mentor or something that just hit you hard? Like what was it? At what point did you. Oh, so here's the question. At what point did you realize you're no longer like just an IT leader, you're now a business leader?
• 7:46
  Speaker B: Also, I think I realized that prior to going back to the work on those degrees because as I started to think more about what I was asked to help solve for, it was business problems. Right. And so I think as that mind shift began, that's where my interest in sort of going back to school started because I was like, what do I need to do to demonstrate that I get it? And yeah, I mean, I still think I always am a big advocate for college education, but like, maybe not for the traditional reasons. Like I've had someone, I've had these conversations a lot, especially around computer science degrees and things like that. Because the tech changes so often. Like is there a value like computer,
• 8:21
  Speaker A: computer science worthwhile degree or not waste of time.
• 8:24
  Speaker B: Yeah, yes, but not for the reasons I think people. So like the questions I get asked around that are like, well, the tech changes so often, Brad, like, so why would I go pursue a tech degree? Right? Look, you, you went and got a computer science degree in the 90s and that was in Cobol, right? To use that today, right? It's C. Yeah, yeah, exactly right. So like my argument, so for education and, and at the college level, post grad, post high school level is still that sort of all the, So a couple things. So just the logic and, and how you approach problem solving continues to evolve and that still helps evolve that. Right? So I still think there's a lot of value in that. Not say you can't get that from real world experience, you of course can. Right? So I think it helps accelerate that path. Their part, which I think is probably more critical from a college standpoint is, and I see this more and more with like the kids who have been through college now is the sort of group project, shared responsibility process, bringing people together from different walks of life. And I see that value creation as the big value add from college. Again, not say you can't get that from outside of college, but I think it's an accelerator in a way. And then the last piece, I will always kind of now say from a college standpoint to some degree is the Networking opportunities that starts to open those doors that again, if you're a young person, networking is very, very challenging, very difficult, very hard unless you find a good mentor or coach. And so you kind of open some of those doors as well. And so that's the one I will advocate for. But it's maybe not for the traditional regions that people went to college for.
• 9:52
  Speaker A: Right, okay, excellent. So we've jumped around quite a bit. We got to with step one, which was the goodwill tour. What's the next step in your recipe?
• 10:02
  Speaker B: So this is my private equity experience. The next missing piece I seem to always find, and I'm talking about companies that are typically in that 500 million to 1 billion range. The PMO doesn't exist. So no project management office exists. And what I hear from those businesses is the reason why they're sort of anti it is that projects run poorly, go over budget, they have crazy scope, creep, et cetera. So the first thing I do typically is start that pmo, right? So that's usually the first person or people that I hire is people around project management, program managers, business analysts. Because that does a couple things for me. One the generally the next sort of step there I take is the first piece of that is they click and build out the portfolio projects. Because the business often has no idea like how much work is on the plate of it until we go through that effort and then we're like, oh, here's 200 projects. And then they ask the question, okay, when will we get those projects done with the current staffing in 25 years. So we can't work on 200 projects, right? So like, so that becomes the guiding force of like, okay, now we need to like have a steering committee, right? In, in the business. Executive team's going to support and provide guidance around where is urgency, where is prioritization, what products we going to work on? Because we're going to work on 10. That's the resourcing we have today, right?
• 11:29
  Speaker A: Let's build a Stokes app right now. And I want to know we're going to build this app, right? And it's going to be like a series of questions or something. I don't know what it is, but what does a small to medium sized business do that's not five to a billion dollars? What do they do that doesn't have good project management in place? There's gotta be some way to communicate like you said, moment of realization that oh wait a second, no IT department could possibly do all this. And I think that that's what again, a lot of this show is all about is that kind of mid market to Fortune 5000 space where you've got a handful of people responsible for anywhere, where the ratio of IT staff to end users is 1 to 100. Of course we don't say end users, we say customers. But for the sake of understanding, this is one to a hundred and that it's like your freshman year in college, like you go to your whatever philosophy 101 and you've got 300 students in the class and one teacher standing up front. How could they possibly get the attention that they need? They're not going to. So this step two of putting project management in place and understanding all of this in really kind of making people realize the problems in the business or the scalability factor or the ability to scale, but can't scale because we can't hit all these projects. What can we do for those people that don't have that? There's gotta be an app we can build. We must be able to ask like a bunch of questions. There's gotta be some things we can put in place. There's gotta be something that we can do to help communicate to executive management more properly the problem.
• 13:02
  Speaker B: Yes, I think you're on the right track there, Right. Like I think there is still, obviously, because it happens, right. In small businesses every day, right? So it is that sort of collection of questions and information gathered that you need to kind of demonstrate like where you're at, how you level set, right? How do you come that sort of meeting of like, this is where we're at, this is where we want to go. Right. And I still think that can be accomplished with small IT teams with the right focus. Right. So I think in the smaller businesses, what I'm seeing, and it really extends, even the businesses I deal with is smaller IT teams from an FTE standpoint. But then the partner relationship, the MSSPs of the world become the other driving force, right. In terms of how they get through some of this work, right. As well as all the fractional opportunities, right. Like fractional CIOs, fractional CISOs, et cetera. And so that's the way you start to figure out like this game plan of like we're going to tackle it this way based on our size. Maybe it's a fractional person, it's an msp. And then we allow the, the few IT people, we do have to kind of specialize in whatever IT is, right. Or we say, hey, we want to be really good at being help desk or Reactive.
• 14:10
  Speaker A: Here's the problem there because everything that you just said sounds like executive management making that decision and then saying we're going to let it take care of the rest of this. How does it argue that hey, we need more budget for this outsourced msp, we need more for this. And the reason why is this. Right.
• 14:32
  Speaker B: It goes back to where as we start to train IT folks like we start more closely with that sort of business minded focus because when they can talk that talk then you generally have better results in terms of what you're asked for. Right. Like I think that's their problem. I see with some places I've been at like I asked the question differently than maybe the IT director before me did. Right. And so just asking the question differently resonates with the business. And so I think that's where again trying to bring people up and mentor and coach them the right way, whether that be training in college or trade school or just how we educate people in general like to be the business focus piece relative to technology. I think it's how you overcome some of that. I'm not going to say it's easy. Right. Because I think that's a true problem. As you describe the small businesses struggle with.
• 15:17
  Speaker A: Right.
• 15:17
  Speaker B: Like the executive team tries to lead it right in the best way they know how and oftentimes it is misaligned with the direction of where they should go. Either they're doing shadow IT or bring in technologies that don't integrate well or don't fit with the rest of the business because they don't have visibility to that. And so I think it's just again trying to build the relationships and creating the partnerships and the business understanding.
• 15:38
  Speaker A: Is there a course for this? Sounds like we need like a course for senior IT leaders that have been in it for 20 plus years that still are asking the wrong questions or just not asking the right question the right way. Can you give me a couple examples are some of the most important questions that you would ask?
• 15:53
  Speaker B: Yeah, so like when I'm thinking about an IT project or a technology solution on implement like the things I'm trying to ascertain to to the resonate with the business will be what is the problem it's solving? Right. Like simplistically, what business problem is IT solving? Right. Not technology problem, but what business problem is IT solving? And then what's the value creation whether it be again we're going to see now turns created in the manufacturing shop floor is it going to be? We see some efficiency gains in a Certain solution. Are we going to have visibility data? Like, do we have really going now we don't have.
• 16:27
  Speaker A: Yeah, like, why are we even solving this to begin with? How about that?
• 16:30
  Speaker B: Yeah, yeah, like, right, so it's, I think it's oftentimes people just jump into a project, right? Like there's a whiz bang solution out there, whether it sees it or the business sees it. And then all of a sudden it's in place and like, was it the right solution? And do we have clear sort of deliverables or objectives to solve for? So I start there, right? And then I tie that to. Okay, well here's the problem we're trying to solve. Here's the cost of the project. And then try to marry those things together. Like this provides this value, but it's this cost, right. And so to start to bring those things together, to demonstrate like to the business, like, you know, we can do this, it's this cost. Do you, the business think that we're going to provide, create that much similar value out of like, are we going to find $1 million cost savings? We spend a million dollars on a solution, then it doesn't make any sense. Right. So trying to marry those things together.
• 17:17
  Speaker A: I think you tell me whether you agree with this or not, because people grew up in it and they end up in IT leadership. I don't know if they have the right resources or ever got the right kind of, to your point, business training or whatever. So which was why you went back to school. Do you have any, like, I know there is a lot, but I mean, what would your foundational books be? Your foundational. It might not even be a book. It might be this podcast, it might be something else. Is there anything foundational that you're like, man, this one just made such a big difference difference for me. I mean, it's like venture capital. It's kind of like this thing that's. Once you've been through mergers and acquisitions, you understand it.
• 17:51
  Speaker B: Yeah, yeah. No, and it's funny you said that because my book reading generally comes from recommendations from others. And so like I'm a more follower there than a leader. But like, I don't know, like I've had. So from an IT sort of soft skills, business skills standpoint, I have some success. So there's a one solution I use called pluralsight, which is a CBT online training. And I like that. And I've used it now for a couple different businesses because it not only has your typical IT train stuff in it, but it has all the other stuff, so to speak. And so you can kind of mold, like, I've developed training plans for my people based on what's in there. And it can be anything from presentations and public speaking to having some business understanding of breaking down ROI structures, et cetera. And so it has a little bit of all that. I'm not saying it's perfect, but I think I've used that with some success in a positive way because it has enough there to kind of get people started and thinking differently because again, typically they're looking at that CBT training as this IT stuff and it has all that in it. But, like, it really does have a good portfolio and library of like the softer business skills as well. And I've modeled that out for my team to say, here are the classes that you have to take. Right. And I generally start with simple stuff like public speaking and writing and things like that, although AI is helping with that considerably now. But like, because I think just IT people in general are just poor communicators. So I generally start kind of there and then work my way up to sort of business stuff, if you will. Yeah.
• 19:19
  Speaker A: So we've got at least a really, really good resource, pluralsight. Okay, so step one, the, the. The Goodwill Tour. Step two, what are we naming step two?
• 19:28
  Speaker B: I think it's PMO Project management.
• 19:30
  Speaker A: Ah, yes, yes. Yeah. PMO project management. Okay. And then I don't know, what's step three?
• 19:35
  Speaker B: Step three become a bit of the sort of people on the bus, right? Seats on the bus, sort of staffing assessment. Because especially in my world, the private equity world, we do typically, the companies I come into do a really good job being reactive, I. E. Help desk infrastructure, maybe even cyber to some degree. It didn't do a very poor job or anything else. Right. And so I'll have a glut of people in those areas. And so I spent a lot of time and energy figuring out, like, can I refocus people they have an interest in maybe data or PMO or enterprise application support or DevOps and start to think about how I could position those people and kind of back that sort of pluralsight piece. Like, then to figure out, like, where do I kind of move people directionally from a training standpoint? And then obviously I'm still going to have gaps right. On my seats on the bus. And that becomes a combination of going back to the business for either FTEs or partnering things out or just a little bit of the. Again, realizing what we are, who we are, and who we want to Be as opposed to trying to be all of it. Like. Right. Like typically in my world I tend to shy away from any software development because that's not a strength, that's not a core of the business I'm in. Right. But a lot of times we still have a need there. And so I would just find good partners that can help develop specific things for us that we need outside of what's off the shelf.
• 20:48
  Speaker A: Okay. Goodwill, the PMO by getting the right people in the right seats on the bus.
• 20:55
  Speaker B: Anything else, then my next one always is data. Because data becomes the next big player. Right? Because especially in the private equity world because you're talking about lots of different companies coming together. So data normalization, data rationalization, data governance. And now in the world we live in now, that's the foundation for AI, Right. Which everyone wants to see. And private equity is no different. Right. The board is chasing some of those shiny objects too, or want to, they want to put something on their sort of flyer that hey, we, we have AI in place at company xyz, right. So that becomes a, a bit of a driver. But then I have to level set right with until the data is really in the right place. Like that's not going to happen because it doesn't make sense for it to happen. Right. So data is probably the next one I start to jump into very quickly.
• 21:37
  Speaker A: Okay. So you just diffused kind of something that I see as a problem recently. A place where there could be a big disconnect between it and executive management. And out there hearing every, seeing all kinds of shiny objects and the new shiny object is obviously AI and they're going read about it in Time magazine, if that still exists or they're hear about it at a conference, they're come back, hey, we need to go all in AI right now. Where are we at Team go. And I'm sure a lot of people are dealing with that. And you just diffused it in like one sentence which is okay, well how clean is our data or whatever wanting to need to say there and this needs to get there started first. Yeah. Where are we actually at in the AI journey and how big of a difference is it really making?
• 22:16
  Speaker B: Yeah, yeah. So I think that's where you, it's, it is level setting right with the business in terms of that. And you know, I see it in my current role. And again, they're not like heavy pushers towards. I mean, I guess I'm blessed a bit in the current private equity scenario that still exists. Our private equity provider is fairly Hands off. But they see the same things on the news everybody else does, right. So they're asking, they're asking good questions. But I think it again is just bringing that visibility back to the executive team and the board to say like, hey, we're just not ready. Like I get that you want to go down that path and then maybe if there's significant push to kind of get there, there's safer ways to kind of take steps towards that end. Meaning like there's most every application, I mean you name it, like whatever it is, enterprise application is touting an AI component to it. And so I think there's opportunity still in a safe way for individual solutions to say, hey, I have SAP maybe as an example, right. And they have an AI piece or Oracle and they have an AI piece and it's a little bit less risky path to take with an inherent built in AI, but again very limited in scope. Right. And so I think that's where I've been kind of directing businesses more recently is like that's a safer, safer play right now. But like the bigger push is, which is why you're seeing data everywhere, data companies, data, data, data is we got to get the data, right? And so that becomes the biggest next push. And my example where I'm at now, like one of the first things we did here is build out an Azure data warehouse, right? We're layering our, layering on power BI we're bringing on, I mean all my new hires are all on the data team, right? Data engineers, data scientists, data analysts, right? Because that is the, really the play that's going to provide the most value and that not only just visibility for the business but like AI readiness, right? That is the next step, right? To figure out there's ways because in our business, like where I'm at today, the golden grail of sort of mechanical construction is and bid management, estimating and there's tons and tons of data out there if we can only leverage it. But part of leveraging it is it has to all be harmonized, right? And so that's what the step we're taking. But again, back to the sort of fear mongering it goes on like not replacing people, right? Like that's not, that's not going to happen in, in the near future, right. But like will it accelerate people? Yeah, and it should, right? Because if someone's going to estimate something, we probably estimated something like that a hundred other times. So if it's like chatgpt on steroids, like can we get close, right? Like, can we get 80% of the way there that I can hand off back to the estimators? Like, here you are, here's 80% of the work. Now you just got to put those, you know, finishing touches on it. We turn things around, they're more accurate, we capture data better, all those kind of things, right?
• 24:54
  Speaker A: So it's been transformational as far as our show. It hasn't replaced people, it's added more. So we've been able to process transcripts and put together infographics and break down trending topics in them. Matter of minutes versus days. And then it allows us to deliver more. Deliver better. More. Yeah, Better, faster, stronger. Okay, so before I. There's a lot to speak about the data there. They have a lot of questions, but is there a step five after data, it's like, now we sell, like, what's your step five in your recipe?
• 25:28
  Speaker B: In the, in the P world, Step five is then sort of, I'll call it standardization and consolidation. So, like, we tend to have similar apps, but different apps across the business. Like, starting to find those synergies, right? Like, that's a very simple one, but, like, that's the next one probably, honestly, in my world, because anywhere I'm at now, like, we have Procore as an example, like the Procore version this at one company, Procore version that. And our comments, like, just trying to like bring that together, right? Because this makes sense. It's easier to support, easier to license. There's value creation just from cost savings from the licensing standpoint. So that's probably the next big one. That always seems to be a pretty common one in the private equity world. Is all that consolidation and standardization.
• 26:11
  Speaker A: Okay? Is there anything we're missing there? I mean, so from getting to know the business, to project management, to making sure we get the right people in the right seats in the bus, to data cleanup, to consolidation, it sounds kind of full circle. I really like that. Is there anything we're missing there?
• 26:27
  Speaker B: That that's. I mean, I think that covers to your. To your point, like, that's probably 90% of it, right? Like, there's going to be arbitrary things that kind of hang out there, right? But like, that's generally the, the bulk of it. Is that.
• 26:36
  Speaker A: Right.
• 26:36
  Speaker B: Like, my last role, I did have some custom software stuff I inherited, right. Which became problematic. I had to do some modernization and you find some of that stuff. But like, it's never. Those things are always unique on their own, right? That was a fun one. That was a, A DOS application that they Affectionately refer to as DOS because they were so young, age wise there, they didn't realize that DOS was actually the underlying platform was built on. So just called it dos. So but again those are one offs. Like I think you see some of that legacy stuff that's out there, technical debt as we often refer to it as like. Right. So there's some opportunity there. But like it's hit and miss, it's never the same. And so we always take a look at it because from a sales standpoint, right, like much like I don't want to deal with it, people that buy us don't want to deal with it either. Right. As much as they can. So trying to figure out how we either replace it with off the shelf stuff or at least modernize it. So like it's in the latest and greatest sort of generational code and can be supported by somebody else, things like that. But that's probably the next sort of kind of biggest thing that's out there. But again it's, I have none of that where I'm at today. I had a big win in my last company, so it's, it's not always on the template, so to speak.
• 27:42
  Speaker A: Okay, so back to the data thing. I feel like data could almost come second though. Like how it's almost like data needs to be involved like along with the project management, along with making sure we have the right seat in the bus. I feel like it's something that we need to get involved more early in a lot of these conversations because it affects so many other things. Yeah.
• 28:02
  Speaker B: And I think that's worth your point. Like when I think about the pmo, like one of those pieces I implement, that's part of that process is not just the collecting of all the sort of current projects is I begin using that sort of PMO intake as the gating process. And that gating process then allows it to have a lens in certain different objects. Right. So like as a project comes onto our surface to evaluate, like now we can look at and say, okay, what's the data back end? What's the integration layer look like? What's the cybersecurity look like? So we'll take those, that lens of it before we even kind of move it to the executive team for review. So to your point, like they are, they are definitely related, but like that's how they're related today in my world typically because jumping right into the data without having some of those other things in place is a little bit just premature. And I'll say they don't all go kind of pretty fast. Like, private equity in itself is pretty darn quick. Like, I've been in my current role nine months and I've already kind of gravitated through, obviously, Google Tour, PMO staffing. Now I'm in data, right? So I've already done that that quickly. Like, that's just part of the process. So it's not like there's these big gaps. But like, that's kind of how we begin to tackle the data problem. Integration challenges is it becomes part of the intake lens. Like now we have to evaluate that before we even kind of move it to the steering committee to say, hey, here's a project that so and so from business department, whatever wants to move forward and get some view on. We've already taken that lens at it. We've also part of that intake process also forces the sponsor to build out. What's the roi? What alternatives have you chosen? What are the risk? If we don't do this right, what's the cost? We start to build out like manpower resourcing as part of that process too. So before it even gets to the steering committee for review, we captured as much of that data as we can to say, here's the project. So then when the steering committee looks at it, they can basically quickly say like, oh, I see, there's a lot of work to be done in it, right? Like, so maybe we don't want to do that one. Or yeah, this project is very costly relative to our exit or very costly relative to the quarter we're in or how we're doing. Right? And so like, they can make those kind of quick passes on it versus like, hey, we have availability. Let's move into the top 10, right, and bring it into the fold.
• 30:15
  Speaker A: So that's just purely kind of like a numbers game there. So when we first met, I kind of explained to you we've done like hundreds of shows. I mean, we're nearing 400 real soon. And the one thing that I don't think anyone's going to disagree with, even if they do that subconsciously, they agree with it. And that's nothing gets done in any company without it touching it in some way, shape, form or fashion. And there's numerous people sitting in the C suite that have a seat at the executive roundtable in many, many companies. And that's nice, but how much nicer is it to actually be heard and kind of understood from an IT leadership standpoint? Why are so many people. And I think we've kind of already answered this. But why are so many people still having a seat at the executive roundtable but not necessarily being heard? And I guess what I want to ask you is what does it leadership actually really, really want from an emotional standpoint? And then how can we back it up with numbers or data? Which is kind of like the theme of this episode which we wanted to talk about, which is how do we bring data analytics to a cost center battle? Because what it has been accused of or been pigeonholed into for so long is that they are a cost center and a department, not a business force multiplier.
• 31:30
  Speaker B: Yep, yep. No, that's. I mean, that is the sort of label we've had, right? And it's still a battle the way you still fight today, right? To your point and the point of this podcast. And I think it's continuing that process of demonstrating the business understanding, right? And tying those things together becomes the enabler. I think there's better ways to be structured, Right. I think as much as I have had really good CFOs, I've reported into reporting, the CFO, I think is a challenge still today. Like, I think that becomes a. The person holds the money is the person that you report into, right? And so that becomes still part of the challenge. So I think getting to a place where you're truly like, when I think about the true partnership, like reporting to a CEO, like, that's in my mind really the only way to go directionally to go. And this doesn't always happen. And so I think sometimes when that's the case, you're already starting off like one hand tied behind your back, right? Because you're either reporting as someone who has different priorities, different initiatives that conflict with yours or direct conflict with yours, like finance, for example, there to kind of save money and control cost. And you're spending money, right? And so, and they're not the decision maker oftentimes on is that value worth the spend? It's someone else, right? But like, sometimes you can't get past that sort of hurdle. And so my experience really is again, bringing those things to the table such that like, to your point, like, without it, businesses cannot run, right?
• 32:51
  Speaker A: They just can't.
• 32:52
  Speaker B: There's no project out there that exists that doesn't have it or technology piece to it. And so demonstrating like, again, that's where this project management piece to me is always so critical because that intake process becomes like, it captures so much of that data to say, this is why we're doing this. And then I think their part, it diffuses a bit from an IT standpoint, which I think is an interesting one, an important one is it's not me suggesting we implement XYZ technology, it's the business making that decision. Right. And so I'm making a recommendation or supporting a recommendation from a sponsor within the business. But like I'm not necessarily driving that decision. Not say I don't do that sometimes but like use examples like Salesforce, right? Like Salesforce is great but I'm not going to ever say that's the right solution, that that needs to be the right solution based on the requirements and that comes from the business. Right. And so I've become more of the partner there to say I'm driving this forward in a way where we can support it from an integration and a data and a cybersecurity standpoint. But like the business is making that decision and it deflects some of that sort of blame game of like IT projects that don't go well or go sideways or technology maybe doesn't do. All that said, it's supposed to be doing like we deflect that from us to say like well hey, we didn't choose that. You guys chose it. We made recommendations, we outlined risks, we outlined concerns. The business still chose that we support that. Right. Because the business suggested we do that. But like at the end of the day it's not like come back to like blaming. That's the piece I think where it gets the bad rap is like then we get blamed for a failed project and it's like well it's generally not the technology, right? Like I tell people that all the time, like you need ERPs for example, like oh this ERP is terrible. Is it really though? It's probably not right. They all do the same thing to some degree. It's the change management, it's the adoption, it's true executive sponsorship like without those things, that's what products fail. It's not because the tech, the tech itself failed.
• 34:46
  Speaker A: It's kind of like a double edged sword. First of all, the CFO relationship, which is. And if it can, that's why I'm a big fan of kind of like this low hanging fruit for the cfo because a lot of people do report to the CFO or there's kind of this like a hybrid relationship and if it can come in and I don't know, just eliminate a lot of kind of low hanging fruit for the CFO and I don't know, make billing easy or put things in different billing like account codes that match Your company, not the vendor's company. You know what I mean? And making the vendor like change account codes to match things for your cfo, like that's just something that we've been really, really good at doing for other people. And I think it makes a big difference for the. Because now all of a sudden the CFO is like, oh, I love you, it. What else can you do for us? Oh, and well, we got some money here. We don't need to do everything Capex. We can do things opex. Oh, oh, but you do want Capex. Oh, so we do want to depreciate over five years. Okay, fine. So that's kind of like, like the side note piece there. And now. So the double edged sword is it always has to strategically bring the options to the table and be this kind of advisor. Kind of like this advisor thing is, I guess kind of what you're going at is like, okay, so we've got all the different departments at the table because IT sees every aspect of the business and you've sat in those meetings and you've learned what they need or you've learned how the the business needs, which a lot of people don't do. Which is probably why you have people take public speaking to begin with is they're not comfortable to go out and speak with people or they're not comfortable enough to ask the right questions when someone calls into the help desk or however it is now, you have a clear understanding of all the problems that everyone has and you've presented solutions and they've chosen. So it's like, hey, you guys chose it. So it, I think historically is very, very good at not taking the blame, just being kind of like this execution department. But that also happens to be the problem at the same time.
• 36:30
  Speaker B: So I think what the missing piece there to me is you're, you're exactly correct. The difference I think that we would need to change is that's oftentimes where the journey sort of ends, right? Like you've helped them choose the solution, right? Either you're gonna, either the IT teams are implemented or a partner's gonna implement. But like that's where the IT journey typically sometimes ends versus like continue to be a partner in that process. So like in that example, like what I see there is, and the most recent projects I've been involved in and, and I think this is two things here, but we'll start with the first one. You can't stop being the partner, right? Like that's where you need to continue to partner. With the business as they're making decisions and be a part of those meetings, because there's still further opportunity to execute and be a part of the solution as a part of, like, just accepting the solution. Right. So I think sometimes it kind of goes away or they're like, okay, well now we're heads down just doing this thing, and you can't be your head in the hole. Right? So I think that's part of it. The other part of it, I think in the world we're in today, which still I'm surprised, but maybe I shouldn't be. But, like, people still have this idea of, like, building things specifically for them, custom, whatever. In the cloud world we live in, that doesn't work. The whole idea of this shared platform means there's less opportunity for it. And what I see as a, as a big challenge is a big problem often is they still go down that path and then they wonder why kind of back to this tech. The tech is the problem. They get on a problem, they're like, well, hey, netsuite is running, like, really slow. Well, yeah, because you customize it and it's not built to be customized. It's built to. You adapt the best practices, then you're good.
• 38:08
  Speaker A: Keep going. I'm with you.
• 38:10
  Speaker B: Here's the thing. I think the question I always force people, and it's an uncomfortable question, is because people will always say, the one answer, which I'm going to share here in a second, is I always come in, I'm like, how are you really different? I mean, from a podcast standpoint, another podcast company, your content's different, obviously, but the way you approach it, is it really different? Are you really that unique versus your competition in that particular space? And then of course, the answer always in my world is yes. And I'm like, well, tell me, how do you bill things differently? Do you accept payment differently? Do you produce stuff differently? And the answer generally for all those questions is no. And I mean, well, then why do you have to have a different process? Why do you need a custom process or a custom solution for that piece? Now, again, there's always some nuances there, right? That's not always completely.
• 38:56
  Speaker A: So how does it help that company not do the same thing that everyone else is doing and actually kick buck and make more money, actually drive revenue?
• 39:02
  Speaker B: I know, and I think it's worth, like, again, like, I spent a lot of time and energy. Now this has happened on my last few jobs is I end up staying up like a team of calm emerging tech or innovation Right. Center of excellence. There's different names for it like that really start to focus on. We have these business problems we all know about. Let's go evaluate technologies and let's do some use cases, proof of concepts and figure out where there is opportunity really to drive that change in value creation and, and differentiate us from someone else. Like it's kind of back to this golden grail idea of like the estimating like where I'm at now, everyone knows it, but no one's really pursuing it. Because in our current business model that we're in, thankfully in some ways, like people just call us up and give us business. Like we're not even competing for business because there's so much of it now that's a unique scenario. But like because of it, it doesn't force us to like get better at some other things we should be getting better at anyway. Right. Like that would be a further differentiator.
• 39:55
  Speaker A: Right.
• 39:55
  Speaker B: So I think it's onus is on someone to kind of take that step and own that change. And that's where again, this IT piece, like that's how I can personally kind of change this business. Like if I can drive that piece of this business, it will differentiate us from other businesses. But it's not easy, right? Like business is doing well. People have been doing this business the way they've been doing it for years, have been successful. So like why should we change now, right? So like it's overcoming all this sort of like resistance Again, the change management piece of it, right, which is just now inherent in every technology project anyways, I just. How do we manage the change? How do we manage good adoption, things like that?
• 40:30
  Speaker A: Is there room for it to be more brave and take more responsibility and attach their name to actual numbers and stuff? Because it's kind of the opposite like that. How it's been is like, well look, you guys made the decision. I provided you all the different options, you made the decision. But is there more of an opportunity after they've done the Stokes five steps to legendary thing, is there more opportunity after you've looked at it all to say, hey, this is what I think and I think we should do this and I think this is going to drive these numbers and we're going to be able to eliminate this, this and this. It may not be perfect, there's going to be differences and be some change, but I'm willing to put my stamp of approval on that and say that we're going to gain X number of percentages. Do you think a lot of IT Leaders get stuck where they are because they are afraid to be business leaders.
• 41:22
  Speaker B: Yeah, absolutely. Right. I think people get stuck because they're stuck in that sort of. We're in run. Right? Run is it. So we're stuck in run. So we do a good job at run, and that's what people focus on. And. And like, again, my example is like, that's where I start. But to your exact question, like, that's not where I try to end. Right. Like, as soon as I can kind of stabilize the sort of top five things, if you will, I do quickly then move into, like, where is their opportunity. Like, so, like, as soon as we get data. Right. Like, man, the AI piece is going to be one I'm going to pursue heavy. Like, that's going to be an area. So I think it does require a different type of leader. Right. Like, it's. It's a leader who wants to. And that's why you see, like some of these businesses, like, they have a chief Digital Officer who is viewed as the build person and they have a CTO who's viewed as a run person. It's okay if that's the role you want to play. Like, that's not the role I want to play. Like, I'm definitely a builder. Like, right. Like, understand I need to stabilize, stabilize, stabilize, etc. Right. That's part of my job always. But like, at the end of the day, I don't want to be the running guy. I want to be the builder. Right. And so there is opportunity for it. But like, it does require a different mindset, a different type of IT leader than we've seen in the past. Because in the past we were just running, run, run, run.
• 42:28
  Speaker A: Right.
• 42:29
  Speaker B: That's all we were doing. Right.
• 42:30
  Speaker A: So it's just rare that I think people are pushed out of their comfort zones or even.
• 42:34
  Speaker B: Yeah, yeah, agreed. Totally agree.
• 42:36
  Speaker A: Because once they see and they're in it, it's like. And I've told many people this, living kind of in. That is why you end up with a lot of people that are going to be complaining about the future. Yeah, man.
• 42:45
  Speaker B: It does come back to like, challenging yourself. Right. I think. And again, it is a mindset piece. I'm not sure what the solution is. I think I was always a driven person. Right. Myself. Like, not only am I with my personal life, like, I finished my basement over Covid. Like, I'm just that type of person that goes and figures things out. And so I think that was more unique amongst us. And so I think it Goes back to a bit of the education and training and a lot of the mentoring, coaching. I think I've been very fortunate to have some more, especially on the tech side of the business, like in the past, like tech companies, really good leaders who helped mentor and coached me to like to push for change and the different spaces that we're in. And so I've taken those lessons, learned and moved on. And somebody had leaders that have not pushed for change and I've seen how they reviewed or got removed or exited because they didn't seem to help support the business properly. And so I think it's just understanding those lessons and it's. There's no easy, no silver lining, no easy solution to it. I think maybe the younger generations, I guess I'll put it that way and age myself a little bit, is I feel like they're more open to the idea of the change. Whereas as some of the older generations kind of exit out of the workforce, maybe we'll be less resistance there. I guess maybe it's a hope.
• 43:53
  Speaker A: Yeah. I think it just depends on are you the person that's in your midlife on cruise? Yeah. Are you in midlife on cruise, in your job role? And like, kind of like that's it. You're just going to be there and fade away. There'll always be a spot for you. Like, if this company goes under, changes, gets by it, just kind of move on to the next one. But to me, that's like, it's going to be an interesting problem. If a lot of things change over the next five years and you're on cruise in your midlife it. Is it going to be a midlife IT crisis? It's like a new thing. Where are you going to go? What are you going to do? Is it going to be. I think there's people that are afraid of, like, hey, what's going to happen? What's the job market like? And I guess my solution and the mission of the show is like, well, you might want to become a business leader real fast in technology, and you're probably the most poised to do that. I don't care what age you're at, and the older you are, you probably have more, you have more experience and you've seen more. So you've got to basically grow some and. Or just gain some courage and understand this business piece because you're probably in a position to understand it more than most people, in position to make a big difference.
• 45:05
  Speaker B: No, I totally agree. I think that's where, like, I fought that battle like from, from a job churn standpoint and private equity by its nature, some of that. But like I, I'm definitely one of those people who look at people who've been somewhere for 10, 15 years in it and I'm like wow. I mean have you hopefully you challenge yourself in those roles because if you haven't. Right. And I think that's where like historically our parents generation go work someplace, retire from that place. Like I think as again kind of back to that as people age out or to your point like don't force themselves to change, then you're going to be faced with that sort of retirement of things. Right. I mean but you're exactly right. Like people like myself and even older who have all that life learning experience around the business are totally positioned to like be that sort of business IT change agent for sure.
• 45:50
  Speaker A: Yeah. They just have to be willing to kind of I guess responsibility and stuff. But once you kind of like fight and push yourself out there and see some success and I think you get more used to doing that 18 months from now, what's everyone in it going to be talking about that people ignore today?
• 46:06
  Speaker B: Wow.
• 46:07
  Speaker A: I have my ideas. I mean I think after I ran into it and I saw it happen in front of my face, I was like oh, it's going to be this for sure.
• 46:14
  Speaker B: I think the thing with AI that was kind of curious. I think we'll see more of around that sort of ideas. We've obviously lived through all kinds of technology change but I feel like historically the tech change has been brought to the business from the tech leadership, AI. My opinion, especially the LLMs and ChatGPTs of the world was the first time in my career that was brought to me as an example when I was at my prior company race winning brands manufacturer. I didn't Even really address ChatGPT because I was like no one's using it. We're manufacturing, we're already way behind time synology wise. Lo and behold I find out sales, marketing, a bunch are using it and so I think we're going to see more of that where whatever the tech is, I don't know what it will be but like where it comes in and it comes in a way where like everyone's just using it all of a sudden and it's quickly become the norm versus historically it had never been the case. Right. Like any change that kind of got brought into a cloud. Right. Like when cloud happened, like we pushed that change, we the IT people did. The business didn't say oh let's Go into the cloud. If anything, they were getting afraid of
• 47:23
  Speaker A: people, that the cloud was like safe.
• 47:24
  Speaker B: Yeah, exactly. So safe, cost effective, scalable, all that kind of stuff. Right. AI is the one that's kind of forced turn the sort of envelope of like. No, we're bringing it to us again. You see that some in shadow it but like it's still topic with dev guys.
• 47:39
  Speaker A: It's happening with the DevOps guys because they're starting to see it because just like developers, they've been working on some project or they're going to build their own CRM or they're going to do something like this and there's not a CRM for like a podcast. What am I gonna do? Buy Salesforce and get some custom guy to like customize Salesforce for this? But Greg built like a CRM for us like in two days. And I was like, dude, are you kidding me? Like all. I mean just like with reporting, customer reports, login backend and then like our other friends that are in devs, we're like a lot of people are just kind of being. They're like in shock. I got a lot of dev guys are in shock. Like, no, this will never. They're either complaining about it and saying it's creating problems for them in their life, or they're like the way that we need to think about this is not how we've been thinking for so long. Such a different thing. It's taking something that took manual human coding and stuff like that. It's just really kind of like maybe six months ago, you're like, oh yeah, no way. There's all kinds of problems. There's like this and that. Not now, like literally as of two weeks ago. Two or three weeks ago, I would say even a month ago, it made an exponential jump.
• 48:50
  Speaker B: Yeah, no, and to your point, like those exponents for jumps will continue right? To like what will that evolve into? So I think that's where again, kind of back to like really being on the edge of technology. At least the understanding of it will be the differentiator of people from the standpoint of like who's successful and who's not versus the ones that kind of
• 49:08
  Speaker A: playing around with it.
• 49:09
  Speaker B: Yeah, yeah.
• 49:10
  Speaker A: It's kind of back to like the Facebooks of the world and stuff and the people that were playing around with technology when we were younger that just like were way ahead of the game. There's people doing that now. Yeah, like our producer Greg. I just like in forums all day just like finding different ways to do stuff. I would like light years ahead, like one of our CTOs or CIOs are going to go out and we're going to hire a dev team to help customize this ERP or rebuild our old legacy software. They're doing it the old fashioned way. And that I think is going to die. And I think they should not be doing that right now. It has been an absolute pleasure talking with you. I guess final question would be, what's the one thing that you would want the C suite to hear loud and clear that they're not hearing today about technology leadership? What do they need to know and hear loud and clear?
• 50:07
  Speaker B: I think it goes back to, we understand the business, right? Like, we want to solve business problems. I mean, any senior leader who is a senior leader at this point doesn't chase giant objects. Like, we're not. That's. Those days are done. That's what I want people to hear. Like, those days are done. Like, very infrequently do I meet someone across all my peer groups where they're like, still stuck in the old ages of like, building some new infrastructure out in Cisco. Like, that's not what we talk about. We talk about solving business problems and sometimes we'll talk about technology, but we've talked about solving business problems. And so I think that's where just got to break that mold. And we obviously continue to do that. But, like, I'm always still surprised kind of how slow that process has been and taken. And still we still fight that battle every day in terms of, hey, we're just there with you guys. Like, you understand finance, you understand operations, you understand hr. We understand the business too. Like, right. We should be there with you guys solving the business problems.
• 51:00
  Speaker A: Thank you so much for being on. You've been heard. So, Mr. Stokes, you've been heard.
• 51:05
  Speaker B: Thanks, sir. Appreciate it.
• 51:07
  Speaker A: Take care. Of.