Why 70% of Digital Transformations Still Fail (And How AI Can Help)

Galen Low: Long before AI was making headlines, digital transformation initiatives were helping businesses take big leaps forward and giving them a competitive edge. It's gotten to the point where digital transformation is right up there with the word synergy on most consulting buzzword bingo cards. So why is it the case that even to this day, 65% to 70% of all digital transformation initiatives fail?

And why are we okay with that? Shouldn't we have gotten better at it over the past three decades? Is there no solution, or is it maybe better business just not to solve it? And also, can't AI help? To answer those questions, I've brought in a 25-year veteran of the tech consulting world who has worked with the biggest management consulting agencies to deliver enterprise level digital transformation initiatives for Fortune 2000 companies and up.

We're gonna explore some of the key reasons digital transformations still fail, whether AI can fix it, and what the role of the human is in all of this. Hope you enjoy the episode.

Welcome to the Digital Project Manager Podcast—the show that helps delivery leaders work smarter, deliver smoother, and lead their teams with confidence in the age of AI. I'm Galen, and every week we dive into real-world strategies, emerging trends, proven frameworks, and the occasional war story from the project front lines. Whether you're steering massive transformation projects, wrangling AI workflows, or just trying to keep the chaos under control, you're in the right place. Let's get into it.

Okay, today we are unpacking the reasons why so many enterprise digital transformations still seem to fail, how AI is rewriting the playbook for implementing platforms like SAP S/4HANA or Salesforce, and what those two things together mean for both the project managers leading these initiatives and the big consulting firms that have traditionally dominated the enterprise digital transformation space.

With me today is Rick Catalano, founder and CEO of AMIGO, an AI-powered platform that acts as a digital transformation guide and author of the new book, "The AI Project Manager". Rick has spent over 25 years working side by side with some of the most recognizable management consulting firms, including Accenture, Ernst & Young, PwC, and Capgemini, where he led large-scale digital transformations for Fortune 2000 companies.

After seeing firsthand the repeated patterns of huge cost overruns, massive delays, systemic inefficiency, and frustrated stakeholders, Rick created AMIGO as a solution to help project leaders avoid the mistakes that sink most transformation initiatives. And now with his new book out, he's on track to prove that artificial intelligence isn't here to replace project leaders, it's here to make them unstoppable.

Rick, thanks for joining me here today.

Rick Catalano: Absolute pleasure, Galen. Thank you for inviting me. Looking forward to our conversation.

Galen Low: I am too. You know, this is like-- I didn't spend a huge amount of time working at a big consultancy, but some of the things that you talk about in your post and some of the things that we've talked about are things that I saw every day in terms of, wow, this should be going better, but for some reason it's, you know, it's very complex politically or even just down to communication or even, you know, just how teams organize.

And I know it's a big lift for project managers or whoever is leading delivery of those initiatives, but I like the angle that you're taking with your work. It's a AI-powered but also human-led approach to, gosh, this should be better .

Rick Catalano: Yeah. It really should. I mean, there's, You would think at this stage, you know, I've been at this twenty-five, thirty years, I jokingly talk about it's you know, technology, you know, the, the, the biggest changes when it comes to the program management is, you know, when I was a kid, you know, coming up, we did everything on a file server with Excel, PowerPoint, Word documents, and Microsoft Project.

Twenty-five years later, how are we running our projects? Excel, Microsoft, Word, emails, but we've gone to SharePoint or we've-- now we have- ... Smartsheets. Now we have ten different SharePoint portals, and the same challenges exist. It's like we're generating massive amounts of documents, but no one can thread them all together, and what's your source of truth?

So that's just been a fundamental challenge. Since the day I started consulting, and here I am, I think I've got the golden ticket to solving that problem. At least that's my thesis. And even with the project work I'm doing today, it's the same challenges that existed when I was a, a fresher, you know, and one of the big guys, so.

Galen Low: It's really funny you mentioned that, right?

Because you're right, there hasn't been that much change in the way that we operate and do these things, and digital transformation initiatives, I know it's a buzzwordy thing now, but yeah, they've always been difficult, but like right now we're at this like inflection point where there's gonna be a lot more of these digital transformation initiatives, and it's not just for fun anymore, it's actually like for survival, so.

Rick Catalano: And here's the thing, you know, like I said, 'cause we talked about data, okay? And like I said, then I talk about in the book, "Yeah, we got all this great data, and AI can take all these spreadsheets and come up with all this kind of information." But guess what? The data's wrong. It's like all your AI's gonna do is get you to a faster wrong solution at scale.

Because it's not connected. That's the root cause of, you know, the stuff. Again, we'll talk about all these things, but again, my thesis, the root cause of the challenges in what I do for a living is the disconnection. When you have a team of, you know, 200 to 1,000 people around the world, it's like, how do you keep everyone connected?

And I, I think we've developed a secret sauce to try to solve that.

Galen Low: Well, let's dive into that actually, because I wanna ask you just a spicy question to start us off, something that, you know, my listeners really want your take on. And as you mentioned, you're someone who's spent over 25 years working side by side with firms like Accenture, EY, PWC, Capgemini.

You're doing these large digital transformations, and then you've gone on to build an AI-powered product management tool that bottles that experience into like a tool really that helps leaders for any of these digital transformation initiatives and to support the success where so many others have failed.

So I guess my big question is this: Is AI going to make the big consulting firms irrelevant when it comes to ERP implementations and enterprise-level digital transformations?

Rick Catalano: No. I don't think so. I mean, I think, you know, first and foremost, like I came from the tier ones. You know, I like to say, you know, I was in the, the New York Yankees system.

I was in the, the, you know, if you think about the elite of the elite. And I was blessed growing up in an era where, man, you learned a lot. You learn how to be a professional consultant I was blessed, and I'm blessed to work with those guys still. Where AI, again, my opinion, it's going to help clients reduce the cost of the projects, I think, a little bit because I think the way that, you know, the majors are structured are they have this bottom, you know, base of consultants who do a lot of the, quote-unquote, "administrative grunt work," where I think AI is going to take some of that work away.

And like I was talking about with these thousands of documents, in today's world, how does that happen? Well, you get a bunch of freshers or, you know, relatively new consultants pulling, "Hey, can I get this document? Can I get this document? Can I get this document?" They're pulling all these documents together and then taking them and then building PowerPoint slides for the status reports, and then they give them to their bosses, and their bosses say, "Well, I don't like the colors coming out of this, so I'm gonna go and put my perception on it."

So when you get to the executive meeting or the status meeting, everything is green. I jokingly go, "I see everything green." Yeah, 'cause, you know, yeah, I'm not saying that everyone's cheap, but the human perception, you know, as you're getting up to this, I mean, of course, I mean, you're human. It's like you want to put out a good face.

So yeah, does the narrative get skewed a little bit maybe in the PowerPoint presentation? At least in my experience when I went as an advisor watching them, yeah. So where I'm going with this is The data, when you do that, again, what's the source of truth? Is it right? And even if it was right, you know, nine times out of 10, it's seven days old.

So, you know, it's like, because by the time you do all the collections, it's irrelevant and, you know, w- life moves on. So the work that is happening at that level to do all that collection, that I think is going to go away. However, with AI and with the, you know, you know, bridging the connection gap, I think the margins, you know, the dollar volume might go down, the margins are gonna be better because now you have really high-end talent that you could, you can do it at, you know, higher rates, but you're gonna lose a little bit on the base.

At least that's my opinion on how this thing's going. And then, you know, y- which is possibly gonna hurt, you know, a little bit on the bottom line with the big guys. I think it's gonna help the smaller guys a little bit and make the competitive playing field a little bit more closer where I think you know, clients might have more choices.

But, you know, the, as the saying goes, and I don't see this changing, no one's ever gotten fired for hiring Accenture. Right, right. You know, they have a brand, you know, and all those guys have brands of respectability and liability, you know, which is, is something you gotta take into consideration that yeah, will not go away during this transition.

Galen Low: I think honestly, that's a really good point and a really good way of looking at it. Not like there's gonna be this big shift in the market, like these consultants exist for a reason, and the thing that you mentioned early on there is like, you know, you were trained in the school of hard knocks to become a consultant, and that is an art form in and of itself.

That thing you said where, yeah, maybe it's analysts or freshers bringing stuff to you, but it's that judgment and instinct, the freshness of the information and what you do with that data that actually decides an outcome in some way, shape, or form. Not necessarily "Oh, that's okay, just give everyone like an LLM and they're gonna be like a consultant."

I think that misses the point. But I do like that idea that the margins are shifting and the marketplace changes a little bit where, you know, a smaller consultancy that maybe isn't one of the big four can still play at a higher level of the game without having to have a whole bunch of analysts on staff.

Rick Catalano: I think so. Let's just talk about it. Again, like I was talking about, when I grew up, they invested in you, and I'm not saying they don't invest in their account, you know. So you were carried through good times and bad, all right, back in the day. In today's market, it's so lean that, you know, it's like the benches are infinitesimal compared to, you know- So now, you know, kind of like, you know, a General Motors, you become a vehicle brand owner.

So you own the brand. Again, you got your X percent of really sharp who are full-blown in it to win it, but then you're, you're-- they're hiring and they're subcontracting white labeling consultants who don't know their, how they operate, you know? So it's like that part of the market shift where I get excited as a smaller guy, the little guy, it's you know, I have access to the same talent they have 'cause...

And it's former accelerators, former EY. I mean, I only hire former Bigs, but then I put them in a model that gets them to understand the brand and gives them all the accelerators, so they are acting like AMIGO day one. And that's, you know, part of the power of what we built into the AMIGO platform, but then as part of the consulting services we provide as well.

Galen Low: I actually love that so much, and I won't go too far on a tangent on this, but, you know, there's this notion where there's so many layoffs happening and so much downsizing and so much reorging, and you're like, wow, there's just not enough jobs in the world for all these people.

But what I like is that your staffing model is like, okay, yeah, sure you know, you still want the cream of the crop, but some of this talent is available to you, and you have infrastructure for your business where you can be competitive in the space. You know, A, these people who may have been downsized out of a job now have jobs, and B, your business is something where you can, you know, carve out your niche of the market and not just always get squashed by the big four.

So I really like that.

Rick Catalano: The analogy I like to use for my business model is, you know, I'm originally from Chicago. I live in Arkansas now, but I'm a Chicagoan. All right. So huge Bears fan from the '80s, huge Bulls fan from the '90s, you know. And when you look at the Bears, you know, again, sorry if I'm going off, way off tangent here, but-

Galen Low: No, you're good. You're good.

Rick Catalano: '80s, they had the Forty-Six Zone, which was, you know... And basically it made Hall of Famers. But it wasn't that they had all the great talent, it was the system in which they worked in. Then you had the '90s, you had Jordan, who was trying to curate a team of his own. Guess what? They bring in the triangle offense, and now the system makes them champions, okay?

That's the same model that I'm trying to put in is get great talent, put them in a system, position them for success, and they're gonna deliver. They're gonna accelerate delivery, working as a team quicker, faster, better, stronger, and getting that time to value to their customers as quick as possible.

Galen Low: I really love that perspective, and I like sports analogies even though I'm not a sports person, because I think it really articulates the importance of team, right? We tend to make celebrities or, you know, we, you know, canonize these individuals or in filmmaking, right, like cult of director, it's oh yeah, the director did it all.

You're like, not really. They were in a system that allowed that talent to manifest. So I like that. I wonder if we can zoom out a little bit because on your LinkedIn profile you state outright and you're like, "Seventy percent of digital transformations fail." And yes, I know that you're probably leading the other thirty percent, right, helping them succeed, but that always piques my interest and it's just it's one of those things that, I don't know, you know how there's just these stats sometimes where people just kind of like, they say them, they're shocking, but we don't do anything about them.

Rick Catalano: Let me anchor that for you just a little bit. Yeah, okay. So how did I come to this? It's actually the, the... Again, depending on who- which, you know, thing you're looking at, yeah, sixty-five to seventy percent. That came, you know, the sixty-five percent came from a study done by Oxford and McKinsey. I think it was two thousand twelve.

Okay? So it's dated. And that's where I, you know, started building my talking points around that study. But it's like, well, Rick, it's twenty twenty-six now, and we've had all of these digital transformation things, and we got Agile now, and we got AI now. Of course, the numbers have to get better.

Well, believe it or not, Dr. Ben Feenberg, I had to go, you know, it's a little hard to say. He's a professor at Oxford, and he's a professor at University of Stockholm, and he took that study that-- done in two thousand twelve and redid it Tripling the size of the pool, and guess what? The numbers went up.

It came up to you know, in certain markets, 91%, and the billions and billions of dollars, and 400-447%, if I remember right. Again, don't quote me. You read the book, it's fascinating stuff, and I, I, I'm gonna start, like, taking his book. Brent and I, we're on LinkedIn together, and I'm looking forward to doing some work with him in the future because everything he talks about, I think I...

You know, we've worked really hard to try to solve those problems, you know, through our thesis on, you know, bridging the gaps of all those disconnections. So, yeah, it's-- But it's just the numbers are even higher than they were, you know, back in 2012. So, that, I found that fascinating.

Galen Low: Well, I mean, talk to me about that because, you know, some of the reasons, I guess the big question is why do enterprise digital transformation initiatives fail in the first place?

And, like, why is it getting worse, and why are we okay with that?

Rick Catalano: Yeah. So again, my thesis, my opinion, where we run, there's probably 100 different dimensions. If you're talking to an, a Harvard organizational change management person, they're gonna say, "It's all because of change management." Or if you talk to the, you know, professor of computer science, "It's all about the techno-" Yeah, it's like everyone's gonna have their lens.

My lens is it's all about the disconnection. So like we've been talking about. You got thousands of documents, you got hundreds of peop- So there's actually... You know, you remember back in college, there was this formula that we learned in communications class, and I can... N times N minus one, you know- divided by N, something like that. You know, so if you take 200 people on a, on a project, all right? And each person is changing one thing a day or listen, you know, that's 20-- 19,000 or 20,000 different communication channels- Right ... that are potentially exposed on those changes. Who the heck can do that?

And who knows who to give what information to? And that's part of the disconnect, where decisions are being made on one side of the world that people are finding out about six months later that have major, major repercussions that are then costing millions of dollars. And so, you know, what we've done in AMIGO, it's like I said, because we have everything integrated in one model, is we built the AI to let people surgically know what changes are gonna potentially impact them, who moved my cheese, and give them an opportunity to at least react.

Galen Low: Right.

Rick Catalano: Trying to reduce those gotchas to help, and then therefore accelerating the delivery of the project.

Galen Low: I like that. I wonder if we could dive into example, because I love that idea of the disconnect and the complexity of communication and collaboration and, you know, the other points are true as well, right?

Change management is hard. Technology is hard. Guess what? All of this transformations, all of those things rolled together, lots of people, lots of complexity, lots of things that can go wrong, lots of potential for expensive mistakes, and maybe lots of potential for a solution there that solves the disconnect piece.

I wonder if maybe I could just put you on the spot because, you know, you have a couple of decades under your belt doing this. In the green room, we were talking about, yeah, you don't get this far without getting some lumps, without getting some warts, right? Without having the battle scars. I wonder if you could tell us what the most expensive mistake you've seen on a transformation- Yeah.

Yeah ... whether it was yours or somebody else's, and maybe we could talk through, like, how it could have been prevented.

Rick Catalano: Right. So great question. I don't know if it's the most expensive, but it's the most memorable mistake, expensive mistake.

Galen Low: Okay. Okay.

Rick Catalano: And honestly, it's what got me thinking about AMIGO. So, you know how in Back to the Future, Doc Brown fell off the ladder, and it's like, "And then I saw the flux capacitor"?

That's right. Error was my, "And then I saw AMIGO." Honest to goodness, you guys are my witness. So let me explain the story. So this is, again, going back quite a while ago, in the semi-early days of Facebook. So you think about that era, you know, and I was a mid-level a- adopter. I mean, I wasn't an early adopter, so you know, I have...

You know, hadn't seen high school buddies in 20-plus, 25 years, and I, all of a sudden, I got this great platform. It's like, wow, I can see their children. I get, hear all the stories and all the great things that are going on. I get to talk about how their careers are. While this is all happening in that era, you know, I'm working on a, a project.

It was a top project. You know, a Fortune, Fortune 1000. Yeah, I think they were, they, they were pretty good size. I was helping on the cut-over and data migration stuff, and everyone was in... You know, this is in the, back in the day when everyone actually flew into a building and y'all worked in the same building, okay?

So we are in dress rehearsal. Maybe it was a SIT2 or UAT, somewhere in that timeframe. So the data migration team and these, you know, guys are just guts out 18 hours a day, getting all the changes from all the data migration changes to get the data migration right. And we had a pretty good run in our UAT or integration two run, so we were really comfortable with that.

While at the same time, 200 feet away, the process functional team is working with the testers and the, the user acceptance testers, and they're making all these changes to their stuff based on the defects that are going on. Mind you, so we got the data migration team, smart people working their butts off.

You got the functional team, smart people working their butts off 200 feet away, not really letting each other know what's going on. Go to do dress rehearsal, kaboom. And you go You're just in this... Yeah, I remember it like it was yesterday. What the heck, you know? What, what just, you know, c- come to find out kind of these things that, that took place.

The impact, and again, this is going back, you know, in dollars from about 15 years ago, 10, 15 years ago. That was a 10... You know, we had to delay the project a whole quarter, you know, because now you lost your entire implementation window. This was not a huge project or you know, but it was a $10 million hit, which was a significant percentage of the budget on this mistake.

But that was the how in the world can I know how my friend Tammy, who I haven't seen in 25 years, how her kids are doing, yet 200 feet away I don't know what the hell's going on? And that was the I got to... This was, that, that was my moment. It's like, how do I fix this problem so this never happens again?

And that was the impetus of where AMIGO came from.

Galen Low: I really like that. I like, you know, that the problem is solvable because you're seeing it in your social life but you're not seeing it at work.

Rick Catalano: Software can build something that can communicate with me. Oh, I can do that, you know?

Galen Low: Well, I, you know, and now what a great time to be alive where, you know, you don't have to necessarily, you know, have the team that built Facebook.

In some cases you just need the idea.

Rick Catalano: Yeah, absolutely. So it's, Yeah, so that's where it came from. That was a pretty big painful experience. And like we talked about, just the, you know, watching the overhead burn, I think it's gosh, we can really... I, I remember going into a client room and, and looking at their program management office.

Again, this is when we all co-located still. I walk in there, and there's like 60 people in the program management office managing this thing, and I'm like, whew, $200 an hour, $200 an hour, $200 an hour. And I, am I just adding up the math? Well, like you get a meeting with 100 people on it, it's like, this meeting just cost me, you know, $175,000. So it's like-

Galen Low: Right.

Rick Catalano: How do I avoid meetings that are not productive and provide the data to help make the decisions and target the actual people I need to get things done? And that's a, again, another thing I think we've got a pretty good mousetrap to try to solve. Yeah.

Galen Low: I wanna get into that because I wanna talk a bit about AMIGO and how it works and, you know, how AI is solving the problem, but I love that perspective on like burn rate or run rate, right?

Where of course these things fail easily because when you lose a day, right, it's you know, making a Hollywood film. You lose a day of shooting, there's, you know, hundreds of thousands of dollars right there. People just sitting because they can't do anything, still getting paid, you know, maybe still billing out, and no progress being made.

And it's just that's why, right? Because it's a fast-moving train. Talk to me about AMIGO, maybe even specifically through this lens, and talk about how this is now a solvable problem, right? We've got this notion of disconnect, a very fast burn rate, high complexity, and what does AMIGO do to solve that?

How does AI play into that?

Rick Catalano: Yeah. Okay. So again, I'll go back to, like I said before, you know, the era in which I came up with it. That was before I knew what a cloud was. You know, again, I know Facebook is probably built on cloud, but it's like it wasn't a very popular everyone was doing this cloud thing, so...

And AI was not even in the topic of conversation, you know, back in the thing when I first came up with it. My idea was, and again, this is the vision I had for AMIGO was build the bones, build the structure so that all the data was there, and then get a bunch of smart semi-retired folks who had been around the block a few times and just have them monitor all the projects across.

And basically it'd be they're consulting in the cloud was my concept, okay? And where I got that, the notion around getting these, these guys is 'cause one of the guys, I could call him a mentor, but he, you know, he was just a brilliant guy who would come in and it's you know, I'm in the trenches day to day seeing all the problems, but he was their, the external advisor that my client had hired to hold- Yeah, the, the big guy accountable, so to speak, you know?

Galen Low: Okay, yeah.

Rick Catalano: I was, I was the day-to-day holding the big guy accountable. He was the executive holding the guy account- accountable. And so he would come in every couple months or so and say, "Rick, give me this data." And you know, I, I was pretty buttoned up, so I was able to give him real spreadsheets and all that kind of stuff, was pretty close to decent sources of truth.

And he would come in and just say, "This is wrong. This is, this is where you're gonna get burnt," blah, blah, blah, all that kind of stuff, and, and lay it out. It's like, well, that's basically what I've been telling you. But for him to come in, you know, with just, "Give me... I don't need to interview anyone, I don't need to, you know, to do that kind of traditional QA.

Just give me the data, and I'll tell you what's going on," that's where I got the consultant in the cloud idea. So now you think, I was like, now all of a sudden this AI comes on, I'm like, "Hmm I don't even have to buy the gray-haired talent anymore. You know, it's just like you still need the judgment. Again, we'll get into that where the human aspect is.

But jokingly speaking, all that number crunching and statistical stuff I can have in my AI. It's called Belden, in homage to this gentleman whose last name happened to be Belden. And I liked Belden only because it's, you know, him, but I always thought of Belden as like a cool butler name, a person of service.

And I, and it's like, "This is Belden. He's serving you, and he's gonna be your servant to get you the information that, that you want." So that's how we got the name Belden for our AI. So that's basically... You know, and again, I'm not overselling Belden yet, because it's still in development. On Belden, you know, all the other bones and stuff like that in AMIGO are built, and now it's getting the, the data so Belden can learn is what we're working on now.

So we're hoping Q1 '27 it be able to announce to the world the magic of Belden. But that's a fun journey. I mean, you know, talk about learning a lot about the guts of what goes on, and it's like I, I'm not very technical anymore. Never really was that technical. That's why I went into project management.

But again, it's like, you know, you're a better leader than you are the, the tactician. So, that, that was my thing. But that you know, listening to my team go through the amazing what you gotta do to make this thing work, it's absolutely amazing to watch them work. So and again, not to pimp the book, but in the book I, I talk about, you know, what it's, it's the AMIGA framework, okay?

And it's all the principles one would need to successfully implement big scale, big, hairy, audacious goal-driven enterprise transformations, all right? And, you know, people have, for, for 20, 30 years have talked about it's people, process and technology. Well, it's a little bit more than that. It's people, process, technology, data, governance and value.

And those are the components that most things, you know, they get sometimes pushed to the wayside, though data's becoming a little bit more prominent in today's world. But it was the, you know, the red-headed stepchild back in the day. But now data's becoming a, a real big deal. Now, those are the things that need to get integrated through a governance model, you know, and that's where your traditional PMI kind of stuff comes into play.

And I'm a, you know, I'm a PI, PMP, RMP, you know, all the TLAs that come along with the, it, PMI. So you're doing that, and you're getting- You know, I try to follow those standards and, and their methods, 'cause, you know, they're good and they're proven and they're global, so why reinvent the wheel? So you got all the, you know, those six core things.

Then you have what does it take to run a big scale transformation? That's where the methodology comes in. So now you gotta pour in the methodology. Then you have, okay, well, I gotta deal with people, so there's all the organizational change management and everything that goes into that. I got communications that go on within you know, the stakeholder groups.

I got communications within the work streams of the people who are actually doing the implementation. So you got all these different audiences. You got the business processes, where you're taking those 50,000-foot level one business process, decomposing them down to the systems transactions, and everything that goes on with that.

You got all the data migrations that we were just talking about, where you gotta do all the source to target mapping. You gotta know what your systems are. You gotta know all the data dictionaries. And then you gotta use that same kind of mentality of, okay, I gotta take this apple and convert it into an orange through some kind of transformation logic, and building all that stuff, not only for your data migrations, but for your interfaces.

Then so you start thinking about just how complex all that stuff, and no one's talking to one another. Right. Again, it goes back to how, how are we storing this information? Well, on all my different spreadsheets and through my email chains and all that kind of stuff. So if you think about that whole flywheel, and again, that I talk about with the AMIGO framework, putting it into a kind of a core, very simplified thing of, you know, identify a vision, find the value, i.e.

the portfolio management and finding out what your strategic transformation's gonna be. And that's typically where PPMs solutions or even say from a, and I hate to, I'm not bashing consultants- Yeah ... you give the pretty PowerPoint that says, "Here's how much money you're gonna make." Right.

Yep. That's usually where it stops, and it gets put in the circular basket. We take it all the way through. So then now we actually go and implement using your, you know, whatever technology you want to be, 'cause it's technology agnostic. But now we, we actually build into the software solution the KPIs to get the value.

And then in AMIGO, we're actually monitoring the value that's received for up to 10 years after the implementation.

Galen Low: Oh, okay.

Rick Catalano: So you can actually see what you got delivered, okay? So it's, And then we can go longer than 10, but you know, we chose 10 as the... Typically, it's like what's my return on investment, my net payback, all those kind of financials, they want to see that.

But now we have a 10-year calendar to prove that. So all those things, everything I'm talking about, plus testing, you know, the whole testing thing, doing cutovers, you name it. A- and it's everything you need in every system, and usually about 10 systems that are needed, we put everything into AMIGO. You know, this is based on 30 years of battle scars.

Everything's integrated. So, and that's the beauty with the AI now, because one of the challenges, as I mentioned earlier, AI can crunch gazillion data points, but if they're wrong, you know, which is my source of truth, it's all you're doing is accelerating bad recommendations at a faster pace. With AMIGO, the data is already governed.

It's all in a relational database that has all the data. So your probability of accuracy goes up Phenomenal. And where that whole thing notion about, you know, taking four days to go build the status report that's already outdated by the time you get it, all that goes away because everything's real time.

As soon as you enter something in the keyboard, boom, it's registered in the dashboard. So that's the cool thing I think we, you know, we're really excited. You can tell. I'm proud of my baby, Project. So yeah.

Galen Low: No, I mean, I like that layering in of like governance, data, and value. You know, there's a lot of conversation happening right now about, oh, project managers need to deliver outcomes, and, you know, these frameworks are more about realizing that value.

And a lot of folks are kind of like, "Well, but how?" You know? I am just this individual leading something very complex. And I think what you said earlier about, you know, the communication complexity formula, I'm calling it that, I'm sure it has a name, but I'm picturing this sort of web, and then I'm picturing, you know, what you had said earlier about oh, 60 program managers in a room like trying to, even within those 60 people, stay coordinated, and then the hundreds of people beneath them that are trying to, you know, keep coordinated.

It's just too much for an individual. Meanwhile, you do have this processing power now with AI, your consultant in the cloud, you know, of things to look for and things to look out for. I'm wondering, like could you step me through like what life looks like then using the AMIGO framework, using AMIGO, maybe even in that same context of, you know, these two teams that are getting ready for a dress rehearsal or, you know, doing UAT and doing patch fixing.

How does AMIGO change how that process looks and how does it avoid some of the pitfalls?

Rick Catalano: Well, then now we're getting into some specifics. Yeah, and you mentioned UAT 'cause I happen to be going through one of those right now, so it's those ones are a little, little, little-- they're there right now.

So, you know- Yeah, okay ... they're not using AMIGO, so this is-- it's but let me take a step back on that. As a program manager or a program leader, and again, where I'm going is a change in that is gonna be the enterprise transformation architect. You know, you're not just a program manager or project manager, you're not just a leader, you're part of that transformation team, you know, and that's where that value component, Galen, that you were talking about all the time comes into play.

'Cause it's, you know, it used to be the, the three-legged stool, it's a four-legged stool now. And, you know, but you pull one away, it could still fall. So that's where I think, you know, just having that real time data and just with, you know, the years of experience gets you to a better decision faster. And I'll give some examples.

How far should I go on this example? I'm not gonna use, like just-- 'cause this happens on, again, every project. This one's only magnified 'cause of the sheer size of this. But this scenario that I'm gonna paint a picture on is common in every project that probably uses Microsoft Project today In cutover, cutover plans are pretty big, and you need them to run, you know, to get to UAT, you gotta get the environment set up.

And these plans, I've seen them as small as 1,000 lines. I've seen them as large as 25,000 lines, you know, single plan, okay? There's a lot of change, so... And, you know, with Microsoft Projects, you know, again, and that server base never really took off, but, you know, you have one person, you know, can only be in that plan at one time.

So it has the master plan. So you're basically going through a change request kind of doohickey to go update the master plan. Now That is as painful as can be, you know? It's the night switch just thinking about it. What we've done to try to circumvent that is, you know, we built into... 'Cause we have our, basically our own Microsoft Project tool, Microsoft Project-like tool in AMIGO.

You know, we can go and, and do those change requests and queue them up to get approval, and then upon approval, it automatically is just gonna put it right into the plan. So you don't have to double key the stuff, and it's gonna have the audit trail on it that says, "This guy approved this, and here's what it is.

Here's, here's everything that took changes." So th- that's an accelerator, you know, with the AI technology that we're using to do stuff like that. So, hopefully I answered your question.

Galen Low: Yeah, no, and I think that it hits home because, you know, even what we were talking about earlier, this notion that having no lag in the data.

As you get lag in the data, then your decision-making gets that much blurrier, and how many times have we been like, "Oh, it would've been great to know that two days ago before we wa- you know, someone went into Microsoft Project and changed 250,000 lines of, of the plan"?

Rick Catalano: Yeah, so the way we're designing Belden, and again, it's, you know, we're still in the workshop.

You know, Belden is saying is, if I'm the CEO, you know, how is my return on investment going on this portfolio? 'Cause you're looking at portfolios. So there's answers for the CEO, there's answers for the CXOs, there's answers for the program leaders underneath them, you know, based on wherever you... You know, that's the other cool thing with the AMIGO, it's it literally, it connects the CEO down to your first year I'm fixing bugs, or I am running a test script, and within six, seven steps they're connected.

And again, it's that whole Facebook concept that we were talking about. It's like we're all connected, the six degrees of Kevin Bacon, you know, kind of thing. But because it's all built into AMIGO, all the connections are there. So we're building these agents to, first of all, they're, you know, ask me anything and I'll give you the answer.

Right. But also we'll have agents saying, sending a nice little morning email to the CEO or the CAO, "Hey, by the way, my prediction is you're gonna go off the rails in six months based on this kind of information," and give them the highlights for them to consume. So those are the kinds of things that we're putting in there.

Galen Low: I like that picture of just you know, data being the social network of delivering an initiative that involves a lot of change . That's actually... It really puts that collaboration complexity into perspective, and I think it solves it. And you know, I think it also makes your approach really human-centric, I would say, because there's a lot of folks trying to build replacements of humans right now, and that's not what you're saying.

Even when it was a bunch of semi-retired consultants in the cloud, right? Even that was human-centric because it's about judgment.

Rick Catalano: I hated the word downsizing. And all through my career, I did not want people to lose their jobs in the work that I was doing. I wanted them to get retooled to become better citizens for their companies and better value drivers for their organizations.

And That's still the same mind- You know, that's, I have it, that's just kind, in my DNA. That's the concept that even it's like, I don't want to replace. I want to reprogram you to elevate your game to add more value than just, you know, checking off boxes on a spreadsheet kind of thing. So yeah, that's what we're trying to do.

Galen Low: So, let me ask you this. You spend a lot less time updating 250,000 lines in Microsoft Project. You have this free time now, what do you do? What does that person do to level up?

Rick Catalano: I don't know about you, but,

Galen Low: that's a feature I can get on side with.

Rick Catalano: Yeah, in all seriousness, no, it, it really is instead of just a doing the administrative bureaucracy, it gives you time to think.

It gives you time to, how can I make this better? How can we get it done faster and make better decisions quicker? And a- again, looking at it from the lens of the consultant. So I just... You know, your plate's still gonna get filled up. Yeah. It's not like you can go to the four days a week. I don't see that happening anytime soon.

It's just gonna make you more valuable, and as a consultant, higher paid-

Galen Low: Yeah.

Rick Catalano: Resource because of the additional value that you're bringing to your clients.

Galen Low: Right. And y- you know, even coming back to the top, it was never about, you know, your skill at copying and pasting data accurately. You know, the whole consulting model is around judgment and instinct and experience to know what to do in a certain situation, and then layered on top of the thing you said earlier was just so relatable, right?

It's when we have to do all of these things, it becomes so overwhelming that we just we're like, "Okay, well, we have to do something. We don't have all the data, but we have to move forward." And that's this panicky hysteria that kind of drives the role versus, okay, listen, we've got some time to think.

Let's be intentional. Let's be strategic. Let's not just, you know, put out fires, you know? And then that is valuable.

Rick Catalano: You hit the nail on the head, and like I said, I hate being a firefighter.

Galen Low: Yes.

Rick Catalano: I want to be a fire preventer.

Galen Low: Yes.

Rick Catalano: And that's my credo. And again, you know, done a lot of cutovers in my life.

My goal is to make cutover, which are very hard- ... boring. I just want it to be boring, and if I, if they're boring, I have done my job successfully. And, you know, that's, Or even, and just take it up to the level, if we are, again, I'm dating myself in terms of the seven keys to success that I learned in my PricewaterhouseCoopers days.

Yeah, it's like the, yeah, how your people are feeling. You know, it's kind, again, I wish I remembered them off the top of my head, but it's a lot of the metrics around the human side. If you're team burnt out because they can't keep up with everything you've been talking about because of all the administrative crap we gotta do in today's world, and can we work a regular 9:00 to 5:00 or, you know, instead of 14 hours a day, we can actually maybe we'll work eight or nine hours a day and have a, a balanced lifestyle and have a calmness instead of having to react to everything.

I mean, that's the nirvana that I'm, I'm shooting for that, you know, that I'm hoping my contribution or our contribution to this passion area that we both have can have an impact in that way.

Galen Low: It's so funny 'cause this half of my brain is like, does not compute. 9:00 to 5:00 and cutovers that are boring? No, that's never happened before ever.

Rick Catalano: That's where I'm trying to get to. Yeah, that's my, that's my goal. But where I like to... Again, I'm not there yet, yeah, but it's a work in progress.

Galen Low: I love that. I wonder if we can use that to segue into the book. You have a new book coming out. It's called The AI Project Manager. We've been talking about project managers, but we've also been talking about program managers.

We've been talking about transformation architects. We've been talking about consultants. For the book, who did you write this for, and what's something that you want your readers to take away from it?

Rick Catalano: Yeah. I wrote it for multiple audiences. You know, the Aspiring technician who wants to become a team lead or a project manager, the project manager who wants to get to the program level, the program leader who, you know, is worried about what we all have been talking about this whole time.

It's like, you know, it's like you're not going away, but again, it's retooling. Here's where you're gonna have, you're gonna have to up your game to get to the next level. A- And then I wrote it for the sponsors of initiatives so they can get a peek behind, here's what you're in for. Here are the fundamentals that you need to have in place to not be part of this, the 65%.

So those are the audiences I talk about, and it's really a lot of what we've been talking about, Todd. All these threads are interconnected, and I go in through all the principles, and it's, you know, for every one of them, and I lay out... I actually have a diagram called the, the AMIGO framework.

I unfortunately don't have it up and running, but it walks through the, each one of those things, and I talk about stories from the past. And again, this is, you talk about the warts. I mean, I bring up the warts, I bring up the lessons learned, and then I say, "Okay, and this is how the, the, the typical framework does, and then here's how AI can accelerate that or improve upon that."

And then we close out. And it's a working through the entire AMIGO framework block by block in a non-tech or tech-agnostic form. I intentionally did that because I didn't want it to be a sales pitch for AMIGO. Okay. Hey, you could do this without AMIGO. You know, it's and h- here's what you gotta do, and you could do it with the thousand document kind of thing.

Or it's or if you wanna... You know, and then the next part is, well then, you know, if you like what you're hearing and want to learn more, let me shorten that path for you because we've already built it, so.

Galen Low: And I think, you know, A, what I like about that is the multi-audience perspective. A, you know, good for marketing, but also it's a team sport, right?

There's no point for just one specialization in one room in some office to get this and no one else gets it. I think it's sponsor all the way down to the trenches. I think that alignment helps, that understanding of where things could go wrong and how we could patch them. And then the other bit is it still doesn't solve the problem of sometimes the data is not available soon enough for you to make a good decision.

Then it has to be technology, right? You know, it's probably not humanly possible for us to be like, "Just grow a bigger brain and keep track of these, you know, 10 million connections." Exactly. I really like that. I wonder if we can round out maybe by talking a bit about the future. Originally, I was going to ask about, you know, kind of this digital transformation marketplace and the sort of level of consultancies and how they're battling it out.

But I think there's actually a bigger question, and I hope you don't mind me going there. There's a bigger question here that I think underscores it all because you're someone who's very human-centric. You don't wanna have anyone who's out of a job, and yet s- there's still that that entry level that's disappearing on us, and I know a lot of people have their thoughts.

I went directly to analysts, right? The fresher is at a consultancy, that's usually how you got your foot in the door, and then it's basically like getting paid to go to school. You just learn school of hard knocks, how to be a consultant, and you climb up. But in a world where there aren't freshers or not the same type of role for a fresher for a analyst, like, where do people start in?

Not even just fresh grads, but people trying to move into consulting. What's their first port of call now?

Rick Catalano: I don't know I have a good answer for you, Galen, 'cause, you know, you see it out there. You see the, the job market for the kids coming out of school. It is tough because of this They are getting replaced.

You know, I wish I had a really, a, a good answer for you. I mean, I, I, I don't have a crystal ball. I mean, he's like, you know, one of the jokingly things is that I'm glad I'm on the

back end of my career, so I don't have to worry about it. So but no, it really is a serious thing, and, you know, smarter people than I probably have an opinion on that. I just... It's gonna be interesting. It's already impacting what things are going on today. You know, with most things, there's probably gonna be a turning point where, "Oh, we went too far."

Right. And then correct it. You know, we over-corrected, and now we gotta go. Like I said, humans still have to make the decisions. Humans still have to engage. There is the, you know, that part is still going to exist, but again, I just don't have that crystal ball to say how to fix the, what we're seeing at least across our country, probably around the world, with the newer generations coming up.

Time will tell.

Galen Low: I mean, so yeah, again, no one's got a crystal ball. It's hard to know the future. What I like about your solution or, you know, from what I've heard of it, is that it's built on knowledge, right? It's not just computation and algorithm. You set out to build the consultant in the cloud, right?

The folks who, you know, have done their career, you know, have the battle scars, and are able to just look at data and be able to tell you what's wrong. Also means you have some of the knowledge in there to be transferred to, to educate people, and maybe they don't have, you know, their mentor, right?

Who's going to, you know, pick their work apart and tell them what they did wrong and help them grow. But that information is there. It's in the platform. And, you know, I think there's ways... I'm a huge fan of AI is great for doing, but I wonder if it's not even better for learning, right? Where we can collate, like, all the knowledge that humans have put into a computer somewhere and be able to you know, not ne- you know, necessarily get a university degree every week, but be exposed to these experiences.

And that's what I like about the book, right? Over what you were saying. It looks like it's stories. It's this ecosystem of value. It's not just technology. It's not just education. You know, it's not just business acumen and experience. It's just all the things plugged together, right? You know, and you yourself, I think you're an educator, right?

We're teaching, we're building technology. We are spreading for lack of a better word, the gospel of, like, how things could be better. Don't just get stuck where everyone else got stuck because they got stuck. Let's find better ways together, and I think that's an optimistic view of the future.

We'll find our way. It might be tough, but I agree that, you know, we'll find our way.

Rick Catalano: You know, we haven't brought up and we haven't talked about the education part. So, the company's built on the, you know, so we have the consulting practice, we have the platform, but we also educate, you know, 'cause I'm a big believer in education.

Again, how do I up everyone's game? How do we get the next generation of enterprise transformation architects Prepared for what's coming, okay? I've actually built a mas- I call it a master's program. I, I don't sell it to universities, but it's master class level.

Galen Low: Master, yep.

Rick Catalano: Wanna do the deeper dive. It's already built, but you know, marketing and stuff like that.

We gotta ... I, I know, yeah, we just came out with the book. Let people read the book- Yeah ... and kinda just say, "Hey, I wanna learn more." So probably in Q3, maybe Q4 this year we'll, we'll start talking about the training. I think it's awesome. Again, it takes everything I talk about in the book, and then I go deep.

You know, I go, you know, deep into the nuts and bolts of how all this stuff works, and then you also learn AMIGO at the same time. But here's the best part of this. You know how you always have a class case study? The students of this course, and then this is the part I'm still building out the data for, they're gonna run a $100 million SAP implementation.

Galen Low: Wow, okay.

Rick Catalano: When I'm done talking, it is gonna be soup to nuts with all the data one would see, typically see, on a $50 to $100 million SAP type of implementation. Full backstory, everything, full avatars. It's gonna have 300 resources in it, approximately three to 400 resources in it. So and that is going to be the graduation present.

You know, the, to, it's like you'll get the ability to run a big, hairy, audacious, goal-driven enterprise transformation- ... practice simulation without having to have, you know, without ... You know, it's just a, it's a cool concept.

Galen Low: I love that. And you know what? Maybe that's the answer. Let me pose this question to you. Earlier we were talking about, you know, you're hiring people who have come out of the big consultancies for your own consultancy. Would you hire somebody who went through your course?

Rick Catalano: Wow, what a great idea, Galen.

Galen Low: Does it replace, right, that experience where you could be like, "Oh yeah, I've seen how a $100 million transformation program works, and it was hands-on."

Yeah, does that put them in the running for a job?

Rick Catalano: Yeah, and this is it. I gotta go to baseball. This is a note to Branch Rickey, who created the Major League Baseball farm system. This is my farm system. You know, then I get to, you know, see the, the students and see how they're doing, and then I get to pick the cream from the crop to come join me.

Galen Low: There you go.

Rick Catalano: In AMIGO. So that, that's you read the tea leaves. That's the vision. See the book. If you like the book, if you really, this is a passion area for you, and, and I know your audience, I'm hoping your audience, based on what you talk about, is this is a passion area for you. You want to learn this stuff.

And then, you know, then my job is to go, you know, find work for you, and this is what, you know, the revenue generating part of the, of our firm is going to find work. We're gonna need people to do this, and that's ... Yeah, and, and like I said, you know, they're gonna have the toolkit to lead this team of experts that we're bringing in to do the specialization of the technology work, and they'll be the leaders orchestrating this thing.

So that's the secret sauce and the how the, the AMIGO ecosystem works.

Galen Low: It's a good ecosystem, and it's for a noble cause. Like what you said rings true. We need to prepare people of any generation in the workforce for what's next, and I think that's a great way of doing it.

Rick Catalano: Thank you I appreciate that.

Galen Low: I, I appreciate you coming on the show. Just for fun, is there a question you want to ask me?

Rick Catalano: No, I was thinking about it. So, you know, how do you think that, you know... Tell me about your audience. Do you think they're gonna resonate to what we've been talking about, and what's on their mind in terms of the AI and what are you seeing from the lens of your constituents, so to speak?

Galen Low: I think it's a really good question. And I, I would say, you know, if you were asking me a year ago, I'd say everyone's r- got a lot of trepidation, right? Hesitance. And they don't really... They're skeptical, they're cynical. And some of those things are still true, but people are getting into it because they realize it's reality.

And what I keep telling anyone I can talk to, really, is that I think that's the right backstop on this progress that we're making is, you know, folks who can be a little bit skeptical or cynical or who are gonna challenge some of the hype that we have around the technology, but they're actually getting their hands in there now, right?

They're actually building, they're building workflows, they're reimagining things that, you know, we don't have to do things the same way just because that's how we've always done them. There's a sort of liberating aspect to it. And also, you know, I come from the agency world. I did some consultant stuff, but my people are, like, mostly in the agency world.

And I think listening to you talk about large scale transformation initiatives, you know, cutovers are cutovers. Yes, they get very complex, but there's translatable skills that we have. And for the folks in my community who are like, "Will we even have jobs?" I think the answer is actually, yeah, there's actually quite a few options available to us to cut across industry, to step into, you know, a different tier of the game.

And are there going to be loads of open roles? Probably not. But is this an opportunity, again, to prepare ourselves for an uncertain future and maybe, you know, succeed in an area where we didn't think we could succeed before? I think that is a really interesting message that's been resonating. And it's hard to see the future, and therefore it's hard to plan.

But, you know, just I, I think even just hearing you talk about some of these things, it's like, okay, yeah, I do that, but not at that scale, but I could, right? You know, I could level myself up. I, you know, you know, I could, I can hear the stories. I can, you know, learn the knowledge and hopefully get a little bit of experience and step up into that.

And, you know, like you said at the beginning, right, the number of digital transformations happening is increasing. Yeah, they're still mostly failing, but also I think if they can succeed harder, there's gonna be more and more transformation. This is not one and done like it, you know, sounded like in the early 2000s.

This is continuous digital transformation. This is gonna keep going. So I think that's really promising. I think, you know, the folks who are a bit cautious with the AI thing, they're probably using it better than the people who are not using it, and definitely better than the people who are blindly just, you know, buying into the hype and just still trying to replace a team of 25 using, you know, three lines of code.

It, eh Yeah.

Rick Catalano: I think those are destined for failure because you need the human in there. The human remains, you know, just but hopefully it gets better data, huh, at least with AMIGO. Love that.

Galen Low: I mean, speaking of, you know, you've got the book, you've got the course coming up, you've got AMIGO, you've got the Amiga framework.

For folks who wanna learn more about those things, like, where can they go?

Rick Catalano: I would say goAMIGO.co.

Galen Low: Okay.

Rick Catalano: So, AMIGO, put a little go in front of it 'cause I couldn't get AMIGO.co. So goAMIGO.co, that's where you can learn more about the company. I'm on LinkedIn kind of there a lot, so, you could find me there.

If you wanna talk one-on-one, be happy to have a conversation with you.

Galen Low: Awesome. Love that. I will include all those links in the show notes as well for folks who are watching or listening. And Rick, thank you so much for spending the time, sharing your insights, and coming on the show. This has been great.

Rick Catalano: It's a blast. Galen, again, thank you for the invitation. This was a lot of fun. Thank you.

Galen Low: All right, folks. That's it for today's episode of the Digital Project Manager Podcast. If you enjoyed this conversation, make sure to subscribe wherever you're listening. And if you want even more tactical insights, case studies, and playbooks, create a free account with us at thedigitalprojectmanager.com.

Until next time, thanks for listening.