Summary

The 180th episode of Coffee with Digital Trailblazers, focused on whether IT leadership in the AI era requires an IT background. Isaac Sacolick moderated a discussion with special guest Jason Gutierrez, who agreed that IT leaders need some form of IT background, particularly given the complexity and risks involved in managing AI systems. Other participants, including Martin, Derek, Joanne, and Elena, shared their perspectives, with Martin arguing that CIOs should focus on business outcomes rather than technical details while having enough technical knowledge to ask intelligent questions, while Joanne emphasized the importance of systems thinking and translation skills. The group discussed how business leaders without IT backgrounds can gain trust with technical teams through clear communication, understanding the “why” behind decisions, and removing obstacles that prevent teams from doing their best work. The conversation highlighted that while technical expertise isn’t required at the highest levels, IT acumen is essential for making informed business decisions about technology investments and managing the risks associated with AI implementation.

Speakers

• Host – Isaac Sacolick
• Guest speaker – Jason Gutierrez, Executive IT Infrastructure Director, Enterprise Cloud Migrations
• Digital Trailblazers – Derrick Butts, Martin Davis, Joanne Friedman, John Patrick Luethe, Liz Martinez, Heather May, Joseph Puglisi, Elena Putilina

This week’s discussion

Does IT Leadership in the AI Era Require an IT Background Anymore? –

1. What elements of an “IT Background” are more important for IT leaders in the AI era?
2. How can a leader with limited hands-on tech experience earn the trust of an IT team, define a technical strategy, and govern AI?
3. We need IT to develop business acumen – what IT acumen is most needed for AI adopters working in business functions?

This week’s research

Whiteboard

Transcript

[00:00:02] Speaker A: Greetings, everyone. Welcome to this week’s Coffee with Digital Trailblazers, our weekly event for digital transformation leaders.

Anybody who’s trying to derive value from AI bring change to their organizations. We meet every Friday at 11:00am Eastern Time to talk about a different topic. This is our 180th episode and if you ever miss an episode, you can go to drive.starcio.com Coffee. Our previous episodes are there. We’re also on Apple, Amazon and Spotify.

Do say hello on the comment stream. Let us know where you’re here from. Hello, David. It’s good to see you. Today’s topic, I’m super excited for this 1. Does IT leadership in the AI era require an IT background anymore?

And I’ve been thinking about this topic for, I don’t know, 10, 15 years.

We were just talking about in the green room about how every five or six years there’s an article from somebody, usually in a major publication, saying, you know what, things have gotten really easy and we don’t need it anymore. And it ensues a huge debate from those of us with IT backgrounds about whether or not you need it anymore. Hello, Marcus from Singapore. That’s awesome. Our special guest today is Jason Gutterrez. Jason, I just butchered that. I’m sorry.

Jason is joining us, who’s a longtime listener. And I just wanted to invite everybody who’s been a longtime listener. I am starting to invite some of you to come up and be one of our guest advisors on our program. So if you’re interested, do message me on LinkedIn and we’ll see if we can get you on a program. Hello, Jake. We haven’t spoken in a while. Okay, let me bring up some data points. Okay. And this is something I’ve been doing most, most of this year just to get us grounded in what’s happening in the industry today. We’re talking about this IT leadership in the AI era require an IT background anymore. And so I’m giving you on the left side two sort of opposing views. The top one is a bunch of quotes that I found from Deloitte Information Week, IMDb more or less stressing that IT background managers matters less.

The reality today is all about business. You could see a quote in here from the CIO at Commvault and he says, you know, it’s more important to be a business integrator.

There’s a separate quote here that maybe we still need CIOs, but maybe we should call them the Chief Intelligence Officer. And we certainly need to think about what Deloitte suggests, which, which is the era of the operational technologist is over.

And so what are we replacing this with now? I will give away my hand right away and I will tell you I feel pretty strongly about this that to manage IT you need an IT background. I never heard of a CFO that didn’t have a finance background. I never heard of a chro that didn’t have some experience in an HR department. I have not met marketers who have, you know, CMOs who are not marketers. And I feel pretty passionate that if you’re going to work in IT leadership, you need some form of IT background. And so I found you some quotes around that too. In the AI era, there’s a lot more risk. Technology may be easy, but governance is hard, costs are hard, complexity is getting worse.

True fluency lies in understanding how AI systems work and where they add value. I’m going to stress the part about where they work and where their limitations are. Are you need to know a little bit of what’s inside.

And in the Gen era, world class IT is defined by an ability to manage the massive volumes of complex data. Just one of the areas we’ve been talking here at the coffee with digital trailblazers. The skills that IT leaders need to have. Data is always one of them. On the right hand side I have some data points and some more quotes. One for me comes from a blog post. AI will take over all IT in the next two to three years. Said no one ever and I don’t believe it for a second.

Deloitte says 75% agree that operating models and processes must change within the next 1218 months.

82% of organizations are prioritizing human intrinsic traits over technical skills. We’ll talk about that.

And then on the bottom, Litcom had a really good set of data points around the skills that are in demand, the technology skills. So you have your human intrinsic skills, what we used to call soft skill skills, our communication skills on one hand, we have our hard skills on the other side and insecurity.

They’re pointing at skills like IAM, cloud security, threat dissection in DevOps, around architecture, infrastructure as code cost optimization as in FinOps and data and analytics, refine data engineering, data modeling and warehousing as some of the top skill sets. Folks, welcome to this week’s coffee with digital Trailblazers. Jason, welcome to the speaker floor. This is long overdue and I want to just share a little bit about your background.

Get people to know you a little bit more than what you can put in a common stream and then we’re going to talk about where you are in this debate. Does IT leadership in the AI era require a IT background? And you know, let’s find some gray area in our first question too. What elements of an IT background are most important for IT leaders in the AI era? Jason, welcome to the floor.

[00:06:00] Speaker B: Well, thank you, Isaac. Appreciate the, the invite too. You know, I have been listening for the past couple years and pretty regularly too, and this has been a great education, you know, for me as well, just to listen to you in the group discuss and debate these points.

You know, I’ve been in IT since the mid-90s, working professionally in higher education, primarily on the operation side. So currently I am the Executive Director of Infrastructure Technology here at Collin College in North Texas.

In that role, you know, I have a lot of operational technology, you know, either on PREM or in the cloud.

And as a leader in that area, I’m going to go with your, your assessment there. Just kind of like tip my hand a little early too. Yeah, you need to know it.

You know, we are in the age of AI, but, but where, you know, and I think that’s one of the things that this group has debated, you know, the maturity of, of AI. We see IT moving very rapidly right now.

I can’t really tell you where we’re at, but it feels like we’re still, you know, to me, in our infancy and we’re not ready to let go of those, those, those skills just yet. I don’t, I don’t see that, that we can replace knowledge of IT and run an IT business because there’s still a lot to, to be considerate of.

But, but talking about the elements of,

[00:07:42] Speaker C: of,

[00:07:45] Speaker B: of an IT background, what is important for IT leaders to know. And I think you’ve outlined some of those here already.

You know, especially leaders need to know how systems integrate, security, compliance. You mentioned that.

But I think with AI now being introduced into organization, the AI and ML life cycle, you know, AIOPS is a field now that we’re starting to see not so much in higher education, but in other organizations in healthcare. I was previously in healthcare. They’re starting to just get those, those types of roles provisioned. And I met with a healthcare executive earlier this week to, you know, just in an informal meeting we talked a lot about AI to see what they’re doing. And it’s still very much, we’re trying to figure out, people trying to figure things out. So I t leadership and the knowledge of IT is still very much Needed.

So how can you posted a couple questions and I wanted to touch on. But, and I’m sure we’ll do that during the course of this, this meeting.

But I wanted to go back to the original question. Does IT leadership in the AI area require IT background? And so I started to pull that apart, you know, and was thinking about what does IT leadership need to know about or you know, in, in the AI area, what, what do they need to know?

What is the AI era?

How do we define that? And as far as an IT background, you know, how much of a background does a person need to have, you know, in a leadership role? And I think there is some continuum between how close they are to the tactical aspect of it, you know, which is putting IT into production versus, you know, the business perspective of it, you know, the value of it.

Large organizations may have an IT leader who’s, you know, at a cabinet level who’s not hands on. They’re completely focused on the business outcome and objectives.

But in smaller organizations you’re going to find where, you know, IT leaders may even be, have some tactical role or be very close to the, to the execution which requires them to have a much deeper and broader background in it. So I think some of that also kind of plays into my perspective.

[00:10:31] Speaker A: That’s a good point, Jason. You know, size does matter.

You have a lot more broader responsibilities as an enterprise cio.

You’re probably not going to be dabbling in code as an enterprise cio. On the flip side, I know some very small company CIOs that are almost too hands on, almost to a detriment, but get to look for the forest and are stuck in the weeds and the trees.

I’m going to be interested to hear from, you know, Derek, Joe and Martin in particular, you know, those of us who have had, you know, some operating backgrounds.

And I know I’ve walked in, I’ve taken over CIO roles from predecessors who do not have an IT background.

I’ve walked in as a fractional CIO and as an advisor for star CIO in companies that did not have people with IT backgrounds managing their it.

And in a word, they are a mess.

And it’s not to say that non IT background people can’t manage it.

It’s just it takes a lot of work to build up that technical acumen.

And that’s what we’re going to be driving into and delving into a little bit more. Derek, your first hand raise. I’m going to give it to Martin first though. Just hold off a Second, Martin has limited opportunity today to speak with us. Martin, your thoughts on this topic on is IT background important and what are the most important IT background skills to have?

[00:12:03] Speaker D: Okay, so let me put this in perspective. I’ve been CIO for about a dozen companies in my time ranging from a couple of hundred million up to a couple of billion. So yeah, but I’ve also worked in even larger enterprises as well. So I, I come from that rather than a small company background. So I’ll just put that in perspective and I put a comment on the comments stream a couple of minutes ago, which is that a cio, if they are in the detail of technology and right into the technology, they’re no more than an IT director, they are not a cio. So I’ll, I’ll come out and say that to start with and I’m going to get flamed, I’m sure, but that would be the perspective I would throw out there. A CIO is. Yeah. And call it Chief Innovation Officer, Chief Information Officer, chief whatever officer is driving how the business should move forward.

So they are a member of the C suite.

They like any other member of the C level, they are looking at the business and the company and how the company should be moving forward. They should be talking the language of business with their colleagues.

Where CIOs fail is when they don’t talk the language of the business.

But they then also need to take that and translate that into how IT needs to run. How the IT leadership need to understand that business side and make it happen. So it’s the job of the IT leadership, the IT directors, to actually make it happen. The CIO needs to have a technical background to a fair degree because they need to understand what questions to ask and how to drive things forward within it.

They do not need to know how to code.

You know, I’ll throw that out there. They need to know the questions to ask and what is stupid and what is not.

That is kind of the core of this. And then employ good IT directors beneath them to actually drive the different areas forward. You know, I’ve run IT teams from 100 plus people down to as low as 10, 15 people and the same principles still apply.

You’re trying to actually translate what drives the business forward into it. And you’re trying to. CIO is trying to stop, you know, the company doing something stupid, trying to stop cyber attacks, all these types of things.

But you’ve got to look at it holistically. You’ve got to be a business person.

But the CIO needs To have a technical background to understand how to step between those two worlds.

[00:14:44] Speaker A: Completely agree, Martin. I mean you’re separating role, responsibility, function and mindset versus background knowledge. A big part of what CIOs need to do is ask good questions. And I think the, you know where the rubber hits the road, right, Is that every, every incident and every innovation, every has multiple ways of solving for it. If you have an amazing set of lieutenants in security, in application development, in operations who get along and collaborate, they’re going to make that job for that CIO a lot easier because they’re going to find a way to present trade offs and come back with a consensus. It doesn’t happen very often.

I mean, that’s just the reality. And the technology changes very quickly and the trade offs aren’t always all that easy to make. Derek, love to hear your opinions on this.

[00:15:40] Speaker E: Yes, good morning. Yeah, I strongly agree with the, the IT leader needs to have some sort of technology background in it or at least technology.

As you mentioned earlier, they don’t have to be the best coders, they don’t have to be a cloud architect, you don’t have to be the best engineer. But they do need to understand how the technology works, how artificial intelligence works, how it also creates risk, but also how it can create opportunity. I think when you look at the business value and how that aligns with everything the business is trying to do from the mission, it’s important they understand that the IT background matters and, and the things that I would focus on is looking at as a former CIO and a former ciso is the cybersecurity, the resilience thinking. Are they looking at how systems would fail and how they would be able to endure in an attack? Do they have the quick recovery? When it comes to the AI era, I would look at data, AI literacy. How well are they understanding the data that’s being fed into these systems and understand the quality of the data, the governance, the privacy, the ownership of the data all across the business units within the company. When you look at it also from an architectural point of view, you know, they’re not designing the systems, but they need to understand how the cloud interfaces work, the applications and also Most importantly, the APIs. You look at how these systems are connecting to other systems that are out there. These API allowances or gateways or hubs are actually allowing these models to actually interact with one another. And that’s something they need to understand from a risk point of view because the risk management looking at that what AI introduces is going to be huge. So they need to understand about the, the issues, the risk, the manipulation, the data leakage, the hallucinations, all these complex things are going to be associated with AI, but also the third party risk that are actually associated with other people using AI. When you look at the technology economics, they need to understand, like I mentioned earlier, Isaac, the business value. They need to understand how it’s going to give them a return on investment when they’re looking at the tech debt of companies they’re going into, but also the technical trade offs based on the innovation, the operations and the opportunities it’s going to bring to the companies. So yes, they need to understand, you know, the technology across the board. And I agree with you said earlier, they don’t need to be the best, you know, engineers and whatnot, but they need to understand the resilience aspect of how digital transformation is going to take place using artificial intelligence.

[00:17:59] Speaker A: Good stuff there, Derek. I mean, your last comment just makes me think of one of the problems folks without an IT background struggle with. It’s just being able to sell the importance of addressing technical debt or data debt or security debt.

They are, you know, the, the, the issue, just understanding the risks when your team isn’t necessarily going to be versed in explaining those to you. I mean, the coat smell bad, smells bad. A developer will say that to you and you have no idea what that means until you, you know, buy and dive into it and really look at it and then yes, too late is what you’re worried about. Joe, I’d love to hear your opinions on this.

[00:18:41] Speaker F: So I’m going to go in two directions. Isaac. First, I think context really matters a lot.

We could talk about automobiles, right? And one can drive an automobile and know nothing about internal combustion engines and suspension. And if all you’re trying to do is get from home to the office, you can drive a car and you don’t have to know much.

But if you’re a race car driver, you have a pit crew and the objective is to win the race, you better damn well understand how that car works and what you need to do to have the edge over your competition. So first point is, context really matters in the sense of whether I have to know a lot about technology or maybe just a little bit.

But the second thing is, not surprisingly, I think a key attribute of technology leadership is communication.

It’s the ability to be able to convey what it’s all about, as Derek just alluded to. Why is the data important?

People generally don’t understand that what kind of software are we talking about? What business problem are we trying to solve? What tools do I have to address it?

Making that bridge, if you will, between the business leaders and the technology that you understand is, is all important. I think the, the last thing I should probably say is that like the CFO of a company, one would never say a CFO doesn’t have to have an accounting background. I mean, that’s sort of ludicrous. Right?

But his role is not that of a bookkeeper.

He’s not going to be making the debits and credits and entries. He’s going to talk about how do we best leverage our working capital, what sort of financing fits our business model best, or other strategic decisions and maybe some tactical decisions in a smaller organization.

But to, you know, to say you could get away with no accounting background, I think that just doesn’t fly.

[00:20:46] Speaker A: No, I, look, there’s a set of cases where you don’t need a cfo, but you need an accountant.

And there are many companies that don’t need a CIO or transformation officer or even a security officer.

If my back Office is essentially QuickBooks and I use Microsoft Office for my office suite and I have a service provider handling all my end user computing and I have a security, a service provider handling some security audits, you know, I probably can take care of that without an IT background. But those are, I’m just going to put those as edge cases. Right now we are talking to digital transformation leaders. We’re running complex organizations, we’re trying to use technology, data. And now AI is a, is a tremendous technical advantage in our business. And I’m going to bring Liz up. Liz, I want you to lean into the second question. I want to hear what you think is important in an IT background. But I want you also to talk to us about how to gain trust with very skeptical IT teams. And all of us who have been CIOs know this is that when you put a manager or director in front of them, that’s less technical, wow, their eyes glaze over. This person doesn’t know what I’m talking about and gives them no respect. And so it is a two way problem.

[00:22:11] Speaker D: Right?

[00:22:12] Speaker A: It’s not just a director coming in without an IT background. It’s, you know, it’s the staff who just wants to talk shop and just, you know, gives no room for somebody who comes in to teach them, to educate them, to show them. How do you gain rapport in those situations? Liz, I’m giving you a crack at both answers.

[00:22:30] Speaker G: Oh my goodness. There’s a lot. There’s so much there.

Okay, so number one, I think when we’re talking about CIOs, I think that there’s so many different types of CIOs.

But see, okay, so the role, in my opinion, the role of CIO is, has always been so difficult in terms of business leading and IT management.

I’m going to get to your question, I promise.

And what’s happening as we move into this era of AI? It’s actually turning into three distinct roles. And this relates directly to what you were saying about IT teams having some level of respect for a leader who doesn’t have it.

The key is always around roles and responsibilities.

Like, what is each person’s role in bringing this thing forward?

If in fact the role is around technology?

Of course they have to have a technology background, but to me, that’s more of a cto, not so much a cio. So if we take the technology piece and put that to the side, and then there’s a governance piece, which is security and management and data governance, all things governance. It’s a whole nother piece. And then there’s a whole nother piece that has to do with understanding the business and leading in a direction where you’re influencing how those IT tools can actually benefit the business and move that way. Those are three distinct roles.

And if you’re working with an IT team where you do not have that IT background, but you do have some strategy and business background, or you do have some governance background and you lay that out as a part of the opening and the respect, when you’re working with them, then they can actually latch onto that, right? You actually can share with them. Guys, I know that I’m here, you know, trying to lead us, but you are the IT experts.

What I bring to the table is helping us govern or helping us strategize or helping us move in a direction that’s going to be good for the business. Let’s see if we can partner.

And that helps acknowledge and build that trust. Because you know that your team is not going to be overridden by some leader who doesn’t know what they’re talking about.

[00:25:11] Speaker A: Liz, I liked where you started. I actually think there’s more than three roles, and I think that’s the art of a CEO and a board working with a recruiter to say, you know, what of the vast array of Persona, skills, background, mindset do you need in your CIO themselves?

And then when a CIO comes in, the very first question they need to be able to do is where do I need really strong lieutenants.

I was always on the data and innovation side. I always look for really, really good operators who would push back against my innovation teams. And I was always looking back for somebody who was a very strong people person to be my head of PMO at the time, knowing that I would be moving very, very fast and I needed somebody who would come to me and say, isaac, the group needs to slow down. If you have questions around that, I tell about those experiences in chapter eight of Digital Trailblazer. It’s a really good chapter about how you formulate your leadership team. Thanks, Liz. Joanne, how’s it going?

[00:26:21] Speaker H: Well, the sky is not yellow, so I guess that’s a good sign.

Although it’s still very, very smoky up here.

I think I would like to take this in the direction of you don’t have to be a dev, you don’t have to be an ops person, you don’t have to be even an engineer. What you need to understand is systems design and systems thinking for the AI era because it is all encompassing. And the role of the CIO now more than ever really has to be the chief Translation officer because you’re not necessarily going to get the biggest picture possible from those below you in it. You’ll get the details, but it’s not about translating a business need. It’s more about translating a corporate strategy for competitive advantage or resilience or growth or innovation into both the how the business deals with AI and how technology professionals deal with AI. And that’s where I think to your point about there are many roles it really comes into play because in the AI era you have to have a holistic perspective. You have to know where the impacts are going to be of what you’re designing from the technical point of view. So if you don’t understand the technology below a high level that can be acceptable to your point about having those below you that are more tactically oriented. But you really have to have a very good sense of what overall systems design looks like because if you don’t, you’re just recreating silos with a new twist.

[00:28:12] Speaker A: Joanne, I think your point connects to where I started from when I say I walked into a mess and it’s that lack of systems design thinking that really comes that and you know, waterfall project management methodologies and a whole bunch of other things. But it’s really the systems design thing that falls apart. That, you know, the easy thing to have done years ago and I think it still exists today, is to manage by contract.

Right. And I’ve got, you know, contracts with these vendors, I’ve got for platforms, I got contracts with these service providers with SLAs around them and you know, try to, you know, basically match make between business requirement into how you fulfill that. Joanne, I just don’t think it works. I don’t think it ever works.

[00:29:01] Speaker H: It doesn’t. And you know, it was interesting. I had a conversation with someone yesterday. Sorry if I cut you off Isaac, I didn’t mean to.

1900 SAS providers and apps running in the organization.

Where do you even put a number around technical debt number one. And how do you bring that all together if you’re not a systems oriented person?

As a CIO and in my roles as a cio, that’s what I always brought to the table was that bigger picture, you’re not going to be able to succeed with AI.

It’s just going to make it worse. It’s going to exacerbate all of the points of failure in execution between business objectives and it.

And we’re already seeing that start to happen. There are gaps, trade offs, handoffs. You know, you can’t make it from point A to point B unless you take that background that you have, cto, cio, even director level.

You have to pull it together in, in this bigger picture. Thinking Blue Ocean is making a comeback, so is systems design and systems thinking.

You’ll see it become more prevalent over the next year because in agentic AI in particular, that’s a silo and unless they’re governed from a bigger picture perspective, you’re just making a bad situation even worse.

[00:30:34] Speaker A: Thank you Joanne. I want to go straight to Elena. Elena, I hope you can answer this question about gaining trust with it, but go anywhere you want. Welcome to the floor, Elena.

[00:30:47] Speaker G: Thank you, Isaac.

[00:30:48] Speaker I: I am actually going to answer this question pretty much firsthand because I was that business person that was put in charge, charge of technical teams and the leadership level. It was not it, it was analytics, delivery and operations, but they were very technical. And the situation that you describe where they look at the leader and say but you’re not technical and roll their eyes, that was done to me probably for good six months.

So I know firsthand what that’s like.

The way I navigated out of it was leaning into change management because we had a lot of organizational problems surrounding technical problems. And I pitched to my team that I would solve their organizational and change management problems while they teach me the tech end of it. And it was a long road. But we arrived in a good place, but again, that was a small subset of what we’re talking about. And I definitely would say don’t do that putting a business person to head it, because there is a lot of, not only the trust, if you like, joins that AI systems thinker and if you’re good at change management, if you understand data and tech debt, you can kind of get that. But AI and risk and what’s going on right now, that is very difficult to know if you’re not from the field. So I would definitely advise against it. And on this subject, I think when you talk about in the era of AI, I think it’s the risk that’s created by AI is the most important factor in this conversation. Because on the business end we all want to talk about all the benefits, all faster, more productive, etc. But as business people we’re not close enough to how it works to understand the risks. So begging for IT leaders to be IT professionals who are very well versed in risk for the sake of all of us. So that’s my piece.

[00:32:54] Speaker A: Thank you. Elena. You know, you bring up a really good point because we sort of translated in the first half that, you know, IT leadership is cio. But most organizations of any size today really have some kind of fungible distributed IT team. You see, you know, digital teams that are separate from it. You see data teams like you had Elena, that’s separate from IT teams.

Very often security and IT are not under the same leadership. You have enterprises that have business unit CIOs with a different charter than the enterprise CIOs. There’s, there’s a lot of nuance here and it really comes down to you are going to have not necessarily a CIO or chief or data office digital officer. You’re going to have somebody in your organization, a VP or a director that probably is, is overseeing a technical function that doesn’t have all of the hands on background that their team has.

And how do we make people like Elena successful? That’s really part of this equation too. And part of it is giving you patience. Right? Six months to develop a rapport with the team sounds about right when you’re also learning about the job at the same time. Thank you for sharing that. We’re going to go to John and then I’m going to take my break after that. Hello, John.

[00:34:12] Speaker C: Hey Isaac. Thank you for having me on.

I’m on the team that the question is how technical and how hands on does this leader have to be?

I think that’s really the only question, I think, unfortunately, when I’ve gone into really dysfunctional IT organizations, what I’ve seen is that the people that the next level down that are leading things, they’re highly technical. But the places that I really see issues are, or your culture issues, and I also commonly see leadership issues. Right. And so if you come into a hostile organization, I think you got to meet all the, as many people as you can in the organization, people of all levels.

I think if it’s really toxic, and I think one of the things you can always do is do an assessment and share the results out with people and look across all the things that you see and be very honest about what’s going well and be very transparent about what you see is not working. Right. And that’s, that’s the only way that as somebody new coming in that you kind of can put people in their place when things are really dysfunctional. And then, and then leaders, they, they chart a path forward, right. And so you have to bring a vision out of like, how do we get this organization into going in the right direction and share that out with people?

So that’s, that’s my view on things like, you know, with, with AI, it’s, it’s a new technology, it’s transformative, it’s going to change everything. Right. And so that’s, you know, the only way that you can be dealing with new technologies and not get burnt is to look at the learnings of the past of rolling out new technologies. Right. And that’s, that’s why the IT background’s so important. That’s why having, looking across all the different and, and that doesn’t mean to say that the leaders have to be like actually coding, but that they, they have to be understanding what people are doing and they have to understand which direction the org has to go and, and how it works with the rest of the company.

[00:36:07] Speaker A: Thank you, John. Folks, welcome to this 180th episode of the Coffee with Digital Trailblazers. We meet every week talking about issues, areas of focus, ideas, risks that are impacting our transformation. Leaders, those leading digital AI data and security marketing product, you’re all welcome here to learn and share your thoughts.

Today we’re having a wonderful common stream. If you’re on the LinkedIn Live program, you can see it going on. Some really good advice that I’ve been able to capture in today’s whiteboard. Our conversation next week will be about the financials around AI and managing AI costs. We’ll break this down into innovation, production and its life cycle. The 31st. We’ll be talking about evaluating technologies in the AI era around value, risk and ecosystem evaluation. Do join us to find more about our past episodes and listen to them and to get the links to join forward our future episodes. Do Visit us@drive starcio.com Coffee I do want to give a shout out to my advisors here, those who are joining here every single week. Joanne, Joe, Martin, Derek, Heather, John, Liz and Elena, thank you so much for joining. This week we had a, a little bit of a brainstorm week. We found a good time to meet and we said let’s use some time to think about what we want to improve on and change in the coffee with digital trailblazers going into the future. We came up with I think 10 to 12 solid ideas that I’ll be working on over the next, I would say one to six months. I want to just thank you for being committed to this program and your engagement just about every week that you can join us. So thank you. Jason is our special guest this week. Jason, I’d love to hear your thoughts on how you gain trust with the IT group, particularly when you have somebody on your staff that is less, has less technical acumen or may have not had a hands on role. And then I’d love to hear your opinion. How do we develop IT acumen for business leaders? The street has to work both ways. We need our IT teams to have a lot of business focus and acumen. What do IT leader business leaders need to know about it? So give us your thoughts on both of those questions. Welcome back, Jason.

[00:38:36] Speaker B: Thank you. Yeah, I’ve been listening and a lot of good points. John, I think you had some good points too I wanted to go back and touch on because some of that I think goes back to culture, you know, in the organization.

You know, a bad culture will eat innovation. Right? We’ve all heard that, that quote.

And so it’s really important to, you know, gain the trust of, you know, those people. So from a leadership position, you know, you know, I’ve said this to my teams and I’ve even said it recently to my teams and I’m very jealous for the, for the culture of the team that, you know, we were purposeful on what it is we’re trying to create in terms of, you know, an environment, in terms of a working ethic and you know, where, where our focus is and if there are people on the team that, you know, we, we endeavor to, you know, bring into that culture and, and have them, you know, acclimate to it, you know, most times it works. And one book I’ve really leaned on was the, the Ideal Team Player. I don’t know if you’ve heard of that book.

It’s, it talks about, you know, how to develop high performing teams. Another one, a good book I’ve mentioned before, is Herding, Like Herding Cats, but Herding Tigers by Todd Henry.

Another good book about high performing teams.

But when you have a high performing team and you can bring in leadership that can connect with them on that and that and connect with your vision, you know, as a leader, I think that goes a long way in trying to develop that trust.

So cultivating and finding it expert leadership in the areas that you need is important.

And then as a leader, you know, clearing the road, you know, being able to get rid of those obstacles that prevent great people from doing great work.

A lot of times I think teams can be sidetracked because of politics, you know, and so as a leader, can I clear the road? Can I serve them and give me, give them the opportunity to do their best work by getting rid of some of those obstacles.

And then another point that was mentioned as my last point here, knowing why you are doing something and translating that vision to the workforce, really bringing home the why, that was also mentioned earlier. But it’s, it’s not something that should be understated and you know, it’s something that you really need to focus on. Why are we doing this? Why are we here? What are we trying to accomplish?

You know, what do we want to be when we grow up? Essentially, you know, so I think if you can translate the why and the vision to the workforce, then I think that also goes a long way in building trust. And, and so when we introduce new technology or disruptive technology, they’re not left guessing, you know, what’s going on and trying to fill in the blanks. We need to communicate. And that was another point somebody I think John even mentioned earlier. But communication is key.

[00:41:45] Speaker A: I think that notion, Jason, of clearing the road of obstacles, any good leader and manager should know how to do and few rarely do well. And I think it’s particularly relevant when you’re managing technical folks who by definition have more demand than time.

And there’s lots and lots of distractions to pull them in different directions.

And you know, a good leader and a good manager is going to step in front of the team and protect their time and protect their ability to stay focused. I think that’s really good advice. Anybody can do that. You don’t have to understand technical and believe me, your team will respect you for doing that.

The other one is translating why down to business, to our people working on things. Translating why is not just about building business focus, it’s about why we’re making certain trade offs. How many times have you heard from IT teams that we’re pushing the team too fast and they can’t get their work done meaningfully. And so a good manager is going to explain why that’s happening or how to make the right trade offs under those circumstances. So really good advice there from Jason. Derek. You had your hand raised. Love to hear what you have to say.

[00:43:03] Speaker E: Yeah, I think when you, when you look at the, the aspect, like I said, either the engineers and whatnot, the, the trust, how do you get that to be formulated?

When you go back, you need to look at the fact that they’re not going to have be the smartest guys to understand it, but you need to understand the technical aspect of it. And I think that leader coming in there needs to know how to understand the technical risk. Elena alluded to this earlier. Understand the risk associated with, you know, the AI risk management, the cyber security fundamentals, the data governance, the cloud operations, all these things now are exacerbated with AI because at the rate and speed at which they can be translated and at the rate of speed they can actually introduce risk into the company. Now understand the AI governance early is going to be key. They need to understand that these policies need to be updated to now formulate to further address AI, specifically the human in the loop. Oversight is something that can’t overlook that we talked about that a few episodes back. But also just how risk is assessed, AI threat, intelligence, visibility is something a lot of companies still lack. So they don’t understand the risk that’s taking place within their network.

If I move into the next question, you asked about the IT acumen, understanding the limitations of artificial intelligence across the board, you know, mentioned earlier, the hallucinations, the bias, the model drift, all these things that are key when it goes back to AI data governance and understand the sensitivity and how it may expose their data and if that should happen, what do we do? How do we recover? How do we regroup these things? When it comes to cyber resilience, the mindset of how the AI platform becomes working, what happens when it doesn’t become working, what happens when we have shared external data externally that we shouldn’t have shared? What happens when we can’t verify the output or fall back on processes that we used to know because AI has taken over the, the risk associated with the business goes back again, the why that you guys mentioned earlier, but also the business impact. Do we align the AI tools with the business values? Do we line it with the business mission? Do we line it with the business overall? And the biggest thing, when you’re looking at this AI governance, it’s not just the it’s responsibility.

When you’re looking at this across the board, the companies need to understand this is a business culture issue, not just an IT leadership issue. So the marketing, the HRs, legals, the finance, all those companies need to understand the data privacy, the ethics, the compliance, all the things associated with that. The shared responsibility across the board early is going to have a more successful company on the outcome in this AI era.

[00:45:34] Speaker A: Derek, you went in some places I thought you’d go and you left one out, which is, I think part of having strong IT acumen means that you need to have some standards, you need to have some, you know, some selections and frameworks, you know, you know, you know, some of us have construction backgrounds. We don’t let every, you know, every construction team just show up with their own tools and let them start working. We don’t let our doctors pick their own tools in a hospital. There’s some standards in place. And yet as soon as you have that conversation inside an enterprise, it becomes, I don’t want to give this up.

And you know, it brings up Raymond’s comment around change. Management has always been a hard problem to address rather than replacing technology.

I think Martin saw the softball and his hand is raised. Hey, Martin, you like how I connected all that?

[00:46:33] Speaker D: Yeah, I wasn’t gonna go there at all, actually, but I will if you want.

[00:46:36] Speaker A: Yeah,

[00:46:38] Speaker B: yeah.

[00:46:39] Speaker D: The whole thing is about, you know, change and everything else. Yeah, I’m not even going to go there. I won’t go there.

I think one of the key things here in terms of IT acumen for a CIO or for a senior IT leader is knowing enough to be dangerous. And I love the quote earlier on from Steve Jobs is you’re hiring smart people to do smart stuff and they should be telling you what is important. They should be telling you how things should balance and everything else.

The CIO needs to know

[00:47:11] Speaker A: enough about

[00:47:12] Speaker D: the subject to have an intelligent conversation.

Both I said earlier about from the business perspective, but an intelligent conversation with their IT leaders as well. And they need to know what is feasible, what is not feasible, what will fit within the organization both architecturally and and culturally, because those kind of debates are real key as well. So in terms of IT acumen. The having a good grounding in IT is important, but you don’t need to be a coder. Yeah, I, I come more, I’ve always been more of the business side of IT and driving business value and that’s where I come from. But I know enough to be dangerous. You know, I’ve coded in C in my time and other stuff like that. I, yeah, dabble in different stuff occasionally, but I’m not a coder or anything like that. I don’t go out and code. Probably 30 years ago was the last time I coded. But the difference is I know what a database is. I know about relational data, but I know some of that kind of background. I know what a good enterprise architecture looks like. I know what a bad enterprise architecture looks like. I know what makes an IT function properly or badly. Yeah, and knowing all of these things, how to structure IT for success, that then plays into how does AI play within our organization?

And then there’s obviously different aspects to that. Change management is one of them cultural fit and how should we be using IT and how should we using AI in this organization? So there’s a lot of different aspects you have to balance there. And a lot of that comes from having some background knowledge, knowing the right questions to ask, knowing enough to be dangerous is how I often describe it, and knowing the right person to ask to get the answers you need. And that’s important, knowing the right person to ask. And that right person could be Claude or could be one of your IT leaders.

[00:49:12] Speaker A: Now you’re throwing a softball back at me, Martin, because you know, in Digital Trailblazer I talk about the importance of being able to encourage collegial debate, particularly around technologists. And you brought up some of the reasons around it. Right. I want to understand feasibility, I want to understand performance, resilience, innovation, trade offs. I want to be able to future proof my decisions. I want to get a better sense around cost rather than hard dollars and hours, but where the complexities are going to lie.

These are the kind of conversations that you need to be able to have as an IT leader, whether or not you have an IT background.

And I’m not, you know, sometimes I do see it in code. I tell a story in Digital Trailblazer of a development team spending thousands of lines of code to build very primitive data visualizations. And I looked at it and I said there’s no way this is going to be sustainable. I can’t invest a thousand lines of handwritten code to build a line chart. You know, so sometimes you could see it right away, and sometimes it’s buried deep and you actually need tools to be able to see where the technical debt lies. Who’s raising their hand? Joanne, Go ahead, Joanne.

[00:50:28] Speaker H: Thank you. I think, you know, you have a very interesting question there. IT acumen for business leaders, as a cio, as a cto, anytime you are interacting with the business, you not only need to understand the lingua franca of the business and its industry, but to begin to educate business leaders around what AI is and what it is not and to dispel the myths. Because think about it. You know, if you’re an executive and you’re traveling all the time and whatever, you read a lot of stuff on the Net, you read a lot of stuff in, in publications, there’s not so much fear, uncertainty, and doubt as.

As there is much more of a and what do I do now and what do I do with it?

And that’s where I think the IT acumen for business leaders really comes in. It’s understanding what is this piece of technology going to do for you, but in terms that they understand.

And that’s not so much a translation issue as much as it is being able to frame a technical capability in a way that a business leader is going to recognize. No, I don’t want to go down that road. I want to go down this road instead. The difference between an AI wrapper or generative AI and agentix, it’s making those distinctions very clear. That’s the acumen that business leaders are going to need, because that goes directly to their ability to make better business decisions.

And that’s the kind of programming that I’m seeing a lot of companies struggling to find, but very much in demand for.

And so I would say if you’re in a C suite role as a CIO or a cto, part of your obligation to the business is not only the educational aspect of it, but in framing it around the things that the business needs to be resilient or to create competitive advantage.

[00:52:44] Speaker A: I love this quote from that’s on the common stream. Just make me think, nobody needs the CIO writing code. They need someone who can spot a bad architecture decision before it costs two years.

Also need to be able to look at five architecture bad decisions and say, you know what, this is the one that I need to start with.

This is the area that we need to focus on first.

And I’d love to hear more about IT acumen. We may have to do this as a separate conversation, but I think that’s really one of the biggest challenges we’ve had the last 20 years, and I think it’s an even bigger challenge over the next two years is this idea that it’s all easy, right? We can vibe code our way through our problem, we can throw AI in and it will take care of our workflow and make decisions for us.

I actually think we need to give this its own due course. We got four hands raised and we got six minutes. Go ahead, Jason.

[00:53:46] Speaker B: Yeah, I just wanted to piggyback off of Joanne’s comments there, which are always great join. You have the best comments. I just love them.

Feel like I need to send you a tuition check somewhere.

But on the, you know, the part of the role, you know, in it general, across the whole spectrum of, you know, and the whole hierarchy, we all have to be lifelong learners, including the cio.

And the CIO has to be that, that person that can help, you know, when they manage up, so to speak, at the board level, you know, to, to help them understand, as Joanne, as you’re saying, what, what the, the value is of us, what are they trying to accomplish? Because I mean, AI is, it’s buzzword that’s out there. Everybody wants a piece of AI and I think we see that in this past couple years that people are wanting more AI and will to do what and they really haven’t defined the problems with or examine their own data, you know, to see if they’re ready for it. So how can we, as, you know, leaders talk past the hype and perhaps, you know, pump the brakes a little bit or kind of reset expectations? And I think that’s a keen point that Joanne makes. Like we really need to focus, you know, their expectations on what it can and cannot do. You know, it’s, it’s a non deterministic, you know, you know, process, you know, whereas people want deterministic output.

You know, AI is really good at non deterministic outputs and so how can we use that? So I just wanted to chime in with that.

[00:55:28] Speaker A: Thank you, Jason, for joining this week. It’s been a lot of fun. We’re going to go to Elena, we’re going to go to Joe. I saw your hand up, you’re coming back on and John, Elena got five minutes.

[00:55:39] Speaker I: So it acumen for the business leaders, I think AI is redefining how much as business leaders we need to understand and what we need to understand.

And I think based on that, the way business leaders and tech leaders communicate and work together in the organization’s needs to change. Because up till now There is still a divide. You’re on the tech side, I’m on a business side and we both mind our sides. This needs to change. We need to work very closely together. AI runs faster than us. So as business leaders, we need to feel free to ask questions and technical leaders need to understand that we need to be educated. Before we went ahead and did something, you know, like you guys gave many examples. So I think it’s on the change management, it’s on the communication side and it’s on constant learning together, both on a business side and on the tech side, which is where we need to strive for.

[00:56:43] Speaker A: Thank you, Elena. Joe, I know you had your hands up. What do you have for us?

[00:56:49] Speaker F: One more analogy. I was thinking about sports teams and in some ways tech leadership is like being the coach.

You know, you don’t have to be an excellent player, but you better understand the game and the strategies, strengths of your players and, you know, keep the owners happy.

[00:57:07] Speaker H: Right.

[00:57:08] Speaker A: That’s a good one, Joe. I, I’ll give that, I’ll give that one a nod. Although, I think, you know, if it really did some keep. People keep saying context, you know, I was able to coach a 5th through 8th grade soccer team without a whole lot of knowledge about how to play the game of soccer. But if you’re going to go, you know, coach a minor league team, you probably need to have some really good understanding, not just of the game, but the entire dynamics, the strategy, how players think nowadays, some of the technology that goes into it. I, you know, I think as your scope increases, your acumen increases with it.

[00:57:48] Speaker F: Yeah, absolutely. I know. Not as good as Joanne’s stories, but it’ll have to do.

[00:57:52] Speaker A: Oh, I wasn’t trying to poke holes on it. I was just like, let’s just set some realistic boundaries over, you know, what are some edge cases over here? John, you got the last word today. Twice in a row.

[00:58:03] Speaker C: Yeah. If the IT leaders can. Can just do two things. If, if they can make sure that the IT Org is doing everything that they really have to do and then if they can make sure that they’re taking the rest of the capacity and making sure it’s. That it’s being pointed in whatever is adding the most business value, those are the two things that are critical, folks.

[00:58:22] Speaker A: Really excellent conversation today around.

Does IT leadership in the AIA era require an IT background anymore? If you enjoyed listening to this program, I have two asks of you. Do visit drive.starcio.com coffee. You’ll see the links up for the upcoming episodes. One on finances and managing AI costs next week, the one after that on evaluating technologies in the AI era. There’s a form there for suggesting topics. If you want to be a speaker on here and you’re listening in, do direct message me. We can talk about that.

If you like this program, do share this with your friends. Once you click to join an event, you’ll have the option to invite your own friends to the event.

Do consider doing that. Help us grow the coffee with digital trailblazers.

Everybody on the east coast of the United States, please take it easy. There’s a lot of smoke in the air. I’m not blowing smoke about that.

Joanne, do take it easy out there in Toronto and we’ll be back here next week. Again, we’re talking about FIN AI and managing AI costs. We’ll talk about the balance of innovation, what it takes to bring AIs to production, and the full lifecycle management around AI. We’ll be looking at it from the cost equations next week. I do have a really good architect joining us next week as a special guest. Folks, everybody have a great weekend. I’ll see you here next week.