
Phil Howard & Stephen Chen
408- Your Career Isn't Defined By Technology w/Stephen Chen
408- Your Career Isn't Defined By Technology w/Stephen Chen
Stephen Chen
ON THIS EPISODE
Stephen Chen was hired as CTO to lead digital transformation at NuCompass Mobility. What he found shocked him: 80-90% of the work had nothing to do with technology.
"Eighty to ninety percent of this digital transformation effort, it's not really about technology. It's really about culture and change management," Stephen explains. His team isn't even called developers anymore - they're software orchestrators.
We get into AI governance gaps that keep him up at night, why management completely misrepresents end users, and the translation skill that separates IT leaders from IT workers. Stephen also shares his biggest lesson learned through failure: building exactly what leadership wanted but completely missing what users needed.
The payoff? A framework for earning trust early so business leaders hand you problems instead of solutions. Because your career isn't defined by your technical ability - it's defined by the business problem you choose to own.
Episode Show Notes
Navigate through key moments in this episode with timestamped highlights, from initial introductions to deep dives into real-world use cases and implementation strategies.
[[00:00:00]] Introduction — Basketball needs technology
[[00:01:30]] Origin Story — Programming BASIC at age ten
[[00:03:15]] AI Frustrations — Unnecessary urgency everywhere
[[00:05:45]] Security Concerns — Agentic AI as insider threat
[[00:08:20]] Password Policy Example — Bots know answers better
[[00:12:10]] MSSP Reality Check — Response vs remediation confusion
[[00:18:30]] Moving Away from MSPs — Tools give 80-90% coverage
[[00:22:45]] The Big R — Remediation experience matters most
[[00:26:15]] AI for Sales Training — Building personas from RFPs
[[00:28:00]] Translation Skills — Bridge between business and tech
[[00:32:20]] Salesforce Prediction — Why it's going under
[[00:36:45]] Software Orchestrators — Not developers anymore
[[00:39:30]] True End User Problem — Management misrepresents users
[[00:43:15]] Definition of Done — Alignment prevents casualties
[[00:47:00]] ERP Deployment Reality — CEO vs CTO expectations
[[00:49:30]] Horizontal Capability — IT cuts across everything
[[00:53:45]] Digital Transformation Truth — 90% culture, 10% technology
[[00:57:20]] Building Trust — Problems not solutions
[[01:02:15]] Career Defining Moment — Business problems you own
KEY TAKEAWAYS

TRANSCRIPT
Phil Howard: everyone out there listening to you've been heard. We're talking with Steven Chen and the better half of the technology world. forget basketball, you gotta have basketball and technology, but you can't have basketball without technology. Guarantee it. I guarantee you basketball would not be where it's at without technology. So let's go back in time. How'd you get started in this gig?
Stephen Chen: Absolutely. Yeah. Basketball and technology. I was at a Warriors game a couple weeks ago right. Replays now they have actually replays. That takes it down to the nanosecond or milliseconds to actually truly find. what might be wrong though. So you're absolutely right. Not just basketball but pretty much anything right now. You have technology involved in it. So how I started, it was really interesting. I mean, I got interested in kind of computers was actually in the lab with my dad. So I was probably ten, eleven and my dad was getting his graduate degree. And, there was a couple of computers in his lab and, I don't quite know what that was. And, there was actually another, Elvis colleague in there and, he was doing some research, was doing some computing and kind of show me at that point in time, it was initially, I think it was like x86, like an IBM compatible kind of computer. And, I started doing programming in basic. I still kind of remember I did hello world and loop and it's like, oh, this is actually pretty cool. So, I've always taken a like to technology and computers and, that's really where I kind of got started.
Phil Howard: Okay, this is great. So this comes across your desk when it comes to AI, adoption in your organization, it's not even AI adoption. It's really more AI planning, AI road mapping, AI expectations from C level executives, board members, whatever it is. When it comes to AI, as a CTO, CIO, IT leader in your organization, what is your single biggest frustration, problem or concern?
Stephen Chen: I think at least for me right now, I think there's just a lot of interest and pressure to say, you have to get AI in somewhere and, from before, it's more about, adapting kind of some AI stuff from a user perspective now to eventually you got to have something in your process for automation to not agentic and things like that. I think just unnecessary urgency trying to rush into AI adoption. On the back end of it. I do think that, within a year or so, there's going to be more and more desire to look at AI governance. It's going to look at AI from a security perspective, especially now, people are looking at agentic-AI End of the day, they behave like a user. And one thing I find it's going to be very interesting is how do you detect Agents as for potential insider threat. So we go through a lot of trainings for our employees to make sure that they understand what material or data they're touching, how they behave. But in the rush to get authentic AI to do automation. I feel like there's not enough energy and, rigor spent on how do you secure authentic AI before it? Something catastrophic happens. So that's one thing is you could say it's a frustration, but it's also a balance that I am trying to figure out how to, adopt AI in such a way that we don't put the enterprise and the business at risk.
Phil Howard: can you give me an example of a question that you would look like, is this a good response? Or can you give me an example of what you were talking about?
Stephen Chen: so for example, a very typical one is going to ask you about your password, policy. Okay. Right. And then, right. So, like a security assessment from a client, what is your password policy look like? What's the length? What's the complexity? How often do you change it? who have access? Is there a different level depending on. The access you have and that Right. I know the questions, but I won't be able to know the answers off the top of my head every single time. And a bot will actually give me very accurately what exactly is the policy?
Phil Howard: Like you said this in the last fifty and there's all kind of the same, but not really the same. Is that what you're saying? Like your answer? Yeah.
Stephen Chen: Yeah. I mean, I say a different way. And then the answer kind of evolved over time, right? So like perhaps the complexity used to, include, special characters, words and stuff like that. And then that's one way to look at it. And the other way to say is a lot of company has gone from just password complexity to path phrase to password less. And so having that knowledge base allows me to, explain how our policy actually evolved versus just answering the question.
Phil Howard: Okay, this is great. So like, when I looked at all these different vendors, we ended up breaking it down to like eight different categories for an Mssp, it was like remediation price versus value, like EDR technology, proactive detection, response, speed, security awareness, email security, vendor accountability. Like, I mean, when you go deep into the security assessments, you could get like really deep, like what you're talking about, which is what I really like. Yeah. but what we realized was that. A lot of people in their terms and conditions, this is when we looked at them. A lot of people will say, yes, We guarantee response within, I don't know, fifteen minutes or instant response or whatever it is. Right. And then a lot of clients don't realize they think response means remediation. We are finding how many people think response means reanimation. They think, oh, they're responding. No, that's not no, they're just responding. Yeah. They're not remediating anything. And we've had people that were like, oh yeah, we're and I've just talked with just kind of like on the side in general, they're like, yeah, we're going to go with these guys. It's great. They've got all this, that and that. And I was like, oh, cool, let me throw it through our. Let me throw it through our like, whatever one hundred points, eight hundred categories scored across. This is, which we built like a really long, prompt, right? Like, all these different details and skills and adding this skill and you have all these skills saved. And now we've got this like, security mssp prompt and we've got all these different articles that we wrote and we put that, and then we break it down into this. And what we realized is like, hey, we took those, ten pages of this and that, and we put it weighted up against all of our other guys. And, did you realize that they're not providing any remediation, like at all? Like zero, like zero remediation? Mhm. They're like, what?
Stephen Chen: They just, they just tell you that you have a problem and here's the problem. And then you have to probably.
Phil Howard: See you later. Like, have a nice day. Like I was like, and they're like, no, I'm like, yeah. Oh, like I'm like, it's right here on page seven dot six dot five in highlighted whatever it says, like, which is, that's a simple thing. Like everyone should be taking their T's and T's and putting it into and have a good and this is just the basic stuff. This is just like, right? This is just like stuff, let alone like creating a bot that's going to do different things. Like we have, a few things running on a completely separate machine testing things out. And I was shocked at one of the problems we have is like when we run a Kanban board and we're doing like a scrum thing, right? We might have all these projects going on at one time. And then what's like some of the biggest problems if you have two people that get really excited about a bunch of things. Then you've got other projects going on at one time. One of the things that we found when you have a small kind of niche team, is that people aren't always going into the Kanban board and updating different things. Yep. Or you don't always have your daily stand up meetings or they end up going, they draw on into too long and decide topics and all these different things. So we literally have like the cloud bot thing that's like just constantly going back and forth with people in a, like a special messenger that's like going back and forth and updating the team and everything and then updating the Kanban board, like automatically so that it stays up to date. So then when you get into a meeting, it's like, oh, it's all up to date. And like, now we can actually see where we're at and where. And it'll be like, this isn't. And then like the bot will remind you like, hey, this is not the main challenge right now. We're supposed to be staying on target with like this one challenge, which is like two laser focused, like podcasts a day. In fact, I should probably have it talking to me right now. Like you're going way off subject. You're not even on topic today. it should be talking to me like this, but I'm just that leap over the last, I would say last two weeks, we didn't have that.
Stephen Chen: I see, I see.
Phil Howard: That's how fast AI is growing. And then you got these guardrails and someone else is like, oh, this is gonna be so great. I could use it for our taxes. It could be our own accountant. And then next thing you know, it's like, there's data everywhere and all kinds of craziness.
Stephen Chen: Yeah. So, when I look at you, you mentioned about, mssp very interestingly. I actually moved away from Mssp. The reason why it's a little bit what you're talking about that, the tools that's out there now, kaseya the SolarWinds or Connectwise, they're so sophisticated that you just run those tools. It will give you a lot of information and that you need, right? You have this problem, you have this alerts, you need your patch automated. I'm connected to, to whichever, vulnerability and get it will deploy all that stuff. Now the biggest difference for me for MSP is actually that service level, right? And trying to you mentioned about, well, they, they tell you.
Phil Howard: Yeah, yeah, yeah.
Stephen Chen: So, I'm actually looking for that experience in remediation, that experience when there's actually an issue, how fast can you alert me and how fast matters act on it. Right. And so that's the key thing for me. And then at least for my business, I, decided to move away from MSP and use them as needed basis because these tools is giving me almost eighty, ninety percent of the things.
Phil Howard: what do they really do? They manage all your tools, so you get it in one bill in one place. Yeah. and they kind of do the managing and monitoring, maybe give you like a nice, GUI platform, whatever they want to use to manage everything. Yeah. but.
Stephen Chen: It's actually talking to the people that when you have an issue, you call them up and those people have the experience to say, ah, I have seen this before. We have this in our knowledge base. That to me is the differentiator that you often don't see in kind of like a evaluation criteria, right? Because that's.
Phil Howard: That's on the big R.
Stephen Chen: The big R.
Phil Howard: The big R matters remediation like because if you're a one, let's say because they're actually R one man, it shops out there with a thousand users. Yeah, I see it. There's one guy who's got one thousand. So he's got to rely on an MSP. And then the MSP is going to tell him oh, we can do MSP piece at the same time and which obviously you should not do. but like if you're like a one man shop, even no matter how smart you are, even if you are the best CISO, your CISO, number one, that's at your heart and core, but you're also the CTO or whatever. And an event does happen. You want to be able to rely on someone that's going to remediate that and stop it and cut everything off immediately, like immediate action. numbers and acting nice and speaking nice as a subject matter expert and all that stuff is really, really good. but yeah, numbers don't lie. People lie. Yeah.
Stephen Chen: Yeah. I'll say in addition to the big R remediation, It's also a version or prevention that there are patterns that that can be detected that before you get to the point where you're getting, having started having issues that is start telling you that, hey, you're headed in the danger direction and you should be thinking about those things. so I'd love to always talk to my team that we don't want to get to the remediation where we can, we wanted to kind of avert it or minimize it so that you don't really get to that point. And so that's, you're trying to stay ahead. yes, I also mentioned one other thing for you, Phil, you mentioned that, with, some of the AI stuff, especially from a RFP perspective, miss vendors might hate, how fast AI can actually digest and kind of interpret some of the responses, in my other world where we're actually trying to do sell software, we actually use it from another direction where we built based on the RFP question, we built persona. So for example, for you, Phil, if I go on an internet look for on your LinkedIn profile, I will be able to build a profile for you in AI and then I will actually try to sell you the product that I'm selling. So I'm using that to train my sales team to actually say, hey, you have these, different personnel, here's the role that you play or here's your experience. I'm selling into a university, I'm selling into R&D organization, I'm selling into e-commerce environment. You could build that persona and then have your sales.
Phil Howard: If and only if you actually have like the actual product anyways. Yeah. So what part of your role fires you up the most? Like, what's the real exciting part?
Stephen Chen: Is actually, I think I'll at the highest level, I think this question is related to how also I transition from really a developer to kind of more in the business leader is actually that ability to actually do what I call the translation, right? I know that, in my background, I've been to huge companies and also startup companies and that ability to actually translate a business need and then make that into a technical solution. that's something that I'm always very interesting and then be able to kind of explain it back to the business user and say, how is this going to help you? How is it going to solve your pain? And then when they go, oh, this is it. this is what I really need. And I think be able to be that bridge has always been something that I pride myself in. And it's something that I'm still very much excite me, from a business world, from a technology world, right? I get excited about technologies and I just like to try different things. some of the developer I work with really like that to actually understand what exactly is, a user looking for versus someone translated that into a product requirement or a ticket and things like that. So, that's one. The other I think experience.
Phil Howard: I think I thought of an example, by the way, I think okay.
Stephen Chen: Go, go ahead, go ahead.
Phil Howard: Just because you're in software and we were talking about salespeople earlier, right? So let's use Salesforce as an example. because they're one of the companies that I believe is going to go under with all of the coding. Like this is my prediction. Salesforce will not be much of a company anymore in the future. This is my prediction. I have a prediction that we're not going to need miss whatever side software companies that charge you twenty thousand dollars to implement Salesforce. I just don't think that. But any sales person out there knows that their sales manager is asking them to enter information into Salesforce. And does the sales rep really want to be entering information into Salesforce? No, they do not. Nowadays. It might be different because we have AI. It's probably going to take notes form and enter it. And that's a whole nother discussion from a call center or contact center standpoint. It's going to collect all the information the sales rep said and do it for him anyways. Great. We have solved that problem. That is an AI use case that's actually solved big time, and eliminating senseless calls. That's something that AI agent actually can do very, very well. from a healthcare standpoint, I diverse, so this is kind of like the metaphor for the software engineer, not really understanding what the sales, what the end user needs because what is the sales manager want? The sales manager wants reporting. He wants to know how many calls the sales rep made, how many deals are in the funnel? What's your forecast for the month? All of this stuff does not help the sales rep make another sale at all. But it's important information that they have to enter into sales force. And if they do not enter that into sales force, they will get a demerit or something, I don't know. But if the sales manager was actually delivering and asking the sales rep to do something or give them something that actually helped them sell more deals and do a lot better, and if Salesforce actually helped them do that, which I don't know if it does, I don't think it does other than it helps a really disorganized person, which a lot of salespeople are very disorganized. then in that case, it might actually help them forecast and follow up on deals more and give them reminders and all that type of stuff. But for the, do you see, where am I going? AM I getting it? AM I kind of understanding?
Stephen Chen: I understand what you're saying. I understand what you're saying. Yeah, yeah.
Phil Howard: So a software developer should be thinking about how do we help the sales reps make more sales and what do they really want in this software? Not what is the sales manager telling me I have to build into the software. Yep. Okay. What other examples? anything in the logistics industry or manufacturing or what's another really good example of where you saw where you were like, yeah, we got it, guys. We're not asking the right questions. We're not talking to the right people.
Stephen Chen: Yeah. I mean, so let me address one thing that you just mentioned that software developers are slowly. I don't look at, my software folks as software developers, we start using the term software orchestrators. Oh, I like it. So they're actually orchestrating, they're looking at, how to put requirements in such a way that you could actually feed it directly into the software.
Phil Howard: Okay. Maybe that's better. All right, so let's hit a few more meaty questions. And this is going to be.
Stephen Chen: Let me come back to what you mentioned. I do have an example that you mentioned, Finding out who the true end user are. That's something I feel like I've learned through failures where, in many companies where management, sometimes you talk to them and they represent the users. And this one case where, the leaders completely misunderstood or completely misrepresented the end users that even though as a company, we built exactly what was wanted, what was needed. But when they actually deployed to the end users, it wasn't what they needed. right. And so that gave me a really good lesson to actually ask a lot of questions upfront. so that you actually pinpoint who's actually ultimately going to be using the system and knowing that what they need is actually very important, not necessarily their, representative think that they need.
Phil Howard: Can we role play that right now? Let's fire off some of the questions. How would you dig in? And I bet you you could do the same thing like you did with the security. You could do with this as well. And we could come up with a really, really good. What are your end users really need?
Stephen Chen: Yeah. So, I mean, I start by asking about have you used the system? Right? And, what's your role in the system? And that should tell me about some of the challenges that you are seeing, in the system today. And what functionality are you looking for that it's not there. Now, when you start asking these questions, you start detecting whether or not someone really knows the system or, they're reading from some script or some documents because you'll be able to go in and go, I went into the system, I clicked on this thing and on this page there's that functionality that's not working. And so that's where you wanted to kind of separate the people who are actually, think they know what the system should do versus the people that's really using the system and trying to figure out what functionality, what need they are, or in that case, we're actually building something new. Right. So. you could come from in that case, from an operational perspective, what does your day to day look like? What is your workflow look like? Right? Those are the people that who ultimately is going to end up benefiting from a automation on the system, not the, managers who's looking at, some metrics and things like that. So I think it's actually digging into the kind of daily operation, whether that's actually using the system or kind of their workflow and their pain point that allows you, allows me to actually pull out those key things that ultimately contribute to developing the right solution.
Phil Howard: Okay. What is the definition of done? I love that so much. because it's like, how many times do we start projects and we, don't know if it's done, but we move on to something else and then something comes back and we gotta fix it, or we gotta do something else. And we kind of keep, we have these open loops, so to speak. Yeah. And every time you have an open loop, it creates stress and it creates work and things come up out of nowhere. and I think that that's where really it kind of dies in the soul of it, like It's
Stephen Chen: Important to make sure that you set the expectation and people are aligned on what that expectation, a definition of done that's important. I mean, I'm going through a project right now with a vendor. And in our definition of done is not the same, right? In some, world, that means your time is up, your budget is up. But is a solution truly delivered? It's not So you're so right that, you gotta make sure that everybody's aligned. What does it look like? And that both sides are working towards that.
Phil Howard: if you don't mind me asking, how far off are they on their definition of done and you are off on their definition.
Stephen Chen: Ultimately, right. There's always some financial aspect of things that, I think, the first thing people go back to is really what the cell where the contract says and, then you start interpreting it and, there's some give and take. So in the end of it was that both sides have to give and take a little bit. And our interpretation was even though the word says what the word says, but our interpretation was different. So it does take time and cycle and in this case casualties, meaning that we ended up replacing, some the project manager on the project and kind of bringing a new person and then now we're aligned right now, we literally said, this is what this means and we're going to record it. You're going to transcribe it, you're going to have the transcript. And this is where we're going to look forward, to completion. So, I think we were, I don't, I won't say that we're way off. but we were far enough apart that, everything ended up getting escalated on both sides.
Phil Howard: A realignment call. Yeah, we're going to be on an open. What do they call back in the day? Like an open bridge line for the next two weeks? So, What's the worst this ever that you've experienced? I think that's very important internally as well. So, where does this show up the most where I see this showing up the most is in ERP deployments, right? It's, the definition of done is not clear. So the definition of done to the CEO is different than the definition of done to the CTO, which is different from the vendor as well. So the definition of done for the CTO is well, ERP is deployed and users are using it. We have all the additional add ons and, different deployments and API things that we needed to add on that we said we were going to add on six months later after the first deployment, six months after the first deployment. But after the first six months, the CEO was like, we're done. Awesome. Cross that one off the list and you're like, we're not done. so I think a things. Yeah, this, this definition of done is so important. Okay, what's the most important idea you wish every executive would understand about modern. It or turn to page thirty four. What do most CIOs get wrong that you think is obvious?
Stephen Chen: Would say this, I mean, this is a little bit of my takeaway as well that, whether you're a CIO or, executive, especially in this day and age, don't look at it as a vertical department, but look at it as a horizontal capability that cuts across everything.
Phil Howard: Be smart with the business. It's just my guess. I don't really know. And then, yeah, Zuckerberg, There's something about that video of him, like in his little underneath his bunk bed and he's on his old computer, and his dad comes in, he's he's like, I got in. Or someone is like, I got into Harvard like, oh, yeah, of course. Like I was like, like, I went to school with those type of kids. And to me that the fact that he is, it's just amazing. Like what happens when these people like get control? How are we still calling the department of I t and tell them we've signed off on this new system. We need them to implement it by March first.
Stephen Chen: But I think some of that, challenge we meaning it leaders do it to ourselves.
Phil Howard: Oh, it's our fault.
Stephen Chen: Yeah. That's, I mentioned about translations, right? So, a lot of us gets very excited and we start talking to our colleagues and business side about, see what AI could do for you, cloud all these things. And they're like.
Phil Howard: We need it. But are we really saying like, look, we need it because this and it's going to result in this, and I promise it, or at least some sort of level of growth and not maybe not promise, but like business, like real hardcore business. And I think that's kind of the gap.
Stephen Chen: I tend to agree, right? I think, having the right KPIs or metrics that's again, you, speak to the right stakeholders, whether that's the board, the C level or, operation leaders that having the right metrics that speaks to them is very important instead of uptimes, performance level and things like that's more of a kind of it speak and be able to translate that to say, uptime means user experience. This is how much user experience is going to look like. performance means, your operation team will be able to actually have access to the system all the time that you're able to actually run this report, make your decisions, those kind of things. I think, are very.
Phil Howard: But we expect that that's the bare minimum. Uptime. You better be up.
Stephen Chen: Yep.
Phil Howard: That's why, that's.
Stephen Chen: Why you don't talk about that. Right. So that's why you don't need to talk about that because that's partly my internal measurements. Yeah. But again. it's how does that translate into, client experience? Right? How does that mean that by the system being up, does that translate more into revenue? Does that mean, there's more business coming in? those kind of things that allows, different departments to actually appreciate, uptime a lot more versus it should be up.
Phil Howard: Yeah. And it just goes both ways. It's really about, it forcing that conversation with the executive management of what's really going to move the needle, and being able to coach executive management. We're sitting at the same table. The point is we don't want to just have a seat. That's nice. We actually want to be heard and listened to and respected. Right? well, we might be respected, whatever, but it's like we have a seat at the executive round table. That's nice. How much nicer is it to be heard? So how do we actually be heard? And it's kind of like, how are we teaching? We sit on these meetings. We kind of know what the general the goals are for the year, this, that and everything. But are we really like close business partners with the business and are we asking the right questions to get them to deliver to us what we really need to, build or make happen to move the needle? And it can be very challenging. I just know from my own personal experience, it can be very challenging because there's numerous times I talk about things and for some reason technology guys think that it's this or it's that and it's like a fight, but it could be one little tiny thing, that one little tiny difference that would make all the difference in the world. It's like, oh, okay, you need this in Salesforce and you need this in Salesforce and you need this in Salesforce. Okay, great. But the other I.T. guy asked one better question. Yeah. And he implemented AI to sift and sort all contacts in Salesforce every twenty four hours to see if there was any shift in the marketplace or if they changed jobs or if they did anything within the last ninety days or whatever, and how that would affect a deal in the pipeline or anything. I mean, Zoominfo kind of like, did that, with their like insights and stuff like that.
Stephen Chen: In many ways I differentiate business requirement from technical requirements. And when a user kind of tells you, hey, I need this field or I need this extra thing here, that in some way becomes a technical requirement and that's, limited or myopic, in the bigger scope. I would rather come back to kind of what you said, what is the business objective you're trying to achieve? Let me help you decide whether adding a field makes sense or is there an AI solution out there that will get you there a lot more? so there's that line of kind of trying to figure out when is it a technical requirement that, what I need to get, get it done? Or you ask the question to move it upstream to say, what exactly is a business value or the business requirement that you have. And then let me kind of design that solution. And that could be a form, a field. a report or, some sort of AI thing. in many ways, actually, developers actually like that so that they could be creative versus be told that your job is to create this web page or put this form together. But to say, hey, there's this problem that think through and then let's talk about two or three options and then we'll pick one from there. Or at least we'll start with those.
Phil Howard: I think that's the paradigm shift I was looking for. Yeah, I think that's it. Which is weird because, a lot of business leaders have to be entrepreneurs or very creative and kind of like make something out of nothing. yeah, something, just a quote I remember from years ago, like go out and make something out of nothing today. And yet we're treating the something that we made out of nothing like we're going to just then. Oh, but now we need to buy a product for this. And we feel, to your point, very myopic about how we're going about and choosing the piece like we're not also then sending that same, feeling of, solving this problem and making something out of this problem, over to our team and trusting them to come up with the best way to do it. So what I've noticed is that a lot of times when we force the solution, we're like, hey, here it is. Here's the solution. We ended up with kind of like a lot of broken pieces. Whereas if we actually handed the problem over to the IT guys to begin with, then it wouldn't have had those issues.
Stephen Chen: Yeah.
Phil Howard: That sounds very vague, yeah, so engage your IT team with the challenges and problems and, get them involved early. And we've been saying this for years, but like, it's kind of like, what does that really mean? It's like, don't just give them the solution to implement. I know that sounds dumb because like we've been talking about this forever, but give them the actual problem to solve. But is there anything more to it than that? Is there like a deeper iteration? is there anything there to help kind of bring the two together better? Is there and the end goal is this. and by the way, what we're trying to achieve is this.
Stephen Chen: I would say trust that you built. Right. You have to kind of prove yourself and kind of develop that relationship so that the business will kind. Open up, right. And they will come to you early with the prom and the challenge they're facing so that you could be brainstorming partner with them and that if you're able to successfully doing that, to build that relationship, build that trust. then your probability of success goes a lot higher because now you're actually in a partnership where you're a trusted confidant in saying that, we need you to actually help us solve this problem. I could see based on our discussions, how it is kind of leading and kind of collaborating to actually come up with the right solution.
Phil Howard: And the craziness of all this that may actually eliminate the we have so many projects on our plate right now that we couldn't possibly finish them all by two thousand one hundred. Yeah. Is that right? Twenty twenty? Yeah, two thousand one hundred. Impossible. We have so many projects right now. There is no way. So. And why is that? Because everyone and everyone's throwing something that they think that they need at it, but they're not trusting them with the problem. I need a screwdriver. I need a hammer. I need a whatever this tool is. And you're like, well, what are you trying to do? Well, I need a hole in this wall. It's like, okay, the screwdriver might be right for that. What do you need the hammer for? it's like, who knows? Like, I need to go do this. And you're like, no, no, no, that's not what you you have a different problem. So how does that make sense? How does that eliminate all the different problems? It eliminates all the problems because if you trust it guys to help you solve the problems, most likely you'll trust them with kind of the goals and aspirations of the business as well. And they should be good enough. And I'm hoping everyone listens to this very, very strongly. And I hope I don't know whether you agree or not. Let me know. You should have a good enough environment or a healthy enough environment that your IT team should be able to tell you, I don't think this is a priority for you right now. Because how does this lead to, selling at once. We reach one billion dollars or how does this lead to our main goal of producing two times more widgets this year? We have to solve this other problem first. And this one's kind of like a little side project. And I really appreciate you bringing this here. And I think we could really knock it out of the park, but are you sure you want to do this right now? Whereas do you think I just, if you don't have that relationship going on, then they're just going to be like, oh, we better say yes or we're going to lose our jobs.
Stephen Chen: Yeah, So, I've been at my current company for seven years now and I was brought in to do digital transformation. Right. And, when you think of digital transformation, you think of technology. But the reality is, if I look at eighty over twenty rule or, eighty to ninety percent of this digital transformation effort, it's not really about technology. It's really about culture and change management. How do you change that? Because when you come in and you say, we're going to put in a new system, it might be the right thing to do, but there's going to be a lot of fear, a lot of kind of pushbacks. And so a lot of it is about culture, as you mentioned, that to have a relationship to say, we don't need this, you don't need this. We could help you do something different. And then people are willing to open up to actually have, a dialogue with you to say, I really hate this system. And, but I think if you can help me solve this problem, that's my priority. And you start building that trust, building that relationship. And so I think a lot of my early time with the company in digital transformation is not about technology. It's all about understanding the culture, how to evolve that, and building that relationship so that people understand when change comes along, why and they're part of it.
Phil Howard: Yes. I mean, that's it, that's it. just as a foreshadowing to a future event, AI roundtable is security. And, that like we talked about like, what's your single biggest frustration problem or concern when it comes to AI? And well, we had, Benny Zhang on the show a while back. He's a CIO. And, so he's like, yes, I'm totally in. Let's do it. He's like, by the way, read my new article, Digital Transformation is dead. So everyone out there, digital transformation is dead. Never mind that our community, is a digital transformation leaders. rebranded as you've been heard. Never. It's dead. Anyways, it's good where we're going to welcome AI, re-engineering. So that's a call out to you, Benny Zhang. So if everyone wants to find find Benny Zhang on LinkedIn and read his digital transformation is dead. welcome AI reengineering. let's go. He has, two comments and let's see if we can make it big right now and reshare his article and make it go, big, but he's going to join that roundtable. so yeah, Steven Chen, been an absolute pleasure having you on the show. And, I wanted to ask you, what is that big disconnect between it and, C level leadership? But I think we already answered that. And that is, yes, it's not an us versus them. It's part C level leadership's, trusting it to have those conversations to hand off the, To hand off the problem to them, not the solution. Because maybe it and technology guys that have labs in their house and are very curious individuals that have been playing with this stuff all their lives, might actually get more excited and do a better job when you give them the problem, not the solution. That's going to create more problems to begin with. And then, yeah, it guys, what is it for us? What do we have to change? I can't remember is it we have to like come out of the closet server closet where there were some pizzas under the door to us.
Stephen Chen: Yeah. I think, whether it's.
Stephen Chen: Translation. Yeah. So, I mean, when I look at it, right? So, I know one of the things that we're talking about if you're a aspiring leader, right? I think your career, my career is not defined by your technical ability or technical choice. It's going to be the business problem that you choose to own, right? So I think your technical ability gets you in the room, but your ability to translate business complexity into kind of technical solutions will kind of get you a seat at the table. So, I think if I use that as a takeaway, that's something that, I stand by and something that, even talking with you today, it's very, enlightening to learn and hear from yourself and the community.
Phil Howard: that's mic drop. I mean, that's one of the best quotes I've ever heard. It's the business problem you choose to own. Is that it? Did I get it right?
Stephen Chen: Yeah, yeah.
Phil Howard: That's it man. You got any other great ones? What else are you hiding.
Stephen Chen: From.
Phil Howard: Us? We've been talking for an hour and a half. What are you hiding? What else are you hiding?
Stephen Chen: No, no. Again? Yeah, I think.
Stephen Chen: some of the initial material that you shared, really kind of inspired me and, to actually prep and things like that. But, I really do appreciate the opportunity to exchange and, be part of the community because I know that I got a lot of stuff to learn and there's a lots of great, smart people and great leaders out there.
Phil Howard: Stephen Chen, you've been heard.
Phil Howard: everyone out there listening to you've been heard. We're talking with Steven Chen and the better half of the technology world. forget basketball, you gotta have basketball and technology, but you can't have basketball without technology. Guarantee it. I guarantee you basketball would not be where it's at without technology. So let's go back in time. How'd you get started in this gig?
Stephen Chen: Absolutely. Yeah. Basketball and technology. I was at a Warriors game a couple weeks ago right. Replays now they have actually replays. That takes it down to the nanosecond or milliseconds to actually truly find. what might be wrong though. So you're absolutely right. Not just basketball but pretty much anything right now. You have technology involved in it. So how I started, it was really interesting. I mean, I got interested in kind of computers was actually in the lab with my dad. So I was probably ten, eleven and my dad was getting his graduate degree. And, there was a couple of computers in his lab and, I don't quite know what that was. And, there was actually another, Elvis colleague in there and, he was doing some research, was doing some computing and kind of show me at that point in time, it was initially, I think it was like x86, like an IBM compatible kind of computer. And, I started doing programming in basic. I still kind of remember I did hello world and loop and it's like, oh, this is actually pretty cool. So, I've always taken a like to technology and computers and, that's really where I kind of got started.
Phil Howard: Okay, this is great. So this comes across your desk when it comes to AI, adoption in your organization, it's not even AI adoption. It's really more AI planning, AI road mapping, AI expectations from C level executives, board members, whatever it is. When it comes to AI, as a CTO, CIO, IT leader in your organization, what is your single biggest frustration, problem or concern?
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