You've Been Heard — Teresa Duran

Host: Phil Howard Guest: Teresa Duran, CIO, Tree Top, Inc.

Cold Open

Teresa Duran: If you're only focused on the back office, the fix-its, the incidents, I feel like it's a losing battle, because you'll never get a seat at the table or be a strategic enabler. There are always ways you have to find to get in and help the organization grow. And a lot of that starts with not just the CRM, but their data and insights initiative.

Interview

Teresa Duran: Hi everyone, Teresa Duran. I'm currently the Chief Information Officer for Tree Top, Inc. It's a CPG ingredients firm. You may have seen them in your apple juice and applesauce products. They're also ingredients in a lot of the top 25 brands in the grocery store. It's my fourth CIO role, all in different industries, managing all of IT: everything from software engineering to data and AI to cybersecurity. I'm also a board advisor to a couple of firms and a founding member of the Agentic Engineering Institute. It's basically a company dedicated to helping with this next phase of maturity with AI.

Phil Howard: Super cool. And where are you? Are you in Washington?

Teresa Duran: I am, which I don't know if that's a good idea to say anymore. I feel like we're always in the news.

Phil Howard: Washington the state?

Teresa Duran: Washington the state. Not Washington, DC.

Phil Howard: It's beautiful. So how do we say it, Selah? Selah, Washington? That's where it says the headquarters is for Tree Top.

Teresa Duran: Yeah, the headquarters is in eastern Washington. They get quite a bit of sun out there, on the other side of the mountains. I'm considered a remote employee, so I'm located in Sammamish, Washington.

Phil Howard: Okay. I helped my sister move from Spokane, Washington to Burlington, Vermont years ago. That was back when I was a sophomore in college, so it must have been '97 or something like that.

Teresa Duran: Nice.

Phil Howard: But I remember getting to Spokane and thinking, this isn't rainy. This is desert.

Teresa Duran: Yes. It gets really hot. Where I'm at, there's a ton of rain, but it's gorgeous. This time of year it's really beautiful and green.

Phil Howard: Cool. So here's the thing. We're nearing 500 episodes of this show. We used to be a vendor podcast for a couple of weeks, and then we realized nobody wants to listen to vendors, or listen to someone interview more vendors. So we decided: why don't we interview the people no one can ever get to? The ones behind the gatekeepers. You probably have a gatekeeper who forwards people to voicemail. Why don't we speak to the people who are actually important? So we started a little weekly podcast to interview all the people I love working with, which were IT leaders.

Well, who are these guys anyway? They're kind of nerdy. They probably grew up in a time when there was no position for technology. And they've got to be popular, because most of these guys hide in the server room. Or girls, a small percentage. So let's dissect them. We used to be Dissecting Popular IT Nerds. And then people asked, "What are you guys doing? You're just dissecting popular IT nerds?" No, no, no. We actually know a lot about technology and do all kinds of stuff.

And what we found out, after 420 episodes (we're at 480 or so right now), was this amazing thing. I think you'll agree with it, and I think everyone else knows it: nothing gets done in any company without technology touching it.

Teresa Duran: Yes.

Phil Howard: Big aha moment, right? But here was the thing. We hired a great branding guy, the same guy who branded KnowBe4, if you know that company. The security training, email phishing company.

Teresa Duran: Yes, everybody knows them. They make you click on things.

Phil Howard: So I brought in David Breyer to help us after we'd been dissecting popular IT nerds forever. And what we discovered was this. It's great to have done all this work: putting out fires, the late-night patches, the ransomware attacks. Some of you still have IBM AS/400s running things in the back room. People have old IT silos everywhere. When everything's on fire, IT is invaluable. But when everything's running like a well-oiled Tesla, you're a cost center. So how much nicer would it be to have a seat at the executive round table, and also be heard? So we've started the revolution of You've Been Heard.

I want to open it up and give you a few minutes to talk about that: how things have changed over time and how you're using technology as a business force multiplier. You have this thing called Geekinese, and I'm assuming it has something to do with translating hypervisors into something that can be digested as ROI, the things business leaders actually care about.

Teresa Duran: Yes. So here's the thing. In each of my CIO roles, I was hired to help the organization go through its extreme makeover, the largest transformational change in its history. You may ask why. A lot of organizations reach a point where they've been trying to transform, trying to do many things, trying to modernize. But they had a really difficult time, because it's always about people change, and they were bypassing technology leaders. I describe it like this: everybody's trying to get to the prompt era today, but they're still purchasing software and solutions like it's the CD-ROM era.

So what ends up happening is people look for leaders who will help them connect the dots across the enterprise, see the opportunity and, like you said, have a seat at the table. I mentioned to Gabe when we met last time what I'm up to. A lot of what I do is help folks with translation. There's Geekinese, which is the geek talk. You could be the most brilliant person in the room, but that won't get the results you or the organization need. They need somebody to translate complicated concepts into: How is this going to help you grow your company? How is this going to help you reduce risk? How is this going to help you drive efficiencies? The ability to translate that opportunity is the reason they need us. And it's not just having a seat at the table. It's what you do differently once you're there.

I'm actually in the process of writing a book about it, because it's such a fascinating time right now, when you think about how many transformations fail, and AI initiatives today too.

Phil Howard: Do you think we do a bad job training IT and technical folks at the beginning? It's like grammar school. Is it still called that? I was kind of old in grammar school. I used to walk four hours with a sack on my back to get there. And I remember that, all the way through college, no one ever taught goal setting, personal mission statements, values.

The point is: do we do a bad job teaching technical people from the start that they need to learn how to translate this into business? Or is it mostly, "How many YouTube videos can I watch to get my Cisco XYZ certification, or whatever CISO certification?" It's all super nerdy, and there's never anyone saying, "By the way, you're going to look like a real jerk, and really arrogant, when you speak to a high-level CEO, whose entire job is to make the company money, in a way that makes him feel dumb." He knows he's not dumb. It just makes you look arrogant.

Teresa Duran: Yeah, they look arrogant.

Phil Howard: And here's the worst part. Then you let the slick vendor come in with some ridiculous demo, because they knew how to talk. And you know it's not going to work in your environment.

Teresa Duran: I think you're right. A lot of people spend a lot of time just loving the tool talk. What tool do you use? What certs are you going after? Lots of acronyms. Each time I led a new department, I liked to get to know the team and find out what they were learning. Part of it is whether they're going after certifications and growing technically in their discipline. But some people stop learning, too, because they've been at the company so long. They become comfortable and complacent. I can't tell you how many people loved their on-prem environments, including on-prem email, not that long ago. And I said, nope, we're moving to the cloud.

Phil Howard: Migrating people off Exchange is still a thing.

Teresa Duran: It's a thing. And here's the problem: who ends up in the hot seat? It's not just your head of IT. It's also the salesperson when email is down. And I don't think it's just about translating up and out to VPs. It's translating to your own technology department. Are you creating a compelling vision? Are you explaining what it's going to do for their careers? Forget the here and now. Where do they want to be in a few years? It can't be, "I'm comfortable with on-prem email, and I know I can do this until I retire." The challenge is getting them not just to learn translation, but to keep learning and growing. You're seeing that same resistance with AI, from people who were comfortable with old software development practices.

Phil Howard: Do we want to go down that hole? I have a split group of friends. One group is the software dev crowd, and they might as well be Cheech and Chong sitting in a room somewhere: "Yo man, forget this AI stuff. You're crazy, man. No one's gonna do that. People are gonna die. You can't do AI in healthcare." That's one extreme. The other extreme is, if they don't grab on, they're done. I'm somewhere in between, seesawing back and forth.

I don't even know where to begin with that, so I'm not going to go there yet. Let's finish the translation piece first. Do you have any frameworks, or very simple steps? If there were three steps you'd give someone to translate for the C-suite, to really gain someone's ear, to get a seat at the executive round table and be heard from day one... What's the key to being the first slide in the deck, not the last slide at the end of the company presentation: "By the way, we have time for IT to announce that we're zero trust certified now"?

Teresa Duran: That's a good question. Gosh, I could talk for hours on this. Number one, if you want to keep it simple, ask yourself: what's the history? Why didn't you have a seat at the table? What happened? What went wrong? It's not always a technology issue. Often it's a leadership issue.

When you're making a specific ask of a leader, did you time it right? Did you make the ask up front? Are you making sure they don't feel cornered? You may have to spend some time with them, because they won't want you to read them a deck or a memo. Maybe they'd rather have a conversation, and you listen to figure out what drives them, what matters most to the company, and where you fit in.

There are also simple learnings along the way. I have a tried-and-true 90-day playbook: how you walk into an organization and do the blitz. Some of it is managing up. You explain what a modern IT department looks like. Here's how we should be engaged. Here's how we should fix the governance process and the rules of engagement for architecture decisions and big purchasing decisions, plus how you approach vendor management, talent management and so on.

And do you have a top five? I'm a big fan of that. I walk into so many organizations with a huge laundry list of projects that never got completed. Five years of roadmap that just rolled into the next five. So what are you doing differently to simplify? Everyone has too much software. Everyone has too many things on the list. How do you zoom out and get to that top five?

A lot of that comes down to building your leadership team. I feel really strongly about having the IT department run like a symphony, where everyone knows they're needed. There are a lot of cross-dependencies between areas. Are you playing to people's strengths? Do you understand the priorities? Are you balancing innovation against cybersecurity risk? How are you enabling and advocating for what's best for the organization, based on what your team is going after?

I was on a leadership call earlier today, and I said (maybe it's not appropriate to say) nobody wants to be that Leeroy Jenkins guy from World of Warcraft, who runs out in front and causes a bunch of havoc. What are you doing as a team to stay aligned with that top five and build around delivery? And how are you helping shape one voice about where the opportunity is for your department?

Phil Howard: Okay. You're in the 90 days. What are the key first questions you ask executive management, the C-suite, all the different departments, so you can align your symphony?

Teresa Duran: That's a really good question. Number one, you look at whether they have a compelling company strategy already in place. And not just a one-slider that says, "We're doing these few things." Does it go down to the next level? Is there an operational plan, or key initiatives that are top priority for the company? Where a lot of technology departments struggle is this: did you build your technology strategy and roadmap around the company's vision? Is it based on where the company is headed? Were you agile enough to adjust when it changed? If not, you have to take a step back and figure out why.

So understanding the company strategy comes first and foremost. But I'm also someone who likes to get into the weeds. I have offline conversations to find out where the opportunities and pain points are. What's not being delivered that you need to run your part of the business? I like to see demos, from different viewpoints: not just the end user's or the department's view, but our own team's as well. How painful is it to manage? Do we have help desk tickets where 80% of the problems center on a couple of systems? Where's the organizational noise and friction, in supply chain, in operations? If we consolidated or modernized systems, what could we do differently?

I also like to look at the reports people use and the decisions they want to make. That gives you a blended view. Do we have the right enterprise architecture? Do we have the right talent? If you're new in the role and going through a huge modernization, you'll have a finite budget. Do you have the talent you need, or do you need external talent or skills, through vendors or a restructure? Those are all key parts of the 90-day plan.

And then the cyber side, where I could go on and on. I like to get into the weeds on everything from your insurance policies to audit findings and any recent breaches or events. What's on the top of the risk register? What do we need to do to protect the company and the brand from cyber threats?

Phil Howard: I'm fascinated by a bunch of things you said. One is the roadmap that's been sitting around forever with a bunch of projects that never got finished. That's a common theme for a lot of people. "We have 25 projects. There's no way we'll ever do them. They'll be done in 2050, and by then none of it will make sense." That's why you see a roadmap with all that stuff on it.

And the common thread is that IT has been used as a hammer for however many years, instead of bringing key stakeholders to the table first, finding out the actual goal of the business, and then applying IT to it.

Has IT primarily been a fix-it department? And I don't want to say "department," because everyone hates the idea of the department of IT. We're not a separate entity. We're all the company together. So where's the paradigm shift for the modern IT leader? Is it fixing things, modernizing, streamlining? What about scaling the business? What about having a business mindset and applying technology as a business force multiplier? Have you been the hero, where you saw something the company wasn't using and applied technology to grow the business, rather than just optimize it?

Teresa Duran: Absolutely. That's where I've focused. In real estate, I was at John L. Scott. After that, Make-A-Wish, also on the growth side. And then CorneaGen, a biotech firm. In each of those three roles there was a heavy emphasis on helping with CRM and marketing capabilities, as well as growing the supply chain.

If you're only focused on the back office, the fix-its, the incidents, I feel like it's a losing battle, because you'll never get a seat at the table or be a strategic enabler. There are always ways you have to find to get in and help the organization grow. And a lot of that starts with not just the CRM, but their data and insights initiative.

Think about what matters most to these executives. What are they trying to do to run the business, and what information do they use when they look at growth? Everything from their go-to-market strategy. It's good to have those deep dives. That's where you have conversations with the VPs and the CEO, and ask not just how things are going today (there's a reason you may not be in the room) but where they want to take the organization.

Maybe they have a strategic play for growth. At Tree Top, for instance, our plan is to grow a lot more in the East. How do they envision doing that? Do they have a go-to-market strategy? What are they doing with partners? How are they looking at their pipeline and opportunities from a probability perspective? And how does that turn into revenue forecasting that informs the supply chain, so you can grow as fast, and as well, as you can?

I believe those deep dives and conversations matter. But you also have to back them up. Do you have the talent to build these things? Even with great vendors in play, all of us know someone on the FTE side has to know how to drive and translate. You can't let vendors run loose. That's where companies run into trouble: they were too hands-off, and they ended up relying on fragmented point solutions instead of something that will really grow the enterprise.

Phil Howard: Give me an example.

Teresa Duran: Think of shadow IT. A lot of organizations today work with an individual vendor on an individual solution, and then their data isn't actually stored within the enterprise. When you think of sophisticated insights, whether it's revenue growth, marketing campaigns, your event strategy or B2B, if you only use a third-party firm (and I've seen this many times), the data is sometimes housed outside your company. So you can't do any sophisticated analytics. You can talk about AI and advanced analytics all you want, but the information is dispersed.

That's one of the things I always think about when it comes to how a technology department becomes a true strategic partner and enabler: what are you doing with all the information? Forget the platforms and tools we all love to talk about. What are you doing with the data to help the organization make better, more real-time predictions with the information at its fingertips?

Phil Howard: What would you say is the most important thing to never outsource?

Teresa Duran: You know what? I actually believe some things should be outsourced. I'm a big fan.

Phil Howard: No, I am too. I believe a lot of things should be. It might even be the opposite of what people expect. Maybe it's "never outsource your advertising..."

Teresa Duran: Correct.

Phil Howard: "...but outsource security." And you might say never do that. I just want to hear your take.

Teresa Duran: There's a balance, and that's the thing. Between my four CIO roles, I spent one stint in consulting, a lot of it with the big tech firms and others. For me, the outsourcing conversation always depends on the industry, the size of your team and your budget constraints. Where's the sweet spot where an outsourcing firm will do well? And when I think of outsourcing, I also mean vendor partnerships. I don't believe any IT department or IT leader succeeds without strong vendors, period. I always have a handful on my short list anytime I'm looking to do something.

Phil Howard: Yeah.

Teresa Duran: But I do believe internal talent needs to be in place to make the symphony work, for accountability, or what I call keeping the tree alive. A lot of times a vendor comes in, implements something and leaves, and then nobody knows how to do anything with the system. We all have one of those in our environment today. It's the same with employees. You might have key-person risk.

Phil Howard: Yes. "If he leaves, we're done."

Teresa Duran: And that's what's happening with AI. A lot of people are saying, "I can vibe code, I can build something." Okay, but you just created something that's just as hard to support. Who's going to support it? Whether it's an Excel sheet or something you vibe coded, somebody has to keep it alive. So when you think of total cost, where's the right mix?

With financial systems, sometimes the upgrades, patches and updates are predictable enough that you can use a good firm to keep them going. But for something dynamic and constantly changing, you need at least a mix, where internal talent knows what's going on too, so they can keep up with the strategy and stay a step ahead of where it's going.

Phil Howard: Please come to the AI Roundtable on Wednesday. Here's the thing. A lot of people are going to implement AI and build something with it. It may work, and it may be great. Then a month later, the model changes. Something happens.

Teresa Duran: Or the person who built it leaves.

Phil Howard: I'm terrified of you leaving, Greg. We built a serious setup with agents and everything. Then Claude, or whoever, decides one day to change how the APIs work and how tokens are spent across the platform. And there it goes. We're small enough to be nimble and change things. But what if you were the Titanic? What if you were a big manufacturing company that really bet on one area of AI? To me, that's the argument for point solutions. Little AI things that work. A small point solution can make a huge difference.

Teresa Duran: And we just saw something in the news about Microsoft trying to reduce how much its employees use Claude, because of the cost. They also want to use their own internal tools, but it was just too expensive. So it's always about where the value is in your technology investments, and how you optimize to deliver the most value and impact to your company.

When I think of point solutions, I think: instead of buying seven disparate systems, could you have gotten away with three? How are you driving for simplicity in your enterprise roadmap? I can't tell you how many companies have five systems that do the same thing and could consolidate to one. How are you simplifying your architecture where you can, to drive better data outcomes too?

Phil Howard: I see it all the time. People with a hundred locations getting a hundred bills. Why? "Well, mergers and acquisitions. We haven't gotten to it yet. We're in the middle of the ERP forklift, so I don't even want to think about that." I'll do it for you. "No, no, no, we can't." There's a lot of that.

I've seen a massive healthcare organization on the East Coast, from Florida to Maine. Well, maybe not that far, more like South Carolina to Maryland, maybe higher. Three hundred fifty locations and 250 disparate phone systems. The IT director had been there for 25 years. I asked him, "What do you use for email?" What do you think he said?

Teresa Duran: Lotus Notes?

Phil Howard: Lotus Notes. On-prem.

Teresa Duran: Wow.

Phil Howard: And that was only about eight years ago. It's still 2018 there. It was ridiculous. I still love telling that story. It never gets old. People say, "What?"

Your job is very stressful. There are a lot of moving parts. Back to the You've Been Heard theme: the IT roadmap is like something out of Indiana Jones, covered in dust, with the boulder rolling across it. Here's the roadmap with all these projects on it. As a business owner, and also as someone in technology, I know how many things I want and how many things I think we need. But the right technology person will say (and this may be the heart of what you're talking about) that it's not a technology question. It's a solution question, a challenge question. What are you trying to do?

Teresa Duran: Yes.

Phil Howard: What are you trying to solve with technology? Did it just land on your desk because the sales rep from so-and-so took you to the ball game and talked about how agentic whatever will do this, this and this? How does that apply to your main challenge right now, which is selling more Tree Top apple juice? Apple juice sales are down 1%, and we need to raise them 2%. How does that help? Because the answer could just be a Facebook ad, and all of a sudden you're booming. And we use AI not to write the ads, because we've got better copywriters, but to place them, because it's more efficient. Something like that. My weird imagination just came up with Tree Top, apple juice and Facebook for some reason. But does that make sense?

Teresa Duran: It does. And that's where IT is a strategic enabler. In those conversations, talk less about platforms and tools and the laundry list. Can we tie it directly back to what the organization needs most? How are the CEO and the board measuring the company's performance?

Phil Howard: We have to be business leaders.

Teresa Duran: Yes, it always starts there. It's less "we need to upgrade the systems" and more "what is the company trying to do? What's right in front of us?" That's why (and it's probably still an unpopular view) I don't really believe in five-year roadmaps. Things are changing so dynamically that you have to think about what's best for the next three to six months.

Phil Howard: What's the agile thing we should be able to knock out? What's our 90-day plan with two-week sprints?

Teresa Duran: Exactly. And how are you tying that back? How are you communicating, marketing and selling the opportunity? If you see something that isn't on the list but should be, are you spending enough time getting in front of it, so you don't have to wait for a crisis to do something about it?

Phil Howard: Please, no crises. That brings me to my next question. Tell me about a moment in your career when there was a crisis and you were the hero. If you and your team hadn't been there, everything would have come to a crashing halt. The business would have been on fire. I'd love to hear your war story, whatever it is. There has to be a moment where, if you hadn't been there, a lot more people would have cried.

Teresa Duran: Nice. Well, maybe I won't bring up the cybersecurity incidents. I'll go with something more heartwarming.

Phil Howard: No, we like fear and doom and gloom. Sometimes I ask this and get, "There was this horrible ransomware attack right after I came in. It wasn't my fault." And I ask, "Well, what did you do?" "We paid the ransom." Honestly, sometimes that's the answer.

Teresa Duran: Yes. But then it's: what are you going to do differently? Are you going to mitigate the risk? Because you can't just make it go away.

One of my big career wins was at a biotech firm during the COVID year. I joined right before COVID, and we had an accelerated timeline to build a custom HIPAA-compliant solution. It's an incredible story because there were so many impossible odds. You had to deliver custom software within a matter of months. They didn't know whether we'd build or buy some of the architecture. It ended up being a blend.

What made it so complicated was that I joined with the expectation that the company would go through an IPO. So everything seemed amazing. I was excited to be back in biotech and pharma. I spent over 16 years in that industry, and I love it. The plan was to help the organization put the necessary changes and controls in place, and then grow.

We also had an incomplete acquisition. Like you mentioned earlier, I'd walk into rooms and hear, "How come we can't talk to so-and-so?" Part of the company was on old Skype instead of Teams. It was foundational stuff. And you can predict what came next. A couple of months later, everyone went home and worked through COVID remotely, in the middle of a transformation. A huge change.

The company was going through a lot of hard times. Elective surgeries stopped or were dramatically reduced. So the organization was furloughing people while we were burning the midnight oil developing custom technology solutions.

Then, in the middle of all that, instead of an IPO, we were guiding the company through a divestiture. We were helping break up the company. Imagine the challenge from a technology perspective. You think you're all rolling in one direction, toward growth, the exciting part. Instead, the company is dealing with uncertainty and change, and you're helping it through a breakup while rolling out huge transformational software.

And we couldn't disrupt the supply chain. Some states were open, some weren't. We were shipping corneal eye tissue with a 14-day window, even to other countries. So we couldn't just roll things out and let them sit idle. There were times I wondered if it was just impossible. You have to keep your team motivated through all that uncertainty, while people everywhere else were quitting or frustrated with COVID.

But somehow we all pulled it off. It was actually an amazing time. And it wasn't just that we were amazing. It was the alignment with the CEO at the time. Imagine the wild swings in direction. You're going IPO. Nope, you're going to finish this acquisition. Then you're going to break the company into three pieces. And you're still going to build the custom software. There were also some potential legal issues around the same time. A lot of moving parts.

It was the alignment with the CEO, the technology team and all the department VPs. It was remarkable how fast everyone embraced the changes in direction, several times over. We accelerated what would normally have been a three-year roadmap. Separating data centers, separating applications, separating financial systems, and still building custom software. We pulled it all off within a year. I don't know if I'll ever repeat something like that again.

Phil Howard: I hope we don't have to repeat that.

Teresa Duran: I know. I'm getting too old for that, I think.

Phil Howard: Now the other side. What about when everything's running smoothly and IT becomes a cost center on the spreadsheet? How do you make sure your work is still seen, still valued, and that you're still heard? Not that IT is ever perfect and we're sitting back with our feet up on the table. But there are times when everything's in place and running. What do you do then?

I always liked startups, fast-growing companies, places where I could make a difference. I have a friend who's a VP at Comcast. We started out together years ago, and it's the daily grind. I just couldn't do that. So say you're at a well-established company, IT is running fairly smoothly and it's seen as a cost center. How do you make sure your work is still seen and heard, and differentiate yourself?

Teresa Duran: Gosh, that's an interesting question. I feel there are two types of CIOs: the ones who love the extreme makeover, and the ones who are comfortable with iterative change. I'm the former. I love the huge, wild changes, like renovating a home.

Phil Howard: Maybe that's why I keep moving. My wife says, "Can you stop moving? Why do we keep fixing up houses?"

Teresa Duran: It's fun to build. I love helping organizations see dramatic change and the benefits they can get from technology. That's not to say iterative change is bad. But if you're in that situation, you have to keep yourself on your toes.

With technology moving so fast, the lifespan of companies is shrinking faster than ever. I was reading about that not long ago. It's all the disruption, and not just AI, which is a mix of great opportunity and hype. There's an explosion of new software companies and a ton of competition. You've got headwinds: tariffs, the war, other macroeconomic conditions.

So companies really need technology leaders who are constantly asking: What's next? What's around the corner? How do we keep up with our peers? What opportunities are there to help the organization? What should the company be learning or exploring? Don't get comfortable. Even if your team is doing well and comfortable, the company can't sit still. It might not hold up against competitors over the next five or ten years. So how are you helping it embrace change, adjust and see what's possible with technology? I don't think you can ever get comfortable.

Phil Howard: Okay, then what's your prediction? Eighteen months from now, what's going to be different? I listen to some wild stuff. I'm a huge Alex Hormozi fan, and I was listening to him the other day. I actually tend to agree with him. I'm a glass-half-full person. I'm not the Elon Musk "AI will be the death of us all" type. And I don't think there's anything we can do to stop it.

But Hormozi said this crazy thing: AI is going to get so good at replacing people's jobs that it becomes a pathway toward a kind of utopia. Work becomes all thinking, creative, human work, and a lot of manual work just isn't done anymore. Maybe there's even no need for money. Sounds crazy, and to me that's way off. But AI might be the path toward it. In 18 months, though, what do you see being a big difference, especially on the IT side?

Teresa Duran: I'd still say save your money and invest. Okay, I have a few of these, because I've thought about this question a lot.

Number one, everyone is going to realize they need Gen Z. They can't just stop hiring entry-level people, because those are our future leaders. A lot of companies are going to regret it and ask, "Why weren't we hiring and investing there?"

Phil Howard: I don't understand that problem, though. Are people really not doing that? Am I just clueless? I'll hire anybody who's great at what they do.

Teresa Duran: What's happening is that a lot of people with zero to five years of experience are struggling to get jobs. That's why so many CEOs are getting booed at graduations. They're talking about AI being the future, and then there are no jobs. So there's a bit of panic there.

I have a strong opinion about AI. I'm the Goldilocks. I don't think we'll reach a point where no one has to worry about money. I also don't think it's all doom and gloom. But I think people will look back and ask, "Why were we treating this moment like Y2K?" You remember the Y2K days: a hard deadline and a frenzy to get there. Why are people treating AI that way? Organizations still have messy data foundations. They don't have the talent. They can't afford it. And everybody's running around saying you have to build with AI.

All the vibe coding shows that yes, you can automate some things. But did you do it cost-effectively? Did you generate an ROI? Should people stop learning it? No. But I don't think it should be the mass panic we're seeing today. I don't see massive organizations going all in on a few vibe coders, because it could be disastrous.

Phil Howard: It's that MIT report, right? Ninety-five percent of AI projects fail. And why?

Teresa Duran: Correct. It's huge. But I was going to say, in 18 months I think some companies will give the SaaS companies a run for their money. There's so much venture capital going into AI and SaaS products, and some of them are pretty amazing. I was playing around with Odoo over the weekend, because my senior director and senior developer said, "You should test out Odoo. We should consider it versus some of these other SaaS products that just cost too much."

At first I thought, well, it can't replace an ERP yet. Somebody's got to keep the tree alive. But there are certain problems it can solve cost-effectively. How many Odoos are out there right now that can handle AI-driven back-end processes and take away some of the friction of hosting? They solve real problems and optimize cost. How many of those are out there that we aren't thinking about, that could provide incredible benefits?

Phil Howard: So many.

Teresa Duran: Exactly. So in 18 months you'll see rising competition, and some amazing new offerings that give a run for their money to products we're all used to but are paying outrageous fees for. I also think, with Amazon and the other platform companies, people are starting to think beyond multi-cloud, about how to optimize costs and rely less on some of these platforms. People will keep experimenting and figure out what's best for them.

Phil Howard: Let me play Big Brother here, because one of my first thoughts was, "Salesforce is done." We vibe coded our entire CRM exactly the way we wanted it.

Teresa Duran: Yeah.

Phil Howard: In a weekend. And then I thought, wait a second, we went too far. What if Claude changes its token pricing?

We used some bolt-on applications, point solutions if you like, to do things our CRM doesn't do natively, things that are pretty specific to a podcast. How do we recruit people? We recruit IT leaders on LinkedIn. We want to find the perfect IT leader who fits certain criteria. Here's how we search for them. And I want to track that. No CRM is going to track that kind of odd activity: how we search Sales Navigator, how many pre-podcast calls we do to filter people before they come on the show.

One thing I've found is that a lot of CRMs don't track activity well. In Salesforce you can add modules that track phone calls and so on, but not in the visual, whiteboard-style way I wanted. I want to know how many invites you sent, how many DMs you sent on LinkedIn, what you said in this one versus that one, how you're split-testing.

And my producer, who's our AI genius, is so far ahead it's laughable. I don't even know how to catch up. He said, "All right, I'll build it." He built it over the weekend, and the next day it was: here's Pulse, all in one application. It's already mobile. Here's all your activity. This person was on the podcast. Here's where their show page will be. Here's their link. You can follow up, all in the app. And I thought, Salesforce is done.

Teresa Duran: Incredible.

Phil Howard: Then I realized how complicated it is to build a Salesforce. And I started thinking Salesforce will be smarter than that. They'll start paying the LLM companies to raise token prices, or buy a model outright, or something. They'll do something to control the market, because that's how capitalism works.

Teresa Duran: And I think they'll figure out how to integrate more seamlessly where needed. What made Salesforce successful (and I've been involved in company-wide implementations for a long time)...

Phil Howard: Yeah.

Teresa Duran: ...is not necessarily the core CRM. It's the whole omnichannel piece, the campaign management and its effectiveness. If you can build that on your own, that would be incredible, if you could truly build all the connections across all those channels.

Phil Howard: For us it was also that we're primarily a LinkedIn podcast. How do we collect everyone's social handles? How do we post? How do we reshare? So much of it was half enterprise. We're an enterprise podcast. We live in a strange in-between world, halfway between business-to-business and business-to-consumer. What we need, we kind of have to build ourselves. AI enables that, but it also creates new problems, because it changes so fast. I think that's going to be the biggest problem: how do organizations that have to adopt AI adapt to AI itself changing?

Teresa Duran: That's the one thing I notice. I always say: just because you can build something doesn't mean you should. A lot of it is how you're going to adapt to all the changes, including your own people changes, and what the easiest, most cost-effective way to do that is. But yes, about Salesforce, I have to admit I'm hearing that quite a bit lately.

Phil Howard: Remember when email died? How long ago did email die as a way to actually reach people? It's almost impossible now. Back when email was alive, we threw junk mail in the trash. "Take my name off the list." People's phones were ringing: "Take my name off the list." Do people even pick up the phone anymore?

Teresa Duran: Yes, they do.

Phil Howard: Not as much, with all the other marketing methods out there. But I eventually realized it's sometimes faster to send a CTO something in the mail. If someone's really important and I want them on the show, it's easier to send a physical piece of mail than to email them. Email goes into Barracuda or wherever. Forget about it.

What if you could go back to day one of your IT career and tell yourself one thing, knowing what you know now? What would it be?

Teresa Duran: Don't pick a company for its logo. Pick a company where you can make the most impact and where you'll learn. I have a nonlinear career. I got a degree in chemistry and started out as an analytical and organic chemist, then moved into IT. It's really important to weigh tenure against the question, "Am I learning something new?"

You're seeing so many people lose their jobs. It reminds me of my pharma days, when I left the industry for completely different industries. I wanted to be more recession-proof, but I also wanted to get uncomfortable and learn as much as I could. That's what will help people stay marketable in the long run, unless they have an amazing company they think they can stay with for a very long time. And that's really hard to do these days, with all the change and pressure across industries right now.

Phil Howard: I used to ask this question a lot, and I haven't in a long time: what's the end game for you? Almost nobody has ever given me a satisfying answer. It's usually, "I'm just going to keep doing this until I die." I think that's because, if you asked every guest across all our shows for their number one value, without a doubt they'd all say curiosity. If you asked what the number one trait of a CEO is, nobody would say curiosity. In IT, they always say curiosity, which is interesting.

Teresa Duran: For me, I just love learning.

Phil Howard: If you love learning... I don't think I've ever had a chemistry major on the show. I've had biopharma people. There probably has been one and I'm just not remembering, because it's hundreds of episodes, and there are four other hosts on the show. But usually everyone came into IT by accident. Is that true for you? How did you get into it?

Teresa Duran: Yes. I worked at Pfizer, and they needed one type of geek to talk to the other type of geek. I worked in a lab, I was helping out with databases, and I actually enjoyed it. I just wasn't excited about the lab work. Every day you go in and it's a lot of the same stuff.

Phil Howard: Micropipetting. I was a chemistry major for two years in college, and then I dropped it. Everyone in my family is a doctor. "What are you going to major in?" It was biology, chemistry or engineering. And I said, nah. You can't be a doctor just because everyone else is. It's too much work. You have to be diehard. Inorganic chemistry, studying valence electrons, was enough for me. It was exhausting, and I was done. But I know enough to know that working in a lab, or in biopharma, can get pretty repetitive.

Teresa Duran: My original plan, of all things... I went on a game show in college because I wanted to get a PhD and I was a broke college student. I didn't win any money, so I thought, well, I'll go get a job. And I ended up as an analytical and organic chemist. I loved working in pharma. I just got bored with the monotony. At the time, the technology leader needed someone who could translate geek to geek. So it was, "Do you want to work in IT? Help us build out custom software and projects, as someone who knows how to talk to the other types of nerds in this company." That's what started my career in technology.

Phil Howard: I'm looking at your career timeline right now. We both worked at Starbucks. Something like one in four people have worked at Starbucks at some point.

Teresa Duran: That's funny. Were you at headquarters?

Phil Howard: No, no. I graduated from college, got married and needed a job right away. Starbucks said, "We need store managers. We'll pay you a salary." So I was a store manager, then I did asset and security protection, then training and developing other managers.

Teresa Duran: Nice. That was my break from pharmaceuticals. I got relocated to Washington, and I thought, okay.

Phil Howard: TEKsystems. I've worked with them somewhere in the past. I can't remember where.

Teresa Duran: They're on my short list. I absolutely love them as partners. They're amazing.

Phil Howard: I'm trying to remember when and what I was doing with them. It'll come back to me. You've got a nice list going here.

So many people say curiosity is their number one trait, but what's the end goal for you? Do you want to sail off into the sunset? Do you believe in retirement? Because I think it's a farce. It's a lie that we're going to live out these golden years at seventy. I've seen it with all the doctors in my family. They're living out their years remembering that the glory days were when they were doctors working ridiculously long days.

Teresa Duran: Long days. My husband says I can't plan to retire anytime soon, because I'd drive him bonkers at home.

I think other IT leaders are probably saying this too: I'm really enjoying supporting boards right now. I'm a board advisor to a couple of firms. One is SullivanCotter, which offers services and a SaaS product tailored to the healthcare industry, which I absolutely love. I'm on a committee with a group of physicians, and it's wonderful, because the conversations are always about how to improve healthcare outcomes.

Phil Howard: I've been asked to join boards before, and I always wonder, do I have time for that? What's the time commitment?

Teresa Duran: The first couple of years were a lot heavier, because you're ramping up and onboarding. So if you're new, I'd expect to spend more time. Right now we meet four times a year minimum, but I always try to do extra if they want to meet offline.

I'm also supporting a cybersecurity firm called Agency. They provide GRC solutions, and they do a lot to help startups that want to go public get their compliance in order. They also provide cybersecurity services. I probably meet with them about an hour a month.

So it's not a huge time commitment, but I find real joy in it, because you're helping other companies with anything from their go-to-market strategy to partnership opportunities, scaling or talent management. I'm having a lot of fun, because it's not just about technology. It goes back to how these companies think about growth, differentiation and scale. A lot of technology leaders can do those things too. The conversations are more sophisticated, without the pressure...

Phil Howard: It's more collaborative, I guess.

Teresa Duran: ...and without doing the same things over and over. I think that's what happened in my CIO days, when I took a break and went into consulting. It felt almost like the definition of insanity, doing the same things over and over. Nothing surprised me anymore. I thought, if I'm going to do this again, I have to be part of helping an organization grow and do different things. I think AI helps with that. But I don't want to solve the same problems over and over.

Phil Howard: Why does consulting always seem like a temporary gig? Why can't it be permanent? I've been doing it forever, but then I thought, I have to start the podcast, because I can't only do consulting forever, even though...

Teresa Duran: I think people find joy (at least I do) through a portfolio of work.

Phil Howard: Yeah.

Teresa Duran: Part of what I've been doing lately is the national Inspire program, with its CIO and CISO networks. I'm part of a pretty small group that mentors and coaches aspiring CIOs and CISOs, and I'm enjoying it so much. It's a way to give back. I feel everything we do should be about impact. So when I think about that portfolio of work, those are the things that fill your cup in your career.

Phil Howard: If I asked you for the single biggest frustration, problem or challenge the CTOs and CIOs you're mentoring have, what would it be?

Teresa Duran: Oh my gosh. I'd say (and I feel it too) people think they can bypass you because a vendor or a business VP said something and they figured they had the better answer. Here's the deal: you'd never ask a marketing VP to go talk to your board about the balance sheet. So why on earth would other leaders be more credible than your technology leaders when it comes to where the organization should go? And I don't think it's enough to say, "It took us this long to get here."

Phil Howard: That's the key. That's what this is all about. That's exactly the heart of this show. I want to know the answer to that. Stop speaking Geekinese.

Teresa Duran: No, for real.

Phil Howard: Get into sales.

Teresa Duran: Well, that's the idea, though. As technology leaders, we have to sell. We have to market. If we spend all our time talking about tools, platforms, AI and vibe coding, we're missing the whole point. We need to sell.

Phil Howard: Which brings it back to curiosity being the number one value. It's not aggressive achievement, which might be what drives the sales guy, or scaling the company, those driven business values that motivate other people.

But to answer your question: why would someone choose that person over their IT leader? There's a reason. That person was able to sense a need and solve a problem, at least in perception, in a way the IT leader wasn't able to, or at least couldn't express. The IT leader didn't ask the questions that would dig it up.

And it comes full circle to AI. We did an AI podcast earlier and talked about building your group of stakeholders for the AI committee, or AI steering committee, whatever you call it, inside the company. We can't use AI as the hammer, where we buy some AI thing, it sits on the roadmap for 25 years, never gets used and gathers dust. We have to get our stakeholders together and find out the number one challenge we're trying to solve as a business. That's where salespeople and vendors do a much better job of uncovering the pain point, while the CTO or CIO is in the background keeping the blinking lights on and doing too much geek talk.

Teresa Duran: Imagine if, instead of explaining things, you were connecting with your leaders. Sometimes you have to create tiny demos and show the art of the possible. You have to get into that mindset. That's why I think it's good when leaders have done some consulting. You really do learn things. You also learn if you haven't spent your entire career in technology, if you've spent part of it in a business line or on a rotational assignment. People need to see and feel what it's like on the other side, in front of people in a different way.

I also believe you can't use a cookie-cutter approach no matter who you're talking to. Storytelling is an overused buzzword lately, but a lot of times people talk in the way they want to be heard, rather than connecting with the audience so they understand what you're saying and where the opportunity is. Are you finding different ways to show them? A PowerPoint doesn't always work, and neither does decoding all the crazy acronyms for these solutions. Are you giving them the right analogies, the right stories, or even the right demos to bring the opportunity to life? And why aren't we in the room with the sales team, talking about selling and delivering quick wins? Maybe we don't have the training.

Phil Howard: So back to my question: what's the single biggest frustration, problem or challenge that new CTOs and CIOs bring to you in your mentoring?

Teresa Duran: That's all it is. It's all about personal branding, selling, marketing, how to speak in front of large audiences. All of it. It's a common theme. And what a lot of people don't know is that I'm naturally extremely introverted and shy. I don't like putting myself out there, even doing podcasts.

Phil Howard: I love that. Some of the most successful salespeople in the world are known to be severe introverts.

Teresa Duran: Yeah.

Phil Howard: Science-nerd introverts who are super good salespeople. And you know why? (I need more caffeine. What's wrong with me?) They're very good at discovery. They ask a question, then another, then another, and then they shut up, listen, take notes and find a solution to the problem.

If an IT person or IT leader gets up in front of a group thinking, "Oh my gosh, I have to talk, I have to give a presentation, I have to sound smart, I can't sound stupid," then you're not selling. You're just speaking. Regurgitating stuff. And people are thinking, "Dude, are we done?"

Teresa Duran: You're showing people how smart you are, and sometimes you're offending them. I remember helping some of them with really, really big PowerPoints, and I asked them some questions about it. What actions do you want people to take away from what you're saying? You almost have to go back and rehearse: What are you trying to get them to decide? How do you want them to feel? That tells you right away whether your approach is really focused on influencing, selling and marketing.

Phil Howard: Yes, it's really about asking. We need to ask more and listen more. So do you think a How to Win Friends and Influence People type of thing, sales and marketing for IT, would be successful? We should do a course. I have no idea. Maybe I'll start a segment on every episode from now on: "This section of the podcast is how to sell yourself."

Teresa Duran: I didn't even think I'd write a book, but I started writing while I was consulting, because I kept seeing the same patterns. It wasn't just during my CIO stints or while mentoring leaders. It was happening everywhere. It was always the same challenge.

Phil Howard: It has been an absolute pleasure. We look forward to the book. Plus, we have AI now. You can sit down and just dictate. It's easier to write a book now than it's ever been.

Teresa Duran: Oh my god. Everybody sounds the same.

Phil Howard: You cannot use AI for anything human. Seriously. I want to barf every time I get an invite or email that says "the great unlock" or "we're going to unlock this." That's not how people talk. But if you get a microphone and record... I have a really good dictation app, and it asks, "Do you want me to rewrite this with AI?" Absolutely not. Use AI to take your dictation, maybe fix the punctuation, break it into chapters and outlines, and organize it.

Teresa Duran: That's exactly right.

Phil Howard: You can write a book faster. And with Amazon, you don't need to pay someone on Upwork to format it anymore. AI will do that, you upload it to Amazon, and you've got your book. You can even print it right then and there.

Teresa Duran: It took me eight to nine months to write my book. I don't think it's good. I should never have let it be published. I'm going to do a 2.0 on speaking the language of business in IT, which is exactly what we're talking about.

Phil Howard: That's awesome. Now I need to read it. You know how you look back at something you did? If I listen to our first podcast, I think, "Was I serious?" But I think it's great, because you're putting yourself out there. It only gets better.

Teresa Duran: I agree. And I feel there's always something to share, always something we can learn from each other.

Phil Howard: Go back to MrBeast's first YouTube video. It's my kids who watch MrBeast. I think his first video (Alex Hormozi mentioned this the other day too) was just him counting to a million or something. Everyone starts out with something rough. What was the first Joe Rogan podcast? Just him and his buddies sitting around talking.

It's been a real pleasure having you on the show. Teresa Duran, you've been heard.