Tim Crawford: 0:05

Companies are looking for new ways to transform their business to remain relevant and differentiated within their industry. Technology now plays a central role in this transformation. Hello, and welcome to the CIO in the Know podcast, where I take a provocative but pragmatic look at the intersection of business and technology. I'm your host, Tim Crawford, a CIO and strategic advisor at AVOA. This week I'm joined by Cindy Stoddard, who is the SVP and Chief Information Officer at Adobe. We discuss the changes for CIOs in the era of AI, along with how the sins of our past will haunt us as we adopt new innovation. Cindy talks to how architecture and technical debt will hold us back in our adoption of AI. We also talk about the softer side of being a CIO and IT leader. Cindy shares her perspective on work-life balance and what it means for executives today to be present and without regrets. We talk about what it means not to be a mushroom and the importance of people. Lastly, Cindy shares her advice for the next CIO. Cindy, welcome to the program.

Cindy Stoddard: 1:18

Well, thank you for having me.

Tim Crawford: 1:20

It's always great to see you. We've known each other for a number of years, and I'm really, really excited to get into this conversation. I've been looking forward to this for a long time, even though it's taken us this long for me to get around to inviting you on the program. So I'm glad that we could make the time. Cindy Stoddard, SVP and CIO at Adobe. Maybe just to start things off and to help the audience get to know you a little bit, tell us a little bit about yourself and your role as CIO at Adobe.

Cindy Stoddard: 1:49

That's a great place to start. So at Adobe, I run what we call the ATS organization, which has all of the applications that we use internally, data infrastructure, cloud operations, data center, networks, just a whole bunch of stuff that we really are the heartbeat of the company. That's my day-to-day role is making sure that that heartbeat stays alive. On the personal side, I'm a mom and actually a grandma. So there's two daughters and some grandchildren. And I love to garden. I love to be outdoors. So I'm a real nature person.

Tim Crawford: 2:30

Love that. And we're going to get a little bit into that and talk about that balance between being a mom and being an IT leader. But at first, let's talk about the IT leader side of things. You know, a lot has changed. We've seen a lot change over the course of our careers as IT leaders. And a lot is changing now for CIOs and IT leaders. When you think about where we are today and where we are going forward, you know, what are some things that IT leaders should be thinking about?

Cindy Stoddard: 3:00

Sure. I think that as CIOs or IT leaders, you know, when we hit the day, the focus is on getting stuff done. It can be large projects, small projects, different initiatives, but getting these things out the door. And what I found is that some of the strategic stuff like architecture takes a bit of a backseat, right? So it's kind of there, we know about it, it's in the rearview mirror a little bit. And then what happens is tech debt builds up behind us. And sometimes we're the leader that needs to come in and clean it up. You know, sometimes it's within our own organization. The reason I raise this is because with AI right now, which we all should be thinking about, it's becoming AI is becoming a forcing function, not just changing the tools that we give to our workers, our employees, our customers, but it's really exposing a lot about our ecosystems, inefficiencies, the tech debt, the disorganized data, things like that. And you know, some of these sins of the past are becoming really amplified as a result. I think that tech leaders should really be thinking more about the infrastructure, thinking more about architecture, and really raise it to the top of the list and then just force yourself to make time for it and force your staff to make time for it because it should be everybody's strategic initiative. Because you're not going to get very far if you don't have a solid infrastructure. Don't start cleaning it up. You know, you might be tempted to put it to the side and say, Oh, I'm gonna get to it tomorrow, right? Get to it, how it goes, but the price is gonna be larger, right? So I would say just think about how how clean is your data? Do you know where your valuable data is? Do you get rid of your cold storage or invaluable data, the stuff that you don't need? How organized is your infrastructure to be able to expose it to AI? And is your system of record really as organized as it needs to be? So those are just some things that I would say people should think about.

Tim Crawford: 5:21

Yeah, we could dive into each of those and have a whole episode just on each of those, because there's a lot more behind that. I mean, we talked about this right in the CIO think tank. I mean, data strategy was the very first topic that CIOs wanted to talk about. One of the things that you mentioned was paying the price for AI. And you talk about the sins that had been committed, and you have to kind of repent for those, if you will, if we're staying with the same nomenclature. Can you talk a little more about how you see that playing out with regards to impact for AI as companies want to adopt these new innovations and this new technology and how that might be holding them back?

Cindy Stoddard: 6:04

Yeah. So we know that AI is only as good as what it studies, right? And what it learns on. So remember the old garbage in, garbage out? Yep, sure do. Right? It's just gonna be multiply faster, more garbage coming out if it's not cleansed. So I would think about it in that way. On the data front, the data needs to be protected and have the right permission structures and have the right security. So, say your data infrastructure doesn't have that. Well, how would you release that to AI to help make decisions if you don't know if you're giving Tim the only information that Tim should see, right? So there's a lot of implications. And how do you know really what your most valuable data is? You know, do you have a heat map of what is used most often? You know, or decisions what goes into decisions today and things like that, in which data might be just transient and they are not used very often or used maybe just once during the transaction. And then it's, you know, it's not used at all. So all these types of different decisions, if you look at your infrastructure, are really important to be able to unleash an engine to help your employees and your customers make decisions because it's only going to be as smart as what you give it to to learn.

Tim Crawford: 7:32

Yeah. I think there's a lot of gold in those statements and a lot to learn from those statements that have to go into our thinking and how we strategize, how we organize, how we prioritize. I mean, there's so many opportunities. One of the questions that often comes up is where do I get started and where do I find the greatest value as I go through it? I want to shift gears a little bit and talk about maybe some of the tougher but the softer side of being an IT leader. And one of the things that you brought up in a recent conversation is you mentioned to never be a mushroom. Can you share what that means to you and what it means not to be a mushroom?

Cindy Stoddard: 8:17

Yeah, I'll just share a little story here from my past. So don't become a mushroom. This was a piece of advice that was actually given to me by one of the mentors I had in my career. And this was when I was promoted to vice president. So it was my very first VP title. I was working at a trucking company and it was awesome. And he said, never become a mushroom. And I looked at him kind of oddly and said, I don't know what you mean, right? And then he said, Well, mushrooms live in the dark. And he said, I probably don't need to tell you this, but I'm going to tell you this anyway, is never lose contact with people within your organization. Always stay in contact with the individual contributors, all the different levels, your business users, whoever you know your customers are, because that's how you keep a pulse on what is going on within the organization. And it will help you make the right decisions, help the success of the organization, and all sorts of things. So it's something that I've cherished as a piece of advice. I've never become a mushroom. I've always had an open door policy, and I've given many other people the same advice. I do leadership circles and things like that, just you know, stay connected, stay connected to the organization.

Tim Crawford: 9:47

I love that. And we're going to talk a little bit about your team because I had a chance to chat with them as well. And so we'll get to that in a few minutes. One of the things that comes up in that is how do you create time to learn, to experiment, to fail? These are common questions that often come up. You know, you want to be firm, you want to be exacting, but at the same time, there needs to be space for innovation. How do you balance that or how do you go through that set of challenges?

Cindy Stoddard: 10:18

Yeah, it's uh it's a great question. And it's a very important aspect, I would say, of being a leader, especially in a technology organization, because you can't stay stagnant. You need to be able to understand and bring solutions to your business, right? As opposed to just answering questions and things like that. Because many times technology can be used in many different ways. And if you understand the business and you understand technology, you can make that match. So what I've done within the organization is a few different things. I might pose a problem, right? Okay, that's like, oh wow, you know, we're spending too much time on tickets in the help desk. What can we do to eliminate them or you know, shift them left or whatever? And I have found by posing problems and then allowing people the time to work on solutions, they come back with some amazing, amazing things, right? Now, sometimes the solutions aren't gonna work. Sometimes, you know, you're you know, it's kind of goes down a dead path, but that's a learning experience too. It's a learning experience for everybody. So I've always created time for innovation. And in it right now, we have an innovation club, innovation lab that we can experiment with. We've also set time aside for hackathons, for innovation weeks. On the innovation weeks, we you know run them like kind of like a contest where we have people come in from our business, other engineering leaders, even some of our partner vendors come in as judges. So it's kind of like a shark tang type thing, even with prizes and things like that. And then the solutions go into the business as well. And this is something where you know we have started within ATS within the IT organization, but it's expanded out into the business now. So we work together. So you might have a team working on this problem, and it's going to be made up of IT and business people working together. So there's no wall there, right? There's no wall, it comes together.

Tim Crawford: 12:32

Yeah. I mean, too often, you know, it comes up there's IT and there's the business. And it creates this context of they're two separate organizations or two different entities. And what I've learned through my travels is when those come together, that's when the magic happens. That's when the collaboration happens, that's when the integration happens, and that's where that wall just disappears.

Cindy Stoddard: 12:56

Exactly. You couldn't have said it better. That's awesome.

Tim Crawford: 13:00

So one of the things that does come up, and and while this is an audio podcast, so folks can't see the video that I have the pleasure of seeing, but on your shelves behind you, you have this. I'm not sure if it's a card or a sign that says best nana ever. And I want to talk about the balance between work and home. And that is an IT leader, that's shifted, right? You talked at the the top of the episode about the importance of being a mom, being with grandma. What does it mean to you today in terms of that balance between work and home as an IT leader?

Cindy Stoddard: 13:39

Yeah, it's a wonderful topic. And I get asked a lot of questions about it when I do when I do round tables. And I will say that you do have to make choices, right? You have to balance. And my philosophy has always been that family comes first, right? Family comes first. When my daughters were young, I made it a point not to miss any of their events. So, you know, one daughter was more in sports with ice skating and swimming and things like that, and the other one was more of um creative with dance and things like that. I never miss their events, right? I was there. And you know, one of the questions I get asked is, well, how could you do that? How could you maybe say no to your boss or whatever? And you know, my philosophy has been is again, family first. I'm going to be very upfront and balance the time in my schedule because I think it's very, very important to do that. And if I was working for an organization that didn't value that, I think I'd have some choices, choices to make. I have 12 people. Once in in my career, I was speaking with an individual guy that I thought the world of, very top executive in a technology company. And we were having a conversation about this as well. And I asked him if he, yeah, I said, You have you have such a great career. You know, you're all over the world, you're doing this, you're doing that, you know, so many different customers. Do you have any regrets? And he said, Yeah, I do. And I said, Well, can you share? And he said, Yes. I've missed birthdays, I've missed baseball games, I've missed all these moments, these moments that I cannot recover. I cannot bring back. Right. And that stayed with me for the longest time. In fact, today I've been talking about it. And I mentioned it to people when they ask me about how do you how do you manage your schedule. And those moments that you can't bring back, you have to really think about. Yeah. You just you truly cannot bring back missing a birthday party or missing a dance recital, right? You can't do that. And I know you're a dance dad, so you know exactly what I what I mean.

Tim Crawford: 16:05

Yeah. There are actually stories when our son was younger and played baseball. There were stories where I would literally get off an international flight and drive straight to the baseball game to be able to score the game because my role was being the scorekeeper for his little league games. And people were like, wait a second, you just got off a 15-hour flight and you're here, you're not home sleeping. I'm like, it's all about showing up. Absolutely.

Cindy Stoddard: 16:34

Yeah. And I was saying recently, fairly recently, you know, we have a program at Adobe where, you know, you kind of mentor and shadow executives. And an eventual came to me and said, Can I talk to you? Because you have an open door and that sort of thing. And I know you're a mom. And she was a new mom. She had just come back from maternity leave. She was just having some difficulty adjusting to the role she was in. She had been promoted. It was a role with lots of men, lots of guys, which is nothing wrong with that. But they wanted to go out at night and they wanted to do this and they wanted to do that. And she wanted to go home with her baby. She actually found the potential for another role, was a stepdam, but it would have met her personal life a lot better. So I told her the story about the lost moments. And I've also told her that sometimes in your career, you have to step back to move forward. Because if you take that step back and spend the time with your family and get those, you get that pleasure, it's just going to give you so much more energy in the future to accomplish what you need to accomplish. And I'm a firm believer that you're not only going to catch up, but you're going to leapfrog because you're going to have that energy from not missing those moments.

Tim Crawford: 18:00

You know, that's a really great point. You know, not just in terms of work-life balance or work-home balance, but just in general, as you go through your career. Not every step is a step up the ladder or forward. Sometimes you have to take a lateral step or a step backwards to be able to get on a different path to change things or change the dynamics to be able to get you to go forward. So there are many different things that come into play that might cause that. It's never a linear path.

Cindy Stoddard: 18:31

Exactly. I mean, people will ask me, did you plan it out? You know, did you plan out step this, step that? No, you're right. It's not a linear path. But if you learn, if you're inquisitive, if you just want to try new things out, that's what I encourage people to do. That's what I did. That's how I found a place that made me happy in my career.

Tim Crawford: 18:56

Love that. Let's talk about making you happy for a minute and shift to talking about your team. I have had the pleasure to talk to a couple of folks on your team. And I have to say, your team is awesome. Just a fabulous group of folks. And so I wanted to share a couple of comments that they made and kind of get your reaction to it. So one mentioned that you really embody a people-centric leader and how to operationalize being a people-centric leader, and that you bring an amount of grace and patience, but also accountability to the conversation, meaning you expect excellence, but you don't expect people to be perfect all the time. So I'm curious what you think about that. That was one individual.

Cindy Stoddard: 19:41

Yeah, that's interesting. I would say that that is accurate. I do expect quality. I do expect things to be done right. But I know that we're all human, right? And things happen. And in the technology world, A lot of things can happen that are actually outside of human control, right? We all know there's logic problems, there could be all kinds of different scenarios with networks and security and different things that can happen. And what I've learned is I've seen different people react in different ways, these situations over the year. And when people overreact, it sends fear and people tend to tighten up. They just tighten up and and they can't perform. So what I've always tried to do is provide that encouragement and help people through those dire times. Be there to support them in whatever way they need. You know, if it's getting exacts or helping debug something or the right way to communicate, or you know, how do we organize and how do we go through this or that or whatever, whatever the situation is. But I found that staying calm allows people the space to think and act better than if they were in an uptight situation. And that's just my observations. So that's how I try, that's the environment I try to create.

Tim Crawford: 21:18

Yeah. And it sounds like it's playing out, at least for the comments of this one individual. Now, someone else that I spoke with on the team, talk a little bit about kind of how you conduct yourself and what you bring to the conversation. And she had mentioned that, you know, about your energy in life and how the world works, how to stay sharp while keeping curious, and then just your observability of the world and how you bring that to the team and to the conversations. What do you think about that?

Cindy Stoddard: 21:48

That's the interesting one. I have to say that I've always been, I've always been really curious at that. I can go back, I don't know, to, you know, probably when I was five years old and different things that I did at that time in our backyard or, you know, experiments with my brothers and sisters and you know, stuff that we were exploring. But I've always just looked for different things. And I'm big on nature. So I love to be outdoors, I love to observe and just see different things. Like love that a lot of deer in this neighborhood, and just how I follow people around is amazing. And I love history, I love architecture. So just noticing different things is very cool.

Tim Crawford: 22:36

How important do you think the trait of curiosity is for an IT leader today?

Cindy Stoddard: 22:43

Oh, I think it's really important. I mean, I've always been curious, but if I think about the new technologies and how they can be used, the curiosity of understanding how AI works, where it came from, what are its roots, you know, just so you can put these things into better use within the organization so you have that base knowledge, I think it's really, really important.

Tim Crawford: 23:08

Okay. Love that. Last thing I wanted to talk about before we wrap on on this episode. You know, you've had a storied history as an IT leader, well known, well respected in the CIO community. I've had the pleasure of knowing you for many years, always appreciated our interactions. What is something you would impart to the next CIO?

Cindy Stoddard: 23:33

I would say a few things. One is around the curiosity, but really one is I would say really around culture, right? One of the areas that is really important to me is how people feel when they come to work, come to the office or the virtual office, wherever it happens to be. And people have to have a purpose and they have to feel connected. So understanding culture and then bringing that into the organization so that people feel they have the opportunity to make a difference, cultivating a growth mindset so that people feel like they're in a learning situation, not just a doing, but a learning situation. So I would say that to the next CIO, wherever you are, whatever company or role you're going to go in, the people are really your important asset. I'll say that technology is easy, and I know technology isn't 100% easy, but technology can be learned, right? If you're curious, you can learn the technology. It's the people that really helped make the organization successful all around. So I would say invest in culture, invest in curiosity, and invest in being a learning organization.

Tim Crawford: 25:04

Love that. Cindy Stoddard, thank you so much. I always learn something new every time we talk. Gonna have to leave it right there. Thank you again for taking part in the episode.

Cindy Stoddard: 25:14

Thank you, Tim.

Tim Crawford: 25:17

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