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Leveraging change management frameworks to drive adoption

Express Over Espresso

Episode 31


29 minutes

Melissa Stroup is the Head of Technical Program Management for IT and Engineering at Cloudflare.

She manages an amazing team that ensures programs and projects are effectively planned, integrated, and deployed into the global production ecosystem. Having spent her entire career in IT, with a deep focus on database administration, she is truly a data nerd at heart. For a large part of her career, she concentrated on delivering solutions through the Oracle technology stack, with deliberate emphasis on high availability and disaster recovery. Her passion for technology has allowed her to work across the globe, with a two-year ERP implementation for the South Australian government being one of her biggest career achievements. Melissa spent equal parts of her youth between Texas and Iowa. While Austin, TX is now her home, her Iowa roots are never far away. She has a BA and MBA from the University of Iowa. When she is not helping organizations realize the art of the possible, she is traveling around the world embracing new cultures and cuisines.

Podcast transcript

Khushboo: Hi Melissa, welcome to our show. How are you today?

Melissa: Hi, thanks for having me. I’m great. How are you? 

Khushboo: I’m doing great. Couldn’t be better. I’m super excited to be talking about a couple of things here, like staying relevant with the ever-changing technology landscape is a very good topic that we’ve picked today for this show and also like leveraging change management frameworks to drive adoption. So this is super exciting and I can’t wait to dive into it. But before we do that, why don’t you give our audience and our listeners a quick background about who Melissa is. So tell us about yourself, like where were you born and raised, what was childhood like for you? 

Melissa: Yeah, I’d be happy to. So I was born in Arizona, actually, and I was really kind of split in terms of being raised between Texas and Iowa, which to me, now that I’m an adult, I think back to that and I’m like, well, in Iowa, the Midwest is really known for the strong work ethic. And I think Texas really instilled this strong sense of competition and adventure in myself. And when I think about those two things coming together to kind of make me the person I am, that’s where I think those came from. I’m the second oldest of four, but I’m the oldest girl. 

And it’s always interesting to me how my brother, who’s older than me, had much different expectations in terms of how well he was going to do in school or what he was going to do just even around the house, which I thought was always interesting. So for me, I was a really good student. I was really involved in many things. And I really had this sense of accountability and ownership, I think, from a very young age, a sense of independence and just making sure that I was very confident about what I was heading toward as I matured and became an adult. 

That, I think, led me into the career that I’m in now. I think on top of that, when I think about the way I grew up, my family didn’t travel a lot. And somehow I got a travel bug really early. I started studying German in like fifth grade. I started studying Russian when I got into college. I was always interested in other cultures and histories and literature, everything global. 

Those things all kind of coming together with the opportunities of technology brought me to where I’m at now, which is the head of technical program management for IT and engineering at Cloudflare. I’ve been in IT my entire career, 20 plus years. And for a large part of that, really dedicated to Oracle database administration, database engineering as a tech stack, and really trying to bring solutions that solve the problems that we see in many of the different industries. 

Khushboo: Yeah, this is exciting. And so when you were growing up, at what point do you realize, okay, this is what I want to do? This is what I love. What was the inspiration, first of all, to get into technology and innovation? 

Melissa: Yeah, that’s a great question and an interesting story. Because when anybody looks at my resume, and they see that I have an undergraduate degree in Russian and linguistics, and then they know that I’ve been in IT my entire career, they have that same question. When I was in my second year of school, I was working on my Russian and linguistics degrees. And I got a work-study job at the Cancer Institute in the Midwest. And it was a really tough job. 

I was like 19 years old. And my job was to actually follow up through phone calls. This was well before the days of all the technology we have now, follow up cancer recurrences. And it was really tough because I would get a lot of patients who either their cancer had recurred, or I would get their relatives where their relatives had passed away. And so I did that for about six months. 

I went to my boss and I was like, I love working here, but I can’t do this job. Like I’m too young to do this job and the emotional toll that it takes on you. And so she’s like, well, you’ve been here long enough where you know how we work and we’re putting in a new computer system, a new database system. So it was that Oracle database upgrade. We were changing the user interface and reprogramming it and really trying to modernize it. 

So again, this will date me because it was the age when we had like the terminals and things that nowadays that are new to the industry, they’d be like, what are you talking about? And so that was kind of where I got started. The consultants that were working on that implementation, they were very generous with their time. And so they were like, hey, we’ll teach you anything you want to know about databases. You’re really helpful in helping us understand the process here and how this works. 

It just kind of grew from there. And the more I thought about it, you know, of course, programming in the computer world is very similar to learning a language. And it just seemed to be a natural fit. And on top of that, I like to fancy myself a creative person. I’m not very creative, but I’m very black and white, very binary. I like the answers that computer technology brings, like you program something, it does what you told it to do. If it doesn’t do it, it’s because you didn’t program it correctly. 

So I came to find out that I really like that type of understanding and security in my career in knowing that there’s a long future in that and that I have a lot of control over what type of success I can bring to it. 

Khushboo: Awesome. Love that story. Now, talking about staying relevant, it is so important, right, with the ever-changing technology, especially with Gen AI and, you know, all the chat GPT stuff going around now. In your opinion, in your world, can you elaborate on the significance of staying relevant in today’s technology landscape? 

Melissa: Yeah, absolutely. You know, when I think about how I got started with database technology, if anyone out there is listening to this and they’re familiar with like the Oracle tech stack, for many years that tech stack didn’t really change. And so you would know how to create a database, secure it, maintain it, patch it, program in it, and there would be some new features, but honestly, it didn’t change a lot for many years. And then we started to get into cloud services. We started to get into multi-tenant features. 

We started to get into a lot of the microservices that allow us to be much more nimble with our technology. And I realized one day that I was outdated. I was like, I know how to do all the things that I’ve been doing for years, but when I start having architecture conversations or solutioning conversations, I am not able to keep up. And, you know, it’s a real struggle if you’re not aware of that from the beginning, like in your career, especially if you’re newer in your career, that you cannot stop learning these things. 

Like you absolutely have to proactively chase new education, new technologies. And there are things that I’ve learned like in the past five years that I didn’t know how it was going to fit into my career, but it made sense that I needed to know as much about it as I could so that I can make sure I was going to have as many opportunities for myself as possible. 

And I started just trying to consume as much as I could about anything and not even just technology, but the way that I communicate with people, the way that I think, you know, it’s a whole world out more of education, but the technology space, I find it really ironic because I was asked several times over my career, like, why did you choose Oracle as a tech stack to dedicate yourself to? And I had a lot of opportunities to diversify. 

I said, well, it’s so big, it never stops changing, like the edges of it keep growing. And that’s true. It’s a very large tech stack. But when I think about even removing those edges and really trying to understand what is going to be the most important ways to really stretch my knowledge, I learned that I can have a deep understanding of a technology, but I have to make sure I keep growing horizontally with that as well. 

You know, I think you’ve probably heard this word where you really think about the way that you are able to diversify all of your knowledge across the landscape. And that’s something that became really important to me, being able to be seen as someone who knows enough about everything that I can be pulled into any conversation. 

Khushboo: Awesome. And like, have you personally witnessed the impact of technology changing in various industries? 

Melissa: Absolutely. I mean, I’ve worked in many different industries. So right now I’m in cybersecurity, which I mean, everyone’s aware that’s changing by the day, maybe by the minute in, you know, the best way to very proactively be able to secure our data, secure our infrastructure, secure environments, new technology comes out every day for that. 

I’ve spent a lot of years in manufacturing that has changed quite a lot in the way that, you know, we’ve gone from having individuals manufacture on the floor in turning that into ways to use technology to accelerate manufacturing. And this isn’t a way in my mind that we actually reduce employees or reduce headcount. 

We just let them focus on more important things, things that really have a hard time being taken over by technology. I worked in higher education for about 10 years. I’ve seen technology really change the landscape of higher education. I mean, we know, especially coming out of COVID, it went from brick and mortar classes to, you know, everything’s online. 

Khushboo: Yeah, that had a huge change in technology shift. And I think people witnessed something that they had never imagined before. So that’s a great example right there. Now, how can professionals like or leaders strike a good balance between specialization and versatility? 

Melissa: Yeah, that’s a really good question. In my mind, I try to dedicate 10% of my week to learning something new. And like I said, I don’t limit it necessarily to just technology. It can be anything that I think is a development need for myself. I think that you have to go in and be hands-on. I don’t work for Cloud Guru, but I have found like Cloud Guru, for example, it’s an online subscription service to learn a lot of the cloud technologies. 

They’ve got hands-on workshops, they’ve got ways to, you know, go in and really show practical acumen for something that you’re learning academically. And for me, at least, like I have to do it, I have to learn the academics, but then I have to go do it and finding some sort of platform or some sort of opportunity where you can actually execute on what you’re learning. I think that part’s really important. 

I was just actually having a conversation today with the CIO conference I work with. And I was like, you know, I kind of miss the days where I would like really tactically delivering solutions that moved more into the leadership space. But I think, you know, in terms of if you’re really embedded with a technology team, it is really important to keep your fingers on the technology. And I think it’s important for you to have a dedicated goal about your commitment to staying up with that technology. I think you need to create a plan where you can do it hands-on and execute on it. 

Khushboo: Yeah, amazing. And now talking about leveraging the change management frameworks. So, again, in your world, can you provide an overview of change management frameworks and why do you think they are crucial for a successful technology adoption? 

Melissa: Yeah, it’s such a great question. And to be honest, it’s something that I didn’t focus on a lot, I think, earlier in my career. And now that I’ve really shifted away from more of the database engineering to the large program implementation, it’s rough when you work really hard on something that you believe in that you think is going to come and provide a very valuable service of like efficiency or revenue generation or whatever the goal is. 

And you look back and you talk to people in your environment and they’re like, yeah, but nobody really uses it. And that all is about the adoption side of it. And so when I started to kind of work more on these big programs, I’m like, I don’t want to just check the boxes. I want to make sure that the value we’re wanting to drive is being achieved. 

One of the frameworks I like the most is the ProSci framework, because I think that it really can work for any size of program. There’s great tools in there where you can have like a very large, very impactful enterprise program and maybe you want to use more of the tools in that toolbox, or you can have smaller efforts and maybe you don’t need all of the tools, but you can still find enough of those tools to help you drive that level of adoption. 

I think in a lot of the programs that I’ve worked on, it’s very interesting what the perspective of change management is, like organizational change management, because it’s either not understood, people say, well, what are you talking about? Or you get moving into the program, into that implementation, and they’re like, oh, yeah, we need some of that. But you’re a little bit late to the game, you know, with it. So I think it’s a bit of an afterthought. 

And even though it isn’t the hard technical side of it, it’s really important that you’re able to speak in a language, whether they’re leaders, whether they’re technical engineers, whether they’re interns, you know, the first day on the job, and you can articulate the value of something and you can use that framework to bring everyone over to your side and to a level of support. And I’m not unrealistic. 

It’s not that you’re ever going to get 100% support for all the programs you’re doing. And I recognize that. But I always say, like, you need to at least try to get everybody, even though you know you won’t get everybody. 

Khushboo: Yeah. Very well said. And in fact, I was about to ask you this question that you already answered, like, you know, because I realized like change management in a lot of organization and groups is still an afterthought and you very well described, like, it shouldn’t be and what is the distinction right there? So great tip there. Thank you for sharing that. Now, if I have to ask you, like, what are the key components of a comprehensive change management plan within a framework? What would those be? 

Melissa: I think that for me, the number one thing that I’m trying to drive absolute awareness of and acceptance for is stakeholder management. I feel like a lot of change management is really happening from the bottom up, which is important, but there also has to be that, like, top down. 

I know that everyone says that it’s in all the books, but when you look at reality, like talking to your executive stakeholders, making sure they understand, you know, what you’re trying to achieve, what are all the objectives, even though they’re generally paying for it. Like, I find interestingly that a lot of them can’t, they can’t articulate the objectives of what that program is. And I find that they’re not holding teams accountable for understanding the programs, for articulating the objectives. 

So I always have these meetings where I talk to them about my expectations of you. This is where I expect you to really participate in the conversation. I will have the same sort of accountability in my efforts, and then I’ll bring the conversation up. So that’s really a key piece for me. I think also going through a readiness assessment for change with your organization. So of course, depending on how large or how small that is, I think a very specific and objective assessment of the readiness for change. 

I think one of the things that’s happening so much, because technology is changing so fast, and we’re human beings, and we can only absorb so much change at once, we can only absorb new skills at a certain rate, is there is a huge amount of change fatigue. And I know that that has become kind of a buzzword, but it’s true, it’s out there. Everyone’s trying to do their day jobs, and then they’re trying to learn new skills, and then they’re trying to think about their future. 

Now they’re trying to adapt and participate in new projects or programs. And it’s really important as leadership to make sure that we are not creating an unrealistic velocity of change for our organizations. 

Khushboo: Yeah. And to your previous topic and discussion, like emerging trends, now clubbing that, that together here on the adoption. So are there emerging trends that are shaping the future of change management specifically for technology adoption? 

Melissa: You know, that’s a really good question. My honest answer is, I don’t know that I’ve seen really emerging trends. I think a lot of the framework that I use is the same framework that Kotter brought out decades ago, that ProSci has been teaching for years. I think the idea that we’re humans, we can only absorb things in a certain way. I think there’s new and creative ways to introduce change. 

Like I try really hard to have as many, many types of media as possible to share change. Like I’ll do videos, I’ll do blogs, I’ll do podcasts, I’ll do whatever’s necessary to help bring that change about. But I feel like in the years I’ve been doing this, that piece of it, and in terms of the way it’s delivered, hasn’t really changed a lot for me. 

Khushboo: Yeah. Any final advice for organizations looking to harness change management frameworks to drive a really successful technology adoption? 

Melissa: Definitely. As I mentioned, like doing the initial assessment to just kind of determine how large your change effort will be in accordance with what you’re trying to accomplish, I think really devoting some time to understanding the resistors to the change is helpful. And I think being very sensitive to the fact that probably whatever change you’re doing is going to change people’s jobs. 

I think we take it very lightly that we have to actually facilitate new education for them. We have to facilitate the ability for them to become comfortable with that new technology. I think the other piece that’s missed a lot is when we have new technology, it’s new. And so there’s going to be some level of failure that happens at different levels. 

I think the acceptance of that, working that into your plan, making that more of a positive activity in like a lessons learned, using that lessons learned as part of your organizational change framework is really important because if not, it becomes demoralizing and it really works against the change that you are trying to instill within your environment. 

Khushboo: Yeah, love that. Awesome. So Melissa, now talking about your experience and your career that you’ve built, and I would say amazing experience working in different domains and industry. You started from like you started in 1994. That’s what your LinkedIn says. Fast forward to where you are today at Cloudflare as a head of technical program management on the IT and enterprise engineering side. If you have to kind of sit down, look back from where you started to where you are today, if you have to talk about two of your biggest wins, something that you really are very proud of, what would those be? 

Melissa: Yeah, those are easy for me. Again, I focused quite a lot on really large scale environment or ERP implementations. So one that I’m, this is probably the one I’m the most proud of, is a huge ERP implementation in Southern Australia for the South Australian government. They were upgrading their tertiary student environment. And as I mentioned before, you know, the higher education space has seen a lot of change. 

So when we talk about this, like their previous system was all the students had to come in across 53 campuses, 85,000 students, 4,800 staff, they had to come in, they had to sign up for classes, they got mailed grade balers, like everything was done basically through paper and we were putting in a new system that would allow everything to be done online. And I played every role. I was the database administrator, I was a technical architect, I was a trainer, I worked on data migration, I set up reporting servers and data warehouses. 

I really ran the gamut on that program and it was two years and I got to live in Australia, which I love. I consider that a second home. And we finished that program on time and on budget and I made friends for life. So that’s definitely one of my absolutely most favorite efforts that I worked really, really hard. I’m talking like 60, 70 hour weeks for weeks on end, but it was absolutely worth it. 

And then I think the second one that I would say is I worked at National Instruments and I was this technical lead for another ERP effort where we had a Oracle e-business suite environment that serviced the Americas, we had one that serviced Europe and Asia, and we wanted to bring it together in what we called the global single instance. 

So this was like a new ERP installation, we had to migrate two existing ones into it, we had to add a bunch of new features to it. I won’t get into the nitty gritty, but that was like another like year and a half, I got a lot of work between the US and Hungary and Malaysia on it. And again, it was very successful, we achieved all of our goals, it was a lot of work, but at the end of the day, between those two efforts, it really taught me that I feel like I could probably figure out anything I needed to figure out and I could deliver anything I was asked to deliver. 

Khushboo: Awesome. Love that. Both the stories. Amazing. So the wins there, that’s, I’m sure, something to be proud of, for sure. Now while we’re talking about the wins, failure is also part and parcel of life. So if I have to ask you, like, what are your most epic failures? And also, how did you bounce back from that failure? You definitely know what not to do, right? So what are those stories? 

Melissa: Yeah, I thought about this a lot. I was trying to be very objective because it’s hard to talk about failure, but I really centered on one in a fairly recent, for the last four years or so. So as I mentioned, I’d really been focusing on Oracle, even as a leader, managing database administration teams, managing large efforts. And I went to Oracle Open World, this is probably like five years ago, and generally I would use that effort as an opportunity to educate myself. 

And I came away from that experience with my eyes wide open, understanding that the world had passed me by, and everything is cloud, and I needed to jump on the cloud bandwagon. And so I came back to work, and I was like, I need to create a new initiative, a new program where we talk about cloud adoption, because we were very data center focused. And I could tell right away that we really needed to kind of shift a strategy. 

So I got the support to create a cloud foundation initiative, and the goal of it was to drive cloud adoption. And what I was supposed to accomplish at the end of it was a majority of our applications would be moved from the data center to cloud providers, and we would go through this whole exercise of how that would look. And what I ended up accomplishing was not my goal. 

I did not move very many, if any, of our applications into the cloud. And it was really rough, because I think I spent about a year and a half on that effort, like really trying to get educated, really trying to research myself, trying to do all the organizational change management, and there were so many factors that weren’t working for it. Like, just to talk about the human element with organizational change management, this is one of the big technology changes. Being a system administrator or a database administrator or a network administrator in a data center is very different than doing those jobs for cloud provider services. 

Really understanding how to be in multiple clouds, really understanding performance issues and licensing issues, all of the pieces that come together with cloud migration, it was a tough job. I had a lot of people asking me, like, okay, if I jump on this bandwagon and I decide to move my applications to the cloud, like, how much is it going to cost me? 

And I’m like, I don’t know. They’re like, well, what’s going to be impacted? How is it going to be sequenced? I’m like, I don’t know. I said, I don’t know more for that effort in my life than I think on anything else. So that was rough. And what I did is I thought about it, I took a step back, and I was like, this is not working. There’s too many things that I don’t know. There’s too many things that I can’t find a way to create like a good comprehensive solution. And, you know, this is a big deal. This is, you know, big company, publicly traded, very complicated infrastructure around the world. And you can’t just do those things lightly. 

So when I took a step back, what the realization is that there is a huge gap in understanding what the current landscape is, like, we don’t know where the edges of this landscape are. And without knowing that, you can’t know where you’re going to. And so I kind of turned it into another opportunity of creating a map of our landscape and trying to get answers to all the questions I didn’t have answers to, so that that next phase of work could begin. 

Khushboo: Awesome. Thank you. Thank you for sharing that with us, Melissa. Now before I let you go, if people want to reach out to you and know more about the exciting work you’re doing, where can they find you online? 

Melissa: They can find me on LinkedIn. So Melissa DBA is my LinkedIn name there. And I’m there and available. 

Khushboo: Awesome. Love that. Thank you. Thank you so much, Melissa, once again, for coming on the show, sharing these amazing stories, nuggets. This was very interesting, and I’m sure this would be super helpful for our audience on the show. 

Melissa: My pleasure. Thanks so much. 

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