Episode 42: Driving Digital Transformation…Through Leadership, Humility and Empathy

What does it take to guide a business through digital transformation? It’s more than just investing in the right technology and waiting for the benefits to roll in. For Greg Bowen, SVP, Digital Acceleration & CTO, Dell Digital, transformation is just as much about people, process and culture as it is technology. It takes humility, empathy and patience to affect true transformative change. In this episode, Greg explains how the process is underway at Dell Digital, the IT organization that supports Dell, and how you can get started with your business.
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Listen In To Learn:

  • How to reduce risk and get buy-in for digital transformation
  • How to identify the right starting point to begin the process
  • The guiding principles of leadership during transformation and beyond
  • How to address the four most significant barriers to transformation

The Human Element of Digital Transformation

“The shoemaker’s children go barefoot.” It’s a common proverb that applies across industries: The thing you do best for others can be the hardest to do for yourself.

Dell Technologies is leading the charge for digital transformation. They help businesses reinvent themselves through technology to run faster, more efficiently and ultimately to greater success. It’s up to folks like Greg Bowen, SVP, Digital Acceleration & CTO, Dell Digital, to make sure that the same transformation is happening internally.

Greg is accelerating Dell Digital’s transformation by looking beyond just technology. For Greg, it’s a human challenge as much as a technical one – the challenge of convincing 10,000 employees to make radical changes in the way they work. Using Pivotal Labs methodologies, Dell is making a tremendous shift in how its own IT organization, called Dell Digital, operates to quickly design, develop, iterate and deliver new products and capabilities.

Featured Luminary: Greg Bowen, SVP, Digital Acceleration & CTO, Dell Digital

Greg Bowen is senior vice president of Digital Acceleration and CTO of Dell Digital, the IT organization that supports Dell. He is responsible for advancing Dell Digital’s transformation via a combination of people, process and technology changes to enable the Dell Digital Way—a cultural shift in how team members partner with the business using a direct, simplified and streamlined approach to quickly design, develop, iterate and deliver new products and capabilities.

Greg leads the digital transformation teams instrumental to accelerating Dell’s operation as a product-focused organization, including DevOps practices and technology, enterprise architecture and innovation with artificial intelligence, automation and machine learning. He also oversees the strategic direction and tactical operations for the organization’s customer satisfaction, experience design and analytics functions.

Before joining Dell, Greg held numerous roles in operations, sales, marketing and software development in his 16 years with Amazon.

Greg began his career as an art curator at University Galleries at Illinois State University and holds a Master of Business Administration in Technology Management from the University of Washington, Michael G. Foster School of Business, and a Master of Art in Art History from Illinois State University.

Transformation is never over. The world is moving so fast around us, that expectations from customers are changing daily. We constantly need to be evolving.

— Greg Bowen, SVP, Digital Acceleration & CTO, Dell Digital

Luminaries Hosts

  • Mark Schaefer Author, Consultant, College Educator. Mark is a leading authority on marketing strategy, consultant, blogger, podcaster, and the author of six best-selling books, including "KNOWN." He has two advanced degrees and studied under Peter Drucker in graduate school. Some of his clients include Microsoft, GE, Johnson & Johnson and the US Air Force
  • Douglas Karr Technologist, Author, Speaker. Pre-Internet, Douglas started his career as a Naval electrician before going to work for the newspaper industry. His ability to translate business needs into technology during the advent of the Internet paved the way for his digital career. Douglas owns an Indianapolis agency, runs a MarTech publication, is a book author, and speaks internationally on digital marketing, technology, and media.


ANNOUNCER: Luminaries, talking to the brightest minds in tech.

MICHAEL DELL: We are technologists, and we share an awesome responsibility. The next three decades will hold even more progress coming more quickly than ever before. A new age of miracles is literally just around the corner.

ANNOUNCER: Your hosts are Mark Schaefer and Douglas Carr.


MARK SCHAEFER: Welcome, everyone, to another scintillating episode of Luminaries, where we talk to the brightest minds in tech. This is Mark Schaefer, with my co-host Douglas Karr a.k.a. Dougie Baby.


And Doug, this is really kind of an interesting show. I feel like we’ve been doing this show for two years and it sort of led up to this moment. We’ve looked at how technology is affecting the economy, the arts, sports and education. We’ve seen how Dell technology is showing up in jungles, in the ocean, on mountaintops, and even in outer space.


But today, for the first time, we’re going to be looking at how Dell technology is changing Dell.


Which I think is pretty cool.

DOUGLAS KARR: It absolutely is, yeah.

MARK SCHAEFER: It’s something I’ve been wondering about for a long time. So we’re really pleased that today we’re with Greg Bowen. Greg is the Senior Vice President and Dell Digital CTO. And he has the awe-inspiring task of overseeing Dell’s own digital transformation. And I have to say, Greg, I think about all these discussions that has led up to this moment. A discussion about how Dell is taking on this task. And this is really exciting for us. Welcome.

GREG BOWEN: Thank you. Glad to be here.

MARK SCHAEFER: Well, we’ve got a lot of ground to cover today, but I want to hear a little bit about how you arrived at this epicenter of digital transformation. Especially after beginning your career as an art curator at a museum. That sounds like a pretty unusual career path.

GREG BOWEN: Yeah, I’d say it is. And it really starts a little bit before that. I had no idea what I wanted to do in college, so I took an experimental route and tried a lot of different things. And ended up getting a philosophy degree in undergrad, thinking I was going to law school. I graduated and like, I don’t really think that’s the route I want to take. I was also a photographer student, photography student at the time, and was becoming involved in the university gallery that was in my college, in my alma mater. And decided to go get them art history master’s degree.

During that, I took an arts and technology class. And that’s where, it was the mid ’90s, early mid ’90s, and it was just coming around with HTML and Mosaic, the world wide web was just starting to take off. And I started to learn about how you could disseminate art through the web. And it was actually prior to that, I don’t know if you remember Gopher, but–


GREG BOWEN: These are folders you would put different, you know, your images, your text files, and you’d make your user go explore these folders and learn about what you’ were doing.


GREG BOWEN: Then came HTML, et cetera. And so I got interested in technology through the arts as a way to broaden our base. I was in the Midwest, and it was hard to get people to come to the museum, so try to get the museum out to them. But realized that central Illinois is not where the art scene was. And so chose to move to Seattle on a whim.

And another little interesting thing happened there. I started as a temp at amazon.com in 1998.


GREG BOWEN: As I was looking for an arts job.

MARK SCHAEFER: How interesting.

GREG BOWEN: And decided this is a really cool place, and it just took off from there.


DOUGLAS KARR: How big was the organization then?

GREG BOWEN: I was employee 2,040.


GREG BOWEN: So it was not too big, but still, you know, still big-ish then.

MARK SCHAEFER: Yeah, it’s really interesting how you’ve sort of been leading the wave. You’ve been on the crest of the wave for each of these iterations of technology going forward. What an interesting career you’ve had. As I was preparing for our discussion today, I like some of the things that you’ve written about. You have sort of an unusual human-centered view of digital transformation.

And that just kind of struck me, because I love this perspective. It includes an emphasis on grit and humility and empathy. Maybe that has something to do with your background in the creative arts. Can you talk a little bit about your approach to transformation in this human-centered view?

GREG BOWEN: Definitely. Dell is unique in that we realized early on in this transformation process, that we actually needed to create an organization that could accelerate our progress through the transformation. We know that this is going to be a hard journey. We’re trying to change the hearts and minds of 10,000 people. And I’m a real fan of Angela Duckworth’s work.


GREG BOWEN: Around Grit. And actually it’s becoming bigger in the Dell culture. She was at our worldwide leadership meeting this year. And as you go to try to change the hearts and minds of 10,000 people, it’s a hard job. And you need to have passion and perseverance for those long-term goals of getting through this. So that’s what we started to lead with grit in my organization.

But you can over index on grit and get a little too aggressive trying to achieve those goals, and realize that you have the answer and everyone else needs to listen to you. And so that’s where the humility part comes in. If you think about perception, even simple things, if you remember that internet thing with Yanni or Laurel, that was the one thing that people had a very split opinion on what they were hearing.


GREG BOWEN: So even our perceptions can trick us into believing we’re right about something. And so just learning that you have some of those blind spots, that’s where the humility part comes in. And then the third aspect, which is the empathy. A lot of people are afraid of transformation. They have no idea what this is going to do for me in my job.

And as you’re sitting across the table from a development leader who’s been doing one thing for 10 years, and all of a sudden you’re telling that person you need to change and totally 180 degree split with what you’ve been doing, they’re afraid they’re going to lose their job, or they can’t actually do what you want them to do.

Just understanding where they’re coming from, so that you can tailor your message so that they can hear it, so they can engage with it. So you put those three things together, grit, kind of that trying to get things done over a long period of time, humility, understanding that you might not have all the right answers, and then empathy, so you can really understand the person you’re talking to. That seems to be working well within the culture of getting engagement from those 10,000 hearts and minds that we need to change.

MARK SCHAEFER: It’s such an interesting perspective. We’ just, on a previous show, we interviewed Aongus Hegarty. And we talked about the psychology of transformation. That at some point, you can get technology to do anything you want. But the progress really occurs with the people. So those ideas really resonate.

DOUGLAS KARR: It seems consistent on almost every single show, when we started talking about innovation and technology, that we’re talking about how humans and culture are the cornerstone of any transformation. So it’s fascinating. And we’ve been reading about your philosophy, and you call it the Digital Way, and it’s a methodology to help customers transform. And it’s also rooted in culture. Can you tell everybody about the Digital Way?

GREG BOWEN: Yeah, yeah. So we started this journey bringing Pivotal into our organization. They’re part of the Dell technologies family. And created a lab within our organization. And we brought individuals into that lab and trained them on these new methodologies. But what we found was, that we needed to brand this our own, so Dell employees actually engaged with it. This wasn’t someone else telling us how to work. This was us transforming ourselves.

So we created the Dell Digital Way, and it’s a people and process first, and then a technology transformation. Understanding that you really need to change your operating model to change the culture. Ultimately what we’re trying to do, is get our development teams to work more closely with the business. Almost become part of the business, and get the business to become part of the development teams.

That way, you understand the outcomes that the business is looking for, the requirements that they have. And so we’ve really worked hard to change the way our people are organized. That’s the people part of this. It used to be functional silos with a lot of matrix overlays, with a lot of manual process to get work done.

Breaking those big functional silos down into small balanced teams that are led by product management, product design and product engineering. And those teams have complete ownership and control over their code. We’re breaking down our technology from our application processes into decoupled microservices, so you can operate independently and have that ownership.

And then a lot of companies that our size, enterprise scale, they run big waterfall projects. You’re probably all familiar with this. You get the requirements, someone hands you a business requirement doc, you have a product manager that creates a PRD, then they break it down into–

MARK SCHAEFER: I’m having an anxiety attack.

GREG BOWEN: Exactly.


GREG BOWEN: Exactly.

MARK SCHAEFER: This is there’s a chill going down my spine.

GREG BOWEN: And so we’re trying to blow that out. Because when you’re doing, you’re just creating risk, an ever increasing amount of risk, until you’ve hit that end date. And we were talking earlier, Doug, that you see in some old companies, you’d throw 80% of your code away when you went to go to release, because it just wasn’t meeting the needs of the business.

So we’re breaking things down in that process part of this transformation into small components that can be deployed, sometimes eight to 10 times a day. When you break something down in that small, you can fail, and you’re not going to take the whole company down with you.


GREG BOWEN: So it’s really that people, process and technology change, and that culture of interacting with the business on a daily basis sometimes to go create better outcomes for the company and for the business.

MARK SCHAEFER: That’s just so, so healthy. Because I’ve been through a digital transformations and in my old career days, and I mean, it was just really an economy of fear, a culture of fear. And literally, people were getting fired if deadlines weren’t hit. So I really appreciate that healthier approach.

DOUGLAS KARR: Well, Pivotal was a big transformation for Dell too, from a purchase standpoint and everything. I love Pivotal’s model of paired programmers and stuff.

MARK SCHAEFER: One of my favorite companies.


MARK SCHAEFER: I love what they’re doing.

DOUGLAS KARR: It’s absolutely fascinating. And some of the things that you describe are also part of the lean startup technology, or methodology. And that’s not just programming. And that’s important for people to understand. It really is this kind of collaboration between people, processes and the platforms, all kind of working together to make it successful implementation.

GREG BOWEN: And for us that, lean startup mode, that’s where you take some of the risk out of this. Because when you do big waterfall projects, you’re launching with what you believe is full functionality, the big end result, and you’re marching along. The lean startup takes the opposite approach. Take the MVP, what is the minimum viable product that you can go out to your customer or display the functionality to your business that will actually add value, and then iteratively build on that.

So you’re not investing everything upfront. You’re investing a small amount of resources or funding and proving it out. And that’s proven to be extremely successful with our business partners, because they can see something in production that I understand now with a small amount of money, where I can actually get if we continue to scale this out.

So it’s really proven to be something that business loves. We’ve had teams that have started this journey with their business partners, dell.com is an interesting one, and they’re learning so much about their customers. They’ve just thrown away their roadmap that they had had going this year, and have created a completely new roadmap based on that interaction with the customer.

And so one of the key ones was gaming. We’ve launched some new gaming series. We have Alienware. We’ve got the G Series on dell.com. And what we learned by actually talking to gamers, is that frames per second was the thing they cared about. It wasn’t all the other specs, clock speed, RAM, memory, it’s frames per second. And if we wouldn’t have asked them, we wouldn’t have put that front center on the website.


GREG BOWEN: We multi-variant tested it, we saw the uplift in conversion and we rolled it out to customers. And that’s all about talking to your customers and understanding what they want.

MARK SCHAEFER: Yeah, I’m just grinning ear to ear here. Because as a marketing geek, I love that. So interesting. I found this was fascinating and really sort of honest on Dell’s part. Last year, we hosted a show about the methodology that Dell uses to grade digital progress of a company, or even a region of the world . In fact, there’s a free tool anybody can use, and we’ll post that on the show notes. So be sure to visit the Luminary site at Dell and you can try this on your own.

And as you applied this at Dell in your own evaluation, you rated Dell in the second highest level, digital adopter. So what does it take to move Dell or any company really, from that adopter status to that elite category? Which I understand, if I remember correctly, just 5% of all the businesses are fitting in that elite category, digital leader. So how close is that within grasp of Dell?

GREG BOWEN: So I look at this as, when I put Dell as the digital adopter, I’m really talking about Dell Digital and the way we’ve started to transform. I think if you look at it from a product perspective, a lot of the VMware, the Pivotal, the Dell EMC capabilities, they’re definitely in a leadership position. The way we’ve grown through acquisition and merger, we have a lot of tech debt. It’s something that we’re working through. We had a lot of different development methodologies.

And so when I kind of be self-critical and look at what we’re doing, I put ourselves in that digital adopters. And that whole thing was about 4,600 business leaders that we interviewed in partnership with Intel. And you’re right, only 5% of companies put themselves in that top digital leader category, where they baked transformation into the DNA. That’s just the way they operate.

We have really strong investments and plans, and that’s really what digital adopters are about, is how are you investing in the future and changing the way you work. So I think that 5%, being in the DNA, that’s definitely within our grasp. The thing to remember, is transformation is never over. I think in IT, you think someone hands me a project, I go do the project, I release it, I deploy it, and then I move on to the next one.

MARK SCHAEFER: That the history of IT.

GREG BOWEN: Exactly. Think about how much tech debt that was, because you never really finish anything, but you’re asked to move on to something different. I’m trying to help our organization see that transformation is never over, because the world is moving so fast around us, that expectations from customers are changing daily. The business to try to meet those expectations is changing. So we constantly need to be evolving.

And it always will be, are you caught up?


GREG BOWEN: Are you pushing ahead? And I think we have it within our grasp being what we would consider baked into our DNA and the way we run Dell Digital. That’s why we’ve renamed ourselves, to get ourselves in that mindset. But it ultimately is pushing that people, process and technology change all the way through, so that’s just the way you operate. And you can constantly ebb and flow with competitive demands, and with what your customers are looking for from you.

MARK SCHAEFER: Yeah, I’m surprised that you weren’t placing yourself in the 5%, because that’s certainly my experience of Dell. You know, if you talk to the people at Dell, I mean that does seem to be in their DNA, this real commitment to transformation and continuous improvement and measurement.

DOUGLAS KARR: The great thing is, if you’re a digital adopter, you could be that for the rest of your life cycle and still be leading the industry.

GREG BOWEN: Well, if you think about it, there’s only 23% of companies that felt that they were an adopter.


GREG BOWEN: So the vast majority of companies are either watching and seeing, or they have no plans whatsoever.


GREG BOWEN: And I think it does put us in a good position. I like what Michael always says. I’m pleased with our progress, but never satisfied. So it’s that, you’re never satisfied with where you are and you’re always going to strive to be going a little bit further. So kind of putting yourself where there’s always this goal ahead of us. It felt like a good place for us to be and strive for even more.

DOUGLAS KARR: Specifically within Dell EMC, the transformation that took place there, it reduced infrastructure cost, provisioning cost, improved utilization rates. And so the fascinating thing to me is, all of those things probably produce less stress on people. You know, a more agile culture. So the buy in comes through the success, right?

GREG BOWEN: Definitely does. And what we’re seeing is, when you’re trying to change a culture in an organization, you look for those success ones, success poster children I like to say. And we put them up on the wall. We have a search team, for instance, that was a group of six individuals that we created for a new search capability on dell.com. And they started from scratch. We built them as one of the first balanced teams within Dell Digital.

And they took complete ownership of their code. They’re working completely in a DevOps methodology, using all of the Pivotal Cloud Foundry capabilities that we provided to them. And they deployed to production on dell.com with zero production defects.


GREG BOWEN: And they’ve been running in production for six months with zero production defects.


GREG BOWEN: So why do you think that is? They own their code. They don’t have a support team that gets the call when things break down. So they’re very diligent. They’re shifting everything left. They’re starting with a test. They make the test pass. And then they deploy to production. And because they don’t want to get paged, they put focus and diligent and quality is just baked into everything they do.

And so you start showing that, and it’s like, you work less, you don’t spend your time on fixing defects, but you fix, you are spending your time on writing value-added code and creating features. That’s a great place to be from a team perspective. So you just keep sharing those success and everyone wants to be a part of it. So that’s what we’re trying to do.

MARK SCHAEFER: I want to switch it up a little bit and talk about the human part of your job. Because I’m curious about this. I would imagine that leading digital transformation at Dell, you’re really under the microscope personally. It’s sort of like if you go on TV and see a fitness guru, you expect that guru to be fit. If you saw him in real life and they were a big heavy person drinking beer, lying on a couch, you’d be pretty disappointed.

Dell’s the leading company in digital transformation. People expect Dell’s going to be transformed. So how do you handle the weight of that responsibility on a personal level? And what lessons can you give people like you at other companies who are listening to our show today, the people that have a similar personal responsibility to transform a large enterprise?

GREG BOWEN: Yeah, this also goes back to some of that research we did with those 4,600 companies that we interviewed. 78% of them felt that digital transformation wasn’t spread throughout their company enough. So they weren’t doing enough to do this. And 91% of them felt they had significant barriers to transformation, that really broke into four different categories. Time, skills, funds and risk.

And when you break those down and start attacking them individually to understand how to overcome those barriers, that’s the advice that I would give to companies. Time, they really felt that everyone around them was moving faster than they were. They see startups are all of a sudden becoming billion dollar companies, and they don’t know what happened and why they’re not, where’d their customers go.

Skills. They didn’t believe that their people had the skills to go do this work. They weren’t digitally native. They didn’t have the skills to run the technology that’s required today. Funding. You always had to overcome funding challenges with your finance organizations. And then risks. They didn’t really have any plans or strategies to do digital transformation.

From my perspective in the way I deal with this and don’t feel the pressure, is just trying to come up with solutions to each one of those barriers to transformation. For instance, on the funding part, because that’s always the one that people start with, we built a business case and brought our finance team in to that process. Showed them the modeling that we were doing that could produce a return on the investment that they were going to make in transformation.

And then we showed them that we had the proper metrics and KPIs in place, so that they could see our progress along the way. And so once you get them to buy in and see that there actually is a return on this investment that you’re making, and you show them you have a way to track progress, we got the funding one knocked out of the way.

MARK SCHAEFER: It was a pitch.

GREG BOWEN: Yes. It was, you know, it was a sales and it was a pain, but we got it done. So just trying to look at each one of those barriers and take small steps to overcome them. And my hope is that you look up one day and you’ve become that transformation guru, instead of the big guy laying on the couch drinking beer.


MARK SCHAEFER: What percent of your time is spent sort of in a consulting role with customers?

GREG BOWEN: Customers? Well–

MARK SCHAEFER: Just to help them through. Like you said, sort of like logically stepping through those obstacles and bringing them down, talking them down.

GREG BOWEN: Yeah, well you know, I probably meet with three or four customers a week in various EBCs or phone calls. And we often have an initial meeting, and it’s as if we’re staring each other in the mirror. That we both started this transformation journey. We have fits and starts where sometimes we’re ahead, sometimes we’re behind. And sometimes it is more of a commiserating experience than a consulting experience.

But we are able to share. Because I like to learn what’s happening. Our customers sometimes have very innovative ideas about how they’ve employed our technology. And we can learn from them as well. But what we do realize is, they’ve come to the realization that just employing this technology is not enough. And they’ve asked us, how do you do this?

And that’s the other thing that we do with the Dell Digital Way is a consulting and a partnership with our sales organization, to actually talk to them. Because we’re practitioners. I don’t really have a vested interest in selling. I like it when they close a deal, but they really like to hear how we’ve done it, how we’ve implemented it, how we’ve overcome that problem. And it really resonates with them. So it’s a good learning experience for both of us.

MARK SCHAEFER: Yeah, a nice club.



DOUGLAS KARR: So building on that idea, Greg, we’ve seen research that digital transformation has actually slowed many companies. From a leadership perspective, what advice would you give to help those people kind of re-engage and accelerate their digital transformation?

GREG BOWEN: So digital transformation is hard. And the word digital transformation becomes meaningless, because you throw it around so much.


GREG BOWEN: But change is hard. Change in an enterprise organization is extremely hard. And I think breaking that change down into smaller deliverables, just like we’re trying to do with the software process, is my number one piece of advice. Don’t think you’re going to solve this all in a year. Try to look at where are you going to get the most value.

You’re going to have some implementation help from our services organization on getting the technology within your data center or the tools that you’re using. Also look at how, you know, it’s back to that culture. Make sure that you are looking at those barriers, you’re hiring the right skill sets, you’re training your people on new processes.

For us, for instance, we realized that we had a large population of program management, and we wanted to give those individuals some opportunity to learn new skills. So we created a coding academy and we’re just about to graduate our first 60 individuals who now are full stack developers.


GREG BOWEN: Based on, and they were program managers. So take those opportunities, look for areas of big wins, and take small steps. Because I think small steps will accumulate into a big transformational changes.

MARK SCHAEFER: Well, Greg, this has been an amazing discussion. And in some ways, not what I expected.


Because we’ve talked about grit, humility, empathy, listening to the customer, and it’s almost like I’m talking to someone from HR or something.


But I think they’ve got the right man in the job, that’s for sure. So Greg, thanks so much. We’ve been talking to Greg Bowen, Senior Vice President and Dell Digital CTO. Thank you so much for your time today, just been a pleasure.

GREG BOWEN: Thank you, had a great time.

MARK SCHAEFER: Thanks to all of you for listening. We just love the great comments that you send our way, and we really appreciate your support. Keep listening. And this is Mark Schaefer. And on behalf of my co-host Douglas Karr, we’ll see you next time on Luminaries.

ANNOUNCER: Luminaries, talking to the brightest minds in tech. A podcast series from Dell Technologies.