In an era defined by AI, automation, cloud scale, and rising customer expectations, today’s CIOs are navigating a once-in-a-generation strategic inflection point. The pressure to modernize legacy environments has never been higher. The demand for speed, innovation, and business value has never been greater. And the challenge of getting it all right at the same time has never been more complex.
Shelia Anderson, chief information and digital officer at Unum Group, describes this moment as “managing the dance”: the dance between stabilizing and modernizing the core while accelerating new digital capabilities; between protecting the enterprise and empowering it; and between delivering for customers today and architecting a future where AI and automation fundamentally reshape how work gets done.
In a recent episode of the Tech Whisperers podcast, Anderson shared what CIOs must get right architecturally, operationally, culturally, and strategically to lead effectively in this AI-powered era. Afterwards, she expanded on the essential questions shaping the CIO agenda as enterprises reinvent themselves for the future.
As Anderson makes clear, this moment requires more than technical strategy. It demands leaders who can architect for the future while modernizing the past, who can move fast without breaking trust, and who can balance innovation with empathy. What follows is our conversation, edited for length and clarity.
Dan Roberts: When you think about the architecture of the future, what are the non-negotiables CIOs must get right to support AI, automation, cloud scale, security, and faster innovation?
Shelia Anderson: You have to get a vision of where you are today and where you’re going. You have to get that foundationally right. It’s about establishing a future target and making sure that you have an understanding of your current state as well — that’s table stakes for me.
You’ll often hear me talk about multi-year planning. I am a big believer in a three-year plan. It’s tough right now to have a three-year plan. Still, establishing a solid outlook for even the next 12 months is important. We have to find balance between the legacy technology that we have — and we’re all still dealing with it — and the new emerging technology and disruption that’s coming.
There has to be enough rigor and focus on how to get from where we are today to the new. That’s one of the things that’s going to challenge most of us: How do we think about the blocking and tackling, the modernizing, and the reality that “modernizing” may look very different with all the new capabilities we have coming? A multi-year plan is the tool that can help us balance priorities and get from here to there.
Also table stakes for me is the talent approach to all of this as you think about the future. You have a roadmap based upon a rigorous architecture discipline. How are you thinking about aligning your talent to that? Because it all anchors back to your vision of the future, the timing of that transformation, and a multi-year plan and roadmap. And layered on top of that are your organization’s constraints — capacity for change, investment strategy, whatever they are — all these things come together.
Modern architecture works only if the operating model evolves with it. How do you think about designing the operating model of the future to move at the speed the business now demands?
We’ve got to learn how to put a little jet fuel beneath what’s called agile today to drive it forward at yet another level of speed, particularly when it comes to speed to value and speed to outcomes. More teams are going to ask for that. It’s a clear ask from our CEO, so it’s always top of mind for me.
We’re working in close partnership with our business to reimagine how to solve for an end-to-end view of our business while enabling speed, agility, and adaptability. For example, we’re exploring how to design our operating model of the future around end‑to‑end value streams rather than the core capabilities we use today. It’s about organizing around the customer lifecycle, putting the customer front and center, while creating clear accountability and clear ownership around decision‑making as well.
Then, focus on the governance aspect: How do you make sure you are prioritizing the work and making sure it’s aligned to those priorities? Next, look at the constraints you have. As much as things are changing, the familiar constraints still exist: people, process, and technology. If you have a constraint around your investment processes, for example, then you have to address how to balance those across the others.
Ultimately, I think success depends on collaboration, continuous learning, an integrated approach, and process, process, process. With AI and the pace of innovation, we have to totally rethink our business processes, and it’s not always going to be about iterative or evolutionary change. It’s going to be revolutionary in many situations.
Every CIO I talk with is trying to find that Goldilocks zone where the balance between modernization, innovation, speed, value, and risk is not too much, not too little, but just right. How do you approach that balancing act? And how do you help your organization understand the choreography behind the decisions you make?
First, you have to have a foundational understanding of the current situation within your business. I always follow the dollars in the beginning, because that tells you a lot about where the business sees the opportunity to get value and whether your investments are really achieving that. Then, I look at the balance of investment between run‑the‑business and change‑the‑business activities. It’s a balancing act to reduce run costs to free up funds for value creation on the change-the-business side.
Getting that foundational view of what that situation is first will help you make better investment decisions around everything — for example, how you source work for everything from tier 1, mission-critical capabilities to commodity services. Those are the things that we have to make very intentional decisions around. I’m going to put my best, most innovative, probably higher-dollar and skilled people on that mission-critical piece of work, and maybe I’m going to source that commodity service differently so I can free up those dollars to drive them more towards value creation.
Transparency in the decision‑making is key. You have to explain the choreography behind the dance and the trade‑offs. That’s not a science; it’s a muscle that allows you to navigate through stop, start, continue decisions. If we want to start shifting investment dollars to higher value creation, then that also implies that you’re actively making choices to deprioritize other things. That’s where those relationships and the ability to adapt and trade off are going to matter, so you can get alignment around the decisions.
And then I always like to say, use the data to help you to make informed decisions. Use your governance, use your metrics, to help you in making your decision so you can get into that Goldilocks zone. As long as you’re aligned with your business — if your business is saying, “We’re at a point where we want to invest more for this period of time in this one capability, and we’re going to minimize investment in another” — that’s fine. You can support the decision and align to that if that’s where your business wants to take it.
What does workforce transformation look like in this AI-driven era, and how are you helping your 2,000 technologists navigate disruption, build confidence, and develop the skills needed to thrive in the future of work?
There’s a massive amount of change and expectations coming at all people, especially those of us in technology. There’s all this new emerging technology, a lot coming with AI, that brings expectations around how you shift from ways of working today to a level of productivity expectation tomorrow from leveraging these new capabilities.
One thing I’m doing to take fear out of the equation is to help teams see a path forward. I do that by setting goals for the organization and having a vision around those goals. That gives you confidence — as an individual sitting in a chair — that there’s a vision not to replace me here but to help me be prepared with the skills needed for the future. Jobs will change a bit, and in the engineering space, definitely, you’re going to see a higher dependency upon leveraging these capabilities to help you get more work done. That’s the expectation. We’ll have the capacity to say “yes” more often. We’ve already proven that out in some early pilots and tests. So, I’m excited about the future opportunity, and I think when the success comes, we’ll all be celebrating that.
At the same time, I think about the broader AI‑ready workforce. Regardless of where you’re at in the organization, all people are going to have to learn how to leverage these new tools effectively. To do that, identifying things like skill gaps and targeting future growth skills is going to be important. Creating learning pathways and, more than anything, reinforcing that culture of continuous learning, change, and adaptability is going to be key. Offering targeted training and upskilling to help people learn the new tools, plus transparency about how those capabilities will change and, ultimately, augment or enhance their jobs, will build confidence for the future.
You’ve been recognized with some of the most prestigious awards in our profession, including the CIO Hall of Fame and Constellation’s BT150, which highlights the world’s most influential business technology leaders. What do they represent to you about your career and leadership journey?
I feel like I’ve gone viral in the last quarter of my career. I haven’t necessarily changed, but there’s an awareness factor that has come through — maybe through my network, through participating in some of these organizations, for getting out there and sharing the stories of my companies.
As a female leader in technology, I feel a tremendous opportunity and commitment to set a precedence so other leaders can see this as a role that they could aspire to be in as well. That’s what it really means to me, and I don’t take the responsibility lightly. It’s representing a future path for other women, and other technology leaders as well. Sharing my story is important, and I think these recognitions definitely do that. The awards also help to highlight some of the wins across the whole industry and the great teams that I’ve had the opportunity to be a part of. It represents all that work across all the years.
What advice would you offer the next generation of leaders stepping into this AI-driven future?
You won’t always know how developing new skills and early experiences will pay off later.
The role I probably disliked the most was when I was running a global network for American Airlines. I was an applications leader, and my leader asked me to take on the network responsibility. I didn’t enjoy it; it was painful. But I learned how to optimize business. Then 9/11 happened and I learned how to reimagine how I work with every supplier, renegotiate contracts, things I never imagined I’d do and that I use today. I am a shrewd contract negotiator, and I credit that skill all the way back to when I was a senior director in that role.
You never know what will happen. Take those opportunities, the stretch roles, raise your hand, and pivot when you can. Don’t focus on going up; focus on horizontal expansion. That’s where you’re going to build the toolkit you will carry for your whole career. It’ll help you be successful in the later years, when you are moving up into senior roles.
There’s also the power of context, which I relate to that broader view of strategy and vision and understanding larger opportunities and outcomes. When you’re early in your career, if you laser focus on the thing in front of you, you’re going to miss what I call the fringe opportunities. So, from a career perspective, broaden your horizons. Think of the broader view of whatever it is, whether you’re solving a problem or seeking advice. Context gives you a perspective of situational details, and all of those things come together to help you see if something is really significant, or how much weight you should give it. Context helps you pick your battles.
Finally, make business fluency a big part of what you focus on. Don’t focus just on the technology of the moment. Technology comes and goes, which means you need to be continually learning new technical skills. Be a continuous learner, have curiosity, ask great questions, and focus the early part of your career on skill-building and building a great breadth of experience.
As organizations confront the realities of AI, shifting operating models, and rising expectations, Anderson offers a blueprint for leading with clarity, courage, and a deep commitment to people, the true engine of every transformation. For more insights from her leadership playbook, tune in to the Tech Whisperers podcast.
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