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In this installment of the IT Leaders Fast-5 — InformationWeek's column for IT professionals to gain peer insights — Thomas Phelps IV, CIO at geographic information systems company Esri, shares his alternative approach to IT project management, which avoids using technology as a "sledgehammer" to force business outcomes. Phelps also discusses why investing in process improvement and upskilling his team is a top priority.
Prior to his role at Esri, Phelps was CIO and senior vice president of corporate strategy at Laserfiche; a director in the IT security, privacy and risk national practice at PwC; and part of the team that launched the Internet Software Products Division at Motorola.
This column has been edited for clarity and space.
The Decision That Mattered
What decision — technical or organizational — made the biggest difference recently, and why?
At Esri, we're continuing to invest in talent that really enables our business capabilities and outcomes. One example is focusing on the area of process improvement. We just hired and onboarded a process improvement specialist within the IST organization, and even this morning, I was on a kickoff call with her talking about contract lifecycle management, and I was so impressed with how she managed a meeting and really focused on outcomes.
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When you think about technology and change, it's not just about the technology for technology's sake, but it's about people, process and technology — I also like to add culture and org structure.
Looking at the lifecycle of business process as it relates to specific technology areas is definitely the right approach. It's an approach that we continue to invest in internally as we partner with our business stakeholders, whether it's the global sales division, marketing or finance and accounting.
What are your specific goals for process improvement, and how is that new specialist addressing those goals?
From an IT perspective, we're managing multiple projects — about 38 discrete projects concurrently — that have impact on different parts of the business and involve our customers.It's really important that we not just execute well on these projects, but also look at ways we can automate and do things differently. You can always automate a bad process and do the bad process faster, but we want to be able to really make a difference for business stakeholders by looking at how we do things, what are we trying to accomplish, and do things in a way that both scales and identifies the root causal factor of the problem we're trying to solve.
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By looking at things from a process improvement lens, it gives you the opportunity to not bring a sledgehammer that's called technology or called AI to a solution that could be better served by looking at where there are gaps in the process or too many steps involved. Not every problem is solved through technology. How do we reengineer and reinvent the process and use technology and AI to enable that process to perform properly?
The Hard-Won Lesson
What didn't go as planned recently — and what did it force you to rethink?
I'll talk more broadly about my entire career. A hard-won lesson for most CIOs, including myself, is making sure that you don't have an overreliance on systems integrators and third parties to be able to accomplish specific initiatives.
As you engage a third party, consider how to increase your business capability to provide ongoing support, updates and maintenance of whatever that third party is implementing. I want to make sure there's clarity in terms of what they're delivering, and that we're aligned with the right outcomes.
As they deliver, I make sure that I have a team that is stood up or that's reallocated to be glued to the hip with that third party, so then they're learning. Whether it's an ERP upgrade or a new security implementation, I want to make sure that we're gaining institutional knowledge of that particular vendor's product, so that we have that capability to support the business once they're done with their engagement.
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As you invest in an initiative, anticipate different outcomes. There will always be staffing and scope changes with a project. In the planning process, it's about budgeting for that extra time and that cost up front so you don't get into the situation where you don't have enough funding to get something done.
Not only do you want to vet the organization providing services, but you want to vet the CVs of the individuals on that project … make sure you vet the experience and skill sets of the people delivering.
The Talent Trade-Off
Where are you investing in talent right now — and what are you consciously not investing in?
I've partnered with the employee development and training group on two things. One is we provide leadership training on an annual basis for our IST colleagues.
Second, from a technical perspective, is assessing the skills that we already have, but how do we augment those skills? For example, courses on a particular vendor's technology AI stack.
The most important thing, though, is providing capacity. One of my initiatives this year is how do we help employees get the capacity and time to learn, to innovate, to experiment? We want to make sure that we allocate time and capacity for our colleagues to experiment, to learn and apply that learning toward working on initiatives that deliver the right businessoutcomes.
The External Signal
What recent external development is most likely to change how your organization operates, even indirectly?
In our IST team, with the rapid advancement of new AI models it's important for us to contemplate the impact on both our products and what we leverage internally. That involves ongoing monitoring of these AI models and these advancements and looking for practical applications of how to implement AI within all parts of our business in a way that's governed, safe and done responsibly for the company.
Part of what we're focused on is leveraging AI to help provide business operations at scale, in a way that's effective for our business.
Are there any aspects of AI — you mentioned governance — that you're most concerned about?
One is to make sure there's appropriate observability with a control plane for all these agents that are within your environment. Also, having an inventory of these agents, what they do and what permissions and roles they have. That's critical to AI governance.
Also, making sure that whatever agentic technology is running has the right guardrails and controls enforced.
The Perspective Shift
What have you read, watched or listened to recently that changed how you think about leadership or technology — even slightly?
The book "Scare to Cares" by Saby Warriach. It's about how to lead digital transformation without chaos. We're hearing a lot today about fears of AI and how it's going to disrupt jobs.
As a leader, are you creating stress, chaos, and anxiety, which then leads to resistance to change? How do you move from that to being an empathetic leader, recognizing the impact of changesto people's jobs and what they do every day? [The CARE acronym] is C for communicate with empathy, the A is about adapting with agility, the R is building relationships based on trust, and the E is empowering your team with that trust to get things done and accomplished with the right governance and guardrails, and through the right coaching and mentorship. The S is stay calm through changes.
My favorite book is "The 7 Habits of Highly Effective People" by Stephen Covey. I really like the principles-based approach in terms of leadership. I'm also a voracious reader of the news.
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About the Author
Senior Editor, InformationWeek
Kelsey Ziser is a senior editor at InformationWeek, where she covers C-suite dynamics, data strategies and the evolving cybersecurity threat landscape.
Kelsey also oversees the publication's IT Leaders Fast-5 column, which brings peer insights to IT professionals, and the tech layoffs tracker. She has been with InformationWeek since September 2025.
Before joining InformationWeek, she spent nine years at sister publication Light Reading, reporting on a broad range of topics including smartphones and devices, AI, satellite connectivity and enterprise networking. Kelsey has a Bronze Regional Azbee Award in the Technical Article category. Outside of work, she enjoys reading four (or 12) books at once, watching movies about space travel, crafting and tending to an ever-growing collection of houseplants. Kelsey has a bachelor's degree in journalism and mass communication from UNC-Chapel Hill and is based in Raleigh, N.C. She can be reached at [email protected] or on LinkedIn.

