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Navigating the Digital Continuum: My First 60 Days at Highlight

  • James 'Jim' Eselgroth
  • October 31, 2023
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We live in an era of rapid technological change that requires organizations to continually adapt and transform. Many leaders in the public and private sectors often find themselves having to address these technological changes. But how do we do it? Is it through a tech strategy or digital transformation? What should it look like? How do we ensure we don’t erode our culture or identity? And most importantly, Why? I want to share my first 60 days as Highlight’s technical executive leading Technology and Innovation. Of course, Highlight made the first tough decision for me by establishing our T&I office. As Mark Twain once said, “The secret of getting ahead is getting started.” [1]

These first 60 days were an extremely enlightening blur. During my time in the military, I learned early on that the first action when leading a new office or team is to talk to as many stakeholders as possible and sit back and observe for at least two months. Why? Because I don’t want to come in as “that guy” who makes changes without having a basic understanding of the current organizational dynamics related to the people, policies, processes, partners, or platforms.

A few years ago, when attending the Foundation for Chief Data Officers Course sponsored by MIT, I learned that as an executive, there are three factors essential for success:

  • (1) the authority to execute,
  • (2) a budget, and
  • (3) resources (people).

Without having direct control over these three critical pieces, your success will be directly tied to whoever has control over one or more of the factors.

Planning for the Future

So, where did I begin? I drafted a plan paired with a clear authority to execute. We needed a Technical Strategy (the plan) and a charter (authority). Why is having these key documents important? I think Gen (Ret) Gordon R. Sullivan put it best in his book and the title, Hope is not a Method [2]. Essentially, effective planning fosters accountability by guiding our actions; as we can’t hope for the best, we need to plan for it. It enables us to strategically allocate our resources (including people, time, finances, information, and equipment) to maximize their impact on our objectives. Planning is the foundation for us to assess and evaluate our accomplishments with precision. Our strategy for the Highlight Technology and Innovation office outlines four pillars: Domain & Capability Management, Innovation, Vendor Partnerships, and Thought Leadership.

In addition to a plan, the other key element to adapting and transforming to new technology is understanding how it will effect the organization. When we talk about technology strategies and change, we’re talking about digital transformation. When executing the “Digital Transformation” process, we often consider the people, policies, processes, partners, and platforms. Why do we have people first? From my observations, for a few reasons:

  • Most technology is designed to help people,
  • People are often the largest enablers in the change process and
  • Technologies almost always have an impact on how people work.

So, digital transformation isn’t just a process. It’s also a mindset.

“Don’t be fooled by some of the digital transformation buzz out there, digital transformation is a business discipline or company philosophy, not a project.” — Katherine Kostereva [3]


From Digital Transformation to Digital Continuum

Personally, as a mindset, the phrase “digital transformation” doesn’t cut it as it implies there’s a beginning, middle, and end, as though the transformation is somehow complete. This is a pitfall! Maybe a more appropriate terminology for people and organizations is to call it a Digital Continuum. After all, change is constant.

As a young airman, I recall a speech by Gen. John P. Jumper, now retired, where he emphasized the need to “be comfortable being uncomfortable” when it comes to change. This year, Gen. Charles Q. Brown, now Chairman of the Joint Chiefs of Staff, echoed this sentiment. Their message has stayed with me: We must embrace the rapid changes and discomfort that come with adopting new technologies. Morphing technology necessitates adaptability. Here at Highlight our Digital Continuum begins with understanding where our own people are in their openness to change, to new technologies, and developing a Digital Literacy training plan.

When considering digital transformation, it’s essential to recognize the close relationship between a well-defined technology strategy and the continuous nature of this process. A clear strategy acts as the guiding compass in our digital journey. It ensures that our transformation efforts remain not only purposeful but also adaptable in the face of constant change. In the dynamic landscape of technology, having a strategy isn’t a one-time event; it’s an ongoing commitment to aligning our initiatives with organizational goals and the evolving needs of our customers. It’s the thread that weaves the past, present, and future of digital transformation into a coherent narrative.

As I reflect on my initial 60 days at Highlight Technologies and our path toward a “Digital Continuum,” I’m reminded of the ever-present need for strategic clarity in this fast-paced digital age. In a world where change is the only constant, a well-crafted technology strategy is our North Star, helping us navigate the uncharted territories of digital transformation. It’s not just a plan; it’s our commitment to staying relevant, adaptable, and, above all, true to our vision. So, I encourage you to embrace the concept of a “Digital Continuum” and remain open to change, for therein lies the promise of progress and innovation.

[1] https://quoteinvestigator.com/2018/02/03/start/#:~:text=Mark%20Twain%20put%20it%20another,starting%20on%20the%20first%20one.%E2%80%9D
[2] https://www.amazon.com/Hope-Not-Method-Business-Americas/dp/076790060X
[3] https://chiefexecutive.net/real-meaning-digital-transformation-increased-agility/
[4] https://www.daytondailynews.com/local/get-comfortable-being-uncomfortable-air-force-chief-tells-dayton-audience/ZI4G4RDJDVAWDEFZ3GKD7UONBM/