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The Evolving Executive The Evolving Executive

The Evolving Executive

by Cliff King
Cliff King Cliff King CEO Emeritus at Skyward
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In nearly 7 years as CEO, I’ve witnessed my share of change. If I were to compare my role when I stepped into the position to my responsibilities today, the two job descriptions would have striking differences, even in such a relatively short period of time. The same can be said for the school district executives that I’ve worked closely with over the years.

Technology has played a central role in this evolution, including the growth of social media platforms, large-scale enterprise data management solutions, and the amount of information available for consumption on the Internet. The need to keep up with everything from infrastructure to professional development is no longer an afterthought, but a paramount requirement for the position.

When I think of the traits that define a strong executive in the digital age, both in the public and private sectors, there are four that come to mind.


1) Visibility

In this day and age, information is delivered in an “I need it now” world. With the rise of social media, rumors can become breaking news stories overnight. No longer is it possible to “lead from behind the curtain.”

The role of a principal executive has always been to execute the vision of his or her board while serving a wide variety of stakeholders. Now, it’s not enough to simply define our vision and hold others accountable for carrying it out – we must be actively promoting it through as many channels as possible to ensure both clarity and buy-in.

In the education community, many superintendents have taken to Twitter as their platform of choice, while some – like me – tend to prefer the more structured environment of posting on LinkedIn or blogging. Regardless of medium, the end result is the same – a leader whose organizational vision is aligned with their public message. There should never be confusion among the ranks as to what an executive stands for.


2) Outreach

In a world made smaller every day by technology, we can’t continue to operate on an island. The role of the CEO/superintendent now involves a proactive and ongoing pursuit of collaboration.

Here in my own backyard, I recently initiated the formation of the Central Wisconsin Information Technology Alliance (CWITA) with the idea of rallying local businesses to work toward some common goals in tandem with the K-12 and higher education organizations in our area identifying the needs we have as businesses when it comes to academic preparation for our job market.

Most of the CWITA members are experiencing a shortage of IT professionals for the jobs that are available. This is exactly this kind of dialogue that will need to happen on a national scale in order for sustainable communities to emerge in regions that are geographically or economically disadvantaged.

In school districts, it falls on the superintendent to foster these relationships and ensure that such partnerships are aligned with the instructional goals of the district. With so many options now on the table, it will be increasingly important for district leaders to focus on sustainable enrollment numbers by working with the community as a whole to better prepare all students for college, careers, and citizenship.


3) Agility

Just as technology has made the world smaller, it has also driven an unending need for “more” and “faster.” Executives no longer have the luxury and security of time on our side.

We must continuously review even the most granular details of our organizations to identify successful initiatives and areas of opportunity while assuring ourselves and our stakeholders that it takes time for the effects of change to become apparent. The last thing anybody wants is the “spinning wheels” culture that results from change for its own sake.

From a superintendent’s standpoint, it is now possible to break down attendance data by school, review assessment results or year-over-year trends, and drill-down into the budget to determine where additional funding is most sorely needed as well as where it is not.

This red carpet access to actionable information is empowering our district leaders to make better-informed decisions. Such responsibilities as talent management, disciplinary procedures, and instructional course corrections can be supported with analytical evidence, where in the past they might have relied on heavily filtered anecdotes.


4) Team-Building

Behind every successful executive is a strong leadership team. CEOs can no longer run even a small organization on their own. Although we remain accountable for every aspect of our company’s operations, it is all but impossible to play a significant role in every aspect of day-to-day operations.

In larger districts, superintendents often rely on their CTOs to manage complex technology needs, CFOs to act as fiscal fiduciary, and CAOs (chief academic officers) to manage the instructional side of things. Every one of these leaders must work cohesively toward the same objectives for the district to be successful.

While corporate CEOs (myself included) are struggling to find enough specialized employees to meet demand, superintendents throughout the country are dealing with a growing shortage of teachers and IT personnel. It’s now easier than ever for educators to research and pursue new employment opportunities in other districts and fields, as opposed to the “30 years and a gold watch at retirement” days of the past.

Just as I hope that working at Skyward remains an ambition for future generations of students, superintendents must continue to explore new ways to position their districts as destinations, rather than fallbacks. Finding the right people and keeping them is one of the objectives keeping these educational leaders up at night, and for some it appears to be working. We are only as good as the people who bring our vision to life. It’s up to all of us to adapt so we can meet the needs of the modern workforce.

Complacency is not a trait shared by many transformative leaders. Today’s best executives practice transparency in all areas of governance; collaborate closely with direct and indirect stakeholders; use data as a means to remain agile and proactive, even when it means abandoning the old way of doing things; and surround themselves with the strongest teams possible.

Speaking from experience, it’s not always easy to develop these traits, but it’s the only way to keep your organization moving forward in a rapidly changing world.


Cliff King Cliff King CEO Emeritus at Skyward
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