Changing of the Guard

A new generation of educational leaders.

GUEST COLUMN | by John Jennings

CREDIT Skyward.pngMillennials have already left an indelible mark on the education system. Now, the largest generation in the workforce is poised to break into the ranks of school district administration, and the K-12 community should take notice. Change is here. These are the highest of the high-performers from a group that has spent more than a decade shouldering the burden of negative labels. This was supposed to be the generation of lazy, disloyal, and technology-obsessed ingrates, too focused on themselves to understand how the world worked. But something happened along the way.

A Steady Progression Toward the Superintendency

The teachers came first. Millennial educators brought fresh perspective to a world steeped in tradition. Orderly, linear classrooms were transformed into friendly, collaborative learning spaces. The typical lecture-assignment-grade routine gave way to new, student-driven instructional models.

This was supposed to be the generation of lazy, disloyal, and technology-obsessed ingrates, too focused on themselves to understand how the world worked. But something happened along the way.

Soon enough, these millennials worked their way up to the principal ranks. Their spirit of collaboration, risk-taking, and change pervaded school culture, as traditional top-down management styles were replaced with a more empowered work environment.

Even as millennials continue to establish themselves at the middle management layer of school districts, those who straddle the Generation X line are ready to take the next step into assistant/deputy superintendent roles and eventually the superintendency itself.

Key trait of the new guard: Defined autonomy. Provide the vision and a set of guidelines, then trust your people to do the right thing. Defined autonomy is the preferred leadership style of and for millennials because of its focus on agility, trust, and ownership. The leaders of this generation understand that if they are going to encourage risk taking, they must be willing to stand by their team’s mistakes and successes in equal measure.

Natives Take Over the Technology Department

Gen X technology leaders have seen their role change more than anyone else in the education system. Job responsibilities that once featured projector troubleshooting and knowing which plug went where on the TV cart now encompass community-wide infrastructure, enterprise app management, and 1:1 initiatives. It would be a mistake to discuss the role of the millennial technology leader without a deliberate hat-tip to those who paved the way.

The new guard of district tech executives, despite being internet natives, finds themselves in a very similar situation. They graduated from high school in an age when smart phones didn’t exist and “social media” meant MySpace. Tech leadership positions have never been kind to complacency, which plays right into that millennial itch for continuous growth.

Key trait of the new guard: Conditional loyalty. Millennial edtech leaders are more likely to view technology as a core element of job function. They will be vocal advocates for brands that deliver a positive user experience for them and their stakeholders, but they won’t hesitate to jump ship if a vendor fails to deliver on expectations. Every edtech market is competitive now. If you let a millennial down, it’s not difficult for them to find someone who can provide similar services (and do it better).

Making Waves in the Business Office

The most dramatic generational divide can be found in the behind-the-scenes circles of school finances and human resource management. In conversations with district leaders, the cultural disconnect between this area of operations and the rest of the district is a recurring theme.

New-guard business leaders have made it this far because they know how to get the most out of the tools available to them. They’ve come in with a mission to eradicate inefficient, manual processes and bridge the divide between the school’s educational mission and the people who keep it running.

Key trait of the new guard: Systems thinking – School districts have gotten a bad rap for their silo mentalities and bureaucratic roadblocks. The millennial generation of school business officials is hoping to change that by taking a systems-thinking approach to otherwise specialized jobs.

It’s rarely a good idea to stereotype a demographic group, but to anyone who has followed the progression of the K-12 workforce, it’s hard to deny the distinct patterns that have emerged. Each generation leaves a unique impression on the education landscape, and we’re about to find out exactly what the millennials’ legacy will be.

John Jennings is the Digital and Social Media Manager at Skyward. Write to:


    Leave a Comment

    %d bloggers like this: