A Millennial’s View: How to Transform Independent Schools into Modern Workplaces

Editor's note: To go along with this blog post, NAIS Director of Instructional Design and Technology Kelsey Vrooman interviewed six millennials for their thoughts, including:
  • Adrienne Gifford, Open Windows School (WA)
  • Jordan Wright, Rabun Gap-Nacoochee School (GA)
  • Tom Taylor, Breck School (MN)
  • Bianca Anderson, Border Crossers
  • Bill Selak, Hillbrook School (CA)
  • Michael Goodman, PhD student in Student Affairs at University of Maryland, College Park
You can watch the interviews embedded throughout the post.

I’m 35, putting me at the leading edge of the millennial generation. Since I was 25, I’ve been an independent school educator, teaching civics and history to middle schoolers. After a short career in government contracting, I came to teaching because I wanted to make a difference in the world. 

I have thrived as a teacher in the independent school environment, where I have been able to work with kids in a small classroom and develop meaningful relationships with students, families, and staff. A particular pleasure has been hearing from former students majoring in political science in college and even starting civics-oriented clubs at their schools. I delight in the angelic sound of “Mr. Stribling, you were right about…”
 
In the 10 years since I began my teaching career, I’ve had many conversations with my peers about what independent schools can offer millennials: freedom to develop and tweak curriculum, genuine gratitude from parents of graduates, and collegiality of highly educated fellow faculty.
 
Over the years, we’ve also discussed the frustrations of navigating a profession in the throes of change — one that often leads to burnout after a few years. Whereas previously a teacher with leadership aspirations could rely on teaching for several years, then becoming a dean or division head and possibly heading their school, today’s aspiring leader feels pressure to be an innovative classroom teacher out of the gate while struggling with an uncertain path to leadership.
 
From our talks, I know the next generation of teachers values four key attributes: being mentored, learning from peers and colleagues, improving themselves to have impact, and achieving financial security. By making these a priority, independent schools can continue to welcome new educators.
 
1. Millennials want to be mentored.
 
Millennials thrive with “a roadmap to success and they expect their company to provide it,” according to the Harvard Business Review. For independent schools, it would be helpful to have an experienced member of the school guide us through the formative years of our careers. At my current school, The Hill School (VA), a JK-8 school of 225 students, teachers new to the school are assigned an administrative contact to meet with once a week for their first year.
 
In a study by Deloitte, 68 percent of millennials who have a mentor stay with their company for five years while only 32 percent of millennials without mentors will last as long. A shining example of this mentorship was my first division head. He checked in with me every morning to fill me in on news and allow me to ask questions. Even quick conversations in the hallway gave me crucial feedback on which I could act.
 
On a more formal level, the Shady Hill School (MA) offers a structured teacher training course for new teachers. This gives apprentice teachers practical experiences by pairing them with an experienced teacher to support them at the beginning of their careers.
 
And mentoring is not a one-way street. Millennials can demonstrate to faculty and administrators the latest methods of technology integration as well as new pedagogical theories. This sort of reverse mentoring is a win-win for relationship-building within schools. By giving millennial teachers opportunities to lead curriculum change, pioneer new programs, and revitalize existing traditions, a school benefits from in-house professional development for the veteran teachers and accelerates the leadership abilities of emerging young faculty.

 
2. Millennials want to learn from peers and colleagues.
 
Millennials are a highly collaborative generation; we want to be part of and contribute to a larger community. I believe my greatest professional successes have come when collaborating meaningfully with my peers and colleagues, including Mike Wipfler, the middle school history teacher at The Hill School.
 
I think it’s incumbent upon school leaders to find ways to blend the talents and experience of baby boomer employees with the ambitions and talents of millennials. For example, schools can create teacher teams or committees to re-envision important aspects of the school experience, such as restructuring the school schedule. Holiday programs and end-of-year traditions, too, can be reimagined to build stronger parent engagement and student buy-in. We know that each independent school survives based on what separates it from other schools, and having young faculty willing to keep their schools relevant is a golden opportunity for everyone.
 

3. Millennials want to improve themselves to have impact.

 
Millennials tend to be highly self-critical. As a result of social media connectedness, millennials face a constant, “ruthless comparison” to peers, says Emerson Csorba, a workplace culture consultant and director of Gen Y, Inc. As young professionals, we live in a state of constant anxiety about doing more and improving our resumes. We join Twitter to participate in personal learning networks, apply for National Endowment for the Humanities grants, attend un-conferences where the content is developed and shared by the participants, and, in general, take professional development very seriously.
 
Does this constant drive for meaning and improvement mean millennials desire a traditional position of authority? Not necessarily. Rather, authority in a millennial’s eyes comes from what a colleague once called “a continuum of say.” The continuum measures the level of “say” a teacher has on important matters, ranging from “follow the orders,” “input is welcome,” “input is necessary,” and “make the decision.”
 
In the school context, consider the level of say a teacher has about curriculum changes, faculty meeting agendas, or grading policies. The more opportunities we have to affect the way our school works, the better we feel about where we are and the more likely we are to stay there. This means that schools should consider ways to help millennial faculty ascend to leadership positions sooner. Instead of waiting for administrators to retire or go to other schools, heads ought to create administrative internships to allow aspiring deans and heads to learn how to be effective administrators. A leadership identification program that actively looks for potential leaders among the faculty will give millennials the confidence that their hard work will be recognized and rewarded.
 

4. Millennials want financial security.

 
Millennials don’t adhere to traditional measures of life success. They typically rent rather than buy homes, and they choose to start families later in life. My wife and I are a good example; we just welcomed our first child last year at age 34. Millennials also have high levels of education, and the most student loan debt of any generation. Since 1980, public and private university tuition has tripled and the average college graduate has a loan debt of $30,000 (80 percent of a young adult’s average income).
 
Independent schools can improve their ability to attract millennials by adjusting starting salaries to account for our massive student loan debts. Such debts prohibit us from relying on traditional “grind it out” methods for career advancement to pay off loans, buy a house, and save for retirement. Independent schools are in prime position to meet these needs. They can look to the federal government’s program of student loan forgiveness as a good example. What better way to attract and retain great teachers than providing loan forgiveness after five or 10 years of service?
 
Schools should also consider affordable housing options. Boarding schools have the advantage of on-campus housing. For day schools, that is not usually the case. At The Hill School, the leadership has made a concerted effort to attain affordable housing for teachers in and around Middleburg as a way to attract top talent — unheard of for a day school. This benefit required substantial fundraising at the board level and appreciating the economic reality of young teachers. Without it, it would be nearly impossible to afford to live in Loudoun County without a spouse who earns a high income. Or great teachers would have to live elsewhere and face a long commute — a significant deterrent for most people.
 
How School Leaders Should Proceed
 
I believe millennials have a crucial role to play in the future of independent schools. Historians Neil Howe and William Strauss, the creators of the millennial label, call us the “next greatest generation.” To realize the full potential of their newest and future teachers, school leaders may need to adjust traditional lines of thinking about the independent school and see it as a modern workplace. To continue to lead in education, heads will need to recruit and retain enough teachers to ensure that all students get what they deserve: a caring, loving, and effective adult to guide their learning,” as Jonathan Cetel writes in Forbes. Regardless of which generation we belong to, we can all agree on that.

 
Author
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William Stribling

William Stribling is a middle school teacher and director of summer programs at The Hill School (PA).