This article has been updated to reflect 2026 data and recent developments.
Most of us like to start a project and see it through from start to finish. Signing on to run a going concern is a pretty safe bet. But what about tackling something that will make enormous demands on your abilities, energy, and experience but which has a lot of risk? Such as taking over a struggling private school?
Taking over a struggling business entails a lot of risk. However, you have talent and experience. So, let's examine what's involved in investigating a head of school position at a struggling school before you sign on. Here are eight keys to a successful business turnaround.
First, let's agree to define a struggling school as an institution with financial difficulties. Once you understand that you will have to do some hefty lifting in raising money, that will help you focus on what has to be done. The truth is that most struggling schools didn't arrive in their present condition overnight. This is a train wreck that the previous head of school and the board saw coming for several years before now. Things have unfortunately gotten to the point that either the school gets turned around or it closes its doors for good.
Reasons why the school is struggling
Let's look at some of the reasons why a school finds itself facing difficult times.
Its business model is flawed.
A flawed business model usually results from the trustees and administration implementing programs and structures that do not meet the needs of potential families and applicants. For example, if the school clings to old-fashioned, outmoded ways of teaching and managing staff, it will have a limited appeal in its market area. There could be philosophical reasons why the school has let itself get into this situation. Be alert to those. The solution could be a straightforward course correction or a more complicated revamping of the school's mission. Assess what is flawed. Determine how you can fix it.
In 2026, reviewing enrollment patterns and long-term financial sustainability is especially important. The National Center for Education Statistics provides data on private school enrollment that can help administrators evaluate broader educational trends. Schools can also review How Sustainable is Your School? when assessing their financial and operational models.
It didn't market itself effectively.
Is the school using social media to get its message out? Is it still marketing itself solely with printed materials and local advertising? If so, insist on hiring a marketing professional. That can be a member of staff or a consultant. Make sure you engage an experienced professional. You will need that professional expertise to produce results quickly.
In 2026, schools should also evaluate their visibility in search engines and AI-assisted search results. Marketing the Small Private School: The First Steps offers additional guidance for schools with limited marketing budgets.
It wasn't managed properly.
Educators are not necessarily good at running a business. They know how to teach, and some even know how to manage a staff of teachers. But that does not mean that they understand finances. Hire a financial professional with the competence and expertise to alert the head of the school and the board of trustees to situations before they bankrupt the school.
The National Council of Nonprofits provides guidance on board responsibilities and financial oversight that remains relevant to private school governance in 2026.
It didn't invest in the future.
Whether it has deferred maintenance or has put off enhancing curriculum and adding specialist teachers, a school that has not invested in its future will present its new head with significant fundraising challenges. Scope out those challenges as part of your due diligence.
These four reasons cover most of the more common situations. But there are others. You'll know them when you see them.
The most common reason why nonprofits fail is a lack of funding. Nonprofit organizations cannot fulfill their missions without adequate funding. Of course, many nonprofits get used to making a lot happen on a shoestring budget; however, that doesn’t mean fundraising shouldn’t be a top priority. Source: instrumentl
In the following video, experts give strategic advice on marketing your school.
Preparing for your interview
When you interview for the position, be sure to ask tough questions of the board. Was it a matter of the previous head of school staying on after his sell-by date had long passed? Was their marketing plan solidly rooted in the 1990s? These two factors alone can drive away otherwise loyal families and fail to attract new ones.
You must assess the board's short- and long-term commitment. This is a different kind of interview situation. Usually, you are trying to sell yourself to a prospective employer. In this case, the school has to sell itself to you. So, don't hold back when it comes to asking the tough questions. It's better to know the challenges before you sign on.
You are realistically looking at a three-year plan to stabilize the school and begin to get things pointed in the right direction. Will the board fund a three-year short-term plan to make that stabilization happen? It will have to spend some serious money on marketing and admissions personnel. These professionals must be willing to work harder than they have ever worked. Just like you will have to work harder than you ever imagined you could. Is success and appetite for hard work part of the board's DNA?
The board will also have to commit to implementing a new marketing strategy. That will probably mean recruiting trips both at home and abroad. Review the school's website carefully. Does it entice prospective parents to send their children there? Does it have dynamic content? Is social media part of the outreach? These are tools any enterprise needs to be successful in the 21st century. Effective marketing, which includes websites and social media, does not come cheap. Is the board prepared to invest in these modern marketing tools? Do they 'get it'?
Lousy management often occurs because the lines of authority and accountability are blurred or non-existent. Compliance and accountability are huge issues in corporate governance these days. Years ago, a board could almost be a rubber stamp for whatever the administration wanted if everything ran smoothly. No longer. Does the board have the stomach to repair the damage from years of bad management, which got the school into its present state of affairs?
In 2026, the National Association of Independent Schools offers guidance on governance, strategic leadership, and financial sustainability for independent school trustees.
The article Developing A Strategic Plan also examines the importance of long-term planning.
What about their alums? Have they been enlisted to help preserve and protect their alma mater? Have they been reminded frequently that their school gave them a great start and that they need to step up and ensure that future generations enjoy the same fine education and experiences they received? Was the most recent Annual Fund Drive successful? What about capital gifts? Funds for scholarships and financial aid?
This video examines why some not-for-profits fail.
After the interview
After you have been interviewed and it is clear that the school wants you, consult with a close friend who is a successful business person. Ask for her assessment. She will think of things you, as an educator, might have overlooked. Explain your take on the situation. Lay out your plans and goals. When the school offers you a contract, have your attorney review that contract carefully. You will need some safeguards built into your contract. If you don't get those, walk away from the struggling school. It will continue to struggle. But without you.
In 2026, reviewing financial records, governance practices, and enrollment projections remains an important part of evaluating a struggling school. How Exposed Is Your School? examines additional operational risks that school leaders should consider before accepting responsibility for an institution facing financial difficulties.
