Why Is Great Strategic Planning So Difficult? Five Challenges | Joel Backon | 17 Min Read

Traditionally, there are several reasons why independent schools undertake a new strategic plan:

  • New Head of School
  • Haven’t written one in many years
  • Ten-year accreditation coming up in two years
  • Considering a change in direction (high school opening a middle school)
  • Upcoming Capital Campaign
  • A major transformation of the program (integration of SEL, DEI, PBL, and CBE)
  • Regular planning cycle

Today, there is another reason that was not considered as recently as last year: considerable change in the external environment. The arrival of COVID-19 forced schools into a scramble mode to finish the 2019-20 school year. Now the 2020-21 year is in full swing, and schools are still in a mode that was designed to be temporary, at least according to the communication that goes to school community constituents. At what point do we decide that some of the programmatic and pedagogical changes we are making are not temporary, but Phase I of a new approach to teaching and learning that is more blended and flexible in nature, that appeals to the individual needs of students and fosters a mindset that is based upon mastery rather than relative achievement? The most reasonable response would be that there is no time to write a plan now, even though it might be very useful. 

Strategic planning is really more about questioning and deep reflection than it is about producing documents. One can always transfer great thinking into written plans and roadmaps, but the impetus for great thinking and brainstorming is harder to come by unless we are shaken to our roots by a major disruption. The next part of the process is to formulate education strategies that are unique to your school and have measurable outcomes. It is the most difficult portion of the process for school leaders in light of the challenging characteristics of the independent school world.

Let’s examine those characteristics and call them Strategic Planning Challenges. There are five, and each colors the nature of the strategies you will define:

  • The Inversion Challenge: Most organizational success is measured by outcomes. Corporations are driven by profits, the outcome of financial success over a period of time. Inversion of the success formula occurs when schools shift focus to make inputs and process a priority over outcomes. What are some of the conditions that push schools into an input- and process-oriented mode rather than an outcome orientation?
    • Inputs are easier to verify than outputs
    • Increased litigation making schools more risk averse
    • Parental micro-management
    • A more complex regulatory environment (that defines inputs)
    • Very selective admissions processes (inherently input-specific)

Because most school leaders are practitioners at heart, the best way to address these external pressures is to head off every possible case through policy and practice. Such an approach creates thick and complex handbooks that grow in size as each new situation arises. It also shifts our attention away from student outcomes. What we want for our students has little to do with litigation and regulations unless we are negligent, but it has much to do with parents and admissions. We’ve all heard about “helicopter” or “lawnmower” parents in the current culture, creating a predisposition for interference in school processes. Many parents come from the corporate world, and therefore know that tinkering with the processes will change outcomes if those outcomes are almost universally accepted (such as corporate profits). But the outcomes for independent schools are subject to debate. Just ask a group of parents. Therefore, the tinkering with processes may be misdirected since the goals for outcomes are a moving target.


Independent schools, because they select students, invert the measurement of success by focusing on the quality and quantity of the input. How often have you heard the Admissions Director announce at an opening faculty meeting that this year’s incoming class is the best in recent history? And our selectivity percentage has improved, another piece of inverted news. Focus on the admissions process excuses us from output disappointments. If we followed the teaching and learning processes and some students were unsuccessful, then it must be their problem because our processes are successful most of the time. This is not to argue that process is unimportant, but rather to say that a process for a group of students is likely to produce some failures. If we wish to preserve the process, leading to great outputs, then we may have to consider processes that define selecting something unique for each student. To avoid unnecessary hand wringing, we need to find reliable measurements of success during the student experience at our schools that lead to improved outputs. What will our students do upon departure/graduation to thrive in the future? What kinds of programs will create the conditions for students to demonstrate expertise and mastery to others? How do we help students promote themselves to those seeking such skills and expertise? These are strategic questions with answers that might help counter the Inversion Challenge.

  • The Advancement Challenge: …follows from The inversion Challenge and is also dependent on inputs. To increase the endowment and annual fund, the school needs to accept a significant number of families that have the ability to contribute more than student tuition, to give back to the school. The realities of the current global economic structure dictate that financial prowess is more a result of assets than income. So, addressing the Inversion Challenge creates a problem for the Advancement folks. Even if the school focused on the most disadvantaged financial aid candidates in the admissions process and helped those kids become highly successful, their success would be measured by income potential, not assets. Thus, we have a dilemma. The ability to create the optimal and diverse conditions for student learning outputs works against our ability to ensure financial stewardship.

    There is, however, another challenge for Advancement, and it is input-based as well. Many schools operate using a deficit funding model. That means that net tuition revenues are insufficient to cover the operating expenses of the school. As a result, annual fund contributions and/or endowment draws are necessary to keep the school financially solvent. Forty years ago, some schools did not have a formal budget. Tuitions increased annually from 3-6% and expenses were covered one way or another. It was a scary process, but at the time, campus communities were far simpler than they are today. The routine of living from year-to-year on tuition revenues and parents’ fund contributions is risky, as we are learning this year. Unforeseen circumstances can mean the end of a thriving school community. What can schools without large endowments do to bolster long-term financial stability? Is there a philanthropic source of funding, and if so, won’t it be incumbent upon your school to have unique qualities to attract those funds?

    While the most enlightened Advancement offices are very good at painting a picture of the school’s future and attracting funding from loyal and happy alumni to achieve the longer-term goals of the school, there are obstacles. First, some Advancement offices have shifted focus away from longer-term outcomes to inputs and processes under the guise of guilt and obligation. The pitch begins with the cost of educating your child and the tuition you pay. After pointing out that tuition covers perhaps 65% of the cost, there is a request to close that gap for your child and the children of those who cannot afford to close the gap. While some families may respond to the pitch, it does not create a level of excitement that would retain that family in the school community after their children have graduated. Parents have a brief relationship with the school, but alumni have a much longer relationship. Second, some of the most financially capable alumni and families may contribute generously, but with strings attached that are often not consistent with the longer-term plans of the school. Schools can refuse such gifts, but they do so at their peril, particularly if they have limited financial resources.

    The bottom line is that the Advancement Challenge is perhaps the most consequential for the survival of your school. Expenses continue to rise more rapidly than tuition, and the burden for making up the gap falls to the Advancement office. They, in turn, will influence Admissions strategies because of the need for fiscal support. That, in turn, impacts the school’s ability to meet its longer-term diverse student profile. So, Inversion and Advancement have a symbiotic relationship.
  • The Mission Challenge: There are approximately 2,000 independent schools in the U.S., and 1,900 of them have almost identical mission statements. That means we certainly understand the essence of independent schools, but likely do not understand, or at least communicate, what makes our school special. Instead, the philosophy is: if one wants to attract the largest audience, then the mission must be broad enough to include all potential applicants. Broad missions reduce the probability of applicant self-selection and therefore put pressure on your admissions team to find the best matches from the entire applicant pool. They also communicate that you are not unique, that you are like everybody else. “Give us the most talented kids, and we promise that they will be more talented when they leave us.” So what. Did I need to spend $150,000 to essentially maintain the status quo?  A targeted mission statement tells people who you are as a school and brings you the best applicants whose interests match your strengths.

    Another challenge with mission statements is they define what the school will do rather than the results a student might expect. Again, this is an issue of inputs and control. Schools know what they can and will do, but cannot be sure of the student response. Therefore, the tendency is to talk about what the school is in a mission statement rather than what students will achieve by attending your school. The shift in focus creates a misalignment between mission and program, and it demotes your academic program to a lower standing than the values of your community. Both are important and connected but consider the implications of a school valuing community over the program. While families say they love the communities created at independent schools, at the end of the day, student results take the cake. The family of a student who shows strong growth in social-emotional maturity, has many friends, and is happy, but does not matriculate at a top tier college will likely consider your school experience a failure. It is one of the reasons for the tuition backlash during the pandemic. If one removes the community component from teaching and learning, the educational experience is exposed and undervalued. It should not be. The goal of your program is to create a love and passion for learning that crosses disciplinary boundaries and integrates all of the programs in the school. In short, the program drives and defines community.

    N.B. Broad mission statements were quite acceptable when independent school clientele were primarily wealthy and powerful. Even though schools have become more diverse, many schools are still governed and influenced by the traditional constituents, and they support a broad mission because it ensures a sufficient number of applicants. The biggest challenge for our schools over the next twenty years will be to innovate in the context of societal needs: leadership and cultural needs for equity. There will be resistance from the camp that has experienced great success in the traditional paradigm.
  • The College Prep Challenge: College Prep schools may no longer be relevant. Last year, 66% of all high school graduates went to college. In 1970, it was 26%. Colleges, as a group, are approaching commodity status, reinforced by Labor Department stats that show the impact of an undergraduate degree on lifetime income. If anything, the challenge today might be called “The Elite College Prep Challenge,” and it creates one of the biggest constraints to effective strategic planning because independent schools are holding very few of the cards. Elite colleges have done an excellent job of marketing their brands and the benefits of attending their schools. They have then made the selection process so exclusive and prescriptive that it has raised the anxiety bar for most students and their families, pre-empting the most significant programmatic reform in our schools. The theory is: if students were successful last year (substitute any prior year) in the school’s existing program, then that program should remain intact in every subsequent year. No family that values elite higher education will want your school to change anything (unless perhaps their child is not accepted at these schools).

    This is not an argument to undermine or undervalue the college experience, particularly at an elite college. If the goals of your school are to make students independent and lifelong learners who have a passion for something that will contribute to the betterment of society (that is possible in a capitalist framework!), then many of the rationales for elite college experiences fall away. Connections are less important for those who make their own opportunities. Undergraduate prestige is nice to have but really matters for entry into a few traditional professions and the academy. Given that we haven’t identified half of the occupations that will exist in 30 years and don’t have a clue regarding the structure of work or the workplace at that time, planning for traditional financial security seems like a waste of energy. Better for independent schools to step up to the plate and argue that preparing students for anything they might encounter and equipping them for success seems a more prudent strategy than following the traditional path that has 59% of people in their 20s living with their parents and unable to obtain the kind of job to which they had aspired.

    The issue here is the purpose of your school. Are you preparing students for the next major step in their lives, another academic experience, or are you preparing kids for a broader growth experience (as communicated in your mission). If one looks at the offerings at most of our schools, it is clear that the variety and number of programs speak to the whole child, in addition to the college scholar. Many schools describe their goal as a group of young adults who are good critical thinkers and communicators, creative problem solvers, empathic listeners, and implementers of equitable policies. If so, the strategy has little to do directly with college, even if it is the next step in the education progression and will, in theory, further develop what you have helped students learn. From a strategic standpoint, the question becomes whether you articulate what you are all about and what you think will attract families that can afford to attend and further help the school financially. Both might be successful strategies. One speaks to the Challenge of Equity. The other does not.
  • The Equity Challenge: We used to confuse equity with diversity and inclusion. Yes, diversity and inclusion contribute to equity, but the essence of equity for us lies in our academic programs and communities since we are schools. The messages we send in those programs are the ones that will resonate most with our students. If there is a cultural reason for independent schools to innovate and reimagine their academic programs, it is because of equity challenges. Some of these issues don’t only apply to the many categories of traditionally disadvantaged students. They apply to all of our students. Meeting kids where they are, allowing them to progress at a pace that is comfortable and satisfies their interests and passions, and creating programs that give every student a sense of dignity is the essence of equity. Consequently, we have to question the scope and sequence priorities of our curriculum, the focus on content developed or written by white European males, the emphasis on teacher-directed learning, and Carnegie Units for seat time. We should reexamine “tracking” or multiple levels of the same course. We have to question our grading practices. We have to ask ourselves how to handle class discussions when some students are unable to process questions as quickly as others (being rewarded for speed rather than deep reflection). A commitment to equity is a strategic position that entails many operational changes. If we are unwilling to make those changes, to provide students with opportunities for learning that meet their needs, it doesn’t matter what we say about equity on our school websites. The emperor will have no clothes.

    Equity is all about meeting students where they are and meeting their needs by allowing them to move at a manageable pace. Doing so requires empathy, and that is a quality that translates to almost any equity issue one might encounter. If I truly listen to another person’s narrative and try to feel what they feel, I can have a constructive conversation because I am meeting them where they are. Some of the structure and policy of an independent school (or many other organizations) work against equity and that is why tweaking or enhancing existing programs, while perhaps successful in the very short-term, will not yield any meaningful transformation of thinking or attitudes. What is the potential damage that might occur from a change at the margins? If we espouse the language of equity, but our policies and traditions remain intact, then our students will receive mixed messages. The result of those mixed messages will be varying levels of cynicism, increasing with the age-level of students. This is not a novel concept. Ted and Nancy Sizer wrote about it in The Students Are Watching: Schools and the Moral Contract (1999).

One might ask why affordability is not one of the five Challenges. It is part of the Advancement Proposition since those folks labor under the constraints of affordability. Those CFOs that took Cost Accounting in college know that school expenses are divided into fixed and variable costs. The largest fixed cost is the physical facility itself and the largest variable cost is labor and benefits. In between are a multitude of expenses that fall into either category and some could be disputed. Technically, a variable cost can be controlled through sound fiscal management, and the most common method of control is reducing labor costs. Independent schools, however, sell small class sizes, low student-faculty ratios, and dedicated advising resources so a reduction in labor cost is often quite difficult. Some expense items may change categories based on your mission and strategy. For example, professional development is often considered a variable or discretionary expense, meaning that when tuition revenues are down and budgets are tight, PD may be cut. But if perpetual PD as a support for sustainable change is fundamental to the culture of the school, then perhaps it is a fixed cost. Ironically, when times are tough, PD increases in importance. PD impacts every facet of the school and therefore the strategic planning process should be driven by PD in ways that will lower the barriers of the Five Challenges.

When we do strategic planning, we often collect data about our school. Some of that data can be misleading because it is incomplete or out of context. Case in point: We have a student-faculty ratio of 6:1. We need a plan that reduces expenses but maintains the high level of personal contact we provide. Moving to a ratio of 8:1 appears unacceptable because it will reduce the quality of personal contact, so we think. But that is only true if nothing else changes. The whole idea of strategic planning is that everything is on the table. IF we rethink the daily schedule, rethink the requirements of the program (perhaps a revival of skills to complement our prior emphasis on content), and identify opportunities for merging academic silos (Humanities, STEAM, etc.), then an 8:1 ratio might provide an experience of equal or better quality compared with the current 6:1 ratio. 

Those schools that rethink the Five Challenges are the ones that will realize existential success. They speak to the “value” of independent school education in 2020. Value is a result of providing a customized experience for each student, similar to a personal shopper. To provide such a service, schools must be committed to continuous growth and improvement, and that is driven by continuous professional learning. Any planning process starts with professional learning and creates the conditions for continuing that learning. Thus, it becomes a top priority for every school that wants to distinguish itself from others. Not only do students deserve a great program, but adults in the community do as well. 


Be bold and attack the Five Challenges aggressively. Have the difficult conversations that result from the challenges. Develop a consensus that is capable of defining who you are and what you do. These are ongoing conversations that, at important points in time, you can commit to writing and add a cover that says Strategic Plan. On the first page, including the explanation that says, “our programs and initiatives are subject to change on an annual basis, but the school’s strategy is a living, breathing assessment of the present and future, with a longevity that is subject to reinterpretation.” One might think you were talking about the U.S. Constitution.

Joel Backon

Joel Backon has been the Editor of Intrepid Ed News since its inception in January 2021, responsible for all educator content on the website. He joined the OESIS Network, owner of Intrepid, in 2019 as Vice President. Joel spent much of his career at Choate Rosemary Hall (CT) where for 27 years he held founding roles in Information and Academic Technology, as well as being a classroom teacher, curriculum designer, coach, dorm head, and student adviser. Prior to Choate, Joel spent 15 years in the printing and publishing industry educating printers on how to maximize their strengths and minimize weaknesses. He has crusaded to achieve consensus on the question of why we educate kids in an effort to meet the learning needs of every student.

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