Strategic Planning Check-up for Heads of School

Strategic Planning Check Up

By Jonathan Oleisky

Your independent school community is settling into the fall routine, and the academic year is well underway. Now is the perfect time to…review your strategic planning check-list and approach.

How will you approach your school’s strategic planning needs this year?

Every great institution (and we all should want to be one) should work under a three- to five-year strategic plan that guides the institution and positions it to attract and retain students, revenue and alumni and parent philanthropic support. The strategic plan is the road map, but like any successful journey, you need to be agile and ready to face whatever you encounter while getting to your destination. This is the strategic posturing piece, which is critical to achieving all that you’ve articulated in your plan.

For an excellent primer on strategic planning and posturing, check out “Strategic Planning is an Oxymoron” by Pat Bassett, retired NAIS head and founder and president of Heads Up. Written in his final year of his 12-year NAIS tenure, I would argue that it should be required reading for every Head of School at the start of the school year.

What’s on your checklist?

It’s the Head of School’s job to stay focused on the larger issues that will help grow and sustain his or her school. How can an effective Head of School continually balance the increasing multitude of daily tasks and review the strategic landscape from 30,000 feet?

The checklist approach to planning is a tried-and-true management method. It keeps you more productive, motivated, creative and so on.

And it keeps your strategy front and center and agile.

Need a refresher on checklists? Check out The Chronicle of Higher Education’s review of surgeon Atul Gawande’s The Checklist Manifesto: How to Get Things Right. Dr. Gawande’s Harvard Business Review podcast shows the parallels between the value of checklists in medicine and the educational arena.

A Head of School’s strategic planning list might include:

Short-Term – Fall/Winter Issues:

  1. Academics: Is your pedagogy aligned with your mission?
  2. Faculty and Staff: Are the right resources in place for the start of the academic year? Are your professional development and mentoring of new faculty and staff in place and being utilized?
  3. Facilities and Grounds: It’s open house season. Take a walk around campus and see it through the eyes of your visitors. Do you need a quick refresh?
  4. Fall Open House Marketing: While this might not seem strategic in nature, it’s critical to your school’s success that you’ve done everything you can to begin to fill your admissions funnel early in the process.


  1. Mission/Vision: Is your mission statement clearly articulated and is your Board in agreement with it?
  2. Value Proposition: Is your value proposition well defined for prospective and current families?
  3. Positioning: How clear is the position of your school in your local market?
  4. Enrollment Growth: Do you have an enrollment strategy? Have you identified the unique challenges of your market?
  5. Academics: What do you want your academic rigor to be? What do you want your students to learn? Is your program in line with your goals and objectives?
  6. Finances: Is your budget sustainable?
  7. Faculty and Staff: Do you have the right people in place to build a strong institution?
  8. Facilities and Grounds: Do you have a campus master plan that supports your mission and vision?
  9. Marketing:
    1. Research: Are you using qualitative and quantitative marketing research to identify the buying habits of your prospective families?
    2. Messaging: How do you tell your story? And what story are others telling about you?
    3. Admissions Engagement Marketing: It’s not enough to have a great story. What is your media plan to spread the word through both digital and traditional marketing?

Does your strategic plan test new ideas and approaches?

The independent school community is facing a host of market challenges. Fresh thinking is needed to move beyond the traditional solutions, many of which often re-enforce the status quo.

For example, how is your school dealing with the rising cost of tuition? Do you have an innovative, forward-thinking approach that offers parents a refreshing new way to look at the major investment of an independent school education?

Messaging about the value-adds to tuition is important. Don’t assume families know these. If you offer a host of afterschool activities, music or dance lessons, sports, homework help, etc., are you marketing that as offering parents “everything under one roof?” That’s a value-add that busy, stretched parents will love. Is there free before or afterschool academic mentoring by older students? Free lunch? Convenience and quality “extras” (without the extra cost) help to balance the cost of tuition.

Another key strategic planning issue is faculty investment and retention. Does your school offer highly experienced educators who demand success from their students and offer creative and battle-tested teaching methodologies? Do you pay your faculty well? You should, as they are the foundation that your school should be built upon.

For inspiration, check out how Head of School Matt Levinson of Washington’s University Prep  moved his school’s plan into collective, innovative action.

What is often overlooked in strategic planning?

Marketing is one of the most important, yet often forgotten, strategic planning issues. How well do you know your prospective audience? When was the last time you had an objective third party marketing research firm examine your quantitative and qualitative data? You have spent time and resources crafting a message for your school. Market research will tell you what message the market is saying. They may very well be very different. Knowing the answers to this will guide your marketing messages and strategy.

What are your strategic planning tips and tools to keep you on task?

Jonathan Oleisky is President and Founder of Kalix Marketing.




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Jonathan Oleisky

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