Importance of a Leadership Entry Plan

“Good is the enemy of great. And that is one of the key reasons why we have so little that becomes great. We don’t have great schools, principally because we have good schools.”

-Jim Collins, Good to Great

As we enter the season of applying, interviewing, and moving into leadership roles (new or upward movement) it is critical to have a plan. Leadership is challenging for both beginning and experienced school administrators. Schools have their own culture and identity including history, traditions, norms, and values. To help make a smooth transition, it is very important to respect the existing school culture that has been established over time. New principals endeavor to make a smooth transition into their new school communities; not honoring existing culture can put new leaders at risk. The key to a smooth transition is a well-developed entry plan.

An entry plan forces leaders to develop a vision, values, goals and beliefs. It challenges you to research the prospective school/district and staff. The goal of the research is to put yourself into a position to understand the school, community, students, and yourself. If you happen to already be in a leadership position, keep reading, because a 100 day plan to kickstart your year could help you establish a new vision and assess your progress.

I have found the process of developing an entry plan to be insightful, challenging and rewarding.  The staff and student decisions (and research) involved in creating the plan are based on core values and your vision as a leader.

There are going to be many challenges in your first year (and every year thereafter for that matter) and having an initial dialog with stakeholders, staff, students, families, and community members will help you establish the “big” levers versus the “nice to know” categories. Below are a few critical steps and examples to support your transition into a new leadership position:

Have a Cover Page

An entry plan cover page is often your earliest written contact with students, families, and other community stakeholders. It is a critical first step in going from your interview ideas to actionable items. This critical first impression will launch your vision and set the tone for your leadership.  Effective cover pages explain your goals and provide an action plan for the specific school district or school. They also serve to identify your action plan, so as to be visible and transparent. (Please note: a sample cover page appears at the end of this blog for your use).

Critical steps in an entry plan include documented objectives, a timeline of actions, meetings, and additional activities, e.g., classroom visits, listening tours, and document review. Detailing all of this in one plan will show the community that school employees are ready to lead with a clear plan of action.


Leadership Objective

  • Expand on current knowledge of the school district and its people as fully as possible in a brief period and outside of the daily management of crises and problem solving.
  • Develop objective that ensure a flawless opening to the school year and a smooth and orderly transition of leadership.

Organizational Objective

  • Review organizational structure, climate, budget, key work processes, practices, programs and resources to ensure alignment efficient and effective alignment with the educational, social and emotional needs of all students.

Public Relations Objective

  • Ensure multiple perspectives and voices are heard.
  • Establish a strong working relationship with the Board of Education.
  • Identify the key issues in the school system that will help inform the strategic planning process.
  • Build trust and confidence through open, honest, communication and positive relationships.

Strategic Planning Objective

  • Identify strategies for enhancing efficiency and effectiveness.
  • Assess the strengths and weaknesses of the district’s academic programs.
  • Assess the district’s current financial position.


  • Phase I: Pre-Entry (prior to first day of work) June – August
    • Design entry plan; provide written justification for the development
  • Phase II: Entry (first 100 school days) September– February
    • During first 100 days as an educational leader of your institution, how will your work revolve around the core entry plan activities? Although this will take place in concert with the day-to-day functioning of the school district, rely heavily on existing senior staff to maintain the daily operations of the district to give you time to focus on accomplishing the entry plan objectives. This will provide a foundation for the future success of the school district.
  • Phase III: Development of Next Steps– May
    • This entry plan will afford the opportunity to listen, observe and learn from a variety of community members while gaining an understanding of the local context of the city and the school system. Through this process, begin to formulate ideas and frame strategies to improve the school system so that you can increase student achievement for all students while simultaneously closing the achievement gap.

Possible Meetings and Interviews

Detail and then conduct a series of meetings and informational interviews with various community stakeholders, e.g., critical members of the school district, school community, and policymakers. The primary goal of these meetings will be to actively listen and gather input from a variety of perspectives. These interactions should be a foundation for authentic relationships and collaboration with an end goal of positively impacting all students. Before the close of each meeting, establish some routine communication protocols so that the conversation continues beyond the first discussion.  The most important part of an entry plan is engaging in purposeful efforts to listen, learn, and begin to develop plans in collaboration with the board and the community.

Types of meetings

Individual Meetings: School

  • Central Office cabinet
  • Director of Technology
  • School leadership
  • Central office assistants
  • Directors:
    • Health/PE
    • Fine Arts
    • Student services
    • Nurse

Individual Meetings: Community

  • School Committee Members
  • Teacher Union President and Vice President
  • Town officials
  • Police Chief
  • Fire Chief
  • Town Manager
  • Religious leaders

Focus Groups

  • Staff focus groups from each school
  • Related service focus groups from each school
  • Paraprofessional focus groups from each school
  • Family focus groups from each school led by PTO president
  • Students

Community Forums

  • School Committee
  • Community groups
    • MADD
    • Recreation department
    • Parents against bullying and cyber-bullying

    • Rotary
    • Senior center
  • Library director

It is important to have prepared questions for these meetings/interviews to focus the conversation on your entry plan objectives. A few questions I recommend are:

  • What are your general impressions of the schools in the School District?
  • What are the school district’s strengths and areas for improve?
  • What are the key issues that you think the school system faces? Which issues need immediate attention?
  • What is your assessment of the K-12 instructional program?
  • Before I prepare a long-range strategic plan to recommend to the school committee, what would you like me to know?
  • What has been the nature of your contact with my predecessor? How would you like to see it changed? How should it remain the same?
  • How effective are communications between the district/school and the community?
  • Describe the ways in which parents are involved in the schools and/or the school system?

School and Classroom Visits

Include school and classroom visits in your plan. Spending time in schools and classrooms provides the foundation for learning about the district. It also establishes relationship building when you openly share that you will visit classrooms in every school. Doing this shows others you are prioritizing your willingness to be visible and engage in conversations about teacher and learning.

Listening events, speaking engagements, and meetings in schools and communities:

In addition to the individual and focus group meetings outlined above, establish a series of listening events where the general public is invited to come and bring questions/concerns, or simply introduce themselves. These meetings should be held at schools and other community locations in order to provide a convenient and comfortable environment for interested community members.

I would also recommend a presentation of findings from the entry plan and a framework to create a strategic plan to implement said findings.  The entry plan report findings can be shared with the School Committee. The strategic plan that comes from the entry plan will guide initiatives, programs, activities, and benchmarks in order to move forward during the next 18 months of your leadership.

Document Review

The final part of your entry plan should be identifying the documents you plan to review during your first 100 days. This document review is aimed to identify the strengths and opportunities for improvement within the planning and management process.  Analyzing data from the document review will be essential for planning goals and next steps for the district.

I recommend including the following documents for review:

  • Administrative evaluations
  • Advanced Placement enrollment data
  • All current vision, mission, value, or building goal statements
  • Assessment calendars
  • Budget documents
  • Comprehensive District Improvement Plan
  • Collective Bargaining Agreements
  • Crisis plans and procedures
  • Curriculum Guides/Maps
  • Dropout and graduation rate data
  • Employee contracts
  • Employee handbook
  • Enrollment (current) and enrollment numbers from the past five years
  • Evaluation processes and procedures
  • Job descriptions
  • State assessment reports
  • Middle and high school athletic guidelines

  • Minority hiring data

  • Minutes from School Committee meetings for the past few years
  • Organizational chart
  • Personnel procedures
  • Press releases
  • Professional development plans
  • Program evaluations
  • Salary schedules
  • School Board policy and procedures manual
  • School Improvement Plans
  • Strategic Plans; District and School

Example Cover Page

“Seek first to understand, then to be understood”

-Stephen Covey

In the book The Seven Habits of Highly Effective People, Stephen Covey wrote, “Seek first to understand, then to be understood.” The purpose of this entry plan is to assist me in developing a comprehensive picture of ____ School District.  It is my hope that this entry plan will guide me in the process of understanding the ____ School District and strategic planning for the success of its students. This entry plan outlines the goals and activities I endeavor to accomplish during my first 100 days. It was designed based on Convey’s beliefs that the role of the superintendent is one of public service, and that the most powerful and sustainable educational systems are built from the ground up.

Covey went on to say, “The key to success is not to prioritize what’s on your schedule, but to schedule your priorities.”  Interviewing current stakeholders, reviewing school/district plans and documents, and developing a sense of the school to provide a basis for future goals, objectives and activities, are my top priorities in developing this plan and becoming part of the _______ School District and community.

At its core, this plan outlines the beginning efforts to ensure that teaching and learning is the district’s primary focus of every classroom, every day.  I firmly believe all students have the
ability to achieve at the highest levels if afforded the
opportunity. A successful partnership for school governance requires shared
commitments. ______ is an incredible place to live and the community deserves a world-class school system. This entry plan sets the foundation for making that desire a reality.

I will present a report of my findings to the school board, school administrators, and the community in September and then detail my next steps after the first 100 days.


Sign your name


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