Innovative Leadership and Digital Learning

Dr. Matthew X. Joseph – Follow on Twitter @MatthewXJoseph

The Importance Of An Entry Plan For Leaders

“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 because schools have their own culture and identity that includes its 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 want to make the smoothest and best possible transition into a school community and not honoring the culture can put new leaders at risk. I believe the key to this transition is a well-developed Entry plan. I first created one in Natick and then created one while in Boston College for superintendents.

An Entry Plan forces you to develop your vision, values, goals and beliefs as a leader.  It challenges you to research the prospective school/district and staff. The goal of the findings are to put you in the position of understanding the school, community, students, and yourself. If you are already in a leadership position, keep reading because a 100 day plan to kick off the year could establish your new vision and assess your progress. 

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

There are going to be many challenges in year one (and every year after) and having this dialog will help you focus on the “big” levers and the “nice to know” categories. Below are a few critical steps followed by my demo superintendent entry plan.

  • Develop and implement an entry plan. (“Hit the ground learning not running)
  • Communicate the reasons for your decisions whenever possible.
  • Make all decisions in the best interest of your students.
  • Supervise all personnel in a fair, firm and consistent manner. Be visible.
  • Respond and follow-up quickly. Implement changes slowly. Lead by example.
  • Practice good time management. Choose your battles wisely.
  • Discuss issues rather than personalities. Respect confidentiality.
  • Listen more than you talk.
  • Keep the school committee informed about potentially
  • Do not infringe upon school committee prerogatives.

Tip: Have a 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 Eagle School District.  It is my hope that the entry plan will guide me in the process of understanding the Eagle School District and strategic planning for the success of its students. This Entry Plan outlines goals and activities to be accomplished 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 also said, “The key to success is not to prioritize what’s on your schedule, but to schedule your priorities.”  Interviews with various individuals and groups, surveying current stakeholders, reviewing school/district plans and documents, in an effort to develop a sense of the school and provide a basis for future goals, objectives and activities are my top priorities in developing this plan and becoming part of the Eagle School District community. 

At its core, this plan outlines the beginning efforts to ensure that teaching and learning is the district’s primary focus and occurs in 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. Eagle County 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 Eagle School Board Superintendent, the school administrators, and the community in September and then detail my next steps after my 100 days have past.

Matthew X. Joseph Ed.D

Eagle School District

Tip: What follows should be your detailed plan

Entry Plan


Matthew X. Joseph’s Core Values:

  • Educate the whole student {Spirit, Mind, Body}
  • The core of all decision-making is made in the best interest of students.
  • Every student is entitled to a rigorous education.
  • Student achievement is increased by focusing on the instructional core – the relationship among the teacher, the student, and the content
  • Student achievement is increased through the collective responsibility of all teachers for all students.
  • Trust
  • Collaboration
  • Open and honest communication


The Entry Plan outline has three phases:

  • 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 my first 100 school days as superintendent, my work will revolve around the core entry plan activities. Although this will take place in concert with the day-to-day functioning of the school district, I will rely heavily on existing senior staff to maintain the daily operations of the district to give me time to focus on accomplishing the Entry Plan objectives, which will provide a foundation for the future success of our school district.
  • Phase III: Development of Next Steps– May
    • This Entry Plan will afford me 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, I will begin to formulate ideas and frame strategies to improve our school system so that we increase student achievement for all students while simultaneously closing the achievement gap and ensuring success for every child.

Entry Plan Objectives:

Leadership Objective

  • Expand on my current knowledge of the school district and its people as fully as possible in a brief period, outside the daily context of crisis and problem solving.
  • Ensure a flawless opening to the school year.
  • Ensure a smooth and orderly transition of leadership.

Organizational Objective

  • Review organizational structure, climate, budget, key work processes, practices, programs and resources to ensure alignment of these resources to efficiently and effectively meet 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.

Meetings and Interviews

I will conduct a series of meetings and key informational interviews to hear from critical members of the Eagle School District school community, policymakers and others. The primary goal of these meetings will be to actively listen and gather input from each stakeholder. My hope is that these interactions will be a foundation for authentic relationships and collaborations to benefit students. I need to hear firsthand from our stakeholders to understand the priorities and needs of our community and its schools. Before the close of each meeting, I also hope to have established some routine communication protocols with the different groups and individuals so that the conversation continues beyond our first discussion.  The most important part of entry is engaging in purposeful efforts to listen, learn, and begin to develop plans in collaboration with the Board and the Eagle Public School community.

Group Timeline
Individual Meetings
Principals (1 High School, 1 Middle School, 2 Elementary) July
Assistant Principals (3 High School, 2 Middle School) July
Central Office Cabinet

  • Assistant Superintendent/Curriculum
  • Business Manager
  • Director of Student Services
  • Director of Human Resources
  • Director of Technology
  • Director of Maintenance
Central office assistants Summer

  • Health/PE
  • Fine Arts
  • Student services
  • Nurse
School Committee Members July
Union President and Vice President July
  • Town Officials
  • Police chief
  • Fire chief
  • Town manager
  • Religious leaders
Focus Groups
Staff focus groups from each school August through September
Related service focus groups from each school
Paraprofessional focus groups from each school August through September
Family focus groups from each school led by PTO president September – October
Student focus groups September – October
School Committee After individual meetings
Community Groups

  • MADD
  • Recreation department
  • Parents against bullying and cyber bullying

  • Rotary
  • Senior Center
  • Library Director
August and September as available

Interview and Focus Group Questions

  • What are your general impressions of the schools in Eagle School District? What are its strengths and areas to 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 the Superintendent? How would you like to see it changed? How should it remain the same?
  • How effective are communications between the district and the community?
  • Describe the way parents are involved with the schools and/or the school system?
  • As you see it, what are the students like in Eagle Public School District?
  • Which tasks are your responsibilities alone? Which tasks do you share with others in central administration and/or in buildings? How does the overlapping of responsibilities occur? Are there areas where role responsibility is unclear?
  • What are the key issues for your own work in the school system? Why is each important? Which issues need immediate attention? Can you rank these issues in priority order?
  • What are your general impressions of the level of teaching in the district and the school you represent?
  • How is the level of communication throughout the district and in the school you represent? Please give examples. 
  • How is the level of collaboration throughout the district and in the school you represent? Please give examples.
  • What is the school system’s key issue – it might be different from your own – in the next few months? What should I know about this issue? When should it be resolved?
  • If you could make changes to the organizational structure of the district, what would it be?
  • What are some things that work very well with the organizational structure and practices of the district?  
  • What are you most proud of in the Eagle Public Schools?

School and Classroom Visits

  • Based upon the belief that spending time in schools and classrooms provides the foundation for learning about the district as well as relationship building, I will visit every school in Eagle School District by the end of September. Additionally, I may occasionally accompany principals on learning walks.
  • A second round of visits will span October through January and allow me to spend one half day in every elementary school, middle and high school and special programs. I will ask the principal and staff to craft an agenda that will allow me to experience each school as a learner, visit every classroom and interact with staff and students. By the end of my first 100 school days, my goal is to have visited classrooms in every school in the district. 

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

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

I will accept as many invitations as possible to speak at school and community gatherings. These might be church events, community workshops, Rotary luncheons or neighborhood association meetings.

At times, I will drop by meetings at schools, including faculty meetings, School-Based Decision Making council meetings, Parent-Teacher Association meetings, grade level meetings, professional development activities and teacher planning sessions. During these visits, I will just be there to observe and learn about issues, activities and efforts throughout the district. My intent will not be to evaluate or interject, but simply to listen.

Document Review

Objective: The document review is aimed to identify the strengths and opportunities for improvement within the planning and management process as it aligns activities with the strategic reviewing.  Analyzing data from the document review will be essential for Phase III, Next Steps.

The following documents will be part of the materials 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
  • MCAS 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 Improvement Plan

District and School Leader Retreat

The school and district leadership team and superintendent must operate as a team focused on ensuring equity and excellence for all students of Eagle School District. The school and district leadership team and superintendent will meet to collaboratively build relationships, set priorities, engage in team building, establish meeting norms, review operating procedures, discuss governance, and examine communication protocol. It is anticipated that this meeting will occur early in my tenure and before the opening of schools. Holding a retreat is priority number one for a successful leadership entry. The details of the entry plan will be shared and detailed discussions will occur about other transition activities.

Quarterly Reports

I believe a key part of the continuous improvement cycle is regular monitoring of results. To ensure transparency and accountability, district department leaders and school principals will provide quarterly reports and presentations to the central office leadership team. These quarterly meetings will focus on progress monitoring and will allow us to identify trends, challenges, and areas of refinement. By presenting information on a quarterly basis it will allow for interim corrections before results are final. The process will be formative in nature as the feedback will be used to make informed decisions and ensure that actions are aligned with the District Strategic Plan. The reports will occur in November, April, and August.

Closing the Communication Loop

Periodically throughout the entry phases the School Board will be provided with updates on the process and a summary of information being discovered. The community will also be provided with briefs concerning the entry plan and the learning that will be occurring. Because building shared awareness is critical to the school improvement process and transparency in decision-making is an important component of my leadership strategy, a community update will be provided after Phase II.  Department presentations will be made available through the web for all stakeholders. Also, we will be investigating the creation of a weblog, podcast, and/or other mechanisms to disseminate information about the findings during entry and receive feedback concerning our improvement efforts.

Development of Next Steps: Phase III: February  – May

This Entry Plan will afford me 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 Eagle School System. Through this process, I will begin to formulate ideas and frame strategies to improve our school system so that we increase student achievement for all students while simultaneously closing the achievement gap and ensuring success for every child.

Through my interactions with so many stakeholders, I hope to educate our school district and community about the focus and direction of the Eagle Public Schools. I am energized to build upon existing excitement and momentum to identify and execute the priority activities for our school district.

The Eagle School committee can expect a presentation of finding from this entry plan and a framework to create a strategic plan to implement findings.  The entry plan report findings will be shared with the Eagle School Committee.   The strategic plan will guide initiatives, programs, activities, and benchmarks on moving forward over the next 18 months.


Strategy in Action: How School Systems Can Support Powerful Learning and Teaching, By Rachel E. Curtis and Elizabeth A. City

The Entry Plan Handbook, Leadership and Learning Inc.

Format inspired by the work of Superintendent Dr. Peter Sanchioni

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This entry was posted on January 23, 2018 by in Uncategorized.

Dr. Matthew X. Joseph

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