20 Questions

Questions to Ask Superintendent

Essential questions to evaluate school superintendents, understand their vision, and assess their leadership approach.

1

What is your vision for this school district and how do you plan to achieve it?

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Why this works

Reveals their long-term goals and strategic thinking, showing whether they have a clear direction for the district.

2

How do you approach student achievement and what strategies do you use to improve outcomes?

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Why this works

Shows their commitment to academic excellence and reveals their approach to data-driven decision making.

3

What is your philosophy on school funding and how do you prioritize budget allocation?

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Why this works

Reveals their financial management approach and shows how they balance competing needs within limited resources.

4

How do you handle teacher recruitment and retention, and what support do you provide?

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Why this works

Shows their commitment to teacher quality and reveals their approach to supporting and developing educators.

5

What is your approach to school safety and how do you ensure student and staff security?

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Why this works

Reveals their commitment to safety and shows their strategies for creating secure learning environments.

6

How do you engage with parents and the community, and what role do they play in decision-making?

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Why this works

Shows their commitment to community involvement and reveals their approach to stakeholder engagement.

7

What is your approach to diversity, equity, and inclusion in the school district?

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Why this works

Reveals their commitment to creating inclusive environments and shows their strategies for addressing equity issues.

8

How do you handle conflicts between different stakeholders and what is your conflict resolution approach?

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Why this works

Shows their leadership skills and reveals their ability to navigate complex political and social dynamics.

9

What is your approach to technology integration and how do you prepare students for the digital future?

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Why this works

Reveals their vision for educational technology and shows their commitment to preparing students for modern challenges.

10

How do you measure success and what metrics do you use to evaluate district performance?

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Why this works

Shows their accountability approach and reveals what outcomes they prioritize for the district.

11

What is your approach to special education and how do you ensure all students receive appropriate support?

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Why this works

Reveals their commitment to inclusive education and shows their strategies for supporting students with diverse needs.

12

How do you handle school board relationships and what is your approach to governance?

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Why this works

Shows their political skills and reveals their ability to work effectively with elected officials.

13

What is your approach to curriculum development and how do you ensure academic rigor?

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Why this works

Reveals their educational philosophy and shows their commitment to maintaining high academic standards.

14

How do you handle crisis situations and what is your emergency management approach?

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Why this works

Shows their crisis leadership skills and reveals their preparedness for handling emergencies.

15

What is your approach to professional development and how do you support staff growth?

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Why this works

Reveals their commitment to continuous improvement and shows their investment in staff development.

16

How do you handle budget constraints and what is your approach to financial management?

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Why this works

Shows their financial acumen and reveals their ability to make difficult decisions about resource allocation.

17

What is your approach to student discipline and how do you create positive school climates?

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Why this works

Reveals their philosophy on student behavior and shows their strategies for creating supportive learning environments.

18

How do you handle communication with the media and what is your approach to public relations?

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Why this works

Shows their communication skills and reveals their ability to manage public perception and media relations.

19

What is your approach to innovation and how do you encourage creative thinking in education?

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Why this works

Reveals their openness to new ideas and shows their commitment to educational innovation and improvement.

20

How do you handle your own professional development and what are your goals for the district?

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Why this works

Shows their commitment to continuous learning and reveals their vision for the district's future direction.

Best Practices for Superintendent Evaluation

Expert tips and techniques for getting the most out of these questions.

Best Practices

Ask for Specific Examples

Request concrete examples of their achievements and how they've handled specific challenges in previous roles.

Consider Community Fit

Evaluate whether their values and approach align with the community's expectations and needs.

Assess Leadership Style

Consider how their leadership style will work with the existing school board, staff, and community dynamics.

Question Sequences

The Vision and Strategy Assessment

1
What is your vision for this district?
2
How do you approach student achievement?
3
What is your philosophy on school funding?
4
How do you measure success?

The Leadership and Management Evaluation

1
How do you handle teacher recruitment and retention?
2
What is your approach to school safety?
3
How do you engage with parents and community?
4
How do you handle conflicts between stakeholders?

Common Pitfalls

Don't Focus Only on Academic Achievement

While academic outcomes are important, also consider their approach to student wellbeing, safety, and community engagement.

Avoid Accepting Vague Answers

Push for specific examples and concrete details rather than accepting general statements about their approach.

Don't Ignore Community Fit

Consider whether their values and approach align with the community's expectations and the district's unique needs.

Evaluation Templates

The Comprehensive Superintendent Assessment

1
Step 1: Evaluate vision and strategic thinking
2
Step 2: Assess leadership and management skills
3
Step 3: Review community engagement approach
4
Step 4: Consider cultural fit and values alignment

The Stakeholder Input Process

1
Step 1: Gather input from teachers and staff
2
Step 2: Collect feedback from parents and community
3
Step 3: Review board member perspectives
4
Step 4: Assess student and parent satisfaction

Further Reading

"The Superintendent's Fieldbook" by James Harvey
"Leading for Learning" by Phillip C. Schlechty
"The School Superintendent" by Theodore J. Kowalski
"Educational Leadership" by Daniel L. Duke

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