Month: September 2021

Superintendent of Schools Interview Questions

  1. What do you anticipate being the most difficult problems that you will face in our district?
  2. Describe the process you use in communications between school board members and the superintendent.
  3. What process will you use to build an effective leadership team?
  4. What strategies would you use when responding to a crisis?
  5. How would you deal with a hostile and aggressive crowd attending a public meeting of the Board of Education? What plan might you put together in anticipation of such a meeting?
  6. What steps do you go through in developing a District Budget?
  7. What lessons have you learned in dealing with the Covid-19 epidemic and what changes would you seek to make which would improve the district?
  8. Assume that there is a serious need to improve buildings and grounds, how would you go about Capital Improvement Planning that might include a Bond Issue?
  9. What is your approach to effectively evaluate teachers and principals resulting in their professional growth and development?
  10. Outline your Entry Plan for your 1st hundred days
  11. What qualities do you look for in teaching and administrative candidates?
  12. How do you go about making visits to schools?
  13. leaders and Central Office
  14. How do you teach and mentor school leaders?
  15. What functions or problems should the Superintendent directly and personally take on?
  16. What process do you use in developing annual district goals?
  17. What role do you play in negotiations with various unions?
  18. How do you determine when it is necessary to communicate with school legal counsel?
  19. How do you handle Superintendent Student Disciplinary Hearings?
  20. How do you prefer to develop agendas for Board Meetings?
  21. What should be the role of the Board President?
  22. What is your role in dealing with grievances?
  23. How do you deal with conducting investigations of wrong doing?
  24. How do you prefer that the Board do your Superintendent Evaluation?
  25. Walk through the steps of developing and putting up a Bond Issue
  26. How do you go about deciding on a Snow Day?
  27. What is your approach to dealing with the Union Leaders?
  28. How transparent is your approach to “transparency”?
  29. How do you go about building morale?
  30. Taking a long-term view, how do you go about sustaining positive change?
  31. Describe your Decision-Making Process
  32. Tell us about an unpopular decision you made? What did you learn from it?
  33. Tell us about any innovations you brought about in the area of School Security and Public Safety
  34. How do you develop positive relations with Police and Fire Officials?
  35. What creative ideas do you have about maintaining positive public image for the district?
  36. How will you make yourself more accessible to your publics?
  37. How will you deal with “special requests and favors” from “entitled” constituents?
  38. How do you deal with disloyal school leaders who speak ill of your leadership?
  39. What would you do if you strongly disagreed with a decision of the Board?
  40. How long do you expect to remain in the district?
  41. What are professional or personal guiding principles that are non-negotiable?
  42. How do you deal with free speech and student publications?
  43. What is your vision of the future role of technology?
  44. How do you deal with the ever-rising costs of special education?
  45. What do you consider to be your three great professional accomplishments?
  46. Do you have ideas about cost savings?
  47. What would your critics say about you?
  48. What would your advocates say about you?
  49. What would you want to accomplish five years from now that would lead us to agree that you have been a successful leader?
  50. Tell us about a student, or teacher, or school leader who you feel you helped change the course of his/her life.


Here is a typical message I often get from newer school leaders:

I wanted to touch base with you. I have a few questions and value your insight.  I had a successful year.  Being a leader is certainly a challenge, but I have learned a lot. Do you have any advice for year two or three?

(1) How, in your experiences, do years two, three and four differ from year one?  

(2) I’ve been receiving a lot of different advice about future steps in my career.  In my district, I’m interested in ultimately moving into a principal position. I’d also be interested in K-12 coordinator position in other districts. Should I just wait and see how things play out here? There will likely be openings sooner rather than later, and then express my interest in being a building principal in the event an opening occurs, or should I look outside the district if the right opening comes along?

(3) I’ve been advised that you should always wait until gaining tenure before looking for a new position. Do you agree? I don’t want to be perceived as being ungrateful for being given the opportunity to work here.

I am happy in my position for now, but given the administrative and political structures here, I don’t know how long I might want to stay in my current role. Thanks for your insight!”

My response:

It’s great to hear from you. I’m not surprised you had a successful year. Year one is a “getting to know you year”—first impressions—can we trust one another—are you the real deal. Year two is “let’s get down to business and start doing some substantive stuff. The challenge, as you know, is that a lot of folks would rather “make nice” than “make improvements”. It’s tricky because you can’t alienate your constituents, even a minority of them, who could resist and/or undermine you and your efforts. My experience taught me that most teachers prefer to be comfortable with the status quo. They certainly don’t like changes being made without their input and involvement.

The degree to which you can push teachers and in what direction depends on the support of your principal and district leaders. Even if your leaders assert that they are aggressive and want change, you still need to be cautious.

I understand the “rule” to get your tenure first and then seek a new position. However, if you are confidential in how you search for a new job, you will probably be okay. That means, confide in no one—not even your closest allies—everybody gossips. Most districts to which you apply will maintain confidentiality until the very end of the process when they need to check your references.

The most accessible career path forward is usually within your own district; especially a larger district where there is a greater likelihood for movement. Personally speaking, in most schools an assistant principal is an important but a thankless job—student discipline, scheduling, cafeteria and bus supervision. The most redeeming aspect is that it’s the most viable path to the principalship. In my opinion, a k-12 subject area coordinator job does little for your career unless it’s in an innovative place that does great work with a well-earned reputation.

One last thought about asserting your leadership. Do not lead by advocating for a specific “pet program”, even if you think it’s a good thing. Lead by having your constituents look at a problem, especially if there is data that clearly demonstrates a problem. Then the group has the shared responsibility to define the real problem and search for possible solutions. Leading by advocating for a specific program, technology, or method is like starting with a pre-determined solution and then matching it to a perceived problem; it’s a solution in search of a problem. That approach is usually doomed for failure. You will be perceived as trying to enhance your career by making changes for the sake of change.

Let me offer an analogy to further clarify what I mean by not leading by pushing for your favorite approach. Let’s say you are concerned that your family members have unhealthy diets. Assume that you do most of the cooking in your family; that includes doing the shopping and preparing the menu. Assume you love vegetarian Indian food, particularly the taste of curry. You believe vegetarian Indian food is healthy and delicious, however, your family members prefer other kinds of meals. Nevertheless, you persist in trying to convince them to eat your Indian food. As they say in the movies, “Houston, you’ve got a problem.”

Hope this helps. Please call me if you need to discuss this further. Keep in touch.”


Seeking a leadership position is similar to a competitive horse-race. The odds for your success are largely based on: (1) the status of the potential employer, (2) the degree of nepotism at play, and (3) your qualifications and experience. The status of school communities can be stereotyped according to their historic reputation, that is the perceived quality of education, affluence, political stability, students’ college acceptance, achievement scores, etc. Whether these reputations are in fact valid can be suspect. Nevertheless, these reputations are widely accepted and durable, and determine how appealing it is to work in a given school district.

Frankly, school districts are often stereotyped as A, B, C, or D? A districts are affluent, homogeneous, high achieving. D districts are the opposite: poor, Black and Latino, low achieving, politically troubled. B districts are middle class; C districts are working class and usually diverse.

As an example, for an assistant principal position you might find about 250 or more resumes submitted for an A district, 125 to 150 for a B, 40 to 50 for a C, and 20 to 30 for a D. This means that the ratios of resumes received per “category” are about for every 1 for D, there are 2 for C, 5 for B, and to 10 for A. Yes, an A district would get 10 times the number of applicants compared to a D. These ratios are consistent beyond just assistant principal positions; these ratios hold up across the hierarchy of leadership jobs. Therefore, your odds for getting an interview are much better for D and C districts.

How does nepotism play into the equation? Let’s define “nepotism” as “giving preferential treatment”. In many districts “courtesy interviews” are extended to current and sometimes past employees, and friends and family of those in influential places. Assuming that 10% of first round interviewees are for purposes of courtesy, that means that your odds of even getting interviewed goes down by 10% because the number of interviews granted will be limited.

Finally, let’s focus on qualifications and experience. The most important qualifications beyond the minimum requirements of proper certification and minimum years of service, are the status of the district in which you are currently serving, the similarities (demographics) between your current district and theirs, the doctorate, your perceived race and ethnicity, the reputation of the colleges from which you graduated, and particularly your accomplishments.

All of these factors go into the odds of just getting an interview. What can you do to increase your odds? The only factor that you have any control over is your accomplishments as reflected in your resume. So what should you do– review and revise your resume and emphasize your accomplishments as they relate to the job and the school-community.

My frank analysis is based upon my decades of experience as a school leader who participated in the screening and interviewing of candidates, and my ten-year experience in coaching hundreds of candidates for leadership jobs. It is not my intention to discourage you from applying for jobs. I do, however think it’s important for you to understand the realities and the odds you are facing. I also want to be clear that there are many excellent, well-qualified “insiders” who get interviews, and that “long-shots” can and do break the odds and win the horse-race.

What Does Career Coaching Involve

Have you considered being coached to improve your resume and your performance during an interview and wondered what it entailed? As a successful coach of 100’s and 100’s of educators over the last ten years, let me give you an overview of my approach: (1) a preliminary review of your resume and cover letter; (2) an in-take conversation; (3) usually 2 to 4 one-on-one coaching sessions depending on need. The following is a brief summary of what takes place:

1. Preliminary Review of Your Resume (no charge)—evaluate the resume based on:           

   a. Is the resume to the point, simple and logical?

   b. Emphasis on accomplishments; not a Job Description

   c. Emphasizes your strengths

   d. Does your timeline make sense?

   e. Describes your skills and knowledge that match the scope of the job; omits irrelevances

2. 10-minute In-Take Conversation (no charge)

   a. What position(s) are you seeking?

   b. How long have you been applying for jobs? How many jobs have you applied for?

   c. How many first-round interviews have you had? Second-round? Beyond second-round?

   d. What do you think the problem might be in not moving on in the process?

   e. Information regarding fee; scheduling; brief feedback on resume; answer additional questions

3. Coaching Sessions

  • Review and edit resume and cover letter; how to prepare for an interview; and begin analyzing and crafting response to “Tell Us About Yourself”
  • Finalize and practice response to “Tell Us About Yourself”; strategize answers to 10 to 20 of the most frequently asked questions.
  • Analyze what your future supervisor is really looking for.
  • Mutually create your narrative that emphasizes your strengths and neutralizes any potential weakness.
  • Do mock interviews and get constructive feedback.
  • Learn strategies and tactics on “how to close the deal” and negotiate salary.


Over the years I have had the privilege of visiting a few of the most successful high schools in New York State. These visits were part of a study conducted by PLC, Associates. All of these schools are high need; meaning they have poverty rates of at least 90%. Their student populations are in excess of 95% Black and Latino. Yet they break the mold! Their 4-year graduation rates are over 90%. There are very few serious disciplinary incidents. And the vast majority of students indicate that they’re most pleased with their relationships with their teachers and school leaders. Here are just a few anecdotes drawn from what I witnessed in several high schools.

  1. CREATING A CARING SAFE ENVIRONMENT–The first period starts at 8 AM. Upon entering the building at 7 AM, I encountered about 100 students already assembled in the large lobby and the adjacent cafeteria. By 7:30 the group has grown to about 500, 300 of whom occupying every seat in the cafeteria, most of whom are consuming breakfast. The principal, assistant principals and a handful of security guards are casually looking on. Scores of students come by and exchange hello’s and fist bumps with the staff. The staff seem to know everyone’s name. An assistant principal comments, “Our job is to be where the kids are to let them know we’re here for them.” The tone is relaxed and friendly. As teachers arrive, they scoop up small groups of students who accompany their teachers to their rooms for extra help or just to chat. At 7:30 the throng slowly disperses. Looking into the now empty cafeteria, there is almost no evidence that 300 teenagers had been there—no refuse on the floors, nothing left on the tabletops, and all the chairs neatly placed under the tables. A caring school culture cuts both ways—students recognize that the staff cares and in return students demonstrate that they care.
  2. PUTTING STUDENTS AT THE CENTER–An Anti-Gun assembly program was presented to celebrate the anniversary of the Parkland shooting. The entire program, attended by more than 300 students, featured student speakers who had suffered family losses to gun violence and a featured speaker. The 40-minute program was initiated, planned, led, and supervised by students. There were five staff members in attendance who passively observed the proceedings from the rear of the auditorium. The students in attendance were orderly, attentive and respectful. This was a remarkable event. At one point a student, who was obviously overcome emotionally, rushed out of the auditorium. As a staff member approached him, he flashed a small card, and the teacher backed away and following him at a reasonable distance. At the conclusion of the event, a female guidance counselor was standing outside the now locked bathroom, adjacent to the auditorium. After the crowd had dissipated, the now composed young man, accompanied by a custodian exited the bathroom, and went back to class. Why did the custodian get involved?  Because he lives in and is active in the community and the student know him and trust him. What was the significance of the small card he had flashed? The Principal explained that a “purple card” is issued to students who are known to be dealing with severe trauma in their lives. The students flash their card only when they are in emotional distress. The card signals that the student be allowed to leave his or her classroom without any questions be asked, and seek help while a security person monitors them, ascertaining that he or she needs help from a support person. There are about 25 such cards in circulation, and reportedly no one has ever abused the system. This is only one incident that illustrates how exceptional this school-community truly is. The students are responsible, are given space to be independent and express their social conscious and caring of one another. The staff listens to students’ wants and needs, and responds by trusting their students to do the right thing—and they do.
  3. FOSTERING AUTHENTIC RELATIONSHIPS—The High School Principal is not only visible but is a constant presence. He is an affable man with tremendous energy. As a result of his seven years of experience within the district, he has forged significant relationships with his students. As I walked the halls with him and witnessed his interactions with students, it is striking how he knows the names of the vast majority of his students, and that there is an authentic fondness between him and each student. He is a genuine cheerleader and advocate. He believes that a key role of the school is serving as the in loco parentis. He says, “The school has to replace things that are not taking place in their lives. This is their home away from home. So many get here by 7 AM and they’re still here until 6 PM.” A teacher reported to me, “Often times there are more staff members attending evening performances and sports events than parents. Many of their parents must work two jobs just to survive; they just can’t be home or be in attendance. We try to support our kids in every way we can. We have to make up for that.” He proudly goes on to say, “Not only do the adults in the school embrace the kids, but the kids embrace each other. They are accepting of one another. We have very little violence. I believe their parents understand what we have here, and in return the families choose to stay in the district. That’s how you build a school-community culture”.
  4. LISTENING TO PARENTS’ VOICES—During an hour-long conversation I had with about a dozen parents, there was a variety of viewpoints expressed during our frank, unfiltered discussion regarding how race and culture need to be dealt with in schools. Here are some of their comments:
    1. “I think it’s more important for students to have teachers of color at younger ages.”“Our children need to be exposed to diversity across the board.”
    2. “All teachers need empathy. If they don’t have it, then the school leaders have to train it.”
    3. “As a parent, I try to open my children up to other cultures and communities.”
    4. “Knowledge of self, who I am, is the key. We should try to provide equity. This means we should not only teach Eurocentric American History— ‘His Story’—but we must also teach and share our story, too.”
    5. “Schools do not fully recognize the need for all children to learn about the Black experience in this country. It should be integrated into the curriculum. There should be questions about it on the Regents. It starts at the top with the policy makers.”
    6. “Black history should not only be taught in Black schools, but all schools”
    7. “As long as there is respect for our children, and we have access to what is happening in the schools, and there is accountability, then the teachers’ color is of no concern.”
    8. “We need to add a course about the African diaspora from Africa through the Caribbean and into America.”
    9. “Students learn about the ‘dust bowl’ experience of the 1930’s by reading ‘Of Mice and Men’. Why don’t they read literature that tells about the Black experience of that era as well?  We need to get out of the box, and it starts with vision at the top. As for the future of this district, we need the continuity of good leadership.”
  5.   SETTING HIGH EXPECTATIONS–The principal presents a fatherly figure. He can be both stern and caring at the same time. His long and successful experience have earned him a deep respect by his faculty. He exudes a practical wisdom. Students and teachers cite his often-said motto: “School is a dignified place”. When students are asked what that means to them, they say: “It means that school is a workplace—it’s a serious place to learn”. “You don’t have to worry about anything that’s taking place outside of school”. “It’s all about learning”. “You just gave to keep your mind on your goals and what you want to accomplish.” When teachers were asked the same question, they said, “It speaks to our culture. That there is a structure here where students come ready to learn”. “It’s a mindset that the school is a safe haven. What goes on in here is different from what happens to them outside of school.”

6. THE PAST IS NOT AN EXCUSE—Over the last decade, this school has gone through a seismic shift from a suburban to an urban-suburban school. The principal recognized the necessity to shift the culture of the school.  It meant that the teachers would have to make fundamental changes regarding their teaching styles and how they related to this evolving student demographic. “Previously, teachers tended to react punitively to students’ non-compliance, without explanations; to be confrontational”, the principal explained. The principal grasped the need for the faculty to be more tolerant by demonstrating respect for students. “Teachers needed to learn to say, ‘please, and thank you.  They needed to stop directing sarcasm to students. It starts with their language, and it had to change.” In addition, the principal instilled a culture of high expectations for scholarship and behavior, accompanied by the necessary support to fulfill those expectations. In order to support teachers in their mission to have students attain high expectations, the principal created policies to remove all impediments to teaching and learning. Specifically, teachers are not expected to stand corridor duty between periods. Administration and security take care of those duties, including enforcing that students exhibit their identification badges. “There needs to be fewer opportunities for confrontations”, according to the principal. What might be perceived as a contradiction, nevertheless, the principal insists that school rules (no hats; no ear plugs; zero tolerance for violence, drugs, bullying, and insubordination) be rigorously enforced. He feels that this is his way of demonstrating support for teachers, and that is maintaining control of the building, and focusing teachers’ energy on teaching and learning.

These are just a few experiences I witnessed. I believe they get to the core of what needs to be done in all schools. This requires strong visionary leadership, persistence and patience. Are these common experiences in your school? How does your school compare to what I have described? And yes, the mold, the stereotype, it can be broken. Why can I say that, because it has been broken.

Systemic School Reform Is a Marathon

When one comes into a new leadership position, the deficiencies of the organization become pretty apparent after a few months. I have had occasion to participate on visiting committees for purposes of school accreditation, and identifying meritorious schools for grants and awards. Visitations usually last a few days during which time I would meet with a whole range of groups and individuals within the school. After two or three days, I would usually have a fairly clear picture of the strengths and weaknesses of the school.  It doesn’t take long. There’s no place to hide 800 pound gorillas. Coming into a new job as a school leader is very much the same thing. Within a few months, you could usually scope out about 90% of what’s right and wrong within the organization.

However, I have learned over the years that the hidden 10% is really the most difficult to figure out and even more difficult to fix. Painting a room is a fitting metaphor. Ninety percent of the job is the space on the walls. Ten percent is the area around the floor, ceiling, windows, and outlets. Painting that 10% usually takes as much time and requires even more effort than the 90% of wall space. We judge the quality of the paint job by looking at the hard to paint parts. The same goes for schools.

I had a friend who was an engineer. He told me that there was an engineering principle that said that it took the same amount of energy input to do the first 90% of a job than it took to do the next 10% of the job.  In other words, to get from 51 to 52 takes a 1% effort of input, but to get from 90 to 91 or 97 to 98, it took ten times the input to gain the additional one percent. 

What does all of this have to do with implementing systemic school reform as a school leader? If my theory works, to improve upon 90% of the deficiencies that you find takes a couple of years on the job. It is called “picking the low hanging fruit.” Working on the next 10% requires at least the next four years. Creating and institutionalizing systemic changes involve elevating the organization to new standards. System theory calls this process “growing the conditions of the organization”.  Systems thinkers tell us that for every “growing action” there is an opposite “slowing action”—those actions that resist changes. Most people who work within the organization are usually quite content with the predictability and equilibrium of the existing conditions of the organization. This doesn’t make them bad people or necessarily bad professionals. In fact, they are usually good people. Most of us like the security of working within an organizational structure that is comfortable and predictable. However, comfort and predictability do not lead to excellence. So, when leaders develop strategies which are intended to lead to growing actions, many people in the organization respond with strategies and tactics that frustrate those actions. The greater the intended reforms, one should expect the greater the resistance. In my experience, the greatest challenge for school leaders is how to overcome resistance and oppositional behavior which exist throughout the organization and in the school-community.

Let me give you just a few typical examples.  What happened when a leader attempted to change the textbook in a school, at a grade level, or teachers’ favorite text?  What happened when you tried to transition from methodologies where the teacher was the center of instruction to one where the student became the center? What happened when we put computers into classrooms? What is happening when we want to emphasize student thinking into the instructional program? In every case, there are slowing actions– some call it “push back”.

So how do we cope with slowing actions? Short answer, we attempt to neutralize each tactic with a counter tactic. When a new technology platform is put in place, you send around a trainer who spends time with every individual in the organization who uses the system demonstrating to use the new system. Not only do you provide training, but you give the people who are using the new system several months notice as to when the new system will take effect. You leave both systems up and available, and then you wean folks off of the old one and eventually remove it at the pre-designated date. Change requires providing additional energy inputs into the system. In effect, you might still be using the old system which operates at the existing cost, while you are simultaneously designing and implementing a new system at significantly extra costs.

What are the mega changes taking place now? I would place the effective use of remote learning, and dealing with issues of equity and racism at the top of the list. These are sweeping structural changes and cannot be confused with school improvements because of the scope and complexities of such structural change. Sweeping structural changes demand seismic efforts and require more than a four-year cycle.

Sustained, systemic structural change often requires about six to eight years. To finish a marathon demands effective, sustained and committed leadership. It’s a marathon, not a sprint.