5 Questions You Should Ask Your Leader

One of the most visited posts I have ever written on this blog was titled “5 Questions You Should Ask Your Leader.” I originally wrote the post in 2014, and with the recent release of “What Makes A Great Principal,” I wanted to see how much of what I wrote then still connect today and perhaps create some new interview questions for leadership positions based on the book in the future.

One of the things that I am proud of while reading this post is that I still agree with the questions that I posed in 2014, although how they could be answered and achieved can look different today than they did in the future. I often fear that we are looking for the “new” when things from the past that we can use today align with our hopes for school in the future. I actually wrote the following in “What Makes A Great Principal“:




If you have any questions you would like to share after reading the post that would be helpful for interview questions, please share them in the comments.

Onto the post!




5 Questions You Should Ask Your Leader


A superintendent recently asked me if I had some questions to ask his principals to start the year. The questions I gave him were based on the following areas:

  • Fostering Effective Relationships
  • Instructional Leadership
  • Embodying Visionary Leadership
  • Developing Leadership Capacity
  • Creating Sustainable Change

In my opinion, the principal is probably the most crucial job in an educational organization. Many studies reiterate this, but I think it is that they have the most authority closest to kids. It is not to say that teachers aren’t important; they are absolutely vital. But a great principal will help to develop great teachers, and a weak principal will do the opposite. They also tend to push great teachers out of schools, although most of the time unintentionally. Bad leaders tend to drive away great talent. A great teacher can become even better with a great principal. As the very wise Todd Whitaker says, “When the principal sneezes, the whole school gets a cold.”

Even though the questions were developed for superintendents to ask principals, I think that they should be questions any educator, parent, and even student should be able to openly ask their principal.



1. What are some ways that you connect with your school community? (Fostering Effective Relationships)

When asking a principal this question, it is vital to look for answers that go beyond the basic answers like staff meetings, emails, etc. I would look for answers that go above and beyond what is expected. For example, one of the best principals I knew spent every morning welcoming staff and students to the school at the main doorway. He would ask questions about their family, talk to them about their lives, and get to know them much deeper than expected. Although this principal has been retired for a few years, many of his staff refer to him as legendary because of the way that he would go above and beyond connecting with kids and the community before and after school.


2. What areas of teaching and learning can you lead in the school? (Instructional Leadership) 

Stephen Covey talks about two important areas for leaders: character and credibility. Many principals are great with people yet really do not understand the art and science of teaching or have lost touch with what it is like to be in the classroom. Although a leader does not need to be the master of all, they should still be able to walk into a classroom and teach kids. They should also be able to lead the staff in workshops that focus directly on teaching and learning. If teachers understand that a principal understands teaching and learning, any new initiatives are more likely to be seen as credible in their eyes.


3. What are you hoping teaching and learning look like in your school, and how do you communicate that vision? (Embodying Visionary Leadership) 

Many school leaders often communicate a BIG PICTURE of what schools should look like but can’t share what it looks like for teachers and students. It is essential to discuss elements of learning that you are looking for in the classroom. It is essential to hold this vision and help develop it with staff and be able to communicate it clearly. Many new educators walk into schools thinking that “quiet and order” are the expectations for classrooms, so even though they are doing some powerful work in their classrooms that looks quite messy, they are worried that it does not fit in with the vision of their boss. Due to this, many will often try to tailor their work to look like what they think the principal wants because they don’t know what is expected. Having a vision is important but clearly communicating and developing that with staff is also essential.


4. How do you build leadership in your school? (Developing Leadership Capacity)

Many principals are great at developing followers, but fewer are excellent at developing more leaders. There has been this notion for years that you do everything to keep your best talent at all costs, but in reality, it is vital to figure out ways to develop people, even if that means they will eventually leave. Great schools have become “leadership” hubs that often lose great people to other organizations or different positions within the greater community. Still, they often get a reputation of being places where leadership in all areas is developed, attracting some great people. Wouldn’t you want to work with someone who will try to get the best out of you?

Here is a quote I have shared before on this topic:




Again, great leaders develop more leaders. What is your plan to make this happen?


5. What will be your “fingerprints” on this building after you leave? (Creating Sustainable Change) 

This has been a question that was asked of me years ago by my former superintendent and has been one that has always resonated. She shared with me that she should be able to walk into my school and see the impact I have had as the leader of the building. This is not to say we throw out what the former leader has done—quite the opposite. Great leaders will not come into maintaining the status quo but will bring their unique abilities to a school that will help them reach the next level. They will build upon what has been left, but they will work with a community to ensure that their impact on a school lasts long after their time serving the community. This is where all of the other questions above truly come together, but it takes time and dedication to make it happen.



The old notion that teachers and students are accountable to a principal, and not also the other way around, is one that is dying (thankfully).


Great leaders know the higher you go up in any organization, the more people you serve, not the other way around.


I encourage you to talk to your principal, no matter your role, and ask them their thoughts on some of the questions provided.

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