Years ago, I wrote a post titled “5 Questions to Ask Your Students To Start the School Year” (which I revisited this past July), and it is by far one of my most popular posts and aligns with my focus on the importance of starting with strengths, no matter the role in the school community.
The questions I shared below can be used, modified, added to, or subtracted from, and can be leveraged in any classroom.

In the post, I share the following reflection:
“…teaching at different levels will provide you with different opportunities with students, but no matter what you teach, it is essential to listen to your students at the beginning of the year and solicit feedback to move forward, not just after they have left your care.
An important way we can serve our students is by getting to know what works for them and moving backward from there. This research into the children in front of you is crucial to help create a year that they will not forget, but that can make a tremendous impact on them moving forward.”
I am not sure who suggested it, as it has been done more than once, but someone asked me if they could use these questions with staff, and my first thought was “Of course!”
And if you look at the last part of the quoted paragraph, replacing students with staff and children with adults yields the same thought process.
See modified paragraph below:
An important way we can serve our
studentsstaff is by getting to know what works for them and moving backward from there. This research into thechildrenadults in front of you is crucial to help create a year that they will not forget, but that can make a tremendous impact on them moving forward.”
If you want to create exceptional learning experiences for your students, you do that first for the adults. We will often recreate what we have experienced ourselves.
I loved the idea, and while I was preparing to lead a workshop with Charleston County School District (SC) school leadership teams, I wanted to not only recreate the image and modify the questions for adults, but also to share the process I used.
Heading over to ChatGPT, I uploaded the original student image and asked the following:
“Can you take these 5 questions and make a version for principals that would help to build on staff strengths?”
Through the process, I was given the following five questions, which I then added to a Canva image for others to use.

Without prompting, it not only provided me with the following reasoning behind the questions:
What are the qualities you value most in a leader?
Helps you understand how your team defines effective leadership and what support they most need from you.What aspects of education or teaching bring you the most joy?
Encourages teachers to reconnect with their purpose and identify passion areas that can drive innovation.What is one big goal or question you want to explore this year?
Promotes curiosity and growth-minded reflection that can guide professional learning priorities.What are your unique strengths, and how can our team leverage them?
Focuses on capacity building and collective efficacy by aligning individual talents with school goals.What would success at the end of this year look like for you?
Centers on personal and professional growth while giving leaders a lens to align support and celebrate progress.
Super helpful.
But I also wanted to go a step further and ensure that these questions can be tailored to any school community, so I asked the following question:
How could these questions help the mission and vision of a school community?
Doing stuff for the sake of doing stuff is a terrible practice.
Aligning ideas to your current goals can be highly beneficial.
Again, here are the responses from ChatGPT:
1. Clarifying Leadership Alignment
Question: What are the qualities you value most in a leader?When staff articulate the leadership traits they value, principals gain insight into how to lead in a way that reflects the school’s core beliefs. It helps align leadership behaviors with the values embedded in the mission and vision, creating consistency between words and actions.
2. Reconnecting to Purpose
Question:What aspects of education or teaching bring you the most joy?
By encouraging educators to reflect on what brings them energy and fulfillment, this question links personal purpose to the school’s collective mission. When individuals see how their passion connects to a larger vision, motivation and commitment grow across the community.
3. Promoting Curiosity and Continuous Growth
Question:What is one big goal or question you want to explore this year?
This question fuels innovation and inquiry, both vital for realizing a vision of continuous improvement. It frames professional learning not as compliance, but as curiosity-driven growth that contributes to the evolution of the entire school.
4. Building Collective Efficacy
Question:What are your unique strengths, and how can our team leverage them?
A school’s mission is best achieved when everyone understands how their individual gifts serve the whole. This question reinforces collaboration, highlights diversity of strengths, and builds a sense of shared ownership for results.
5. Defining Success Through Shared Outcomes
Question:What would success at the end of this year look like for you?
This invites reflection that aligns personal and professional goals with the broader vision of the school. When staff define success and leaders listen, it helps ensure that day-to-day work, professional learning, and school priorities stay connected to meaningful outcomes for students.
As much as I appreciated these insights, the summary provided made a ton of sense and clarity on how you could personalize these questions (and more importantly, your staff’s answers), to create a purposeful path forward (together) through this process:
In Summary
Together, these questions foster a culture of trust, reflection, and shared purpose. They help every educator see themselves as an active contributor to the mission and vision of the school, ensuring that those guiding statements are not just words on a wall, but lived values shaping decisions, relationships, and growth throughout the year.
There are two reasons I share all of this with you.
- I hope it is helpful and that you can leverage the questions and modify them as needed. This one is obvious 🙂
- Most importantly, I wanted to walk you through my process and share how you can leverage these technologies not to replace thinking, but make you more thoughtful in whatever your endeavor. You may or may not agree with the summaries provided, but having the chance to converse back and forth with this technology might help you create or recreate something better for your community through the process. It definitely pushes my own learning and perhaps can provide a perspective you had not considered initially (Read, “Can AI Teach Empathy?” for more on this perspective).
Sharing the process of learning is often more important than the product. That is likely to help someone figure out a similar path (with modifications) in their own context.