June is a whirlwind for schools. Many high schoolers have already walked the stage, others are furiously preparing for final exams. Middle schoolers are walking the line between playful and mischievous and the administrators in charge of promotion ceremonies are queuing up Pomp and Circumstance. Elementary schools furiously finish up assessments and end-of-year projects and clear out the rooms to send remaining pencil boxes and a year of artwork home. 

. As a leader, thinking about bringing your own year to a close, the conversations you have in the month of June and how you have them in these waning days of the school year are a great opportunity for you to learn, develop and forge stronger relationships across the board. You can do it through conversation and you can do it without tipping the scales on an already burnt-out educator community. 

Who should you be talking to right now?

There are three main groups for you to seek out for an informal reflection  - teachers, non-teaching staff, and your supervisors. 

Teachers - depending on how close you are to the end of the school year, you may or may not have access to all teachers any longer if the year has ended and contractual workdays are done. However, if you are still in the work year, then set some time on your calendar, intentionally, to connect with a minimum of five teachers. You’ll need to think strategically about who to seek out and this is a perfect opportunity to (a) intentionally balanced teachers you regularly interface with and those you have much less contact with (b) randomly draw names or (c) make strategic choices aligned with school priorities. These conversations are meant to be informal and you want to think about what makes them most comfortable for the teacher.

Can you offer to help pack up the classroom while talking? What about getting a favorite coffee, boba, matcha, or chai and taking a walk around campus? Recognize power dynamics and make the situation comfortable and be transparent about why you want to set aside some time to talk. Something along the lines of “It’s the end of the year, and in addition to my traditional review of what happened, I really want to seek out some different perspectives and so I’d love to just listen to what you have to say. I want to make it whatever works best for you, so I could help pack up your classroom with you as we talk, or I”m happy to bring a coffee to sit and take a walk around campus as we talk or we can always meet in my office. I’m meeting with about 5 teachers and office staff as well as my supervisors”. When you give people the full picture, you are helping to build trust and dissipate any suspicion of ulterior motives. Let people opt out, but aim to have five listening conversations. That means you are doing 90% of the listening and 10% of the talking. Listen, absorb, and prevent yourself from defending. You've asked them to reflect and you can give them the space to do so without edits. 

Office and School Staff (non-teachers) - Your main office staff, paraprofessionals, custodial and cafeteria teams all have unique vantage points on your school. Building in time to listen to them and cultivate and deepen those relationships will only serve you and the community for the next school year. Follow the same steps as with teachers and aim for 5 different people. Be mindful of collective bargaining agreements and set up your conversations in line with that. State clearly the purpose of your conversation “You have a unique vantage point on the operations and culture of our school. I’d really appreciate the chance to ask you a few questions for you to reflect upon the year. Your answers will help me to plan for the year ahead and keep in mind things that I might not be seeing.” Listen, echo, and listen some more. 

Supervisors - We don’t often proactively seek out our supervisors to reflect with us and give us their insight into how a year progressed. Making time with your direct supervisor or others in the district office with whom you frequently interact will yield valuable information for you to use in planning for the next year. And making the time for individual, direct conversation also strengthens the professional bonds that you have in place providing you with an even stronger foundation in the year ahead when you need to seek advice and guidance. In instances where you do not have a strong or positive connection with your supervisor, setting up time to reflect on the year helps you to gain clarity about their expectations and perspective, document your own efforts to meet district goals, and potentially find common ground to move forward. You also need to take into consideration the nature of your relationship with your supervisor. Asking the same informal questions about growth and comfort zone that are listed below to a leader who models reflection and learning will be a natural conversation. However, if you have a more traditional and hierarchical supervisor, you might want to tailor the questions. Instead of “When did you move out of your comfort zone in the last year?” you might say “As you model learning and growth in our district, what would you consider an area where you grew in a new way or tried something outside of your typical comfort zone?”

Choose no more than four questions from the list below and use the time in informal conversation. When taking notes, ask permission of the person you are talking to and give them the chance to see the notes you’re writing. (this is particularly important in school cultures where there is currently low trust or mistrust between administration and staff). Be transparent with your own answers to the questions and genuinely thank them for the time they've spent in conversation with you.

Conversational Reflection Prompts

 (Choose up to four prompts to use consistently in your conversations)

What went better than expected?

What didn’t go according to plan?

What would have felt supportive to you last year?

When did you move out of your comfort zone in the last year and what happened as a result?

What would you consider any overlooked or underappreciated assets in our school or larger community?

What new skill did you acquire this year? 

What policies/procedures felt most effective to you? Which ones felt like they didn’t serve their purpose?

This is a listening conversation. Create the space to have it with ease and not rushed. Challenge yourself to focus and not multi-task in the moment of the conversation. People remember when we give them our full attention or just a small part as we glance down at our text messages. The questions you can bring to these conversations create the opportunity for someone to share deeply in ways that will only help you as a school leader. 

I recommend that you reflect on the questions yourself before you ask a single other person. Then revisit them when your conversations are done. When you approach the conversations with curiosity and openness, even the critical comments will land differently as data. You can look for outliers, and alignments, whose voices and perspectives are centered and which might not even be included. It's all input for your planning and data for you to reflect upon as you consider the varied experiences of the adults who contribute to the work side of your school community. 

When you seek people out to listen to them, you will have an abundance of information to celebrate, calibrate and create a more powerful 2023-2024 in your world.