Note to readers: I often write about leading with a coaching mindset. This post focuses on one part of the observation process, the pre-observation. Each part of the process matters, but here I’m honing in on how the pre-observation conversation can set the stage for growth, reflection, and connection as I mentor a new administrator on our team.
In my book The Leader Inside, I share that teaching is a calling. It’s a beautiful gift that allows us to unleash the potential in others, potential they may not even see in themselves. Along the way, mentors were placed in my path who served as lanterns, guiding me to each new destination. I’ve come to learn that every interaction both favorable and unfavorable, served as a mentor, showing me who I wanted to be, how I wanted to teach, lead, and build relationships. And isn’t that the heart of everything we do in education? To me, every observation whether as a teacher, coach, or administrator has become a way of paying it forward through the observation process, carrying forward the mentorship I once received.
Learning from Mentors
When I stepped into a formal leadership role as a building administrator, I carried with me the lessons and advice of great educators and leaders I had observed. Yes, observed. I take everything in: words, actions, and follow-through. Those moments shaped my leadership identity.
But stepping into administration also opened doors to areas where I had so much to learn: safety, operations, management, student life. Even with a solid background in curriculum and instruction, it can be a challenge to feel like an expert. I believe we’re not meant to feel like experts. With every new thing we learn, we see just how much more there is to discover.
I was fortunate to have a strong mentor in my building principal. I shadowed him closely, asked questions endlessly, and observed how he handled circumstances big and small. We built trust quickly. I could admit when I could have done better, and instead of discouraging me, he lifted me up. Encouraging. Supportive. Uplifting.
I’ll never forget watching him conduct a pre-observation meeting, the way he connected with teachers, the reflective questions he asked, and how he helped teachers think differently about their practice. I remember thinking: How powerful would it be to combine what I was learning from him with my own background in coaching? What if the observation process could be less evaluative and more about coaching?
That reflection eventually grew into one of my most well-read blog posts, Observing Through a Coaching Lens: 8 Ideas That Still Continue to Transform Practice. In it, I outlined how leaders can use observation as a coaching opportunity rather than a compliance exercise, which has since become a cornerstone of how I approach this work.
Asking the Right Question
In my book, I share a question I continually ask myself: Lauren, what type of leader do you wish to be?
My answer? The type of leader I always needed. I was always seeking leaders who would give feedback that built my capacity and stretched my practice. Truthfully, only a handful of my formal observations as a teacher ever lifted my practice to a new level. But those that did made a lasting impact. That is the kind of experience I want to give to others.
We may not always get it right. We may find ourselves rushing through some conversations, focusing too much on logistics instead of listening deeply. But with each opportunity and each time we draw from a coaching mindset, we gain the clarity and confidence to slow down, connect, and ask better questions. That’s when the process transforms into something far more powerful.
Paying It Forward
Now, in my fifth year as an administrator, I still don’t consider myself “experienced,” but I have learned a lot. Recently, two new administrators joined our team, and I saw an opportunity to pay it forward, so I invited them to shadow me during the observation process.
To me, the pre-observation is one of the most important conversations we have as leaders. It’s not a formality or a box to check. It’s an opportunity to connect with the teacher, listen to their intentions for their class, and engage in thoughtful dialogue. Through questions, we can help teachers think about how they might level up their practice and, most importantly, meet the needs of all learners.
As Jim Knight reminds us in his ASCD article: The Four Pillars of Peer Instructional Coaching, “Good questions are real questions, not leading questions or advice with a question mark tacked on. They deepen conversations, invite reflection, and communicate that we value our colleagues’ knowledge and ideas.”
When leaders approach pre-observations this way, teachers don’t just feel evaluated, they feel supported, trusted, and stretched to grow. That’s where trust and capacity begin to take root.
The Process: Five Steps to Model
When mentoring new administrators, I break the pre-observation process into five steps. Each step creates space for both teachers and administrators to reflect, connect, and grow.
- Invite
Ask the teacher if they are comfortable and invite the new administrator to join. This signals respect for the teacher’s time and trust in their professionalism. - Set the Stage
Begin by introducing the teacher and the new administrator. This step provides insight into the teacher’s background and context while giving the new administrator a window into the culture of the school and district. - Explain the Process
Outline how the meeting will go and let both the teacher and the new administrator know that you may pause to “coach in” along the way. This models transparency and helps everyone understand the learning purpose behind the process. - Engage in Dialogue Through Questions
Use reflective questions to spark meaningful conversation about teaching and learning:
- What are you currently doing in your class, and where are you going next?
- Which priority standards are you addressing, and can you also include a content-area standard?
- What is the learning activity, and what pathways will you provide for students to show their learning?
- How are you planning to meet the diverse needs of all learners as they work toward the target?
- How will students know the expectations? How will they know they’ve mastered the learning target?
- What assessments will you use to determine whether students have met the learning target?
- What are you currently doing in your class, and where are you going next?
This type of questioning also provides a window into how teachers are forming connections with students and building relationships. For instance, when a teacher explains why they chose a particular discussion protocol, text pairing, or grouping strategy, they often reveal how they are thinking about student engagement, trust, and inclusivity. In a high school English classroom, for example, literature naturally lends itself to interdisciplinary work, students may build historical context while deepening their understanding of a text. But beyond the academic lens, the teacher’s responses often highlight how they intend to invite student voice, encourage collaboration, or create opportunities for belonging.
Engaging in this kind of dialogue helps new administrators see how a pre-observation conversation shifts from “planning for an observation” to truly “planning for student learning and connection.” This is where questioning and listening become the core of leadership. As Knight reminds us, “When we really listen to others, we demonstrate respect and build connection. Effective listeners focus on what their learning partner is saying so they can think with them.”
- Debrief with the Administrator
After the teacher meeting, circle back with the administrator using reflective questions such as:
- What parts of the process felt most helpful to you?
- Did you gather any new language, strategies, or ideas you might use in your own pre-observation conversations?
- How did this experience shape the way you think about reflection with teachers?
- Where do you see opportunities to adapt this process to fit your own leadership style?
- What might you keep, adjust, or try differently the next time you conduct a pre-observation?
- How will you make this process your own so it feels authentic in your practice?
Moving Forward
One thoughtful observation, done with intention, can shift practice in ways that resonate across classrooms, teams, and even school communities. That’s the kind of leadership I aspired to when I was in the classroom, and it’s the kind I aim to provide now.
So when I return again to that question: What type of leader do you wish to be? The answer remains the same: the type of leader I always needed. The kind who mentors, coaches, and reflects alongside others.
Because teaching, learning, and leading is a calling. Every observation, every conversation, every pause to reflect is an opportunity to unleash the potential in others. And in doing so, we discover a little more of the potential inside ourselves.
And I’ll continue to share more parts of the observation process in future posts, because every stage from pre-observation, to classroom visit, to feedback matters in building the coaching culture our schools deserve.
Three Takeaways to Implement Tomorrow for New Administrators
- See Observation as Learning, Not Compliance
Shift the mindset from “checking a box” to “building capacity.” The goal is growth for the teacher and for you as the leader. - Ask Reflective, Standards-Based Questions
Ground the pre-observation in priority and content-area standards. Ask about learning activities, pathways, expectations, and assessments. Push for interdisciplinary connections when possible. - Debrief as Mentors, Not Judges
Use post-observation conversations to affirm strengths and co-construct next steps through a coaching mindset. Growth happens when trust and dialogue are prioritized over evaluation.
What about you? The next time you sit down for a pre-observation, how might you use it as an opportunity to mentor, coach, and build capacity?
Empower. Collaborate. Connect. 