Coaching Questions 201: Advice from School Leaders

Last month we began exploring how to improve on different aspects of the questioning process in a coaching conversation. The Whetstone team wants to harness the knowledge of some of our brilliant partners in this work to give their first hand experience and advice when it comes to asking the right questions. The school leaders we polled for this month have great experience as coaches and are probably in a coaching conversation as you are reading this. We polled them on 4 simple questions so they can relay their insights and experiences to you to improve your coaching. Here’s our team of experts for today’s post:



Joshua Cella

Assistant Principal

Phillis Wheatley Community School

New Orleans, LA






Michelle Anderson

Director of Literacy

New Heights Academy

New York, NY






Brionne Stewart

Assistant School


Young Audiences Charter

New Orleans, LA





Michael Richard

Former Principal

Current Director of Sales at Whetstone

New Orleans, LA


What questions do you ask to facilitate self reflection for a teacher?

Joshua: For our experienced teachers whose classes have more nuanced next steps, I like to ask them what they want to work on in advance, so I can then reflect with them in our check-in after I observe their focus area. For teachers with more clear next steps, often management-centered, I find having them self-record and send me their areas of growth to be an effective method to start teaching self-reflection.

Michelle: Was your objective met? How do you know? What were students asked to do? Is this what you expected?

Brionne: What went really well in the lesson or what do you feel really good about and what would be your "even better ifs"? I then normally elaborate and build upon their responses or ask a targeted reflective question based on the target of the coaching session.  E.g. How does communication of the learning target impact student achievement?  What is your educational philosophy and how do you think they impact your everyday instructional strategies?  What instructional strategies most align with your educational philosophy and why?  How do you know that all learners are mastering the learning target of the day within the lesson?  

Michael: “How did it go?” And “How do you know?”  The second is so important because it should all be grounded in data.

What have you learned as a coach about how/how not to ask questions?

Joshua: I have learned to always strive to find a balance between being directive (when necessary) and inquisitive whenever possible--this balance is best for relationships, for students, and for teachers.

Michelle: Questions should be open ended and not sound leading by using words like "should" or phrases like "How come…?"

Brionne: I have learned that you should start with people's beliefs, build relationships and then guide them through reflection.  It is important to get to know your staff as an educator in order to effectively coach positive change.

What is a question you received as a teacher or leader that left an impact on you?

Joshua: One that forced me to reflect on positive teacher moves: What did students do well today? What was the teacher move that unlocked that?

Michelle: Does this product represent my best work?

Any other insights on questions?

Joshua: Don't forget to ask the person how they're feeling.

Brionne: Questions are tricky.  You have to be genuinely interested and invested in their success as a teacher and sometimes questions make teachers feel the opposite.  Coaches must let teachers take the reigns of their learning or TEACH the teachers how to do so with reflection within a coaching session.  Active listening is just as important as questioning in sessions.  

Michael: Very general questions promoting self inquiry also provide insight to the coach by highlighting what the teacher is focused on.  Coaches should follow up with questioning that guides inquiry elsewhere as needed.


The Whetstone team sincerely thanks Joshua, Michelle, Brionne, and Michael for the dedication to their students and staff and for sharing their wisdom with us. We sincerely hope you’ve picked up a few extra questions for your coaching toolbelt so you can try something new in your next coaching conversation. If you have any coaching areas you’d like for us to explore later down the road, please email

Thanks for tuning in!

The Whetstone Team