
A Quick Guide to Honest Conversations
One-on-one check-in questions that help school leaders open honest conversations.

A one-on-one check-in guide with questions and phrases that help school leaders open honest conversations, so staff feel safe sharing concerns, ideas, and feedback.
Why try it
Open honest conversations by starting with curiosity, listening before responding, and closing with a clear next step. These one-on-one check-in questions give you specific language to use so staff know it's safe to bring you what's really on their mind, and build psychological safety at work over time.
What's included
Browse the printables included with this resource.
Instructions
Open with curiosity
Start with an open question that invites sharing. Try "What's been on your mind lately?" "How are things really going?" or "Is there anything making your job harder than it needs to be?"
Listen before you respond
Ask follow-up questions and acknowledge what you're hearing before offering a solution. Use phrases like "Tell me more," "That sounds frustrating," or "Thanks for sharing that with me."
Close with a next step
Agree on one action before the conversation ends and thank the person for being honest. Ask "What's one thing I can help with?" or "Can I follow up with you next week?"
Keep the included Conversation Cue Card nearby during the check-in as a quick reference for questions and phrases at each stage of the conversation.
Activity variations
Adapt to fit your school's vibe, budget, and setting.
Hallway moments
Use one question from the guide during a quick classroom visit or hallway conversation.
Leadership team
Share the guide with assistant principals and instructional coaches so staff experience the same approach from every leader in the building.
New staff check-ins
Use the guide during a new hire's first 30 days to build trust early.
Go deeper
Additional tips for running this resource.
Leader tip #1
Skip loaded questions
Avoid phrasing that puts someone on the spot, like "Are you open to feedback?" Open questions invite more honest answers.
Leader Tip #2
Follow through after
Note the action you agreed on and follow up when you said you would. Following through is what builds trust for the next conversation.
Leader Tip #3
Watch for hesitation
If someone pauses or hedges, slow down and give them space before moving to the next question.
Built by Educators, for School Leaders
This resource was created in collaboration with passionate educators and school leaders who believe in the power of intentional connection.
Alissa Christensen
Head of Customer Success

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