A Guide to Courageous Conversations for Principals

Master the art of open dialogue.

When’s the last time you had to confront a staff member concerning a dress code issue or call a parent to say you’re moving their child to a different classroom? School leaders engage in courageous conversations all the time—from conflict resolution to racial equity to performance appraisal. These difficult conversations require all parties to be honest and open. And they can’t be pushed to the side. They need attention quickly.

So, you know you’ve got to do it, but how do you make the most of those difficult situations? The following scenarios showcase the best ways to handle some courageous conversations.

Scenario: You need to talk to someone about a behavior reported by a third party.

Example: A parent calls to tell you that a teacher was crying in front of the kids. 

What to do: A difficult conversation shouldn’t begin with a “gotcha” moment where you walk in the room to ask what happened. Remember, the person may not know you’ve heard anything. Sometimes you have to deliver the bad news at the moment, but whenever possible, try to avoid an ambush and allow the person to process what happened before engaging them in conversation.

Try saying this: “I wanted to give you a heads up that I heard what happened. I want to make sure I understand, so let’s plan on meeting later today to discuss it.”

Scenario: You’ve received conflicting reports and need to figure out the truth.


Example: A teacher reports that another staff member allowed students to cheat on the state test, but the test coordinator says there were no anomalies.

What to do: All participants in the discussion need to check the validity of their own assumptions. Just because it’s someone’s truth doesn’t mean it is the truth. Don’t assume you know how someone else feels or their intentions. Getting all the information and everyone’s perspective will help you understand the complexity of the situation.

What to say: “Tell me what happened.” (Then listen without judgment!)


Scenario: You’re knee-deep in emails and evaluations when you’re interrupted with a crisis.

Example: A student comes to your office and discloses mental health concerns.

What to do: Treat each courageous conversation like the most important one you’ll ever have with that person. Silence your phone. Close your laptop. You can’t give the discussion your full attention if you have distractions. When you’re physically, mentally, and emotionally present, you can really listen to what someone else is saying (not just the words, but the emotion and intent behind them).

Try saying this: “I hear you saying…” (Active listening will keep you focused.)

Scenario: Someone did something that really angered you.

Example: A teacher fails to show up to work and didn’t put in for a substitute.

What to do: Even if you are angry (and justifiably so), you can be compassionate. Everyone screws up. No, it’s not acceptable for a teacher to leave no sub plans, but there may be a good reason for it. Even if there isn’t and you take disciplinary action, that doesn’t preclude being kind or preserving dignity and respect.

Try saying this: “I care about you, and I need to know if you need help.”

Scenario: You have to bring up an issue that’s really uncomfortable for you.

Example: A student’s personal hygiene is causing a problem. 

What to do: We tend to avoid confrontation. By having a courageous conversation, you’re taking a situation head-on. But it’s perfectly okay to acknowledge that the conversation is uncomfortable and even talk about why. Likewise, it’s fine for silence to occur. Sometimes the best insights arise when we allow ourselves space within the conversation to reflect. 

Try saying this: “This conversation is hard for me, but I think it’s important to address.”

You can use courageous conversations for:

  • Performance evaluations 
  • Instructional coaching/mentoring
  • Improvement/growth plans
  • Promoting equity and inclusion
  • Inappropriate or problematic staff behavior
  • Conflict between staff members, students and staff, and parents and staff
  • Student behavior that merits parental involvement

Additional Resources

What kinds of courageous conversations are you having in your school? Come share in our Principal Life Facebook group. 

Plus, Simple But Effective Ways School Leaders Can Show Teachers They Care Every Day

A Guide to Courageous Conversations for Principals