7 Keys for Courageous Conversations by School Leaders

One of the hardest things to do as a leader is to have a courageous conversation with a staff member. These conversations are awkward, uncomfortable, and typically against our nature as leaders. However, these conversations are needed to move the school forward, to strengthen school culture, and to raise the level of teaching and learning in your school. Challenging the status quo, asking tough questions, and digging into unhealthy attitudes and behaviors for the betterment of students is an important skill set for all leaders.   

Check out these 7 Keys to Courageous Conversations: 

  • Do It Now – I can remember as a young leader putting off the difficult conversation hoping it would go away or that maybe someone else would intervene on my behalf.  I found that this only made it worse and more intimidating.  By waiting, I stress over the conversation and it leaves too much of a gap in time. Now, after years as serving as a leader, I work to have the “courageous conversation” sooner rather than later.  Waiting only causes anxiety.  Don’t be the kind of leader who schedules a meeting with the person you are planning on having the conversation with on a Monday so they have to stress and worry all weekend.  This is what manipulative leaders do who work to invoke fear in people.  Instead, treat the person as you would want to be treated.  Hold the conversation as soon as possible, don’t delay, do it today.
  • Remain Calm – Nothing can halt the progress made in a “courageous conversation” more than the leader losing their temper, being sarcastic, or making snide remarks. Regardless of the topic or message, it’s important to be professional, respectful, and representative of the behavior that you would like to see from your teachers. Take a minute to talk out the conversation in your head and different ways it can go.  This will help you to be ready and to remain calm. Whatever you do, don’t get emotional, be calm, respectful, and firm. You can send a very strong message without overreacting or becoming emotionally charged.
  • Teamwork – Many times, these conversations are best with a colleague by your side listening and taking notes. If you are the only leader in your building, ask a leader from another school or the district office to support you. This helps in corroborating what took place, documenting the meeting, and providing another perspective. Plus, if you aren’t comfortable with courageous conversations (and not many of us are), this allows you to have a support network and someone to encourage you.
  • Just the Facts – This can be a hard one, but it’s important that you stick to the facts. Too often we like to interject our own opinions, feelings, and emotions into the conversation. By sticking to the facts, the conversation focuses on the behavior that needs change, the action that needs to take place, or the attitude that needs adjustment. By sticking to the facts, we free ourselves up from getting emotionally charged and we focus on the mission of the meeting. I like to document the facts as I know them before the meeting and outline some general questions that I may ask during the conference. Be focused and stick to the facts. 
  • Mission Control – Never move away from the focus of doing what is best for students. When we begin to compromise this mission of doing what’s best for students, to appease adults, we slowly chisel away at the mission of serving All Students, No Matter What! This requires us to remain laser focused on the mission, vision, core values, and goals of the organization.  
  • Let It Go – Again, as a young leader these conversations would stick with me long after they took place. I learned that I was carrying the baggage of these conversations home with me and it began to impact my level of joy in my role as leader. Now I focus on putting these conversations into perspective, realizing that we all need a “courageous conversation” at some point, and moving onto the next task. I work hard to not carry these conversations with me and to replay them in my mind. When I continue to ponder on the conversation, I find myself either second guessing myself or looking at the person differently. It’s best to have the conversation and then move on.  
  • Stay Close – Don’t shy away from the person after the “courageous conversation.” Treat them as you treat your best staff member. Respect them, honor them, and embrace them as a key team member. We always say leadership is about relationships, this is where that mantra becomes a reality. Set clear expectations, expect positive results, and let them know that you believe in them and that they can change their behavior/attitude/action. By doing this, others see that failure isn’t final and it creates a culture of trust and respect. Work to show care, respect, and love. That’s right, I said “love” because love is willing to look past the mistakes and errors to see the best in someone.    

Remember, these “courageous conversations” are not easy, but they are worth it to improve your school culture. Take a few moments and reflect on the Courageous Conversations self-reflection and work to identify your areas of strength and areas needing improvement.   


To read more, check out Bill Ziegler’s book, Future Focused Leaders: Relate, Innovate, and Invigorate for Real Educational Change. 

Written by

Dr. Bill Ziegler is Principal of Pottsgrove High School, the 2016 Pennsylvania Principal of the Year, and a 2015 National Association of Secondary School Principals Digital Principal Award Winner.  He serves as a Board Member for the National Association of Secondary School Principals. Bill is an author and educational consultant with Corwin on School Leadership.  He also served as the President of the PA Principals Association and is an adjunct professor in Temple University’s Department of Education. Twitter: @drbillziegler | Website: chaselearning.org . Podcast:  Lead the Way

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