Crafting Courageous Conversations: 5 Maxims for Everyday Leaders

As educators, we are in the people business. Yes, we deal with curriculum and instruction daily but the currency of our profession is founded in relationships. We are also in the continuous improvement process daily and that include coaching others and having those conversations that many may feel inclined to shy away from. We can all remember that first difficult phone call or conversation with a parent. It wasn’t easy, but we survived. But, what happens when the “issue” is with a colleague?

By and large, educators are pleasers, and we don’t seek out confrontations. College may have prepared us with the theoretical constructs on many educational issues, but somewhere along the way we all missed the class on giving and receiving constructive feedback.  Yet, real understanding in how to approach, prepare for, and execute courageous conversations with others is crucial for the success of any leader.  In educational leadership roles with several decades of experience we have found “5 Maxims for Courageous Conversations”. If you are a leader you can’t avoid them.

Maxim #1: A Courageous Conversation is about crafting constructive communication, not collisions.

This first maxim is based on a presumption of wanting to see others and yourself get better, it’s all about continuous improvement.  Courageous conversations are often not welcomed, but they have the power to transform a relationship. Rather than seeing an impending collision, find the benefit in dealing with an issue head on and up front. Yes, it may be uncomfortable to discuss a problem with another person, but when it comes to the “why”, we need to have the conversation considering that the positive outcomes will outweigh the negative ones.  When sitting down with another person, be certain that your own personal intentions are grounded in finding common ground, keeping your sight set on solutions and creating a shared dialogue. ~Jeff

Bottom Line: Courageous conversations avoid creating winners or losers. You will both gain relational credibility with one another.

Maxim #2: A Courageous Conversation is one in which leader takes his/her work personally and leads with heart.

Advice to leaders entering difficult conversations is typically filled with maxims like “don’t take this personally” or to relax and “not take yourself so seriously.”  In the book Fierce Conversations, Scott asserts that these suggestions are misguided.  She, instead, urges leaders to take themselves and their work personally and seriously.  Leading courageously is “seriously personal” business.   When leaders take their work seriously personal, they come out from the behind the conversation, that is the safety of pleasantries and the futile efforts to placate others, and make it real.   

When leaders step out from behind the conversation and passionately cement their spirit at the forefront, people recognize it and respond.  Because it happens so seldom, people are touched and influenced by leaders who courageously show their true selves.  They are willing to get behind a leader who is passionate and authentic.  They are willing to take his/her words and transform them into action. ~Paul

Bottom Line: Courageous conversations are ones in which the leader takes the work seriously personal, showing his/her true self and influencing others to take action.

Maxim #3: A Courageous Conversation is grounded in clearly defined and communicated core beliefs.

Many times, leaders find themselves in a position of regret wishing they would have communicated expectations or actions earlier in a process.  Then, they find themselves in a position needing to “back-track” to the intended purpose or intention.  In his book Focus, Mike Schmoker shares the importance of being “explicitly clear” in communicating the expectations up front and throughout a process.  When the leader explains his/her core beliefs, it makes it easier for others to anticipate direction and intent of leadership decisions. ~Neil

Bottom Line: Courageous conversations about beliefs up front avoid uncertainty or misconceptions among the team.

Maxim #4: A Courageous conversation is listening for understanding, not listening to reply.

We have all been there, having that conversation with someone and feeling like they are looking past you wondering if they are even listening. Your body language, where your eyes go,  and tone in the conversation is a key indicator of if you are listening. Having a courageous conversation is about allowing both sides to give input. In order for this to happen effectively, you must resist the urge to respond to every comment or explain yourself. Every time you redirect the conversation back to you, you put the focus, well, back on you. -Jeff

Bottom Line: A courageous conversation is about active listening.

Maxim #5 – A crucial conversation is essential if we want to bring about lasting change to our school culture and school community.

In School Leadership That Works, Robert Marzano describes the difference between first and second-order change: first order is incremental, and in many cases, it can be easy and manageable.  It’s something like changes to playground supervision schedules or school dress code policies.

Second-order change requires more than just talking about a problem…it requires action…and it can be emotional.  This is why crucial conversations are so vital…they bring to the surface the uncomfortable and the difficult, and they ask us to address them in a way that will impact our school’s culture.  This is the type of change that people fight against because it is going to go against the adage of “that’s the way we have always done it.”  Bringing this level of change can be paradigm-shifting, but it can also lead to the most resistance and reticence from nay-sayers.  Thus, it requires us to reflect on whether or not this is “the hill we are willing to die on.”  If it is, this crucial conversation must be undertaken if it is going to positively impact kids and their learning. ~ Todd

Bottom line:  A Courageous Conversation is one that brings about second-order change.

Bringing It All Together

Courageous conversations are powerful opportunities to influence lasting change in a person. You should end the conversation asking if there is anything additional that they may need for support or to move forward. Your goal is to set that person up for success. When engaging in this work we need to be mindful to check our motives, remembering our goal should never be to take something from the other person but to add value.  Peter Drucker reminds, “Leadership is not magnetic personality, that can just as well be a glib tongue. It is not “making friends and influencing people”, that is flattery. Leadership is lifting a person’s vision to higher sights, the raising of a person’s performance to a higher standard, the building of a personality beyond its normal limitations.”


This piece was a collaborative effort on the part of the co-leaders within LeadUpNow & #LeadUpChat – Jeff Veal, Dr. Neil Gupta, Paul Erickson, and Dr. Todd Schmidt. Though we serve as administrators in four different states our commitment is the same. Together, we are committed to changing the tone of education and building capacity in the everyday leader whether in the classroom or conference room. 

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