Crafting Courageous Conversations: 5 Maxims for Everyday Leaders

Crafting Courageous Conversations: 5 Maxims for Everyday Leaders


As educators, we are in the people business. Yes, we are about curriculum and instruction but the currency of our profession is grounded in relationships. We are also in the continuous improvement process daily. Our roles 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.  Though we often do not welcome courageous conversations by nature, 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 intention is to find 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, we must undertake this crucial conversation 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 commit to changing the tone of education and building capacity in the everyday leader, whether in the classroom or conference room. 




Renewal. It means to make like new. Synonyms include words like restore implying returning to an original state after depletion, renovate as in repairing or rebuilding, and rejuvenate suggesting a restoration of youthful vigor, powers, or appearance. We renew library books, licenses, acquaintances, and vows. Holiday breaks renew our spirits; exercise renews our energy. Spring is the renewal of life after a long spell of winter. Our world is in a constant state of change and adaptation. Change comes in cycles of birth, growth, death, and renewal. Renewal is the acceptance of change.


John Goodlad said, “Most of us generally don’t pull up stakes and move simply because the paint on the windowsill starts to peel. And we don’t destroy our old garden and start over from scratch each time the blooms begin to fade. We do better when we exercise patience, ongoing care and while monitoring the effectiveness of that care, make adjustments where necessary. Such an approach, when applied to schooling, is what we call educational renewal.” In the words of John Goodlad, educational renewal is primarily designed for two purposes. First, renewal is to prevent current conditions from deteriorating and to address problems that arise. Secondly, school renewal aims to effect and sustain the changes that are desirable.


Educational renewal is never on a checklist as something that can be “done.” It is not a program, mandate, or initiative. It is not a mass produced package with instructions on how to fix problems by replacing what is currently happening in a school. Renewal is a way of being. School renewal includes all stakeholders- teachers, parents, secretaries, administration, custodians, librarians, students, bus drivers, etc. that collectively look at the school experience and inquire about what is working and what is not working. Everyone has a voice and ideas are shared on a regular basis. Alternatives to the status quo are examined, put into practice, and assessed to determine their impact.


The responsibility for change lies with those who can and must make the changes and who will also be affected by the changes. In a school setting, renewal may look something like providing more support and training for literacy instruction rather than replacing a whole reading program. It is different than a reform. School renewal is more about the continuous tweaking of behaviors that over time lead to a greater transformation much like a gardener prunes, weeds, and tends to other tasks that nurture the plants within a garden. And just as the soil must be primed and ready for a fruitful garden, a school’s culture must be primed and ready for risk-taking, open discussion, and change.


Unfortunately, developing a school culture that fosters school renewal doesn’t happen quickly and easily. It takes a courageous leader to clearly articulate and communicate a shared vision. Leaders must model and embody the values that they want to instill in others. They must be resourceful and understand how resources and budgets can be used to influence change strategies. Strong leaders must develop leadership skills in others by identifying strengths and finding opportunities for their staff members to lead. They must examine data, determine next steps, and evaluate the impact of those next steps. Leadership for school renewal can’t just be positional if long-term changes are expected to take root. Teacher leaders can influence the thoughts and actions of their colleagues to improve their practices. A culture where renewal thrives is created when engaging in inquiry, and reflective behaviors is a norm.


One of the greatest responsibilities of leaders is to foster a strong sense of self-efficacy in teachers and the belief that their purposeful actions can make meaningful changes in the lives of their students. Leaders must trust their teachers and communicate the belief that collectively, SMART goals can be achieved. They instill hope despite the obstacles and empower their stakeholders to create the conditions that will make educators more successful. The optimism, confidence, and determination of great leaders to persevere are infectious. Strong visionary leaders passionately inspire their staff to focus on what students are to learn and be able to do. Feedback about each student’s progress is timely and ongoing so that teachers can use the embedded structures to give students more support. Professional learning communities provide timely feedback to each teacher regarding student learning in comparison to other students so that teachers can identify their strengths and weaknesses with instruction. A PLC becomes more than just another educational acronym. The school becomes a place focused on learning. The school and the people within the school improve simultaneously. The message of “We’re all growing, learning, and improving our ability to ensure that every student is learning” is loud and it’s celebrated!


An ancient Greek philosopher, Heraclitus, said: “There is nothing permanent except change.” As educators embrace the concept of renewal in their school, changes won’t seem so daunting. Those things that work and are valuable to a school community can be retained while at the same time promote the changes that will improve educators and their practices. Small consistent changes for improvement over time lead to a level of transformation and lasting effective change. Perhaps the most common metaphor for transformation is the metamorphosis of a caterpillar. Maya Angelou said, “We delight in the beauty of the butterfly, but rarely admit the changes it has gone through to achieve that beauty.” Simultaneous educational renewal is a transformation that benefits all stakeholders as they change and grow together.


Successful leaders in educational renewal efforts must rise above the common standard. As Goodlad stated, “Our schools today desperately need innovative leaders who can dust off the narrative that implores creation of a thoughtful public, as proposed by Thomas Jefferson, Horace Mann, John Dewey, and many other distinguished scholars. We need innovative leaders who are ready and willing to challenge the status quo, leaders who can influence others in pursuit of schools that engage all students in meaningful learning toward the ultimate purpose of creating a thoughtful public willing and prepared to work toward a healthy and just democracy.”


Sandy King is an inspiring 5th grade teacher leader and admin intern in Utah who has a passion for student achievement! You can read more by Sandy at

Is This Your Stop?

Today’s post is by Ben Dickson, a forward thinking educator who currently serves as Dean for a STEM Elementary School in Reno, NV. 

I hear that train a comin’ it’s rollin’ round the bend………… +

Less than 24 hours ago the Universe conspired to punch me in the gut. Now in the grand scheme of the all that is going on in the world this was a trivial event, a speck of dust on the Universe’s cosmic karma train, but it still hurt like hell none the less.

I shot a man in Reno just to watch him die….. +

Over the last couple of weeks I’d been working towards a goal that I saw as the culmination of a lot of effort, the highest point on this particular mountain. There may have been a bit of hubris on my part, as I figured I’d dotted every eye and crossed every T, played the game and now it was going to pay off. The “do A and then B will happen” was something I put a lot of faith in.

Based on my opening sentences you can guess where this is going…

Friday 5:04 pm email

“we regret to inform you ……”

Really??? REALLY??

I hear the train a comin’ it’s rollin’ round the bend and I ain’t see the sunshine since I don’t know when…..+

We all know that train. that one full of pity, anger, self-doubt, jealousy. It’s carrying a full load of negativity and has some empty seats.

all aboard!”

Wow, that’s not what I thought was going to happen. It was like that final paper you get back after going to class everyday, sitting in front taking notes, studying until 5 am…You wonder if they even read the paper or did you forget to answer something, did you accidently hit delete before you sent it? Was it the wrong file?

“Welcome Sir, take a seat next to Mr. Second Guessing.”

Really?? REALLY??

And now here we are at 4:03 in the morning and it’s time to get off the train.

“Next stop Now What Station?”

This is not the “Now what?” of “How am I going to eat or pay my rent?” (Perspective people…first world speck of dust on the cosmic karma train)

No this is the “now what?” that we ask our students when they fail. The “now what?” of asking what are you going to learn from this? The “now what” we sometimes see in the eyes of students or staff after we deliver some bad news.

So in lieu of any actual feedback around my particular speck of dust. I realize I need to turn inward and think about what I’m going to learn from this. We often talk about resiliency and the need to build it in our students but we also need to think of ourselves. How are we dealing with professional or personal setbacks? Are we switching trains or riding the same one all the time?

Are you you on a road to nowhere?

Are you riding a train to Heaven of Hell?

Are you in search of somewhere?

Or something that rings true? *

All aboard!

Robyn Jackson talks about the need to create Master Teachers in her book Never Underestimate Your Teachers and I believe the same concepts can be applied to leadership. How can I learn to be a Master Leader? How am I making conscious decisions about what staff and students need? How am I dividing responsibility and developing the unique talents of those I work with? To me it starts with some introspection. This event has provided me with the opportunity to take a hard look at my beliefs about leadership and how I put those into practice. To think more about my interactions with staff, students and families and look for opportunities to improve, look for those chances to move from a practicing leader to a master leader. I have my own philosophy around teaching, learning and leadership but that doesn’t mean it can’t improve and evolve. How am I constantly growing?

You can get a taste of the glory

By the ingestion of a simple truth*

I think about choices I’ve made, answers to life’s questions and not just those recent ones. Would I do things different? Would I change my answers? No, those answers and choices are at the core of my beliefs about not just  teaching and learning but about being a human: build relationships, support each person with what they need at that time and have a clear shared vision. But could my answers sometimes be better? Sure. Could I take time to seek other’s answers, of course

But here’s the thing. now it’s not about whose answers are right but how they are put into practice. Once we make statements or answer a certain way they are free in the universe for everyone to agree with, change, argue about and laugh at. for me the key is not the answers or the questions but how they play out everyday in my interactions with others. How am I putting those beliefs into practice? Where are the opportunities to learn and am I taking advantage? How am I helping others find their trains? How am I switching trains?

So for now my train is headed in another direction. I might keep looking back at that other one once in awhile, wondering what could have been,  but the important thing for me is to remember that I get to pick my stops,I get to decide which way I’m going and I’m the only one to decide which seat I take and when I look out the window I’m going to see a lot more mountains.

+Folsom Prison Blues-Johnny Cash

*It Could Be Sunshine-Love and Rockets

For further reading by Ben