Trump Taught Me...

Recently, the United States concluded the presidential election process. The outcome was the unlikely and very controversial election of Donald Trump as president. I, like many others across the world, watched in awe, as the voting results were confirmed and eventually, Hillary Clinton conceded the election. Over and over, both citizens and media alike asked, “How did this happen?” Unlike some, I did not consider the question to be rhetorical. As I mentally replayed Mr. Trump’s path to victory, again and again I noted the consistent narrative of those who supported him. At rallies, in interviews and in commercials, Trump supporters repeatedly retold their personal stories, their narrative of simply being heard and understood. In the book Learning and Leading with Habits of Mind, Costa and Kallick describe what they call 16 essential characteristics for success. These characteristics – Habits of Mind – provide a better understanding of the ways in which intelligent people approach their work and lives in general. One Habit of Mind, which spoke profoundly to me, was Listening with Understanding and Empathy. I believe this Habit of Mind is the most important of those asserted in the book. According to Costa and Kallick:

“People who demonstrate this Habit of Mind are able to see through the diverse perspectives of others. They gently attend to another person, demonstrating their understanding of and empathy for an idea or a feeling by paraphrasing it accurately, building upon it, clarifying it, or giving an example of it (Costa & Kallick, 2008, p. 20).”

While Democrats spent vast amounts of time telling potential voters what to think or feel, Donald Trump brilliantly listened to a large cross-section of the country who felt that the issues most important to them were being ignored. He listened to them intently and then rephrased their concerns, fears and values in ways that connected them to him inseparably, so much so that they were able to forgive or overlook many other instances of otherwise reprehensible behavior.

Fences, by August Wilson tells the story of an extended black family and how their individual stories, morals and relationships were affected (and perhaps driven) by the patriarch of the family – Troy Maxon. Troy was a frustrated man who was unable to pursue his passion and love for playing baseball and instead suffered the reality of working as a garbage man and relived his brother’s sacrifice – who lost half his head in World War II, while fighting as a black man on behalf of a racist and ungrateful country. In the course of dialogue, Cory, Troy’s son asks,

“How come you ain’t never liked me (Wilson, 1986, p. 37)?”

Troy’s response, which followed, reminded me very much of the one-directional scolding Democrats engaged in with would-be Trump surrogates and voters over the last eighteen months. In it, Troy seeks to educate Cory about all the ways in which he supports Cory (because it is his responsibility) and why Cory, as a man, should ensure that he is given whatever is owed to him. Had Troy been a more active and perceptive listener, someone striving to understand rather than to be understood, he would have seen clearly that Cory was attempting to connect with his father and have his father simply say “I love you.” Much in the same way, Hillary Clinton failed to hear, empathize and paraphrase the concerns of a vast amount of Americans and articulate to them the love that they so desperately sought to hear. By contrast, Donald Trump did so effectively, resulting in his supporters declaring, “He’s just like me!” when asked why they voted for him and why they are so fanatical in their support of him.

In school leadership, one’s ability to listen well and empathize with those around you is critically vital to your own success and the success of the overall organization.  As I reflect on my career as an educator, I recall one particular experience that gives me reason for pause.  In 2005, I was given the opportunity to join the staff of a new middle school in Washington Heights, New York; an area of the city well known at that time for its high concentration of newly emigrated Spanish speaking families – particularly from the Dominican Republic.  This was the start of the small school and empowerment movements, where schools and school leaders were given autonomy over their instructional models/methods and budgets.  It was a great time to be an innovator in education.

As a first-year dean, my responsibilities were to establish structures and systems around student discipline, entry, lunch, dismissal, student of the month, detention and suspensions.  The role required that I create and establish procedures to ensure that these initiatives functioned effectively.  This meant that I needed to communicate a vision with strategic precision to all stakeholders (students, parents, staff, teachers and administration) and continue to keep those lines of communication open at all times.  At first, all the systems that had been created and implemented functioned smoothly and as planned.  Over time however, I found that one group of stakeholders had difficulty trusting me.

Attempting to be reflective, I tried to figure out why some parents with whom I had scheduled face-to-face appointments preferred to speak with other staff members. At the same time, I began to hear students referring to dark-skinned students as Mexicans. A few students even called me a nigger. It was then that I realized that although I had done nothing wrong, I was unable to gain the trust of some parents due to my inability to simply communicate with them in their own language. When these parents arrived at the school, they found it less stressful to speak to other staff members who could communicate effectively in Spanish. This deficit on my part led some parents to distrust me and to assume that I disliked them and or their children because they spoke only Spanish.

By the end of that school year, although I had built strong relationships with many parents, who served as surrogates in affirming my character and intentions to others in the community, I relented over the gaps I was unable to close with other parents.

“The perilous thing…is that you are never forced to hold the mirror up to yourself. No one ever asks you to evaluate your actions, your motives, your intent, and so you continue on with no points checked and no questions asked (Matlwa, 2010, p. 4).”

As I reflect on the year I worked in that school, holding the mirror up to myself, I realize now, on a very foundational level, that the human desire to be heard and understood is critical to building strong relationships. This is of paramount importance! A conversation cannot begin if someone does not first know that you will hear and understand him or her. In my example above, although I understood much of what was being said to me in conversations with these parents, I could not effectively engage in the conversation by paraphrasing and connecting to their concerns and fears. Rightfully so, if I could not understand all that was being said, how could I empathize and meet parents where they were emotionally in that moment? This was especially true as my reason for contacting parents was often to discuss matters relating to the safety and or discipline of their child.

As leaders, we must endeavor to begin by first seeking to understand and empathize.

“A place where the elderly listened to the young and the young took the podium and led. A place of pride. A place of truth….For how else could things change if not at the very beginning (Matlwa, 2010, p. 5)?”

This is the embodiment of why this is the most important Habit of Mind. This is a lesson we as a country could learn as we attempt to forge a path forward that does not focus on one viewpoint over the other, but instead, seeks an empathetic conversation where each party seeks to listen and understand, rather than seeking to speak over others.

“In the end, they may disagree sharply, but because they have truly listened, they know exactly the nature of the disagreement (Costa & Kallick, 2008, p. 21).”

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"Biased people bias people. Better people better people." - David Martin


Costa, A. L., & Kallick, B. (2008). Learning and Leading with Habits of Mind: 16 Essential Characteristics for Success. Alexandria, VA: Association for Supervision and Curriculum Development.

Matlwa, K. (2010). Spilt Milk. [Kindle]. Retrieved from dp/B008BAHPRW/ref=tmm_kin_swatch_0?_encoding=UTF8&qid=1479238840&sr=1-8

Wilson, A. (1986). Fences. New York, NY: Plume Books.