Samurai Sensibilities for Equipoise Educators: Revisiting Todd Whitaker’s Dealing with Difficult Teachers
Nicholas Rickards, Ph.D. Candidate
Faculty of Education, Brock University
University Lecturer & Public School Teacher
Dr. Todd Whitaker is an American orator, consultant, and writer in the field of educational leadership. Revered as a leading authority, Whitaker has a wide brand appeal that reaches from school teachers and administrators to educational scholars across North America. He has amassed an astounding following of over 150 thousand followers on X, a growing presence on Bluesky, a deep catalog of content on YouTube, and an impressive marketing machine through his personal website which sells bookings for keynote addresses like “Motivating People During Difficult Times” and “What Great Teachers Do Differently.”
At the beginning of the 2022 school year, my colleagues and I attended a webinar by Dr. Whitaker at the behest of middle management. Overall, he seems like the kind of guy I would like to sit and talk shop with, even now (Hi, Todd!). Unfortunately, the giant talking head on the gymnasium jumbotron was nothing short of Orwellian amidst the silent teachers mollified from summer break. His message that teaching is the single most important career ever was certainly ingratiating, hitting the bullseye of the profession’s hagiography, but the suggestion that the best teachers operate in full-throttle “business mode” missed the mark in a gym full of middle school educators whose tomfoolery is both an informal requirement of the work and a means of survival on the job. We must have gotten the “What Great Teachers Do Differently” keynote. Maybe admin was trying to tell us something. . .
Anyways.
The body of knowledge that Whitaker contributes to and draws upon is the science of management. More specifically, Whitaker is preoccupied with the relationship between power, people, and educational institutions; how power is conglomerated and disseminated; and how to manage, coerce, discipline, and control bodies, labour, and learning in schools. This is an ideological project as much as it is a practical one, which is why I was so interested in exploring Whitaker’s (2015) Dealing with Difficult Teachers (hereafter, Difficult Teachers).
Pitched as a manual that “provides tips and strategies to help school leaders improve, neutralize, or eliminate resistant and negative teachers,” Difficult Teachers reveals Whitaker’s (2015) impetus and market. With sections like “Part 5: Weakening the Influence of Difficult Teachers” (p. 117) and “Part 7: Eliminating Difficult Teachers” (p. 152), Whitaker’s handbook is a derivative of the diabolical treatises it clearly borrows from.
In providing detailed diagrams on how to structure seating plans for staff meetings (figure 3, p. 69), Whitaker maps a battlefield like The Art of War, without the poetic conciseness of Sun Tzu (2018). When conniving about how to upend “negative leaders” (p. 122) and “powerful teachers” (p. 138), he suggests methods like “make every attempt to work with one at a time. You want them to feel as lonely as possible” (p. 125) and “a person who feels unsupported is much less likely to resist. . . The more lonely they feel during the time you work to eliminate them the less strength they have to fight the process” (p. 155). These stratagems plot a course for a coup de grâce like The Prince, without the political vistas of Niccolò Machiavelli (2020). Relying on banal rating systems and codification of teachers as “superstars, backbones, and mediocres” (p. 11), “The Brown-Nosing Back Stabber” (p. 121), and “The Town Crier” who function as “the ‘schoolhouse lawyers’ at faculty meetings” (p. 121), Whitaker uses cookbook instructions like the Simple Sabotage Field Manual, without the bureaucratic blunt force of the CIA (2008).
Napoleon Bonaparte was obsessed with Machiavelli’s (2018) The Prince, and Difficult Teachers reads as if it had been written by an author in the grips of Bonaparte’s complex. The rationale in the preface narrates a gritty origin story straight out of DC Comics about a hero pushed to wear the cowl and seek the dawn justice because of a sarcastic colleague who yelled at and humiliated a student: “Thus, I became a principal.” By the closing chapter, Whitaker (2015) cements his heroism with cinematic aplomb when he reminds readers that “It’s up to you. There is no one else” (p. 209) and that they should “Always do what is right” (p. 211). What comes across, however, is not a righteous hero but a megalomaniac on a campaign to eliminate “challenging staff members” (p. 98), “onerous teachers” (p. 111), infidels, heretics, rebels. What Darth Sidious referred to in Star Wars: Episode III — Revenge of the Sith (2005) as “enemies of the Republic.”
The rhetoric in Difficult Teachers is troubling, not least because of what it omits. Nowhere in the more than 200 pages of the book does Whitaker (2015) address the catastrophic collapse of the American public education system, the plight of the working-class stiffs (admin assistants, educational assistants, librarians, etc.) who shoulder public schools, and the general disaffection of public education as a fragile pillar of democracy (Berkshire, 2024). Sure, Difficult Teachers comes from an American context and maybe Whitaker’s bleak origin story justifies the approach. Regardless, Whitaker is a point of reference for Canadian administrators and Difficult Teachers presents an authoritarian style of school administration, one that Canadian administrators would do well to avoid.
This is a form of leadership that has resounding effects on the labour politics of teachers, what they do, their relationships to their jobs, and ultimately, how kids are taught. What happens when teachers lose autonomy to autocrats? What happens when leadership quells dissenting voices and ideas in public schools, essential elements for civil discourse in the communities they serve? What happens when public teachers become yes-people instead of “challenging staff members” and schools end up looking more like Emperor Palpatine’s Death Star than a new hope?
Combating authoritarian politics in education requires courage and equanimity. Perhaps it is best to take a page from Inazo Nitobe’s (2020) The Way of the Samurai and remember that “things which are serious to ordinary people, may be but play to the valiant. Hence, in old warfare it was not at all rare for the parties to a conflict to exchange repartee or to begin a rhetorical contest. Combat was not solely a matter of brute force; it was, as well, an intellectual engagement” (p. 42).
Intellectual engagement, however, necessitates radical action and every educator is equipped for combat. Labour power is your katana. Our Force is the collective. Have some mercy, but do not hesitate; the samurai class was swallowed by history. The Jedi went extinct.
References
Berkshire, J. (2024). Naught for teacher: How Democrats abet the right’s war on public education. The Baffler. https://thebaffler.com/outbursts/naught-for-teacher-berkshire
CIA. (2008). Simple sabotage field manual. Chief/DRRB Declassification Center. https://www.cia.gov/static/5c875f3ec660e092cf893f60b4a288df/SimpleSabotage.pdf
Machiavelli, N. (2020). The prince. Arcturus.
Nitobe, I. (2020). The ways of the samurai. Arturus.
Tzu. S. (2018). The art of war. Arcturus.
Whitaker, T. (2015). Dealing with difficult teachers (3rd ed.). Routledge.

