Steven Sample – The Contrarian’s Guide to Leadership

It’s essential for an expert to be a deep specialist and for a leader to be a deep generalist. The expert’s rolle is to offer greater insight than the leader has in one or a small number of areas, while the leader’s rolle is to be sufficiently broad so as to be able to integrate the advice of several experts into a coherent course of action

Learn from the classics, the books that survived hundreds or thousands of years. The Bible, the Qur’an, the Bhagavad Gita, the Pali Canon of Buddhism, the Analects of Confucius. Plato’s Republic, Aristotle’s Politics, the plays of Shakespeare, the plays of Sophocles, Dante’s Divine Comedy, Homer’s Illiad and Odyssey, Montaigne’s Essays, Cervantes’ Don Quixote, Machiavelli’s The Prince. Virgil’s Aeneid, perhaps the plays of Aeschylus, perhaps something of Plutarch, perhaps Beowulf or Chanson de Roland or Chaucer’s Canterbury Tales or Maimondes Guide to the Perplexed or More’s Utopia. The point is not whether the list contains twelve or twenty or even fifty ntries; rather, the point is that the list is extremely short.

[Facing really difficult moral choices] is the essence of good leadership, and often of effective leadership as well.

Work for those who work for you. You should be doing everything you can to help your direct reports succeed. You should be the first assistant to the people who work for you.

The contrarian leader knows that telling compelling stories is one of the most powerful tools there is for establishing a close bond with his followers and for inculcating his vision among them.

Think gray: try not to form opinions until you have to.
Think free: consider really outrageous solutions and approaches.
Listen first, talk later.
Don’t substitute experts for your own critical thinking and discernment.
Beware of pseudoscience masquerading as incontrovertible fact or unassailable wisdom.
Dig for gold in the supertexts while your competition stays mired down in trade publications and other ephemera.
Never make a decision that can be delegated. never make a decision today that can be made tomorrow.
Ignore sunk costs and yesterday’s mistakes.
Don’t humiliate a beaten opponent.
Know which hill you are willing to die on.
Work for those who work for you.
Many want to be a leader, but few want to do the work required.
You cannot run your organization, you can only lead individuals, who then collectively give motion to the organization.
Work to bring out the best in your followers (and yourself) while minimizing the worst.
You can’t copy your way to excellence.