Machiavelli’s advice to a new ambassador five centuries ago reminds us that the experience and wisdom of the diplomatic practitioner are unique and timeless.

BY DAVID B. SHEAR

Niccolò di Bernardo dei Machiavelli (1469-1527).
Palazzi Vecchio

In 1522 Niccolò di Bernardo dei Machiavelli (1469-1527) dispatched a letter on how to be a good diplomat to Raffaello Girolami as the young man prepared to serve as the Florentine ambassador to Emperor of Spain Charles V. “Having had some experience in [diplomatic] affairs,” Machiavelli wrote to this son of a close friend, “I shall tell you, not in presumption but in affection, what I have learned about them.”

Machiavelli was, indeed, an experienced diplomat. He had joined the Florentine Signoria, responsible for the city-state’s foreign affairs, in 1498, and during a 14-year career there he had been sent on multiple diplomatic missions within Italy, as well as to France and Germany. The Signoria’s records are replete with Machiavelli’s diplomatic correspondence.

By the time he wrote to Raffaello, however, the “Florentine Secretary,” as Machiavelli liked to be known, had been in exile for a decade. His Medici enemies had returned to Florence on the apron strings of a Spanish invasion in 1512, abolished the Florentine Republic, and reinstituted family rule. The Medici imprisoned, tortured, and finally exiled the statesman to his suburban estate. To Machiavelli’s enduring despair—albeit to the benefit of modern political thought—he never returned to public life. It was during this time that he wrote two major works, The Prince and Discourses on the First Ten Books of Titus Livius.

He also took pen in hand to coach a new Florentine ambassador. Why would the exiled statesman, likely still bitter, have wanted his enemy’s representative to Spain to succeed? Machiavelli clearly treasured Raffaello as the son of a friend, so it must have been partly out of such sentiment that he offered his advice. But perhaps it was also out of a continued love of his country and a wish for its survival in the emerging, deadly, game of nations—despite the fact that the city-state remained under his torturer’s rule.

An Ambassador or a Prince?

The elder statesman begins his “confidential instruction” by remarking that the greater the difficulties Raffaello faced as an ambassador, the greater the honor his countrymen would confer on him. Machiavelli continues: “Above all, a representative must strive to get reputation, which he does by striking actions which show him an able man and by being thought liberal and honest, not stingy and two-faced, and by not appearing to believe one thing and say another.” Those diplomats who are judged by their hosts to be duplicitous soon lose all trust as well as their sources of information, he explains.

This does not sound like the Machiavelli we thought we knew. That would be the much-maligned author of The Prince, who argues: “One sees from experience … that the princes who have accomplished great deeds are those who have thought little about keeping faith and who have known how cunningly to manipulate men’s minds; and in the end they have surpassed those who laid their foundations upon sincerity.” Perhaps Machiavelli is making a distinction between ruling as a prince and conducting diplomacy as an ambassador. For, as we shall see, the task of the ambassador is not to establish rule over his rivals, but to build bonds of trust with the host-country elite.

Or maybe there’s not that much difference between the prince and the ambassador, after all. Machiavelli does not urge Raffaello to be a good and just man, but to “[act] on every occasion like a good and just man” (emphasis mine). Here we recall a passage in The Prince in which Machiavelli argues: “It is not necessary for a prince to possess all of the above-mentioned [virtues], but it is very necessary for him to appear to possess them. Furthermore, I shall dare to assert this: that having them and always observing them is harmful, but appearing to observe them is useful.”

Returning to the letter, Machiavelli seems to certify the latter interpretation by counseling Raffaello: “And if … sometimes you need to conceal a fact with words, do it in such a way that it does not become known or, if it does become known, that you have a ready and quick defense.”

What Makes a Good Ambassador?

But what, for Machiavelli, makes a good ambassador? In his book The Arts of Power (USIP, 1997), former Ambassador to Saudi Arabia Chas Freeman enumerates the tasks of the modern diplomat. According to Freeman, diplomats act as agents of their government. They are advocates of their government’s policies and negotiate on its behalf. They establish facilitative relationships with host-country elites, report on and analyze local developments, and recommend to their government courses of action designed to advance national interests. Diplomats protect their compatriots, promote trade, and cultivate a positive image of their home country, Freeman adds.

The ambassador’s job as Machiavelli describes it in the letter to Raffaello, however, has a narrower scope. He focuses on conducting contact work, arriving at judgments on the basis of information derived from contacts, and reporting these effectively to the home government. Perhaps the mentor limits the ambassador’s field of play to these three areas to keep things simple given Raffaello’s inexperience, which Machiavelli points out at the opening of the letter. The functions of the chief of mission had not been fully established in Machiavelli’s day, and it isn’t clear what powers the Medici had conferred on Raffaello. The text does not reveal whether he had been assigned only to report on events in Madrid or whether he had the power to negotiate and conclude agreements.

Developing contacts is Machiavelli’s first concern, and the ambassadorial contacts most worth knowing are the sovereign and the courtiers immediately around him who know his thoughts and his character and who could obtain a good reception for the new chief of mission. “Any difficult business, if one has the ear of the prince, becomes easy,” according to Machiavelli. In other words, access is everything. But Machiavelli continues later on that the king and his immediate advisers should not be the only objects of the ambassador’s attention. Royal courts are always filled with busybodies, Machiavelli says, who make it their business to know what is going on, or at least to know what is rumored to be going on, and these people can be cultivated with banquets and entertainments.

The goal of contact work is to obtain information, or intelligence, on what important actions have been decided, what actions are in the process of being decided or are under negotiation, and what will likely happen in the future. While it should be easy to determine what decisions have already been made, diplomatic decisions of great importance to the home government, such as the conclusion of a secret alliance detrimental to the ambassador’s prince, are very difficult to uncover. The ambassador can only use his judgment to conjecture or surmise what may be happening in his host court, and Machiavelli suggests, vaguely, that the way to do this is to develop hypotheses based on contacts and to test those hypotheses on the basis of further contact work.

The task of the ambassador is not to establish rule over his rivals, but to build bonds of trust with the host-country elite.

Finding out what your own capital needs to know is crucial. In Raffaello’s day, as at present, knowing who in the host-country court is doing what to whom was an important piece of the puzzle. Machiavelli urges Raffaello to observe the emperor’s character and intentions toward Italy closely, find out what kind of men he relies on for advice and whether or not they can be bribed, determine the extent of Spain’s current relations with France, assess conditions in Spain and its territories, and judge the possible effects on Florence. To get something, you have to give something. Diplomats and courtiers are not in the habit of providing information for nothing. Machiavelli therefore urges Raffaello to ensure that home office officials provide him with as much background on events in Florence and other capitals as possible, because a “city which wants her ambassador to be honored can do nothing better than to provide him abundantly with reports, because men who see that they can get something are eager to tell him what they know.”

Effectively reporting what you know is also crucial. According to Machiavelli, ambassadors with all the right judgments may yet tarnish their reputations if they fail to report what they know. Machiavelli suggests that the newly arrived ambassador report his first meeting with the emperor immediately, following up with a broader report containing more general first impressions of his new host country. Machiavelli continues that regular, periodic reporting on Spanish conditions will greatly facilitate decision-making in Florence and enhance Raffaello’s reputation. Machiavelli even offers advice on how to couch embassy judgments in individual reports, explaining that in uncertain circumstances it would appear presumptuous for an ambassador to make an outright prediction as to what might happen. Rather, Machiavelli urges Raffaello to disguise his judgments as “the views of thoughtful local observers.”

Ageless Wisdom

In their book Diplomatic Theory from Machiavelli to Kissinger (Palgrave Macmillan, 2001), G.R. Berridge, M. Keens-Soper, and T. Otte claim that the Florentine Secretary’s missive “is little more than a codification of the conventional wisdom of the age.” But the text still speaks to us because we practice such an ancient art. As diplomats, we face the same kinds of challenges that Raffaello faced almost five centuries ago. Newly confirmed American ambassadors, some career professionals, some political appointees, depart for post all the time, just like Raffaello. Their predecessors offer up advice, just as Machiavelli did. Now, as in Machiavelli’s day, new chiefs of mission must gain the confidence of their hosts, scour capitals for information, and furnish their home governments with reliable judgments about how the news of the day affects their national interests.

More deeply, now as then, home offices’ insatiable need for diplomatic reporting poses timeless problems in knowledge, judgment, and action. An ambassador facing a crisis in the host country never has all the information necessary to make a perfectly informed decision. The problem of knowledge is compounded, as Machiavelli well understood, by the tendency of governments to veil their communications and decision-making. The able ambassador’s only choice in a situation characterized by ignorance is to spread the contact net as widely as possible, draw in every bit of information available, even the wildest rumors, and form a hypothesis that can be further tested about what might be happening on the basis of the information available and on the ambassador’s best instincts. The use of an embassy’s entire staff in the effort is essential.

The new American ambassador or the inquiring American diplomat, curious about the intellectual foundations of his or her calling, may be tempted to turn first to international relations theory for an understanding of the relations among states. Or one might turn to think tank or war college strategists for a view of how they, as diplomats, relate to the other tools of statesmanship: the economic policymaker, the military officer, and the spy. Or one might explore American diplomatic history to determine how our policymakers have addressed historic issues in U.S. foreign relations. But all of these avenues converge in the thoughts and actions of the actual practitioners of diplomacy, and it is the experience and wisdom of the practitioners, like Machiavelli or Benjamin Franklin, any of the Adamses, or Henry Kissinger, that have the most to tell us.

And because we practice such an ancient art, the words of Machiavelli seem as fresh to us now as they no doubt did to Ambassador Raffaello Girolami.

David B. Shear spent 32 years in the Foreign Service. He served in Sapporo, Washington, D.C., Tokyo, Beijing, and Kuala Lumpur, and finished his State Department career as U.S. ambassador to Vietnam (2011-2014). Ambassador (ret.) Shear also served as assistant secretary of Defense for Asian and Pacific security affairs from 2014 to 2016.

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• “Talking with Machiavelli” by Win McCormack, The New Republic, September 2022
• “Peaceful Erosion? Trump, China, and the dual crisis in America’s Asia policy” by David B. Shear, United States Study Centre, October 2017
• “Why We Should Study China’s Machiavelli” by Franz-Stefan Gady, The Diplomat, January 2015