Theodore Roosevelt's 20 Key Elements of Leadership

By James M. Strock, a lawyer and the author of Theodore Roosevelt on Leadership (Random House). He provides leadership Theodore RooseveltBy   development services to law firms, companies, and other organizations. His website

[Roosevelt] was . . . the greatest executive of his generation. -- Gifford Pinchot

“The leader must understand that he leads us, that he guides us, by convincing us so that we will follow him or follow his direction. He must not get it into his head that it is his business to drive us or rule us. His business is to manage the government for us.”– Theodore Roosevelt

Theodore Roosevelt is universally recognized as a consequential—indeed transformational—leader. TR defined numerous aspects of leadership that we now take for granted in the presidency as well as in private life. His inspirational vision (including environmental protection, which may be more widely comprehended in our time than his own) was certainly one element. Another was his remarkable ability to communicate his vision, not only through his well-crafted words, but even more through his indelible example. TR’s well-publicized, courageous exploits in Cuba in the brief but deadly Spanish-American War of 1898—the fateful days he viewed as the linchpin of his life—are perhaps the most apt symbol of his leadership. Mounted conspicuously on horseback, in front of and above the troops in his command, Roosevelt showed the way—asking others to “come” rather than saying “go” in the words of his friend Henry Cabot Lodge—putting himself at risk, making himself accountable, giving more of himself than he would ever ask of others.

Roosevelt was also a skilled, subtle manager. Warren Bennis and Burt Nanus make a useful distinction between the leader and the manager:

By focusing attention on a vision, the leader operates on the emotional and spiritual resources of the organization, on its values, commitment, and aspirations. The manager, by contrast, operates on the physical resourcesof the organization, on its capital, human skills, raw materials, and technology. Any competent manager can make it possible for people in the organization to earn a living. An excellent manager can see to it that work is done productively and efficiently, on schedule, and with a high level of quality. It remains for the effective leader, however, to help people in the organization know pride and satisfaction in their work. Great leaders often inspire their followers to high levels of achievement by showing them how their work contributes to worthwhile ends.

In practice both leadership and management skills are necessary to achieve organizational success. Though an individual may display both sets of skills, in many cases the different emphases required and traits utilized point toward different individuals and personality types. A leader may be conspicuous for his or her ability to present abstractions or possibilities in a compelling manner, often utilizing (to the consternation of those relying solely on analytical or quantitative approaches) artful ambiguity to engage and enlarge the scope of others’ interest and participation. A manager generally adds value by translating the vision into relatively concrete, measurable terms that enable an enterprise to quantify and better organize the work of its members.

A leader must have a strong grasp of management to assure that visions translate into results, or, as Roosevelt might have put it in speaking of politics, so that prophecies can be turned into policies. TR was a notably pragmatic leader. In the same vein as his oft-quoted statement, “Keep your eyes on the stars, but remember to keep your feet on the ground,” the poetry of Roosevelt’s leadership was brought “down to earth”—made effective—by his attention to the prose of management. TR was, in Peter Drucker’s definition, an “executive,” one who is “responsible for a contribution that materially affects the capacity of the organization to perform and to obtain results.”


“Theodore Roosevelt, Executive” by James M. Strock originally appeared in the Theodore Roosevelt Association Journal, Volume XXVIII, Number 3, Summer 2007, pages 10-24, and is reissued here with the editor’s permission.  The Theodore Roosevelt Association Journal is a quarterly publication sent to all members of the Theodore Roosevelt Association. Membership in the TRA is open to anyone interested in the life, accomplishments, ideals, and contemporary relevance of Theodore Roosevelt, the twenty-sixth President of the United States.  A TRA membership application can be obtained by clicking on the membership application.


One might identify 20 key elements in Roosevelt’s approach to executive leadership. The remainder of this essay focuses on these elements.

Theodore Roosevelt(1) Begin hard and fast. TR made his presence felt from the moment he took command. Newly appointed to the sleepy U.S. Civil Service Commission, “he became a blur of high-speed activity.” His contemporaries, journalists Jacob Riis and Lincoln Steffens, noted his immediate, purposeful taking of the reins of the New York City Police Board. At the Navy Department, defying admonitions about President William McKinley’s anxious concern that he might act impetuously, TR burst off the block to a sprinting start. When the circumstances surrounding the formation of the Rough Riders necessitated that he move fast, he was comfortable in the task before him. Even in the unavoidably awkward aftermath of his inauguration following McKinley’s assassination in September 1901, Roosevelt unselfconsciously asserted his new management prerogatives. While limited by prudence from initiating too conspicuous a break from his predecessor’s style or policies, within days of taking office he intervened in personnel issues that customarily were not handled (or at least not directly handled) by the President himself.

Taking the reins rapidly sent several important management signals. Other members of the organization were served notice that the new policies represented and advocated by their new leadership would begin posthaste. The broad interest displayed by the new leader also would alert lower-level managers to consider whether decisions that might have been handled previously at their level henceforth might need to be elevated; either way, greater attention to the views from the top would be expected. Implicit in this approach was Roosevelt’s recognition that the effective power of new management is often greatest at the point of initial transition, when prospective opposing interests may not have coalesced in an environment of uncertainty.

(2) Seize—and hold—the initiative. According to one of his close associates, Roosevelt’s “motto” was “action, action and still more action.” Another quoted TR adage: “Life is action.” Roosevelt in repose is not an image readily evoked. In part this may have reflected, as Elihu Root suggested, his temperament; surely also it arose from Roosevelt’s “philosophy” of living “the strenuous life.”

Whatever its source, Roosevelt’s bias for action, combined with the rapidity with which he dispatched tasks in which he was engaged, was a notable part of his approach to leadership and management. Some people, in his time and our own, conclude that the speed of his decisions suggests precipitate or impetuous action. In fact, as his perceptive contemporary Lewis Einstein observed, Roosevelt’s actions generally followed systematic, methodical forethought:

Roosevelt was himself far more cautious than is commonly believed. His methods of inquiry before taking a decision were conducted with the utmost prudence. He was artist enough to hide this aspect of his skill, and to serve his dishes without any indication of their ingredients or of the care he had generally taken in their preparation. His method was that of the military commander who conceals his reserves until ready to hurl them at the foe. Roosevelt’s system of attack when it came into the open was so frontal that men forgot the wariness of his approach and the craft with which he prepared his onslaught.

TR’s study of military history and affairs underscored the value of taking the initiative, thereby obtaining the advantages of the first mover, of setting the terms of engagement, of preparation sharpened by focus on the end in view. His approach also maintained the vigor of the organizations he led, not allowing them to fall into the traps that await those who “rest on their laurels” (as he warned the decamping Rough Riders), or to avoid change and learn only from disaster. Roosevelt’s relentless maintaining of the initiative also enabled him to unite and obtain high performance from his teams. In forcing his adversaries to the battlegrounds of his choosing, he may have created an aura of power greater than objective circumstances would have indicated before his apparently sudden action reconfigured the scene.

Theodore Roosevelt, rough rider(3) Continually communicate your vision to members of the organization. A vital element of Roosevelt’s success as an executive was his constant communication of his vision. His uncanny ability to identify with his audiences included the members of the organizations he led. In each of his management positions he enunciated a visionary action agenda. The Rough Riders, for example, were given to understand that they were fighting not only for American honor against Spanish perfidy, but for a new American role in the world. TR imparted a sense of historic importance, of destiny, to a group of amateur soldiers who would constitute, at the turn of a new century, the first regiment of American troops representing all sections of a nation against a foreign foe since the Civil War of the previous generation.

As the new President, Roosevelt presented his vision for the government he would lead in a remarkably detailed presidential message released on December 3, 1901. The signature planks of what would come to be known as the “Square Deal” could be found in this document, which TR transformed from a routine compilation of executive agency reportage and budgetary demands into a working paper unmistakably bearing his own stamp.

As significant and elevated as his verbal and written communications were—he was a recognized master of both—there is little question that the words were secondary against the background of his potent example. Convinced that a restoration of what he called the “national character”was the paramount challenge of his time, TR personified his vision. This enabled him to harness the power of his own richly experienced life. Roosevelt strove to apply the standards of heroes from history to his understanding of his own time and place, and to incorporate them into the example he would offer. Writer Julian Street, who spent considerable time with TR in 1915, was undoubtedly correct in emphasizing the Rough Rider’s observation: “If I have anything at all resembling genius, it is in the gift for leadership. For instance, if we have a war, you’ll see that young fighting officers of the army want to be in my command. . . . To tell the truth, I like to believe that, by what I have accomplished without great gifts, I may be a source of encouragement to American boys.”

Roosevelt’s project of transforming himself and his life narrative into a heroic mold required courage that could be recognized and understood by others who shared his underlying values. This imparted a moral authority—and an ability to lift the morale of the teams he led—that was striking in an era when then-“traditional” values were under challenge.

Members of TR’s organizations might well ask themselves in any given circumstance, “How would Roosevelt handle this situation?” When he served as president of the New York City Police Board, he applied conspicuous vigor to his daily work, attempting to impose clear delineations of legality and morality, long absent from the loosely corrupt department he inherited. Backing up his words with his deeds, methodically crafting his own life story to emphasize the importance of his own development of what he called “character,” Roosevelt served as an educator in the original sense, leading people toward his vision. Uniting his vision with his self-presentation, he turned his every action into a broader communication of his vision. In so doing he also displayed how others, individually, could make a difference in achieving that vision.

(4) Make the welfare of your team your foremost responsibility. The keystone of TR’s success as a team leader was that he consistently and conspicuously placed the welfare of the group ahead of his own. Perhaps this is best encapsulated in a single statistic. As Roosevelt emphasized inThe Rough Riders“In my regiment, as in the whole cavalry division, the proportion of loss in killed and wounded was considerably greater among the officers than among the troopers, and this was exactly as it should be.”

As a team leader in the Spanish-American War, TR reliably took the perspective of the troops for whom he was responsible. He declined the offer of the top command of a regiment in favor of a more experienced officer. He butted heads with the bureaucracy to ensure that his troops would be outfitted with summer clothing. He twisted arms to make certain they were equipped with smokeless rather than outdated black-powder rifles. He demanded decent food for them and was prepared to purchase it himself if necessary. He paid out of his own pocket to move the regiment to its port of embarkation for Cuba. As enemy batteries showered death on the Rough Riders, TR at once protected and inspired his team, remaining on horseback while they were on foot. After the close of the hostilities—likely at the cost of the Medal of Honor he coveted—he signed a public letter to the military brass, demanding immediate action to protect the troops from rampant malarial fever (at one point he reported to his sister Corinne that of approximately 400 men in his camp, 123 were in doctors’ care, with the rest of the 600 he started with either dead or in rear hospitals). When his regiment returned to Long Island, Roosevelt declined the offer that would have allowed him—but not those under his command—to leave camp and visit his nearby home and family.

Theodore Roosevelt teddy bearTR asserted: “The best work can be got out of the men only if the officers endure the same hardships and face the same risks.” Throughout his life—beginning in the Badlands—Roosevelt lived by the code he expressed shortly before his death: “No man has a right to ask or accept any service unless under changed conditions he would feel that he could keep his entire self-respect while rendering it.” With few limitations on what he would give of himself, TR faced few limitations on what he could ask of others.

(5) Hire people more talented than yourself. Roosevelt sought talented individuals for his teams, when possible recruiting individuals of recognized, pre-existing stature. He understood that a chief executive has no more important task than attracting and retaining the ablest possible group.

In The Effective ExecutivePeter Drucker explains: “No executive has ever suffered because his subordinates were strong and effective. There is no prouder boast, but also no better prescription, for executive effectiveness than the words Andrew Carnegie, the father of the U.S. steel industry, chose for his own tombstone: ‘Here lies a man who knew how to bring into his service men better than he was himself.’” Though each member of the team may have been, in Drucker’s words, “a ‘better man’ in one specific area and for one specific job, . . . Carnegie . . . was the effective executive among them.”

[Click here for the story of the Teddy Bear]

For the biggest jobs—in terms of priority to the enterprise and demands on the occupants—Roosevelt would brook no compromise on quality. The construction of the Panama Canal called for “the biggest man we can get.” For the U.S. Supreme Court—of particular importance to Roosevelt, given the high court’s propensity to strike down assertions of legislative and executive power at the turn of the twentieth century—his insistence on excellence yielded Oliver Wendell Holmes, Jr.

First as secretary of war and later as secretary of state, Elihu Root, the legendary Wall Street lawyer, served Roosevelt and the nation with distinction. He advised the president on matters large and small. TR acknowledged that Root was well qualified for the chief executive role. Had the politics of the time allowed, he likely would have sought to install Root as his successor. Though their paths diverged when Roosevelt bolted the Republican Party in 1912, Root’s career was one of historic accomplishment, including a Nobel Peace Prize.

William Howard Taft—with whom Roosevelt later split in a spectacular fashion—served estimably in the Philippines and in the cabinet; he eventually became the only person to have served as President and chief justice of the United States. Gifford Pinchot—one of the founders of the modern conservation movement and a future governor of Pennsylvania—was a protégé of TR and a dynamic public administrator.

Talented people attract talented people. Roosevelt was proud of the considered judgment of one of the most respected observers of the era: “At the end of my administration Mr. [James] Bryce, the British Ambassador [author of The American Commonwealth] told me that in a long life, during which he had studied intimately the government of many different countries, he had never in any country seen a more eager, high-minded, and efficient set of public servants, men more useful and creditable to their country, than the men then doing the work of the American Government in Washington and in the field.”

Members of his team continued to serve the nation in succeeding decades, some through the presidencies of Franklin Roosevelt and his successor, Harry Truman. Having been credentialed by TR, such individuals would be recognized as experts in their various fields and veterans of an extraordinary group. They were a living legacy, extending Theodore Roosevelt’s influence into the future.

Theodore Roosevelt and John Muir(6) Ceaselessly search for new talent. In each executive position he held, TR tirelessly sought to identify talented individuals and reward outstanding performance. Perhaps from his own experience in subordinate positions, he was dubious of promotion based on seniority rather than results. At the Navy Department, he advocated changes along those lines. Acknowledging that subjective factors in judging performance created a risk of rewarding “courtier” qualities, he concluded that the exigencies of war would incline toward a down-to-earth emphasis on tangible, measurable achievements.

In the presidency, Roosevelt’s cultivation of talent prompted him to rummage around in distant organizational levels under the direct authority of his subordinates. When he personally intervened to attract a particularly able assistant secretary of state, he coordinated his efforts with the secretary’s, made clear his goal was to fortify the secretary’s office, and implicitly reminded all involved that they were part of the larger Roosevelt team.

(7) Recognize strong performers. Writing to his son Quentin in 1914, TR recalled his own father’s concern about passing along too many compliments, “because he did not think a sugar diet was good for me.” It might be said, though, that Roosevelt had no compunction about providing a sugar diet for productive members of groups he led.

Elihu Root (before their falling out in 1912) “was the man of my cabinet, the man on whom I most relied, to whom I owed most, the greatest Secretary of State we have ever had, as great a cabinet officer as we have ever had, save Alexander Hamilton alone.” Shortly after the 1912 election defeat, deploying flattery that would have alarmed many across America and around the world, TR addressed Gifford Pinchot, “O Mr. Secretary of State that-was-to-have-been!” Some of his fulsome praise—at times rather promiscuously bestowed on unexpected, dubious beneficiaries—caused observers to cringe. His custom, consistent with focusing on the best in each person, was in line with Goethe’s dictum: “Treat people as if they were what they ought to be and you will help them become what they are capable of becoming.”

Throughout his executive career, Roosevelt strove to lift morale and reinforce virtue through timely, public recognition of accomplishments. Doubtless with an eye toward Lincoln, who established the Medal of Honor during the Civil War, TR initiated the custom of White House presentations of the nation’s highest military decoration. Critics chortled about the Panama Canal medallions prominently featuring TR’s likeness and dramatically inscribed: “The Land Divided, The World United.” Roosevelt sought to create among the Panama Canal workers an esprit de corps comparable to that of the dwindling band of aging Union Army veterans who gathered together annually to commemorate their service during the great days of 1861 to 1865, poignant and resplendent in their dress uniforms and glittering medals.

Roosevelt’s sword cut a line in the sand between recognition that he conferred on members of his teams and that which they assumed for themselves. When Secretary of State John Hay died in 1905, TR expressed boundless admiration for “a man whose position was literally unique.” He vociferously asserted, with respect to Hay and others, “I do not care a rap as to who gets the credit for the work, provided the work is done.” Yet when Hay’s posthumous papers appeared to claim credit for accomplishments the President viewed as his own, TR wrote a detailed account to Henry Cabot Lodge, declaring that Hay “accomplished little. . . . His usefulness to me was almost exclusively the usefulness of a fine figurehead.” Perhaps feeling the hand of history on his shoulder, he wrote somewhat similarly about Hay’s successor Root in a letter to Andrew Carnegie near the close of his presidency. After enumerating the greatest foreign policy achievements of his administration as those he had “personally” handled, TR saluted Root for his primary role in the remainder.

Depending on one’s viewpoint and temperament, this aspect of Roosevelt can be disappointing or amusing. His claims of personal credit were generally accurate and sufficiently infrequent so as not to drain the force of his customarily generous recognition of his subordinates’ contributions.

(8) Acknowledge and forgive acceptable mistakes—including your own. TR recognized that mistakes were inevitable whenever a leader or a group took action. The improvisation and creativity sparked by expansive delegation inevitably occasion missteps.

Roosevelt could be forthright in acknowledging his own mistakes to his team. Troops in his Spanish-American War regiment were touched by his candor in detailing his misinterpretations of the training manual. They surely surmised that a leader marked by such a high degree of self-confidence might display a correspondingly understanding attitude toward others.

Where a team member’s mistake did not involve an essential matter, TR could be forgiving. In one memorable incident, Roosevelt unilaterally freed a Rough Rider court-martialed for violation of camp regulations. According to Jacob Riis, the soldier was in “agony” over not being able to join the fight in Cuba. TR, unrestrained by notions of due process incompatible with his personal judgment, relented: “All right, you deserve to be shot as much as anybody. You shall go.”

In TR’s subsequent campaign for governor of New York, opposition papers gleefully circulated one Rough Rider’s inadvertently damning praise: “He led us up San Juan Hill like sheep to the slaughter and so he will lead you!” Roosevelt had the good sense to share in the general merriment.

TR could be less forgiving of mistakes made by subordinates acting in his name, especially when he was directly implicated and had not approved the action in advance. Journalist O. K. Davis recounted an embarrassing incident in which an ungrammatical diplomatic message was dispatched by a State Department functionary over President Roosevelt’s signature. Widespread criticism and ridicule ensued. TR summoned reporters, telling them “off the record” what had occurred, identifying the clerk who was responsible. In a single transaction Roosevelt protected his reputation, avoided disclosing to the other nation that the cable was not actually his handiwork, and accurately transferred responsibility to the offending civil servant without resorting to unbecoming public censure.

TR understood that an organizational culture that was unforgiving of mistakes could become dangerously inflexible in a time of accelerated change. As he wrote of the navy, “If there is one thing more than any other which our bureau chiefs and technical experts need to learn it is that they must never for a moment consider the question of acknowledgment of error in the past as a factor in doing what is best possible in the present. . . . To refuse to accept any change until its advantages have been demonstrated by actual experience means that we must always be behind the times.”

(9) Overlook “minor differences.” Roosevelt recognized that he could effect more change on more fronts if he did not allow himself to be distracted by what he called “minor differences.” As he wrote to Gifford Pinchot about the Progressive Party after the 1912 election, “almost every man of any prominence in this movement has been both a burden and an asset.”

It likely never crossed Pinchot’s mind that Roosevelt might be describing him. There is no question he was an invaluable assistant to TR: He was loyal, bright, visionary, determined, and monomaniacally dedicated to his work. He was also abrasive, self-righteous, shortsighted, eccentric, and egocentric. Roosevelt once wrote, “Gifford Pinchot is a dear, but he is a fanatic, with an element of hardness and narrowness in his temperament, and an extremist.” Following the fateful blow of the unexpected death of his young fiancee many years earlier, Pinchot remained a bachelor until late middle age—a status for which Roosevelt, a strident advocate of large families, had scant regard. He could be infuriatingly demanding of TR’s time on trivial matters—as when he caused the President of the United States to decide whether Pinchot would be allowed to sign his (Pinchot’s) entire name, or only his initials, on bureaucratic documents. Patiently placing such annoyances in perspective, Roosevelt obtained prodigious performance from his mercurial associate. TR even found value in Pinchot’s disagreeable side, utilizing him as a “lightning rod” for controversial environmental policies.

Roosevelt extended his effectiveness by working in harness with individuals with whom he agreed on a given project, even though they shared little else in common. To the chagrin of purists, he worked well with numerous “machine” politicians on issues of mutual interest. The key was TR’s unswerving focus on the “essential” in any given situation.

(10) Ruthlessly replace individuals who do not meet the standards of the enterprise. New talent—new people with skills required for new challenges, new skills developed in existing team members—is impeded whenever a position is occupied by someone less able to advance the enterprise. Just as a forest renews itself through the removal of old growth, so an organization must continuously be shorn of less productive elements.

In a time of unprecedented change, Roosevelt did not hesitate to cashier those who could not keep pace. In 1908 he wrote to the expendable head of the Government Printing Office: “I do not believe you are able to manage this particular office—one of particular difficulty and needing a peculiar combination of traits in the man who is to do the work successfully. If the opportunity comes I shall be glad to place you in some office commensurate with your abilities.”

TR held relevant questions of character to be non-negotiable. He frequently told of a capable ranch hand whom he found stealing others’ cattle and marking them with the Roosevelt brand. TR fired him forthwith: “If you will steal for me, you will steal from me.”

When in command, Roosevelt viewed insubordination as grounds for summary action. To be sure, this was a shortcoming he was peculiarly qualified to judge. In a controversial series of incidents arising early in his presidency, TR rebuked a popular hero of the Civil War and Indian conflicts, General Nelson Miles. Roosevelt backed up Secretary of War Root in establishing a record of Miles’s alleged deceit. TR stipulated that the old general “ought only be employed when we are certain that whatever talents he may possess will be used under conditions which make his own interests and the interests of the country identical.”

Roosevelt’s method of firing was situation-specific. The key was the good of the enterprise. When a top-level individual could be pushed aside quietly, transferred to another position better suited to his skills, TR might oblige. If a broader message was necessitated by circumstances, he would not hesitate to fire an employee personally and publicly.

Theodore Roosevelt(11) Develop leaders. A leader should develop leaders, not merely direct followers. John Maxwell calls it the “Law of Explosive Growth.” When a chief executive methodically cultivates the leadership abilities of his subordinates, he exponentially enhances the potential of the organization. This requires a significant investment of time and resources by the chief executive. In subordinate roles TR had been frustrated by a lack of authority to act, unclear accountability, an absence of high-level support, and an inability to communicate vital information up the chain of command. Becoming the executive he had wished for, he empowered—indeed required—his subordinates to lead. This was the inevitable corollary of his theory of delegation. As he stated in a letter to a subordinate in 1906: “I shall give you an entirely free hand . . . because I hold you to an absolute responsibility for the conduct of affairs.”

(12) Demonstrate faith in your team by delegation of authority.Roosevelt’s selection of the “very strong and positive men under him” enabled him to delegate authority expansively. He wrote in 1899, “[The leader] has the reins always and can shape the policy as he wishes it, and it is for his interest to have each department run by a man who will carry out his general policy, but will be given large liberty as to the methods of carrying it out.” Some years later, Roosevelt spelled out his approach:

If I want a man under me to do a job, I will give him the power to do it, and I will say: “I want you to do that piece of work.” Now if he says: “How am I to do it?” I will say: “I will take another man. I will take someone else to do it.” If I am trusted to do a job, I want the power given to me and then I will be held accountable for it. But give me the chance to make or mar that job myself.

Roosevelt’s approach was vividly demonstrated in his historic, successful effort to construct the Panama Canal. The strategic value of a canal connecting the Atlantic and Pacific Oceans had long been recognized, but numerous attempts to realize it had foundered. TR faced extraordinary challenges. Once the necessary foreign policy hurdles had been cleared, the President confronted what one historian aptly concluded was “as difficult a task as an administrator can be asked to do”:

He had to create and staff an entirely new administrative organization which had to perform an unprecedented job. This organization had to be responsible for digging, dredging, and constructing locks and dams on a huge scale. It had to provide for the regular and systematic flow of supplies and materials from the United States over 2,000 miles of water to the Isthmus. It had to recruit a laboring force of skilled and unskilled labor, to transport the force to Panama, and then to house and feed these men. The care of their health required a large medical staff to fight yellow fever and other tropical diseases. Furthermore, this administrative unit had to govern the Canal Zone and handle relations between the Americans and the Panamanians. Finally, the organization had to operate under pressures from Congress, labor officials, the press, and the American public.

TR understood that every foreseeable threat looming over this vast public works project would be exacerbated with the passage of time. It would not be completed during his term of office under any scenario (it was actually finished in 1914, during the Wilson administration). Seizing the initiative, TR would leave his policy too far in gestation to be reversed responsibly by others.

Through the many twists and turns of this unprecedented undertaking, Roosevelt was consistent in his method for getting the best from his team: He defined the mission; he hired the best available personnel; he delegated authority from his office and centralized it in the hands of an accountable subordinate; he backed and protected the accountable subordinate’s team with every appropriate tool at his disposal.

Administrative problems initially placed the entire enterprise at risk. Senior members of Congress, professing concern over Roosevelt’s full-throated assertions of executive power, imposed a seven-person Isthmian Canal Commission. The commission, based in Washington, was hobbled by an unclear mandate and a structure incompatible with accountability. The result resembled what Roosevelt found at the New York City Police Board years earlier: “a complete divorce of power and responsibility, and it was exceedingly difficult either to do anything, or to place anywhere the responsibility for not doing it.”

TR asked Congress to restructure the commission and to authorize him to appoint an administrative staff to supervise the work in Panama. Slouching supinely into the passive-aggressive posture routinely assumed by legislative bodies, Congress indulged in vehement discussion—and took no action. Undeterred by the failure of his attempt to observe legal niceties, Roosevelt drove into the void with an executive order channeling administrative authority into three departments to be directed by presidential appointees. Ultimately Roosevelt moved further, placing power in the hands of a single individual, Colonel George W. Goethals. The commission survived as a shell, with Goethals as chairman and Joseph Bucklin Bishop, a protégé of TR, serving as staff director in charge of day-to-day activities.

In Goethals, Roosevelt secured the accountability he believed essential for achieving results. As he had written in the context of municipal reform, “What we must have is some one man to hold to a definite responsibility.” He took the same approach in other important areas of his administration. For example, he reorganized the Forest Service to affix “undivided responsibility” for paramount environmental priorities.

Roosevelt’s approach to delegation—backed by his practice of expressing and enforcing high ethical standards—afforded him distance from activities that were necessary but perilous to the overall mission of the enterprise. George Cortelyou, whose highly productive fundraising efforts for the 1904 presidential election campaign have never been fully documented, met TR’s high expectations while apparently not burdening him with unnecessary details. John King, who played a similar role in later years, veered off the road of legality only after Roosevelt’s death.

Theodore Roosevelt police commissioner(13) Delegation, though extensive, should be bounded by clear standards. Roosevelt tended to delegate most extensively in the most important projects, the Panama Canal being the most important of all. He distinguished between the setting of policy— which requires the decision of the chief executive—and implementation, which he largely left to the discretion of the accountable subordinates. Roosevelt negotiated agreements for the accomplishment of specific actions by specific dates, defining the “success” by which he would evaluate and enforce performance.

Roosevelt provided continuing feedback. His first secretary of the interior, inherited from McKinley, had difficulty adjusting to the torrent of expectations aroused by TR’s pioneering commitment to environmental protection. In an effort to give him a stable toehold, Roosevelt dispatched detailed reactions, suggestions, and instructions. He gradually took the department into managerial receivership. When the secretary was ultimately replaced, the reasons were clear to all concerned. The accumulated letters and memoranda transmitting feedback would be available as an invaluable training and acculturation manual for his successor.

(14) Fortify delegation with selective intervention. TR routinely intervened in the operations of well-run organizations within his responsibility. At first glance this practice might appear contradictory to his commitment to delegation, but generally it was not.

Roosevelt was renowned for communicating directly with subordinates far down the chain of command—sometimes implementing their recommendations against the expressed wishes of their supervisors. It was not a surprise when he accepted the counsel of seamen, overruling naval authorities on the types of vessels allowed to become part of the Great White Fleet. Obviously, were it taken too far, this approach could undermine the authority of TR’s top appointees. In the case of the navy, President Roosevelt found it difficult to resist the temptation to be what he would characterize, in other contexts, as a “meddlesome Mattie.” This was surely a factor in the high turnover in the position of navy secretary during his administration.

In some cases TR’s hand reached deep into the machinery of his organizations, directly and visibly safeguarding the welfare and raising the morale of his larger team. President Roosevelt constantly intervened in military affairs, ranging from training curricula to the color of shirts worn by troops; from the dimensions of cavalry spurs to reversing a War Department decision affording more respectful notification to the families of officers killed in battle than to those of enlisted men. When such interventions were immediately recognizable as being within his vision and priorities, strains on the violated chain of command could be minimized. Roosevelt’s proclivity in this regard encouraged lower-level employees—often facing realities entirely different from what was reported to decision makers—to share information with the chief executive without fear of penalty.

President Roosevelt publicly overturned actions by high-level subordinates that may have been necessary or justified from their perspective but appeared counterproductive from the singular vantage point of the chief executive. He reversed rulings of his administration restricting the use of popular food additives—including saccharine, on which the increasingly imposing chief executive personally relied. He cited fears of a backlash “upsetting the whole pure food law” that he had worked assiduously to achieve. Perhaps he was also concerned about other, apparently unrelated, priorities being disordered by the timing or tone or substance of such errant decisions. In the aftermath of the saccharine intervention, TR prepared correspondence explaining his actions and reiterating his support for the chastened decision maker, whom he considered to be useful in some respects.

Even in the White House, TR interjected himself in matters that at first glance might appear picayune or tending toward “micro management.” In fact, they generally related to issues of great symbolic importance, communicating values and priorities inside and outside his administration. Almost immediately upon taking office as President, he ordered the Board of Commissioners of Washington, D.C., to halt air pollution from nearby public and private facilities—or, if they did not have requisite authority, to draft enabling legislation. On a later occasion he directed the secretary of war to ensure that African-American regiments have African-American bandmasters as soon as possible. In his capacity as “First Reader,” he instructed the Public Printer to put a stop to “rough edges and gilt tops” and other unnecessarily expensive covers for government publications, in favor of “the plainest and simplest kind of bindings.”

Roosevelt’s approach to delegation was made effective by his wide-ranging interests, insatiable curiosity, technical competence, capacity to obtain information from outside the usual organizational channels, and methodical follow-up to prior directives. Every member of his administration, from cabinet members to assistant secretaries to clerks, labored with the sobering awareness that TR’s energy and intellect might—without warning—furiously bore into an issue or an organization, questioning practices, personnel, arrangements, and accomplishments. Those to whom he delegated significant authority were energized—and disciplined—by this ever-present possibility.

(15) Manage by wandering around. Roosevelt perceived the value of what Tom Peters later popularized as “managing by wandering around.” Emerging from behind the desk of authority and moving throughout his organization, he could learn far more than could be conveyed within the four corners of formal memoranda.

As a state legislator and again as governor, he visited tenements in New York City, uncovering a reality far more oppressive than depicted in faraway jurists’ elegant dicta about the sanctity of freedom of contract. As a police commissioner he roamed the mean streets, often in disguise and late in the evening, rousting sleepy and corrupt officers and bolstering the resolve of those doing the right thing. At the Navy Department TR toured ships and shipyards rather than relying on the lifeless, sanitized words of routine reports. In November 1906, as President, TR went to Panama to inspect personally progress on the construction of the Panama Canal (incidentally making him the first President to leave the continental United States while in office). As he wrote his son Kermit, “I went over everything that I could possibly go over in the time at my disposal.”

As President, he ventured to Yosemite with preservationist John Muir, examining the giant sequoias, whose “majestic trunks, beautiful in color and in symmetry, rose round us like the pillars of a mightier cathedral than ever was conceived even by the fervor of the Middle Ages.” TR’s personal observations enabled him to distinguish those trees he believed could be harvested from those that should be preserved for posterity.

In 1907President Roosevelt visited the American naval forces that would become known as the Great White Fleet, preparing to tour the world in an unprecedented, peaceful show of force. The top brass recommended that destroyers not be included in the flotilla. After meeting with several lieutenants TR was convinced that such vessels could make the cruise. He recognized the serious labor-relations problem lurking underneath the issue; enlisted men were threatening to leave the service unless their destroyers were included. “I accept[ed] the word of the men who were to do the job, . . . and within half an hour I sent out the order for the flotilla to be got ready.” In a similar vein, after having inspected and gone underwater in a prototype submarine, the PlungerTR ordered hazardous-duty pay for its crew.

Through his physical presence TR could remind his team that he was not asking them to do anything more than he would offer of himself; he could inspire them by reiterating the connection between their work as individuals and the broader enterprise; and he could personify their shared endeavor.

(16) Back up your team. Having affixed accountability, Roosevelt would unfailingly back his team. This was particularly important with respect to the Panama Canal because of the many obstacles confronting the novel, gargantuan enterprise. He regularly asked Goethals and other top officials to let him know what they needed—a presidential statement here, legislation there, executive orders everywhere—and he would do whatever he could. If the Congress was restive and harassing—as when spitefully cutting the salaries of top officials for the project—he would swing into action. When a lawyer employed by the commission questioned the legality of a plan to build recreational facilities for workers, the president instructed the top staff: “You go back and tell that man to keep his mouth shut. He is not there to find objections. . . . I want to build the canal; I do not want to be told how not to do it, but how to do it. . . . I’ll take the responsibility.”

When a cabinet member was under fire following credible accusations of wrongdoing arising from his prior employment in the railroad industry, Roosevelt examined the facts and determined that his man was morally upright. Unfortunately, the facts were difficult to explain concisely; the secretary’s actions were foreseeably vulnerable to distortion and as such would not have been condoned had they occurred in the Roosevelt administration. Nonetheless, TR would not allow his associate to be run out of office on that basis.

Resolutely backing up staff reinforces accountability, focuses the chief executive on the areas where he can best add value, protects the chief executive’s time and tactical flexibility by discouraging appeals of lower-level decisions, and promotes loyalty.

(17) Create an “inner circle” of leadership. This essay has used the term “team” broadly. For example, Roosevelt as President might be viewed as leading several teams, including his cabinet, his administration, the national government, and the nation as a whole.

Apart from those groups, Roosevelt relied extensively on what John Maxwell calls an “Inner Circle” of leadership. Most notable was an informal set during the White House years known as the “Tennis Cabinet.” It included some of his cabinet members, some sub-cabinet officials, diplomats from foreign nations, and sundry friends and family. The Tennis Cabinet bridged TR’s work and play, enabling him to cross-fertilize information and perspectives that otherwise would not have come together.

The President regularly visited the home of Secretary of State Hay after Sunday church services. Hay, and sometimes others such as Root and Taft, could use this setting to educate and inform TR in ways not possible in twice-weekly cabinet meetings. In addition to his responsibilities as secretary of state, Hay was a living link to Lincoln and the Civil War generation, to whom Roosevelt looked for inspiration and perspective. TR relied on the political and personal skills of his sister Bamie, whose home he frequented and used for many important meetings, first in New York and later in Washington (where her home was sometimes referred to as the “Little White House”). He unflaggingly maintained a lively correspondence with accomplished individuals close to home and in foreign lands.

TR’s inner circle helped him maintain high standards. This is important for chief executives, whose ascendancy is often accompanied by a muting of longtime sources of feedback. Undercurrents of benign competition ran through the Tennis Cabinet, sometimes reaching Roosevelt. This likely kept TR at his best, just as an athlete may achieve peak performance while training with or competing against other accomplished athletes.

(18) Continually convey loyalty and gratitude to your team—even after it has been disbanded or leadership has been transferred.Roosevelt’s heartfelt loyalty to his teams persisted for the remainder of his life. Understandably, given their shared experience, his relationship with the Rough Riders was a thing apart. Even as President TR would interrupt virtually anything he was doing to greet delightedly a comrade from the Cuban campaign. Almost no request from them could be too great.

A few erstwhile associates managed to explore his loyalty’s outer limits. In correspondence in early 1901 Vice President Roosevelt related a recent request from a Rough Rider on trial for murder:

“Dear Colonel: I write you because I am in trouble. I have shot a lady in the eye. But I did not mean to shoot that lady. It was all an accident, for I was shooting at my wife.” . . . Evidently he felt that the explanation was sufficient from one man of the world to another! However, I wrote him back that I drew the line at shooting at ladies and could not interfere.

TR’s continuing concern won the lasting devotion of his past colleagues. A diverse group of individuals, representing each part of his varied career, they constituted a network that would assist him in various, unforeseeable ways in his future endeavors.

Roosevelt was mindful of the gratitude he owed others for his opportunities to serve and for the success of their shared enterprises. A touching reminder is in a 1913 letter to his distant cousin Franklin Roosevelt, married to his niece Eleanor. President Wilson had recently appointed FDR assistant secretary of the navy. After congratulating the rising star and recounting the similarities in their early careers, TR gently reminded the ambitious younger man to do whatever he could to brighten the drab lives of naval wives: “Everything that can properly be done to make things pleasant for them should be done. When I see you and Eleanor I will speak to you more at length about this.”

(19) Serve as a continual agent of change. Leadership is about change. A leader—in whatever position one chooses to lead from—embraces a vision and seeks to move others toward that vision. As other individuals accept and join in the pursuit of the vision, by definition they are headed toward a new goal (even if they see it, at first, as simply heading toward an existing goal at a faster pace), representing change for themselves, the group of which they are a part, and various others affected by their movement. As is often said, a leader is one who moves people to a place they would not have otherwise gone.

In order to be more than a prophet, to be an “executive” who extends his or her leadership through management, one must reconcile what many individuals hold to be competing or contradictory tendencies. One must ground a vision in quantifiable accountability measures that mark, monitor, and institutionalize change. One must constantly be aware of the unpredictable, often uncontrollable, outside forces—while routinizing procedures for subordinates who seek stability and an apparently assured connection between their efforts and the success of the enterprise.

Roosevelt’s success as an executive was rooted in his capacity to welcome and embrace change. This capacity reflected his lifelong project of transforming himself into a leader in the heroic mold he admired from history.

TR’s words to his British correspondent G. O. Trevelyan reflect his dynamic view of life and leadership: “Life is a long campaign where every victory merely leaves the ground free for another battle.” Roosevelt’s ongoing campaign to improve himself, to make himself into a leader worthy of those he would serve, was a cornerstone of his ability to thrive as an executive.

(20) Become the author of yourself. The most effective executives share certain qualities, as outlined in this essay. Ultimately, though, as in any field, the very best are also unique in their own time and place. Oscar Wilde famously observed that “most people are other people,” adding, “Their thoughts are someone else’s opinions, their lives a mimicry, their passions a quotation.” Surely Joseph Bucklin Bishop was right to emphasize, quoting Emerson, in describing Roosevelt: “He is great who reminds us of no others.”

Warren Bennis argues that self-transformation, or “self-invention,” is necessary to achieving uniqueness: “People who cannot invent and reinvent themselves must be content with borrowed postures, secondhand ideas, fitting in instead of standing out. Inventing oneself is the opposite of accepting the roles we were brought up to play.” Bennis adds: “To be authentic is literally to be your own author (the words derive from the same Greek root), to discover your native energies and desires, and then to find your own way of acting on them.”

The change implicit in the continuing self-transformation of a leader does not, of course, move entirely from the inside outward. A leader’s drive to serve others means that continuing change is unavoidable, since the needs of those one would serve can never be static.

Roosevelt believed that service was the essence not only of good leadership in any capacity, but also of happiness in life: “In the long run no man or woman can really be happy unless he or she is doing service. Happiness springing exclusively from some other cause crumbles in your hands, amounts to nothing.” TR endeavored to apply the same notions of service in all parts of his life, resulting in a unified personality, an unmistakableintegrity. With his own personality not divided against itself, Roosevelt’s oft-noted boyish nature was, in part, a reflection of his transparent, hard-won simplicity, which channeled the full force of his personality, without diversion, into his leadership.

Speaking of home and community life, TR said, “The simple life is normally the healthy life.” For all his intellectual curiosity and political subtlety, he fairly may be seen as one who strove mightily to make his life conform to the conventional moral tenets he espoused robustly. The terms identified with his pragmatic approach—“realizable ideals,” “applied Christianity”—proclaim the tension inherent in seeking to advance morality in the workaday world.

* * * * * * * * * *

Perhaps Roosevelt’s disproportionate dismissal of those who declined to engage the issues in the rough neighborhoods where the fights mattered—“the timid good,” “the professional impracticables,” those of “cloistered virtue” and so on—inadvertently disclosed his own discomfort with the necessary compromises. Yet it was that very struggle, likely sensed by others to a greater extent than he recognized, that rendered Roosevelt’s leadership uniquely compelling to many of those who were devoted to him in life—and to many more a century later.

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