James Strock on Theodore Roosevelt and Other Great Leaders: Part 2 of an interview by Bob Morris

James Strock is a best-selling author and speaker on leadership. His passion for the practice of leadership spans four decades. He’s an independent entrepreneur and reformer in business, government, and politics. He is the founder of the Serve to Lead Group. Strock also served as the founding secretary for environmental protection for the State of California; as the chief law enforcement officer of the USEPA; general counsel of the US Office of Personnel Management; and special counsel to the US Senate Environment and Public Works Committee. His books include Serve to Lead, Theodore Roosevelt on Leadership, Reagan on Leadership, and Disrupt Politics. Strock is a member of the Council on Foreign Relations and served to captain in the USAR-JAGC. He divides his time between Arizona and California.

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In your opinion, what what would Theodore Roosevelt  do — and how would he do it — to increase the percentage of actively and productively engaged people in any organization after he was hired as its CEO and given that charge?

Among the unusual aspects of TR was his background in personnel management. American presidents tend to have little management experience. Those that do, tend to have served as governors of states. This can have some value, but is far more limited in scope and does not include familiarity with the byzantine federal civil service system, for example. TR, like FDR, supplemented his experience as governor with highly relevant national service. TR served as a federal civil service commissioner, and, as assistant secretary of the navy, delved into personnel management from the start. In addition, TR had experience akin to a start-up, raising a regiment for service in the Spanish-American War, then effectively leading it in challenging circumstances.

TR’s techniques are familiar and have universal application. He strove to cast a vision and then to personify it. He led from the front, putting himself at manifest risk in service of those in his responsibility. He relentlessly looked after the welfare of those he served. For example, he fought the military bureaucracy for better provisions for the Rough Riders. Throughout his public career, including as president, he would make unannounced visits to government offices, to check on the realities beyond the confines of dry reports. His devotion to his teams was reciprocated. Even as president, he would cast aside matters of state to pause and welcome Rough Riders who showed up, sometimes unannounced and without apparent cognizance of the imposition. Even as president, he would pay attention to senior and junior appointees and influencers, including his “Tennis Cabinet.” Many who served with TR would view their time together as the high point of their professional lives.

Roosevelt was a great leader while serving as the 26th President of the United States (1901-1909). In your opinion, would he be a great president if POTUS today? Please explain.

Great leaders redefine the general climate and understanding of their historical moment. That is part of their genius—and that’s why it’s difficult to conjure up what they would think in another time and place. TR was born in 1858. The past is, truly, a foreign country. Though Roosevelt speaks to us far more than most past leaders, and we feel him to be approachable and relatable, that really can only go so far in considering what he might think or today in the 21st century.

With those caveats, one cannot help but notice that today’s challenges echo those of the turn of the 20th century. Record-high immigration and the challenge of obtaining its value while limiting its costs. The rise of entirely new corporate sectors, in our time information enterprises, that require new thinking and approaches to governance. The rise of new financial arrangements that bring undoubted benefits, yet are subject to abuse. The subornation of politics to the new economic and financial arrangements, occasioning oligarchies prone to self-dealing. An overarching sense that self-interested private actions are threatening the very fabric of the commonwealth—putting at risk the notion of a shared national identity expressed in ideals of citizenship. And, of course, the baleful trend of talented individuals turning away from politics and public service in favor of the relative comfort and security of private life.

TR would recognize all of these issues. One can readily envision his taking them on, challenging the status quo to meet “realizable ideals.” As a historian, he would do so consistent with the American experience, striving to build a stronger edifice on that durable foundation. His dedication to the national ideal, going to back to Hamilton, dictated that he not see himself as simply representative this or that faction or special interest or political party. This made his leadership enduring. It also meant that, then and now, his approach did not fit well into conventional divisions of left and right.

What are some key facts about him that most people do not know?

TR had immense personal charm, or “sweetness” as it was then called. He could certainly be combative in public discourse, yet he could also be a calming presence in direct interaction. This unusual combination rendered him effective as a mediator of international disputes, just as he was an advocate for the use of force in other cases. Roosevelt was a person of genuine intellectual curiosity. He was a prolific writer. He could speak as a peer to academic historians, just as he could write and deliver speeches that would reach the everyday person. If Roosevelt’s public persona was ebullient, expressing an optimistic outlook, his private views could be realistic and even pessimistic in some cases. Perhaps most surprising, in our time of involuntary transparency and stripped pretenses, there are few surprises about Roosevelt. That is, he was authentic, just as he was self-created. As was often observed of Reagan, what you see is what you get.

Please explain his frequent references to a “bully pulpit.”

As with so many words, the definition of “bully” has changed over time. Today it refers to a person who abuses power or position vis-à-vis a vulnerable party. In Roosevelt’s time the term was also synonymous with “outstanding” or “excellent” or “awesome” or “brilliant” as these words commonly are used today, for emphatic declaration. TR has been called a “preacher militant.” He believed in a unique American nationalism built on “the foundation stone of… the high individual character of the average citizen.” With sustained intentionality, Roosevelt sought to transcend the indistinct presidencies following Lincoln with a conception of an active executive, serving as a moral force. For TR, who used words as instruments and sought to personify the values he advanced for individual citizens as well as the nation as a whole, the White House was the incomparable pulpit.

Much has been said and written in recent years about balancing a career and personal life. TR seems to have done that remarkably well. Please explain.

Edith and Theodore Roosevelt were exceptionally dedicated to their family and children. They eluded the familiar fate of political families, including Eleanor and Franklin Roosevelt, whose children’s lives were neglected, with foreseeable results. One reason for the success of the Oyster Bay Roosevelts in this respect is, quite simply, that they made it an non-negotiable priority. TR was ruthless in his scheduling and use of time. He would not allow “important” work of the moment to override his scheduling of time with his children. It’s also clear that TR simply loved children. He delighted in their company, as the sentiment was reciprocated.

Here’s one of my favorite Theodore Roosevelt quotations: “People won’t care how much you know until they know how much you care.” Your  response?

Roosevelt was focused like a laser on his audiences. He had sincere admiration for so-called everyday Americans, often referred to as “plain people” in that era before the emergence of the mass middle class. He expressed his love and respect in ways large and small. The multi-faceted actions of his life enabled him to share one or more manifest aspects with nearly any American. He was Northeastern and Western and Southern; he was urban and a cowboy. He was Harvard and a soldier. He was a family man and an adventurer. He was an intellectual and a man of action.

With which other President does Roosevelt share the most in common?

One can certainly see commonalities of Roosevelt with predecessors he admired, notably Washington and Lincoln. So, too he had commonalities with Jefferson and Polk, inasmuch as each of them as president seized opportunities to extend America’s boundaries across the continent. Most of TR’s successors have expressed commonality or affinity with him in one way or another. Even before he moved into iconic status, TR’s manifold aspects and accomplishments presented numerous aspects for identification. John Kennedy, the youngest elected president, credibly encouraged association with Theodore Roosevelt, the youngest president at time of inauguration. Of course, the president who shared the most in common with TR would have to be Franklin Roosevelt. This was no accident. FDR idolized his distant cousin and was connected to him through emulation as well as marriage to his beloved niece. An objective evaluation may be that TR was the greater man, while FDR, in part benefitting from TR’s example, was the greater president, leading the US through the greatest challenges of the first half of the 20th century.

Excluding the current occupant of the Oval Office, from which President does he differ the most?

Certainly his handpicked successor, William Howard Taft, and James Buchanan, and other presidents he would dismiss as hewing to an outdated, passive view of the presidential office.

Which great leaders did Roosevelt most admire? Why?

TR kept portraits of his father and Lincoln within his range of vision while he worked. He also expressed great admiration for Washington and Hamilton as founders and exemplars of the American national ideal.

In your opinion, of all that you have learned from various great leaders throughout history, what do you think will be of greatest value to those now preparing for a professional career or who have only recently embarked on one? Please explain.

There are so many examples to be studied from history! One can certainly actionable inspiration in many times, many places—and not solely from the most famous figures. The key, perhaps, is learning to apply history so as to better comprehend the present, with some capacity to discern and create the future. In seeking perspective on our current circumstances, I have found great value in studying many aspects of the pre-World War One period, as well as the interwar period into 1939. These were times of great turbulence and change, when the old verities were manifestly inadequate, and longstanding institutions required reform. Since America emerged, on the whole, greatly enhanced from those periods, there’s a risk of seeing the outcomes as inevitable. In fact, they were far from pre-ordained, and our position is, to an often overlooked extent, precarious.

There are numerous books holding value for people seeking to import guidance and inspiration from those times. For a start, one might consider The Vertigo Years: Europe, 1900-14, by Philip Blom, and The Dark Valley: A Panorama of Europe in the 1930s, by Piers Brendon. In turn, these works might well help ignite and then focus further exploration of history to be brought into service today.

To first-time supervisors? Please explain.

First-time supervisors are so often ill-prepared for their new role. They’re often promoted, in a linear fashion on an organization chart, after distinguishing themselves as individual performers. Management training can be vital, from the start, rather than after avoidable setbacks. The elemental notions of teamwork inculcated in sports and the military can be conveyed through relatable examples.

To C-level executives? Please explain.

The unusual demands thrust upon c-level executives, as well as their own unique mix of experiences, make it difficult to generalize. At the highest levels of positional leadership, the coaching and training that will hold the most value must be tailored to the individual. That said, one commonality is that c-level executives must learn how to relate to ever larger groups of stakeholders. In the doing, they risk becoming isolated.

Some will have a difficult transition as they become viewed as symbolic figures, objectified by others. Some will become overly reliant on their own prior experience as they have little time to reflect, and fewer people to consult who don’t have their own agendas. These are among the challenges facing all great leaders of history. Studying may help provide perspective in the demanding but simpler world of business.

To the owner/CEOs of small-to-midsize companies? Please explain.

Those companies tend to be entrepreneurial. Value creation, experimentation, courage, innovation, resilience, adaptability, and self-creation are at a premium. In addition to the nuts and bolts of management that can be learned from various sources, useful examples can be gleaned from the arts. If entrepreneurialism is in significant part a creative endeavor, one can learn from writers, painters, architects, musicians and others who strive to interweave the demands of the bottom-line with the impulses of a creative spirit.

To teachers, coaches, clergy, and others — other than family members — who have direct and frequent contact with students in grades 9-12?

Those entrusted with the capacity to influence high school students carry a great responsibility. Decades later, their example and tutelage—including things that might have seemed minor or merely off-hand at the time—can echo through the consciousness. Young people, understandably, may conclude that their own times are unique, that they have little to learn from history.

This is all the more true when their formal education in this respect is limited. It ought to be a criminal offense to convey history as a lifeless series of dates and events to be committed to memory. Anyone who can persuade young people to cultivate the habit of turning to history, looking beyond their own limited experience, is conveying a precious gift.

Being open to the lessons of history can fortify a number of sturdy virtues. Gratitude. Humility. Courage. Decisiveness amid uncertainty. Forgiveness. Kindness. A recognition that the life well led is built upon the hard rock of service, not the evanescent quicksand of fashion and rampant self-indulgence. With luck, they will come to understand that familiarity with history is a most practical, lasting gift. It’s a gift that they can repay by continuing the legacy in their own lives, when they become middle-aged and older adults.

Which question had you hoped to be asked during this interview – but weren’t – and what is your response to it?

Rather than respond to that request, I take this opportunity to thank you for this comprehensive interview. It’s an honor to take part, and I appreciate the stimulus of your unusually wide-ranging and informed questions, as well as the longer perspective included in them. Thank you also for your own indefatigable service and leadership in helping so many of us learn from your outstanding writing and guiding hand.

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Jim cordially invites you to check out the resources at his website by clicking here.

Here is a direct link to Part 1 of this extended interview.

Serve to Lead Group, Serve to Lead, Theodore Roosevelt on Leadership, Reagan on Leadership, Disrupt Politics, James Strock on Theodore Roosevelt and Other Great Leaders [colon] Part 2 of an interview by Bob Morris, The Vertigo Years [colon] Europe [comma] 1900-14, Philipp Blom, The Dark Valley [colon] A Panorama of Europe in the 1930s,  Piers Brendon


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