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Bold Leader Spotlight: Stanley McChrystal, Founder of McChrystal Group

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Being bold in leadership is often expected of our military elite for obvious reasons. The need for strength, confidence, and insight are critical in times of crisis. And the ability to effectively guide others on a mission while adhering to values is essential. Without question, Stanley McChrystal—better known as “Stan” by his co-workers, employees and friends—, a retired 4-star Army General in the United States, has fulfilled these roles during his tours of duty. But today, McChrystal is bold as a leader in other ways. And organizations everywhere are welcoming his efforts.

Throughout McChrystal’s military career, he served in an array of national and international leadership positions. Since his retirement, he now continues his leadership legacy by helping organizations become increasingly adaptable through the firm he founded in 2011, McChrystal Group. Part of this involves guiding these enterprises in being bold in the development of organizational leaders. Given McChrystal’s extensive experiences in leadership command, no one is better equipped to serve in such a role.

Jeff Eggers quoted
Stanley McChrystal’s has achieved great things by being bold.

Being Bold in Leadership—Committing to Values and Self-Discipline

As described by McChrystal, no one is born perfect or flawless. Being bold in leadership requires constant dedication to being true to one’s values and striving for continuous improvement. This pursuit requires being disciplined in one’s efforts to improve, and it starts with the simple things each day. Even when we stumble, it means accepting our faults and trying to be better the next time. In other words, being bold in leadership requires both humility as well as dedication. This is something he learned as a cadet at the U.S. Military Academy at West Point – although leaders are important, they are not the most important thing – the people you lead are.

McChrystal retired from the U.S. Army in 2010 after serving as Commander of the International Security Assistance Forces. Likewise, he has been awarded numerous medals and ribbons, including the Bronze Star. Naturally, attaining such positions and recognition required consistent self-discipline and the pursuit of personal improvement. But these efforts have not ceased upon him retiring from the army. In fact, even today, he identifies self-discipline as an area he wants to improve. Truly, McChrystal sees self-discipline both as an area that requires lifelong attention and an essential aspect of authentic leadership.

Being Bold in Leadership—Embracing Change and Taking Necessary Risks

Part of McChrystal’s professional endeavors today involves helping guide organizations in today’s complex environments. With today’s accessible real-time information and need for agility, being bold requires adaptability. And effective leaders must facilitate an entire organization’s ability to change not only periodically but also continually. Leadership must, therefore, prepare others for this dynamic capacity that is necessary for success in today’s global climate. Certainly, this endeavor will require being bold and taking risks. But as McChrystal describes it, failure to do so will undoubtedly result in eventual obsolescence.

In working with large organizations, McChrystal appreciates that structures are often in place to promote efficiency and predictable outcomes. However, while such structures may have allowed success in the past, they do not necessarily guarantee success in the future. The same applies to the military. As McChrystal notes, soldiers are trained to follow routines, but they are hired to win. Being bold in leadership means accepting this undertaking and challenging the status quo when change is needed.

Stanley McChrystal quoted
A bold leadership style has enabled McChrystal to achieve when most would have failed.

Being Bold in Leadership—Empowering Others and Delegating Effectively

McChrystal served as head of the Joint Special Operations Command during the Iraq War. During that time, he recalls having dozens of flat screens depicting the unfolding military operations in the field. But despite having this bird’s eye view, he believes he was not always in the best decision-making position. Those who were present in the moment and were experiencing it in its entirety were much better informed.

In line with this truth, being bold in leadership also requires empowering others to lead and to make decisions. It also demands leadership development so such decision-making can be delegated effectively. In working with organizations today, McChrystal encourages these pursuits, thus citing an overall leadership crisis in the nation today. Bold leaders and businesses of tomorrow, therefore, must embrace this role, which will foster long-term success into the future.

Keith Krach quoted
Keith Krach extols the leadership virtue of Stanley McChrystal.

Being Bold in Leadership—Exhibiting Humility and Empathy

While in Iraq, McChrystal led a special operations unit that targeted Abu Musab al-Zarqawi, the leader then of Al-Qaeda in Iraq. Despite opposing Zarqawi’s ideologies, he was able to empathize with Zarqawi’s commitment to a cause. And it was this same capacity that enabled McChrystal to empathize with those who followed him. In doing so, he was able to maintain an open mind and be more willing to see alternatives. Ultimately, this move made him a better leader.

Being humble and empathetic may not be considered typical of being bold in leadership. But according to McChrystal, they are essential. The resulting humility from recognizing one does not have all the answers encourages continued growth in oneself. Similarly, the resulting empathy from appreciating others’ perspectives fosters deeper relations. Being bold in leadership thrives in both circumstances, which is why McChrystal values both these leadership traits greatly.

Being Bold in Leadership—Stanley McChrystal’s Vision for Others

After serving in the U.S. Army for 34 years, McChrystal has retired and embarked on new leadership pursuits. Notably, he has authored two books, one of which is his memoir, “My Share of the Task”—a New York Times bestseller. He likewise has co-authored the book, “Leaders: Myth and Reality”, which is a Wall Street Journal Bestseller. In addition, he now heads the McChrystal Group, helping all types of enterprises become increasingly adaptable and prepared for success.

a cartoon of stanley mcchrystal
Stanley McChrystal is the author of “Team of Teams: New Rules of Engagement for a Complex World” and Co-author of “Leaders: Myth and Reality”.

In each of these endeavors, McChrystal has acted with a firm conviction in being bold in leadership. And he believes effective leadership will be increasingly required at every level of an organization for it to survive future challenges. Coming from one of the military’s boldest leaders, this vision of the future is clearly one worth acknowledging.

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