General Stanley McChrystal — Mastering Risk: A User’s Guide (#535)

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“The idea that we want to mitigate risk to zero before we act is really common and really costly.”

— General Stanley McChrystal

General Stanley McChrystal (@stanmcchrystal) was called “one of America’s greatest warriors” by Secretary of Defense Robert Gates. Having held leadership and staff positions in the Army Special Forces, Army Rangers, 82nd Airborne Division, the XVIII Army Airborne Corp, and the Joint Staff, McChrystal became commander of JSOC in 2003, responsible for leading the nation’s deployed military counterterrorism efforts around the globe. His leadership is credited with the 2003 capture of Saddam Hussein and the 2006 locating and killing of Abu Musab al-Zarqawi, the leader of al-Qaeda in Iraq. In June 2009, McChrystal received his fourth star and assumed command of all international forces in Afghanistan.

General McChrystal founded the McChrystal Group in January 2011, an advisory services firm that helps businesses challenge the hierarchical “command and control” approach to organizational management.

He is a senior fellow at Yale University’s Jackson Institute for Global Affairs, where he teaches a course on leadership, and he is the author of the bestselling leadership books My Share of the Task: A Memoir; Team of Teams: New Rules of Engagement for a Complex World; and Leaders: Myth and Reality. His new book is Risk: A User’s Guide. He is also the co-host (with former Navy SEAL Chris Fussell) of the No Turning Back podcast, where they explore the future of leadership and teams with the world’s most consequential leaders.

Please enjoy!

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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear the first time General Stanley McChrystal joined me on the show? Listen in on our conversation in which we discussed his exercise regimen, why he only eats one meal per day, the development of mental toughness, tactical and psychological lessons of combat, self-talk before and after difficult engagements, favorite books and documentaries, and much more.


  • Connect with General Stanley McChrystal:

The McChrystal Group | Twitter


Note from the editor: Timestamps will be added shortly.

  • What are Stan’s views of the current and developing events in Afghanistan?
  • How does Stan define risk, and why did he decide to write an entire book on the subject?
  • How did Stan go about organizing and formatting Risk: A User’s Guide to teach people to systematically think about risk in a smarter, more informed way?
  • Stan’s book Leaders: Myth and Reality studied 13 leaders — from Coco Chanel to Abu Musab al-Zarqawi to Walt Disney. Do any stand out as particularly deft in navigating their way around risk?
  • When considering risk, it’s important to separate the decision from the outcome (in other words, just because the outcome doesn’t turn out as hoped doesn’t necessarily mean the wrong decision was made).
  • On narrative as a risk control factor.
  • The risks presented by propaganda, misinformation, and disinformation.
  • How COVID-19 illustrated (and continues to illustrate) the failure of our system’s response to what should have been an easily mitigated risk.
  • Does Stan feel as if our system has improved as a result of this failure to be better prepared for future catastrophes? If not, what will it take to fix it?
  • What is red teaming?
  • What threats are we not taking seriously enough as a society?
  • The four tests leaders and teams can use to evaluate their communication.
  • How does someone train themselves to be more resilient to receiving candid communication — and less afraid to share it?
  • What Stan’s looking for when gauging someone’s ability to assess risk under pressure, and how this might be applied in a civilian setting.
  • Other people Stan considers to be excellent at navigating risk.
  • Parting thoughts.


“The idea that we want to mitigate risk to zero before we act is really common and really costly.”
— General Stanley McChrystal

“Acting with risk is really about reducing your vulnerabilities.”
— General Stanley McChrystal

“Threat times vulnerability equals risk.”
— General Stanley McChrystal

“If we’re unable to have the normal political debate to make processes work without doing huge pendulum swings to one side or the other, then the machine isn’t working right.”
— General Stanley McChrystal

“As long as the American government and society are working, we will get dinged up with threats that will come, but we will always be able to respond. When the system isn’t working, I think we are fundamentally vulnerable to COVID-19, to potential foreign aggression, to terrorism, cybersecurity, you pick any number of threats.”
— General Stanley McChrystal

“When we are ignorant, we are vulnerable. When we are ignorant as a society, we are societally vulnerable.”
— General Stanley McChrystal


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 600 million downloads. It has been selected for “Best of Apple Podcasts” three times, it is often the #1 interview podcast across all of Apple Podcasts, and it’s been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.