The Tim Ferriss Show Transcripts: General Stanley McChrystal — Mastering Risk: A User’s Guide (#535)

Please enjoy this transcript of my interview with General Stanley McChrystal, (@stanmcchrystal), whom Secretary of Defense Robert Gates called “one of America’s greatest warriors.” 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.

Transcripts my contain a few typos. With many episodes lasting 2+hours, it can be difficult to catch minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Amazon Musicor on your favorite podcast platform. You can watch the interview on YouTube here.

#535: General Stanley McChrystal — Mastering Risk: A User's Guide


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Tim Ferriss: Hello, boys and girls, ladies and germs. This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show. My guest today is General Stanley A. McChrystal. Who is General McChrystal? A transformational leader with a remarkable record of achievement. General Stanley A. McChrystal 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 Airborne Corps, 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’s 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 newest book is Risk subtitle, A User’s Guide. You can find them online at that is M-C-C-H-R-Y-S-T-A-L And you can also find the McChrystal podcast, which started last year, and that is called No Turning Back. General McChrystal, welcome back to the show. It’s good to see you, sir.

General Stanley McChrystal: Oh, Tim, please call me Stan. And it’s a pleasure.

Tim Ferriss: I am so thrilled to have you back on. This is, I think, round three if we count the follow up Q&A episode, and a tremendous amount has happened both in the world and in both of our lives since we last spoke. And I wanted to start with Afghanistan. And I’m looking at a paragraph that I pulled from an older interview, this is from the Financial Times with you. And you’re giving a tour, I believe of your home, to the journalist. And you pointed out a map and you said, “This is a hand-drawn map of Kabul by British officers from 1842. This is the route they took to Jalalabad. One guy made it out of 15,000. I kept it on my desk in Afghanistan as a reminder. ‘Let’s not be too sanguine.’”

And I wanted to begin with the current day. Everyone has seen so much news about Afghanistan. And I can only look at it personally through the lens of a lay person with very minimal understanding having never been there. What do you see when you look at recent events, if I may ask such a broad question?

General Stanley McChrystal: I think naturally I look at it probably two ways. I look at it emotionally because I see our opponent, the Taliban, now running the country. And of course, already there are indications that their regime is going to be very difficult on parts of the country, particularly females. But we’ll wait and see how that develops over time. And then I also look at it as someone who has been involved, at least in the military part of foreign policy. And so, I asked myself, “What does it mean going forward?” The first thing I’d say is though, people always ask me about what’s in the rear view mirror and they say, “Why did it come this way?”

And so I’ll touch on that and I’ll say that there’s a temptation to oversimplify, to find out the critical mistake, the wrong decision, the evil policy maker, the unaccepted reality, and that sort of the graveyard of empires and to say, “This is why it didn’t come out the way we wanted it to.” And I think that when we do that, we do two things. One, we miss many other factors, but we also let ourselves off the hook. I personally don’t believe that Afghanistan, and what we tried after 2001, was impossible. I don’t believe that the Taliban were 10 feet tall, I’ve seen too many up close to believe that. What I believe is in fact, many of the things that failed us was us. It was our weaknesses in putting together a coherent, well-coordinated effort over time. And sometimes that involved mistakes in decision making or halfhearted policies, but often it was just not being able to make the team of teams work.

And that’s frustrating because someone goes to the doctor and wants to know why they’re suffering a certain pain or malady. And the doctor says, “Well, you’re in poor health. You smoke too much, you drink too much, you don’t sleep, you don’t work out, you’ve got all these things, correct those and many of these other things will not happen.” And yet we don’t like that advice. We’d rather say, “Well, here’s the pill or the procedure I would do to solve that problem.” And so I think Afghanistan was as much a case of us needing to look in the mirror and say, “Why do we struggle with big efforts like that as anything else?”

Tim Ferriss: What do you think it means looking forward, when you’re looking at the windshield instead of the rear view mirror?

General Stanley McChrystal: I actually think the implications are quite large, Tim. And the first is our nation’s inability to do big things like this and it will undermine our confidence to take on efforts. And maybe there are many we shouldn’t but there may be some we should, and yet we will be averse to doing that because we will lack the confidence in our ability to pull things together and execute well. Maybe the other side of that coin is the world will look at us that way.

Most people of my generation who were born after the Second World War enjoyed a very distinct environment for our nation. Where people may disagree with things the United States did but there was this extraordinary respect for our capability in many cases, for our accomplishments. I think that has worn thin, I think in fact, we can’t assume we have the same level of credibility walking into any situation that we did even a few years ago. We will have to rebuild that credibility over time, and it will take a significant effort.

Tim Ferriss: Thank you for answering that. It’s been on my mind and a number of my friends who are veterans have texted with me about the events which have been very disheartening to many people who served. So I really am grateful for you shedding some light on your perspectives, since it would be only guesswork on my part. Let’s jump straight to it, and I do this very rarely, I very rarely jump to the new book. Usually, there’s a lot of background. We have though, had previous conversations, we’ve talked a lot about your history, we’ve talked about everything from your one-meal-a-day policy, for yourself, not for everyone else, to exercise, to training. And we’ll perhaps refer back to some of those.

And in fact, I’ll start with a reflection. I was looking back at a recap of our first-ever conversation on the podcast. And I asked you, and this will tie into risk I think, because most things tie into risk in some fashion, I asked you how you would train 100 athletes to become, well, as my team put it here, soldiers. And the athletic part was simply to check off the box of physical prerequisites. And the answer as it was paraphrased from here is that given that they have all the basic technical skills, you would push them in endurance live fire training, and in making decisions with incomplete information, decisions through which they’d be forced into bad outcomes and have to deal with those bad outcomes.

And that last portion is extremely interesting to me because certainly, the last year has highlighted how difficult it is for most people, if not all people, in some circumstances to make decisions with incomplete information. And I spent a lot of time thinking about risk and mitigating risk and even just defining risk. So could you maybe start with how you define or think about risk, and why write an entire book called Risk: A User’s Guide?

General Stanley McChrystal: I hit a point in my life, I’m 67 now, where much of my life I had been experiencing risk, trying to deal with it, trying to mitigate it in some cases, trying to avoid it in other cases, and watching other leaders do the same and I came to the conclusion we don’t do it very well. We’ve never really done it very well. We had matrices and calculations that we use, but at the end of the day, most of the decisions were pretty subjective. And they weren’t made on data, they were made on sometimes experience and sometimes just, we’ll call it, gut feel. And our outcomes were uneven at best. And I came to the conclusion that the greatest risk that we face is in fact us.

If we’re worried about the risks in the world, we should go look in the mirror because most of the other risks we can’t do anything about. There are external risks that will inevitably emerge, they will be impossible to predict with great clarity, either in the timing or exact nature of them. But we can absolutely be confident that they will show up, and they will impact us. And unless we’re extraordinarily fortunate or nimble, we won’t judge them completely, we’ll be impacted by them in some way. And we will have to make decisions based on that.

And so, when I talked about preparing athletes to be a team, a world class team or to be soldiers in combat, I start with yes, the absolute assumption that risks will emerge that will be have to be dealt with, and the impact of those risks will be at first unclear to people, but they will have to make decisions in the moment that in themselves carry risk. And so, what I mean is there’s a risk emerging, making a decision carries risk as well, it carries reputational risk, it carries potential costs. A leader in combat often has to decide to do things which may carry significant costs and casualties from their force.

Now, the desire is to wait until you have perfect information so that you don’t do something that turns out to be an effective. But of course, we all know that not making or delaying a decision is a decision in itself and carries its own risks. Unfortunately, we have habits which often say that the person who actively makes a decision and goes a certain direction and has a bad outcome or it is costly, is held accountable. But someone who doesn’t make decisions, we don’t hold them to the same account. We sort of say, “Well, they didn’t make decisions and so they’re not really responsible.”

I found in the counterterrorist world, we used to get opportunities arise. And, you call it, a certain terrorist would be located somewhere and we have the opportunity to arrest or to target them, and we have to get a decision. And some of those decisions would have to go all the way up to the highest levels in DC. And so what you do is you’d go to decision makers and went through a series of levels. And often, partway through that some decision maker bureaucrat in the system would go, “Well, let me ask a couple questions, how much wood could a woodchuck chuck?” And I’d go, “What are you talking about? There’re no woodchuck’s in this.” And they’d say, “Well, I need to have more information before I can approve it.” And so we’d go back and we’d find out how much wood woodchuck can chuck and then we come back, by that time, the opportunity had passed.

And what happened was that decision maker would then look at me and say, “Dammit, Stan, I wanted to improve that. You need to come better prepared so I could approve it.” And what they had really done is they hadn’t accepted the risk of approving a mission, they hadn’t accepted the responsibility for disapproving, they’d sidestepped it. And they’d had the effect of preventing us in doing anything. And I don’t know how many different permutations of that I’ve seen. But the idea that we want to mitigate risk to zero before we act is really common and really costly.

Tim Ferriss: I was looking back at the notes from that first episode that I mentioned and the second part to that answer a bit later on, with respect to hypothetical training of 100 athletes was, and again, paraphrasing, indicating that what you’re looking for is largely that the commander’s were reflective and not just making knee jerk decisions. There’s no right answer, necessarily in those situations, just a more thoughtful way of arriving at the answer, right? And this is something that I see a lot also in the best investors in the world, who I’ve been lucky enough to interview or spend time with.

And that is they have to be very careful about separating process from outcome so that they are rewarding good process, even if you happen to pull a joker card and get a bad outcome and vice versa, right? Not rewarding bad process just because somebody happened to pull the ace of spades out of the deck by sheer luck. How did you think about organizing Risk: A User’s Guide and actually formatting the book to teach people to systematically think about risk in a smarter way, or perhaps a more informed way?

General Stanley McChrystal: We started by looking at what risk really is. And of course, most of us think of risk is that intersection between the probability of event occurring and the consequences if it does. And if the consequences are low or if the probability is low, we don’t worry about it, if both rise up and suddenly we take notice and we try to do something to mitigate it. You can also think of risk slightly differently as a mathematical equation. And you say that mathematical equation is, what is the threat and what is your vulnerability to that threat? And literally, it’s threat times vulnerability equals to risk.

So if the threat to me is somebody with a handgun and I am walking down the street, and they want to shoot me, and that handgun would hurt me, I’ve got a pretty high level of risk. If however, I’m in a tank and they have a handgun, then suddenly my vulnerability is much reduced and so is the resulting risk. And if my vulnerability is zero, my risk is zero. So if I can either reduce the threat to zero or the vulnerability to zero, I’ve taken it to zero. Now, very rarely can we do zero in either, but we don’t control the threats much. We do control our vulnerabilities. We control what can hurt us and what we can do about it in the moment. So we started to think about risk, acting with risk is really about reducing your vulnerabilities.

Think of the human immune system, and this was the analogy that jumped out at us, the human immune system fights off something like 10,000 pathogens a day which could make us sick or kill us. And we don’t think anything about it because when we’re normally healthy it just detects, assesses, responds, and learns from that process, and we go on our merry way. If our immune system is weakened because we’re sick or we have an autoimmune deficiency, suddenly those things which wouldn’t bother us on a daily basis become potentially very dangerous.

And so, if we start to think about that, then the reality is every one of us as individuals and every organization has the equivalent of an immune system, which is either healthy or it is not healthy. And we could call it a risk immune system. And that’s, in the book, we offer a model in which there are 10 factors or risk control factors. And those risk control factors such as communication, narrative, timing, action, bias, diversity are all components of how well you and your organization are able to detect risks, assess their potential threat to you, respond to them and learn from that. And so, the trick is to understand those risk control factors, strengthen those as both individual factors and as a system, and keep yourself as healthy because you’re accepting the reality that you can’t prevent all the threats from emerging.

Tim Ferriss: I would love to delve into the world of stories, maybe case studies. This may be a way of tying some of your previous work to this as well or you could pull from the new book. You wrote a book, as mentioned in the intro, Leaders: Myth and Reality. And this was a plutarchian study of various leaders, 13 case studies ranging from Coco Chanel to Abu Musab al-Zarqawi, including Walt Disney, many others. Are there any of those leaders or other leaders who come to mind who have exhibited intelligence or excellent execution around risk? Are there any stories that you might tell that would pull together some of the concepts we’re discussing? Or just a general story about someone who’s excellent at interacting with or thinking about risk?

General Stanley McChrystal: Absolutely. And maybe the unexpected one is Coco Chanel. And of course, she was born in the late part of the 19th century of modest upbringing. Her father essentially deserted her when she was young. So she grew up as a de facto orphan. She had, if you look at it, no opportunities and she was probably going to be relegated to not much in life. And yet she became initially a nightclub singer and a courtesan, you might call it. And she ingratiated herself with some people who had more money and so she got an opportunity, and partly it was her physical charms and her willingness to use them.

But then on the other part, the risk of there is she becomes minimalized, she becomes personally a commodity and she wasn’t going to accept that. And so what she wanted to do was create an identity and an opportunity for herself that was beyond that. And so she did an amazing thing. First, she designs an entirely new line of fashion. And she intersects with a period when simpler fashions during the First World War, the costs and whatnot, were accepted. But she also becomes the brand herself, she decides to transform herself into the walking embodiment of the lifestyle her fashions are designed to sell, a little like Ralph Lauren did a couple of generations after that.

And so the risks to her were overwhelming. And of course, as a female gets older, the idea that a female is going to be able to still be a fashion icon is non-traditional because typically it’s for a young period, when they are very physically attractive. But instead what she did was she became iconic, first as a fashion icon herself and then as a power in the industry developing Chanel No. 5, becoming a business tycoon, that’s the only way we can say it. And so, that one jumps out at me.

The other person who is probably unexpected is Dr. Martin Luther King, Jr. Because when Dr. King led the civil rights movement, you think, well, obviously, there’s opposition from entrenched forces. The whites in the south didn’t want progress. But in reality, what he realized the risks to the civil rights movement were really wide and, we’ll call them, diverse. When he wrote his famous letter from a Birmingham jail, he was actually criticizing moderate Southern or moderate national white clergy, who had said, “Dr. King, we agree with the aims of the civil rights movement, but you’re too aggressive; you’re pushing too hard.” And he understood that the real risk to the civil rights movement was not the very impassioned, violent response from Sheriff Clark in Alabama, in fact it was inaction, it was passive support from the rest of white America.

And so, Dr. King understood those risks. And what he had to do was take them on with a campaign that went the entire breadth. He had to campaign not just against those entrenched, George Wallace-like interests, he had to campaign against the people who lived far away from the Deep South, and yet whose support politically was essential to the civil rights movement, things like the Voting Rights Act having an opportunity. He had to convince presidents Kennedy and then Johnson that it was in their political interest to take political risk, to push something that was important to Dr. King in the civil rights movement. So his understanding of risk to his movement and how to put other people at risk, almost like a chess master, so that he could maneuver them into support was pretty impressive. And when we think of Dr. King as a great orator saying, “I have a dream,” and we leave him two dimensional, then I think we miss a master strategist.

Tim Ferriss: Those are two outstanding and very unexpected in different ways, in different ways unexpected examples, so thank you very much for that. I’d love to just mention something for people listening and that is, defining risk for yourself is extremely, extremely, extremely important. If I could just kind of pontificate on this for a second because if you don’t define it, you can end up being this very vague, hazy specter that affects you but is untreatable. So I loved your, if I’m recalling it correctly, threat times vulnerability as an example of that. For myself, I’ve often thought about risk as the likelihood of an irreversible negative outcome, just from the investing and business perspective, right?

So you have for instance, Walt Disney since I just mentioned Walt Disney, I was listening to a case study of Walt Disney and the company and the fact that Walt Disney and company at effectively, and please correct me if I’m getting this wrong, but in a break even proposition at best up until Snow White, which changed everything. And it was a huge investment but it also returned the entire fund, so to speak. It made up for losses and of course, it’s a hits driven business. So as long as you can afford the potential of it being a failure, investing the amount of money necessary to test the new technology then allowed them to recreate, reinvent, and ultimately build this empire of a company. And I would love to hear any other examples that come to mind.

Another one, just to riff because I’ve had enough caffeine this morning, is Jeff Bezos. And we don’t have to spend too much time on Jeff Bezos, but I was reading a story about one of their product failures, I think it was, I want to say the Fire Phone. And at the press conference, I’m paraphrasing all this, I might get some of the details wrong but he said, in effect, “Oh, just wait. We’re going to have much bigger failures.” Because from those experiments ultimately, he had confidence with his team, with the methodologies that they would create incredible successes like Prime, which was very much doubted and ridiculed in the early days. And of course, it’s become something quite different. Are there any other stories that you might be able to share of leaders, they don’t have to be well known, they could be who have exhibited good thinking or behavior around risk?

General Stanley McChrystal: I’d start a little bit back with Walt Disney because you are correct, he in fact, mortgaged Mickey Mouse to fund Snow White.

Tim Ferriss: I did not know that.

General Stanley McChrystal: Yeah. The intellectual property of Mickey Mouse, he mortgaged so that he could make the movie Snow White. But risks continue to change. So Walt Disney, of course, is wildly successful with Snow White, it changes full length animated movies. In fact, it was the first movie and he said, “I can make audiences cry as well as laugh.” And once he learned they could do that, of course, we have the whole library of Disney movies now. But as the company changed, he went through a number of crisis points. Early in the Second World War, he had a labor struggle inside his firm. And the company was evolving and Walt Disney began to understand he was not the right guy to run it.

And so the Walt Disney of when I was a child and I watched the Wonderful World of Color, and Uncle Walt would come on and introduce Davy Crockett was now focused on things which were his strength, like development of Disneyland and then Disney World. And his brother Roy, in fact, took over much of the running of the business because they had come to the conclusion that the risks had changed, the requirement had changed. And the risk had changed so Walt Disney was much more effective and focusing on those things that were his strengths and his interest, as opposed to trying to do something for which he’s not really well suited. If we think about decisions in risk, and I’m a big fan of Annie Duke, the poker player. She will talk a lot about probabilities. As you mentioned, Tim, you’ve got to separate the decision from the outcome.

And let’s go to Afghanistan again for a moment because everybody is very upset about the withdrawal from Afghanistan. And the reality is had the Taliban not moved quickly and toppled the government and American forces had come out quickly and in being gone before the government of Afghanistan fell, it might be viewed as a brilliant stroke. People have different opinions on the wisdom of the overall, but that particular outcome of that decision might be viewed entirely differently. Because the outcome, what you’ve really got to do in my view, on a decision is go back to two factors. The first is, are they making the decision with the right values in mind? Are they using integrity and the things that represent you as an individual and you as an organization? And then the second, is it a rational decision probability wise, what they know then?

There’s an interesting analysis to go back to the Japanese admiral who was defeated at the Battle of Midway. And there’s the famous moment when he makes a decision to rearm his planes. And he rearms his planes and during that process the American dive bombers come in and destroy three aircraft carriers in a matter of minutes, and change the course of the war. And we step back and we go, “Look at that Japanese admiral, he just didn’t have his act together,” and whatnot. But if you analyze the information he had in the moment and each decision as he made over time, they were completely rational. In fact, they probably would be the decisions you or I would make.

And so. when we go back to look at it, and we get so fixated on the outcome because it didn’t work, it must have been stupid, then we don’t teach ourselves how to do risk management and decision making. Because in reality, you may make a number of decisions that don’t work out well. But as you mentioned, Jeff Bezos, as he’s building a stronger team and he makes some decisions that don’t work, one, they are learning from those decisions, two, as the team gets stronger, he knows that the probability of success over time is continuing to rise. And so, our argument in our book is as you continue to strengthen your organization’s risk immune system, your probability of success in every endeavor goes up. Because you are healthy, you are more able to accept the really bad piece of luck. Because when probability evens out over time, you’re in a stronger position.

Tim Ferriss: And the threat times vulnerability equals risk is really important on a multitude of levels, of course, because if the, I’m thinking if either side is too big a number and the other side isn’t zero, you have a large problem on your hands. And if you look at Annie Duke, poker, I think her book is Thinking in Bets, if I’m recalling correctly.

General Stanley McChrystal: Yeah. Correct.

Tim Ferriss: Or you look at say, a book like Bringing Down the House by Ben Mezrich, which was about this team from MIT who had a system for winning in blackjack. You can have the best system in the world but you also have to have, in this particular case, enough bankroll, enough money to sustain an extended string of bad luck. And I would love to jump to the 10 risk control factors, one jumped out that I’d love to hear you speak more about and that is, if I’m recalling correctly, narrative or narratives, would you mind expanding on that?

General Stanley McChrystal: Narrative is what we say about ourselves, and it’s how we want to be defined. We begin in the book with the story of the Alamo and William Barret “Buck” Travis, stands out in the courtyard of the Alamo, he draws a line in the sand and he tells, “Whoever will stay with me for victory or death, we will defend the Alamo,” of course history says everybody came across the line. And the reality was the Alamo was tactically operation is strategically insignificant. It bought a little bit of time for Sam Houston to build up the army, but the reality is, it did not matter much.

But in terms of narrative, “Remember the Alamo” became a call across Texas and actually, that’s infected across the United States of resolute people absolutely committed to win their independence. And so, the Alamo becomes important all out of proportion to its scale of the fight itself. And so, the narrative becomes the story, it is the power. A little like the 300 Spartans or David and Goliath, the reality is the story becomes the thing. And so, the narrative becomes very powerful for an organization. Think when we believe in the narrative, we think we believe the narrative of the United States, we touched a little bit earlier about the potential that our credibility could be weakened. Suddenly, the narrative that the United States having the kind of values that should prevail in the world and the power to prevail in the world, they go hand in hand.

If we look at a case where they get at cross purposes, Google is a tremendous case in point. In reality, Google started with the idea of “Don’t be evil.” And I remember when I first saw it I said, “Well, that’s a really catchy idea. And who couldn’t be for ‘Don’t be evil?'” And then you say, “Well, what does ‘Don’t be evil’ mean?” Well, it’s a little bit in the eye of the beholder but it’s still generally powerful, we’re going to do good things. And then in 2017, when Google started working with the Defense Department on Project Maven, some of the people inside Google felt like that was in opposition to the narrative, in opposition to Don’t be evil. And the culture in Google was that everybody would be googly, speak up, have their say, and help shape the culture. And they had a very serious crisis on their hands because a number of people in the company felt like the leadership had lost their way and was violating the narrative.

And so, we call that a say-do gap, the difference between what we say and then what we actually do. And so, the power of narrative, it’s critical that we have one but it’s also critical that we understand what it is and that we be true to it. And if we’re not prepared to be true to it, we should change it, we should reflect what it really is.

Tim Ferriss: As you discuss narrative, I can’t help think about a few things. Number one is how much our individual and collective realities are governed by these stories, of course. And also, the incredible power and damage that can be done when your software that’s being installed is a story not of your choosing, in a sense. So I’d love to ask you about the power or risks of propaganda and misinformation that seem to be coming more and more prevalent, certainly, with the amplification of technology, and sort of ubiquitous social media, and so on. But could you speak to that if you have any particular thoughts?

General Stanley McChrystal: Yeah. I personally think it may be the biggest threat to American society today and that is true in many other societies as well. If we go back to just the power of information of what we believe, we fall in line behind certain narratives, either a patriotism or identity of the organization we’re a part of, and they’re critical. But we also listen to information that comes and influences us. We are all influenced by advertising, we’re influenced by slogans, we look at of course, the master, Adolf Hitler, who created an entire idea that Germany had to come back into the world after the First World War in a proud and strong way. And then he pushed a number of ideas were of course, much more extreme than that. But Adolf Hitler was still popular in Germany the day he was killed in 1945.

Now that’s unthinkable because after 12 years of essentially taking his nation to war and destroying it, Germans still believed in him because the power of the message was so, it was almost like a narcotic. And we say, “Well, that could never happen to us.” Well, let’s look at tobacco in America. Back in the 1940s and ’50s it became clear that tobacco was a carcinogenic and nicotine was, of course, highly addictive. And as that information started to become really, logically irrefutable, the American Tobacco Institute, which was funded by big tobacco, implemented a very clever campaign. And they didn’t take on the idea, they didn’t say “No, tobacco doesn’t cause cancer.” What they said is, “Tobacco may cause cancer.” They left a little bit of daylight and they left each person who wanted to smoke. They left him daylight to say, “Well, it may cause cancer, but it may not.” And the American Cancer Institute played this over and over enough doubt, so that people could continue to market cigarettes, people could continue to smoke, people could argue about that.

And we realize how vulnerable we are to either blatant misinformation, what one side calls the Big Lie but also to very subtle misinformation, which much of it is true. And suddenly we start to believe things and act on those. If we look at the state of the American political environment right now, we’ve got a polarization that is as stock is, I think we’ve seen since right before the Civil War, and there were strong economic causes for it then. And we don’t have the same root causes now pulling us apart, now they are more tribal, they are more cultural, they are more informational, and the ability to have our mind shaped.

If I was in tech right now, if I was a big tech leader and we were talking about risks, I would get up in the morning and I’d say, “I may have created the thing that is going to destroy my firm,” meaning if I am in social media, I may have created a suicide machine because that which they have created is so damaging that in fact, there will be a revulsion against what is happening to our young people and to a degree to ourselves. And so, I think that if tech leaders don’t get in front of this and start to understand it, I could argue the same may be true of artificial intelligence as we start to employ it more and we understand the impacts, I think that leaders have got to understand that the actual risk to them may be now in failing to get in front of it, and act on that now and shape it so that it is not as damaging as it can otherwise be.

Tim Ferriss: I have to just raise my hand and concur 100 percent with that. And there’s so many different threats, let’s just say, threats that people might consider existential threats. And the discussion of tech and social media inputs and the behaviors that are reinforced by those technologies and the belief systems that are also created and reinforced, I find absolutely terrifying. And I say that as someone who has, let’s just call it, a monthly audience of somewhere between 15 to 20 million people.

And many of these listeners and readers are consistent, so I’m able to see changes in behavior over time. And the collective changes and individual changes, I recognize a lot of these names now. Hundreds and thousands of people who have been in my communities for many years, the degree of polarity and rage that I’ve seen in mass numbers of people, I recognize who did not have, or in whom I couldn’t see those characteristics earlier, is really mind boggling. So I have to agree with you. What — 

General Stanley McChrystal: Tim, can we talk about — 

Tim Ferriss: Yes.

General Stanley McChrystal: Can we talk about that in relation to COVID?

Tim Ferriss: Yes. Please.

General Stanley McChrystal: Because if we think about COVID, it was almost the perfect enemy. And I say it was perfect because it was inanimate so it was okay to hate COVID, you didn’t have to have any sympathy for COVID. And so, it was like out of a movie if aliens had come from outer space, the entire world could righteously unite to fight that. Now we have that, it wasn’t from outer space but it was that. And so we have this emerging threat that could and should have united us extraordinarily well. And our first excuse is we say, well, we were surprised; we didn’t see it coming. And the reality is, although we didn’t know COVID-19 would come, we absolutely knew that another viral infection that could be a pandemic would come because they have come with frightening regularity in history. So its appearance was inevitable.

And then the second thing is we absolutely knew what to do about it. The science of public health is pretty good and so we knew what works and what doesn’t work. And then we literally got a scientific miracle because they were able to produce vaccines in a speed never contemplated before and almost a freebie. So if you line those all up, and we had even done an exercise in 2019 inside the United States Crimson Contagion to war game this. And we had war gamed a viral infection coming from China beginning in Chicago and us struggling with it, so we had war gamed a pretty painful outcome.

And then when COVID-19 arrived, what did we do globally? We acted as individual nations. What did we do nationally? We froze to a great degree at the national level for a period, we had problems with our narrative, then we executed, at least on the state level, but I could argue we’re even more atomized than that many cases we operated at a municipal level. And no organization at that level has the resources or the ability to effectively fight a pandemic by itself. It has to be a united effort. It actually has to be a global united effort.

So my point is, our vulnerability was self-induced to COVID-19. COVID-19, like the Taliban, is not 10 feet tall, it’s eminently defeatable. And so what we should do is we should say, we failed as a system. We can’t look for a single person who screwed this up and pin the tail on him. We failed as a system and that should worry us because where we fail as a system means the next threat that arises means our system has already proven its limitation and we better look at that system.

Tim Ferriss: I was just thinking about this last night, probably because I had this conversation on my mind, and I was thinking a few things. Of course, the death toll is atrocious, we are not fully out of the woods. The numbers also, I think have just not had the psychological impact that other events like 9/11 would have because like you said, it’s this invisible, intangible, in some ways abstract, also long-term death toll.

But imagine if we had been hit with Delta first, or imagine if we were hit in 2000, who knows, let’s just make it pretty recent, 2005, 2010 when we had fewer technologies that would allow people to work remotely, and what the impact would have been on the economy. In a sense, we are having and did get a very important dress rehearsal because it’s not going to be the last pandemic or nationwide, perhaps even global catastrophe that we have to contend with. Do you feel like we have improved or fixed some of these systems or addressed any of the systematic failures to be better prepared for next time? Would you imagine that we have?

General Stanley McChrystal: Tim, I was on two commissions last year, one from the Council on Foreign Relations which explored this question and came up with recommendations, and then another from an organization called the Business Executives for National Security. And both of those commissions were formed of really smart, accomplished people and me and I was put on as sort of a comic relief. But the reality was, we fixed a few things. But the reality is, most of the things we fix which are systemic in nature, our communications, how we coordinate these things, how decisions are made, how we resource the different requirements for public health, I think had been woefully under addressed so far.

I think one of the things that you notice or that you mentioned, it’s just so important, we have the ability enabled by technology to continue on many things we do, many businesses could continue to operate generally. Actually, I think part of that is unfortunate. Part of it’s wonderful, it’s a miracle because our economy didn’t completely disappear. But if our economy was not able to limp along at first and then to come back like it has, we would have been forced into more decisive activities against COVID-19. Because we could essentially push much of the suffering onto parts of our population.

People like you and I, who might have the opportunity to work from home and what we do, can be enabled by that. We didn’t have to do things which I think might have forced us to address those vulnerabilities. And I think that may be a long-term challenge for us because if something isn’t bad enough, you don’t fix the problem. If people come out of COVID-19 thinking, well, if we only lose 600,000 people, I didn’t know many of them anyway so it’s okay, that’s a problem.

Tim Ferriss: Yeah. That is a problem. What do you think it will take for things to be fixed? Is it going to require something of the scale of another pandemic with even worse outcomes to force the hand, or do you feel like there are things that can be done to catalyze those changes in the meantime?

General Stanley McChrystal: I would like to believe that — I know that things can be done and most of them have been identified, I am not confident we will do them. I think on the margins, we are doing some things certainly and we’re getting smarter. And so, part of that will happen but I would pull us to cybersecurity. We have a very similar situation with cybersecurity right now that we do with pandemics because a huge cybersecurity challenge is inevitable, it’s not possible, it is inevitable. And when I talk about huge, I’m not talking about target having some customer data exposed. I’m talking about things that we rely on stopping for at least a period, maybe it’s banking, maybe it’s our energy distribution, things like that. I think it’s an absolutely inevitable that will happen.

And the question is, will we address it before that happens in a big way? We have done a number of things but this requires a public private partnership on a level we’ve never had before between the government and big corporations because cybersecurity isn’t something that you put a big cybersecurity defensive measure in a line at the nation’s borders it’s not like that. cybersecurity is something that is in depth, it’s built into all of our systems. And it also has to be built into our culture of how we operate, and what private security and liberties we’re willing to have shaped to get greater security.

And so, I think where we are is we’re extraordinarily vulnerable but we are, to a certain degree, have our heads in the sand hoping that they’ll get somebody else. I think many businesses right now get up every morning and know that they could be the target. And they’re happy if somebody else gets hit.

Tim Ferriss: I’ve so many follow up questions. We spoke about this in one of our prior conversations, but I think it’s a concept worth revisiting. And that is the concept of the red team or red teaming, would you mind just describing what that is? Because I think it’s even as a thought exercise, and sometimes it’s difficult to take on both parts as a single person because you’re too close to your systems, too close to your problems. But would you mind describing what a red team is?

General Stanley McChrystal: Sure. It’s essentially making somebody the bad guy and commissioning them to screw you up. And you say, “Well, why would I do that?” Because we become blind to our vulnerabilities. There’s a great story from a war game called Millennium Challenge, which happened before the first Gulf War. And a marine general named Van Riper, lieutenant general, was made the commander of the opposition essentially in a red team role. And he looked at how this was likely to play out because he was playing a Mideast nation. And so, he said, “I’m not going to let the Americans do what they’re good at, I’m going to do a preemptive strike.” And so he did a preemptive strike in the game, he killed the equivalent of 20,000 Americans. And he really screwed up the American plan and so they stopped the war game. And they recocked him, went back, and they said, “Okay, we’re going to continue, but don’t do that again.”

And it was like, wait a minute, the whole idea of a red team is to find clever people who will come and find the holes in your plan. Where are there gaps and seams or flaws that you have become blind to? Where will they, as you inflate, it’s that tire inner tube that you’ve been working on and you patched you inflate it and you see if there are any more leaks, where are the leaks? A good red team is people who are a step outside your organization, you can have people inside, but they have to be fenced off and so that they are not wedded to the plan. Because if they’re wedded to the plan, they’re incentivized not to find flaws in it.

And so you’ve really got to have a red team that’s incentivized to find flaws, and then the leadership has got to act on those. When they find those problems, gaps and seams, the leadership has got to follow up and got to close them. And they can’t make the red team pariahs, they can’t say, “You people are bad people because you’re disloyal to our plan.” No, the greatest loyalty you can ever do is to make it stronger. And so, I’m a great believer that red teaming takes us out of being comfortable and we’re all guilty.

I remember that as a commander in combat, you’d work a plan for a long time, you’d do all these things and if somebody questioned it or poked a hole in it right when it was time to execute, you got mad. Because dammit we’re about to execute this plan, don’t distract me, don’t do that, that’s irritating. But you need them to do that. And so, red teams are really effective way to the pressure test.

Tim Ferriss: So when you look at, we could say, this country, we could speak globally also, but what threats either most concern you or which threats do you think people are not paying enough attention to? And I’ll let you define threats and people as you like?

General Stanley McChrystal: I think not surprisingly I’ll tell you that, the one that literally leaves me up at night is the failure of our system to be able to do routine things routinely. And when I talk about is when our government is seized up with partisanship, and we are unable to do the normal functions as outlined in the Constitution. 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. 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. Then there are some other issues that, of course, jump out, cybersecurity, of course, is the one that I would spend most of my time worried about because I think it’s immediate.

I think that climate change is one of those cases where if your neighbor’s house was on fire, you would go do something about it. The reality though is if there was a fire 10 miles away that was burning up all the fields that produce the food you eat, it wouldn’t be as apparent to you. And so, you might not run outside and call the fire department. And I think climate change is one of those cases where we are literally destroying that which we are dependent upon. But because it’s not happening in crisis speed that we think of in fast rolling time, and it’s happening more gradually, it doesn’t seem as dangerous. The problem is the corrective time is also much slower. So you can’t just put out the fire to your neighbor’s house, it takes a long time. So climate change.

And then finally, I would throw out education on a very national level. If you don’t have an educated population, then you’re not going to be competitive internationally because the days of the United States having this huge geographic and social advantage are gone. There are so many other places that educate a lot of young people and now they can compete. So that’s the one. And second, if you don’t have an educated population, you get ignorant stuff happening. Many of the great ills in life are because people just don’t know. And when you are subjected to the kind of misinformation in our society, you arm people with knowledge, you give them the ability to understand.

We used to deal with many people who would come in as terrorists into Afghanistan. And many had been taught in madrassas in Pakistan, they’d been taught the Quran and they memorized it but they didn’t speak Arabic. So they didn’t understand what they were reading, they required the interpretation of whoever was teaching them. And so, they were entirely vulnerable on someone else telling them what was right or wrong. They couldn’t do the critical analysis because they didn’t have the education for it. So as a consequence, they became vulnerable. When we are ignorant, we are vulnerable. When we are ignorant as a society, we are societally vulnerable.

Tim Ferriss: Let’s return to arming with knowledge. I would love to explore communication a bit, it just seems like the glue, the connective tissue that holds so much together. Could you elaborate on your thoughts about the four tests leaders and teams can use to evaluate their communication?

General Stanley McChrystal: If we think about communication we say, “Well, I got a cell phone and she’s got a cell phone so we’re in communication.” No. I think that means you could potentially communicate but there are four tests that decide whether you actually communicate. And the first is, technically, can I get my message to the person or people that I’m trying to communicate to? Can I send a letter, write an email or whatever mode that you need to use, can it get there?

The second is more subtle but more often a big issue, it’s will I do it? Will I communicate my message? Will I tell the people in other silos in my company or in other places? Will I pass them the information? And it might be I won’t pass them because I don’t like them, it might be I don’t pass it because I don’t know they exist, it might be I don’t pass it because my boss hasn’t given me approval. There any number of reasons not all of which are black and white evil, but the reality is the second test if you won’t pass information, there is no communication.

The third starts to be can the person receive it? Can they understand it? Am I transmitting in English and they speak Chinese? Or are they have a mindset that just is not willing to hear what I’m saying? And then of course, the final one that goes hand in hand with that is what I’m passing accurate and timely? So am I giving them good information that would truly be a value and are they capable of receiving it? So if you don’t have a yes, on all four tests, you don’t really have communication. And if you don’t have communication both ways, one, you don’t know if you’re communicating.

And two, you can’t have the iterative importance of communication where you say something to me, I process it, I talk back to you and there’s a dialectic which occurs, which over time opposing thoughts start to get to where we can get to something approaching rational reality or logic. With me thinking, when I think in jamming it to you, we don’t get there. And if I can’t get it to you, it doesn’t happen. So it’s got to be two ways.

So communication and an organization is really of the 10 risk control factors. We had hours of argument over which was most important, leadership or communication? I think communication is that our table stakes. If an organization can’t communicate internally or won’t, then they can’t respond to anything. The human immune system risk requires the ability of the body to sense threats, communicate, backup, whether they are dangerous, and then whether we should do something about it. If we can sense threats in our society but we can’t communicate, we can’t do anything about it. And so, therein lies the challenge.

Tim Ferriss: So let’s talk about one puzzle piece within that challenge, and that is being willing to receive or hear. And I want to focus on this because I feel like alongside the polarity and the polarization that we’re seeing in a sea of propaganda and clickbait and so on, online, there’s also a fetishizing of fragility in a sense, and we don’t have to spend too much time on that but I do want to spend some time on the opposite. So what I’ve noticed certainly in many teams, even among friend groups, and so on, there is a hesitancy to share certain things for fear of upsetting another person. So ultimately, being willing to share is a negative for fear that the willing to receive will not be there.

And I’m curious to know if there are any approaches you’ve seen that are really effective for people to train themselves to become more resilient in being able to receive candid communication, or helping their teams to become more resilient and capable of communicating in a very candid fashion. I would love to hear any and all thoughts on that.

General Stanley McChrystal: Yeah. In the military, we used to always do things called after action reviews. And they really started from the Second World War. And they came out of the realization that after a battle or a firefight, every participant had a different view of what had happened. You watch a war movie and you see a firefight and say, “Everybody saw the same thing.” No, they didn’t. They all saw where they were. And they present an account after the fact that it’s very skewed. And in many cases, it’s skewed from what they saw it and then they just get it wrong. So everybody walks away with a different set of conclusions to that.

And so after action reviews were put in place to do two things: one, to figure out what happened and then two, figure out what they should do about it next time to be better. So the first part of that was getting everybody together and going through and searching for truth, and trying to pull all the pieces out. And that was frightening to some people because sometimes you’ll find out that what you thought the reality was, was very different. And then when you start to talk about what went right and what went wrong, often it can be very, very illuminating to your shortcomings.

I remember as a young company commander, we would go into after action reviews after big training missions and some would last for hours long. And I would walk out humiliated because they had, using sights and sounds from the battlefields because they had pictures, slides and whatnot, they would point out every one of my screw ups. And they would not only point out every one of my screw ups, they’d do it in front of all of my peers and my bosses and my boss’s boss.

And so they could be very, very upsetting events and my boss’s witnesses were also pointed out to all his subordinates and that was pretty upsetting as well. So the effort was to create a thick skinned understand that everybody makes mistakes. So let’s be open enough to accept those and to accept different viewpoints. I think what we’ve come into now is a point in society that is a little bit unhealthy. In fact, I’m going to call it more than a little bit unhealthy. I teach at Yale University, and I’ve been there, I’m in my 12th year. And I will tell you that the atmosphere on the campus has continued to evolve and I don’t think for the better.

In one sense it’s better because there are people championing rights that people should have an equality and values that I think are good. But there is an intolerance for anyone whose values are different than yours. In fact, there’s an unwillingness to listen to a speaker from outside the university come and speak, that might have a polar opposite position. We talked a little while ago about the importance of the dialectic, where you get opposing ideas together. And if you only hear what you already believe, or if you protect yourself from the offensive words of somebody who violates your safe space, then I think you are making yourself more vulnerable over time.

I absolutely believe we need to, as a society, subject ourselves to all of this constantly. But we need to build up the resilience in that process to hear it, to tolerate it, to understand that things like the First Amendment had a purpose to them. They were to protect people’s rights to communicate, but they were also to build up in society a diverse dialogue that would produce a good outcome for democracy. And so I think it’s important when we talk about communication now, to understand that it’s not just what you want to communicate or just what you want to hear, it’s got to be sometimes what we need to hear.

Tim Ferriss: Are there any other ways that you might suggest or that you found to be effective for training resilience that are applicable in the civilian sphere?

General Stanley McChrystal: Yeah. There are a number of things that can make an organization communicate more or be systemically. But there’s nothing like failure to drain resilience. I remember when I was a regimental commander, we put in place an exercise which we call savage strike, if I remember correctly. And we would take a Ranger company about 150 Rangers, and we would take them from their home base, and we put them in airplanes, and we’d fly them halfway across the country, and they do a parachute assault, to go do this mission.

And the mission typically, was something like this, they’d have to go from the drop zone where they landed in parachutes to go rescue a number of Americans who were being threatened in an area in some country. And they would get there and we would orchestrate opposing forces and whatnot, role players, so that when they got there, they would secure the Americans and they would be moving to extract them, and then the enemy would attack. And when the enemy attacked, they would cause a number of casualties in the Ranger force, that would always be the dynamic.

Now the Ranger company commander’s in a position where the mission he was given was to extract the American civilians. But the ethos of the Rangers is, “I will never leave a fallen comrade to fall into the hands of the enemy.” So this Ranger company commander is in this position where to extract the Americans, he’s got to leave his dead and wounded. To leave his dead and wounded, he’s got to violate the very oath, the very being of being a Ranger. And so, I would play the higher headquarters and the company commander would invariably call in with this situation report and say, “Here’s the problem.” And I’d say, “Okay, get the American citizens out.” And they’d go, “Sir, I can’t because I’ve got my dead and wounded. I can’t leave them. I need reinforcements.” And I said, “Well, you’re not getting reinforcements. I’ve got nobody to send you.”

And so they’d be in this, it was really a moral dilemma as well as an operational dilemma for which there was no right answer. And they would get beat up and we would go and have a detailed after action review better. And they’d always say, “Well, what was the approved solution?” And my response was, “I don’t know. You tell me.” But we’re going to be in those positions because we’ve got to be resilient enough one to fail and tow, to make those damnably impossible decisions where you’re doing something you just hate doing to do something you have to do. And so, they were torn between, “Do I fail in a mission, or do I essentially break my oath?”

Tim Ferriss: I have to just interrupt for a second to ask you about the assessment. So after putting someone in a position like that, what are you looking for? Because there may be no right answer, but are you looking for speed of execution and logic/rationale behind the decision? What are you looking for? What are the positive indicators?

General Stanley McChrystal: Yeah. Because there’s no perfect answer, what I was looking for was first, does that person keep cool and go through a process? Do they first try to get external things to help them out of it, like ask him for reinforcements? Because that’s logical. So you do that until you narrow down, okay, we’ve got this really difficult situation and I’ve got to do A or B. Then I’m looking at how their values fit in, and their values in some cases are honesty and loyalty to people. And then the other is, did they go through a rational probability based outcome? Did they say, “This is the best I think we can do here, our likelihood of this being successful,” etc. Because you’re really looking for someone whose mind continues to function when things aren’t the way they want them to be?

Because they were, to be honest, there were a couple cases where the commander almost just said, “Screw it, everybody. We’re going to do a custom, we’re just going to fight and die.” And they were almost angry. They said, “We shouldn’t have been in this position, screw it, we’re going to fight and die, the hell with it.” And that may be the right answer but that wasn’t the right way it was arrived at. You know what? I wanted them to stay calm, and be thinking and look for options, and then say, “All right, this is the best of lousy courses of action,” and go from there.

Tim Ferriss: Yeah. It raises so many questions for me related to how someone could mock that in, I’m not saying they should, but this is the idea that comes to mind, mock that in an interview scenario if you’re trying to vet for important positions in a company, how do you navigate a stressful situation and do you ask them, because I know there’s a lot of criticism of stress interviews also, we’re asked to open a window and the windows jammed or whatever it might be, right? Some of those could probably end up being pretty foolish.

But is it enough to ask someone about how they’ve handled a situation like that, or do you really need to kind of put them into a situation like that in a civilian setting? I’m just having that run through my head, I don’t know if it’s even feasible to do that. But it seems like an incredibly powerful way to reveal character and behavior under stress. Have you seen any version of that implemented outside of the military?

General Stanley McChrystal: I have heard about it outside of the military but it’s hard in many cases. But I’m a great believer in role playing things. One of the things I tried to see whether it’s in an interview or in someone’s performance after then the organization, when they’re putting those decisions, do they try to dodge them? And you’ll see, they find a way to not be responsible. There’s the famous story of course, of Hyman Rickover, the father of the Nuclear Navy, and his decision making or his interview process reportedly, he put people in a chair and the two front legs of the chair were shorter than the back legs. So when you sat down, you automatically were sliding off the chair. So you had to fight to stay on.

And then he would do these really combative interviews where he would basically ask, “Why were you born? You’re not worth it.” And he asked one candidate, “All right, you’ve got two minutes to make me angry.” And apparently, the guy got up to the admiral’s desk where there was a model of the first nuclear aircraft, he picked it up and smashed it on the floor. And reportedly the admiral says, “Okay, you did it. You accomplished that.” But I do think there’s an awful lot to create in cases where people are under some kind of simulated pressure. One, they learn an awful lot about themselves.

Tim Ferriss: Yeah. For sure.

General Stanley McChrystal: As well as you learning about them.

Tim Ferriss: Yeah. I was chatting with someone I do work with and sometimes, he works with a lot of executives who are hiring, and sometimes he’s brought in, as he put it, to be the loving asshole who can apply a little bit of pressure to see what happens. Nothing too terrible, nothing too extreme, but just to see how do they handle a conversation that isn’t all rainbows and roses, right? How do they handle being interrupted for instance or having someone interject, right? Do they keep their cool? Do they get contracted? Do they start to get reactive? So it doesn’t have to be extreme certainly to try to assess those things.

Tim Ferriss: Are there any other names, people who come to mind who you think are excellent at navigating or thinking about risk? I know I keep bringing this up, in part because I just love learning of the case studies. Could be alive or dead, people you know or people you don’t know, but any other people who come to mind for you?

General Stanley McChrystal: Yeah. There are the scholars who deal with risk. And I think how we think, Daniel Kahneman, people like that, who’ve done a lot of thinking about how the human mind thinks. I’d much prefer going to practitioners who have dealt with very risky situations and looked at how they navigated them. I would go and teach this in my Yale course, Abraham Lincoln and the Emancipation Proclamation. Because when we step back with the distance of history, there was a wrong that was slavery, there was a Civil War and in the middle of Civil War, the President of the United States said, “Okay, we’re going to free the slaves.” And it was done. And of course, it wasn’t at all like that.

And so what President Lincoln was doing was dealing with risk, he was simultaneously dealing with a Civil War so the fact that they could lose a Civil War. He’s dealing with the risk that many people in the Democratic Party of the North, which were not very supportive of bringing the South to a slave free position. There were other stakeholders who politically wanted to undermine him, there were foreign powers who really weren’t excited about the South not being able to produce cotton like they had. And so, he’s trying to triangulate or balance all of these risks together, at the same time, so it’s not just knowing what the right answer is, announcing the right answer and moving forward, it is navigating this twisted journey to as good an answer as he could get. Not a perfect answer, but as good an answer as he could get.

And so when I look at that and I think of here’s a leader who is having to assess risk on a constant basis, he’s got to keep his team together, his team of rivals on his cabinet but also his larger national basis, and it was a masterful performance. And so, other than just being a smart guy and a charismatic president, he was a master, manipulator’s a negative word sometimes. But that’s what I’m really talking about of orchestrating risk.

Tim Ferriss: Yeah. Orchestrator, excellent conductor for risk factors. Well, Stan, we could go on for many hours, I can’t think of a better person to author Risk: A User’s Guide. Are there any other facets of risk or the book that you would like to explore, or any other stories you’d like to tell before we begin to come to a close in this conversation?

General Stanley McChrystal: Sure. I’m going to talk on a personal basis here because I think every leader has to identify how they deal with risks and what their own value set are. I remember in 2006, I was leading counterterrorist forces and JSOC in Iraq, and we had been at the fight for, I had been at the fight for about three years at that point, most of the people as part of the task force had been in even a little longer than that. And it was brutal combat at the time. And so, we were starting to do operations more aggressively than we’ve ever done before. We were at a point where we were doing literally 300 raids a month or 10 every night, and then occasionally, we would fight in broad daylight. And that was against star doctrine, and it didn’t play to our strengths.

And we had a situation where we got in a firefight with Al-Qaeda forces outside of Baghdad, and it became a real serious fight. And we put some, what we call little bird helicopter gunships into the fight and one of those helicopters was shot down and the pilot killed, pilots in that particular case. And the father of one of the people we lost had been an aviator, a helicopter pilot in Vietnam, very mature, very experienced guy. And he asked the question of us that was fair, he says, “What in the world was my son out doing in a middle of daylight flying a little helicopter that was designed to be flown at night for stealth, counterterrorist missions?” And we answered him, “That’s when the fight was; we needed him,” and he accepted that very graciously.

But the question we had to ask ourselves, and I did all the time is, at what point do you become hardened to risk and the cost of risk? Ulysses Grant, at the end of the Civil War, wouldn’t go to combat hospitals. He wouldn’t visit the wounded hospitals because he found it was so upsetting that he was afraid he couldn’t make the difficult decisions they had to make to get this war over. And I found myself asking myself whether I’m becoming so hardened to the risk because in some ways, the physical risk wasn’t mine, it was being borne by other people. And had I become so close to the problem that solving this problem, defeating Al-Qaeda in Iraq, was overwhelming for me? And what was the risk to the larger national policy and all that sort of thing?

And it’s only almost like you’re in a bar with your brother and you get in a fight and at a certain point in the fight, you need your brother to pull you out of it. You may be losing, you may be winning, either way, you need your brother to pull you out of it. And I’ve got four brothers, so that was very important. But I think we all need to think about risk that way because at a certain point, your adrenaline pumps, your manhood gets challenged, any number of those things, and you will take risks and you’ll bet things that aren’t yours to bet. Or you will stay the course on things when you should have stopped simply because that’s the way it is.

And so, that’s where systems have to operate. And they almost have to, at times, to protect us against ourselves. Because we can be very good but we’re not always as good at this as we need to be, sometimes we’re just too human.

Tim Ferriss: Yeah. What will protect you? What will pull you out of the fight when you are, as we all are sometimes, our lesser selves, right? That systems are part of that answer. Well, Stan, thank you so much for taking this time. I think it’s an important, couldn’t be a timelier message and more than a message, it’s a toolkit, it’s a set of frameworks and approaches that have been tested in the field and stress tested. So I think this is an incredibly important work.

And the book, just to remind people, the title is Risk: A User’s Guide. You can find General McChrystal online at His name is probably misspelled as often as mine, so I’ll say it one more time M-C-C-H-R-Y-S-T-A-L I’ll link to all of these things, everything we’ve talked about in the show notes at 

And for everybody listening, until next time. Thank you for tuning in.

The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 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.

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