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Home > Analysis > Intelligence Gathering Tools and Analysis, Strategic Thinking and Uncertainty

In May of 2020, OODA CTO Bob Gourley had an OODAcast conversation with Carmen Medina, who served 32 years in senior positions at the Central Intelligence Agency, most of which focused on one of the hardest tasks in the community, that of analysis.

We continue our effort to underscore certain patterns and themes found throughout the OODAcast library of over 80 conversations with leaders and decision-makers, on topics such as leadership, empowering a team, finding the right people, clear decision-making while operating in a low information environment, the qualities and best practices of a true leader,  the future of intelligence, the future of cyber threats and cyber espionage and strategic action.

Bob and Carmen discuss information-gathering and intelligence tools, uncertainty, and decision-making.  The conversation is also interesting as a time capsule from the May 2020 timeframe of the pandemic:  before the vaccine, before variant surges, before the 900,000 plus death toll.  It is interesting to read now  – with the knowledge of how the uncertainty at the time Bob and Carmen spoke has now played out.

Early Career

Bob Gourley:  You spent a career in analysis in the intelligence community at the Central Intelligence Agency, and you worked in several positions there, including the head of the Strategic Assessments Group. And you then went on to become the Deputy Director of the Central Intelligence Agency for Analysis.

Carmen Medina:  Correct.

Gourley:  And to me, I was in the Intel community, in or around it most of my life, and I always regard that position as the number one analysis position in the community. You’re a leader, a manager, a thinker, a trainer and after great work there, you went on to teach in the Intel community at the Center for the Study of Intelligence.

Medina: Correct.

“I was sort of forced into this position of being a heretic at the CIA, arguing for something that the organization didn’t believe in.”

Gourley:  And since then, you’ve been a writer, you’ve written books, including A Rebel At Work, which is a handbook for leading change and a follow on to those dispatches from rebels at work. You’ve also consistently been writing on your blog @recoveringfed.com. You’ve worked in industry, with Deloitte and your own practice. And did I leave anything out there, Carmen?

Medina:  Well, the only thing I might highlight is why or how it came to be that I had expertise on being a rebel at work. And that’s when I was at the CIA from the mid-1990s when the internet arrived, I thought, man, every knowledge organization is going to have to change to adjust to this new reality. And the CIA was slow to pick up on that. And so, I was sort of forced into this position of being a heretic at the CIA, arguing for something that the organization didn’t believe in. And I made all the rookie mistakes. And that’s what led to the writing of the book Rebels At Work.

“…the strategic leadership positions are sort of suited to my strengths and hid my weaknesses.”

Gourley: Rookie mistakes like what?

Medina:  Like, well, the first most obvious one is not realizing that by arguing for the internet and its importance at CIA, I was arguing against prevailing theology. So, the CIA is about secrets and controlling information. And the internet, particularly in the 1990s when it came out, was about open information and no secrets. And if I had just put two and two together and got, okay?  – I can see why the CIA is not going to be receptive to this, I think I would have proceeded differently. but I did not make that connection until after the fact, which I’m embarrassed to say.

Gourley:  By the time I met you, you were already very senior and in my few interactions, you were incredibly polite, friendly, always smiling. And I tell you when I was a more junior person in the community, I didn’t have that together. And for some reason, too frequently, I would be the skunk at the party. And I know that’s the wrong way to be a rebel at work.  Were you are always so polite and friendly and courteous?

Medina:  Well, you know, that is a good question. I mean, I’m an introvert anyway, that’s my natural disposition. And I try to be careful. I think my sense of humor is always on or my sense of whimsy or the absurd, but when I was trying to make progress with these heretical ideas at the CIA, I became less nice and, you know, ended up making enemies or alienating people that I should not have alienated.

But I really enjoyed being a strategic-level leader. I think this is going to sound pretentious or obnoxious, but I really do think it plays to my strengths, which is, I like to think big thoughts, but I’m not good at the details.  I’m not particularly good at the execution of it. And so, the strategic leadership positions are sort of suited to my strengths and hid my weaknesses.

“A bias that I think has affected us during this COVID-19 period is this bias I think almost all of us have, which is to just assume that worst-case scenarios do not happen.”

Gourley: Carmen, you write about thinking and how we think, and you have been doing that for years ever since you transitioned out.  Recently, you have been writing about how we think in the context of the Coronavirus, in fact, two blog posts, in particular, a part one and part two on that topic. And I want to ask for a little more context around that, this concept of cognitive traps, right? What did you mean by that?

Medina: I think that we all have a, for lack of a better word, neurological disposition. I mean, we are learning a lot about how our brains are wired and then our, of course, our experiences affect us in how we think. And so, we all have tendencies, and it is very important that we no one, nobody can be objective the idea, the goal of a perfectly objective analyst is just fallacious. It is a dream. The best we can get is to try to achieve objectivity about our own biases, you know, to come to understand them. So, I have a bias that I am an optimist by nature, and it is very hard for me to accept pessimism. For example, something I got wrong: I just did not see how Yugoslavia was going to break up in the early 1990s. I could not figure out why people who had McDonald’s would fight a war.

That was definitely my pessimism bias showing up. A bias that I think has affected us during this COVID-19 period is this bias I think almost all of us have, which is to just assume that worst-case scenarios do not happen. You know, worst-case scenarios are unlikely. And in reality, the impact of a particular situation is independent of its probability. So, there are two variables that are independent of each other. And yet in common thinking, well, not just in common thinking among policymakers, it is very normal to think, oh, well, that is the worst-case scenario, so it is not going to happen. And that is what happened with COVID-19. People could see what was happening in China and then Italy, Iran, and then Italy, and for reasons that completely escapes me, they assumed it would not occur in the United States. Now in retrospect cannot really explain it, but we lived through it. So, we know that happened, right?

“…we are really in danger of falling into a cognitive trap when something happens that breaks the norm.”

Gourley:  In fact, early on  – way before Italy, before Japan, before South Korea – there was Wuhan. And you were looking at that then and thinking something was up?  You know, it reminds me of so many cases from history where people have gotten the information they should have had for a warning of some event. And they didn’t take the event or didn’t follow through. And one is the famous Soviet spy, Richard Sorgi, who was in Japan, who some people say was the greatest spy. And he got all the information available  – through his network in Japan saying that the Nazis were going to invade the Soviet Union – got that all the way to Stalin, who just disregarded all of it.

Medina:  Right. Another good example of it in my professional career was when Saddam Hussein invaded Kuwait. And people had picked up using satellite imagery, all these Iraqi movements. And I remember one person trying to explain that away by saying “oh, it’s just for show”. And I’m thinking, well, it’s only for show, if you have a satellite to see it, otherwise it’s just stuff being done in the desert where nobody is seeing it.  So, it just doesn’t make any sense. But again, I think, we are really in danger of falling into a cognitive trap when something happens that breaks the norm.  And we have norms for a reason, that’s how the world normally operates. We don’t normally have pandemics and we have a tendency – it is another way of saying the worst-case scenario is viewed as unlikely. We tend to just wave away evidence of norm-breaking: “Oh, that’s not happening”.

“…actions reveal intentions and motivations – that when someone does something, they are doing it for a reason.”

I recall being at a conference in mid-January, January 16th in Minnesota, and there was a contingent of attendees there from Seattle. And I was thinking, golly, if the virus or when the virus comes to the United States is going to be a likely initial port of entry because of the Asian American connection. And of course, it was the Lunar New Year. So, there was a lot of travel going on. And when I looked at what was happening in Wuhan and that the Chinese government was closing down, essentially, it’s Chicago, right? It is a major industrial city – closing it down and closing Lunar New Year, right? Stopping the celebrations. I was thinking, wow, why would a government do something like that? That is, for the Chinese communist party whose legitimacy depends upon economic growth. It just made no sense to me. This is one of my favorite heuristic devices as an intelligence analyst: that actions reveal intentions and motivations – that when someone does something, they are doing it for a reason and try to figure out what the most likely reason might be.

“We have to be humble…we don’t know what percentage of reality any of those things represent. So, our tools are incomplete. Our knowledge is incomplete.”

Gourley:  This is fascinating. This also relates to another topic you wrote about, which is tools and the fact that, like those satellites looking over the desert, if you did not have that tool, you would not have that data. Right. You also write about the fact that knowledge tools really informed decision-making.  What do you mean by that?

Medina:  Everything that we know, and we forget, this is a function of our tools for knowing, and our tools are always incomplete.  You know, only an omniscient seeing God has a complete set of tools. So right now, our tools for understanding the virus are models, but these models all have biases built into them based on the assumptions that the modelers make to create the model. And so, we must be very humble. We must know and understand that our knowledge is always incomplete because our tools are always less than perfect.

And for intelligence professionals, this is particularly true because our tools, secrets, and intelligence collection are naturally biased, right? They’re naturally biased because we pretend that secret information is better than open-source information. They are naturally biased because we can only see what the satellite sees or only hear the communication that’s intercepted. And we don’t know what percentage of reality any of those things represent. So, our tools are incomplete. Our knowledge is incomplete. It only reflects a certain unknown percentage of reality. And yet we must make decisions based on that.

“…it is difficult though because policymakers crave certainty, they crave certainty and assurance, right?”

Gourley:  So mental models are also tools. And I think maybe that is our great hope, if there is training going on because obviously, we can study Daniel Kahneman, for example, Jay Richards, Richards Heuer, all that great work that you did at the Center for Intelligence.  Maybe our hope is that we can teach analysts to understand all these biases and knowledge gaps and problems with tools and improve the outcome.

Medina:  Yeah, absolutely. I think that a great analyst is really, in a sense, a philosopher of knowledge in that he or she spends a lot of time trying to understand the limits of what is knowable, right?  And it is difficult though because policymakers crave certainty, they crave certainty and assurance, right?

“What are all the new things we can do now?”

Gourley:  You know for the CEOs and our community, that’s what they crave. Also, they like to have a nice predictable pipeline of coming business and they want a good accurate assessment of their competitors. And now in this pandemic, you know, even though it could never be truly accurate, and I think most good CEOs are good at ambiguity anyway, but now it’s all ambiguity.

Medina:  Right. Exactly. You know, we don’t know whether it’s going to be a sharp V or a very long and shallow U recovery. We don’t know if there’s going to be a second wave. We don’t know if we are going to have a vaccine. We just don’t know. And so therefore we must try to assume the posture that offers the most resilience.  And if you’re lucky, and I think some companies are doing this, if you’re lucky one of the best ways to grapple with uncertainty is to create a new reality for yourself to kind of create this new way of doing things that takes advantage of the uncertainty.

And I can’t think of them right now, but I think there are some companies that are trying to figure out how to do that. So, for example, if you embrace working from home rather than see it as a necessary nuisance.  What are all the new things we can do now? How can we cut costs if everybody’s working from home?

“I think that that is one of the best practices for dealing with uncertainty.  You can’t stop creating.  You must create an experiment with lots of different things. Because some of them will stick.”

Gourley:  One of the new realities for my company OODA is this very podcast because Matt Devost and I were planning our big conference in March. And we were so excited about that. And about two weeks prior, we realized that this pandemic is coming sooner, versus later.  We always knew it was coming, but we knew we had to cancel.

Median:  No, you guys made a very good decision.

Gourley:  Well, thanks. Thanks. And yeah, as soon as we did, we realized hour after hour, that it was the right decision. But then we had to think, you know, what do we do? Well, we want to keep interacting with our community. We want to do these kinds of video things. Or we invite thought leaders like you to interact with the community and it would not have been done except for the pandemic.

Medina:  I think that that is one of the best practices for dealing with uncertainty.  You can’t stop creating.  You must create an experiment with lots of different things. Because some of them will stick. Some of them will work. Some of them will not and that is okay, but some of them will.  And I think if you keep churning if you keep moving your legs, you know, keep your legs moving. I think that you can you hit, you stand a better chance of prospering during this time.

“I can spend a hundred percent of my time looking for off-beat information. But I think that anybody should say, okay, 20, 30% of my time, I’m going to go off the beaten track.”

Gourley: The final question is about your sources of information. Any advice you have for what I should be reading or what are other readers should be reading or viewing or thinking about with books or good articles or sources?

Medina: Yeah I don’t tease actually. But people think I’m teasing when I say that Twitter is my knowledge strategy, and I really value that stream of random information that I get through Twitter. And what it does is direct me to sources of information that are more likely to have unusual off-beat early reports on important developments. I don’t know if you read, I think it was the health minister of Taiwan and Taiwan’s done a great job on the pandemic, how they first got wind of it through a Reddit post. And then the next day they said, “okay, something’s going on.” And we need to start doing, getting prepared. Well, I don’t do Reddit a lot, but I do look for quirky and different things. I think it’s okay to follow the mainstream media, but they are always three or four days behind the times on important stories.

Just recently I came across a resource, a scientist type I think, who is blogging on a science platform – who is giving kind of day-by-day reporting on vaccine development. Very technically difficult for me to make sense of, but I know that this is really ground truth in a way that the diluted stuff I get through the media is not, so I like to look for the offbeat. I don’t have a job with any organization, so I can spend a hundred percent of my time looking for off-beat information. But I think that anybody should say, okay, 20, 30% of my time, I’m going to go off the beaten track. What I often do is, when I find an interesting article from one source, I put it on my reading list, and I just keep going back to it on a regular basis to see what other new and different things they are recording.

Watch or Listen to the Full Interviews:

OODAcast – A Conversation With Expert Practitioner of Analysis Carmen Medina

Further Resources:

Carmen’s Blog: Intelligence | RecoveringFed

Thinking in the Time of the Coronavirus Part One

Thinking in the Time of the Coronavirus Part Two

Rebels at Work: A handbook for leading change from within

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Russia’s Long Game, Leadership Lessons, and Learning from Failure (Rob Richer)

Nate Fick on Company Culture, the Cybersecurity Community, Endgame/Elastic and Emerging Cyber Threats (Part 2 of 2)

Nate Fick on His Early Career, Writing ‘One Bullet Away’, The Stoics and Dynamic Leadership (Part 1 of 2)

John Robb on Hyper-networked Tribes, Digital Sovereignty, Digital Identity, Digital Rights and “The Long Night” (2 of 2)

John Robb on the Early Internet, Frameworks to Drive Decision Making, Network Tribalism and Emerging Threats (1 of 2)

Chet Richards and the Origin Story of The OODA Loop (Part 1 of 2)

Chet Richards on Applying OODA Loops in Business (Part 2 of 2)

Dan Gerstein and Lance Mortlock on Technology Futures and Scenario Planning

Ellen McCarthy and Kathy and Randy Pherson on Intelligent Leadership and Critical Thinking

Richer and Becker on Domestic Terrorism, Cyber, China, Iran, Russia, and Decision-Making

Omand and Medina on Disinformation, Cognitive Bias, Cognitive Traps and Decision-making

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Daniel Pereira

About the Author

Daniel Pereira

Daniel Pereira is research director at OODA. He is a foresight strategist, creative technologist, and an information communication technology (ICT) and digital media researcher with 20+ years of experience directing public/private partnerships and strategic innovation initiatives.