Start your day with intelligence. Get The OODA Daily Pulse.
Informing your decisions with actionable intelligence
Start your day with intelligence. Get The OODA Daily Pulse.
Informing your decisions with actionable intelligence
In February of 2021, Matt Devost spoke to Rob Richer, a highly regarded advisor to international executives and global government leaders including several heads of state. Rob has a well-informed perspective on international risks and opportunities and an ability to analyze and distill observations in a way that is meaningful for your decision-making process. Rob Richer retired in November 2005 from the Central Intelligence Agency as the Associate Deputy Director for Operations (ADDO). Prior to his assignment as the ADDO in 2004, Richer was the Chief of the Near East and South Asia Division, responsible for Clandestine Service Operations throughout the Middle East and South Asia.
Mr. Richer has been awarded numerous awards and commendations from several foreign governments. Additionally, during his Agency career, he has received commendations and awards including the Intelligence Commendation Medal in both 1993 and 1996; the Director’s Award in 2004. In March 2006, Mr. Richer was awarded the Distinguished Career Intelligence Medal.
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.
In light of the conditions in Europe, this portion of the conversation is timely, covering topics such as Richer’s time as head of CIA Russian Operations, his perspective on U.S./Russian relations (especially the role of cyber), leadership, the role of failure, and decision-making.
“after that tour, I was asked to be the Associate Deputy Director of Operations, which I took until I retired in 2005.”
Matt Devost: Let’s start with your career progression. Can you step us through where you started your career, including the military and the trajectory up into the CIA and what you did after you left the intelligence service?
Rob Richer: Sure. 1971, I enlisted in the Marine Corps. College was not on the agenda for me. I didn’t have the grades and my family could not afford it. I went in the Marine Corps as a private and after I got out of boot camp in ‘72 I progressed through the ranks until I was made Sergeant in 1976. I was picked up for a program called MECEP in the Marine Corps, which is the Marine Corps Enlisted Commissioning Program. And it takes non-commissioned officers who the Marine Corps believe have the potential to be officers and send you to college while staying on active duty and you get your degree and your commission. It took me two years to get through college. I went to the Citadel in South Carolina as a Marine, not as a cadet, graduated in ‘78, was commissioned as an officer in the Marines as Second Lieutenant.
I went into the infantry where I stayed, progressed in the Marine Corps as an infantry platoon commander, infantry company XO, and infantry company CO of a weapons company. And then applied for and was recruited by the CIA in 1983. I went into the agency, went into the career training program of the agency, which at that time was 18 months, upon which I was assigned overseas in the Middle East. I progressed from Middle Eastern tours in 1985 through 1995. And then I came back from the Middle East, and I was assigned as Chief of Russian Operations at a time when we were dealing with the aftermath of the Aldrich Ames/Russian penetrations of the CIA. And because I had no experience against Russians and was not thought to have been compromised, I was brought into to run Russian operations.
I did that through 1998 and then went back overseas to the Middle East. Returned in 2001. The summer of August of 2001, took over human resources for the clandestine service responsible for recruitment, training new officers, all career path interests, promotions, all the things that HR does for a service. That was my out-of-body experience. I did that for a year. And then with the Iraq war looming, I was asked to take over as chief in the Middle East, division chief of Near East division, which manages 20 plus stations in 20 plus countries throughout the Middle East, from North Africa to The Levantine – all the way to South Asia. Then after that tour, I was asked to be the Associate Deputy Director of Operations, which I took until I retired in 2005.
I took a job as a Vice President of intelligence with Blackwater. That is where I met Matt. We had a great time together, both with Blackwater, and then moving on to Total Intel – which we ran together. I left Blackwater and over the years since then, I have been the COO of two different companies. And I am right now engaged with boards and advisory groups and continue to do Middle East travel – I did until COVID, almost monthly -and continue to maintain relationships in that part of the world. So that is my career in a snapshot.
“So, after I got through the period where I thought I was the smartest and best-looking case officer and spy ever, I got to the point where I understood that you know what: I am much better when I talk to other people.”
Devost: We call this the OODAcast, based on John Boyd’s OODA loop, which I know you are familiar with. I know that Marines tend to have an affinity, despite the fact that he was an Air Force Colonel, for decision-making. And I know from experience that you have a very acute ability to make good decisions and provide good advice. So, I would love to get your perspective: over the course of your career, what were some lessons learned along the way that contributed to the way that you make decisions or the perspective that you bring to the decision-making process?
Richer: Well, I think that the greatest experience and lessons I had in terms of decision-making, good or bad, was being wrong and that wrong had direct ramifications or that wrong caused a loss of life or a loss of a job. So, making mistakes in many ways has been the best educator I had in terms of good decision-making. And what I learned in many cases because I had the tendency to leap to a decision and to want to move aggressively and not tolerate long discourse – I had some great people work with me on that – whether it was as a Captain in the Marine Corps, a more senior rank, whether it was a mid-career officer in the CIA – people who said: “Look, you have potential Rob. You are doing well. You have good intuition. Take time. Pause. Think.”
So, one: I like to reflect on what you are going to say and what you are going to do. Two: do not believe you have all the answers. Three: listen to other people. I have become a firm believer of what General Mattis talked about – being a servant leader. And he is talked about that since I knew him, gosh, 25, 30 years ago – which was that a servant leader serves the people he works with. Ultimately, he is responsible for the decision. But if he is going to make a decision that is going to put people’s lives, livelihoods, families at risk, you listen to them. So, after I got through the period where I thought I was the smartest and best-looking case officer and spy ever, I got to the point where I understood that you know what: I am much better when I talk to other people.
And I think the place where I learned the most was when I became Chief of Russian operations. I was pulled back from my assignment in Oman. I just got a note saying, please come back to Washington. I had no idea I was coming back to Washington. And I was not sent to my head office, which was the Middle East. I was sent to the 7th Floor to the Office of the Deputy Director for Operations, now the Director of the Clandestine Service, who said to me: “We want to consider you for a new job, but we need you to get an FBI polygraph first.” And until that time, all my polygraphs had been CIA, because we would do our own. So, I was sent downstairs. I was polygraphed twice. I had no issues.
“A great lesson for me is: failing–combined with the understanding that I do not have all the answers and then soliciting other people’s input–but then still realizing: ultimately the final decision rests with you.”
And the focus was solely on my contacts with Russians or Soviet Russians at that time. I went back upstairs, and I was offered the job to run Russian operations at a time when we were reeling from what Ames had done to us. And while I was in Russian operations, we caught Nicholson, a CIA officer who was a Far East Officer who was spying for the Russians, and a few others in the U.U. Government. But during that period, I walked in as a Middle Eastern hand who had done well in his career, to an area with Russian experts – thinking that what I learned in the Middle East translated to what I could do and understand Russia. and what I learned very quickly from some really good analysts and officers and admin people was, I didn’t know squat about Russians, except what I had read maybe in a book.
And what I learned was that everything I was saying – that they are nodding yes to – they are walking out the door saying, “let’s just try to fix it without him knowing it.” So after, I had a great deputy who is still in service so I cannot mention her name – but I had a great deputy. And that deputy came into me one day and said, “Hey, boss, let me give you some thoughts on what we are doing together.” She handled it very well. And I learned that when we started having meetings, talking about a Russian operation that was going to be a great risk in Moscow or Russia or an approach to someone or looking at a spy in our own building or with the FBI, the team effort was a hell of a lot better than just a Rob effort.
A key to growth as a person is getting someone’s feedback. And I think, Matt, you and I did when we were looking at what we were going to do at Total Intel we, it was a joint leadership role, I mean you did day-to-day management of everybody, but the point was: we talked to decisions. You were always great about coming in and saying, “Hey, Rob, you know, I don’t know if we should go this way, or this makes better sense” – particularly if it had to do with technology. And you are the one who taught me how to use an Apple computer. My point is: A great lesson for me is failing, combined with the understanding that I do not have all the answers, and then soliciting other people’s input. But then, still realizing: ultimately the decision rests with you.
“[The January 6th Riots], and what we have to work on with the Proud Boys and the conspiracy theorists, is going to occupy us for such a long time…we may even get farther behind [on Russia].”
Devost: You raised a question about the Russians and, you know my perspective, especially given my focus on the cyber domain, is that we are being outplayed by the Russians on the global stage. You mentioned that they, despite not really being a superpower, have this sphere of influence in the Middle East. What is your perspective on kind of the power structure between the US and Russia right now?
Richer: You know, a lot of my colleagues will tell you that they have a hold on some aspect of this US Government. But look, the Russians play a long game – as the Chinese do. The Russians understand that actions that they can influence today may not be as good as getting ahead of the game and being able to influence actions down the road. We have not touched and addressed the Russian hacking of late 2020 in any way, except the intelligence community has delivered an assessment that it was the Russians. Experts in your field have said it was the Russians. And they have gotten away with it. You know, we have done some sanctions on people. But you know what, we have not turned a loose retaliatory cyber-attack, nor have we actually made them pay for what they did.
And that flows through the last four years [2016 – 2021] where Russia had Carte Blanc in Syria in working against our Kurdish allies in expanding its relationships in Turkey and with Saudi Arabia. I mean the Russian intelligence, military intelligence and civilian intelligence, the FSB and the GRU, are everywhere in the Middle East right now, trying to create partnerships with people we have traditionally worked with. So, look, we lost four years of confronting Russia and keeping them in their place. We are all kept “in place” as countries. But “our place”? We let go away. Whether it is in the Middle East, whether it is in the EU and whether it is a major transnational and international issue that is critical for us. So ultimately, Matt, we have up.
We are going to be playing catch up and it is going to be longer than just a couple of years because now that these relationships were established by the Russians, with these key partners in the Middle East, they have proven what they can deliver. You have a leader in Russia, Putin, who is either going to be Prime Minister or President, back and forth, for the rest of his life – and who is not afraid to take out their dissidents, kind of like the Saudis did with Khashoggi. So, he is going to stay in power.
They are going to continue to play the soft power game against us because they are winning it. The new [Biden] administration – from the people I know who are going in there with some of the intelligence professionals- we will move on to it. But I think that the domestic impact of what happened last week [The January 6th Riots] and what we have to work on with the Proud Boys and people like that, the conspiracy theorists, are going to occupy us for such a long time – that we may even get farther behind [on Russia].
“We did it to ourselves. When you shoot yourself in the foot, you cannot go blaming someone else. They may have given us the gun, but we put the bullet in it, and we shot ourselves.”
Devost: Yes. Yeah. It speaks directly to some of the writing that I have done. And I know you have seen it, with regards to the cyber ops, the domestic unrest serves the Russian purpose of preventing us from stepping back into that void. I should not call it a void because we step back, they step in. and there is no stepping back in it. You must work your way back in, right? It is a contested ground now at this point. And I do feel like part of Putin’s long-term strategy was to create as much societal unrest as possible in the United States to distract us from that overseas mission. So, you know, mission success in that regard, I think if I am Putin and I am keeping a checklist, he won that battle with regards to distracting us – at least over the short term.
Richer: I think, Matt, you are exactly right. I think all our enemies – China, Russia, all the people who are against what we stand for – won with what happened the last couple of years. And by that, I mean the Russians and the Chinese, yes, they played games with the election process if they could with influence operations, but they really did not have to do a whole lot except add to or push forward our own dialogues in this country. So, you know, one of the types of persons we recruit at the agency are called agents of influence. And these are not people who know the secrets, they are not the people who can steal code. They are someone that you stroke and get to where they will do policy or other things on your behalf or in the support of your own policy objectives.
So, in President Trump, and I do not believe President Trump works for anybody. I think he works for himself. So, I do not think he is a Russian recruited agent of influence. I do believe though I could claim him as an agent of influence because what he did played into what the Russians and the Chinese wanted – which is to diminish America standings in the world and to humble us a bit. And we are humbled. When you look at our standing, and you read the foreign press as I do, I get a summary every morning, we are dismissed out of hand. We are not a laughingstock: our military is still the best military in the world. But the people who have done our policies and the direction of this great country are directly impacted – and Russia could not have done this without us letting it happen and fueling it. So again, I take your point. I agree. They played games – but they didn’t have to play a whole lot of games. We did it to ourselves. When you shoot yourself in the foot, you cannot go blaming someone else. They may have given us the gun, but we put the bullet in it, and we shot ourselves.
Devost: Yeah, no, I agree. And we have referred to it. Neil Pollard and I wrote about it a few years ago as the trust wars, right? It is just a matter of diminishing trust in our institutions. Once that is gone, we will fight amongst ourselves. And you know, that is just the perfect exemplar of that.
“Come in and brief me succinctly, and I’m good at bullet point. Speak truth to power.”
Devost: I would love to get your perspective on leadership as well. You have worked with a lot of great leaders. Are there any stories that come to mind or leaders that you encountered, that serve as an example or mentor for you and for your style?
Richer: Well, I can name a few. So, for one, Bill Burns, who has been nominated as the CIA Director. So, Bill was the Ambassador in Oman. I was the Chief of Station and for us, that is a pretty heady place. The agency has a unique role in that part of the world and he and I were together at a time when King Hussein was passing. And there was an unsure line of succession in the initial months. So, this would have been the end of ‘98, early ‘99. And he and I were both dealing with the leadership circles, or want to be leaders, in that country. At the same time, we were both reporting back to Washington in our own channels, which are not the same, and I remember him reaching out to me and saying “Rob, I know you have your own relationships, but we need to coordinate and, and I will show you what I write if show me what you write.”
And so, he and I almost every night there for about three months, we would do our rounds – the meetings and my meetings for what we do in the organization are at night, late at night – and we would meet up at his official residence, his home, at 11, 12, 1 o’clock in the morning. Compare notes, and we would send our stuff in and then be back in the office at seven in the morning. But he had the most patient leadership style I have ever seen. And watching him manage a country team in a time of transition – managing USAID, Peace Corps, US Information Services, and then, you know, working with the huge US military relationship there. And then hoping that the CIA guys were not trying to do something behind his back. He was an unbelievable leader.
Burns was one of the first mid-generation leaders to me in terms of my career and bringing me along. Another person for me was George Tenet. So, when I came in to be chief of Russian operations, I was a junior-senior officer. I had just made the senior ranks. And he brought me in and told me “Come in and brief me succinctly, and I’m good at bullet point. Speak truth to power.” And he was great about that. “Tell me what you think”. I remember I sat in the first meeting with him, and I was trying to hedge a problem and he looked at me and he said, “Rob, just tell me, good and bad. Just give me the details.” It taught me you do not have to fluff anything that it is much easier to make a point and not worry about politics.
“…you have yet to figure out your capabilities. Look at yourself and I’m going to challenge you.”
George Tenet was great for that. Then over the course of my career, there are some great Marines General Mattis, General Conway, who I had in different roles. Sergeant Armell when I was a young PFC in the Marine Corps in 1972, told me that I could do more with myself than I was trying to do.
I remember him bringing me into the office one day. He said, “Look, you graduated from high school.” Now in 1972, it was a minimal percentage of us graduated from high school in the Marine Corps, as it was just at the end of the Vietnam war. And he says “you graduated from high school, and you had one quarter” – I had one class at Oakland Community College in Michigan – “you have one class in one quarter at one community college, which is more than a lot of our officers at right now. You are not trying hard enough.
He said: “I’m a fat Sergeant” – he wasn’t fat. He was a Marine Sergeant – “I’m a fat Sergeant. And I’ll always be a Sergeant you said, but I know my capabilities and I’m good at it. He said “you have yet to figure out your capabilities. Look at yourself and I’m going to challenge you.” And he challenged me, challenged me every day, challenged me on what I was doing in the field, challenged me to go to promotion boards to get promoted meritoriously to corporal and sergeant by learning my job. So, I was challenged to be a leader I was developed as a leader, and those people were critical to moving me on as a leader.
Russia’s Long Game, Leadership Lessons, and Learning from Failure (Rob Richer)
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
Decision-Making Inside the CIA Counterterrorism Center Before, During, and After 9/11
A CIA Officer and Delta Force Operator Share Perspectives on 9/11
Now more than ever, organizations need to apply rigorous thought to business risks and opportunities. In doing so it is useful to understand the concepts embodied in the terms Black Swan and Gray Rhino. See: Potential Future Opportunities, Risks and Mitigation Strategies in the Age of Continuous Crisis
Use OODA Loop to improve your decision-making in any competitive endeavor. Explore OODA Loop
The greatest determinant of your success will be the quality of your decisions. We examine frameworks for understanding and reducing risk while enabling opportunities. Topics include Black Swans, Gray Rhinos, Foresight, Strategy, Stratigames, Business Intelligence, and Intelligent Enterprises. Leadership in the modern age is also a key topic in this domain. Explore Decision Intelligence
We track the rapidly changing world of technology with a focus on what leaders need to know to improve decision-making. The future of tech is being created now and we provide insights that enable optimized action based on the future of tech. We provide deep insights into Artificial Intelligence, Machine Learning, Cloud Computing, Quantum Computing, Security Technology, Space Technology. Explore Disruptive/Exponential Tech
Security and resiliency topics include geopolitical and cyber risk, cyber conflict, cyber diplomacy, cybersecurity, nation-state conflict, non-nation state conflict, global health, international crime, supply chain, and terrorism. Explore Security and Resiliency
The OODA community includes a broad group of decision-makers, analysts, entrepreneurs, government leaders, and tech creators. Interact with and learn from your peers via online monthly meetings, OODA Salons, the OODAcast, in-person conferences, and an online forum. For the most sensitive discussions interact with executive leaders via a closed Wickr channel. The community also has access to a member-only video library. Explore The OODA Community
About the Author
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.
Informing your decisions with actionable intelligence
Informing your decisions with actionable intelligence