Gary Harrington on the OODA Loop and Leadership Lessons from Delta Force to the CIA

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Hi, I'm Matt Devoe. Welcome back to Oodacast. Today we have Gary Harrington joining us. Gary has a very interesting career trajectory that includes media, intelligence community and then as a private security consultant. So Gary, thanks for joining us today.

Hey, thank you, Matt. Good to see you.

So why don't you step us through kind of your background, you know, what was your career progression?

So my career progression was stay somewhere so you could piss people off enough and then go somewhere else. I think I was a person that was always seeking, always hungry, always wanting a new adventure. So I got commissioned in the Marine Corps as an infantry officer. And after a year of doing that, I heard about this reconnaissance stuff. So I tried out for that, made that, and then I spent the next year and a half doing that. Made captain in the Marine Corps, got promoted or made captain and then they said, hey, you're gonna have to go take like an admin job for a few years. And that just didn't sit with me. So I resigned from the Marine Corps and enlisted in Special Forces. Figured well, hey, this way I can spend a whole career having adventures and not have to worry about doing admin. And then I spent next 20, almost 20 years Special Forces. I was in 7th Special Forces Group Delta as an assaulter and then 5th Special Forces Group up through 9, 11 and the beginning of Afghanistan. And then after that, towards the end of my military career, I started working on some projects where I coordinated with the agency and liked that pretty well. And I wound up being loaned from the army, detailed from the army to the agency after Afghanistan for some other stuff around dealing with Iraq. And then it seemed like a good fit. So, you know, on a Friday I retired from the Army. On the next Monday I was at the agency. So then I spent 11 more years in the agency and then retired. Thought it was time to do something other than government work. So, so I retired, took an early retirement from the agency. And then, you know, after that, you know, I think like everybody else, like government fits in with government contracting. I looked at government contracting. I had a bit of a well known reputation within some of the circles, so I got some security work pushed, sort of pushed at me. The former director of the FBI recommended me to his, his former boss. So, you know, we did that for a while, but those, those jobs didn't really suit me. I mean security, it's just hiring people and getting contracts that didn't really suit me. And the same with government contracting. I like to plan and to work, but then it's really about percentages and hiring and that. So it just didn't suit me. So now I prefer to consult with people because I like helping individuals and families. It feels like I can offer expertise and experience from things I learned over all my years in undercover and in combat that help people's everyday lives. And you know, that's, that gives me a lot of satisfaction. And especially, you know, in recent times it seems like more and more the everyday citizen here realizes they need some of that. So it's real satisfying to me.

Excellent. I feel like we glossed over a major segment of your career. 20 years in the Special Forces, including Delta Force. Are there any operations from that timeframe you can step us through that served as kind of a great lesson learned for you or you came out of that with some sort of leadership skill or insight, you know, that you found valuable through the rest of your career?

Well, you know, you learn more from your mistakes. So I think I was lucky enough to survive some mistakes. I'll tell you a humorous one was prior to the Iraq war, I was in the run up to that. I would take a small team of Kuwaiti people that were not trained, they weren't military people, and I would go into, you know, some bad guy territory and a couple nights a week and you know, I was the, the expert and everybody else were, didn't know what they were doing. So I thought I was really.

You.

Know, I didn't, I felt I was invincible. And one day there was the border between Kuwait and Iraq has this big giant ditch. There's a big berm and then there's a 15 foot deep, 15 foot wide ditch. It's you know, anti tank obstacle. We had to, I had to get somebody back across that and you know, I had night vision goggles and I could see this peasant type guy was down in the ditch and he kept looking for a place where it was kind of broken up to climb up and he couldn't. And we sit there and I was, you're worried about an Iraqi patrol happening along. And so it just kept taking a long time. Hey, I've been a mountain climber, I've been to mountain climbing school. I can climb buildings, you know that I learned in Delta. And also I was like, hey, I can, I'll get him out and I can climb out. So I had the guys hold me by my arms and drop me down in this ditch. I go, I get the guy out and then guess what? I couldn't get out. So now time is slipping by and I'm stuck in a ditch and I'm an American, and this is before the war starts. And now I'm worried about when's the Iraqi patrol gonna come by, you know, am I gonna wind up being a prisoner here? So, Mr. I'm the expert and everybody else is an idiot. Had to sit and think for a while, and then I think finally had several guys took their boot laces off and tied their boot laces together. And I was able to use that as a, you know, they made it like a. A loop. And I was able to get a foothold from that enough that, that I got out. But it was a big lesson in humility for me because I'm like, yeah, I'm the trained expert and these are a bunch of idiots. And so I learned that, hey, that and then also preparation. So I made sure that we had the equipment to deal with climbing in and out of a ditch like that the next time. Yeah. And, you know, I think the biggest thought it wasn't about I might get killed, it was, this is going to be really embarrassing when I have to explain how I got captured by the Iraqis sitting in this hole. But, you know, but that didn't happen. So, you know, that was one lesson. Another type of lesson is in paying attention to your instincts and being aware of your surroundings. Because once in Afghanistan in early 2002, I was leading the tactical part of an agency team at that time, and they wanted to do a meeting by this. This warlord wanted to meet. So we went up in the valleys. This was just before Operation Anaconda. And it was very, you know, out high plains, high altitude. But we were out in this level plain in this little group of buildings and surrounded on all sides by mountains further out. But we were just out vulnerable in the open. And after we'd been there a little while, the guy wasn't showing up. Well, then I noticed that while it was kind of like this mud hut, outpost and store, that people disappeared. And then I started thinking there were only. I only had like six guys that were trained shooters with me. And we were, you know, we, we made a perimeter and were ready, but it was just too vulnerable and we were taking a long time. So, you know, you start getting those spidey senses, right? And that we've been here too long. And anytime you're a small team or by yourself and you go into bad guy territory, I think it's like you light a fuse that you have X amount of time that you can be there before people find out and they start assembling forces or put IEDs in or whatever to get you. So you have to be aware of what that window is. So I told the guy, I said, hey, I can give you, like, five more minutes, but we've got to pull out. And so we did that. And sure enough, after we got back, we found out that through sigint, they heard Al Qaeda on radio is talking, that they had put ambush in around part, you know, half or two or two thirds of the way around us. And we're waiting for the others to get in place before initiating an attack on us. And so, you know, the lesson from that was like, wow, you know, you do have a time window, and we're not all sneaky, peaky that you can infill somewhere and do something and be totally hidden from people. So get out while the getting is good. I think was the lesson that I learned from that.

I think that that's an important lesson when you're talking about the instincts, but then also the quickness of making decisions. That's something that I've observed even working with business leaders, is that they constantly, constantly you're trying to wait for the perfect moment or the perfect data in which to make a decision. But you reach this compression timeframe where the decision needs to be made based on the data that you had. Your instincts were firing. You understood that the adversary, when given time, will set up that kind of ambush or ied, and you made the decision that enabled you to keep the folks that were with you safe. Had you waited for, well, I want evidence of an ambush, or I want them to give me the SIGINT that the ambush is coming. Uh, once you waited for perfect data, it would have been a decision that was too late for you.

I agree with what you said. That and in life, even your personal safety, that if you're. Per se, if you are vigilant, you know, and you're. You're watching, you start picking up those early signals. And the more you're not distracted, the quicker you can pick up the early signals. And then you have an evolving matrix of decisions. And the earlier you make a decision, the less dire the consequences are. Generally, you know, I have a story that's the opposite of that, where I ignored that. You know, a few years later, I was a. I was on a corner in Kabul, and I was supposed to meet this person. So an interpreter and I were, yes, standing on a street corner in Kabul. And as we were standing there, you Know, I tried to stay kind of out of the way because clearly if somebody, anybody close would. Could see I was a Westerner. And we were certainly targets because this was in probably 26 or 7. And, you know, I was worried about somebody coming up and attacking me. So I'm scanning. You know, you scan close, you scan far. You're looking around. And I noticed that off to my left, just across the street from me, was a black Toyota sitting there with two guys in it. And it was unusual that. That a car was sitting where this was. But I looked at him, and I couldn't see anything. Then I saw a policeman across the street from him. So, you know, okay, they move on, and you keep scanning. But yet there was something nagging at me, but because unlike a few years before, in that last story, I told you I was waiting to meet somebody, and I felt that was important, that I needed to meet this person. So I stayed there. The person then came up, I took them back to talk with them at the US Embassy. But right as soon as we entered the embassy compound, literally a minute and a half, two minutes after we left that place where I was standing, there was a devastating explosion. You know, feel the ground shake. The embassy alarms went off. You know, so it turned out that that intersection where I was, there just had been a vbied there. And, you know, I waited it out. There were US Casualties, a couple people killed, several wounded. I think a whole lot of Afghans were killed and wounded. And so it turned out, and I went to the. To the embassy officials to ask that that black Toyota I saw was the suicide vehicle. And, you know, those two guys looked at me, and I looked at them, and they had to realize when they realized I was a Westerner. So I've often imagined the conversation they must have had, like, well, hey, we're supposed to kill the Western. Here's one right here. You know, we're waiting. And so it was pure luck that they decided no. And they waited, and it was a US Military convoy came along right after I left the corner, and that's what they drove into and detonated themselves. But the lesson for me was that, well, when this other incident happened, I listened to my instincts and made the decisions left in this other incident, I didn't. I hesitated, and I rationalized, you know, I have a job to do. Let me stick it out. And, you know, to be honest, I guess it's probably just pure luck that they made the decision, no, this isn't the guy we want to, you know, let's wait and see if we get something else. Yeah, but I totally gave away any ability I had to affect the outcome by not making that decision. So that, to me, goes to your point that, you know, you have. It's great to get information, but then you need to be willing to make those decisions.

Interesting. And it's fascinating. So you also have the distinction, you know, being one of the handful of people that was early into Afghanistan after September 11th. Can you kind of step us through, you know, what happened up to and leading into participating in that endeavor?

So on 9 11, I was leaving my. I was in 5th Special Forces Group. So I was leaving my house to go to the airport to go to Tampa and help coordinate a exercise with fifth Group, the Joint Special Operations Command in a foreign country, you know, working with a foreign government. And on the radio I heard the news of the first plane hitting, thought, well, wait a minute, this is odd. So it doesn't seem like it. I had a few minutes to spare, pulled into a little tiny diner, turned their TV on in time to see the second plane hit. And instead of going on continuing to the airport, I turned the other way and just went to my office. 5th Special Forces Group. And we immediately jumped in and we started planning for the invasion of Afghanistan. Then I went. I was the first of the fifth group to go to Afghanistan. I mean, to go to Uzbekistan, where we launched out of. And I coordinated with the agency. My job was to kind of facilitate the cooperation so that the Special Forces and the army could infill, resupply and support agency teams too, because there's a big, you know, cooperation between the agency and Special Forces in the early time part of Afghanistan. So I did that. And then I went in to Afghanistan in late October and wound up going to an agency team that was in Jalalabad, which wound up being the team that went up to Tora Bora. So I was with another SF team that accompanied them, and we went up and were running the ops, calling in the air for Tora Bora. And so that was interesting. And, you know, just to try to work with locals and then you have all that focus on trying to get bin Laden. But then they were squirting out and escaping at night, and we couldn't SEAL in everything. And then, you know, probably with help from the locals, you know, a lot of the people escaped. So, yeah, that. And I learned lessons there because that was Ramadan and we weren't prepared for Ramadan. And the Afghans would send soldiers forward in the daytime with no food or anything because It's Ramadan. Well, then at night, they would retreat back so they could eat and drink. And so there was never. It was really difficult to try to take ground and hold ground. And, you know, for me, the next I jumped from there to another place to go open up coast Afghanistan. And so I jumped on with another agency team, and this time we got on the ground in Coast I. I wanted to. I learned my lesson to work out the logistics so that, you know, I did stuff like build chow trucks that had the cooking and food, everything that we could take forward so that it wouldn't have to retreat. After coast I, there were two warlords that were lifelong. They had a lifelong feud. So they were threatening to kill each other. And they were more intent on that than helping us track down Al Qaeda up in the coast region. So I came up with a plan to divide them. And I and 1 had most of his tribal ties to a place called Orgun, Afghanistan. Right. Right across the Pakistani border at Waziristan. And so I ended up splitting them up and I led a team up to Orgun and where we opened up a new base in Orgun to work with that warlord. So we did that. Then I got the message to go join another agency team and in prep for Operation Anaconda. So then I did that. And then during that run up to Anaconda is when that incident where we had been partially surrounded by Al Qaeda happened. I mean, it was busy. Most teams, like if you saw that movie 12 Strong, a team comes in on top of an agency team, and they are there a week or two weeks or three weeks, and in or out I went in with agency teams, and I would stay until we brought in sf, and then I would jump on another agency team and would go in and set it up and stay until they brought in sf and then just kept repeating that. So for me, it was. I went in and stayed five months. Five months.

Wow.

So that timeframe in October, how many were involved? I know the 12 strong. Those are some of your colleagues. I remember meeting at least one of them at your retirement party from the CIA. How many of you were in Afghanistan at that point in time?

Well, you know, I think all in all, I don't know if it was about 100. And how many of those were team guys. And then, you know, you start bringing in support people, let's say ODAs in. In 2001. So we're talking, excuse me, October, November, December, there were probably like six or seven teams. And then by the time you roll to into 2002 probably another, Probably double that or you know, 20 something teams. So 100, 150 guys probably at its max. And then the agency guys and then, you know, that was the Afghanistan was known for with the agency and Special Forces. They toppled the Taliban government, you know, using a lot of air power. And so there never were, there never was a great amount of Americans. But, you know, I have to caveat that and say it's always easier to knock when you play king of the hill. It's easier to knock somebody off the hill than it is. The Taliban was not prepared for us. They weren't prepared to withstand an air campaign. So it was very easy to, you know, to be honest, to roll in and call in air and make them start giving up territory and fleeing. And I know, I remember standing at the top of Tora Bora though, and telling the guys around me that, hey, you know, they're going to regroup. This is their home. They have sanctuary all around us, that once they get reorganized and regrouped, they're going to come back and, you know, we're going to be here. It'll be. If we don't give it up in 10 years, we'll still be here. Well, now we're coming up on next year on 20 and we're still there.

Still, which is something we claimed we wouldn't do. One more question about the military timeframe, then I'd love to switch over to the CIA, but I'll say it so you won't have to. But the Delta Force teams are considered to be the most elite of the elite. So for people that are trying to operate elite teams that are kind of outside the military or what are some of the things that you think makes Delta so successful that would convey to somebody running an elite team of hackers or business leaders?

Well, you know, I think one is that you select good people to start with and you have to select people of character. A sure. You know, there's some that get through no matter what we do. But you select good people and people that have heart and drive and, and it's one of the big characteristics they look for is never give up. And the whole selection process is designed to really push you mentally and physically so that, you know, a person that's the type of person that would give up doesn't generally make it. And then once you're in, I mean, they train you very well. The operators training course is super, super intensive and you become very proficient at the skills. Yeah, in Delta you learn some different shooting Skills and other things that are more nuanced. But what you, you, it's still the basics of shoot, move, communicate, but you do them to a very high degree of efficiency. And you know, in Delta your training is very realistic. You know, there's not a lot of margin for safety. You shoot around each other when you're practicing, tossing grenades really close beside you to break contact. That's what you do in the rest of the military. You know, we have a lot of safety, extra safety built in. Delta relies on the people they recruited, the training they have and the proficiency they have to give a lot of trust to that individual. So to me, when I look at teams now and in the occasions I've had to build teams after I've tried to do that same thing, you know, I tried to equip and support people well. And I was very particular in who I recruited and threw out people that some would, that would surprise some people. Then I looked for within that organization, where's the right fit for people. Some guys might be great as a security guy, but he really sucks as an intel analyst. And so it's moving people into the right position and then, you know, giving them the freedom to make choices and make decisions and support those decisions. And you know, Delta does that with a, you know that it's an NCO driven unit which is very unusual for military, but it's done that's that way because they are so well trained and prepared.

So excellent.

That's good insight. I love the aspect of never quit.

I mean, I think that's true with some of the best hackers that I've met. You know to kid that worked for us at Fusion X Victor, that a couple months ago his wife asked him to fix an issue with her printer at the house and he just noticed that the driver installed itself. Weird. And he just dug and dug and dug until he figured out the vulnerability associated with that was one of those things. It doesn't sound like it is something that's very interesting or compelling in a print spool or driver on a Windows machine. But he saw that he had that little bit of insight and he had the drive to just continue and continue and continue. And it resulted in him being able to successfully find an exploit there. So transitioning, transition.

See that's a personality trait. So he would apply that to.

Yeah, you can apply that to anything. That's why I think some of the dynamics that make the Delta team so successful can be applied to other areas, whether it is cybersecurity or other business dynamics. So you transition from the military into the CIA. It was special activities divisions. I imagine there's a lot of similar stuff that you were doing while you're in the military. But how did the mindset or operational tempo change for you when you made that transition into the intel community?

So for me, I, you know, I was aging and I said I don't want to be that 60 year old trying to carry a rifle. And I looked at the agency and said, here's a place I can go and my country get some adventure. So I actually did not go sad route. I went the regular case offspring out because I thought that had more longevity. But it's more admin a lot of writing. You know, you do the dinner circuit. You, we've all heard stories from, from how it is at the Farm and you're a diplomat undercover and you play that. Of course, for me, that's what I thought I was moving into. But after I became certified as a case officer at the beginning of my career, oh, we have a new job. I went back to Afghanistan, which was supposed to be for a year, but it wound up being three. And then the people there knew me from either Iraq or Afghanistan or so that of me, I was out chasing down IEDs and meeting with Taliban and you know, going out with ground branch people out in the bases and stuff. So it was good, it was exciting. I got to a little bit of the tradition working in the capital, trying to recruit people in the Afghan government or whatever. So that was a big, it was a big change. It goes to go from the guy that's on the point doing the dangerous stuff to guys that were my former as a case officer, you know, they were the guys that would that when I would go out for a meeting with a drive you and serve as bodyguards. There were actually a couple times where they turned to me and said, can you help us? And you know, I was honored that they thought enough of me my skills that they still would trust me to do that because they don't, they don't generally trust a case officer to do that. And you have to look at and for me like one of the biggest achievements I had as far as this whole counter terror war, including, you know, being in Delta and all, was actually using a combination of my military experience officer to plan and run a couple major counterterror operations that resulted in.

You.

Know, that were successful and had very good results. And I said, wow, I actually had more impact on the bigger war on terror sitting behind a desk and going to meetings than I Ever did, being sniper instructor, all that. And so I never thought when I started my career as a young man that wow, the biggest impact you'll have is behind the desk. Illuminating for me.

Yeah, interesting. So, you know, one thing that I've seen you write and talk to a couple different times is, you know, from an individual safety perspective, you talk about operating in Yemen all alone for several months and having the same requirements as, you know, somebody else, whether it's a team or whatnot, from a security perspective. So can you kind of step through that mindset? What is it like to be kind of a one man team that is responsible for the entirety of your own security?

So it's, you know, when you go somewhere like Yemen or some of other countries and you don't have you, you have to provide the same security but you don't have those other people to do that with. You know, when you're on a team, you take turns. When you're even with one other person, one of you is watching the sense back, you never do anything alone. Well then if you're required to be by yourself, you've got to figure other ways to provide that security. And you know, I learned that you have to be on no downtime, that when you're out, like when I'm driving somewhere around Yemen, I can't relax and think about something else. I have to be tuned in to what's going on in the cars around me, what's going on on the sidewalks around me, what's my route, what's my emergency route. If I get blocked here, where am I going? So you know, it's kind of like you can't, you can't ever let down. You know, it's not the same security, but it is more you have to do your homework ahead of time more, you need to understand your routes more. And if you're one guy, maybe with a pistol, you're not going to use the same shooting techniques and try to shoot your way out of trouble. So you need to find that way to avoid it first, recognize it and you know, it's like we talked about earlier, make your decision early back or try to seek safety in somewhere else. You can't. When you go month after month, you have to have some downtime. But the question is that when you have the downtime, it's like you have to pick is when that is. So. No, but you have to understand that there's limited times where you can do that and you shouldn't be distracted when you are.

Sorry, I apologize.

I'm getting a little bit of audio distortion. Let me ask, this is insightful. I think we could talk for a couple more hours. But, you know, one thing we like to close on is ask what are you reading these days? What's on. What's on your reading list or a book that you found to be insightful here recently?

So I'm, I'm reading history books and I think last time I spoke to you I was reading a book on Washington. So I was just picked up a book on Ben. So I want to go back and see him. I think for the times we have now, I kind of like going back to our founding fathers and see like how in the mess we were back then, how did they figure out where we were to create what we have now? So I actually can't remember the name of that book, but that's my book now that I just picked.

Yeah, I'll ping it offline and we'll put a link to it in the notes for the show. So thank you. Thank you so much for joining us. Very, very insightful and lots of great stories and lots of lessons. I think that can be applied to others along the way as well.

Hey, well, thank you, Matt. And sorry about the audio here towards the end.

Yeah, no worries. Take care. Thanks.

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