You Me, Same Same | CIA
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Welcome to True Spies. Week by week, mission by mission, you'll hear the true stories behind the world's greatest espionage operations. You'll meet the people who navigate this secret world. What do they know? What are their skills? And what would you do in their position?

This is True Spies. Even if they know this whole time Ryan was only after me to do this, even if they're thinking that, they've already rationalized that away because they have so much trust and love and respect and that foundational relationship is so strong. They might think that, but no, I'm different. This is True Spies.

Episode 67, You, Me, Same, Same. Think for a moment about someone you trust, someone you can always rely on. Maybe it's your partner, your flatmate, maybe even your business associate. Think back to the early days of that key relationship. How did it begin? Who initiated the exchange? What was the power dynamic between you? We're all born into families, but everyone else in our lives is an asset.

We size them up. We earn their trust or not. And in exchange for our time, our friendship, our insight, our expertise, we gain something. A shoulder to cry on, a good laugh, a sympathetic ear, an informed opinion, sometimes an attractive sum of money, and sometimes all of the above. If that sounds rather cynical, you're thinking like a civilian.

Set aside the black and white mindset and put yourself in the shoes of a spy. What really makes a good operations officer is your ability to live in the gray. A lot of people that have a black and white mentality don't do well. Think back to that person you trust so much. Would you feel betrayed if you learned they were after your secrets? Would you conceal the truth if you wanted theirs?

Can a relationship built on secrecy also be one of trust? My name is Ryan Hillsberg. And while I was at the CIA, I was an operations officer and I was in the agency for about 13 years. I did the bulk of my career in Europe, a little bit in the Middle East and Asia, and really enjoyed the career. Ryan Hillsberg could teach a graduate level course on human relationships.

In his time with the CIA, he honed the ability to turn people he'd only just met into close personal friends, a skill he put to work in order to recruit foreign assets for the agency. But it's a fine line between persuasion and manipulation. Listening to his story, you might come to wonder, who are your friends really? How do you know who to trust? This particular operation took place in an undisclosed location,

We can't share too many specifics. We can say it unfolded somewhere in Europe, somewhere in the world of the gray. So by the time I get to this story in my career, I had been in for several years and, you know, I was gaining confidence and I was understanding how to utilize all the tools and training and knowledge that were given to me at the farm and headquarters. The farm.

If this is your first tango with true spies, that's a secretive training facility where would-be CIA officers are put through their paces. And being able to wade through that grayness, I think, is probably one of the key things to getting through the farm because there's never a right answer. The answer is, and this is used actually at the farm every single day, every operations officer, every intelligence officer knows this phrase, and the phrase is, it depends.

Of course, not everything in the CIA is painted in shades of grey. Intelligence operators working overseas must be keenly aware of entities that are working against American interests full stop. And on this particular foreign assignment, Ryan was made aware of one of these bad actors. The country that I was serving in, almost every country in the world also had some representation there.

And, you know, there was a lot of companies based in this location as well. And there was a company that was identified as being heavily involved in illicit financing activities with a country of extreme interest.

And this country, you know, it was a nefarious country. We didn't have the best of relationships with them. They were always, you know, trying to circumvent international pressure, etc. Ryan can't give any more details. But just to illustrate the sort of high stakes intelligence matter we have at hand, let's use a hypothetical scenario. Say there's a company with a massive amount of power, maybe an online retail giant that sells just about everything to people all over the world.

Now imagine if that company were run by the Chinese or by the Russians. Would you be concerned about how they were using their power or how their respective governments might be using the power and reach of the company? Think about it. A corporation with more data than you can possibly imagine. Virtual personal assistants listening in every hour of the day. A burgeoning drone program that might one day fill the airspace with proprietary AI.

Say that company is in the pocket of some bad actors on the international stage. You'd better believe the CIA would take note.

Why? Well, you know, we'd want to know what type of dual-use technologies this program had. You know, while these drones are flying overhead in our cities and across our countries, what else could they potentially be doing? You know, dual-use technologies, video recording, retention. We'd want to know their five-year strategy. We'd want to know their plans and intentions. I could guarantee 100% that the U.S. Intel community would be interested in

Got it? So, back to reality. There's a suspicious-looking company operating in this undisclosed foreign country, and Ryan and his colleagues have their interest piqued.

And so when we identified this company, we were actually pretty intrigued at some of the intel that we were getting and how they were working and supporting this country. We decided we needed to know a little bit more and we wanted to know what was going on. You know, what strings were being pulled? What types of relationships did the country have with this company? And what type of things were happening under the table? And we were needing to really find out the inner workings and specifics of

of this commercial government contract that they had. To dig deeper, they needed an inside source, an asset willing to divulge this company's most closely held secrets. After all, companies don't work without people. But to find one, they'd need to take a closer look at the company.

The local CIA station chief tasked a few operations officers and a targeting officer, someone skilled in identifying people and organizations who might have access to key information, with creating a targeting package, which is... An operational plan. First of all, who are we going to approach? And once we've identified the who, how are we going to do it? Of course, not just anyone is amenable to recruitment at any given time.

And not everyone who's recruitable is a good match for the CIA. Ryan and his fellow officers would be looking for just the right person, someone who would ultimately want to work with the Americans, even if they didn't know it yet. We don't blackmail anybody. We don't force anyone to work with us. And there's a reason for that. There are intelligence services around the world that do that. I don't think it's good for business.

I think that, you know, we want to be able to treat our assets, our developmentals, our targets with respect. You know, we're there really to protect them and keep them safe so that they can continue to provide access to information of interest. In other words, not just a disgruntled employee looking to let off steam. No, they wanted a trustworthy insider with precisely the right disposition.

Someone who could be a loyal partner to the American Intelligence Agency. It's a two-way street. Any party at any time can end the relationship. So in the recruitment cycle, there's, we call it SADRAT. It's spotting, assessing, development, recruiting, agent handling, and then terminations. That's the recruitment cycle from A to Z. A six-step cycle for the recruitment of assets.

Let's begin with step one, spotting. We looked at the company and we tried to figure out, okay, which three individuals would most likely have access to the information that we were looking for. Based on the previous intelligence and the relationship between this company and the country of interest, what three individuals would be the best or the most bang for our buck?

So we identified those three, we found them, and then we did a deep dive on those individuals and we wanted to know everything about them. Step two: assessing. Think of it as the most intense professional background check you've ever had for a job you never even applied for. Ryan and his colleagues looked at public records, social media pages, and any classified information they could dig up for their top three contenders.

Any scrap of information they could find would be a clue to who their targets were and how likely they were to be recruited. So once we did that with those three individuals, we looked at all the information we had and then we decided to go after one of them. And once we made that final selection, we did an even deeper deep dive to see if there was anything else that we were missing. A deep dive is an apt choice of words.

As it turned out, Ryan's target seemed to have just the right frame of mind for recruitment. He also had one notable hobby that caught Ryan's attention. As I looked at this target, I kept coming back to one thing. He was married. He had a couple kids. He had a great job at this company. He was doing pretty well. He was pretty successful. But as I was looking at a lot of the targeting paperwork, his hobbies and what he did, I

I had a feeling that this target was a little bored. Life was a little boring for him. But the one thing that he was passionate about, the one thing that let him sort of come out of his daily doldrums, you know, the one thing that helped break him out of the daily life, the monotony, was scuba diving. Let's take a moment to review three key pieces of information Ryan had gathered about this target.

Number one, he'd achieved some measure of success at his company. He would certainly have access to key information the CIA was looking for. Number two, he needed something to shake things up in his life. Maybe a bit of intelligence gathering would be just the thing. And number three, he had a hobby. And for Ryan, that created an opening.

And I remember as we were going through the information, the chief of station at the time looked over at me and said, you know, Ryan, we want you to go after this target. You know, how do you think you're going to do it? I'll give you one good guess. Now might be a good time to put the action on hold for a moment to learn a bit more about our true spy. You see, Ryan himself is something of a hobbyist, and that's putting it mildly.

When he isn't spending time with his wife and five children, he keeps himself busy as an amateur musician. I play piano the best. I've been playing the piano since I was six years old. On a number of different instruments. The penny whistle, yes. The Irish penny whistle. I've got several of them. He's an avid home chef. Bobby Flay. Bobby Flay is my hero. With a penchant for leather work.

Wallets, backpacks, purses, handbags. I've sold quite a few. It's more a labor of love. It might sound like Ryan has plenty of time to burn, but cultivating a varied set of interests is a smart professional move. A spy who's a jack-of-all-trades is likely to form a connection with an asset over one hobby or another, even when the homemade rucksack business isn't doing so hot.

It's important, especially for an operations officer, to be well-rounded. The more well-rounded you are, the more conversations, the more that you can connect with someone. If you have a number of hobbies and skills and interests that you can speak to about yourself and that you can find common ground and common connections on, the more easily you're going to be able to build a relationship with someone.

In fact, finding commonalities with an asset is so key to recruitment that the CIA has given it a name. You, me, same, same. Find common ground and you can show your target, look, I'm trustworthy. I'm just like you. Same, same. And it works. Suddenly, you're not just a friendly stranger. You're a peer. With all his interests to draw from, a guy like Ryan has plenty of opportunity to exercise you, me, same, same.

I've been fascinated with knives. I've had a couple different knife collections since I was a kid. Still fascinated with knives. And so I was going after a nuclear target actually. And this target was also a knife connoisseur and actually gave me a couple knives that were given to them from their father. Knives were something that really were a big part of that developmental relationship actually. And something that we bonded over for many months.

Now, that's all well and good as long as your target is relatable. But what about when there's nothing to bond over? What if your target's hobbies are truly niche or bizarre or just downright boring? There are some operations officers that sort of fake being interested in them. There's, of course, assets that, you know, you may not necessarily ever be friends with in real life.

But the ability to find something to connect with them on, a genuine connection, a genuine interest, a genuine friendship, I think it's a must. It's a key to having a successful clandestine relationship. And so earning trust, building a relationship of trust and rapport with someone, that's what everything hinges on.

You know, you can't convince someone to betray their company or their country or to commit espionage unless you have a foundation of trust that is so solid and a relationship that's so strong. It won't happen if you don't. That's precisely the kind of relationship a spy needs for the next phase of the sad rat cycle. Step three, developing.

cultivating a friendly rapport with your target every time in order to gain their confidence. If you've assessed that they may have access to interest, or you may already know that they have access to interest, then you're going to start this process called development. You're going to develop a relationship with them. And development, it can last three months, it can last six months, it can last a year or two, depending on the target, the country that they're from,

and how difficult an operation it might be. Which brings us back to our undisclosed European locale, back to the target at hand, a family man working for a company that has piqued the interest of the CIA, a man in need of a venture with one great consuming hobby.

This guy loved to scuba dive. It was his passion. It was something that he did as much as he possibly could. All of his travel that he did internationally involved scuba diving. And in the city that we were living in, there were several different scuba clubs. And he was a prominent member of one of these scuba clubs. And they had weekly meetings. I think it was Wednesday nights.

And this dude would never miss. I really thought this was the perfect recipe to really start building that trust. And so that's what I proposed to the chief of station. And it was approved.

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They share three books they love, one book they don't, and what they've been reading lately. And I recommend three titles they may enjoy reading next. Guests have said our conversations are like therapy, troubleshooting issues that have plagued their reading lives for years, and possibly the rest of their lives as well. And of course, recommending books that meet the moment, whether they are looking for deep introspection to spur or encourage a life change, or a frothy page-turner to help them escape the stresses of work, or a book that they've been reading for years.

school, everything. You'll learn something about yourself as a reader, and you'll definitely walk away confident to choose your next read with a whole list of new books and authors to try. So join us each Tuesday for What Should I Read Next? Subscribe now wherever you're listening to this podcast and visit our website, whatshouldireadnextpodcast.com to find out more. Wednesday night scuba meetings created the perfect window for a first encounter.

Ryan learned everything he could in preparation for his first meeting with the target. About the target, of course, but also about scuba diving. First, I had to buy some equipment because I didn't have anything. And so I got some basic scuba diving equipment. I signed up for lessons and I joined the scuba club that the target was a member of. Don't get the wrong impression. Ryan did not become a master diver. Not before developing his asset and certainly not after.

By his own admission, he's more of a snorkel kind of guy. The scuba club just helped him get a flipper in the door. I wanted to specifically meet him and have a very specific conversation with him, a tailored, pre-planned, sort of strategized conversation. And that's exactly what I did. Ryan left not a single detail to chance.

I wanted to be prepared and to lead and guide a conversation from A to Z. I was prepared to ask him certain questions already knowing the answers to those questions that would then lead and guide me through a discussion that I was controlling. In a first encounter with a potential asset, a spy like Ryan has one primary goal to open the door to a second encounter.

Set the stage for another meeting, by arrangement or by chance, when you can spend one-on-one time with your target. Slowly build familiarity in order to build trust.

When an operations officer approaches a target, your goal is to make contact and to get a second meeting. Like that hook for a second meeting, you know, it can be anything. And once you get them to a second location where you're just one-on-one with them, you know, all the training, all the skills that were taught at the farm, you know, all of our experience in doing clandestine operations, that kicks into gear when you're one-on-one with someone. And then you can really take the relationship off from there.

So the scuba club was a great start, but Ryan needed a subtle way to start to sidle up to his target alone. One of my plans was to strengthen the relationship that I had with him after the initial meeting in seeking his advice, seeking his input. You know, he'd been scuba diving for so long, there was a lot that he could teach me. And if I had questions, you know, I could go talk to him and he could provide some insight for me.

from his experience and perspective on whatever question that I was asking him. So it was in that type of sort of informal, you know, teacher-student type of relationship, you know, although we were roughly the same age. It's something that works. Another espionage tactic you might discover in the pages of your Psychology 101 textbook. If you want someone to like you, ask for their help. Ryan's plan went off without a hitch.

I ended up talking to this target for over 45 minutes. And that's a lot of time on... We call it time on target. You want time on target. But it wasn't just that Ryan had reeled in his target with his talk of deep sea diving. Nor was it the fact that his target had taken the bait of his pre-planned conversation. No, as Ryan himself said, he doesn't fake it. He had laid the groundwork for a real-life friendship.

And in those 45 minutes, the men had become, well, rather smitten with each other. By the end of us talking, and this is a funny phrase that I use a lot, but there's a bromance there. There's a lot of people in this world that really can never be themselves with people. And so being able to take those walls down and to be able to be that someone that your target can talk to you about anything about,

for them to trust you, to talk about their innermost secrets, their innermost concerns and anxieties and fears. That's what you want. That's what that development stage does. So by the end of this first Scuba Club meeting, this guy loved me. Is anything about this ringing alarm bells? Ryan needs this man. So he not only ingratiates himself to him, he all but seduces him. But by Ryan's account, the feeling was mutual.

These guys had a genuine fondness for one another. It was a two-way street. The courtship ritual had only just begun. Ryan and his target arranged a lunch date at a local Italian restaurant. You might be thinking, scuba diving? Italian food? Nice work if you can get it. But there was nothing casual about these casual encounters. The two men were meeting out in the open, having unclassified conversations. But that didn't mean Ryan was off the clock.

Of course, before I even met him, I conducted the surveillance detection route on the way there, an SDR or a surveillance detection route. Depending on where you are in the world, it can be shorter or longer, but it's usually at least one to two hours.

And it's a route that you take either in your vehicle or on foot or with public transportation to ensure that nobody's following you, especially if you're a diplomat or if you're a government official or if you have a relationship with the local country and they know that you're CIA and you work with their liaison service. You need to make damn sure that you're showing up to this type of meeting, especially when you're meeting the target, that no one's following you. It's also done affirmatively.

after the meeting, not only to protect yourself, but more importantly, to protect the target that you're meeting with. Ryan also took pains to select a restaurant where the two could speak freely with one another, one that was popular, but not too popular. Enough space between tables that the two men could speak openly without worrying that someone would overhear them.

So this Italian restaurant I had used a couple times for various reasons and decided to meet him there so that we could have a more sort of intimate discussion. I don't remember the exact circumstances, but he had had a very, very stressful day at work. The obvious question that I can ask is, well, what happened? I do want to point this out. I developed this target for several months, several months.

And I never once brought up his job. It was never me bringing up his job ever. Now, if he brought up his job...

and put it on the table, I'd attack. I'd ask questions. I'd follow up. I'd be a listening ear, a concerned friend for him to confide in. And so luckily for me, at this very first lunch meeting, he talks to me about being stressed at work. He puts that on the table. So I start ticking away at it, asking questions. Well, hey, man, what happened? What's going on? Talk to me. If someone puts something on the table, you attack. Okay.

Attack, like any good friend would do. The target's bad day was Ryan's small victory.

Away from the rest of the Scoop Club, he could guide the conversation into deeper waters. So that first meeting was actually really special because I was able to get him talking about work right off the bat and getting him to open up about some of the struggles that he was having there, which as part of the developmental relationship and that developmental phase, that's what you want. Remember, we're still in phase three of the SADRAP cycle.

The CIA will only make a formal recruitment of Ryan's target after successful development. Ryan needs to continue to gather information, to learn if he'll make a good asset for the agency. Is he reliable? Can he be trusted? What are his strengths and what are his weaknesses? And then there's the question of the target's motivations. If he agrees to spy on his own organization, will it be because he's driven by ideology, money, or something else?

Back at the Italian restaurant, Ryan is schmoozing away. He's like the duck on the placid lake, calm on the surface, but paddling like mad underneath. So after two hours meeting with this individual at lunch, I would then go back to the office and I would write out everything we spoke about.

So I'm not there at lunch taking notes. You don't have a recorder sitting on the table. You don't have a pen and paper out, you know, or your iPhone, et cetera, et cetera. No, this is a normal conversation. You and me talking, conversing as friends, while at the same time, you are remembering something.

or trying to remember as much as possible everything that was said in the discussion. Not just what they said, but also what you said and the questions that you asked, and then how they responded. And not only that, you're making little mental notes in your mind as you're talking with them about those motivations, about those vulnerabilities, those strengths, those weaknesses. You're assessing them. Things progressed in this manner for months, and the bromance blossomed.

Ryan and his target went diving at a local lake and made day trips to a neighboring country. They even planned a longer excursion to a more tropical locale, but Ryan knew it would most likely never come to pass. And like in any other burgeoning relationship, there came a point when it was time to meet the family. I thought it was really important, especially with this target. You know, he was married, he had two kids, and we were meeting at least once a week, sometimes twice a week.

And sometimes you do this, sometimes you don't. But I thought it was really important that I meet his wife and his family. Not just because I'm sure his wife was wondering, who is this guy that my husband's hanging out with all the time, right? Because oftentimes that's odd, you know, especially as we all get older. Oftentimes our friendship circles sort of decrease, especially once we have kids. Then all of a sudden, you know, your spouse is off hanging out with someone, lunch and dinner and movies and scuba diving, you know, day trips, et cetera, like that.

Who is this person that my husband is spending all this time with? So I remember meeting his wife for the first time. And it was clearly evident to me that the target had never really had a friendship or a relationship with someone like me or anyone that he was spending this much time with. Imagine yourself in Ryan's shoes. You've been laying the groundwork for a formal recruitment for weeks.

You got to know this guy before ever even meeting him. And now you've won him over with your shared interests, your desire to learn from him, your willingness to listen and to empathize. Your buddies, kindred spirits even. You, me, same, same. Now you're in his home, sitting across the dinner table from his wife, and it hits. There's no one else like you.

Your techniques for sustaining conversation, building trust, getting time on target are all so effective. You've become a singular entity in this man's life. Yet you're only friends with him because you need something from him. Would you carry on with the ruse? Knowing that deception was at the foundation of your friendship, would you resolve to make the recruit as soon as possible? Just for the sake of making everything above board, aren't you starting to feel just a tad...

Manipulative. You know, manipulation, it's a... Manipulation is a delicate word. If a developmental relationship is done in the right way to the target, it won't seem manipulative at all. In fact, if it's done the right way...

it'll appear to them as a natural progression of the relationship. You know, you guys were just friends at first, right? Really good friends. You guys never talked about work. You guys met for three or four months, you know, and you never asked them about work. Even if they know in the back of their mind, oh my goodness, this whole time, Ryan was only after me to do this.

Even if they're thinking that in the back of their mind, they've already rationalized that away because they have so much

and love and respect and that foundational relationship is so strong. They might think that, but no, I'm different. And at that point as well, you've identified their primary motivation. And so you're also giving them what they want. This is something that they have to do. This is something that they want to do. This is something that they've been destined to do.

Ryan has wooed his asset, wined and dined him, and met the family. Now all that's left is to pop the question. Step four, recruiting. Unfortunately, there's no Hollywood ending here, at least not one that's declassified. Ryan had to be rather cagey with the details, but he did offer this. There are people out there in this world that propose marriage to someone without knowing for sure

what the answer will be. They're crossing their fingers. They're hoping, "Man, I hope she says yes. Man, I hope he says yes." You know, if you don't know if someone's going to say yes to a marriage proposal, you don't propose. Most normal people, you know, aren't going to propose to someone unless they know they're going to say yes. And I think the same can be said with espionage. Nothing kills the romance like being reported to the authorities.

There's still one more unglamorous side to this story. As it happens, Ryan's obligations to the agency forced him to leave his friend and his posting behind. The final letters in the Sadrach cycle, agent handling and termination, fell into the hands of other officers. So much for those buddy-buddy kumbaya diving trips. Summer camp was over.

And I had a really, really strong friendship with him. Didn't want to leave. Didn't really want to give up the case.

And I think that's the flip side of it. When you develop these types of relationships with your targets and with your assets, sometimes it is hard to leave because you have to leave at some point and you're not allowed to continue a friendship with an asset or a target once it's been turned over or once you've been assigned to a different location. If you are no longer the handling operations officer, if that asset or target is no longer yours and it's been turned over to someone else,

There's no more contact. It's a little sad sometimes. You know, there are assets and targets that have shared things with me that they've never shared with anyone else in this world. And I think that's what's really special. And I think that's why there is this bond between operations officers and their targets that just transcends years and decades of

Today, Ryan works as the director of corporate security for a large biotech company, helping to defend against the very same people that he once helped to recruit. Employees that give up insider secrets and get recruited by foreign intelligence services end up costing their organizations thousands or even millions of dollars a year. Ryan uses his own experience as a cautionary tale. Like it or not, we're all living in the gray.

You never know what might happen when you meet a kindred spirit. Make a new friend and let your guard down. I do continue to share this lesson in corporate security because I need employees to know why they might be a target. You know, why would someone be targeting them? Because everyone thinks, oh, I'm not anyone special. Why would anyone want to talk with me? Even just access to a company's network, you know, that could make you a potential target. Think about the people around you.

I don't think people can say, oh no, I could never get recruited.

I don't think people can say that because if it's the right person going after you in the right way at the right time, they're good. Operations officers, they're really, really, really good at what they do. And you may not even know what's happening. I'm Vanessa Kirby.

You can learn more about Ryan Hillsberg in the book Licensed to Parent, written with his wife, former CIA spy Christina Hillsberg. It's available in print and as an e-book now. Join us next week for another liaison with True Spies.