Agent Handling 101: The Psychology of Running Spies

Listen to Ryan Hillsberg’s Story | You, Me. Same Same.


Recruiting spies is an art, a cat-and-mouse game that - if done properly - the ‘asset’ might not even notice. In fact, ex-CIA officer Ryan Hillsberg believes they may even enjoy it.

“Even if they know, in the back of their mind: ‘Oh, my goodness, this whole time, Ryan was only after me to do this.’ 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 then… ‘No, I'm different’.”

Ryan spent 13 years sizing up potential spies for the CIA in Europe, the Middle East, and Asia, so he understands what makes a good operations officer. It’s a fine line between persuasion and manipulation though. So how does it work? How does Ryan turn people he’s just met into close personal friends?

Ryan Hillsberg, ex-CIA officer and agent handler
Ex-CIA officer Ryan Hillsberg wants to be your friend. No… really. 


Agent running

Imagine there’s a company with a massive amount of power, possibly an online retail giant that sells to people worldwide and gathers their data. That’s exactly the type of business that catches the attention of the CIA - particularly if the company is flying drones over cities and gathering intelligence they may not need to deliver parcels. 

The business would have to be foreign-owned to gain the interest of the CIA. "To be clear," Ryan emphasized, "the CIA does not collect intelligence on US companies or US persons."

Agent Handling 101: The Psychology of Running Spies

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Listen to Ryan Hillsberg’s Story | You, Me. Same Same.


Recruiting spies is an art, a cat-and-mouse game that - if done properly - the ‘asset’ might not even notice. In fact, ex-CIA officer Ryan Hillsberg believes they may even enjoy it.

“Even if they know, in the back of their mind: ‘Oh, my goodness, this whole time, Ryan was only after me to do this.’ 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 then… ‘No, I'm different’.”

Ryan spent 13 years sizing up potential spies for the CIA in Europe, the Middle East, and Asia, so he understands what makes a good operations officer. It’s a fine line between persuasion and manipulation though. So how does it work? How does Ryan turn people he’s just met into close personal friends?

Ryan Hillsberg, ex-CIA officer and agent handler
Ex-CIA officer Ryan Hillsberg wants to be your friend. No… really. 


Agent running

Imagine there’s a company with a massive amount of power, possibly an online retail giant that sells to people worldwide and gathers their data. That’s exactly the type of business that catches the attention of the CIA - particularly if the company is flying drones over cities and gathering intelligence they may not need to deliver parcels. 

The business would have to be foreign-owned to gain the interest of the CIA. "To be clear," Ryan emphasized, "the CIA does not collect intelligence on US companies or US persons."

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To find out what’s going on - including whether the company has any commercial government contracts - CIA agent handlers need to recruit sources inside who are willing to divulge this company’s secrets. 

The A to Z of recruiting is known as SADRAT - Spotting, Assessing, Developing, Recruiting, Agent Handling, and Termination.

You Me, Same Same Podcast, True Spies


Spotting 

A plan is drawn up involving a few CIA operations officers and a ‘targeting officer’.

“First of all, who are we going to approach? And once we've identified the who, how are we going to do it?” Ryan tells SPYSCAPE’s True Spies podcast.

The CIA looks for people who will, ultimately, want to work with the Americans -  even if they don’t know it yet. The Agency want trustworthy insiders, people who can be loyal partners.

The CIA want loyal partners in their foreign spies
The CIA checks social media and public information before approaching possible 'assets'


Assessing 

Once identified, the CIA does a ‘deep dive’ to find out more. Is the target happily married? Have they achieved a reasonable amount of success in their career? Do they have any hobbies?

Hobbies offer openings, opportunities for the CIA to wrangle an invitation into the target’s life without seeming obvious. Ryan is, by necessity, a jack-of-all-trades - an amateur musician, a chef with a knife collection, an artist with a penchant for leatherwork, and an athlete who enjoys scuba diving. 

The more well-rounded a CIA officer is, the easier it is to connect with someone. The CIA calls it: ‘You, Me, Same Same.’ 

SPYEX Consultant Ryan Hillsbergt
SPYEX consultant Ryan Hillsberg

Common ground implies an individual is trustworthy. Suddenly, Ryan is not just a smiling stranger. He’s a peer.
 

Developing

Ryan first move starts with a friendly chat: “Development 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.” 

In one case, Ryan took scuba diving lessons every Wednesday night in order to get close to his target, a married man who’d achieved a reasonable amount of success at his company and lived for his scuba club. 

“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,” he said. 

Ryan created an informal, teacher-student type of relationship to open the door to a second encounter. If you want someone to like you, ask for their help. “There was a ‘bromance’ there,” Ryan said, describing their first, 45-minute chat. The target felt he could talk to Ryan about anything, including his innermost secrets.

Once the courtship ritual is underway, it’s time for one-on-one meetings at a restaurant where the target might bring up a stressful day at work. That’s Ryan’s opening to pounce with innocent-sounding questions: “‘Well, hey, what happened? You know, what's going on?’... If someone puts something on the table, you attack.”

All the while, Ryan is assessing if the target is trustworthy or has any weaknesses.

Ryan Hillsberg recruited potential spying assets for the CIA
Money can help formalize the relationship between agent handler and spy

Recruiting

With the wining and dining accomplished, things move into the danger zone. Ryan needs to be frank about what he wants - he’s recruiting a spy, not a best mate. How can he be sure the potential asset won’t report him to the authorities? 

“Most normal people 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,” Ryan explained.

Many officers have told SPYSCAPE that an official payment - complete with receipt - can help formalize the relationship. It reminds the asset that mentioning the relationship could jeopardize their security. Money often isn’t the only motive, of course. Some spy for ideology, others are coerced, and some - like FBI-KGB double agent Robert Hanssen - also need the ego boost.

“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,” Ryan said.

Officers need to meet in secret locations with their spies
People skills are key to handling foreign spies

Agent handling

Agent handling is a secretive business, but there are a few general rules. The officer and their asset need to meet unobserved, for example. 

The agent handler’s job is to ensure a continuous flow of secretive information that would inform US policy interests and policy decisions - information that keeps Americans safe from threats - so successful handling is often measured by the quality of the information extracted.

People skills are one of the biggest weapons in the agent handler's arsenal. If the relationship isn’t handled properly, the asset may go to the press or their government. At that point, the risk becomes very real.

CIA Agents use their people skills to recruit foreign spies

Termination

In some cases, CIA case officers move on to another posting. If the asset is still providing valuable intel, they’re given a heads up and introduced to a new case officer. 

But what happens when an asset stops providing worthwhile intelligence? They are ‘terminated’ - Agency-speak for ‘fired’.

The officer sits down with their asset to outline the change. Often there’s a written summary of an earlier discussion about what the CIA would do, what’s been promised, and what will happen when the relationship ends.

An agreement might be in place for a termination payment. The reality is that officers can’t always keep promises made by another CIA agent if the context or Agency’s budget has changed. The goal is to part ways on a healthy basis, however, leaving the spy thinking their actions and the relationship were in their best interest.

Ryan sums up the feeling as: “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 Hillsberg is an expert on corporate security, insider threat, espionage, executive recruiting, and parenting using CIA principles. He can be booked at SPYEX.com to appear at events or consult on projects.

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