shadowy figures walk in a blog about Covert Operations – Lessons And Applications

Covert Operations – Lessons And Applications

Posted July 26, 2018 by Ami Toben

Covert Operations – Lessons And Applications

September, 2012. A cafe in Palo Alto, California*.

Two men were sitting at a table and talking. One of the men was a former sales executive who had very recently been let go by a global IT corporation. The other man was the CEO and founder of that corporation, who had agreed to meet with the former executive upon his request. Unbeknown to both men, two covert operators were also in the cafe – one sitting at a table a few feet behind the CEO, the other at a table behind the former executive.

The former executive had been known to be belligerent at times, which was part of why he got himself fired. But he also had a relationship of some years with the CEO, which is the reason why the CEO agreed to meet him at the cafe just outside the corporate headquarters. The company’s human resources director, who was informed of the upcoming meeting, was much less comfortable with it and was the one who contracted us to covertly protect the CEO.

The operator behind the CEO was me. I had covertly followed him there from the moment he left the corporate headquarters. The second operator had taken position in the cafe earlier on, and was seated at a table with his laptop computer (the backpack he brought the laptop in also contained emergency medical response equipment). The meeting, which lasted around thirty minutes, had a few stressful moments to it, but eventually ended without incident. The second operator covertly followed the CEO back to the corporate headquarters, and I stayed back to keep an eye on the former executive. We switched roles in order to prevent too much direct correlation between us and the two individuals. The CEO arrived safely at the headquarters, and the second operator took a covert position covering the main entrance. The former executive left the cafe, but then entered an alley nearby, and walked all the way to its opposite end, which put him about half a block away from the main entrance to the corporate headquarters. He then stood by at the end of the alley, and nervously smoked two cigarettes while fiddling with his cellphone. It wasn’t looking particularly good, and from the other end of the alley, where I had taken a static position to observe the former exec, I communicated this to the second operator who was still covering the entrance to the corporate headquarters.

After a tense fifteen minutes, the former exec exited the alley and started walking away from the headquarters. Though this was what we hoped he would do, we knew of past case studies where disgruntled individuals only leave the scene in order to get a weapon from their vehicle, and I decided to covertly follow the former exec to make sure he was leaving the area for good.

Mobile surveillance on a potential hostile individual is different from the type of closer, protective mobile surveillance we had conducted on the CEO, and the distances I had to maintain from the former exec were much larger. I eventually ended my mobile surveillance when the former exec reached a train station a good two miles away (it was quite a walk).

This operation ended successfully with all mission parameters being achieved: Everyone went home safely at the end of the day, security was maintained throughout the operation, and because proper covert fieldcraft was applied, reputations were maintained and potential public relations problems were averted.


Though a cafe meeting between two people might seem simple, planning a protective detail, let alone a covert one, is more complex than most people think. It started with the fact that the two individuals were coming from two different directions which could not be plotted out – we obviously couldn’t coordinate with either of them. The start time and location for the meeting was the only known factor we had, and once the meeting was over (we couldn’t be sure how long it would take), we had an educated guess about the CEO going back to the HQ the same way he came to the cafe (because that’s what people usually do), but no real idea where the former exec would go.

Our plan had to be as detailed as we could make it, but also simple enough in order to roll with the inevitable punches. We conducted advance walk-throughs to cover both relevant locations (the corporate HQ and the cafe), all access points, possible routes, side-streets, and vantage points. We had also met with the corporate headquarters’ security manager to coordinate, establish lines of operational communications and get photos of the CEO and the former executive so that we could recognize them.

Rolling with the punches

The first curveball came right at the beginning of the operation. During the planning stage, the HQ security manager had insisted that the operation begin with the second operator (the one inside the cafe) covertly communicating to him when the former exec showed up at the cafe. The security manager would then let the CEO know that he’s good to go for his meeting, and would then communicate to us when the CEO was about to exit the HQ building. I already had my doubts about this idea, which was a bit overly complex and that depended not only on factors out of our control, but on a security manager who was not trained and experienced in these types of operations. For this reason, the second operator and I had prepared for the possibility that things would not actually get started that way – which was indeed the case.

Instead of walking into the cafe, the former exec decided to wait for the CEO outside the cafe, which meant that the operator inside the cafe couldn’t see him and report that he was there. Additionally, the security manager, who did not position himself very well, failed to communicate to us when the CEO was about to exit the HQ building, which he promptly did without giving notice to anyone (as CEOs often do).

Training and experience had taught me that the initial transition from static surveillance to mobile is always a crucial one, and I had taken a good vantage point outside the HQ for this reason. Our first realization that the operation had begun was when I caught a glimpse of the CEO as he exited the HQ building, and started walking towards the cafe. It’s often said that luck favors the well prepared, but I believe you make your luck. We had prepared so well for this, and I studied the CEO’s photo so well (I had never met the man before), that I immediately recognized him, even though I could only see the back of his head as he exited the building. I followed him relatively closely, communicated what was going on to the operator in the cafe and when the CEO got to the cafe, the other operator communicated back to me that the two men had just walked in and were ordering coffee without incident. I held back about fifty feet outside the cafe, and entered a few minutes later in order to avoid directly correlating to the CEO’s movements. I ordered a cup of coffee, and sat down at the table behind the CEO. The other operator had been closely watching the two the whole time they were in the cafe.

When the meeting was over, and the CEO went back to the headquarters (with the second operator closely following him), we had not expected the sales exec to go into the alleyway. Nevertheless, since we conducted a thorough advance of the whole area, we knew the alley well, and knew exactly where it led. The holding pattern we had to maintain – with me covering the former exec in the alley and the second operator covering the entrance to the headquarters – was not the best case scenario we were hoping for, but certainly a possibility we were prepared for.

Solid preparation, good communications, a simple plan and a flexible disposition, can enable you to roll with most of the punches that field operations will inevitably throw at you.

*Various details have been changed in order to protect the identities of those involved.

Ami Toben

Author, consultant, operator, security director.

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