Lessons From The Field: Covert Operations

What follows is Chapter 9 of my book Surveillance Zone

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A technology conference somewhere in Silicon Valley, 2013.

The tech conference was coming along well, and thousands of attendees were busily going in and out of the convention center during their lunch break. I was on my third day working undercover and was becoming quite familiar with the comings and goings of the area around the convention center.

It was then that I saw a casually dressed man in his mid-20s walk up to a newspaper stand, lean over on it and observe the main entrance to the convention center. It seemed pretty obvious to me that the guy wasn’t actually a hostile surveillant. He was instead a member of the event security team—one who was trying (quite unsuccessfully) to take a covert position outside the venue. This young operator wasn’t aware of me and my team being out there, and, with his appearance and behavior, he made a perfect display of almost all the classic covert methodology mistakes I teach my trainees and team members to avoid.

I’m not sure if he took it upon himself to provide this “covert” coverage, but after I reported his activities to our point of contact, he was promptly pulled out of the field and no other member of his protective team tried anything like that afterwards.


One of the things that can happen when you get into the field of covert operations is that you start noticing more people working covertly, both on and off the job. There’s no surprise when this happens on the job (like in the case above), but the downside of having an eye for covert operations is that it’s difficult to turn it off even when you’re not on the job.

This means that, say, a stroll through an airport becomes a game of “find the covert security operators,” and walking past a large protest (there are quite a few in the San Francisco Bay Area) becomes a game of “find the undercover cops.” Once you know what to look for, games like these are not all that hard. I suppose it would be nice to just tune out this noise during my off-time and not play these games, but since I’m going to keep noticing all of this whether I want to or not, I decided long ago that rather than suffer from my involuntary hyper-awareness, I might as well have a bit of fun with it.

To be clear, I do try to stay out of other people’s business, and I never purposely go out of my way to look for covert operators. But, like it or not, if I can’t help noticing things like the young, short-haired guys with untucked shirts and earpieces wheeling their empty hand luggage up and down airport terminals, then why not just embrace such things and make all that airport waiting time a bit more interesting?

Over the years, I’ve noticed a number of common difficulties and mistakes that covert operators tend to make. Needless to say, I too have made all of the blunders I examine in this chapter, and it’s with this in mind that I offer my humble opinions, tips, and suggestions on the matter.

The following insights apply to most types of covert operations— from surveillance and surveillance detection to undercover investigations and covert security.


Let’s start with the basics. A cover is the visual projection of what an operator wants people to see and therefore think of them. For example, if you want people to think you’re a homeless person, you dress and look the part.

However, many operators make the mistake of formulating a cover that appears harmless, while forgetting that a cover that’s interesting, fun, or attractive—like, say, a brightly dressed tourist—is almost always a bad one. It’s bad because it fails the boring test. If there’s anything memorable about the way you appear, then your cover is less than ideal.

A cover story, as its name implies, is the verbal representation of your cover. In other words, it’s the story you tell, or the answer you give, if you find that you need to verbally explain who you are or what you’re doing. For obvious reasons, your cover story has to fit and even strengthen your cover. Otherwise, it’ll seem suspicious or curious if the person who looks homeless, for example, talks like a law enforcement officer.

One of the keys to the cover and cover story dynamic is to always start with a good cover and then work your way towards a supporting cover story. This order is important because the main idea is to visually embed yourself into the environment in such a bland and boring way that no one ever pays any attention to you, much less tries to question or talk to you. In an ideal situation, you would never even get to a point where you’d have to use your cover story.

As for the cover story itself, keep it simple and try to keep it within the boundaries of things you actually know from experience (so you can talk about it naturally and even elaborate if—and only if—you are asked to). At the same time, you want to stay far enough away from information that can lead back to who you really are. Do not volunteer too many details, and keep it bland and boring so that the person you’re talking to will forget you as soon as they walk away.


There’s a celebrated quote by Winston Churchill, who, after being asked to what he attributed his success in life, answered, “Economy of effort. Never stand up when you can sit down, and never sit down when you can lie down.”

This little tongue-in-cheek answer actually makes a good point when applied to covert operations. In most cases, movement attracts more attention than stillness, and standing attracts more attention than sitting. Bland and lazy are your best friends here.

In my experience, most people who gravitate towards covert operations tend to have backgrounds in military, law enforcement, or security—and sometimes all three. The reason I mention this is because people with these types of backgrounds naturally move and posture themselves in ways that are the opposite of bland and lazy. For the exact same reason that standing and moving around are good military, law enforcement, and security habits (allowing the operator to project more of a deterring presence while extending visual control), these same habits are bad for covert operations. The tendency to maintain a command presence and visually control your environment will usually make you stick out, as will any sudden movements, abrupt stops, or quick head turns. At the very least, these actions will make you look interesting, suggesting that there’s something going on.

As a covert operator, you want to do the exact opposite and appear bland, lazy, and boring. Keep in mind that it will be difficult to pull this off if you’re not actually comfortable. A person that’s physically uncomfortable probably looks uncomfortable, and looking uncomfortable can attract interest, curiosity, and suspicion.

So relax, settle in, and try to get comfortable—which leads us to our next point.


When you’re on a covert surveillance or surveillance detection mission, it’s almost always a good idea to sit down. The two main advantages that sitting down will give you are a less noticeable appearance, and the ability to see and notice more yourself. Though this seems like something the segment above already covered, I can’t tell you how many times I’ve heard myself repeat the “Sit down!” instruction during trainings, and even during operations (which is why it deserves its own little segment).

Despite what you may see in Hollywood movies, there are relatively few reasons for being in a fixed position without sitting down. So once again, relax, settle in, sit down, and try to get comfortable.


So you sat down, great. Now stay there!

It’s often the case that only after you’ve sat down at a vantage point that you notice an even better vantage point you could have picked. There’s nothing ironic about this—you’ll always be able to see and understand more after you stop moving and sit down (which is one of the main reasons you sit down in the first place). But as tempting as it is to move to that other, better position, it’s often a bad idea.

There might be many legitimate, non-suspicious reasons for normal people to move from one nearby spot to another, but even in the best case scenario, doing this will make you stick out more than if you just stayed at your original spot. And remember, you are not a normal person—you’re a covert operator moving from one vantage point to a better one (which is a classic surveillance indicator you’d want to avoid).

You’ve made your bed, now lie in it. Next time, try to find the better vantage point to begin with, but for now—stay put.


This one comes up a lot. You get to a new streetside location and quickly look for a good vantage point. As is often the case in urban areas, a bus stop just happens to be perfectly located for this. It often even has a number of people standing and sitting there—all the better for you to blend in. Good vantage point, right?

Wrong! Or at least almost always wrong (there are some exceptions, as usual).

Bus stops do indeed provide a logical justification for standing (or hopefully sitting) in very central locations, but this justification only makes sense if the bus stop is used for its intended purpose—to get on a bus. Using this vantage point for an extended period of time will not make sense because everyone else at the bus stop will eventually get on a bus, leaving the covert operator looking out of place. You might be able to justify a good 20-30 minutes at a bus stop, but eventually, you will have to board one of the buses that stops there.

Conversely, if you’re conducting mobile surveillance and only need to buy yourself some 30-40 static seconds till you get moving again, a bus stop might seem very inviting. But this too isn’t a great idea. Either spending too much time at a bus stop or quickly walking away from one without boarding a bus can get you detected.

Finally, if you absolutely must use a bus stop, pay attention to where the bus is coming from. The other people at the bus stop will almost always look that way, and you don’t want to be the single person looking the wrong way.


Your cell phone can be your best friend or your worst enemy depending on how you use it. Not only is your cell phone the most natural and least suspicious way to communicate in general, but with the advent of smartphones, it can provide a necessary preoccupation that can justify your presence at various locations.

It might seem counter-intuitive for people on important covert operations to keep playing with their phones, but that’s part of the point—appearing bored, distracted, and unprofessional is perfect for covering up what you’re actually doing.

Look around you the next time you’re out and about, and notice what bored and boring people are doing (remember, you want to look boring). Nine times out of ten they will have their smartphone in their hands. Additionally, your phone can even help you when conducting mobile surveillance on foot. As I mentioned earlier, unexpected stops are almost inevitable, and using your phone as a momentary justification for stopping (to seemingly answer some text message, for example) can be helpful at times.

One thing to keep in mind is that if you’re going to use your phone to justify your presence or rationalize a quick stop, make sure you’re actually doing something with it. In other words, don’t just pretend to play with a blank screen.

It’s also a good idea to silence your ringer. Although a ringing cell phone is not out of place, it can still draw attention to you. Likewise, if you’re pretending to talk on the phone in order to justify your presence somewhere, you don’t want your cell phone to start ringing while you’re holding it to your ear (if someone actually calls you by chance). In addition to looking absurd, it can draw even more attention your way.

As for actually using the phone (or any device that looks like a cell phone) for verbal communication, always avoid using tactical language and try to remember that people on the street can hear what you’re saying. Inexperienced operators have a bad tendency to say things like “Command from mobile-1. Target is traveling southbound on Franklin street.”

Needless to say, this is not how most people talk on their phones. Rather than using call-signs, try using names (they obviously don’t have to be your real names), and make up a name for your target, too—maybe something like Tim. So instead of the example above, why not say something like, “Hey Chris, it’s Matt. What’s up, man? I think Tim’s actually heading down Franklin.”

Also, keep in mind that most people don’t call someone to say only one sentence, so you might want to keep talking. You don’t have to fill up your communications network with chatter to do this—simply hang up (or cut off your audio) and blab on for a bit longer to make it seem more like a normal phone call.

If two operators are communicating with each other while in the same area (for example, inside a coffee shop or sitting on different benches in a city square), try not to start and stop communications at the same time since this can be detected as a correlation between the two operators. Instead, one of the operators should keep talking for a while after the other has gotten off the phone in order to make it seem like there is no connection between them.

As for hands-free extensions (both wired and wireless), I’m not a huge fan. For starters, unlike what you see in Hollywood movies, there’s nothing all that covert about the classic radio surveillance kits that dangle a “pigtail” from your ear and force you to talk into your sleeve or collar (Secret Service-style). More advanced wireless skin-colored mini earpieces and microphones might do a better job of concealing themselves, but you’ll still have to awkwardly (and suspiciously) talk into what looks like thin air. Of course, you could mask this by pretending to talk into a regular cell phone, but in that case, why not just talk into one for real?

The irony of using advanced technology for covert operations is that if these expensive tools ever get discovered, there’s a much greater chance you’ll get exposed than if you just text or call with an ordinary (or ordinary-looking) cell phone.


When most people imagine what a covert operator looks like, they tend to think of a solitary individual (usually male). When instructing an SD course, I’ve found that it usually takes the trainees a few days to realize that it can be beneficial to work in pairs—or even groups—and indeed it is.

Few things are more innocuous looking than a man and woman sitting together in a coffee shop or walking down the street. What are the man and the woman doing over there? They’re sitting and talking, right?

Yet another advantage that working in pairs can provide is teamwork. For example, two people can sit facing each other pretending to have a casual conversation while one is focusing on the target and describing what they see and the other (who’s facing away from the target) jots down or communicates the information.

The main thing you want to avoid while working in pairs however is any type of meeting or splitting up in the field. If you come alone, you leave alone, and if you come together, you leave together. Watching people meet up or split up is much more memorable than seeing people arrive together and leave together. The absolute worst thing you could do—a classic mistake I’ve detected in real life—is to arrive in the area together and then split up to take different positions.


You’ve probably noticed how often coffee shops come up when I discuss covert operations. This is because coffee shops provide some of the best vantage points (and are often located in areas where covert operations take place). Part of what makes coffee shops so ideal for surveillance and SD is that, unlike most other businesses, they will let you spend pretty much all day there, more or less unharassed. The closest thing to a coffee shop situation might be a restaurant, but those usually have servers who will keep checking on you and who will eventually expect you to pay for your meal and go on your way.

On a side note, if you must take position in a restaurant (maybe in order to closely surveil a hostile target or to covertly protect a client who’s having a meal there), it’s a good idea to pay for your meal as soon as it arrives. You won’t want to frantically wave over your server or the check if your target or client begins to leave unexpectedly. Conversely—from the SD perspective—look out for restaurant patrons who pay for their meals as soon as they get them.


There’s no point in ignoring this fact—the archetypal covert operator is male, somewhere between his 20s and 50s, and usually has a background in military, government, law enforcement, or security.

Lest you think this discriminates against those who don’t fall into this demographic, let me assure you that the opposite is the case. Simply being female gives an operator a natural advantage, as does a younger or elderly appearance.

I can tell you from years of experience that some of the hardest individuals to detect (on both sides of the surveillance/SD fence) are quintessential “little old ladies,” young Asian females, and anyone else who doesn’t fit the mold that most people imagine when they think of a covert operator. The fact that you probably don’t visualize people like this when the term “covert operator” comes up, and the fact that you’ll rarely see them depicted in movies or on TV shows, is precisely the point. It’s why these operators are so effective at remaining unnoticed.


One of the most important, yet difficult, factors for covert operators to deal with is their personality—specifically, how it affects the way they appear to others. As I’ve mentioned before, people who gravitate towards covert operations very often have backgrounds in military, law enforcement, or security, and many operators with this type of experience tend to unknowingly reveal themselves in subtle ways— thereby harming their covers.

When considering how to dress for a covert operation, many people reach for the clothes they’re used to wearing in their own real-life casual situations. The problem is that “casual” is a subjective idea that stems from (and therefore represents) your personality. And the personality of someone who’s dedicated enough to get into covert operations isn’t something you want to represent in your external appearance.

A common manifestation of this “casual” problem is the classic off-duty or low-profile agent look. It consists of jeans or cargoes, loose-fitting, untucked golf shirts or casual buttoned-up shirts (the kind that’re good for concealing a weapon) and sporty or otherwise comfortable walking shoes. This look is common among people who want to be casual but also want to feel comfortable enough to jump into action if things “go south.”

A few more easy giveaways I’ve seen over the years are tactical or sporty sunglasses (oftentimes Oakley’s), tactical shoes and backpacks (most notably 5.11s), G-Shock type watches, tactical-looking ruggedized cell phone cases, clip-on pocket knives, golf or polo shirts worn over undershirts (oftentimes the Under Armour brand), baseball caps, soft-shell jackets, and anything that’s considered “casual tactical” or “covert tactical.” The supposedly covert operator I mentioned at the beginning of this chapter had pretty much all of these things on him.

Am I saying that anyone who possesses these items is necessarily a covert operator? Not at all. In fact, I can safely say that the vast majority of people sporting this stuff are nothing of the sort. But as a covert operator, wearing any of these items can increase your risk of being detected as a potential operator. And if you also happen to have a somewhat serious disposition, and you’re occupying potential vantage points for long periods of time, you can get yourself detected as a definite operator.

I’ll be honest, the typical low-profile agent look is one that I like myself, but the fact that someone with my background and personality likes it is all the more reason to avoid it when working in the field. A good way to go about selecting what to put on is to consider whether you think something looks good on you. Odds are if you think it looks good, it’s probably because it fits and represents your personality, which means you should probably go change.

In the previous chapter, I talked about the benefits of the business-casual look. This advice can apply to other covert operations as well—depending on your cover and mission. But let’s expand a bit more on the idea of purposely not looking the part and wearing something that doesn’t represent who you are.

Most people have some articles of clothing in their house that they don’t like—how about that pair of fashion jeans that your significant other got you a while back? Or how about that silly-looking cardigan sweater that some well-meaning aunt got you for Christmas a few years ago? The fact that these clothes don’t suit your taste, and don’t suit your idea of what might look good for a tactical operation, is precisely why they will do such a good job of masking who you really are and what you’re doing.

This same principle also applies to your behavior, which we talked about earlier in the chapter. Conducting yourself in a way that looks dull or even somewhat dimwitted, as you slump down in your seat and play with your cell phone, might feel like the opposite of what you’re used to or what seems appropriate for important tactical operations. But, once again, that’s precisely what makes it so good for masking who you are and what you’re doing.

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Now that we’ve covered lessons and tips for working covertly in the field—including ways you can better blend in and remain hidden in plain sight—let’s turn our attention to how you can better detect if you yourself are being surveilled. In the chapter ahead, I’ll share some strategies to help you maneuver around certain types of surveillance and fill you in on a few tactics for evading watchful eyes.

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