Covert Operator: 10 Signs You Might Be A Gray Man

If you have had any involvement or fascination with special missions, clandestine services or even protective operations, you may have heard of the term the “gray man.” (For the purposes of simplicity, we are using the term “gray man” and not “gray woman,” “gray lady” or “gray them/theirs”—no offense.) Like with many other terms in the “operator” space, there are different ideas about what constitutes a gray man. 


Gray Man Skills

In clandestine operations, being the gray man often comes with the job. Your outward manner, appearance and actions are conceived and carried out so as not to compromise the true purpose of your cover story, your reason for being at a particular location or your activity. Being a gray man is often a state of mind and being, wherein one is projecting that they know nothing or don’t have any specific details about anything. One’s natural bearing is suppressed so as not to send out any signals that you are actually an alpha-dog operator, an undercover cop or a protective agent.

Some people have personalities and dispositions that make them almost naturally to be a gray man (more on this later), and others may have to spend lots of time unlearning how they learned to be a badass at Parris Island or elsewhere.

Being the gray man is not just for the tactical operator or clandestine officer. For example, consider a uniformed security officer (an overt and public-facing job) who is asked a number of questions by a passerby.


Hours On The Job

“How many hours are you usually on shift”?

“Do you have other officers on shift with you”?

“Is anybody armed?”

One can tell from these questions that the passerby is seeking to elicit protected information from the security officer, but if the officer is properly trained, he or she will present an opaque front to the passerby and deflect the questions as a “gray man,” perhaps with responses like “It varies” or “It depends.” The inquisitive passerby is not extracting any actionable intelligence and will most likely move on to elsewhere.

If the officer is really on their “A game,” then he or she may turn the questions around and ask of the suspicious person, “You sound like you are interested in working here; why don’t you give me your name and number and we will contact you.” Even with the less-than-sexy job of a uniformed security officer, there is an opportunity to deploy some gray man skills to protect information from being exploited by an untrusted individual. Obviously, gray man skills are critical for protecting operational security (OPSEC).


Appearance Is Everything

The other means of being a gray man is manifested through one’s physical appearance. If your job is as a surveillance detection agent and you have big strapping muscles, cargo pants, sunglasses and tattoos up and down your arms, you are going to stand out unless you are in an environment where others dress and look similar to you—like at the SHOT Show.

A gray man blends into his environment. If your job has any covert element to it, your success revolves around you being as nondescript as possible, so no one really remembers seeing you or having any impression about you one way or the other. A soft-looking, unassuming “snowflake” may be the guy whose role it is to take surveillance photos of a terrorist financier in Zurich, Switzerland.

The gray man also understands local culture, mannerisms and dress. Even if one’s cover is as a tourist, sometimes being the “ugly American” fits into the narrative of what the adversary or host government thinks of every other American, and your presence and actions are dismissed as normal.


When Hollywood Comes Calling

As we have seen with the fanboy hysteria of being “an operator,” being the gray man has its share of fandom too. In fact, a number of security consulting firms use the “gray man” motif or name. Former Tom Clancy collaborator, novelist Mark Greaney, wrote a book in 2007 titled The Gray Man and a subsequent series of novels, which will soon be released as a Netflix movie starring Ryan Gosling and Chris Evans. Hopefully, the producers and directors will make the stars look like regular schnooks and not dashing secret agents. One of the best movies that demonstrated gray man skills was The Day of the Jackal (1973). The assassin in the movie was so bland, yet he operated like a chameleon, and ultimately no one knew where he was from or what his real name was.


Everybody’s A Comedian

For those of you wondering if you have those innate abilities or looks to be a gray man, below is a little checklist in the spirit of Jeff Foxworthy.

You might be a gray man if …

  • Your childhood friends forgot about you when playing hide and seek.
  • Your teacher keeps asking you what your name is four months into the school year.
  • People can’t decide if you are Hispanic, Greek, Italian, Middle Eastern or of a mixed lineage.
  • You never got into fights because of your quiet confidence and small ego.
  • Maybe you always won games of capture the flag.
  • Always able to sneak into bars, clubs and lounges underage because you  piggybacked behind a group of 30-somethings while your friends got busted with fake IDs.
  • Your dad never realized that you borrowed his porn collection for years.
  • Your parents always blamed your siblings first for things you did.
  • You know so much about other people and events, but no one knows anything about you.
  • Each of your five best friends would describe you in five different ways, with no firm consensus of who you actually are.


By Greg Schneider, July 13, 2021, published on SKILLSERT

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