Do you have any advice for writing characters undercover? Thanks!
So, we’ve covered this topic a lot in the past. Undercover operatives, intelligence agents, black ops, assassins, and spies I’d start with a spies search on our website, as that’ll get you started. The really good references will be there. My
big advice for writing any kind of spy fiction is to have a clear idea
of what you want and which genre you’re chasing. Do want James Bond or George Smiley? You can blend these genres, but it’s a good idea to have a clear idea as that’ll define your narrative.
The first thing to understand about spies and any sort of shadow operative is the Burn Notice quote: “A spy is just a criminal with a government paycheck.”
Take a look at this passage. This is a character (Thirteen) trained as
an undercover operative exiting a bad situation. What do you see?
Limping down the hall, I forced one foot before the other. Slowly, my stride lengthened. The silver door at the end didn’t open, so I pushed it, and stumbled out onto the launch pad. My gaze fell on a string of oval automatic airstreams parked all in a row. No, I frowned, eyes sweeping to street and the vehicles winging by in the air overhead. No self-respecting AI would let me drive in this condition. Robots always insisted on hospital, and I had no time to hack. To get out fast, I needed a human. A cabbie. Older, preferably female. Fingers to my neck, I tapped twice. Up came the ODS, my thoughts linking to: call a cab. Human.
A string of numbers and faces appeared before my eyes, the oldworld men and women working a dying industry. Better for No Questions Asked rides in our digital world, no one else called when they could pay a corporate run robot for half the cost.
I picked the first female face that flashed across my dash.
Time to pick up… thirty seconds.
I gripped my injured arm, and ran an analysis. Tucked out of sight, Sixteen’s pistol rested against my ribs. Ammunition at less than half a magazine, so seven rounds. Eight, if I counted the one in the chamber. The Uplink already registered the irreparable damage and severed the blood flow to the damaged limb. So, no more bleeding out. My upper lip curled. A bad trade off for no more arm. Damn, Sixteen.
I couldn’t hide in the shadows. Needed to seem desperate, distraught. Call up tears.
My blurred gaze flicked to the skyline, watching for black. The Ghosts wouldn’t appear in the datastream. Still, NIS hadn’t cut my access. Not yet.
A beat up airstream in ruby red dropped out of the sky to the left, pulling up to the curb. They were early. From the shabby state of their car, probably desperate. Good.
I limped over quickly. Even if they weren’t my ride, they were human and sitting in the driver’s seat. A car enthusiast who needed no AI systems to handle the steering. Likely to have built in cameras. More likely to possess a slow Uplink. Slow data received poor police service. My fingers seized the handle, flung open the door, and threw myself inside.
“Need a ride?” the voice was sympathetic, unfamiliar.
I slid across the bench into the seat behind the driver. My free hand tight on my damaged limb, couldn’t do much about my nose. So, instead, I tilted my head and caught her reflection in the mirror. Younger. Mid-thirties. Red hair worn short with one gray streak, tied back in a severe bun. Clear hazel eyes. Talk like you’re in pain, scared, but putting on a brave face. Tears. I wiped the blood from underneath my nose, sniffling. “Y-y-yeah.” I cleared my throat. “Yeah. Thanks.” I tried for a half-smile, half-grimace, and leaned on the window. “Just looking to get away. The address should be—”
“You don’t need to worry, I have it,” the driver said. “Came in with your order. Grace, right? You want to go downbelow, the Rep Shop.”
“Yeah.” Resting my cheek against the glass, I closed my eyes; Uplink sizing up her car’s systems. Automatic turned off, but easy enough to hijack. My free hand drifted off my injury, and moved near the pistol hilt jabbing my ribs.
“I’m Marla, I’ll be your driver today.” A pause followed. “You sure a pretty girl like you wants the Rep Shop? Not a hospital? You look pretty banged up.”
“No,” I replied. I got what she suggested, this was a nice neighborhood. “I just need… need to go…”
I grimaced, eyes squeezing shut, and wished I felt a twinge of guilt. It’s like the Overseer always says, love is just a cover.
“Don’t worry, no need to say it,” Marla said as the engine revved, the floorplates shook, and the airstream lifted skyward. “Shipped enough victims out of here to know.”
Notice, she pays attention to her surroundings and makes choices based on her condition in service of her needs. She needs to get out quickly, but would run into more trouble stealing a car so she calls up a cab driven by a human. Human’s are easier to manipulate in short order than code cracking. She specifically aims for a female cab driver, one preferably older than she is.
She’s female. Another woman is more likely to assume her injuries are because of a man, and a cab driver will have encountered this scenario often enough to not pry too deeply into it. An older woman is likelier to be maternal and protective, but not so protective that she’ll stay beyond when Thirteen needs her too. However, pay attention to the fact that Thirteen never verbally confirms it was a man who caused her injuries. She lets Marla assume, and fill in the blanks herself. This gives her an out later if she needs to change her story and place the blame on Marla’s shoulders for misunderstanding.
This is an example of what’s called social engineering.
Deliberately manipulating the people in your environment to divulge
confidential information or getting them to do what you want.
Notice also: After getting into the vehicle, Thirteen’s hand goes to the gun she stole. As she is playing to Marla’s sympathies, she is also assessing the possibility of killing this woman and taking control of the car if things don’t go the way she’s planned. Thirteen would prefer to exit by the easiest means possible, but a good spy always has a contingency. She won’t compromise her safety, and civilian lives mean next to nothing. A dead body is one more problem to deal with, one more attention getter that she doesn’t want, but she’ll go there. Violence is messy, and sometimes necessary.
There’s no real difference between a spy and a conman. Still, if you want to trick people there’s a few rules to follow.
What a spy isn’t:
A compulsive liar, an overseller, or lies all the time. An undercover operative needs to maintain their identity, that is one identity, singular. While a spy can create many false personalities, they should only be using one at a time with the goal of giving away as little information in trade as possible.
Notice: Thirteen does not tell Marla a story, she lets Marla create the story and then plays along. It is easier to convince someone of a lie when they’ll craft it themselves. Why say something when you can get just as much by saying nothing at all?
“You’ve told her three lies. Suppose she’s an asset, now you have to make all three lies true.” - Spy Game
Your character can’t just lie, a liar will be caught after a prolonged period of time. They need to manipulate the truth by creating a fiction. A cover is a fictional person with a fictional job who people think really exists when they check the character’s identity. Assume their identity will be checked, re-checked, and checked again. They are not maintaining a cover to a singular individual, but multiple ones. Their assets are the locals they are manipulating in order gain access to information, and who often run the jobs for them. These assets will, most of the time, not know the truth or not know the whole truth about who the spy really is.
Assets can be friends, business associates, girlfriends/boyfriends, wives/husbands, disgruntled employees, janitors, etc.
Your character can’t enter a business or government agency as a pretend janitor if they’re also going there everyday as a reporter or contractor or some other job. They must maintain the fiction of their identity.
This is the biggest problem most authors will get into when writing spy fiction. The concept of telling lies is something that comes easily to most of us, the problem comes in with keeping up a fiction over a prolonged period of time. The next step is to be able to lie without guilt and throw over people who help you without remorse. Crafting that dual identity of a person who genuinely cares about their friends and allies versus the real one who… really doesn’t.
You need a solid grasp of social functions, mores, and conventions in order to write a spy because a spy is manipulating all those points to gain access. You also need to understand these rules change based on what society your character is entering. Social rules change based on social groups, be it economic or cultural. The expectations for a man or woman in Mexico City versus Seattle are vast, and your character needs to be versed in the world they’re walking into. They need a cover identity to suit their work. Someone who has the freedom to go many places without being questioned, but unimportant enough to be neither needed nor remembered.
A spy is always looking for a way in, to slide into your confidences or sympathies however they can. They are going to use you to get where they need to go. They are very convincing actors and they are changing, modifying themselves slightly for each person they encounter. Not so much though that their falseness becomes obvious to the other people who know them.
When we’re working with a female spy, for example, all the “bad woman” societal traits you’re inclined to throw away are exactly what she needs to succeed. She will flirt, and flatter, and seduce, and manipulate the men (and women) around her to gain entry. She may rotate between being a gorgeous woman and an unremarkable one by the use of fashion and makeup. She is exactly what so many men are afraid of, a social climber who is manipulating their feelings and her attractiveness in order to get what she wants because it is the most expedient method to get what she needs. The one who is manipulating society’s view of women as nonentities, nonthreatening/replaceable objects in order to do her job.
Don’t be afraid of these characters. Don’t be afraid of “unlikeable” characters.
Spies are bad people who do bad things. They are often cold, calculating, impersonal manipulators looking for the most expedient method to get what they need. Your spy’s cover is just a cover. Never forget the real person underneath, especially when they’re lying to themselves.
James Bond is a pop culture juggernaut, but even obsessive fans have trouble keeping track of the secret agent’s complicated history of over dozens of films. Here’s what you need to know about the iconic man of mystery.
James Bond makes men sit down by using a gun: Everyone knows that the superspy travels around the world to make men sit down, but how does he make them sit down? James Bond’s secret weapon is the gun, a kind of gentleman’s sword. He often uses his gun after uttering the classic catchphrase, “Please seat yourself anywhere.”
All the incarnations of James Bond are brothers and live together in a studio apartment: Here’s one of the more obscure bits of Bond mythology. All the James Bonds—from the Sean Connery James Bond to the Daniel Craig James Bond—are brothers who were given the same first name by their parents. To save money after moving to London and joining MI6, they rented a studio apartment where they all sleep together in a single king-sized bed, except for the Roger Moore James Bond, who sleeps on the floor in a sleeping bag because there isn’t room for him.
Bond’s code number 007 is a reference to 7: Author Ian Fleming didn’t pick 007 at random. Most viewers don’t realize that it’s intended as a clever nod to the number 7.
James Bond doesn’t understand that humanity is weak and corrupt and that the Earth must be purged so a better world can be built on society’s ashes: The fool, Bond can’t see that, like a forest fire allowing fresh saplings to grow, civilization must be swept away to make room for a utopia. Disgusting sheep, that’s what most people are, living their tedious lives, mindlessly destroying their environment in pursuit of the almighty dollar. It would be a favor to burn them all away, like the ants they are, and allow a select group of genetically superior humans to repopulate the planet, but Bond doesn’t have the vision to embrace what needs to be done.
Jason Bourne is pretty much the same thing: One of the best thing about James Bond is that he’s basically Jason Bourne. You can nitpick ways that they’re slightly different, but they’re essentially identical. James Bond being more or less Jason Bourne is what theatergoers have loved about Bond for over 50 years!
How realistic is it for the retired agent/spy/assassin to come back and kick just as much butt as they did years before? Does such training come back to you easily if you haven't used it in a long while or will you be rusty enough to get killed?
Parts of this are realistic, others not so much.
If you’ve spent enough time training techniques, this stuff
gets baked into the way you move. It’s not, “oh, I’ll do this to someone;” it’s
just there. Training can also affect
how you look at the world; this is true as a general statement on life, but it also
applies here. Again, as with muscle memory, this is always there, always affecting
how you view your surroundings and the people in them.
So, in that sense, yes. A veteran character coming back after
years away from the job will still
have their skills and training. Some of that will be rusty, but this stuff
sticks with you. Especially if you were maintaining your training for years.
That said, they’ll still get their teeth kicked in.
Ironically, one of the more realistic takes I’ve seen on this
was in the middle seasons of 24. In
the early seasons, the protagonist, Jack Bauer, is a federal counterterrorist
agent. After the third season he’s basically on his own, and no longer a part
of the agency that trained him. By the fifth season (about 3 years later) he’s
at a point where he’s getting his ass handed to him by a security guard.
The problem is something we’ve explained, repeatedly. Hand to
hand combat is not static. The training I got 20 years ago doesn’t apply now.
It will work against untrained
opponents. Basic physiology doesn’t change. However, going up against opponents
who’ve been keeping their training up to date, (or are some of the people
responsible for updating the techniques in the first place), is not going to
Something I know we haven’t discussed on this subject is how
this updating happens. It requires contact with people who are actually using
their training practically. Seeing what people are doing isn’t something that
you can do sitting on a mountain top. You need to actually be immersed in the
community. You look for how people are adapting to the techniques you’re
training others in, and look for ways to get around those counters.
In the case of law enforcement, one major source if
intelligence to guide updates is watching what criminals are teaching each
other in prison. Career criminals will look for ways to counter police hand to
hand, and once they have that, will (usually) share it with people they work and/or
A veteran coming in after years away may be able to execute
their training perfectly, and still get taken down by a rookie who received
their training last year, because they were trained to counter the veteran’s
Updating is about looking for the things that are most prevalent,
and finding ways to defend against them. It’s very likely your veteran will
understand this concept. Whether that affects their behavior is more of a
Incidentally, this doesn’t just apply to hand to hand, it’s
also a relevant concept when you’re talking about things like tradecraft.
Tradecraft is the shorthand for techniques used in
intelligence gathering. It’s (somewhat) all encompassing. So, anything from
social engineering to dead drops or even the way you set up surveillance could
be lumped in under this header.
Just like hand to hand training, this stuff does go out of
date. Usually once someone’s actually exploited a method and gotten caught
doing it. Though, sometimes it’s preventative.
The irony is, when it comes to being a spy, the biggest
problem is being a veteran, not being out of practice. It’s being a veteran. When
a spy starts their career, no one knows who they are, they have no reputation,
they’ve never turned up in strange places, they’re just someone walking around,
taking in the sights, maybe doing a job for some NGO.
Even if a spy is never caught, as they work, their name will
start ending up on desks, in lists of witnesses, employees, or whatever. Once
is not a pattern, but as their name keeps coming up over the years, it becomes
easier to identify them. Potential enemies start keeping files, and gradually
filling them with what they know. This means it is much harder for a veteran spy to operate in the field undetected,
than it is for a rookie.
There’s a similar issue for assassins. Either they’re a
complete ghost, no one knows who they are, and may not even believe they ever
existed, or (more likely), if they were working for a government (or any other
large, overt organization, like a corporation), they’re in the same boat as a veteran
spy. People may not know your character is an assassin, but they will know that
they worked for someone. Which in
turn, will put them on guard, and make your character’s life much harder.
There are concepts a veteran will have internalized, which
someone without training won’t understand or grasp. Thing that just don’t go
out of style. For example, bullets will blow through most residential walls and
furniture. So, if someone’s taking cover behind a couch, kitchen wall, or car
door, it’s far more expedient to simply shoot through whatever’s in your way.
Another concept is one I’ve mentioned recently, you reload when you have the
time, not when you’ve run your gun dry.
Similarly, experience they’ve learned from may still be relevant.
Being able to read someone’s intentions, know when they’re about to resort to
violence, or simply knowing the value of good intelligence aren’t going to go
away because your character spent the last five years pretending to be a well-adjusted
Hi there! I love your blog! I've seen you mention a few TV shows and movies for research, and I was wondering what your opinion is on the show Leverage and it's accuracy for social engineering in potentially violent situations. I remember one character saying that "Thieves look for entrances, but grifters create them." They'll often use approaches like this to avoid violence.
If the question is: can you use social engineering in order to defuse or avoid violent situations? The answer is yes.
Grifters are conmen, and like spies, they don’t want to fight unless it is absolutely necessary. Whether they can fight or know how isn’t really the point: combat makes messes, big messes, and draws the kind of attention they don’t want/can’t afford.
As for the line, “thieves look for entrances, but grifters create them” the point of it is that grifters focus on people as the exploitative aspect to get what they want. After all, it doesn’t matter how good your security system is if your infiltrator is expected to be there. When someone opens the door for them, they didn’t have to break in.
It is worth pointing out though, being able to stop, defuse, avoid, or redirect violence via social engineering (especially when the character is the target) is very difficult and requires someone who excels at rapidly changing their story/manipulating under life or death pressure while also maintaining their consistency/re-establishing their innocence/regaining their target’s trust.
That’s masterclass social engineering. The average person, even the average grifter can’t do it. When we see Nate Ford, Sophie Devereaux, or Michael Westen on Burn Notice socially engineer their way out of potentially explosive and violent scenarios, we’re supposed to understand this level of manipulation is very difficult. You need a solid ability to read people, predict their behavior patterns, understand how to shift your role so you suddenly seem trustworthy, confuse them, and then redirect their anger somewhere away from you.
You can see another variant of this kind of social engineering on display in The Negotiator. Samuel L. Jackson’s character is a hostage negotiator. Deliberately maneuvering a man who’s taken a child captive around his apartment so he can be taken out. You can see him joking with the target, gaining his trust, distracting him, and guiding him off topic until he’s in a position to be neutralized.
The Grifter is not a fighter, they are a talker and their trick is getting people to move however they want. A skilled grifter can slip in, turn the best of friends against each other, and walk away without a care. Grifters don’t punch. They trick other people into doing the punching for them. When sitting down to write a Grifter, remember: their first instinct is getting others to act in their place, to create the openings they need, and be their fall guy.
On the whole, I’ve liked Leverage ever since the episode where Eliot pointed out that guns are ranged weapons, and the most common mistake people make is giving up the distance advantage by getting in too close. However, I’ve only watched the first season. I liked what I saw, it’s an enjoyable caper show in a similar vein to The Equalizer, Person of Interest, or Ocean’s Eleven. Not quite in there with the original Law & Order when it comes to accuracy (in this case for cops) but certainly better than White Collar, which uses similar techniques (though never, ever pay attention to White Collar’s usage of the FBI… ever). The X-Files, meanwhile, fudges a bit but it’s pretty good when you’re wanting to get a grasp of the FBI’s culture and what happens to someone who doesn’t come from a military/law enforcement background.
Of course, the patient zero for these types of shows is the original Mission: Impossible. The television show, not the Tom Cruise movies. Mission: Impossible is all about flipping people and manipulating them into positions to do what you want. The A-Team is its slightly more pulpy counterpart, but its a similar (though far less subtle) deal.
On the whole, Leverage tends to explain itself better, which is helpful when you’re trying to learn or take techniques from a television show rather than just absorb.
The reason why I often suggest Burn Notice and Spy Game is not necessarily just because they’re good, but also because they teach. The narrator on Burn Notice, especially in the first season will offer up a lot of helpful/beginner tradecraft for a variety of situations. This, ultimately, will help you more for taking pieces and creating your own characters than a show that’s trying for smoke and mirrors like White Collar. The same situation is there with Spy Game, where Robert Redford’s character is teaching Brad Pitt’s on how to be a spy. Ultimately, more helpful in the long run than just watching The Recruit. The Michael Mann films like Heat and Collateral are exceptionally good for learning tradecraft, but you have to know that’s what you’re watching/looking for. You’ll learn more by watching them together, rather than separately.The Borne Identitynovels are also very good at showing the tradecraft, while the Le Carre ones tend to be a little more hit and miss.
When you’re new, you want sources that are free with their information. Who are good at getting you to think, to take what you’re seeing and apply it to new settings. You may not ever figure out how to build a car bomb, but learning about how the thought process of a spy, criminal, or conman works will serve you better for your writing than a hundred other movies that only show.
After you’ve drawn back the curtain then you can turn to those other shows, novels, and narratives with new eyes. Once you see what they’re doing, how they’re doing it, and why when they don’t explain you’ll get more out of those other sources than you did before.
When you’re watching a well put together show like Leverage, start questioning character motivations. Not just whether the social engineering there works, but why the characters are choosing to go that route or which routes they prefer. Leverage gives you five characters with different specialties, four thieves and the guy who made a career catching them. They all think in different ways and have different approaches when it comes to problem solving. Leverage offers up a heist per episode, so you have lots of opportunities to see the characters in action. Evaluate their problem solving methods and you’ll come away with more than just questioning whether or not it works.
How and Why.
Then, go find a good video on YouTube where a professional magician explains pickpocketing. It’s the art of misdirection.
Once you understand basic theoretical underpinnings (whether or not you could ever actually pull the real thing off) then you can apply it to many different situations in a fictional context.
When it comes back to applying this to the combat arts, learning to see the big picture is the first major difference between trained and untrained. The untrained only copy surface level, singular techniques, while trained delves deeper to understand how these techniques work together.
My advice for when you’re wanting to pick and choose television shows for accuracy is to check who their consultants are/were, and what experts in the show’s chosen field say about it. That doesn’t always guarantee accuracy, but it will help you flip through the rave reviews.
If you want to watch more fun shows with Timothy Hutton or just like detective shows, I recommend Nero Wolfe.
Anonymous said:could I get some prompts about being on the run from the mafia?
Anonymous said:Any spy prompts? //
Anonymous said:Do you have any prompts about spies?
Anonymous said:Could I please get some prompts for a situation where the hero decides the best way to fight the villain is to infiltrate the villain`s organization, then blows his/her cover? Please? And thank you for all the great prompts, you are my best inspiration :)
1) “What do you mean you have to go?!” They grabbed hold of the other, utterly bewildered. “Where’s this coming from?” They barely recognized them now - kind face gone cold, clinical, a stranger’s face to them. “I’m sorry.“ The other yanked away. “But there are - there are things I haven’t told you. Couldn’t tell you. And now they’ve found me.” The other looked at them, anguished. “You’re dead if I stay.” “What the hell are you talking about!?”
2) “We’ve got something of yours,” said the voice on the phone. “If you’d like it back, I suggest you follow our next instructions very carefully. They’re just dying to see you again.”
3) The spy flung themselves on the back of the motorbike, wrapping their arms around the other as they screeched away down the narrow streets. “Good timing,” they managed. “I told you not to ruin my bloody equipment.”
4) “You’re a spy.” The shock reverberated through them and turned them clammy. They’d thought - they’d thought - Their lover smiled and trailed finger’s down their chest. “Of course I am. So are you. I was your mission, you were mine. It’s almost even romantic, no?” They tugged against the cuffs, heart rabbit-racing in their chest. “Poor thing, you got attached didn’t you? All protective of your charge?” They smiled at the look on the spy’s face at that, at the desperate way they were trying to cobble their defenses together again.
5) The villain examining them, jaw clenched, betrayed. The protagonist expected some comment on lies, on ‘I trusted you’, some lost tone perhaps or maybe an immediate order for their execution. They didn’t expect the way the villain’s brow furrowed, as they leaned in. “Why would you blow your cover for that? You could have won,” they said. “How could that have possibly been worth it?”
6) “We’ve got a rat for you.” They were tossed down before the villain, landing hard, ears still ringing from the fight. The villain didn’t look up. “You know my policy on rats and extermination.” “You’ll want to see this one though.” The villain raised their gaze, and went still. Their eyes locked. The villain straightened. “Oh, now that’s a shame. You were one of my favourites too.”
7) “I imagine it will be difficult for you to crawl back to your master’s with no kneecaps,” they said pleasantly. “What do you reckon?” “Things have changed-” They didn’t get the opportunity to finish.
8) They took one look at the cars pulling in around the flat and bolted. Grabbed their always ready to go bag and hurtled down the corridor, running logistics, escape routes, how many bullets they had versus how many men. How had they found them? They even got quite far, before they were caught around the waist. Tasered. Hitting the ground, shuddering. A shoe pressed on the back of their neck. “You should be flattered - I don’t normally come personally. But I thought I would make an exception for you.” Their insides turned cold.
Agent Derek Hale has been working up the courage to ask his partner Stiles out on a date (finally!) when he heads out on a solo mission—without Derek. Eager to provide support, Derek arrives in Beacon Hills, only there is no mission, and Stiles’ dad thinks Derek is Stiles’ boyfriend. Well. It could be worse.