I spent nearly two decades at CIA and left just before the Taliban came back to power. When Kabul fell in August 2021, I was on vacation in France with my one-year-old son. I set up a makeshift command center in our Airbnb’s bathroom, and for two weeks worked phonelines with former colleagues, interpreters, and volunteers to ferry out Afghans who had assisted the U.S. Government.

This Mother’s Day, I want to write about three mothers from that time.

It was just past midnight and I had crawled into bed, desperate to sleep after hours of working exfiltration plans. I picked up my phone one last time and scrolled through a Slack channel of volunteers and saw: U.S. citizen baby stuck in Kabul. I lay there with my eyes closed, telling myself someone else could handle it. But I couldn’t turn my brain off. All I could think about was my own child sleeping peacefully in the next room.

The baby had a U.S. passport but her mother didn’t. She was four months old. To protect her identity, we’ll call her Zahra. Her father was a former U.S. military interpreter. He was in the United States while Zahra and her mother were in Kabul. The mother was unable to get close enough to the airport gates to hold up Zahra’s U.S. passport for safe passage.

The Kabul airport in late August 2021 was bedlam. Thousands of people desperate to enter the airport created chokepoints everywhere. This, along with roving Taliban gangs, made it so people were unable to get close enough to American soldiers guarding the gates for entry. A suicide bomber had killed 180 people outside one of the gates a few days earlier.

The only viable solution was a very selective one, given how many people were rushing the compound. It was a secret gate operated by the CIA. But even that gate was dangerous. The U.S.-affiliated Afghan guards working that gate fired warning shots into the air at anyone approaching as crowd control.

I promised Zahra’s mother they wouldn’t actually shoot her or the baby, even with guns aimed and firing just above their heads.

Share

I had told Zahra’s father explicitly: only the mother and daughter would be allowed entry. When they arrived at the gate, they had Zahra’s uncle in tow, pleading that he be added to the flight manifest to the United States. I had to keep telling them no. Only the wife and baby.

The clock was running out. Afghan men traditionally wield heavy control over their families, and Zahra’s father wasn’t letting his wife and daughter pass through the gate without the uncle. So I had to send this message:

“You hold your world in your hands. You are in charge of your family. You know as well as I do that there are two types of people in this world. Those who wait and those who act. You are the type of person who acts. This is your wife and daughter’s last chance and you hold their future in your hands. If you don’t let your wife and child walk through that open airport gate right now, they will never get a second chance. Your little girl will grow up under Taliban rule and never know her father. You can’t go back. You’ll be killed. They might be killed because of you. I pledge that I will not forget your brother. I will do all in my power to help him. But he will not walk through that gate right now. I’ve spoken to the American soldier and it is not possible and there is nothing that will make it possible. You have only two options right now, and they aren’t negotiable. Let your wife and child proceed. Or leave them behind forever.”

He let them through. Imagine the bravery of Zahra’s mother, pleading with her husband and walking toward gunfire. All for the hope of a future for Zahra outside Taliban rule. A few hours later, Zahra’s mother sent me a picture of her and the baby onboard a U.S. military aircraft. Fortunately, they made it out.

That same week, another family wouldn’t walk through to the gate. They were too terrified of the guards’ guns. I argued with them for thirty minutes, every angle I could think of. I went to the next family on my list. The father was a U.S. Green Card holder. He had sent me a family photo that day, with his Green Card in hand for verification, taken near the CIA gate, along with his wife and three children, all under six years of age. One was a young girl. As I was telling that family it was their turn to walk, the Taliban took over the gates and they didn’t make it through. This second mother now has to raise her daughter under Taliban rule.

That family’s photo is still in my phone’s photo album and sometimes it pops up on my phone’s home screen. I don’t delete it because I don’t want to forget what’s at stake. This is what authoritarianism does. It forces impossible choices.

The third mother I think about on Mother’s Day is one I’ve not met. Her daughter, we’ll call her Zoya to protect her identity, was a 25-year-old NGO worker when Kabul fell.

Because of her strong English skills helping U.S. military contacts and because she provided a safehouse for my CIA interpreter’s family through a network of volunteers, Zoya was offered a way out alone, without her family. She had less than a day to decide. When first offered this opportunity, she told us no. But then she talked to her mother.

Her mother told her she had to go to the United States. That Zoya wasn’t meant for a life under the Taliban. Because the Taliban were moving in quickly to take control of the airport, Zoya had to leave in such a rush that she couldn’t say goodbye to her siblings. Her father got her as far as he could before the streets were blocked and then she ran half a mile through Kabul to make the gate before it closed. Zoya has since graduated from a top American university with a master’s degree. She is building a life here but hasn’t seen her mother and the rest of her family since that tearful goodbye.

A mother passing her baby over a wall. A mother telling her daughter to leave knowing they may never see each other again. A mother trying to get her child out from under Taliban rule. This is the depth of desperation. It is also the depth of love. It is also what authoritarianism makes mothers do.

Subscribe now

My son is nearly six now. I tell him America is a country worth being proud of. It is a country worth fighting for. That our great American experiment is durable if we are.

I spent parts of my life in places where authoritarianism is alive and well. I have seen the toll of being jailed or sent to a labor camp for failing to sufficiently praise a country’s leader. I have seen parents whose child was murdered for something as simple as going to school. Sometimes it takes living under authoritarian rule, having to hide, having to compartment aspects of your life, having to go along to get along, to really understand the stakes of creeping authoritarianism.

Many Americans do not understand how good we have it because they have never lived under a dictatorship. The far left is sometimes right about American failures. Where they go wrong is in treating every failure as evidence that the whole project is bad. America is imperfect. That is different from America being broken. Acknowledging what we’ve done wrong is part of becoming better. Treating it as the whole story is how a country talks itself into giving up on itself.

What I worry about most is creeping authoritarianism in America, presented as the solution to our growing polarization. We speak in a language of victimhood and outrage on both sides of the aisle. The biggest threat is that Americans give up on each other. That cynicism can become the operating system of the country if we let it.

I worked in countries where the state routinely called its critics terrorists. Their enforcers didn’t need masks because they had the full backing of the regime. America isn’t there. But when masked federal agents kill Americans in our streets and the reflex is to call the dead domestic terrorists before any facts are in, we have taken a step toward it. We should be very wary of this road.

The march toward authoritarianism doesn’t always announce itself. Some of it is loud, like a killing in the street. Some of it is quieter. It looks like using the courts as a weapon against political opponents instead of a venue for justice. It looks like demanding the right vocabulary before we will hear anyone out. It looks like treating speech as if it were violence, then using that as a license to silence anyone whose views make us uncomfortable. It looks like treating the most extreme example of the other side as proof of what everyone on that side believes.

Some of these are small on their own. But stacked together, over years, this is how a country forgets how to be a country. It is how Americans give up on each other.

It would be sky-is-falling to say we are setting ourselves up for Taliban-style rule. It would also be inaccurate. The risk is something quieter but still un-American. The slow erosion of the thing that makes the United States the place foreign mothers tell their children to walk toward even at gunpoint.

What makes us great is exactly what those mothers were trying to reach. The expectation that a child can grow up safe and have it better than her parents had it.

Mothers have always sacrificed for their children. Afghan mothers walked toward gunfire. The sacrifice this moment asks of American mothers is quieter. It’s refusing to write off half the country. It’s not cheering when the law gets weaponized against someone we don’t like. It’s keeping our common sense when the loudest voices on every side want us to lose it. It’s raising children who can disagree with someone without trying to destroy them.

The defense of the republic has historically been the work of men. Most of the soldiers in most of the wars have been men. The writers of the Constitution were men. Women often get labeled as the soft gender. Too forgiving on immigration. Too quick to sympathize. Too quick to extend a hand to an adversary that would just as soon take it off. Too optimistic to see the hard truths of great power competition.

Some of that critique may carry truth. Coming from CIA and being around our military, however, it is clear to me that American mothers have and continue to take up arms for their country and for their children. There are mothers out there right now on the front lines, some in the shadows at CIA, willing to die not just for our children, but for the country they want to pass on to them.

And we are not soft about our children and their future.

We aren’t soft about a future where they have to practice active shooter drills in school. We aren’t soft about a future where the freedoms our grandparents fought for get traded away by a generation that didn’t earn them.

The work of keeping the republic falls to mothers as much as fathers now. We have voices and we need to be loud. Our children will inherit this country and we need to be clear with them about what is theirs to defend. We need to raise our children to know the difference between a flawed republic and a strongman, and to choose the republic every time.

Somewhere a mother is still holding a baby, hoping there is a country in this world that gives her child a reason to hope. Ours should be that country.

The fathers founded the republic. The mothers may be the ones who keep it.

Happy Mother’s Day.

Subscribe now

*Inside CIA, Episode 3, available on Disney and Hulu, covers the exfiltrations mentioned here.

1. Find the technical expert. Take the type of technology you’re researching, and anything in particular the company claims is their special approach to it, and combine it with the below search terms: “national lab,” “AFRL, “ARL,” “NRL,” “AFRL,” “DARPA,” “NSWC,” “ONR,” “MITRE,” "JPL" and “RAND” to see who has written on it from those entities. Or go to those websites and try to find if that technology is listed and the associated expert.

You can also use the technology search terms and pull experts’ names from papers published on https://arxiv.org, but just because something appears on the arXiv doesn’t mean it’s peer-reviewed or fact-checked. Even for “peer-reviewed” publications, there is a lot of gaming the system. Yes, landing an article in “Nature” is great for a company, but I would never take it as Gospel. Google “room temperature superconductors and Nature” as an example.

Don’t contact the world’s foremost experts [real or perceived as blessed by the media] asking for their time. Examples of this would be Yann LeCun for AI/ML, Scott Aaronson for quantum computing. You can try, but I think it’s a waste of your time because they’ll likely ignore you or say no.

Share

2. Contact the expert.

The people you find above will be somewhat neutral, third-party experts. My first stop for outreach would be LinkedIn, though you can find some government emails on sites like Hunter.io and Rocketreach.com.

The challenge with emailing someone at their government email is they can become paranoid about engaging with you for fear of conflicts of interest. The government has to cater to the lowest common denominator of employees, because someone at some point has done something so stupid, unethical, and illegal that a bureaucrat felt they needed to write a regulation to prevent it in the future. Because most government workers want to stay within regulatory bounds, they go overboard in being cautious. (If you’re a government employee, you know this all too well!) So try to message them on a third party platform first. If you don’t get traction there, then send an email. Don't email their personal address unless you can name drop that a mutual party provided you their contact information.

Here is an example of how I would conduct outreach for the best chance of a response:

Title: Feedback on your paper/quote/article “Laser diodes on sharks”

Hi Dr. Powers,

I recently came across your paper about laser diodes mounted on sharks. I’m a current US Government employee at X (if you can say) looking to make the jump into the private sector. I’ve been talking to a few people in this field (as you go, start name dropping people you’ve spoken with for validation, but don’t lie) to vet the technology before I make the jump.

Your paper/article mentions that the biggest challenge/opportunity/question with the technology is the lasers. If you’re open to it, I’d like to ask a few follow-up questions, such as your assessment of [insert something else in a paper or research area that they or others have mentioned online].

Please let me know if you’re willing to set up a 30-minute call over the next few weeks. You can reach me via this email or my cell at 202-555-5555. I’m happy to send a few of my questions in advance.

Thanks,

Your name

3. Ask the expert questions.

You must put in your own effort here. Don’t waste your time and theirs if you haven’t spent a couple of hours watching YouTube videos and reading papers about the technology - at the least. Showing up to ask them to explain the basics of a technology is a waste of precious time that you could be using to advance your networking & actual knowledge (as described below). Plus, without any baseline, you have zero context of where to take the conversation based on the answers.

It should go without saying that you shouldn’t launch into an interrogation, so short pleasantries and your introduction are appropriate. Do explain what you do now, how you’re looking to make the jump, and on what timeline, why this technology appeals to you, and offer a bit of praise for their work, but not too much since you (and they) know you really don’t know what you’re talking about.

In the pleasantries, try to discern if there is anything of value, even if it is your own personal perspective from X government agency, that you can offer subtly in exchange during the conversation. There is probably nothing of value for you to offer them and that’s okay. Don’t force what isn’t there. In most cases, what you’re offering them is an ego boost that you read their work and have questions.

Also, ask these questions:

• I can imagine there are detractors in the field who believe this technology won’t work or be able to make the jump out of the lab and into real-world use. Who are they and what are their arguments on why it won’t work? What’s your view on the validity of each?

• Who do people in this space consider some of the foremost experts and why?

• What do people looking to commercialize this technology usually miss or get wrong?

• What do the media and outsiders often get wrong about the technology and its readiness for commercialization?

As you get further into the conversation and get more comfortable with each other:

• What are the companies out there working on this technology and what’s your assessment of them?

• Which companies would you steer clear of and why?

• So which companies do you think are largely approaching this the right way? [let them answer] Do you know anyone there? [let them answer; once they share, it’s easier for you to make an “ask” and harder for them to say no] What about the other experts you mentioned?

Subscribe now

4. Ask the expert to introduce you to other experts.

Script continued:

Would you be willing to introduce me to them?

[Comment: I know sometimes it feels hard to ask so directly, but if you don’t ask, you won’t get an intro. If you’re too embarrassed, and/or the conversation has been stilted, you can pivot to the below. It’s best to make the ask in the flow of conversation - don’t let there be a gap between the end of #3 above and this ask.]

“The experts [or company rep] that you mentioned…What’s the best way for me to get in touch with them?

Assuming they say email

Do you have their email? [Assuming they say yes] Great, can you provide it to me? I’ll write it down here right now so I don’t forget. [Try not to give them time to say they’ll look it up and send later because they probably won’t].

In my experience, when asked any question, no matter how sensitive or controversial, most people feel obligated to answer. You just have to ask.

5. Send a thank you message.

Be polite. It’s the nice thing to do and you may be calling upon them again. Or they may encounter representatives of the companies you're interested in and pass them your name.

This isn't rocket science. But obvious things can also be difficult.

1. If you have an in-house physicist, don't use them for most of your technical diligence. Sounds crazy, right? The field of physics is vast; PhD expertise in one area does not confer knowledge in other areas. A PhD in physics isn't a panacea. A PhD in atomic, molecular, and optical (AMO) physics, for example, doesn't mean you know all the sub-specialities in that field. Further, all of us have to guard against our human nature of being deeply wedded to past decisions and future justifications of them. Bias can come from where one studied and who one studied under. This is amplified when on diligence calls one feels the need to disprove the other. Technologies can be dismissed out of arrogance rather than understanding.

Yet you won't know that unless you have an incredibly humble physicist on staff. Same goes for an employee without the specific technical expertise evaluating which company to join.

Instead: Find an academic, national lab, military service lab, MITRE, RAND, or Aerospace Company technical expert in the same exact technology and ask for 30 minutes of their time. They'll often meet with you - you simply have to find them on LinkedIn or find their email and ask. But don't make the mistake of telling a government-employed expert that you want to talk to them specifically as part of your diligence of company X, Y, or Z - it triggers a fear of a conflict of interest and they'll pass on the call.

Say you are an investor interested in learning more about the tech and its applications because you want to increase your investments in the national security space and give them a preview of some basic questions you'd like to ask. If you know what questions to ask and how to ask them (I’ll write on that more later), they will outline for you all the ways the tech may not work and you'll walk away with a solid list of questions to ask the company. They'll also give you companies verbally that you should compare.

Also ask them to give you the names and contact information of two other experts who agree and disagree with the tech approach.

If the company you’re diligencing won’t give you a couple of these references out the gate, pass. It should go without saying that you should go beyond the referenced contacts. Then find & offer to pay an academic third party expert to join you on further technical diligence calls so you can watch the exchange and interject with your own questions. Don't invest in a deeptech company without getting a third party expert involved. It's cheaper than you think.

Subscribe now

2. Don’t fund a private version of a national lab. If you’re looking to join as an employee, know what you’re getting into. Are you joining a research environment or a company-building environment? They are very different.

Government funds basic research and industry funds products. Nobody funds the “in-between” except for those who are “venture” investors in the truest sense of the word. Perilous risk with phenomenal upside (as our Twitter feeds full of $NVDA news remind us) isn't for the faint of heart. The "in-between" is where the glory and returns are, yet the "in-between companies" aren't all equally as risky.

If a deck shows what is essentially a science project requiring 5-10 years (or more) of capital intensive investment before any revenue, with scientific breakthroughs scheduled on their “roadmap,” know you're wading into the deep end of risk even for deeptech. Gov’t grants or small gov’t R&D contracts they expect to win in the 5-10 year time period don’t count towards this idea of “revenue" though government "programs of record" do (more on this later). Be that as it may, R&D contracts are important as a start - if a company post seed claims to be “dual-use” but hasn’t achieved one of these yet or can’t speak to exactly how they're getting one soon, pass.

Instead: Find companies with revenue off-ramps along the way to their ultimate technology goal and market that amplifies the core tech rather than distracts away from it. Easier said than done, I know. But they exist and I’ll write more on hard questions to dig at on this in the future.

Ask and distinguish early between pure R&D money coming into the company and sales of devices/products/services to government customers if government is the pathway a company claims will lead them to commercial markets.

3. Scientific breakthroughs can’t be scheduled via slideware roadmaps. (I know, I know, "thanks Captain Obvious"). But it's a bit shocking how easy it is to overlook this and justify it because you like the founder or the concept. If the company needs a scientific breakthrough to make any money, unless you're really on the bleeding edge of deep tech investing and some of these bets are foundational to your strategy, see #2. This is hard because the initial pitch may lead you to believe “it’s just an engineering challenge at this point.” Most of all, watch out for any company that needs to overcome a material science challenge. (If a company has to create/discover a new material in order to provide value, that is what we call a material science challenge folks, not an engineering one!)

Instead: Look for companies that clearly distinguish between a science challenge and an engineering challenge and back the engineering heavy ones. It's not to say that you should never fund any science. After all, evergreen companies develop intense market leverage, but the science part shouldn't all be upfront in many national security tech cases (though biotech/pharma plays are outside this framework). This is the classic "exploration vs exploitation" model. The heavier the science, the more important #4 is below.

Share

4. There are "engineering challenges" and then there are engineering challenges. If a company doesn't point out exactly where they are on the science>engineering spectrum, acknowledge where the hardest challenges are, and demonstrate how they obsess over solving these challenges daily, pass.

Instead: Look for companies that say the hard part out loud without being asked. More to follow in future posts on questions to pose and follow-up you can do in deeper diligence to drive to the answers you need.

5. Don’t pass on an entire industry because it’s "too nascent.” This sounds counter to #3 and #4, but it's not. Beware of conflating one piece of industry for the entire industry as Lux Capital did recently in their shareholder letter with quantum and fusion.

Most people hear "quantum" and the mind immediately jumps to “quantum computing,” which is admittedly further down the road for real-world value despite the hyped headlines and alluring McKinsey reports. Yet, quantum computing itself is one of the highest optionality bet you could make in computing if a quantum company also has other revenue off-ramps that don’t district, but rather build towards, this ultimate end goal.

Said more precisely in the quantum case - there's a lot more to quantum than quantum computing. There are optical atomic clocks, for example, well past the scientific research phase with near-term industry applications like data throughput speed-ups for data centers in addition to government assured Position, Navigation, and Timing (PNT).

If AI is going to scale, we’re going to need to rely on Sam Altman and $7T for chip fabs, (and Chinese money apparently), or we're going to have to find new ways to increase data density as we also scale domestic and "friend-shored" production. In the quantum clock case, it’s a matter of integrating photonic integrated circuits (PICs) to make clocks smaller and cheaper through manufacturing cost curves to expand sequentially to reach massive markets. This is an example of a non-trivial engineering challenge and a supply chain challenge.

Instead: Make room for the cognitive dissonance of holding two opposing thoughts in your head at once. We rely on mental models and shortcuts. Categorizing for a quick "no" makes sense. But beware of throwing the baby out with the bathwater. A good way to avoid this is to start with industries you believe are "too nascent" and do some research to find the POCs for those associated portfolios at MITRE, RAND, any of the military service labs (AFRL, ARL, etc), and ask them what they think are aspects of the market not typically captured in the news headlines or understood by most. They'll tell you. If you want to find hidden markets, much like CIA sources, they don't always come to you (even if you're a big name) and they're not always obvious at first.

Final thoughts: For those of you just starting to catch the wave in deeptech national security opportunities, you're not too late. Welcome, but take caution in jumping onto a bandwagon you know little to nothing about. At least buckle up. The road to national security deeptech is fraught with challenges and few outside these specific industry niches understand them. You'll never fully know what to ask & how to evaluate a company technically, but there are ways to leverage others for this and mitigate risk for massive upside. Much depends on your risk appetite and the company stage. Financial return remains paramount. But a sense of mission matters, too, and if you don’t have that, then it’s probably better for you to work on something easier and less consequential like building another food delivery app.

Share

A) If you are applying to CIA because you hope you’ll be a sex object, please withdraw your application. B) If you’ve thought about applying to CIA but hesitate because you fear you’ll be a sex object, read further. C) If you’re still on the inside, fix the promotion system first, which will address a myriad of other problems, to include sexual harassment. Future officers are depending on you.

The depths of depravity surfaced last month in the form of this headline and story from The Daily Beast, “Ex-Spy Accused of Putting CIA Hopeful through Sordid Secret Sex Training.” For any young person considering a career with CIA: there is no CIA training that involves any form of sexual activity, to include: flirting, seduction, harassment, assault, or rape. This is something featured only in spy movies and a few other countries’ spy services, not CIA curriculum.

Given the extensive background checks and continual vetting, CIA should have a near-zero statistic of sexual assault from officers within CIA’s own ranks, current or former. But even with a rigorous hiring and vetting process, character isn’t always easily judged. Over time, some individuals are shaped by the aura of secrecy and become the worst version of themselves. As Congress and CIA take steps to stop these bad actors from within, CIA must do more to address a general lack of accountability that allows this behavior to take root. In addition, one sexual harassment-related challenge that is less discussed but just as prolific is how CIA prepares its officers for ambiguous situations they face while trying to recruit foreign sources abroad.

Espionage traditionally has been a man’s world and it’s exactly for that reason that women CIA field officers are so effective and a critical part of the CIA workforce. CIA sources predominantly are male because men still hold most positions of political, military, and economic power in adversarial countries, as well as in non-state groups such as terrorist organizations. (A “source” is an individual who provides information or “intelligence” on foreign countries or groups, also known as an “asset” or “spy.”)

Female CIA officers are force multipliers in such a dynamic because we’re highly perceptive of changing moods, motivations, and vulnerabilities of others. As the traditionally smaller and more vulnerable gender, girls grow up evaluating social situations and people they meet, especially men, for potential threats. Women arrive at CIA with those skills – a developed ability to read people and situations. Further, most female CIA officers are disarming. We can walk into almost any location and strike up a non-alerting conversation. Building empathy and trust comes easier to us and most male sources are responsive to those traits. Moreover, men are also often eager to impress women and will go to great lengths to do so, to include providing secrets.

Share

Pop culture often portrays the lifestyle of CIA field officers in a way that suggests they use sex to recruit sources. The truth is that a truly professional intelligence organization does not lower itself to using sex or coercion, especially as both only create more vulnerabilities, complications, and resentment for a would-be source. Further, romantic relationships can be fraught with complexity. And complexity creates a higher degree of risk that the source will act out in ways that ultimately lead to his (or sometimes, her) discovery. CIA’s sacred duty is to keep its sources undiscovered and, therefore, safe. Aside from this being the ethical thing to do, a service that protects its sources is a service that senior Kremlin officials volunteer to spy for and a service that has a deep and continual well of secret information.

Shared Human Desires

The heart often rules the head. The core job of a CIA case officer is to leverage the fundamental aspects of human nature and to seduce, but not in the way an outsider might think. CIA officers recruit a source with the source’s own hopes, whether it is to change the despotic nature of their government, to create better opportunities for their children, or to seek revenge for a lack of promotion or some other perceived sleight. Additionally, there is an element of adventure in an illicit, secret relationship that makes it doubly attractive.

For men from a culture where it is taboo to meet with a female alone outside of family members, it is a thrilling twist on traditional power dynamics to meet with a woman who speaks with the power of the U.S Government behind her, as well as with cool-headed self-confidence. This can create a potent paradox between stereotypes and reality, which brings added intrigue to make the relationship even more attractive or unique to a source, even when it has no physical element.

Sex as an Undercurrent

For some sources, physical desire may reside in the background of their minds. But this is the unspoken reality in many relationships, not just with CIA sources and their CIA handlers, because it is human nature.

Due to the undercurrent of gender and power dynamics, some of these relationships can be challenging, especially in the beginning. CIA does not teach its female officers who deploy overseas and meet a range of male targets in back alleys, remote parts of war zones, and in hotel rooms alone how to handle sexual advances from sources. I had to develop my own mechanisms for dealing with flirtatious and periodically more aggressive advances.

In most cases, I was able to deflect and establish boundaries while allowing the man to save face. In almost every case, we developed a genuine like and respect for each other. I looked forward to our meetings, and in any other circumstance, would have characterized some of these sources as good friends. Out of a multitude of encounters, I was fortunate that only once did I feel the sexual assault threat was so great that I sent a male case officer to future meetings in my stead.

Grappling with how to deal with unwelcome male advances isn’t new to most women reading this essay. Women begin to learn from an early age that they must find a way to deflect this behavior while also protecting men’s egos. We carry guilt when our efforts fail, and we have to decide on how and whether to handle increasingly forward encounters ourselves, entrust colleagues for support, or if particularly egregious, leave a job or opportunity we love because of behavior we hate.

CIA has relied on the inherent gut responses female officers have upon starting their careers at CIA and skills they individually develop over time, when it should be providing a better set of tools for all its field officers on how to de-escalate these situations. I viewed it as a personal responsibility to inform new, female trainees of what they might face and shared with them that many sources will make sexual advances. We can leverage that to our advantage, but we must be incredibly careful not to encourage the behavior, which would lead to increased advances, and potentially the threat of violence.

A natural inclination of women is to stay quiet and divert attention when such advances occur, and that’s what I often did. I would appear to ignore it with a redirection of the conversation elsewhere, while later raising a story about my “husband” or “child,” even when I didn’t have one. I would go into the great relationship I had with my “brother” or “father” and how this individual reminded me of him. Usually this was enough. It was the indirect signal the man needed. If more emphasis was required, I would find a reason to cite my position as “a U.S. Government official” and “direct representative of the U.S. Government who spoke with the authority of the U.S. Government” and refer to myself and the source as “professionals.” Every now and then, we’d have to repeat the conversation, but usually this held advances at bay.

Subscribe now

When Values Collide

In addition to navigating these situations, female officers have to be careful how they characterize them in official documentation containing the details of meetings to a larger CIA audience for posterity and review. I tried to document these encounters in ways that wouldn’t draw the concern of senior male colleagues. Otherwise, many would have responded by removing opportunities, thinking they were genuinely protecting me from a situation I couldn’t handle. This would limit career advancement unnecessarily.

Values eventually collide. Sometimes we must let certain things slide in order to achieve a greater good. But knowing what to let slide, what to never compromise on, and when to take a stand is inherently hard.

CIA generally must meet the world as it is, not as we wish it were. CIA field officers should not be social justice warriors in conducting recruitment operations, and CIA must acknowledge that it is appropriate at times to send one officer over another due to a myriad of characteristics, to include gender. This is difficult to stomach in a US-centric human resources mindset. CIA’s mission is not to change the social stances of its sources, but to collect information so policymakers can make better decisions and protect Americans.

Though my job wasn’t to try and reform the world’s maligned attitudes toward women and minorities, that occasionally was the result. After years of handling male sources, some told me stories about how they were more open-minded about future opportunities for their daughters based on our deep discussions about our lives and hopes for the future.

Too many in the US have lost a willingness to sit down and have hard conversations across the political and cultural spectrum. We jump to dismissing others for their views rather than taking the time to offer alternative ways of thinking and acting. We’ve become too quick to claim victim status. It's the sense that there no longer can be shades of gray; you must either validate my feelings or you’re wrong. Put simply, we’ve lost the art of engagement and persuasion, an art that CIA case officers almost exclusively rely on to recruit sources.

Yet, endless engagement isn’t always the answer either; sometimes we must seek peace through strength and that means not engaging until certain conditions are met. There also are deadly enemies out there who would kill at the first opportunity; dialogue is not and will never be an option with them.

When to Fight vs When to Yield

This challenge of knowing when to fight and when to yield, to include when standing up for and living by values when they collide, isn’t easy. Unfortunately, some CIA senior officers fail to see the nuance and bow to a foreign government liaison service’s worldviews unnecessarily, for example, by giving into demands that CIA only send male officers to meet with them. Giving into such demands only decreases CIA’s leverage in the long-run, whereas an appropriately timed and selected “stand” can serve to increase respect, leverage, and power. Such officers do not actually understand power dynamics and instead are looking for confirmation of their own beliefs that women can’t handle men as well as men can. They fail CIA’s mission and our American values at the same time.

The more legitimate questions arise on when it is appropriate to send a male vs female officer to meet an individual source. Recruiting or handling a vital source can lead to major career advancement. I tried to send the best-matched officer based on cultural competency, language capabilities, and/or the sensitivity of the source and the ability of the officer to plan thoroughly without making mistakes. In my experience, a female officer often has a small advantage in many situations due to all the reasons already discussed. But sometimes the situation demands that CIA send someone who can blend in better to the surroundings or better cater to the worldview of a specific target. Sometimes this simply meant sending a man, even if he had equal or perhaps less skills than a female colleague.

Share The Action Line

The Headquarters Situation

Because female officers already face a number of sexist challenges, they are fearful of any sort of formality around issues of gender in foreign operations. It risks the implication that women aren’t up for handling difficult cases, or that they need to be coddled in some way. Supportive male CIA officers equally don’t want to raise it for fear of being labeled sexist.

Further, risk aversion at CIA is growing, and the removal of all risk is fundamentally at odds with CIA’s mission. CIA field operations are already too reliant on decision by committee, too often deferring to Headquarters-based panels comprised of individuals who are far removed from events on the ground and lack true accountability. In a “decision by committee system,” if everyone decides, then nobody is to blame for a failure, yet everyone can share in a success.

Proximity to power matters. Those who sit at CIA Headquarters are in closer proximity to senior leadership and one of their roles is to brief successes in the field, which is powerful currency for career advancement. If not corrected, it is the nature of a bureaucracy to trend towards failure-avoiding behavior rather than success-seeking behavior. If left unchecked, a bureaucracy will begin to define success as the lack of failure or by marginal gains that don’t really matter. This leads to the cascading effect of risk aversion. For these reasons, creating a “Headquarters panel” or any sort of “Headquarters approval process” – a typical, reflexive bureaucratic response – would only diffuse accountability further, create more risk aversion, and not address the challenge. 

And yet, female officers need support.

What is To Be Done?

There is a relatively easy and tactical step CIA can take to help officers deal with sexual advances and violent situations they face when putting their lives on the line to gather critical foreign intelligence. CIA leadership should establish a series of discussions as part of field training courses led by female officers that talk through these various scenarios and potential means of de-escalation. The Directorate of Operations (DO) should also establish a group of referents to provide officers, male or female, suggestions for how to navigate these kinds of tenuous situations. These referents can serve as a pool of officers whose job it is to mentor and advise without affecting operational decision-making.

While it is inevitable that officers will deal with harassment in the field from foreign sources, they should not have to sustain abuse at home and from within. To deal with this, as well as with officers who think the solution to harassment by foreign sources is to simply send more men in place of women, is to establish more accountability through a reformed promotion system. Most importantly, CIA must stop promoting mediocrity. CIA leadership must recognize just how ineffective the current promotion system is and that sexual harassment in the ranks is one of the second-order effects of allowing mediocre to downright bad leaders and managers achieve positions of power.

Until this is addressed, fertile ground remains for sexual harassment, risk aversion, and its opposite - unbridled and ill-considered operations - to take hold. If CIA wishes to remain relevant as the world’s pre-eminent spy organization, it must move beyond tackling symptoms to addressing the underlying problem.

If it does not address this underlying promotion of mediocrity, newly-established offices and task forces will fail to stop the behavior. An office doesn’t stop bad behavior. Only good people willing to make hard decisions, and empowered to do so, can.

The people of any organization are what define it. CIA is no different. When empowered, capable officers recognize problems and what needs to be done to solve them without a bureaucratic panel or regulation to guide them. They can operate amid ambiguity and chaos. CIA must enable these capable officers if it wishes to maintain its relevance in an ever-changing world riddled with ethical, technological, and economic challenges.

If you’re an exceptional woman willing to take on these challenges, please apply. You have the opportunity to be the officer who recruits some of CIA’s most valuable future sources. Our national security may hinge upon your choices, your ethics, and your smarts. CIA needs you.

At least a few times a month, people looking to jump ask about my transition, which has led to me consolidating my comments below. Some of what I write will be controversial and all of it is biased. This is Part III of III.

• Part I addressed the basics of how & where there are differences between the Agency and the private sector, an assumption of what aspects of government you’ll miss based on my own nostalgia, as well as how to characterize old skills to new roles, job hunting advice, and resume missteps.

•  Part II addressed criteria for choosing your next role, the most common types of business roles that formers go into, and how to think about big vs small company risks and current markets.

•  Part III, below, is about title, compensation (base salary + equity + bonuses), and resources you can use.

=================================

1. How should I think about my first job function & title?

First role on the outside

You might hear advice like “your first job doesn’t have to be your forever job.” Yes, that’s true, but as the mantra goes, “it depends.” Take caution against taking any job as your first job as a way to get your foot in the door in industry. Your first title, role, and salary will be the basis from which future titles, roles, and salaries are set. Even if you’ve had all the accolades internally, you can’t prove any of it to anyone outside. Industry doesn’t know you, so your first outside title/function can serve as a pathway to faster credibility. You’re essentially hitting a reset button, so choose your starting point well.

Your experience likely includes roles of significant responsibility and authority, at times, life or death, which often enhances critical thinking skill sets, judgment, and EQ. So, don’t sell yourself short.

The underlying sentiment of “your first job doesn’t have to be your forever job” is accurate, however. Many of us are “loyal” to one job. You may only stay in your first jumping off point for a year or two, and that’s okay.

Titles:

Titles can vary greatly according to companies and sectors. For example, it’s useful to know that a VP title in the financial world is fairly ubiquitous and not necessarily an indicator of seniority. I’m not going to cover the technical role titles, which are also different, as this post is focused on those with my background and primarily geared toward startups.

For someone coming out at a GS 14/15 level, a “manager” title is likely as senior as you’ll get at a large, public technology company. If you’re more senior, and in a tech-related and public-facing role and you would like to work (not simply advise), you can shoot for a Director or Senior Director role at a public company. It’s possible you could get VP or higher at a public company, but that’s usually saved for former heads or deputy heads of agencies.

If you’re retiring and pulling a pension, your age, situation, and desire to climb yet another ladder may be quite different, of course. And you run into the fundamental question of how you want to spend your time at different stages of life. Some companies will be wary of hiring very senior government and military officials into daily/salaried company roles, because there are stories of senior officials taking a “pontificate and delegate” approach, rather than rolling up their sleeves. Or you may be hired into a more ambiguously-titled role like “VP of National Security,” which can be the equivalent of hiring you for your name, advice, and the introductions you can make, not managing people, actual programs, and revenue. (I suspect after years of doing just that, this would be a nice break.)

Like with the GS scale, many companies band salary to rank (pay bands), though there are some exceptions and variance according to industry vertical. Titles in tech start-ups generally go from Individual Contributor (IC; but often not titled as such), Lead, Manager, Director, Senior Director, Vice President, President, C-suite executive (CEO, CTO, etc), with a number of variations that are company dependent. An individual contributor could be quite senior and influential in a company, and you’ll often see this for those with deep technical expertise. We don’t want to shackle some people with the responsibility of managing others because their day-to-day contributions from a technical side are so important. The government does this as well, but I think less effectively.

Some companies opt for “Head of” roles and make many people in the company “Head of” something, so it can be difficult to determine the actual level of seniority and who reports to whom. LinkedIn is your friend in determining where a job might fall, and you should research a number of employees and executives within a company and look at their backgrounds to try and determine their structure. In the interview process, you should simply ask about the reporting structure and what career progression looks like at the company.

At smaller technology companies around 100-200 people, rough estimates are 5-10 years of experience is a Manager, 10-15 years of experience is a Director role, 15-20+ is a VP role, but keep in mind, unlike in the government, years of experience is not always a precursor to seniority and there are many senior technical folks in individual contributor roles. These ranges are for you leaving government service assuming you want a management track role. The smaller the startup, the higher the title you can pursue.

Subscribe now

Reporting structure:

You may report to someone younger than you or equal in age. You’ll be tempted to think that you know better on how to lead and manage by virtue of age and “real world” experience. Though you may well, be careful here. There are some brilliant young technology leaders who are good at leading people, creating (and staving off) process, and planning strategically for the future. Usually this is in direct proportion to how much personal accountability they’ve shouldered as they rose through the ranks and resulting resilience. You’ll be surprised at what you can learn from them, but you have to be open to this learning in the first place.

Just like some will dismiss you as a bureaucrat based on your government affiliation, don’t make the same mistake and dismiss an industry person because you’ve become accustomed to time in grade. Ability matters more than experience. At the same time, there usually is value in years of experience, but I mean actual experience where someone faced challenges and overcame them, not years of simply occupying a seat. Industry doesn’t tolerate someone simply occupying a seat in the same way government does, so you tend to find less of “those” people.

The attitude and competence of your direct boss is, obviously, critical. Make sure you’ve met them if they weren’t already involved in your hiring process (in a small company, they should be involved in the interview process; if not, it’s a red flag.) Ask them their own reporting chain up to the CEO.

“General Manager” or “Managing Director” often denotes added seniority & responsibilities, such as managing a P&L (profit & loss centers). Sometimes you will see a title like “VP and GM of X Division,” which means they probably have more of a prominent voice in the company.

Non-revenue generating business units are referred to as “cost centers.” The executives running those units aren’t accountable for bringing in money directly (ie, VP of Government Affairs). Obviously, these are critical roles too that indirectly drive value, but just like at the Agency, there is an implied hierarchy for those who bring in revenue or other forms of investment, rightfully or wrongfully, and it pays to know it.

Promotions:

You all have seen it happen. A mediocre to poor performing GS-15 is selected to run a program, and sent home short of tour after a long stint of chaos, when it would have been a better choice to select a GS-13 who, over the course of two tours, demonstrated the discernment and capability to take on a more consequential role. But, bureaucracy craves stability over growth, and it’s a safer bet to stick with the status quo. The powers that be won’t get in trouble for putting a GS-15 in a role who messes up, but they risk their own next assignment if they install a GS-13 who makes mistakes. In industry, however, growth and innovation are critical, which makes industry’s risk calculus different. You’ll see young CEOs of technology companies running organizations far larger than a government agency and doing it well. (There are, of course, others who clearly need “adult” supervision.)

Share The Action Line

The Good News:

Time in grade doesn’t apply! In industry, your value can be a bigger determinant of upward mobility. Generally, you’ll still be promoted rung by rung, but this can move at a more rapid pace in industry. But, just as in government, a “good old boys’ network” can exist and it pays to know how the network operates. Relationships matter. Your work won’t always speak for itself. Find champions and self-promote without being “that guy/girl.” More good news: unlike in government, there aren’t layers of paperwork and bureaucracy to cut through in order to hire, fire, or promote. This gives industry two added levers: incentives and the (real) threat of termination. Some companies cull the bottom 10% or more yearly.

Negotiating:

It is common to negotiate title. The smaller the company, the more flexibility you’ll have in crafting your own title, because they’ll have less process in place, fewer employees whose expectations they must manage, and the more they’ll hope that someone like you can come in and supercharge their efforts. As they grow, companies will want to avoid title and salary inflation by becoming more standardized.

Remember:

While I don’t recall where I read this quote, I think it’s appropriate here and it’s also a word of caution on title obsession, “There is a difference in being given a title and mastering the art of command. One can happen overnight, the other may take a lifetime.”

2. How does salary work on the outside?

It’s possible to make 2-3x your government salary on the outside over the course of a few years. Moreover, you could become truly wealthy in financial terms if you join a startup that goes public (via an Initial Public Offering or “IPO”).  However, an IPO with a startup is rare. The decks are stacked against you and so are the markets. But, it’s at least it’s an option on the outside.

If you’re like me, you may have had large portions of your Agency career when you didn’t even know what your salary was until you filed your taxes, only to be forgotten again until the next year. While you track what’s deposited into your bank account every other week, and know how you need to regulate your spending based on it, the total salary amount isn’t a status symbol for you. (Status wars are reserved for assignments!)

 But on the outside, your ego will not only be susceptible to roles/titles as a status symbol, but also salary and bonuses. While taking caution not to fall into the trap of conflating your self-worth with net-worth, you still should advocate to be compensated according to what you actually bring to the table, which is quite a lot. Industry refers to how you’re compensated with the term “total compensation.” Salary, alone, isn’t the end all be all. The basic equation is:

Total Compensation = Base Salary + Equity + Bonuses

First, none of what I write here should be taken as financial advice. Startup pay-structures usually offer less base salary and more equity (stock options) plus some bonuses. Startups that have raised a Series A round with reputable investors usually can match the salary you’re making in government. You should negotiate up their offer. Be the first to throw out a salary number because that is the anchor number they’ll work from. The challenge is to not come in so high that you seem naive vs selling yourself short.

Market research will help you get a sense of what is appropriate. It’s like in training when learning how to ask uncomfortable questions “going through yellow lights” until you hit a “red light.” Talk to people on the outside that likely are your equivalent and simply ask. Ask them what their sense of a salary is for someone with your background going into “X company” (choose a company similar to, but not the same as their own). They’ll likely answer based on their own compensation and it will give you a good data point.

The more mature a startup, the more likely they can increase your government salary from the start by about 20% (include an approximate amount for overseas housing added into your government salary). Don’t forget that you can move up in salary much more quickly than in the government, and they often have bonus schemes depending on the seniority level. The chains of the GS system do not apply! The more you bring value, the more you can earn.

Sales roles usually have lower salaries but higher bonus schemes to incentivize selling. Bonuses can be pegged to hitting certain metrics for non-sales jobs, too.

Ask for a hiring bonus pegged to about 15% of your base salary. You can offer that you’re turning down an alternative overseas position worth quite a bit in mortgage/rent payments. If the job is remote, ask for an initial office stipend of $5,000 to purchase a desk, monitor, printer, basic office supplies, etc.

Equity:

Equity aka “stock options” aka “options” is essentially offering you an ownership portion of the company. Ask how many “total shares outstanding” the company has. (Divide that by the number of options you’re offered and that’s your ownership percentage). The earlier the stage of the company, the larger percentage you should be offered because you’re shouldering more risk and you have more ability to make (or break) the company.

Ask if their option amounts are pegged to different title/pay bands and generally what those options bands are. Ask for the current 409A valuation of the stock price. A 409A is a third-party assessment that places a financial value on the stock done as part of financing rounds that is pegged to the low end of value (reasons here begin to get complicated so I won’t get into the details in this post). Ask about the strike price. The strike price is how much you’ll pay to exercise (“buy”) your options in many typical compensation packages. In some cases, a company won’t share this information with you out of sensitivity concerns, and you should offer to sign an NDA to get this information if you’re serious about joining them and they’ve given you an offer.

For me at first, options were utterly confusing and I spent a lot of time Googling. On top of it, there are different types of options and various tax implications. While Google is your friend, I suggest hiring an accountant and lawyer to translate the legalese in a lengthy employee stock incentive plan. I eventually did so and found the peace of mind worth it.

Here is a quick, typical example not laden with additional HR/legal language that gives a basic overview:

Congratulations, Frank! We’re pleased to offer you $200,000 in annual salary, a $25,000 hiring bonus to be paid out after six months of employment, $25,000 yearly bonus potential, and 100,000 options at a $.05 cent strike price, which have a four-year vesting schedule with a one-year cliff. -Julie from HR

Let’s walk through the equity portion. The numbers given here are meant to be easy from a calculation standpoint.

25,000 options (1/4^th representing one year) out of your total 100,000 will “vest” or “become purchasable by you” at a price of 5 cents per option (“share”) after one year of employment. This is the one year “cliff” which means that if you leave before a year, you get zero. You can choose to “exercise” your options (ie, purchase them) at a $1250 cost to you after one year (25,000 x .05), or you can let them accumulate in their own virtual bucket. Many startups use the website/service Carta as a way to track your options. Many people wait to purchase options as they see how the company performs, but there can be tax complications as you go. Again, it’s worth talking to an accountant.

The remaining 75,000 options will vest in equal monthly increments after the one-year mark for the next three years. So, 75,000 divided by 36 = 2,083 options vest monthly for the next three years.

The startup may choose to grant additional options at any time as an equity “bonus” or at certain milestones such as a promotion. Let’s say that you’ve been with the company for a year and helped them target new customer sets that led to massive revenue, which allowed the company to build more products and begin to scale. So, you’re promoted, and you get another 50,000 options awarded to you.

At the same time, however, the company still needs to bring in more outside investment (such as venture capitalist money) to truly scale the company because the sales revenue alone isn’t enough to expand quickly and hit all the target sets they know they could hit if they simply had the money to expand and do so.

As a result, the investors get even more excited about the prospects of the company and they put more investment into it. As they put more money in, the investors agree on a new, increased valuation (total value) for the company (ie the company was worth $20 million dollars before, but now they think it’s worth more). So now, the strike price for future options issued has increased from 5 cents per share to 15 cents per share. Let’s say that your promotion occurred right after the valuation of the company changed, so any new shares you’re awarded will now be at a 15 cent strike price. So while the 5 cents per share price continues for all the old shares you were granted (even if you haven’t exercised them), for the new batch of shares, you’ll have to pay more to buy them at the 15 cent price. Ultimately, you want the company to go public at a very high per share price and you make money on the difference. This is the financial value of getting in a startup “early” among other things.

When you end your employment with the company, you’ll have around 90 days or some set time frame where you must decide whether or not to exercise (purchase) all options that have vested up to that point. If you don’t purchase them, they’ll go back into the pool of options to be given out to employees.

The Bottom Line on Equity:

Equity is always a gamble. It’s very possible that you’ll pay for your shares in your company and they will not amount to anything and you’ll be out of pocket never to recoup any of that value.

But, if you choose the right company with the right product/service and at the right time, and you do everything in your power to make it successful and it IPOs, you could walk away with a substantial amount of money and experience.

Remember:

If you’re a case officer, by virtue of the correlation of wealth to power to access, you’ve probably recruited some of the wealthiest people in the world who were also some of the most miserable. Beware of jumping from one hamster wheel of achievement to another. As Nassim Nicholas Taleb wrote, “The three most addicting things are heroin, carbohydrates, and a monthly salary.”

3. What are some other practical tips for talking with prospective employers?

Storytelling:

Tell a story about the future, not the past. Don’t say why you’re leaving the Agency but, rather, why you’re interested in a particular industry vertical, role, and company. Be able to tell at least one good story from your past that encapsulates your personality and your goals and your work ethic. Don’t forget humility. Sometimes we C/Os forget. I recently did a mock interview for a former USG employee looking to transition and he told an amazing story about why he joined the military, why he then joined the USG, how he deployed to Africa, what his day-to-day was like on the ground, and how and why he founded a company while there. He linked it back to his values and his character, and his story felt like a front row seat to his journey. It was a great example of storytelling.

Good storytelling lets someone in on a small aspect of your life. Make the story count and link it to what you’ve already done, and make the person you’re talking to feel like they can help you achieve what you’re setting out to do next. It’s human nature to want to feel useful. Helping someone else feel useful is a way to give away some of your own power to others. People like those who share power. As you craft your story, I recommend reading about the hero’s journey as a storytelling arc.

Networking - LinkedIn:

LinkedIn should be your best friend. Everyone will have a different situation, but the more you can put in your profile, the better. A few tips:

• Try to translate what you’ve done into business terms. And to do that, you need to do a lot of research on LinkedIn about how other formers characterize themselves. Simply ask some formers for their suggestions.

• A professional headshot is worth the couple hundred bucks; reach out to me for a photographer recommendation.

• If you’re outside of middle age, don’t put the year you graduated from university in your LinkedIn profile. Ageism in both directions is sadly alive and well.

• Get a bio cleared that you can put in the bio section (more on that below).

• Have the headline section filled out with something appropriate for the industry/type of company you’re interested in.

• Don’t put the open to work banner across your profile picture. With human nature being the way it is, you risk coming across as desperate, when really you’re the catch.

• Take a look at my own profile to the degree that it’s helpful.

• Like and reshare posts relevant to the industry or type of job you’re seeking. Potential employers absolutely look at what you like and post.

• In the interests section, choose individuals, companies, and groups to follow which will show up in your profile. Basically, try to fill it with something to account for the gaping holes in your bio.

• If you’re trying to get in touch with a senior person in a company, find their EA or Chief of Staff and start there.

Networking - Introductions:

Try to leverage your existing network for “warm introductions.” This is the surest way to get a meeting. Assuming the person who introduces you is liked and respected, that’s really all you need as far as initial validation. A former IC Agency head introduced me to the then-CEO of my company because they had previously served together on a separate Board, and that’s almost certainly the single largest reason why I was hired.

If you must, send a cold email or message people on LinkedIn. It’s normal to do this via LinkedIn, though not everyone responds. I spent a lot of time thinking about the content of a first message to people. I probably had around a 50% response rate. See if there is another way to reach them outside of LinkedIn if you don’t get a response. I receive a lot of inbound on LinkedIn these days, to include a lot of spam/recruiter messages, and it filters into a different message area. If I don’t know someone or they don’t state who we know in common, I rarely respond. If you have someone in common, make sure to mention that.

Don’t go for a generic title of a message. Anecdotally, I found that referencing something they’ve written or something their company did had the highest likelihood of a response, followed by name dropping a common contact. The problem with the common contact, however, is they’re going to question why you didn’t just go with a warm introduction.

You can usually guess someone’s email address at their company, especially if you can find the addressing scheme by a few google searches online (ie, firstnamelastname@xcompany.com). You can pay for an online service like RocketReach to get their email addresses. Be careful with this. Don’t try and trick them into clicking on your email by titling it something like “Re: Meeting tomorrow.” Most everyone in industry gets tens to hundreds of spam emails a day just like that. Also, don’t be creepy and send a cold email to a personal email address.

Getting a resume cleared can take a significant amount of time, especially if you’ve served in a lot of positions outside your home base because it’s double the coord chain. It takes even longer if you have other paperwork you have to go through first. One tip is to get a short bio cleared while the resume is in process. The less you put in it about specific assignments, and the more general you keep it, the faster you’ll get a response. Mine was very generic. It covered how long I had been employed, that I was a C/O and had been a CMO, that I had served abroad, had served in various leadership positions, and my general leadership/management skillset.

This was important because I copied/pasted the language from it in almost every message/email I sent and put it in my LinkedIn bio (yes, it felt very weird at first openly emailing people that I worked at CIA). For what it’s worth, I find the PRB to be exceptionally fast on the outside, but this is much different than the paperwork to process out of the organization, which takes significant time.

4. What are some good resources as I look to leave?

• Contact me for more info on an alumni group.

• BreakLine – a couple people I know have done this and speak highly of it.

• Mission-focused tech companies I’d scout as potential jumping off points who will have an easier time understanding your value. I have a much longer document on this; if you’re interested, reach out. Feel free to add your own suggestions in the comments section.

• Infleqtion (obviously we get it!)

• Anduril

• Second Front Systems

• Strider

• HawkEye 360

• Flashpoint

• Primer

• Epirus

• Enveil

• Adarga

• Varda

• Palantir

• SpaceX/Starlink

  *This list is by no means exhaustive nor have I done significant diligence on any of these companies except my own.

• Learn about basic private vs public companies. If you’re going the startup route, you should educate yourself on the basic fundraising process: pre-seed, seed, Series A, Series B, etc. It will give you good context for the maturity of the company and what the company will be facing. Educate yourself on what an “exit” for a startup means: IPO or being acquired. I plan to do a post on this eventually if there is interest.

• During most of my time at the Agency, I read many business books because they contained excellent lessons I could apply to my CIA work. As I was leaving, they also helped me translate (somewhat) what I had done to business lingo. The most useful books were:

• Only the Paranoid Survive by Andy Grove

• Venture Deals by Brad Feld

• The Four Steps of the Epiphany by Steve Blank (all his books are good, and he also teaches and makes available content from a course on dual use national security technology on his website linked above, though one can debate how this approach is applied to new technologies and markets)

• High Output Management by Andy Grove

• On Grand Strategy by John Lewis Gaddis

• Zero to One by Peter Thiel

• Any book by Jim Collins

• Masters of Scale by Reid Hoffman

• The Platform Delusion by Jonathan Knee

• Lead and Disrupt by Charles O’Reilly

• Seeking Wisdom: From Darwin to Munger by Peter Bevelin

• Zone to Win by Geoffrey Moore. *If you’re an Agency senior reading this post and you plan to stay and want to change things still, please read Zone to Win. It’s about how to reform an entrenched institution and make it competitive again.

  *Keep in mind that in autobiographical accounts, people easily misremember their pasts and what led to their failures and successes. We tend to attribute our successes to keen intellect and our failures to random events not under our control. Or we virtue signal humility by acknowledging certain failures but not others. Most of us want to be the hero of our own story, so that lens is useful when evaluating recollections or the contents of any advice.

• Specific industry case study books that are engrossing reads that can be leveraged anywhere and give you a sense of how industry battles were fought, won, and lost:

• Hard Landing

• Flash Boys

• Bad Blood

• Blitzscaling

• Box: How the Shipping Container Made the World Smaller

• Barbarians at the Gate

Others books to read: Mission Transition (written especially for the IC), Organizational Physics, Designed to Scale, Your Next Five Moves, How to Decide, Reboot by Jerry Colonna, Working Backwards about Amazon, Mistakes Were Made (but not by me), Be 2.0, The 15 Commitments of Conscious Leadership, Crossing the Chasm, The Founder’s Dilemma, The Lean Startup, The E Myth Revisited, The Score Takes Care of Itself, Thinking in Bets, Good Strategy Bad Strategy, The Innovator’s Dilemma, The Courage to Be Disliked, Exactly What to Say, The 48 Laws of Power, Start with Why, Players First by Coach Calipari, High Growth Handbook, CEO Excellence, Boyd: The Fighter Pilot Who Changed the Art of War, and all of the Incerto series by Nassim Nicholas Taleb

=================================

At least a few times a month, people looking to jump ask about my transition, which has led to me consolidating my comments below. To be up front, some of what I write will be controversial and all of it is biased. This is Part II of III.

• Part I addressed the basics of how & where there are differences between the Agency and the private sector, an assumption of what aspects of government you’ll miss based on my own nostalgia, as well as how to characterize old skills to new roles, job hunting advice, and resume missteps.

•  Part II, below, addresses criteria for choosing your next role, the most common types of business roles that formers go into, and how to think about big vs small company risks and current markets.

•  Part III will be about title and compensation (salary + equity + bonuses) and resources you can use.

=================================

 PART II

1. I’m planning to leave within the next year, what should I be thinking about?

What’s your why?: First, understand your why. If you’re resigning mid-career, why is that? Not the superficial answer, but the real answer. As the quote by author and physicist Richard Feynman goes, “The first principle is that you must not fool yourself, and you are the easiest person to fool.” There is an aura you get working in the intelligence community, partially because of the mission and partially because of exclusivity. You may not have your college roommate’s finance job pulling in a high salary with bonuses, but you have something far harder to obtain, an affiliation with a cadre that’s so elite, it’s secret. We all seek belonging with an in-group and you’ll be leaving yours. For me, it felt like leaving a major part of my identity behind. This can be jarring and you really need to dig to identify what you’re walking away from and what you want to be walking toward. Knowing your why will help you make peace with the identity shift that is going to happen. I also suggest finding something you can strive for on the outside that is adjacent to the sentiment that pulled you into public service.

My own why: The future of national security is in technology, and I wanted to learn about emerging tech and capital markets so I could go back into government at the intersection of national security & technology policy better equipped and networked. The only way we’re going to secure our future is for the government and private sector to leverage each other’s strengths and mitigate each other’s weaknesses. Our government has a dangerous speed to market problem that bureaucrats alone cannot fix, even the best of them who usually start well-intentioned but become risk averse and ossified over time, not wanting to jeopardize their standing and sadly becoming what they set out to change. Tradition needs to be challenged from the inside, and one of the few ways to address this, aside from greater accountability, is to create an ethical revolving door between government and industry to serve as a refresh button against stagnation and risk aversion, with strong incentives led by the government. But that’s a post for another day.

How much time do you have? You’ll need to network with as many people as possible and ask them about their careers, ambitions, let downs, and get a sense of what they do all day and how they find meaning from it. Conservatively, I met around 40-60 individuals across various companies for one-on-ones before I left. There was a huge overhead to this and your timeline for leaving will dictate how much groundwork you can do. In all cases, it will be a balance of the time cost of gathering more information vs the benefits of making the leap more quickly. It took me about eight months. Reaching out to formers who can help with introductions and suggestions will help you exponentially.

For each of the industry verticals, I spent weeks to months researching the technology, reading forecasts for various companies and many related books, then hours that could be measured in days scrolling LinkedIn and Google sleuthing to find the best POCs to contact. For first contact emails or messages on LinkedIn, I spent at least 15 minutes tailoring each one for the best response or impression, then at least 30 minutes to an hour researching the person in advance of a call/meeting, 30 minutes to an hour with them, and then at least 15 minutes writing a thank you or follow-up email. Some meetings were in-person so add in transit time. When you work in the building you might as well be marooned on a desert island; you either have to take time off work or find someone who’s willing to talk with you early morning or evenings, as well as do all the research work early mornings, nights, and weekends. It’s daunting but you can do it. Much like good target selection is the key to good recruiting, zero in on the contacts most likely to talk with you based on their online engagement (do they post and correspond a lot with others on LinkedIn or Twitter?), or someone who is already a friend of a friend.

Where you’re (likely) limited: Your government-only experience has hindered your world view. Yes, you, world traveler who has seen and done things most people cannot imagine. You likely don’t have a good understanding of budgets, finance, and capital markets. Yes, you may have managed budgets before, even large ones, but budgets aren’t that hard when it’s taxpayer money. If you don’t meet your revenue numbers in industry, you either have to raise more money or you have to make cuts elsewhere. The first rule of startups is not to run out of cash. Many do and it’s lights out for the entire company and layoffs for people with families. Not exactly imprisonment or death, but still very consequential to people you care about.

There is a lot to learn on the outside. Some of the biggest failures are those who come out of a government-only career, especially at senior levels, with a sense of entitlement. Yes, you navigated bureaucracy well and probably pulled off some major coups in your time (not in that sense), but your war stories will only be good the first two times and perhaps over beers. What got you here won’t necessarily get you there. Take heed not to let your confidence dwarf your knowledge, because you can mistake self-belief with self-delusion. Adjust accordingly by combining a beginner’s mind with your ability to navigate stakeholders & equities and you’ll do well.

Big or small?: Decide if you want to join a big or small company. Choose big for stability and higher salaries. Choose small for learning, growth, and impact. In large companies, they usually want to put you in a narrow and specific role. Though you will have more roles you could move into if the first one isn’t a great fit. At small companies, you wear many hats all at once. I wanted to understand the daily challenges a company faced at the senior levels in trying to push a new technology in government markets, commercial markets, and how capital flows impacted all of this. In order to get these levels of insights and learning, I needed access to the source of where those decisions were made, which meant I had to go small. However, a bigger company is more defined in terms of a 9-to-5. I work just as much now as I did in the field. And though I work from an office most days, I also work from home, which affords a lot of flexibility because I’m not chained to a SCIF.

If you join a big company, assuming it’s public, you’ll get stock which immediately can translate into financial gains assuming the company performs well. The salaries are almost always higher. You can get rich in a big company (at least by our humble government standards), but rarely wealthy based on returns from that company alone. You can get wealthy with the right startup, but many startups fail, so it’s a long-shot. Of course, “wealth” is subjective. More than money, most of us crave impact. Both are possible on the outside.

What would you like to do? Some roles for former C/Os:

•   Business Development or “BD” roles: When you describe what a C/O does, most larger companies will see that as a sales or business development function. You’re out shaping the perception of your company in the market (networking), determining leads, and making contact with leads. The larger the company, the more they’ll separate out BD and sales, with BD focused primarily on lead generation and sales focused on sealing the actual sale of the product or service.

•   Sales roles: The sales cycle is similar to the recruitment cycle. At a small company, you have the ability to do the whole cycle, which pulls in strategy, BD, sales, and customer success: figure out what you should sell, who you should sell it to, how to get in touch with them, actually get in touch with them, sell it, keep selling to them and make sure they’re happy (customer success), and at some point, decide whether to move on to better sales targets, or convince your company they need to be selling something different. At a large company, sales usually means someone else has done the broad shaping for a potential customer, you just have to go in and work through the mechanics of selling them on your product or service.

•   Customer Success roles: This is handling. You make sure the customer is happy and keeps buying, preferably more.

•   Security roles: Some people from the Agency gravitate to security roles, and I’m sure some are quite relevant. An issue I found is that while I may know a lot about tradecraft-related security and how to hopefully stay alive for the first couple minutes of an ambush, I know very little about things like building security and computer systems security. Some companies will see a CIA background and confuse it with roles that are more akin to FBI or law enforcement. You can probably learn it and integrate well into those teams, especially if you worked in an actual cybersecurity or security role. I was turned off after someone told me, “If you’re the Chief Security Officer, you’re the last person the CEO wants to hear from.” I imagine that’s controversial and I welcome feedback from those in the security realm.

•   Trust & Safety roles and Threat Intelligence roles: These seem especially appropriate for targeters and analysts. I know a lot of formers who have joined companies in this capacity and seem to be doing well. This includes business intelligence. The role broadly is to protect a company and its people/users, or provide a service to other companies doing so by tracking bad actors & threats. Sometimes these roll up under a security division, though for many companies, this is the entire company.

•   Government Affairs/Legislative Affairs roles: These are lobbyists who engage with policymakers on a company’s behalf. The larger the company, the more they’re paying to have people represent them on Capitol Hill and advocate for their interests. For those with significant experience engaging with and briefing the Hill, this is a possibility, but that probably means you’re more senior, and you’ll be competing against staffers rotating off committees who are actually much better equipped than you as far as networking and know-how. Many start-ups can’t afford a full-time government affairs person, or a very senior hire, so they pay a lobbying firm at first. You may be able to step in once they want to transition into a salaried role for this, but keep in mind that they’re looking for the Hill contacts that you already have, as well as your ability to work the legislative process, not just your briefing or networking skills. Saying you’ve briefed CODELs likely won’t cut it. You may be able to join a larger company’s government affairs team at a more junior to mid-level, and you’ll probably find your skills most relevant to a company that works on national security-related issues.

•   Strategy & Operations roles: These roles help make sure vision, resources (budgets), and the market opportunity are aligned. They help figure out what to do to make things go right, and what to do when things go wrong, and usually work closely with the CEO or CFO. The smaller the company, the bigger your chance at a role like this. Larger companies primarily only look for someone who has an MBA, experience with one of the big consulting firms, or experience doing the job already, which creates the chicken and egg challenge. There are some business operations roles, which can be a more entry level. Ultimately, one could work their way up to potentially a COO or even CEO role, but this will vary widely at different companies and industry verticals. A Chief of Staff role, for example, is largely a strategy role, but is heavily dependent on what the CEO/company needs and wants. I’m the person who tells our CEO what he needs to hear, not necessarily what he wants to hear, and serve as an executive advisor from product strategy to setting business milestones to working with investors. I also work closely with all members of the executive team, the Board of Directors, and Advisory Board. I think it’s ideal for a former C/O, but I’m obviously biased.

•   Entrepreneur: A successful CIA officer must be able to operate amid ambiguity and make judgment calls that require strong second and third order thinking. Achievement focused and good storytellers, they know how to figure things out, “read the room,” and assess & mitigate risk. Most people believe C/Os and entrepreneurs are big risk takers, when, in fact, they’re more risk mitigators. If you find an A-player CIA officer jumping into a founder role at a mid-way point in their career, stay close to them, they’ll probably go on to do great things. They’re the equivalent of someone who drops out of Harvard business school to found a company. They have enough confidence in themselves to leave without the safety net of a future pension as well as the energy, ambition, and know-how to navigate uncertainty. The same EQ and approach that attracts investors will also attract excellent employees.

•   Venture Capitalist: An early-stage VC is almost the exact same job as a C/O. Spot, assess, develop, recruit, and handle founders building a company amid an uncertain operating environment that will bring a heavy return on investment (ROI). Just as CIA is the highest-status intelligence organization in the world, the more prominent you are as a VC, the more inbound you get (volunteers), yet outbound (targeting, developing) still matters. Both involve some levels of luck and timing misattributed to skill. The biggest difference is in the VC world, nobody is going to die. Much like many C/Os, VCs guard their cadre as an exclusive club.

•   Retirees: Leaving with your full pension means you’re likely going to fall into working in four general areas if you choose to keep working. This all depends on your seniority and the level of outward facing roles you had. It’s no surprise that some officers work hard to get public-facing roles that relate to technology or other posts that benefit their post-Agency job search. CIA needs reform here, and not in the way most people think.

1) consultant

2) sit on a company Advisory Board or Board of Directors

3) serve as an executive at a small company (you’ll be expected to actually work, not pontificate & delegate) or mid-to senior level at a larger company (you might just be a face)

4) get hired by Wall Street/Private Equity/VC firms assuming you’re senior enough and have enough New York or Silicon Valley connections

For 2-4, you’re generally being hired for your name and the introductions you can make assuming you’re within the top 15 of leadership.

Boards: People sometimes ask the difference between an Advisory Board vs Board of Directors. An Advisory Board, you guessed it, provides advice. Depending on the agreement, the company formally meets with its Advisory Board anywhere from once a quarter to once a year. Advisory Board members individually field weekly to monthly emails and calls from the company executive team to provide feedback on strategy & positioning and make introductions. Advisory Board members are often paid in a balance of equity (stock options) and cash (“cash” is the industry term for money wired to your bank account). A Board of Directors (BoD) is more formal and provides governance and financial oversight to the company. They can vote to hire and fire the CEO. CEOs seek their consultation (and often must seek their formal approval) for major strategic decisions such as acquisitions, major budget changes, hiring of C-level executives, etc. Formal BoD positions are harder to come by. If you’re an A-player from the senior-most ranks, I urge you to consider joining a private company board if you’re aligned with their mission and team. They need you.

For me, personally: People at startup companies in the senior ranks usually call themselves operators. Obviously, that’s a different definition of the term. I knew I wanted to stay/go into an operator role because that’s where the business learning I sought would happen. I didn’t want to turn around and have to sell back into the IC, because I didn’t want to leverage my contacts so tactically, but plenty of people do it (and we need good people to do it, we all know how badly the government needs commercial technology solutions). From the start, my job was closest to a BD role. Because it was a small company and I was going from top-down with the CEO rather than responding to a job advertisement, I was able to craft my function and initial title as, “Senior Director of National Security Solutions.” I began writing unsolicited strategy docs for the CEO, which ultimately led me into a strategy role, which led me into a strategy & fundraising role. I also took an advisory role with another startup working on national security technology, QuSecure.

2. How should I think about risk and how can I mitigate it if joining a startup?

If you decide to join a startup, know your appetite for risk. If you’re really bold, join an early-stage company (seed stage, Series A), but have conviction around the team. You may need to cover some portion of your own salary for a year. If you need to make a salary equivalent to what you make in government, target startups that have closed a Series B round within the last few months. If you’ve received a formal offer from a startup, you should offer to sign an NDA and ask how much runway they have. If they won’t sign an NDA and discuss any aspects of runway or value of the equity package they’re offering, look elsewhere. If there is enough interest, I can do a separate post that discusses funding rounds (pre-seed, seed, Series A, B, C, etc) and runway and why this matters, as well as what is considered “an exit” for a startup.

Look before you leap. Talk with multiple employees at the company. Try to talk with an investor in the company. Research their Board of Directors and Advisory Board members and contact some of them. Look for people on LinkedIn who used to work at the company and reach out to them and ask why they left.

A year of employment is enough to “prove” that you can hack it in industry, even if the startup fails. Being part of a “failed” startup is not the badge of dishonor you might think. Many startups fail, especially those in the early stages, and it’s more about the quality of the startup and what you did and learned. So long as you and the company weren’t pulling an Elizabeth Holmes or otherwise operating unethically and illegally, it’s not necessarily a red flag on your resume. This sort of experience matters far more to a prospective tech startup employer than the decade+ that you put in at the Agency.

After the six month to a year mark, if you’re in a sufficiently senior or in a unique role (or have a technical degree), you may begin fielding inbound soft recruitment attempts from other startups. This will increase with added time, responsibility, and the prominence of your company.

3. Should I be worried about the current job market right now? I hear it’s bad.

Yes, it’s bad, especially for tech. You’ll no doubt have heard about layoffs throughout industry. We are in a time of high inflation, which has led to high interest rates. This essentially means that it “costs more” to borrow money now. In the last decade, money was essentially “free.” Startups could borrow and spend (and pay salaries) with no need to turn a profit because they could chase growth over profits, yet still go public and cash out some of their stock and become wealthy. Investors funded these companies so long as they had strong narrative leverage. This is no longer the case. A common way to extend runway or increase shareholder returns is to cut entire programs to cut expenditures and conduct layoffs that cut labor costs, which is what we’re seeing.

Do firm due diligence on where you land. You don’t want to jump and then because you’re the new person, be first in line in the next wave of near-term layoffs, or find out that the company only has a few months of runway and they can’t raise their next round. Economic recovery may not happen until late 2024 or later, so always have a plan B and C brewing.

Subscribe now

At least a few times a month, people looking to jump ask about my transition, which has led to me consolidating my comments below. To be up front, some of what I write will be controversial and all of it is biased. Due to length, I’ve broken it up into a three-part series that will be published over the next few weeks.

•  Part I addresses the basics of how & where there are differences between the Agency and the private sector, an assumption of what aspects of government you’ll miss based on my own nostalgia, as well as how to characterize old skills to new roles, job hunting advice, and resume missteps.

•  Part II will address criteria for choosing your next role, the most common types of business roles that formers go into, and how to think about big vs small company risks and current markets.

•  Part III will be about title and compensation (salary + equity + bonuses) and resources you can use.

=================================

PART I

1. It must be a really big jump to the private sector, huh?

To begin, many people on the outside use the term “industry” not “the private sector.” It wasn’t a big jump. At the Agency, 85% of my time was spent navigating bureaucracy & equities, arguing for resources & permission for operations, and dealing with the bottom rung of employees, all while making decisions with little data or data overload. Only 15% of my time was doing the more exciting operations. Though that 15% - along with the camaraderie of some of my colleagues - made the work deeply meaningful.

Industry is similar. Human nature is human nature, and I deal with many of the same challenges and pull many of the same levers of satisfaction. The difference is my decisions now aren’t life or death.

Another large difference is the greater level of autonomy I have nowadays. Making decisions on the fly in operations is an extreme example of autonomy, of course, but there is always a back-end overhead. Depending on company culture, decision-making can be driven dramatically down with less overhead. As an example, I can make direct recommendations to Congress with no oversight, no internal reporting requirements, and with the trust of the CEO and Board.

2. Do you miss it?

Yes. Nothing beats the rush of bumping a target who agrees to meet with you again or landing in a foreign country for the first time. I no longer know the stories behind the headlines, and I’m not the person making those stories happen. Aside from close friends, I am now treated as an “outsider” by former colleagues.

Fortunately, I still work with smart people solving hard problems every day. And there is still meaning in what I do. Raising tens of millions of dollars from investors to advance a technology faster than the Chinese CCP is fulfilling and uses the same skillset. Learning how M&A deals are structured gives me the same thrill as first learning the mechanics of a surveillance detection route. It’s the excitement of being a beginner again, but one with deep and profound experiences, which blunts the downs and enhances the ups that you will face post-Agency.

I get to move our national security mission in emerging technologies farther and faster in ways that I could not in government. And while there is some level of self-justification in these statements, there is nonlinearity in industry. You can move at exponential speed. At the Agency, I felt like I would have had to wait another 10 years for positions of significant responsibility & authority despite proving early value, only to face even greater levels of risk aversion as I moved upwards. 

3. How do you transfer your old skills to your current role?

Driving decisions, organizational change, and operations in a deep tech company presents many of the same challenges and opportunities as my time in government. Leading and managing people amid uncertainty, high degrees of change, and making decisions remain my day-to-day functions. My role as a Chief of Staff is in many ways like a DCOS or traditional Chief of Staff in government. I work behind the scenes, and sometimes out front, to shape vision, strategy and then execute, measure, and refine. Rather than giving away bags of cash in my old job, I now ask for money from investors. Relationship dynamics are the same, minus the burden of extreme secrecy. Painting a vision for those in the company and those wanting to put their money in the company is vitally important, but so is being authentic, genuine, and a truth-teller. All the things that most of the outside world doesn’t understand as being critical to a handler-asset relationship are just as critical to relationships in industry. Judgment remains paramount.

In the Agency, as I got to more senior levels, I spent most of my days writing precisely worded emails to advocate for resources and challenge risk aversion. At times, it was an exhausting and never-ending match of written and verbal jujitsu, yet exhilarating when we got everyone on the same page and did the thing that needed to be done. I also dealt with a few difficult personalities focused on empire-building and metrics rather than running sound operations. You likely will still deal with this in industry, though there are far fewer layers and entrenched interests to deal with. Even in larger companies, people’s motives are usually quite obvious. Whereas in the Agency, there is a larger concentration of people forged under the flames of constantly “working angles,” some whose coups aren’t known until carried out.

Knowing how to navigate various stakeholders & interests, avoid landmines, and bring people together is an extremely useful skill in industry. If you’ve worked in a big bureaucracy and been a “doer” who knows how to communicate, work, and gain buy-in across an enterprise that may also be geographically dispersed, as well as with and against external third parties who are frenemies (or outright hostile), this will serve you well in industry. Talk about it when you’re seeking jobs and interviewing.

4. How did you get your job? Did you make any resume missteps?

I networked nonstop and ran a full targeting campaign for multiple companies to get to their CEOs. I didn’t have a resume when I was looking for jobs. I had to find senior people who had left who would vouch for me.

For Infleqtion (then named ColdQuanta), I was introduced to a former senior IC official who previously served on a separate board with the then-CEO of ColdQuanta, who made an introduction to this CEO. We met and I asked the CEO his challenges and outlined how I might be able to help, and indicated that I was having a lot of different conversations to determine my next steps. Five months later, the CEO called and said he may have a job for me and invited me to visit and speak with others in the company for their input. I received an offer shortly thereafter.

In another case, I did a cold outreach on LinkedIn to the person I suspected was the hiring manager for a job advertisement for a company that I liked. This was approximately three years before I left the Agency. The person told me they wanted someone with more business experience for the role, but then came calling three years later when another role opened that they thought would be a good fit. Ultimately, I met each layer up in that company, to include with the CEO. This all came in handy when negotiating salary, title, and function. From the many, many hours of networking hustle, I received two job offers, which happened in parallel, and I negotiated around the same title and compensation levels. Throughout the entire process, I forwarded them relevant articles and commentary on opportunities to demonstrate my value. Ultimately, I chose Infleqtion because of its mission, its people, and its reputation amid US Government circles.

Typically, if you’re going for a senior level role straight out of the Agency, your resume is not what will get you the job, and submitting one to a resume bank is not the right move. Even if you have a resume, it’s almost certainly written in government-speak, and probably more terrible than you realize. It likely talks about all the jobs you held (to the degree you can share) and the dates and maybe the general locations but says nothing about what you actually accomplished or how it specifically relates to industry. You probably won’t even get beyond the AI filter. Serving in a country and writing intelligence reports that go to policymakers, and “the President,” does not cut it. While it might make you a curiosity to them, industry rarely gets how it makes you useful. Some may want to meet you based on curiosity, and unless you can translate how it provides value, you’ll get stuck. Even still, they may fall back on what they know and choose someone with a lengthier business resume. Some will automatically discount anyone with government service, even the Agency, because they assume bureaucrat. Unless you’re trying to join a think tank or a company packed with formers, you’re unlikely to get very far with your basic resume and even in-person, you must describe your value proposition.

First, figure out which industry you want to work in, narrow it down to a handful of companies, and work hard to get intros at the senior levels of those companies. You have to go out and do a lot of networking to create your list and build your network. The highest leverage way to get hired is to find a way to meet a Board of Directors member, Advisory Board member, member of the C-suite (CEO, CTO, CFO, etc), and/or investor in the company and captivate them with a story of what you did, how you want to transfer this to industry, and ask them lots of questions about their personal experiences at that company and others. I had to do this virtually because of COVID, which made it more efficient, but in-person is always better for forming a stronger bond and making a good impression.

You’ll fail along the way. A learning point for me came early in my transition as I was speaking with a prospective VC about a job. My contact flat-out told me he didn’t understand my value proposition, even after I had tried to explain it in-person. He asked point blank, “How much money did you net the US Government over your career, what exactly did you do in order to get those results, and how would you bring me those same returns?” While the book The Billion Dollar Spy loomed in my head, I fumbled through the question. I most certainly did not recruit “a billion dollar spy” nor did anything that turned the tides of war. Yet, I had learned to craft and pull levers of power & influence usually only afforded to people with decades more experience & prominence in the private sector, and more so than my interlocutor. I fumbled the response. I don’t even recall what I said, but he didn’t reach out again (though now we’re friendly as we run in similar circles and were able to laugh about this recently).

If you get asked a question like this, my suggestion is to say something along these lines: It’s exponentially harder to be hired by the Agency than it is to get into Harvard, and not only was I hired based on an assessment of strong judgment and the ability to operate in ambiguous situations, I then was trained to do just that, and then did it for years. I was entrusted to create and carry out some of the most sensitive and most important missions that the U.S. Government conducts, often with little direction. Not only did I have to plan and do them, I had to do so in secret, with lives on the line, which is hard to put a price tag on. You can give me your toughest problem, and I will figure out how to solve it in record time with buy-in from those whom you rarely get buy-in, and position you for multiple shots on goal for future opportunities because I will have your company and sector wired. I can do for you what I did for our country: evaluate opportunity, mitigate risk, and make quick and smart decisions that attack problems differently than a typical insider would. Give me a couple hundred thousand of combined salary and operating budget, and I’ll turn it into millions of dollars in returns or investments within two years - not singlehandedly - but in a cooperative way that leverages many parts of the company. We’ll row in unison and we’ll row in the right direction. And I’ll do it all from a supporting role, with you at the helm and you as the ultimate decision-maker.

I know this sounds boastful, especially to you, humble public servant, but this is industry speak. Your experience is valuable and allows you to think differently. You know how to navigate situations that are highly relevant to the business world. You simply have to find the right target and find the right way to convey it.

I’m considering doing a live seminar for formers that goes into more specifics and contemplates various scenarios. If you have interest in this, please subscribe and let me know.

=================================

Subscribe now

It’s alluring to tackle a new challenge. Probably because in many ways, it’s starting anew. Like clockwork, twice a year, I buy gear for a new sport, and months later, it’s been used no more than twice. Sometimes my enthusiasm overwhelms my common sense. The excitement and desire for novelty and accomplishment isn’t limited to the recreational front.

For those addicted to striving and proving themselves professionally, little compares to landing overseas in a new country with the directive to build & achieve. Even better if you’re starting from scratch. I suspect it is what drew me and so many of my former colleagues to life overseas, or even the next headquarters assignment.

You begin to accumulate those successes, which turn into a professional reputation, which must be constantly curated and leveraged for the next assignment, critical for the next success, and so forth. In this cycle, there is nothing more crushing than seeing someone less competent than you getting an assignment you coveted. And there is nothing more glorious, perhaps other than nailing the recruitment of a valuable asset, than landing an assignment that allows you to prove yourself and level-up your professional reputation.

Stepping out of CIA was hardly me breaking this cycle of success seeking. In fact, it was just another iteration of it. If I look deeply enough, it was an attempt to distinguish myself even more. “See I can be successful here and here.” And because I left to work on a technology that is national security and mission related, I could also say, “and it’s in pursuit of something more than just myself.”

The wheel of one-upmanship and success seeking justified with “do gooding” rarely stops turning. I say this not because I’m deriding who I was or who I am now, but simply because I’m at a point in my life where I’m thinking more deeply about it. My job at CIA was to find others’ motivations and now I’m finding my own. Usually when I asked a source “why” they felt a certain way, I always asked “why” in response to each answer at least three times to get to the deeper motivation. We all start with superficial answers that sound good, and the older we get, the more we have to take caution not to believe our own bullshit.

Humans are meaning-making masters. It’s a good thing until it’s a bad thing, and the line between the two is different for everyone and always a bit blurry. Serving at CIA was deeply intertwined with my identity, and in many ways, still is. I had begun to summit a steep mountain that few people get to climb. Did I really want to give it up and start at the beginning climbing a new one? Ultimately, my ambitions were bigger than that building, and I’m still trying to make sense of what that says about me.

And this brings me to the topic of the action line. Last night, my Jewish wife roped me into watching a Jewish matchmaking show on Netflix. Normally I would spend my leisure time reading a non-fiction book on something like the rise of the shipping container industry or mindlessly scrolling VC Twitter. (The concept of leisure is problematic when you’re in the cycle of “optimizing”). Yet, I secretly enjoyed the 30-minutes of distraction from my otherwise very serious life and longings.

On the show, the matchmaker referenced “tikkun olam,” which is Hebrew for “repairing the world.” My eyes welled slightly hearing about it. That we seek to repair the world across space, time, cultures, and religions tapped an emotional reservoir inside me. While the underlying concept of tikkun olam was not new to me, there is something about hearing someone else express and label what we deeply know to be a shared sense of connectivity and community among us. (And to hear it explained beautifully as a tenet on a reality TV show no less.)

Much of what has motivated me has been this sense of “repairing the world.” I strive to be the “repairer,” and the world faces no shortage of people and things needing repairing. This desire, I believe, is innate for the most part, because altruism and cooperation is one aspect of survival. But it’s also taught, and it was a lesson ingrained in me from an early age by my own parents, couched in the Christian context.

Though, in many ways, even good and noble pursuits of repairing the world are usually at their core, selfish. Even the good we do is because of the feeling of goodness we derive from it. And many of us seek to repair others without looking inward to repair ourselves, first. This in no way means I think we should stop doing tangible things that repair the world (and let’s acknowledge, we also need to do things to stop breaking it in the first place). But, we should look deeper and ask why we do what we do. Can doing good ever be a function of pure love for the object of love, or is it always in relation, even if in a small way, to the feeling we get inside the self? Is this simply a “design advantage” of our DNA to keep us alive as a species? Is there a better way to link doing good to feeling good to maximize good in the world? And does the motivation even matter if the result is positive?

I think it does. Though, I won’t say no to a wealthy jerk building a local school even if it’s meant to ensure legacy, gain a taxi write-off, and alleviate guilt from a more frivolous lifestyle, while feeling a sense of goodness for repairing the world. But if we don’t also reckon with what we may be doing that is first breaking the world, no amount of repair can fix certain levels of brokenness. Too many people believe a charitable donation to repair is sufficient, yet don’t realize it causes more polarization. My wife explained that in Judaism the most noble way of charity is for the giver and receiver to both remain anonymous to each other. This is to remove a sense of indebtedness and a sense of superiority. A far cry from most acts of charity these days. Are we really being noble if we’re intending to be noble?

At CIA, there was a shared sense of noble pursuit. It was an opportunity to combine the selfish pursuit of success with the deep sense of wanting to repair the world, to help not just “my” people in the United States, but help others around the world protect themselves, most often from despots. Of course, here too, we must ask ourselves to think deeply about why, and ask ourselves why three times to move from superficial (though likely still, true) answers to the deeper ones. From the outside, conspiratorial mind, I can imagine this idea of a noble pursuit rings somewhat hollow. (Especially if you have no understanding of how hard it is to get reimbursed for the most trivial of operational expenses, yet think the US Government can run elaborate “covert action” plans continually ensuring the U.S. as a world puppet master). Or you believe CIA has led to more brokenness in the world than repair. But, that’s a topic for another essay.

Perhaps you’re a former colleague and a self-described “doer,” “realist,” “action-oriented,” and “don’t have time for all this philosophizing” type person. I get you, I’ve felt that way, too. I’m not a nihilist. The name of my site is “The Action Line” for a reason. Yet, there is a balance that I feel the need to strike more between thinking and success seeking and do gooding. Where are we virtuous versus mere virtue signaling, and how is this helping or harming our communities and society? Perhaps there is still a deeper notion that thinking about this dseeply, and documenting it for the world to see, will make me more successful. Either way, this is my new way of tikkun olam in a world of information overload, polarization, and what feels like a deep tearing of the fabric of our societies, our families, and ourselves. My goal is to write essays here, weaving in aspects of my past, to my current thoughts and future aspirations, and I hope you’ll join me.

Subscribe now

A day in the life of a CIA case officer can vary widely depending on the specific assignment and location. Case officers may spend hours poring over intelligence reports, meeting with agents and assets, conducting surveillance, and analyzing data to identify patterns and trends. They may also be called upon to participate in covert operations, which can involve anything from infiltrating a foreign organization to running a psychological operation to gather information or influence a target. Throughout all of this, case officers must maintain a low profile and avoid detection, often operating under false identities and taking extreme precautions to protect their cover and the security of their team and assets. Overall, being a CIA case officer requires a high level of dedication, commitment, and resilience, as well as a willingness to take on immense risks and make difficult decisions in the pursuit of national security.

-Above text: ChatGPT when prompted, “Write two paragraphs about what it is like to be a CIA case officer.”

-Above image: DALL-E AI image when prompted, “Modern 3D rendering of a compass with a Middle Eastern background.”

The challenge is the CIA remains the "collector of last resort," (HUMINT) yet is pulled in “open source” directions based on its legacy as the lead IC agency providing analysis. It both doesn't want to give up that mantle and is expected by policymakers to retain it. Further, multiple agencies have been given overlapping missions to CIA and they do it poorly, leading to turf wars, setting CIA leadership constantly on the defense.

Because of this, CIA leadership, even at the mid-ranks, wastes too many mental cycles on clinging to an ever-shrinking monopoly, which leads to activities that distract it from its intended focus on HUMINT. Thickening the plot, there are misaligned internal incentives for its officers: what's good for promotion and field assignments isn't necessarily good for the IC or for our intelligence competitiveness as a country.

All is not lost, but much must change. As the quote from John Maxwell goes, "everything rises and falls on leadership" and, in my view, the Agency has a major problem retaining leadership at the mid-levels. By the time you get to the senior levels, you see the people who have simply outlasted the rest. While they may be good at navigating bureaucracy and selecting what’s best for their “careers,” they are not necessarily the best at "leadership" nor actual intelligence operations (ie, “spying”). There are of course exceptions, but be careful who you ask - everyone views themself as the exception to the rule.

It's on the few true leaders at the CIA to fix this. But where do they even begin? Their days are filled with being on the receiving end of unclear and, at times, conflicting policy directives, putting out internal fires, as well as those lit by external agencies, and figuring out ways to reinforce their position, or climb to higher positions of authority, because they see themselves as the only ones able to hold their finger in the proverbial dam. 

But yet they must find a way. The good leaders that remain must accurately sift through what they can and cannot control. By design, they'll never control the DC policy regime. What firmly remains within their control is the internal incentive system and who they put into leadership positions. As former Secretary of Defense Mattis said, “Institutions get the behaviors they reward.” While constrained by the larger fact that the USG in general can't fire people, the opposite does not have to occur, which is promotion.

The CIA is expected to do hard things. And it does. Recruiting a foreign agent under the nose of a foreign country isn't easy, and I'd trust no other organization to do it as well. But this is nothing compared to the difficulty of holding its own people accountable for their failures by not promoting them, by not giving them plum assignments, and by not casting them off to another division as a way to "get rid of the problem." While this of course isn't limited to the CIA, it's human nature after all, the world's pre-eminent spy agency must do better, for all of us. 

Share

Sign up now so you don’t miss the first issue.

Subscribe now

In the meantime, tell your friends!