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John Brennan

CIA Director REVEALS All: Making Mistakes, Being a Leader, & Inside the Bin Laden Mission

What does it take to be the director of the CIA?

What does it take to be the Director of the CIA?

It’s no small feat to be in charge of a government organization, and the Director of the CIA has an incredible amount of responsibility. When it comes to national security, there really is no higher power or greater defense. That’s why it’s necessary to find the right person for the job. And for four years, today’s guest was that person.

Lao Tzu once said, “When you are content to be simply yourself and don’t compare or compete, everyone will respect you.” And Albert Einstein said, “Whoever is careless with the truth in small matters cannot be trusted with important matters.”

John Brennan lives up to those words. He is a man who commands respect, and he has proven himself to be worthy of trust with the most important matters. 

John was the Director of the CIA from 2013 until 2017, and during that time, he was responsible for intelligence collection, analysis, covert action, counterintelligence, and liaison relationships with foreign intelligence services. From 2009 to 2013, John was assistant to the President for homeland security and counterterrorism.

Throughout his time working for the CIA and protecting our country, John lived an intense life. With so much pressure on his shoulders, he learned to live with self-doubt. He also learned how to live a life of integrity — even in situations where trust was hard to come by.

In addition to the pressure of living life as an undercover agent, John was also the Director of the CIA during the mission to take down Osama Bin Laden. It was one of the most high-stakes moments in recent history, and John led the CIA to a major intelligence victory. I was excited to talk with John about his story, and today, we share that story with you.

Our conversation ranged far and wide — it was truly an honor to get to talk with John. I can’t wait for all of you to hear this one!

Who Is John Brennan?

John Brennan grew up in New Jersey as the son of Irish immigrants. In 1977, he earned his BA in political science from Fordham University, and in 1980, he earned his MA in government with a concentration in Middle Eastern studies from the University of Texas at Austin. Additionally, during his time in college, John spent time studying at the American University in Cairo, Egypt, where he learned to speak Arabic and spent time learning about Middle Eastern culture. 

As a result of his studies, John was the perfect person to lead the United States in the war on terror. He understood Middle Eastern culture, and he had a better sense than most of what it would take to operate covertly in that part of the world. Still, he had to rise through the ranks first!

In 1980, John responded to an employment listing in the New York Times and took a job working for the CIA. He served in numerous positions throughout the organization, most often working in counterterrorism intelligence. He also helped lead efforts to form the National Counterterrorism Center.

For a few years, John retired from the CIA and worked in intelligence in the private sector. However, soon after, under President Obama, John was appointed as the Assistant to the President for Homeland Security and Counterterrorism. During that time, John oversaw the use of drones to target terrorists in the Middle East. It was during this time that he oversaw the mission to target Osama Bin Laden — the founder of the terrorist group Al Qaeda.

Then, in 2013, John was named the Director of the CIA. During his tenure, John led the investigation into Russian involvement in the 2016 Presidential Election. And in 2017, John retired from the CIA.

Since then, he’s published a book: Undaunted: My Fight Against America’s Enemies, at Home and Abroad. This book contains an inside account of John’s career as a public servant with numerous stories about his fight to keep America safe. I’d encourage you to check it out!

But first, make sure to listen to this episode! John shared a ton of fascinating stories with me, and along the way, he shared a lot of wisdom too. I truly enjoyed this conversation, and I think you will get as much out of it as I did.

Inside the Life of a CIA Agent

Since I had an actual former Director of the CIA on the show, I had to ask him about the life of a CIA member. What’s it like operating undercover? What is life like when you work for the CIA?

First of all, John clarified the difference between a CIA agent and a spy:

“CIA officers who engage in conducting espionage are called case officers — they’re operations officers. They are the ones who are trained in the tradecraft of espionage and go out and try to recruit foreign nationals to spy against their countries. … It’s those foreign nationals who are referred to as the spies.” – John Brennan

That’s a key distinction — case officers or CIA agents are the people working for the United States and trying to recruit people from other countries to give us intel. The foreign people from other countries who provide us with that intel are the spies.

When CIA agents go overseas to try to recruit spies, they have entirely different personas. They operate undercover with false names and documents, and they’re specially trained to work with foreign nationals and try to convince them to, essentially, commit treason against their countries. Those agents learn a lot of techniques they can use to verify information and remain undercover. For example, they often use polygraph tests to confirm whether their spies are telling the truth. They also have to work very hard, along with the CIA operatives working here at home, to ensure their covers aren’t blown.

With so much secrecy in their lives, it’s easy to see why CIA caseworkers live with a certain amount of paranoia. It’s hard to maintain a level of inner peace and integrity when you spend so much time embodying a different persona. They’re constantly making sure they’re not being followed or tracked, and they have to conceal a lot of their lives. John revealed to me that the CIA has “Family Days” where agents get to bring their families to headquarters, and for many kids, those days are the first times the agents’ children learn that their parents work for the CIA.

So, how do CIA agents maintain a sense of peace and integrity? The truth is, it’s difficult. But at the end of the day, they operate with the knowledge that they’re doing everything to protect their country.

“Of course, we have to take care of our own country and our own people, but that doesn’t mean we do it at the expense of the rest of the world. … The more the United States is seen as being an advocate for the growth and prosperity of the world, I think … the better off we will be as well.” – John Brennan

Life isn’t easy for CIA operatives, but their work is so necessary. The efforts of CIA agents and employees in protecting our country and fighting terrorism are huge and have life-saving effects for Americans, so even though they live with a certain amount of fear and paranoia, agents choose that life to protect the country they love.

“Of course we have to take care of our own country and our own people, but that doesn’t mean we do it at the expense of the rest of the world.” @JohnBrennan  

Inside the Osama bin Laden Mission

I was excited to hear John’s insight into the life of a CIA operative, but more specifically, I couldn’t wait to ask him about the mission to take down Osama bin Laden. During his career with the CIA and as the President’s Assistant, John has several moments that he’s particularly proud of, but the mission to bring down Osama bin Laden is definitely at the top of that list. It was a huge moment in the fight against terrorism, and it prevented Al Qaeda from carrying out many attacks they had planned to follow-up 9/11.

So how did they do it? How did the CIA discover bin Laden’s location and take him out? The first step was realizing that they were never going to have all of the information:

“The intelligence business is really one where you really try to find all the different puzzle pieces, and you know you’re never going to get all the pieces, and you try to understand what those puzzle pieces reveal in terms of the picture.” – John Brennan

That’s the real work of the CIA — gathering what information they can and making the best decisions from there. Through their espionage activities, the CIA learned of a compound in a place called Abbottabad — which is the location of what John called “the Pakistani equivalent of West Point.” The CIA then observed the location to the best of their abilities, developed an idea of where bin Laden would be and when, and ultimately put together a team of Navy SEALs to carry out the attack.

The whole operation started in September, but the mission wasn’t actually carried out until May. That means that the CIA spent about eight months preparing, observing, and training for the mission. They had to select the right Navy SEALs to operate with the utmost secrecy. They had to plan the mission around the lunar cycle to give the team the maximum cover of darkness to help them invade the compound undetected. And most importantly, they had to work as a team and cooperate with multiple federal agencies.

“I worked very closely with Tom Dolan, who was the National Security Advisor in the White House and with President Obama and Vice President Biden and then Leon Panetta at the CIA and then Bill McRaven who was an Admiral who basically … oversaw that assault. … It was … basically a trifecta of the Department of Defense, the CIA, and the White House.” – John Brennan

For this mission to succeed, teamwork was key. John worked closely with those other men to carry out the mission successfully, and along the way, he learned a lot about leadership and teamwork.

Making Mistakes as a Leader

During his experience working in national intelligence, John worked on some high stakes missions, but he also made plenty of mistakes.

“I was rather efficient in terms of almost dictating to people. One of my responsibilities was to review papers that people would write, and so I would rewrite them the way I would write them. … I needed to understand that we all have our own, not just strengths and weaknesses, but we all have our different types of approaches and styles. … And also [I needed to] engage more. I was a pretty strong introvert, … and so I needed to sit down, talk with people, and then listen. I was a little bit too much of a loner.” – John Brennan

John may have been a little too strict and a little too silent at times, but over the years, he overcame those things to become an extraordinary leader. He learned how to make mistakes with grace and lead people with intelligence and wisdom. For John, it all comes down to integrity:

“Integrity is the distinction between right and wrong. I don’t say good and evil — it’s really right and wrong. … What is that North Star, what are those moral lessons, ethical lessons, what are those principles and values that really do define, I think, what it means to be a good person, a kind person, an honest person, a person who is not going to try to take advantage of others in order to advance their own personal interests? … Integrity is sort of a package of … how a person defines [themself] as well as how they treat others.” – John Brennan

At the end of the day, a leader with integrity treats those they lead with honesty and kindness. They don’t try to rig the system for their own maximum benefit — they’re more concerned with benefitting everybody. They definitely aren’t perfect, but when they make mistakes, they take responsibility, learn from them, and move on.

And when it comes to some of the more specific moral and ethical problems that come with living and working as a CIA agent, good leaders have to follow their own moral compasses. If their motivations are genuine and kind — if they’re doing their work with the aim of making the world better and safer for everyone, not just the United States — they’re able to lead with pride.

Why Team Building Is Essential

But here’s the other thing about strong, effective leaders: They know when to get help and work as a team. John shared with me a key piece of advice someone shared with him as he was rising through the ranks at the CIA:

“He goes, ‘John, I want you to know that you can make a mistake.’ He said, … ‘Now, there are some caveats to that. One is: I want you to make sure that you don’t make the same mistake twice because that shows you’re a learning person. … Secondly, if there is a decision that you have to make that, … if it goes wrong, it’s a shot below the waterline,’ — he’s a former Marine, so there’s a nautical reference there — he said, ‘you … need to raise it up [in] the chain of command.” – John Brennan

In other words, this man was saying that if ever John needed to make a decision that had important consequences for the whole organization, he should bring in other team members and superiors into it. Good, effective leaders don’t make those kinds of decisions alone — they rely on the people around them to work together and make the best choices for the good of the team.

John described it like a sports team: The teams who see the most success aren’t the ones who rely on one superstar to carry everyone else to the championships. They’re the teams who collaborate and use contributions from all the members to succeed as a whole. Likewise, when you’re working with a team — whether you’re a CIA agent or working in business — it’s more important to find people who can work together than to find superstars.

“The people I saw flame out in the agency who I thought had all the talent that they needed were the ones who were really that individual operator, the people that kept information from others, the people who tried to promote themselves at meetings, or the individuals who didn’t recognize that one of the real objectives of the agency is to have people empower one another. What can you do to help empower the work of other CIA officers? And what can others do to empower you? It’s that interactive system that really is going to define the success of the organization.” – John Brennan

Whether you’re in the CIA or working for any other organization, look for ways to be a team player. Contribute your unique skills and talents, and ask people who can help when you have to make large-scale decisions. Don’t try to operate alone! When you work together as a team, you’ll be amazed at the results you can achieve.

Why You Should Listen to This John Brennan Podcast Episode Right Now…

This episode was incredible. I am so inspired and amazed by everything that John has experienced and overcome in his life, and I admire the hard work he’s done to protect our country. He truly believes in and loves America, and he’s dedicated his life to keeping us safe and free. I just want to acknowledge him for his humility and integrity.

As always, I asked John for his definition of greatness, and he did not disappoint:

“My definition of greatness: Accomplishing something that is beneficial to more than yourself. To making a positive difference, to taking full advantage of one’s life to do something productive, something helpful, something important, something profound, something memorable in a good sense — making a contribution to humankind. And sometimes it can be something that is globally known and understood, but some things … are known only to a [relative] few. … Sometimes people see … opportunities that come to them, [and] they rise to the occasion.” – John Brennan

John Brennan definitely lives up to that definition. He has risen to the occasion countless times in his career, and for that, I think he’s achieved true greatness.

Thank you so much for joining me today! If you loved this episode, please let us know! You can post a screenshot on Instagram, and make sure to tag me, @lewishowes, with your greatest takeaways. And if you want to connect with John on social media, you can follow him on Twitter, @JohnBrennan. He’s not very active right now, but he may be one day!

Finally, don’t forget to check out John’s book, Undaunted. He shares much more insight into his experiences working with the CIA and with various Presidents, and I know you’re not going to want to miss that!

Until next time — keep striving to help others and to do it with integrity. When you do, you become truly great.

If you’re ready to dive into the world of CIA agents and learn how to make mistakes, be a leader, and understand more about the Osama bin Laden mission, join me right here on Episode 1,051 of The School of Greatness!

To Greatness,

Lewis Howes - Signature

“Greatness is accomplishing something that is beneficial to more than yourself.” @JohnBrennan  

Some Questions I Ask:

  • What does a day in the life of a CIA officer look like?
  • How do you trust information that you gain as a CIA officer?
  • How do you manage life as an undercover agent?
  • How many foreign undercover agents are there in America?
  • How do you have inner peace when working on such high-intensity cases?
  • What is the moment that you’re most proud of from working in the CIA?
  • What was the moment like for everyone involved in the mission when Bin Laden had been taken down?
  • Where were you when 9/11 happened and what was that situation like from your perspective?
  • How do you personally deal with self-doubt?
  • Were there any things that you saw people in government doing that you disagreed with when working for the CIA?
  • What is your definition of integrity?
  • How does someone keep their personal integrity while working in a profession that requires so much secrecy?
  • What is the Deep State conspiracy?
  • How do you build a good team?

In this episode, you will learn:

  • How to make sure you’re not being followed or tracked by other agents.
  • The months leading up to the Bin Laden mission and the most nerve-wracking 90 minutes for Brennan.
  • The details of possible attacks after 9/11 that were stopped by John Brennan and his team.
  • Which Presidents John was inspired by most while working with them.
  • Talking about personal integrity in work and sports. 
  • Talking about making mistakes and being a leader.
  • How the presidents grew as leaders during their terms.
  • How to deal with the responsibility of making incredibly tough decisions.
  • How you can tell if a person is lying to you or telling the truth.
  • The biggest challenge John overcame while working in the CIA.
  • Where our country would be if we hadn’t invaded the Middle East.
  • The three common principles that made the Presidents John worked with effective decision-makers and leaders.
  • The qualities you should develop right now if you want to become the President of the United States.
  • Plus much more…
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John Brennan

Transcript of this Episode

Music Credits:

Music Credit:

Kaibu by Killercats

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