Invest in Strategic Thinking: Interview with CIA Spymaster Jack Devine

I recently went one on one with Jack Devine. Jack is a 32-year veteran of the Central Intelligence Agency, having as both Acting Director and Associate Director of the CIA’s operations outside the United States. Jack headed the CIA’s Counternarcotics Center during the time drug kingpin Pablo Escobar met his demise and ran the CIA’s Afghan Task Force, which drove the Russians out of Afghanistan (colloquially known as “Charlie Wilson’s War”) and was CIA’s largest covert action operation up to that time. Jack is the recipient of the CIA Director’s Medal, the Distinguished Intelligence Medal, and several Meritorious Awards, and has written widely on intelligence, including in his new book, Spymaster’s Prism: The Fight Against Russian Aggression.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

Jack: Adam, as way of background, I was born in Philadelphia, went to Philadelphia area colleges (West Chester University (BS) and Villanova (MA), served as a lifeguard for 5 years on the North Wildwood Beach Patrol, and taught high school (history and economics) in suburban Philadelphia. At the time, I had my eyes set on becoming a college professor. I had never considered leaving the area. Let alone joining the CIA. But in 1967, for my birthday, my wife Pat gave me a copy of David Wise’s Invisible Government which was a forerunner of today’s “deep state” conspiracy. It highlighted the CIA’s covert action role in the Cold War. I’m sure my reaction was different than Wise had anticipated. I found his description of CIA’s fight against the communists and the use of covert action very intriguing. Consequently, I penned a letter to the CIA expressing interest in joining the fight. Within a few months, I found myself going through CIA operational and paramilitary training, and eventually being assigned to Santiago, Chile as a CIA operative. In fact, I was still stationed there in 1973 when Salvador Allende was overthrown. It was a far cry from the aspirations of my 20’s.

 All of us face failures and setbacks every day and hopefully we grow from each experience.. But there were a few key challenges during my time at CIA which greatly impacted on my thinking about the business of intelligence which are detailed in my two books – Good Hunting and Spymaster’s Prism. To site just a few examples of these experiences and challenges, I would underscore the Allende coup, the Iran Contra Affair, the struggle against the Russians in Afghanistan in the 1980s (Charlie Wilson’s War), the hunt for the spies inside CIA (Rick Ames) and FBI (Robert Hanssen), and the tracking down of the Colombian Narco Kingpin Pablo Escobar.

Adam: What would surprise people most about the CIA and about the life of a CIA agent? 

Jack: Unlike the Hollywood portrayals of James Bond and the media’s sensationalization of CIA covert activities, the biggest misunderstanding about CIA is the belief that the Agency is rogue force working outside the lines of US policy and laws. The CIA , in fact, is much more legalistic in its activities than generally perceived by the public. People would be surprised to learn that all the highly publicized and controversial activities of the CIA -- such as the Bay of Bigs, the Iran Contra Affair and the overthrow of the Allende government in Chile -- were all approved by the President. Moreover, since the mid 70’s the President’s approval has been required in writing for all covert activities and these activities have to be briefed to the Congress quickly thereafter. It is called a Presidential Finding. I know of no CIA covert action operation that wasn’t explicitly approved by the President.

As far as the life of CIA spymasters is concerned, again unlike the movies, spymasters have families and are involved in all the demands of everyday life like most people – school meetings, kid’s sports events, community activities, food shopping, household chores, etc. While there are unique wrinkles in carrying out daily activities under cover, spymasters resemble your neighbors who are parents and spouses and like everyone else must balance the joys, trials, and tribulations in their lives as do ordinary Americans.

Adam: What were the best leadership lessons you learned from your time in the CIA?

Jack: While the profiles of most CIA operators are relatively similar in IQ, education and life experience, there is a relatively small percentage of officers who have the interest and intellectual wiring to think in strategic terms. There is a greater paucity of strategic thinking than I had imagined early in my career. Most of the workforce’s energy and time is put into tactical thinking and activities. I have never solved the riddle why that is the case. However, over the years, I have come to see this tendency replicated in all walks of life, including the private sector.

Adam: What are your best tips on the topics of persuasion and relationship building?

Jack: The art of persuasion and relationship building requires listening and asking the other party about themselves all the while selectively inserting how compatible your product is to their interests and goals. The objective is to create an ambience in which the other party wants to volunteer to participate in the activity you are selling. This is true in the intelligence business as well. The hard sell works far less effectively on the high end of recruitments, especially when you are looking for a lasting commitment.

Adam: What do you believe are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

Jack: At the top of the pyramid of leadership qualities, I would place strategic thinking and an entrepreneur mindset. Regarding entrepreneur mindset, it is the quality that combines ambition, energy and desire to grow whatever opportunity, project challenge is placed in your hands. Those who simply work out of the “in-box” are never destined to leadership roles.

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

Jack: The three most important tips are: (1) Invest in strategic thinking (2) Surround yourselves with talented staff who are willing to speak out on issues and to challenge conventional wisdom (3) Improve your verbal and written skills and pay careful attention to express your goals, values and vision. Don’t delegate this task.

Adam: What do you hope readers take away from your new book?

As far as Spymaster’s Prism is concerned, there are 13 Chapters devoted to intelligence/policy lessons. But the key theme in both books highlights the need to understand the principles for effective covert action which apply to most of life’s endeavors as well. This theme is the modern adaptation on the age-old theme for a “ Just War”. It is necessary to have an ethical/philosophical basis for undertaking any covert action.

Adam: What is the single best piece of advice you have ever received? 

Jack: When I was 15 years old, a friend of my father, who was the head of all the building trade unions in the Philadelphia area, pulled me aside at a retreat event and said, “remember before you get out of bed every day, think hard about the strategic decisions that you need to make that day”. It obviously stuck with me over many years.

Adam: Is there anything else you would like to share?

Jack: A rich understanding of history is needed more today than ever, if we hope to avoid the mistakes of the past. Part of that history is to understand the key role that CIA plays in our national security and to appreciate how many unsung CIA heroes put their lives on the line every day for our country and its democratic values.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

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