Reflecting on Oz: Life After the CIA

I decided to resign from the Central Intelligence Agency late last year.

My decision was a bittersweet one: for over a decade, I worked as a political analyst, editor, and manager of analysts. It was a privilege and honor to be a part of the CIA. This is not to say that it is, or was, perfect: no organization is. At the end of the day, the CIA is a large federal bureaucracy.

For some time, when I talked to new officers, I joked that they would — over the course of their careers — go from seeing the Agency as the all-powerful Wizard of Oz to eventually realizing that the big green flaming head was an illusion and that they were the ones frantically pulling the levers behind the curtain.

It turns out that I lied to them.

The Agency is simultaneously the big green flaming head and a mass of men and women frantically pulling and pushing levers. Some levers are pulled to remarkable effect while, at the same time, other people are insisting that a working group be formed to formulate an organization-wide policy for lever pulling.

Snarkiness aside, the CIA is not the simple caricature that many hold it to be: like any organization, there is a bell curve of inspired leadership, managerial acumen, and intellectual prowess. In my experience, that curve is shifted further to the right than in many organizations, be they in the public sector or private.

One my frustrations is the recurrent and simplistic presentation of the Agency as a monolithic whole: there are a myriad of factions and coalitions around rank, bureaucratic assignments, and functional responsibilities. Diversity abounds even within those factions and coalitions. It is difficult to appreciate this diversity of perspective from outside of the Agency’s walls.

Many work to make the Agency more efficient and effective within the bounds of its missions and the oaths they swore upon entering the civil service. Like any organization comprised of competing interests, equities, and egos, though, it periodically makes decisions that simply defy logic and are embarrassing, at a professional — if not personal — level, to many of its staff.

Another of my jokes: that the CIA has intelligence failures is nowhere near as surprising as the fact that it has intelligence successes given the political, bureaucratic, and technological challenges its people face every day. Worth noting: those successes are often the result of the sheer force of human will.

For the past five or so years, I had the fortune of working with a small group of incredible analysts and contractors to reimagine how the Agency might align data, information technologies, and analytic methodologies to improve the quality of analysis in the face of unprecedented volumes of data, a growing percentage of which is available to anyone with a connection to the World Wide Web.

While I was not always as successful as I had hoped that we would be, the simple fact of the matter is that I loved — still love — the idea, if not the ideals, of the Directorate of Intelligence (DI; rebranded the Directorate of Analysis). It performs a critical function: thoughtful analysis without the pressure of supporting the political (or ideological) agendas of its parent organization.

For the DI, the ideal was the unapologetic pursuit of high-quality analysis; the Agency’s unofficial motto (“And you shall know the truth and the truth shall make you free.”) became a near-religious belief in “speaking [often unpalatable] truth to power.”

This ideal was not accompanied by angelic choirs: it was a rough-and-tumble, high-stakes game played by people with keen intellects, strong personalities, and sharp elbows. I often remarked that “In the dog-eat-dog world of the DI, every written product was a fire hydrant that people felt compelled to scent mark.” You had to defend a thesis every time you put pen to paper and, despite being colleagues, discussing the nuances of a piece of analysis was not always a collegial endeavor.

As an analyst, however, you accepted these lumps — and a myriad of other indignities — because you were trying to tell clear and compelling stories about the trends and events that were likely to affect US national interests and, ultimately, the safety and well-being of our fathers and mothers and siblings and neighbors and several million other people who you would never know.

Being an intelligence officer is rarely someone’s job: it’s their vocation. Their passion.

So, if being an intelligence officer is a vocation and a passion, why did I resign?

This is a surprisingly difficult question to answer.

Part of me points to the fatigue of working in a large, conservative bureaucracy: when I joined the Agency in the aftermath of the attacks of September 2001, there was a clear sense of urgency that superseded bureaucratic posturing and maneuvering. Unsurprisingly, that sense of urgency has diminished with the passage of time. I am certain some would dispute this assertion and I respect their contention to the contrary. The Agency is an innovative place, but — in my experience — the pace of innovation is often determined by its most conservative and risk-averse elements.

If I am to be totally honest, though, part of me simply despairs for my country. Politics — irrespective of the branch of government being discussed — has become a zero-sum game where we, as a country and electorate, lose out to the relentless and thoughtless pursuit of naively simplistic ideological agendas. I never thought that I would think back to the presidency of Bill Clinton and the days of the Republican Revolution as a model of reasonably effective bipartisan politics.

Now, there is no unifying American interest. There is red versus blue, and blue versus red. Any idea that does not fit neatly into an existing ideological narrative — no matter how fanciful or divorced from reality that idea might be — fuels a relentless stream of talking points based on half-truths and presented without context or consideration. Worse, pragmatic (or novel) solutions are all too often the basis for calling into question one’s commitment to a party (using any one of the countless ideological “litmus tests” in play) or one’s loyalty to the country.

This is no way to govern, or be governed, if one is serious about creating, nurturing, or contributing to the conditions for liberty, prosperity, and the pursuit of happiness.

But I digress.

All that having been said, would I do it again? Would I become an analyst, and a manager of analysts, again?

Part of me likes to think — or pretend — that the answer is a forceful “No.” The costs of working for the Central Intelligence Agency are high, particularly in terms of the sacrifices that one is required to make during (and after) employment and in terms of the scorn heaped upon the Agency — and implicitly its workforce — by unthinking critics (n.b., there are plenty of perfectly good reasons to criticize the CIA, but those criticisms often involve insights and investigation that are inconsistent with how information is compiled, packaged, and presented in today’s media).

The reality, however, is that I absolutely would: one simply does not turn down an invitation to Oz knowing the characters and adventures that you might have along the way.

Dennis J. Gleeson, Jr., is formerly a Director of Strategy in the Central Intelligence Agency’s Directorate of Analysis. He left government service in 2015 to pursue opportunities as a corporate strategist and technology evangelist in the private sector.