The Department of Defense and Technical Leadership

A series of Medium posts based on my book, “An Approach to Machine Learning in Cyber Defense for the DoD”.

“Which unicorn would we rather search for? An operations person who understands tech? Or a tech person who is an amazing leader and can lead operations people?”

Finding leaders in the DoD who can operate in both the technical and operations space is extremely difficult. The good news, however, is this challenge is not just restricted to the defense department of the United States- it is an endemic problem in every organization, even commercial industry. The reasons are quite simple, yet hard to negotiate. The balance between understanding how to lead and inspire people and a deep knowledge of a technical field(s) is a hard cross-functional capability to come by. In the DoD, much like other cross-functional organizations, leaders must have enough of a background to inspire the ground operator or the SME (usually non-technical in nature in this case) as well as the engineers who support them. This is not a task for the faint of heart. It is also asking for a very specific type of person with the perfect mix of exceptional background as a subject matter expert and a simultaneously mastery of the art an organization is most known for.

The concept of credibility is something that must be considered in the training of future DoD leaders. Another consideration is incorporating the cross functional mastery of two fields; the technical and the operational. This is, of course, as long as the two fields remain separately defined…

Some interviewed for my study insist that combined arms programs are the solution to creating well rounded, inspiring leaders that can traverse both the technical and the operational realms. But at the end of the day, every leader in the DoD is the product of institutional mechanisms that various functional organizations instill in DoD recruits from the beginning of their careers onwards. This would require cross-functional fields to actually become cross-functional in nature- for, in the Army, the MOS fields to become blended from the start. Rather than admiring “cross-functional” from afar as the institution does today, the organization needs to actually implement cross functional as part of its identity.

So now that we have address cross-functionality, one must address how technical leadership is being recruited, instituted, and emplaced in the organization today. Are leaders with truly technical skills and work history being instituted in positions of leadership within the organization? Even as we discuss the cross-functional necessity in training and raising the DoD’s next generation of leaders, we also must examine the quality of technical training received by technical practitioners in the defense department. And when they grow up to become leaders… who are the types of individuals placed and promoted in positions of technical authority and leadership?

“[A DoD Chief Technical Officer] is an acquisitions person [who] never wanted to do anything else with their career and just wanted to hang out with all the cool tech people but was never in it to win it.”

The truth of the matter is, this is the the lack of technical background and a large degree of complacency that one could argue does not just exist within technical DoD leadership, but DoD leadership as a whole. This complacency is so entrenched in the establishment that one interviewee in an executive position (formerly an Army officer) jokes that he/she immediately discounts any DoD leader (military or civilian) bearing the title of “Chief Technical Officer. This is not due to bad memories- this is due to hundreds of engagements with DoD executive level leadership over the course of decades.

So where does this leave us? These typically technical positions produce nothing but an acquisitions program that purchases licenses for technical tools that may perform some technical functions. But really, nothing more.

“The Casual Observance of Technical Talent”

An excerpt from Essye Miller’s testimony to the Senate in 2018 commenting on the high turnover of technical employees in the officer of the DOD CIO [Source]

What causes this? A proposed conclusion was the environment in which the DoD fosters for technical experts. How could the DoD create the most optimal environment for technical engineers to thrive if decisions are being made by non-technical officers? How could the DoD foster the next generation of technical leaders if it cannot empower technical experts of low rank to become those leaders? A disturbing anecdote from a West Point graduate and Signals officer now working for a large Silicon Valley company pointed out that he/she commanded more respect once he/she took a position in a large tech company as a Site Reliability Engineer (SRE) than he/she ever did as a ranking officer in the service. The service member left the service in the first place believing more impact and influence could be made “from the outside” than within. As a result, the interview subject concluded- technical experts already present within the DoD are not empowered to lead. Their exploratory nature and their slightly non-traditional way of thinking about problems, speaking to one another, desired look or appearance and maybe even as far as hobbies that occupy their free time lead them to a place of oppression that ultimately causes technical talent to leave the service altogether.

“But subordinates are empowered in the military”

A team of “cyber warriors” at work. Source.

This statement could not be more incorrect, according to the study. Interview subjects went so far as to say that this applies to both technical and non-technical talent. This is attributed to many factors that are so inherent to the military’s structure, culture and nature one can only wonder if technical talent could exist in the military as a prized part of every area of expertise rather than a pool of nerds cordoned off to the side. The nature of the top-down rank system of the military and how leaders are trained to lead (and ultimately understand what leadership looks like) go exclusively against many of the personality traits hired for in an engineer by (for example) large tech companies in Silicon Valley. The risk averseness of the military again plays into the cultural aspect of fostering technical talent as well- because every leader is so risk averse to things they do not know or understand (like technology!) many do not provide the top cover for their engineers who desperately need more space to exercise their creativity to solve hard problems in unique ways. The power to chase and exercise curiosity (and a wide berth of independence) required to be given to engineers in order to allow them to actualize ground breaking moves forward in the technical fields are absolutely necessary, and absolutely do not happen on a large scale basis in the DoD. This is the amount of independence and exercise of creativity needed to go from solutions that sound great on a SITREP to technical solutions that actually tackle, address, and possibly solve mission challenges. Leadership training of officers and NCO’s alike do not humble those leaders to realize that even a private first class needs empowerment- a thought that oftentimes leads to reactions of dread and repulsion.

A photo from a design deployment I completed with Google.org in 2018. What are the noticeable differences in environment and personnel that you see here? Clothing? Devices? Workspace? Diversity of workforce?

So What Can Be Done?

At the end of the day, one interview subject sighed deeply, and putting their hands up said hopelessly: “While a system of rigid hierarchy is necessary in some areas of the military… that might not be compatible with the spirit of the engineer.”

So what can be done about this? What can resolve this conflict that prevents technical talent from staying in the service long enough to see time in leadership positions?

Maybe future posts on the subject will address the topic…! Stay tuned!

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