Commentary: Despite seemingly overwhelming organizational inertia and dysfunction, the U.S. Air Force’s chief software officer figured out how to succeed. Here are lessons from his resignation letter.

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And you thought your IT problems were bad. Nicolas Chaillan, the first chief software officer for the U.S. Air Force, had more than 100,000 software developers working for him, delivered the largest open source software release in U.S. Department of Defense history, enabled Governors for weapons systems and more.

But on September 2, 2021, Chaillan quit, fed up with “hearing the right words without action.” For anyone who has worked in a large organization, Chaillan’s complaints will sound familiar. But he also gives clues on how to overcome the bureaucratic ballast that seemed to have kept the U.S. Air Force from soaring.

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Oh, so many problems

No matter where you work, there’s no shortage of things to complain about, right? I’ve worked at places where resourcing was scant (hard to get things done) or overly abundant (hard to prioritize), and I’ve done my share of complaining about it all. Chaillan’s world within the U.S. Department of Defense offers familiar, if larger in scale, problems to those many of us confront.

Take, for example, leadership. Many of us will have had a similar complaint to this one Chaillan offered: “The Department of Defense, overall, needs to stop staffing Enterprise IT teams as if IT is not a highly technical skill and expertise.” He adds: “Please stop putting a Major or Lt Col. (despite their devotion, exceptional attitude, and culture) in charge of ICAM, Zero Trust or Cloud for 1 to 4 million users when they have no previous experience in that field.” Ever had a boss without the requisite experience to make sound judgment calls? Of course you have.

(And have you ever complained that things would be better if only you were given a promotion? Yes, you have. And so did Chaillan: “Yet with my 22 years of expertise running IT innovation, I was underutilized and poorly leveraged by the DOD…”.)

Or what about feeling like you’re so burdened with basic nuts and bolts issues that you can’t focus on bigger, more strategic jobs? Chaillan feels your pain, saying he was “unempowered to fix basic IT issues” causing them to “run[] in circles trying to fix transport/connectivity, cloud, endpoints, and various basic IT capabilities that are seen as trivial for any organization outside of the U.S. Government.” Pretty much every organization gets bogged down in the minutiae, which is why we feel Chaillan’s pain. We share it.

Chaillan may have good cause to complain, as he stated: “I am just tired of continuously chasing support and money to do my job.” But this isn’t particularly different from what you or I may grumble about in our own jobs. Chaillan’s problems may have a bigger scale, but that they’re not fundamentally different from ours.

What is perhaps different, and much more interesting than Chaillan’s laments, is how he and his team delivered positive change despite all these hurdles.

Moving really big rocks uphill

One important thing Chaillan championed was the introduction of a managed service for deploying applications. Despite the unfortunate use (and re-use) of DevSecOps, which simply means integrating security throughout the software development/deployment lifecycle, this “DoD Enterprise DevSecOps Managed Service’s” more approachable name–Platform One–gave teams somewhere to deploy code with minimal obstacles. Given the U.S. government’s well-earned reputation for bureaucracy, Platform One helped to accelerate a shift to modern, secure development practices.

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In other words, rather than beat teams with the proverbial stick (“you must do things this way”), Chaillan gave them a “carrot” to provide an incentive to do things differently. Nor was this all that he did.

“We created the DoD Enterprise DevSecOps Initiative, certainly the largest DevSecOps engagement in the world, within the most complex organization in the world.” How? “We demonstrated that a small group of people can turn the largest ship in the world through grit, wit and hard work.” In some ways, this initiative may have been aided by the military’s top-down approach to solving problems. But it also was made possible by encouraging teams “to start small and build…up their capabilities, progressively, striving for continuous process improvement at each of the eight lifecycle phases,” as outlined in the DevSecOps Fundamentals document.

In other words, the direction (and encouragement) may have been coming from Chaillan/the top, plenty of room was afforded teams to learn at their own pace. Every organization can learn from this approach.

Among these and other suggestions, one of Chaillan’s most basic, and insightful, suggestions comes down to empathy. In a talk at an Air Force luncheon, he said, “It has always been important to use the [Government Furnished Equipment] device, use the normal network, feel the pain that the Airmen feel when they use those tools, because if you’re not feeling the pain, you’re not going to fix it.”

The best place to start fixing problems is by first feeling them in the same way your users will. That’s a great principle to guide you, whether you’re the Chief Software Officer for the U.S. Air Force or someone in IT for a small business.

Disclosure: I work for MongoDB, but the views expressed herein are mine.

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