Building an Agile Future: Finding Stability in Digital Evolution with Roland Rainey, Jr.

Organizations crave structure and familiarity. And both are hard to come by—especially if you’re working in tech. So how do we simultaneously change and create order, all while living in an increasingly destabilizing world? 

That’s what Roland Rainey, Jr. and I tackled in episode two of Building an Agile Future: A Modern Digital Leaders Interview Series.

Roland is a proven leader with 26 years of experience. And his resume is as long as it is deep.

He’s served the Space Force and the United States Air Force. He’s also been a three-time unit commander, senior evaluator, adjunct professor, football coach, ESPN Radio talk show host, and, by the way, that’s just the first page of his CV.

Roland’s also overseen multi-million dollar operations, including satellite command and control programs, is the former Commander of the National Reconnaissance Office Operations Squadron (NOPS), and former Deputy Director for the Executive Actions Group for the Chief of Space Operations. Currently he is the Director of Strategic Business Development for Kratos Defense and Security Solutions.

To say Roland knows a thing or two about evolution is an understatement considering he’s made a career out of it.

We wanted to find out what Roland’s three decades of experience have taught him about leadership, how companies can evolve and stay relevant, why great speeches don’t lead to great changes, and more. 

Here’s what Roland had to say.


"I think one of the biggest lessons I've learned is that you must have a strategic mindset rooted in evolution," Roland says.

Why? Because we live in an era where technology changes daily, which makes five- and 10-year plans obsolete before they’re even written.

To keep pace, organizations must be prepared to evolve. But to outpace, organizations must develop a strategic mindset rooted in evolution. 

“Whatever technology you're investing in now will, at best, change in two years. Then it will change again the next year,” says Roland. So whether they like it or not, organizations better get comfortable with change and ready themselves to “evolve as fast as technology does," he says. 


Making changes and evolving is just the tip of the iceberg. To transform, Roland argues that organizations must first understand the digital movement's history.

It started with the digitization of coding and then moved into a space where organizations transformed business processes into a workflow and automated them.

Only once you understand where technology was (as opposed to where it is), Roland says, “are you ready to transition into a space where humans and machines work in unison?” 

Understanding that history, Roland says, “puts organizations on the path toward transformation.”


Most organizations are scrambling to keep pace with emerging technology, yet government organizations still lag behind. Why?

According to Roland, it’s because they’re inherently change-resistant, and much of that caution is tied to security concerns. The funny thing is that government organizations already technically operate in a cloud environment.  

If there’s one thing Roland would like to see, it’s the government getting on board and realizing they’re getting left behind. “Digital is the way of the world,” he says, “and if you’re not part of the movement, you’re behind it.”


One of the biggest challenges organizational leaders face is influencing swift and successful change. And while many leaders know the industry buzzwords and are happy to talk about transformation, few are able to create top-down change.

“A lot of leaders talk about transformation,” says Roland, “but what tends to happen is that they fail to achieve cross-organizational buy-in, and change stops once it hits middle management.”

So leaders must make a hard decision: Are they going to “be a part of the new wave or jump ship?” Or, as is often the case, will they let ideas flounder and kick the can down the road?


If there’s anyone you should ask about time management, it’s Roland. Over the last three decades, he’s served as a three-time unit commander, senior evaluator, sports talk radio host, event associate for the San Francisco 49ers, and more.

So how does he do it all? More importantly, how does he do it so well while maintaining a cohesive family life?

“Time management,” he says. "Unless you understand your time management skill set first, then no matter what you do, you won't be effective at anything," says Roland.

For Roland, personal time is critical. Dead time? Not so much. But what’s the difference?

Personal time constitutes any activity that promotes “health and mental clarity.” In other words, choices promoting “full engagement or a sound mind.” Dead time is a little harder to identify, Roland says, because when we engage in it, we often “think we’re doing a task, but four hours later you look up, and you’ve accomplished nothing more than wasting time.” 

In addition to cutting out dead time, Roland is also adept at setting priorities. "No matter what anyone tells you, not everything is a priority,” he says. And if the people surrounding you don’t get that, “they’re hindering your time management skill set.”

Thank you for a thought-provoking conversation, Roland!