"In companies, you're judged by how well you handle your successes as well as your setbacks," reflected Chambers, adding that applies to both business and IT infrastructure models alike.

Speaking during a fireside chat with Box CEO Aaron Levie at Box's annual BoxWorks summit on Wednesday, Chambers hinted at another major roadblock hindering technological transitions -- notably that many of these shifts that used to occur every decade or so are now on a much faster turnaround timetable every three to five years.

Looking at a grander international scale, Chambers lamented that the United States is woefully behind -- in both the private and public sectors -- in upgrading digital infrastructures.

Highlighting there are a few exceptions in big business such as General Motors and Walmart, Chambers pointed toward greater successes in this regard across the United Kingdom, France, Germany and India.

"The United States is last major developed country in the world without a digital agenda," Chambers remarked.

Levie suggested that President Obama's administration understands the need for these changes, but Chambers countered the U.S. Government hasn't acted fast enough.

Cisco recently underwent a major transition of its own, at least on a personnel level. Chambers just stepped down as chief executive officer of Cisco after years in the role,replaced by Chuck Robbins at the end of July.

Positing he's looking forward to spending more time with his family as well as forging partnerships as executive chairman, Chambers admitted he's been thinking about the move for years, arguing that this industry is "notoriously bad at transition."