“An organization has to first understand how agile works on a small scale, because the way I look at scaling agile is really taking those principles, those things that work at the team level, and just figuring out how to make them work on a larger scale,” he said.

In addition, since enterprise-level agile requires participation from everyone in the organization, everyone needs to embrace it, and achieving that executive support and participation is required. Executive support will help solidify that movement to agile is the right move, according to Cunningham.

“It is not only about an understanding of the agile principles and mechanics, but also the extent to which there is a demonstrative willingness to embrace it and to undergo the necessary organizational change,” he said. “Those two things are really good at indicating the extent the organization is not only ready to embark on something, but also [are] a leading indicator on how successful they might be.”

Another good way to measure how the company’s current business strategy is performing can simply be by answering these questions: “How does work flow to your teams? How far into the future do you plan? Do you include people from outside IT or engineering in your planning? What happens if the world changes after you plan?” said Rally’s Hudson. “And finally, you should ask yourself if you can afford not to adopt agile practices across your organization. Are your current methods for working keeping up with the rate of change and disruption influencing you?”

The answers to these questions can help gauge where the company is at right now, but perhaps one of the most important question an organization should ask themselves is “Do you want to keep your business alive in the 21st century? If so, then you’re ready for agile,” Hudson added.

Although Larry Maccherone, director of analytics and research for AgileCraft, argues that an organization is never really ready. “You’ll likely never be as ready as you wish you were,” he said. “The best course is to decide that you are going to do it, and then essentially do what you need to do to get ready.”

Maccherone adds that more and more organizations are seeing success with “big bang” agile transformations. A big bang agile approach consists of taking a leap and rolling out the deployment all at once, rather than the recommended small start into scaling.
“You would likely need expert help to take this approach, but it does offer the quickest path to reaping the benefits of scaled agile,” he said.

Prerequisites for agile
While Maccherone doesn’t think organizations will ever be completely prepared to scale agile, there are some basic principles and practices that can make the transition smoother.
According to Maccherone, there is a critical stepping stone organizations should use. “The first critical step is to orient around the product or service that you provide rather than the activities that the various workers perform,” he said. To achieve this, organizations should change their periodic planning activities, and eliminate organization obstacles to product or service orientation, according to Maccherone.

“If the testers, analysts, UX and Ops folks all think of themselves as working for their functional manager rather than on an agile team that is focused on a product initiative, you’ll never accomplish that first critical step,” he said.