Ilio is the Executive Director of Agile at Kaplan Test Prep. with about 10 years agile experience. 

Five years ago, Kaplan was almost entirely waterfall. Over the course of two years, he introduced agile in some pilot projects with good outcomes. These proved the case for an organization wide roll out. To date, all 12 development teams work in agile. Several non-development teams do as well - 8 total including marketing, publishing, and content.

Wendy's Notes From Interview

• After first year of rollouts across development teams, non-tech teams started agile adoption.
• Introduction of agile to complete autonomy varies depending on size and culture of team. Average 3 months non-software teams. “Processes are meant to serve you and not control you.” 
• Identify problems and baseline to improve before adoption and measure improvements as a result. 
• Use of surveys to measure more subtle points such as trust and happiness. Working with team gives the best sense — watching communication, collaboration, etc. 
• Most important questions: is throughput increasing? is team delivering more value?
• Coaches focused on agile roll out and now focused on how can our practices work better to build better products for our customers. 
• Culture shift — upfront planning -> hypothesis and goals with experiments in the marketplace and exercises. How can we deliver most stuff to how can we deliver right stuff
• Less lines of code, value higher.
• Technical debt gets reduced incrementally so value is continually added.

Shifting Culture From Waterfall to Agile

• Provide lightweight formal support mechanism while adopting.
• Weekly meetings with c-suite, 80% of time needed, solves problems team couldn’t solve on own. 3 months, 25% of time, 6 months meeting eliminated. Teams solving all problems on their own. Once in last 2 years, they thought they needed it for a problem, but ended up figuring it out.
• Lots of meetings — wean off naturally because teams were able to resolve issues themselves. “supporting teams until they don’t need support… goal is for teams to be able to solve problems themselves.”
• Opt-in approach — figure out challenges, give it a 3 month try, see how it works and then decide if they want to continue. 20 teams stayed with agile 2 teams opted out. “The ultimate goal is for teams to work well together and deliver most value you can.”

Thoughts on Dogmatic Agile

• Openness to try working differently in different context. Schools of thought that say what works best. “I don’t really care if its ‘agile’ I care if they are able to make good decisions, able to work in an iterative and incremental manner. If there are some things like portfolio management that helps the teams, thats ok. Pick whats right for your org and the context there."
• Balance is key — too much rigidity is bad, no framework or support is bad. 
• Cynefin Framework — http://en.wikipedia.org/wiki/Cynefin — being a “chef” with ingredients