"Stop Managing Generations and Start Designing for Them" episode artwork

EPISODE · Jul 7, 2026 · 26 MIN

"Stop Managing Generations and Start Designing for Them"

from Looping You In · host The Nova Collective

We are still blaming generations for everything that goes wrong at work, and now there are more of them than ever to point fingers at. In this episode, Brynne, Andy and Keilah dig into why the generational narrative keeps resurfacing and what it is really standing in for: power, resistance to change, and who gets to define "professional." The bigger move is a shift from managing generations to designing for them. Managing is just trying to stay afloat. Designing is building something that can handle whatever comes at it. That means walking away from one-size-fits-all training, building learning around what an organization actually needs, and modeling the behavior you want to see at every level. Less labeling, more designing.Guest Bios:Andy Eninger ⁠⁠@Andy_Eninger⁠⁠ (Instagram)Andy Eninger is a Speaker, Comedian, and Learning Designer. He was the Head of the Writing Program for the famed comedy theater The Second City from 2011 to 2016. He helps individuals and organizations connect to their audience and each other through immersive, customized learning programs that combine storytelling, improv philosophy, rapid ideation, and foundational communication skills. In his creative work, he creates comedy with a mission of amplifying outsider voices and connecting people.Andy has worked with hundreds of organizations, including Walmart, Procter & Gamble, Leo Burnett, The History Channel, Cigna, State Farm, Visa, Verizon, Salesforce, SAP, Deloitte, Nike, GE, Walgreens, Merck, MetLife, Kellogg’s, and many more. His work takes him around the world to design and deliver learning programs in inclusion, collaborative leadership, executive presence, innovation, and storytelling. He was the chief designer of the curriculum for Nova Collective. For the Second City Works, he has spearheaded their learning programs in Storytelling, Selling Skills, and Diversity & Inclusion, and served on the design team for their work in Consumer Insights for brands.He continues to write, perform, and direct, with a focus on queer comedy, satire, and improvisation. Some of his favorite projects include: Ensemble member of Chicago’s GayCo Productions for 14 sketch comedy revues; Performing in the cast of Steamworks the Musical for the Annoyance Theater; Little House on the Parody as composer and director; Director and composer of Bandgeeks! A Halftime Musical; Creator of Sybil, a solo improvisational format; Pinque Pony, his two-man sketch group with husband John Loos; and Pony Boy, director and lyrics, for the Annoyance Theater. His play “The Last Castrato” has been produced at theaters in New York, Austin, and Phoenix.Andy holds a BS in Mass Communications and an MA in Playwriting from Miami University and studied film directing at the Academy of Drama & Film in Budapest, Hungary. He currently lives in Los Angeles with his husband and two dogs, Pearl and Barb from Accounting.Keilah ShanahanKeilah (Johnson) Shanahan is a strategist and facilitator who currently serves as Senior Director of Organizational Culture at a Chicago institution where she leads culture, belonging, and organizational development work. Before that, she spent three years as Strategy Lead at The Nova Collective, designing curriculum and coaching executive teams on building inclusive, high-functioning cultures across more than 35 clients. She holds a master's in Higher Education Administration from Indiana University Bloomington and a bachelor's in Communication and Political Science from Saint Louis University, and she stays active in Chicago's civic and nonprofit leadership community.

Episode metadata supplied by the publisher feed · Published Jul 7, 2026

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