What Makes Training Stick When Your Team Spans Every Generation
Jerry Oliveira of Brooklyn Sports & Entertainment shares how the 70-20-10 model helps you build workplace training that sticks with every generation you lead.
Most workplace training is forgotten by the next week. Jerry Oliveira, Director of Training and Development at Brooklyn Sports & Entertainment, has a fix. He uses the 70-20-10 learning model to make sessions people remember, with mixed-department teams working real problems and games that teach the actual job. He also talks about how to tell a tired participant from a checked-out one, the human skills employees keep asking for, and why you should own your own story through change.
Jerry Oliveira is the Director of Training and Development at Brooklyn Sports & Entertainment, home of Barclays Center. In this episode of Herding Squirrels, Jerry walks through the Brooklyn Way, a four-hour culture training built on the 70-20-10 learning model, with cross-department problem solving and a scavenger hunt that taught real arena knowledge. He also shares how he tells real engagement from the performative kind, what employees ask to learn when given the chance, and the mentor who told him she wanted to see him doing her job. If you’re designing learning for a hybrid, multigenerational workforce, you’ll leave with practical ways to make training stick.
About Jerry
Jerry Oliveira is a senior learning and talent leader with nearly two decades of experience. As Director of Training and Development at Brooklyn Sports & Entertainment, he integrates modern learning technologies and drives culture activation for Barclays Center. He’s known for a people-first approach and for aligning frontline operations with executive strategy. At his core, he thrives on elevating the employee experience.
Find Jerry online: LinkedIn
Episode Highlights
[00:00:37] Helping people appreciate the skills they don’t know they have
[00:05:39] Putting the 70-20-10 learning model to work in a real session
[00:06:50] Inside the Brooklyn Way, from cross-department pods to a scavenger hunt with a purpose
[00:09:29] Designing for the most generations the workplace has ever had
[00:11:14] Performative alignment and the bias check that followed
[00:17:03] The two mentors who never accepted a first draft
[00:21:01] AI as a thinking partner and BSE’s internal AI labs
[00:26:09] Why you should own your narrative through change
Key Insights
Engagement needs intention: Fun gets people in the room, but the activity has to carry the lesson. The Brooklyn Way scavenger hunt sent employees to places like the cashless ATMs and had them record themselves using arena terms like “striking down” a section, so the game was the curriculum. (00:07:34)
Run 70-20-10 in one session: You don’t need a six-month program to use the model. Keep the formal piece in the room, build the social piece into mixed-department pods solving real scenarios, and make the experiential piece something people go do. (00:06:50)
Quiet doesn’t mean checked out: The participant who says “I don’t have anything” at the debrief may have given everything earlier. Before you label someone disengaged, check what the rest of their session looked like. (00:12:08)
Contract accountability up front: Jerry opens every session by asking the room to agree they own their learning. That small yes pays off later, because people now know asking questions is their job. (00:13:12)
People want human skills: Leaders tend to name hard skills. Employees keep asking for help with feedback and working across generations, because they know they have to work with each other every day. (00:15:33)
Develop people toward your job: A mentor once told Jerry she wanted to see him doing her job. When your people can perform at your level, you can delegate, and both of you get room for the next step. (00:19:13)
Make AI push back: Jerry set up his AI assistant to question him, including asking whether a draft sounds like him. Used that way, you get speed without handing over your voice. (00:23:19)
Own your narrative: Change is a roller coaster and you can’t control everything, including whether you fit a team. You can control the story you tell about yourself through it. (00:26:11)
Key Quotes
“Every learner is accountable for their learning, but L&D too holds some accountability for creating that environment so that they have the experience.” (Jerry)
“We all have something to learn from each other. And whatever someone brings to the table, everyone’s perspective provides value because it allows you to look at things differently.” (Jerry)
“That’s the key. It’s just getting folks to identify what they don’t see in themselves so that they feel empowered and they’re now performing.” (Jerry)
“You should always be in control of your own narrative. Don’t let anyone write your story.” (Jerry)
Resources Mentioned
The 70-20-10 learning model (70% experiential, 20% social, 10% formal)
The Brooklyn Way, Barclays Center’s culture training, named for the phrase from the Notorious B.I.G.
Barclays Center:
https://www.barclayscenter.com
Brooklyn Sports & Entertainment: [BSE URL]
Learning management systems (LMS) and learning experience platforms (LXP) with AI-driven assessments
Gemini, ChatGPT, and Claude
About Herding Squirrels
Herding Squirrels is a podcast about modern teams and change, where we uncover the nuts and bolts of what makes teams actually work. Subscribe wherever you listen, and leave a review if this conversation was useful.
Herding Squirrels Ep 14 w Adam Tal
Herding Squirrels Ep 13 w Oliver Gray
Herding Squirrels Ep 12 w Louie Celiberti
Herding Squirrels Ep 11 w Nicole Tibaldi
