A Working Session Where Participants Build, Connect, and Deploy Their Own AI Dream Team.
Date & Time: Thursday, October 2
Location: 1449 S. Michigan Avenue
Hosted by: Entrenuity
Workshop Overview
Most people build one AI persona and stop there. In this working session, partnered with Entrenuity, I took local entrepreneurs and professionals further by showing them how multiple personas, built with consistent structure and connected through a shared framework, function together as a coordinated AI Dream Team.
The session was hands on from the start. Participants worked through four progressive persona templates, from Basic to Cutting Edge, building and improving their personas in real time against actual projects and workflows they brought into the room. Each round added more structure, more specificity, and more capability. By the end, every participant had assembled a complete AI Dream Team ready to assist them with real work.
What Participants Left With:
- A working understanding of how persona categories create consistency across generative AI tools.
- Multiple personas built and tested during the session against their own real projects and workflows.
- A Prompt Engineer persona that maintains alignment and consistency across their entire AI Dream Team.
- A full library of pre-made personas to kick start their AI Dream Team after the session.
- A complete, customized AI Dream Team ready to assist with real work.
Inside the Session
The session opened with two grounding questions that set the tone for everything that followed: what participants wanted to learn about personas, and which project or workflow in their work was stuck where AI could help. Those answers became the raw material for the entire working session.
From there, I walked participants through four progressive persona templates, starting with a Basic template and building toward the Cutting-Edge framework I use in my own work. Each round was a live build. Participants worked in pairs, applied each template to a real problem they identified at the start, and shared their outcomes with the room. The progression made the difference between each template level visible and immediate because participants could feel how each additional category made their persona more capable and more consistent.
The second half of the session focused on coordination. Each participant built their own Prompt Engineer persona, which functions as the consistency layer across an entire AI Dream Team. I then demonstrated how the Prompt Engineer works alongside other personas, including a Business Development, Project Manager, Admin Assistant, and Communications persona, before participants returned to the problem they identified at the start of the session and used their assembled Dream Team to solve it.
The session closed with a Hemingway Bridge exercise where every participant wrote one insight from the session and one real project where they would put their AI Dream Team to work next.
Key Takeaways
1. A persona is the right start, but categories transform it into your assistant.
2. Consistency across personas is what turns individual AI tools into a coordinated team.
3. Your AI Dream Team is only as strong as the guidance you give it.
Participant Reflections
“Logan’s workshop convinced me that we should be using AI as a resource, not something I should be apprehensive about.”
Stay Connected
If you’d like a recap of the session, a copy of the persona template, or want to bring this workshop to your organization, let’s connect:
LOGANMONDAYAI 