// session guides
Detailed agendas, facilitator notes, live exercises, and prompt templates for every session. Built so any chapter leader can pick one up and run it.
Designed for chapter chairs, learning officers, and executive directors evaluating the program — and for hosts preparing their sessions.
June 2026
Get everyone on the same page. Fast. This month is about demystifying the tools, understanding what's actually useful, and building confidence to experiment.
Host: Jeremiah Gutierrez @ UNCS, Fort Lauderdale · Virtual + In-Person
Welcome & Ground Rules
Introductions, Chatham House Rule reminder, session format overview. Quick poll: "Which AI tool do you currently use the most?" (show of hands or live poll)
The Landscape in 5 Minutes
Quick primer on the three platforms: who built them, what they're optimized for, pricing tiers relevant to business use. No slides — just screen-share the actual products.
Live Smackdown — 5 Rounds
Same prompt, three tools, live on screen. The group scores each response. Facilitator runs all three side-by-side (three browser tabs or split screen).
Hands-On: Try It Yourself
Participants pick one prompt from the exercise sheet and run it in whichever tool they want. Share what surprised them. Pair up if someone doesn't have access.
Open Q&A & Discussion
Burning questions from the room. What's everyone actually using day-to-day? What have you tried that flopped? Virtual participants can drop questions in chat.
Wrap & Next Steps
Recap the scorecard results. Preview July sessions. Invite members to host their own. Share resource links.
Each round uses the same prompt across all three tools. The room scores on: accuracy, usefulness, clarity, and speed. Keep a running tally on a whiteboard or shared doc.
Round 1 — Strategic Writing
Board Meeting Prep
"Draft a 3-paragraph update for my board on Q2 results. Revenue was $4.2M (up 12%), but we missed our hiring target by 3 roles. Tone: confident but transparent."
Round 2 — Research & Analysis
Competitive Intel
"My company does commercial logistics in the Southeast US. List our top 5 competitors, their estimated revenue, and one thing each does better than us based on public info."
Round 3 — People & Comms
Difficult Conversation Prep
"I need to tell my VP of Sales that I'm restructuring his team and reducing headcount by 2. Draft talking points that are direct, empathetic, and legally sound."
Round 4 — Data Interpretation
Financial Snapshot
"Here are my last 6 months of P&L data: [paste table]. Identify the 3 most important trends, flag any concerns, and suggest 2 questions I should ask my CFO."
Round 5 — Creative / Wild Card
AI Policy Draft
"Draft a one-page AI acceptable use policy for a 50-person company. We want to encourage experimentation but protect client data and IP. Keep it practical, not corporate."
Setup (before session)
Running the Smackdown
Common Questions to Prepare For
Great for chapters with members in similar sectors. Pick one industry and go deep.
Industry Check-In: What AI tools is everyone in the room already using? What problems are you trying to solve?
Use Case Deep Dive: Walk through 3–5 real AI use cases specific to the industry. Examples: real estate (market analysis, listing descriptions, comp reports), healthcare (patient communication, documentation), finance (financial modeling, regulatory summaries, risk assessment).
Live Build: Pick one use case and build a workflow together. Start with a raw prompt, iterate until the output is genuinely useful, and document the final version for everyone.
Roundtable: Each member shares one AI win or one frustration from their business. Open discussion.
How to set guardrails for your team without killing momentum. Leave with a draft you can actually use.
The Policy Landscape: What are companies actually doing? Quick survey of the room: who has a policy, who doesn't, who has an informal one? Share examples of real policies (sanitized).
The Four Pillars: Walk through the key areas every AI policy should cover: (1) data classification — what can and can't go into AI tools, (2) approved tools and tiers, (3) output review requirements, (4) disclosure and attribution norms.
Live Draft Exercise: Using an AI tool, each participant generates a first draft of their company's AI policy. Then pair up, swap drafts, and critique: "What would your general counsel flag?"
Discussion & Q&A: Share the best drafts. What's the right level of restriction vs. freedom? How do you handle shadow AI (employees already using tools without permission)?
July 2026
For members who've played with the basics and want more. This month focuses on prompting mastery, team rollout strategy, and the tools that are changing the game right now.
July is wide open for chapters to claim. Host a session →
How to talk to AI like a power user, not a tourist. Build your personal prompt library during the session.
The Prompting Gap
Why most people get mediocre results from AI: they're asking questions when they should be giving instructions. Show a bad prompt vs. a great prompt side-by-side.
The Anatomy of a Great Prompt
Teach the R-C-F-C framework: Role (who should the AI be?), Context (what does it need to know?), Format (how should the output look?), Constraints (what should it avoid?). Live examples for each.
Executive Prompt Library — Live Build
Participants build prompts for real tasks they do every week. Categories:
Board & Investor Comms
Update letters, meeting prep notes, Q&A anticipation
Team & People
Performance reviews, hiring criteria, team restructures
Strategy & Planning
SWOT analysis, market entry briefs, competitive research
Operations & Process
SOPs, vendor evaluations, decision matrices
Advanced Techniques
Chain-of-thought prompting, iterative refinement, few-shot examples, custom instructions / system prompts. Demo each one live, then let participants try them.
Share & Steal
Everyone shares their best prompt from the session. Compile into a shared doc that all participants keep.
# Weekly Team Update
Role: You are my chief of staff drafting an internal memo.
Context: Our team of [X] just completed [milestone]. Key wins: [list]. Blockers: [list].
Format: 3 paragraphs. Lead with wins, then blockers, then next week's priorities.
Constraints: Under 250 words. No corporate jargon. Tone: direct and motivating.
# Decision Analysis
Role: You are a strategic advisor who challenges assumptions.
Context: I'm deciding between [Option A] and [Option B] for [situation].
Format: Create a decision matrix with criteria: cost, speed, risk, team impact, reversibility.
Constraints: Score each 1-5. Include a recommendation but flag what I might be missing.
Key insight: Most executives write prompts like Google searches ("AI policy template") instead of instructions ("You are a compliance consultant. Draft a..."). The single biggest unlock is teaching them to give context and constraints.
Don't over-teach: Stick to 3–4 techniques max. The goal is to build the muscle, not memorize a framework. If they leave with 5 great prompts they'll actually use, the session was a success.
Pro tip: Have participants start by writing their prompt on paper before typing it in. This forces them to think about structure before hitting enter.
Change management for AI adoption. How to lead without mandating. What policies actually work vs. what slows everyone down.
State of the Room
Where is your team on the AI adoption curve? Quick framework: Unaware → Curious → Experimenting → Integrated → Dependent. Each participant places their company on the spectrum.
The Rollout Playbook
Four approaches that work at different company sizes and cultures:
Peer Workshop: Your Rollout Plan
Break into groups of 3–4. Each person spends 5 minutes sharing where they are and what they're thinking. Group gives feedback and ideas. Then each person writes a one-paragraph rollout plan for their company.
The Hard Questions
Facilitated discussion on the real obstacles: "What if employees are scared AI will replace them?" "What if someone feeds confidential data into ChatGPT?" "How do I measure ROI on AI adoption?" "How do I handle the person who refuses to use it?"
Commitments & Accountability
Each participant shares one concrete action they'll take in the next 30 days. Optional: buddy system for follow-up accountability between now and the August session.
This is a discussion-heavy session. Resist the urge to lecture. Your job is to facilitate, not present. The best insights will come from the room — people sharing what's actually working (or not) in their companies.
The fear angle is real. Some executives in the room may be worried about AI themselves, not just their teams. Create psychological safety to admit uncertainty.
Keep it practical: If someone says "we should have an AI strategy," push them to be specific. What does that mean on Monday morning? Who does what first?
August 2026
Show-and-tell month. Members come back with actual AI workflows they've built — and we share, critique, celebrate, and steal from each other.
Host: Jeremiah Gutierrez @ UNCS, Fort Lauderdale · Virtual + In-Person
Summer Recap & Rules
Quick look back at the summer: how many sessions happened, how many chapters participated, what themes emerged. Format for lightning demos: 5 minutes each, 1 minute Q&A, keep it moving.
Lightning Demos (6–8 presenters)
Each presenter shares: (1) The problem they had, (2) The AI tool/workflow they built, (3) The result — what changed? Encourage screen shares of actual prompts, outputs, and workflows.
Suggested demo categories:
Open Floor: What Surprised You
Open mic for anyone who didn't present formally. One-minute stories: what AI moment over the summer made you say "wait, it can do that?"
Build on It — Live Remix
Pick the 2–3 most interesting demos and workshop them together. "What if we combined your approach with this tool?" "Could you automate the next step?" Collaborative iteration in real time.
Awards & Wrap
Informal "awards": Most Creative, Best ROI, Best Failure, Most Likely to Change an Industry. Transition to the closing session.
Recruit presenters in advance. Email participants 2–3 weeks before asking "What's the coolest thing you've done with AI this summer?" Line up 6–8 presenters so you don't rely on volunteers day-of.
Enforce the 5-minute limit. Use a visible timer. The energy dies if demos run long. Short and punchy beats thorough and slow.
Celebrate failures. Some of the best learning comes from things that didn't work. Make it safe to share those.
Host: Jeremiah Gutierrez @ UNCS, Fort Lauderdale · Virtual + In-Person
The AI Landscape — Fall 2026
What's changed since June? New tools, new capabilities, new risks. Quick overview of the biggest developments from the summer. What should executives be watching?
Emerging Tools Demo
Live demos of 3–4 tools that have emerged or evolved since the program started. Could include: AI agents, voice interfaces, coding assistants, industry-specific tools, multimodal capabilities. Focus on business applications, not tech novelty.
Panel: What's Your AI Strategy for Q4?
3–4 members share their AI plans for the rest of 2026. What are they investing in? What are they cautious about? Open for questions from the room. Optional: invite an external AI expert or vendor for one perspective.
Regional Roadmap — Do We Continue?
Open discussion: Should this become a year-round program? Quarterly? What format works best? Who wants to lead the next cycle? Poll the room and capture commitments.
Closing Campfire
Each participant shares one sentence: "The most important thing I learned this summer about AI is ___." Close the program with gratitude and next steps.
Research before the session. Spend 30 minutes the week before scanning AI news for the biggest developments. The room will expect you to know what's new.
Guest speaker (optional): If you have a contact who works in AI, invite them for a 15-minute perspective. Keep it conversational, not a sales pitch. Best guests: founders using AI in their business, or technical leaders who can translate for a non-technical room.
The "do we continue" discussion is important. Capture it in writing. If there's interest, assign someone to own the next cycle before the room empties.
// for chapter leaders
This program is designed to be turnkey. Every session guide above includes a minute-by-minute agenda, facilitator notes, exercises, and prompt templates. A chapter learning officer or engaged member can pick up any session and run it with minimal prep.
What we're asking from chapters:
Every session is hybrid, so members from any chapter can join any session virtually. The more chapters participate, the richer the learning experience for everyone.
Questions? Contact Jeremiah Gutierrez directly.