Workshop for Executive Communities
Build Your Personal AI Guardrails
A workshop for members who want to stop guessing and start deciding about AI.
Most of your members are using AI and making it up as they go. They hesitate before pasting things into ChatGPT, second-guess what’s safe to share, and watch peers move faster while they pause. This workshop replaces that hesitation with a framework they can use the same day.
Delivered at Chief and The Upside. Available virtually or in-person.
The premise
Enterprise companies have AI policies. Individual operators have vibes.
Every member of your community is already using AI. Most are making it up as they go. They hesitate before pasting a client document into ChatGPT, second-guess what’s okay to share, and watch peers move faster while they pause.
This workshop gives your members a framework so they can move forward on their own terms. They leave with a personal AI guardrails one-pager they can reference daily and share with clients if asked.
What members walk away with
A finished, one-page document. Not a notebook full of ideas.
Every member leaves with a version-one Personal AI Guardrails document, customized to their own business. It covers:
- Their risk profile as an operator and the risk profile of their clients. A 2x2 that tells them which AI moves are aligned, which require caution, and where they have room to stretch.
- A green / yellow / red sort of where AI belongs in their actual work, broken down by task and data type.
- A 5-step safety check they can apply to any new AI tool, plus a worked example using two real-world products.
- A policy statement they can say out loud when a client asks “do you use AI?”
- A review cadence so the document stays current as tools change.
The artifact doubles as a personal decision filter and a client-facing policy. It’s the thing they save and look at again.
How the session runs
Four parts and a pressure-test
Find your quadrant
Members score themselves and their clients on a 1 to 7 risk scale and land in one of four operating zones. This becomes the lens for everything else.
Color-sort the work
Same task, different data, different color. Members walk away knowing exactly which categories of work are green, yellow, and red for them specifically.
Evaluate one tool
A 5-step safety check applied to a tool they use today, modeled live with a comparison between two real products. Meeting transcribers are the highest-leak category, so we start there.
Write the statement
Members pull their answers together into a working sentence they could read to a client tomorrow. A few share out loud.
Four scenarios. Three concrete actions.
Members leave with a written commitment, not just a notebook full of ideas.
Who it’s for
The workshop holds for a mixed room
Which is a real strength for community programming.
Solo operators
Founders, fractional executives, and consultants who run their own businesses and need a personal anchor.
Corporate executives
Working under (or building) a company AI policy and wanting a personal stance to bring back to their teams.
Members in regulated industries
Healthcare, finance, legal, education. Specific data obligations, and a need for a defensible position.
The women-in-business lens runs through every section. The women in your community are often the most thoughtful and the most cautious about AI. This framework moves them from cautious-and-paused to cautious-and-acting.
What members said
From the room
“She was riveted, and she learned a lot.”Chief staff member, in-person workshop, May 2026
“This was invaluable.”Chief member, in-person workshop, May 2026
“I hope Amanda does more workshops.”Chief member, in-person workshop, May 2026
Delivered at The Upside (April 2026) and Chief (May 2026).
Format options
Built to fit your programming calendar
About Amanda
Who’s facilitating
Amanda Worsfold is an AI strategy and implementation consultant based in San Francisco. Twenty years in tech and people operations, three years building AI workflows for solo operators and small firms. She helps clients move from AI curiosity to AI competence: building policies, training teams, and designing practical AI workflows they actually use.
She holds a Stanford Human-Centered AI certificate and has worked with Fortune 500 companies. She has facilitated Build Your Personal AI Guardrails for The Upside (April 2026) and Chief (May 2026). Both rooms had a mix of corporate executives, founders, and fractional leaders.
Frequently asked
What community programmers ask before booking
How long is the workshop and what formats do you offer?
Three lengths: 45 minutes as a briefing, 60 minutes as the standard, and 90 minutes for the full workshop with pressure-test scenarios and pair share. The 60 and 90 minute formats are where members complete the full one-pager. The 45 minute briefing introduces the framework and seeds the work.
Will this work for a virtual audience?
Yes. The workbook is the main activity and individual reflection drives the session, so virtual works as well as in-person. For virtual sessions I run the live evaluation in a shared screen and use breakout rooms for pair share at the 90 minute length.
Our members are at very different stages of AI adoption. Will the workshop hold?
This is what the workshop is built for. Because members work on their own business and their own data, the activities scale with experience. A first-time AI user finishes the one-pager. A heavy AI user uses the same activities to tighten and defend choices they’ve already made.
Do you handle the materials or do we?
I handle them. Bookings include the live session, member workbooks (printed or digital), the 5-step safety check reference card, and a post-event follow-up email sent to attendees with all materials. You handle room setup, member communications, and AV. I send a tech check list before in-person events.
What does pricing look like?
Custom quote based on length, format, and group size. The discovery call is the next step. Most community bookings include the live session, all member materials, and the post-event follow-up. Multi-session series and chapter rollouts are quoted separately.
How far in advance do you book?
Six weeks is comfortable for member communications and tailoring. Four weeks is workable. Tighter than that, get in touch and we can talk through options.
Can you customize the workshop for our specific community?
Yes. The framework is the spine, and I tailor examples and scenarios to your community’s industries, member archetypes, and any specific concerns you’ve heard from members. Customization is included in the quote and we scope it on the discovery call.
Bring this to your community.
Twenty minutes to talk through fit, format, and dates.
Book a Discovery CallPrefer email? amanda@amandaworsfold.com
Are you an individual executive interested in this content? Take a look at Executive Setup.