Right before I recorded this, I spent the whole morning inside Claude working through my next big decision. And the entire time, I could not shake the feeling that it was just agreeing with me. That is the exact problem Sandra Booker solved, and she solved it in a way I have not stopped thinking about since. Sandra is a fractional COO for online service providers, and she built her own AI advisory board inside Claude. Six board members, each modeled after a real business mind, each with their own expertise, their own personality, and their own job to do when she is facing a big call. One of them exists to remind her that she actually has to sell things and make money. Another exists purely to challenge her so the AI stops telling her what she wants to hear.
I recorded this session live at my AI Exposed summit, and we sat in on one of her real board meetings while she worked through whether to relaunch one of her programs. It is a little less polished than my usual episodes, but the content was too good to keep in that room.
In Today’s Episode We Discuss:
- Why AI keeps telling you what you want to hear
- Meet Sandra’s board members
- How to decide who belongs on your board
- Why every advisor is its own Claude Skill
- Where the decisions actually go
- How she built the whole board in one conversation
- Getting the good side of a boardroom without the toxic part
- Why an AI board beats asking real people
- Whether this helps or hurts your critical thinking
Resources Mentioned:
Follow Sandra Booker on Instagram, where she shares more about her AI advisory board work under the handle Sidekick COO.
Learn more about Scale Society, the group program Sandra and Monica walk through relaunching live during the board meeting.
Explore more from Sandra at Sidekick COO, her home for fractional COO services and resources for online service providers.
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