You've got a leadership team that shows up prepared and a quarterly planning rhythm you've protected for years, and you still leave the room knowing some of the hard things went unsaid. The commitments come out fuzzy because everyone's being polite, and the outside facilitator who used to poke the bear either moved on or costs more than the meeting itself.
In this post, I'll walk through how Sarah Shepard, our COO, built what we now call the String Council, an AI advisory board with eight distinct personalities that reads our planning transcripts and pushes back in real time. You'll also get the process she used to build it, and a way to figure out which voices belong on yours.
This post is based on Episode 67 of Revenue Rewired | Build an AI Advisor Council to Kill Your Blind Spots for Good.
If you'd rather listen than read, find the full episode on Apple Podcasts, YouTube, Spotify, or Amazon. It's worth your time.
Sarah opened this episode with a claim she invited anyone to challenge: there's no such thing as saying you have a blind spot anymore. It's an excuse that no longer holds weight. Bold, sure, but the story behind it is what sold me.
We've been running structured quarterly meetings at StringCan for six or seven years now, shaped by operating systems like EOS. When our longtime implementer stepped away, Sarah took over facilitation, which works well for me because I get to stay fully present as the visionary in our duo instead of splitting my brain between contributing and running the room. It worked less well for Sarah, who ended up with half her mind capturing to-dos and reading the room while the other half second-guessed her own contribution. She describes it as noisy, and if you've ever facilitated your own planning session, you know the noise she means.
Then Ryan, our director of service operations, named the real risk. Without an outside facilitator, he worried we'd lose the person who pokes the bear and makes us say the hard things. He was right about that, and rather than hire another facilitator, Sarah built one inside Claude.
Sarah started by feeding Claude our leadership team's personality assessments, CliftonStrengths and 16 Personalities among them, and asked it to identify our weaknesses. Our team runs light in the influence domain, so she asked for a gap filler and named a couple of people she wanted in the room, starting with Jocko Willink and Greg McKeown. From there the council grew to eight personalities, including Brene Brown and Patrick Lencioni, each assigned to the section of our planning agenda where their strengths fit best. The AI came up with the String Council name on its own, and we didn't bother trying to improve on it.
The mechanics are simple. We run a planning session, take the transcript, paste it into the Claude artifact, and hit Convene Council. It returns a consolidated view first, then breaks out feedback advisor by advisor. Because these are real people whose books we've read and whose talks we've watched, their perspective carries a weight that a generic AI response never could.
After the first two sections, everyone wanted to hear from the full council on everything, which none of us planned for. So we dropped the section assignments and just convened the whole council every time.
One thing nobody warned us about: the politics leave the room when the feedback comes from a transcript of your exact words, because nobody can soften a moment after the fact or claim they meant something else. The council flagged that we kept making what it called vague commitments, telling us "I heard a commitment, but I didn't hear a date," and we didn't love being called out for it. By the next round, everyone was showing up with actual dates. Same thing when it said an issue got skipped without resolution; we stopped and asked the room whether anyone actually felt it was resolved.
The moment I keep coming back to involves Brene Brown. I shared something vulnerable during a session, and the team moved right past it, and the council caught it: "Jay shared something really vulnerable, and you guys just blew through it." We had to sit with that one for a minute, because it was true, and it's the kind of moment a room full of kind people misses every time.
Reading the feedback together, live, mattered more than we expected. Sarah said it felt less like a personal attack and more like all of us processing toward the same outcome, with no lag for anyone to leave the meeting misunderstanding something. Each session performed better than the last because the council kept showing us our own patterns.
I've had four or five conversations with other business owners about this in the past week, and they all circle the same question: how do I know who to pick? Sarah's blueprint works for nearly any business. Pull at least one strengths-based assessment for every leadership team member, and spend a couple of minutes writing down where your team shines and where it frustrates you. Then name a few people your team already admires, whose books you've read or whose language you already speak. Don't put strangers on your council, because the value comes from knowing how these people think before you read a word of their feedback.
Then ask the AI the question Sarah asked: whose perspective is still missing from this room? For us, the answer was the voice of the customer, which reshaped who ended up on the council. Expect some pushback along the way, too. When Sarah added Jocko, Claude asked whether she really wanted a personality that intense in the room. She did, because we've read the books and his language is part of our everyday culture, but that check matters. The council only works when it's built for your specific team and your appetite for directness.
We've since built a council for the whole company, which looks more like a board of advisors with HR and legal voices we'd never staff for a planning session, and each department is getting its own, because different problems need different skills in the room.
Q: Do I need Claude specifically to build an AI advisor council?
A: No. We built ours as an artifact in Claude because it's where we already work, but the approach translates to any AI tool that can hold a detailed setup prompt and process a full meeting transcript. The structure and the inputs matter more than the platform.
Q: What do I feed the AI so the feedback isn't generic?
A: Start with your leadership team's personality assessments and a short write-up of your frustrations and strengths, then give it the real transcript of your meeting. Garbage in gets you garbage out, so if you skip the context, you'll get the pat-on-the-back responses people complain about.
Q: How many advisors should be on the council?
A: We landed on eight, each chosen to fill a specific gap in our team's assessment data. Start smaller if you want. Sarah began with two or three names and let the AI recommend the rest, including voices she'd never thought to put in the room.
Q: Won't the AI just agree with everything we say?
A: Only if you let it. Ask for a challenger mindset explicitly and ground each advisor in a real person's published thinking, and it'll call out vague commitments and skipped issues you'd never catch yourselves.
Q: Does this replace our facilitator entirely?
A: Not quite. Someone still coordinates the room and manages the agenda, but the council carries the outside perspective and the willingness to say hard things, and it never forgets what was said. That frees your facilitator to actually participate.
At StringCan, we work as a growth partner for our clients, which means we test tools like this on ourselves before we ever bring them into client work. The String Council started as a fix for one missing facilitator and turned into a system we now use across the company, and it reflects the same philosophy we bring to marketing: give the tools real context and demand pushback instead of settling for generic answers.
If you want to hear the full story, including the moments where the council made us squirm, listen to Episode 67 here. And if you're ready to talk about what a growth partner could do for your revenue, connect with us at stringcaninteractive.com. We'd love to hear what your council calls out first.