Nobody in their right mind invites Jocko Willink to sit in on a quarterly planning meeting. That's like asking a drill sergeant to supervise your morning workout. Sure, you'll come out stronger. You'll also hate every minute of it.
I built him a seat at the table anyway. Him and about seven others.
Before our Q3 leadership working session I spent some time assembling a panel of AI advisors modeled after the thinkers who've shaped how I lead. I call it the StringCouncil, and its job was to help me facilitate by filling the gaps that exist on my team. Jocko was there for ownership and accountability. Brené Brown for the hard truths nobody wants to be the one to say. Patrick Lencioni to ask whether we'd solved the real problem or just the polite version of it. Donald Miller for clarity. Blair Enns to push on whether we're actually leading our clients or quietly taking their orders. Greg McKeown to ask what's essential and what we're saying no to. David C. Baker to keep us honest about whether we're profitable or just busy. And an EOS Implementer lens to check whether a "rock" was a real rock, with one owner and a real date, or just a to-do wearing a costume.
I built the council using Claude. I uploaded our team's personality assessments so it knew exactly where we tend to slip, and then during the meeting I'd pull the transcript, point the council at it, and click Convene. Let's just say Jocko had thoughts.
Here's the part I didn't expect.
Each council member named what we'd actually done and put it on the screen where everyone could see it. At one point someone shared something vulnerable and the room did what rooms do when the agenda is full: we moved right past it, nobody wanting to be the person who slows things down. The StringCouncil flagged it. I'm not sure I would have. And because the observation came from our own words rather than from a colleague who might be having a bad day or carrying an agenda, nobody got defensive. There was no social math about whether this was the right moment to bring it up. The AI didn't care about the politics of the room. It just said the thing.
It did the same with our commitments. Someone said they'd "handle" something, which sounds like accountability right up until you notice there's no due date and no real definition of done. The council noticed, out loud, on the screen, in front of everybody. And the next stretch of the meeting got sharper because of it. People started saying things with more precision. Owners and dates showed up without anyone having to chase them.
I've run a lot of meetings. Quarterly plannings, leadership sessions, all-day off-sites where you walk in with a tight agenda and a lot of hope. If I'm being straight with you, facilitating is its own kind of disappearing act. You're in the room physically, but you're also hovering somewhere above it, tracking who hasn't spoken yet, feeling the energy shift when something lands wrong, holding a dozen threads at once while trying to look like you're just listening. You're present the way a stage manager is present during a show. Technically there. Not really in it.
I'd accepted that as the cost of running a meeting well, and I didn't even notice I'd accepted it until this one felt different.
Because the StringCouncil was doing the watching, I got to think out loud for the first time in a long time. I caught myself reacting to what people said instead of cataloguing it for later. I had opinions in the room instead of saving them for the drive home when I'd finally have space to process what happened. I followed a thread because it interested me, not because I was managing the clock. If you've spent years in the facilitator seat, you know exactly what I mean. There's a version of you that shows up to these meetings and a version that stays in the car. This time I brought both.
And it changed what I gave the room. I wasn't suddenly smarter or better prepared. I just had bandwidth I don't usually have, so I came with more to offer. The gaps were getting caught. The commitments were getting tracked. The uncomfortable thing was getting said by something that doesn't have to go to lunch with us afterward. That freed me up to lead in the room instead of being the person making sure the room worked. I built the council because I wanted sharper outcomes and fewer loose ends. What I didn't see coming was getting my own participation back.
We talk about blind spots like they're just part of being human, like not seeing something is inevitable, and we should all make our peace with it. But you can upload your team's personality profiles, point an AI at your meeting transcript, and get called out by Jocko Willink at ten in the morning, whether you're ready for it or not. The information is sitting right there. The perspectives are available. The only thing between you and a clearer picture of what's happening in your own room is whether you're willing to look.
Would I have invited the real Jocko? Probably not. It would have been too much. But the version I built showed up, did the hard thing, and handed the room back to us better than it found it. So now I'm sitting with a different question, and maybe you should too: what's actually going on in your meetings that nobody's willing to name, and what would change if something finally did?
Sarah Shepard is the COO of StringCan Interactive. She writes the String By String newsletter on LinkedIn most weeks. If this one resonated, it's worth subscribing.