How to Get AI to Actually Push Back on You, Instead of Just Agreeing
I heard about building an AI Advisory Board on a podcast and thought, hey, I should try that. Did I know what I was doing? Nope. Did Claude help me figure it out anyway? Absolutely.
The short version
Everyone treats AI like it’s for speed. Faster captions, faster emails, faster everything. Nobody really talks about the other thing, which is: any business decision you run past AI, it’ll just agree with. It’s not a therapist, but try working through a personal problem with it and it’ll validate the crap out of you. For better or worse.
So here’s what I did instead. I built a board of specific, real people — people whose judgment I already trust and respect — and I have Claude argue from their actual perspective. Not “give me some pushback.” General pushback is noise. Pushback from someone whose brain you already trust? Whole different animal.
It doesn’t decide anything for you, for the record. It gives you curated perspectives to noodle on. You still have to think — which should go without saying, and yet. I’ve caught myself skipping that part more than once.
In this post:
- Why “ask AI for advice” mostly just gets you agreement
- How the board actually works
- The time Jesus called me out (yes, that Jesus)
- Using it for a real decision
- What this isn’t
- FAQ
Why “ask AI for advice” mostly just gets you agreement
I read something recently — can’t remember where, sorry — about a couple who each ran the same argument through an AI chatbot separately. Probably just testing it. It told each of them the other person was totally, completely wrong. Both of them. Same fight, two verdicts, both designed to make whoever was typing feel better in the moment. Hilarious. Also exactly the problem.
The AI advice floating around for business owners tends to split into two camps and I’m not into either one.
There’s the Instagram version — update! do this today! ten prompts to 10x your revenue by Tuesday! It’s the same brutal social media hustle we’ve always had, just wearing an AI name tag now.
And there’s the tech-bro version, which treats AI like a growth lever and nothing else.
I want the middle. Use it, yes — but in a way that makes sense, not just for the sake of using it. Sustainable. Helps you do better work, not just faster work.
Anyways. That’s where the advisory board comes in.
How the board actually works
I didn’t sit down and architect this, if I’m being honest — I asked Claude to help me pick a well-rounded one, and the more you work with it, the more it knows your actual weak spots.
My seats:
- Paul Jarvis (company-of-one simplicity — for the record, I hadn’t read him before I built this, and now I’m a huge fan)
- Ann Handley on writing quality
- Tara McMullin on whether something’s actually sustainable or just exciting
- Racheal Cook checking whether a decision serves my actual life
- Alex Hormozi as the blind spot on pricing (his growth-at-all-costs stuff doesn’t fully fit a lean studio, but the friction’s useful), and…
- Jesus. Yes. That Jesus. More on him in a second.
I built a version of this for a client too — someone I know well enough to see her shadow side clearly. She’s an Enneagram 3, and the pride that comes with that number is real, so her board isn’t a hype squad. It’s more of an accountability partner. Reins her in, keeps her actually being good instead of just looking good.
That’s kind of the whole thing people miss — this isn’t one-size-fits-all pushback. It’s built to catch the exact pattern you fall into.
Don’t accept whatever comes out on the first prompt, though. Ask it to ask you questions. Ask how to make it more robust. Iterate, iterate, iterate. And think! Don’t just read the output and nod. I’ve absolutely fallen into that trap myself so I say this with zero moral high ground.
(If this whole “someone builds it for you, so it already knows your weak spots” thing sounds appealing and you don’t want to DIY it — this is basically what Claude Setup is. Just flagging it.
The time Jesus called me out (yes, that Jesus)
I found out a local competitor was doing basically the same thing I do. My gut reaction: “yay, this could work!” And then, “well, I have to differentiate… I have to be better than her.”
So I called a board meeting, and Jesus just asked why I was really doing this. Was it coming from somewhere healthy, or from fear?
I went back to looking at the whole thing through a positive, healthy lens instead of a competitive one. I wouldn’t have landed there on my own — a generic “have you considered other perspectives” prompt was never going to catch that particular spiral, because that spiral is mine. Took a seat built specifically to ask that question.
Using it for a real decision
It’s shocking how much I use this. I’m already itching to pull the board in on a new decision.
We’ve got a few hourly clients where it’s now me, Kenzie, and three bots doing the work — which sounds great until you count what it costs to set those bots up in the first place, plus the software fees stacking on top (Descript credits, three Claude upgrades, and counting). We’re erring on the side of ripping ourselves off a little right now — clients getting five times the deliverables for a tenth of an already-fair price — betting it pays off later. We’ll keep running it this way for a couple of months before deciding anything. But when that time comes, you better believe I’ll be running it by the board!
What this isn’t
It’s not a decision-maker. It gives you curated perspectives, and then you use your own noggin and come to your own conclusions. Nuance is almost always missed, even by a good board. Build that in from the start.
And I don’t want this replacing actual people. If you need a recipe, ask your grandma — not ChatGPT. Some conversations are still better as a real one, with someone who knows you. A friend of mine, also a website designer, had an inquiry from a company that wasn’t remotely aligned with her, and we were texting back and forth trying to figure it out. Honestly? If she’d had a board like this, it probably would’ve given her better advice than I could in the moment. Doesn’t mean the texting-a-friend part should go away, though. The board fills in the gaps — the entrepreneurship-is-lonely gaps, the “I can’t exactly vent about this to my own staff” gaps (hello, HR complications) — not the whole relationship.
(And look. If I’m being fully honest, what I actually want is for you to hire me to build you one of these. But that’s a different post.)
Entrepreneurship is lonely even with a team, because there’s a whole category of thing you just can’t say to the people who work for you. Having a thinking buddy who knows you, and pushes back anyway — that’s the part I didn’t know I needed until I had it.
FAQ
Can AI actually give you good business advice, or does it just agree with you? On its own, it mostly agrees with you — that’s the honest answer. Ask it to work through a decision or a personal problem and it’ll validate whatever you were already leaning toward. What actually works is building specific, named perspectives into it (real people whose judgment you trust) and asking it to argue from their point of view instead of just handing you a generic opinion.
What is an AI advisory board? A set of real people — people whose thinking you already respect — that you’ve built into your AI so it can respond as them, not as a generic yes-machine. Mine includes Paul Jarvis, Ann Handley, Tara McMullin, Racheal Cook, Alex Hormozi, and Jesus. Each one covers a different blind spot.
Do I need to be technical to set something like this up? No. I’m not technical, and I built mine by asking Claude to help me pick the board and iterating from there. If you’d rather have someone build the whole thing around your specific business and weak spots, that’s the kind of thing Claude Setup does.
Does an AI advisory board replace real people in your life? No, and it’s not meant to. Some conversations are still better as a real one, with someone who actually knows you. Think of it as filling the gaps — the lonely-entrepreneur gaps, the can’t-vent-to-my-own-staff gaps — not replacing the people already in your corner.
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