Day 1 – Breakout Session 2 – 11:15-11:45 AM
Room: Fixxology
More Tools Won’t Save a Bad Decision. Better Thinking Will.
Seth Deming · AI Leverage Academy · RizeCon 2026 · Pocatello
A few years ago, Seth Deming hired someone he knew he shouldn’t. He saw the red flags. He checked references, ran the interviews, did everything right — and then justified the warning signs away. Three months later, it hadn’t worked out. He calls it the decision that showed him exactly what he wishes he’d had: a thinking partner without an agenda, without any stake in the outcome, capable of surfacing what he was rationalizing past. That’s what his RizeCon session was about — not AI as a tool for automation, but AI as a structured thinking partner for the decisions that keep business owners up at night.
The session ended with a live demonstration where a performance coach in the audience worked through a real, unresolved hiring decision with Claude, in real time, in front of the room.
What he covered
Leaders don’t make bad decisions. They make decisions without seeing around the corners. Seth’s opening reframe: the failure mode isn’t ignorance or bad judgment. It’s that most leaders make decisions with incomplete situational awareness — focused on what they can see, not on what they can’t. More tools don’t fix that. Better thinking does. That’s the problem AI, used correctly, is actually well-suited to help solve.
The premortem: assume the decision fails, then work backwards. Most organizations run postmortems — looking back after something goes wrong to figure out what happened. Seth introduced the premortem, which flips the sequence entirely. Before committing to a decision, assume it fails in 12 months. Then ask: what are the main reasons it would have failed? Working backwards from a hypothetical failure forces you to surface assumptions you’re not yet interrogating, reasons you’ve been suppressing, and systemic risks you haven’t had to name. Seth’s argument: if you’ve already decided but haven’t yet committed, the premortem is the exact right moment to pause.
AI as a thought partner — not a search engine. Seth draws a sharp distinction between using AI to retrieve information and using AI to think. Most people do the former. They ask AI to generate outputs. What Seth teaches in AI Leverage Academy is the latter: structured conversations where AI asks clarifying questions, surfaces what you’re not seeing, and holds the frame of the problem while you do the actual thinking. AI doesn’t have an agenda. It has no stake in whether Tyler’s marketer works out. That neutrality is the feature — it asks the questions a trusted advisor would ask without the social dynamics, the relationship cost, or the fear of being wrong.
The live demo: Tyler’s marketer decision. A performance coach in the audience named Tyler volunteered a real, live decision: he’d hired a marketer a few weeks prior, wasn’t seeing results, and couldn’t decide whether to continue, retrain, or let the person go. Seth walked him through a premortem using Claude as the thinking partner, asking Tyler clarifying questions to build context and then feeding them into a live Claude conversation. Claude’s first move was to ask what “performing well” actually meant — was Tyler measuring leads, brand awareness, conversion, or revenue? If the marketer doesn’t know the real success metric, they’re probably optimizing for the wrong thing. From there, it asked about baseline lead flow before the marketer started, whether the marketer understood the conversion funnel (150 people to a challenge, 50 to an offer, 10-15% to a $1,000 product, 2% to a $28,000 program), and whether Tyler had given the marketer the raw materials — content, case studies, testimonials — to actually build something from. By the end, Tyler had clarity he didn’t have going in: his sales funnel worked, his primary lead source was JV partners, and the real question wasn’t whether to hire in-house versus outsource — it was whether anyone he hired could build organic lead flow that didn’t depend entirely on partner relationships.
If you can articulate the problem clearly, you’ve already solved half of it. Seth’s meta-observation from the demo: the act of explaining a decision in enough depth for AI to understand it forces a level of clarity that most business owners skip. The AI response is secondary. The structured articulation — defining the KPI, naming the constraints, acknowledging what hasn’t worked — is where the insight starts. AI gives you the space to think. Clarity is built, not downloaded.
The master prompt: give AI the boundaries first. For anyone worried about AI hallucinating, gaslighting, or optimizing for the wrong outcome, Seth’s answer is the master prompt — a three-page document that tells the AI your role, the context you’re working in, the expected output format, and explicit instructions to challenge your assumptions rather than confirm them. He updates his every couple of months and builds project-specific versions for major initiatives. Key instruction he puts in every master prompt: “Tell me what I need to hear, not what I want to hear.” Two important additions from the audience: a master prompt is the DNA of how you want AI to operate — and if you’ve spent six months using AI without one, you may have trained it bad habits. When AI gets something wrong, the productive move is to argue the correction hard until the record is set straight, not to dismiss the tool.
What attendees got
Seth runs AI Leverage Academy, where he works with business owners using real decisions — not case studies or hypotheticals — and solves them together in live sessions. The premortem framework, the master prompt structure, and the thinking-partner approach to AI prompting are the core of what he teaches. Attendees who want the full version were invited to connect with him after the session.
One story that landed
An attendee shared, unprompted, that she’d built a master prompt that turned AI into a virtual clone of herself — loaded with her background, her architectural firm’s design criteria, and her decision-making process. She described it as finally doing what she’d always wished she could: have 10 more versions of herself. Her business had grown significantly in the two to three months since. Seth didn’t skip past the testimonial — he folded it into the session’s central argument. Clarity plus context equals leverage. The more precisely you give AI the parameters to work from, the more it amplifies you rather than producing generic output. The prompt is your artistic expression. The more specific, the more it sounds like you.
“AI won’t give you all the answers. It will give you the space to think.” — Seth Deming
“Clarity is built, it’s not downloaded.” — Seth Deming
About the speaker
Seth Deming is the founder of AI Leverage Academy, where he trains business owners to use AI as a structured thinking partner — not as a productivity hack, but as a mechanism for better decisions. He spent 20 years building a company in the HR space before turning his attention to how AI changes the way leaders think and decide. His book was releasing on his 50th birthday, 22 days after RizeCon. He uses Claude as his primary thinking-partner tool and teaches the master prompt framework as foundational to any serious AI practice.