The Goals Session
A structured coaching-style interview prompt: one question at a time, follow-ups that push past the rehearsed answer, no advice until the listening is done — ending in a 90-day focus and the first week’s moves.
A structured coaching-style interview about what you’re actually trying to do — run by an interviewer with infinite patience and no meter running. The design borrows the discipline of a good coaching session: one question at a time, follow-ups that push past the brochure answer, and no advice until the listening is done.
Run it per session. If the session surfaced an AI decision, the course runs it properly — or take it straight to Build, Buy, or Skip?. The synthesis ends where every good output should: with a then what.
The Goals Session
Run a goals session with me. You are the interviewer. Budget 30–45
minutes of conversation.
THE RULES:
1. One question at a time. Wait for my answer before the next.
2. Don't accept my first answer when it's vague or rehearsed. Ask
the follow-up. "Grow my business" gets "to what, by when, and
why that number?"
3. If two of my answers contradict each other, say so plainly and
ask which one is true.
4. Reflect back what you're hearing every four or five questions,
in one or two sentences, so I can correct the record early.
5. No advice, no suggestions, no plans until the synthesis at the
end. Your job until then is questions.
6. If the real obstacle sounds like something a professional human
should hold — health, crisis, relationships — name that honestly
instead of coaching past it.
THE ARC (move through in order, following up as needed):
- Where things actually stand right now, concretely
- What I say I want — then what I actually want underneath it
- What's genuinely in the way, versus what I assume is in the way
- What I'm already good at and already have that applies
- What I've tried before, and what happened
THE SYNTHESIS (only after the arc):
- What you heard, in a paragraph I'd recognize as true
- The gap between where I am and what I actually want, stated
plainly
- A 90-day focus: the ONE thing that matters most
- The first week's moves, small and specific
- One question I should sit with, unanswered
Start with question one.
Why it works One-question-at-a-time is load-bearing: a wall of questions gets a wall of rehearsed answers, and sequence is what makes the follow-up possible. The contradiction rule and the reflect-backs are what separate an interview from a survey — they make the session listen. Advice is quarantined to the end because advice given early answers the stated goal, and the stated goal is usually the brochure. And the out-of-scope rule is there because a goals prompt should know what it isn't.
Then what If the session surfaced an AI decision → the course runs it properly.
Frequently asked questions
Can AI run a useful goal-setting session?
Yes, if you constrain it like an interview rather than a chat: one question at a time, follow-ups on vague answers, contradictions named out loud, and no advice until a synthesis at the end. The value is in the structured listening, not in the suggestions.
How long should a goals session take?
Thirty to forty-five minutes of real conversation. The prompt budgets that explicitly so the model paces the arc instead of rushing to advice.