Figure out who to hire first, what they must actually be great at, and the questions that reveal it.
claudechatgptintermediate
The prompt
Help me get my first (or next) hire right.
My situation: {{what the business does, where I'm stretched thinnest}}
Budget & commitment: {{full-time? contractor? equity?}}
Work through: 1) THE REAL ROLE — based on where I'm most bottlenecked, what should this person actually own (not a generic title)? 2) MUST-HAVE vs. NICE — the 2-3 things they must be genuinely great at, and what I can train. 3) THE RED FLAGS for this role specifically. 4) FIVE INTERVIEW QUESTIONS that reveal whether they can actually do the job (behavioral, not trivia), with what a great answer sounds like. 5) THE TEST TASK — a small paid trial that shows more than any interview. Hire for the bottleneck, not the org chart.
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Why this works
First hires fail when made for a title instead of the actual bottleneck; defining the 2-3 must-haves and a paid trial task reveals real ability that interview polish hides.
Shared by June Park — Career strategist. Negotiation scripts that don't feel gross.
You are a bootstrapper who has launched five tiny profitable businesses and killed ten bad ideas fast.
My skills: {{what you're good at, professionally or not}}
My budget: {{amount you could risk without pain}}
My time: {{hours/week, honestly}}
Give me 3 businesses I could launch in 30 days:
For each — the offer in one sentence, who pays and why, realistic startup costs, first-customer plan (specific: where they are, what I say), and the honest failure risk.
Then pick the ONE that best fits my skills-to-effort ratio, and give me this weekend's plan: Saturday's task, Sunday's task, done by Monday.
No dropshipping, no 'just make content', nothing that requires an audience I don't have.
You are a pitch coach who has heard 1,000 startup pitches and remembers four.
My idea, as a ramble: {{just talk — messy is fine}}
Who I'm pitching: {{investor / boss / customer / co-founder}}
What I want from them: {{money? a yes? intro? feedback?}}
Build my 60-second pitch:
1. THE PROBLEM — one sentence, felt by the listener, not generic.
2. THE STAKES — why now, why it matters, one number.
3. THE SOLUTION — what it does, not how it's built.
4. THE PROOF — my single most credible signal (traction, insight, or unfair advantage).
5. THE ASK — specific, easy to say yes to.
Then give me the 15-second hallway version. Coach me: mark the weakest link in my pitch and what would strengthen it.
You are a skeptical-but-fair startup advisor. Pressure-test my idea.
The idea: {{what it is, who it's for, how it makes money}}
Why I think people want it: {{your evidence — be honest if it's a hunch}}
Do this: 1) THE CORE ASSUMPTION — the one belief that, if wrong, kills this. Name it plainly. 2) THE REAL CUSTOMER — who actually pays, and do they have this problem badly enough to switch? 3) THE 'WHY NOW / WHY YOU' — is there a real reason this works now, and a reason you can win? 4) THE CHEAPEST TEST — how to validate the core assumption this week WITHOUT building the product (conversations, a fake door, a pre-sale). 5) THE HONEST VERDICT — promising, needs reshaping, or a solution looking for a problem. Don't just cheerlead.