“I’m considering hiring a [role] for my [stage] startup. Before I post the job, help me validate whether this is the right decision. The problem I’m trying to solve: [describe]. What I’ve tried already: [describe]. My current team structure: [describe]. Monthly burn and runway: [describe]. Challenge me on this hire: (1) Could this outcome be achieved through a different solution — automation, a contractor, a process change, or better leverage from existing team? (2) What’s the opportunity cost — what else could we do with this budget in the next 6 months? (3) What does success look like for this role at 90 days — specific and measurable? (4) If I don’t make this hire, what’s the realistic worst-case outcome? Be direct — I don’t want a hire justified, I want the decision validated.”

“Write a job description for [role] at my [stage] startup. What this person will actually own: [list 3–4 outcomes, not activities]. What the first 90 days look like: [specific deliverables]. Real requirements: [4–5 genuine must-haves — no padding]. What makes someone a bad fit: [3 honest signals — include as a ‘You might not be the right fit if’ section]. Why this role matters right now: [one sentence]. Compensation: [range + equity]. Write it in a founder’s voice — direct, specific, no corporate language, under 400 words. The JD should make the right person excited and make the wrong person self-select out.”

“Write a LinkedIn outreach message to a passive candidate for my [role] opening. What I know about this specific person: [describe their current role, company, any work of theirs you’ve seen]. Why I think they’re a fit: [describe specifically — not just ‘your experience is relevant’]. What makes this role interesting: [the problem they’d solve, the impact, the stage]. The message should: be under 100 words, reference something specific about them that isn’t just their title, explain why I’m reaching out to them specifically, and make the ask low-pressure. Include 2 versions — one more formal, one more conversational — and a subject line for both.”

“Screen this CV for my [role] opening. My real requirements: [list your 4–5 genuine must-haves]. Here is the CV: [paste]. Tell me: (1) The 3 strongest signals that this person could do this job well, (2) The 2–3 gaps or red flags I should probe in a screening call, (3) The 3 specific questions I should ask in a 20-minute screening call based on what I see here, (4) Your honest recommendation — is this person worth 20 minutes of my time? Explain your reasoning. Don’t be polite — a vague assessment that fails to distinguish strong from weak candidates is useless to me.”

“Build a structured interview guide for [role] at my [stage] startup. The 3 most important competencies for this role: [list them]. For each competency: (1) Write 2 behavioural interview questions (starting with ‘Tell me about a time…’), (2) Describe what a strong answer looks like vs a weak answer, (3) Provide a 1–3 rating scale with specific descriptions for each score. Also include: the one situational question that tests how they’d handle a challenge specific to this role at my stage, and the closing question that best reveals whether someone will thrive in an early-stage environment. Format it as a live interview guide I can use in the room.”

“Design a take-home assessment for [role] at my [stage] startup. The real work they’d be doing in their first 60 days: [describe]. The assessment should: take 2–4 hours, involve realistic work not a hypothetical puzzle, be completable without knowledge of our specific codebase or internal data, and produce output I can evaluate meaningfully. Include: (1) The task description as I’d send it to the candidate — specific, interesting, and respectful of their time, (2) The rubric I’ll use to score submissions — 4–5 criteria with descriptions of strong vs weak work for each, (3) The follow-up questions I’ll ask in the debrief call. Note: should I offer to pay candidates for this? Give me your honest view based on the role level and market norms.”

“Prepare me for a reference call with [reference’s relationship to candidate — e.g. former manager, peer, direct report] for my [role] candidate. What I most want to learn: [describe your specific concerns or gaps from the interview process]. Write: (1) The 5 questions I should ask in this specific reference call — tailored to the relationship and my concerns, not generic reference questions, (2) The follow-up probes if the reference gives a cautious or positive-but-vague answer, (3) The one question that most reliably produces honest information about a candidate’s weaknesses, (4) What I should be listening for in how the reference speaks — not just what they say. The goal is to hear what the reference is choosing not to say as clearly as what they are saying.”

“Write the personal message I’ll send alongside the formal offer letter to [candidate name] for [role]. What I know about why they’re interested: [describe — what excited them in the process, what they care about]. What I want them to feel when they read this: [describe — confident in the decision, excited about the opportunity, clear on why we want them specifically]. The message should: be from the founder personally, reference something specific from our conversations that shows I was listening, articulate why we want them specifically (not generic enthusiasm), and make it easy to say yes while leaving space to ask questions. Under 200 words, warm but not effusive.”