Daily Prompt Pack: Hiring Your First 3 – The sequencing questions that stop you from hiring the wrong person twice

Most founders hire their first three people in the order that feels urgent, then spend a year cleaning up the org chart. I run this exact sequence in Notion before I post a single job. Here are the three prompts I use, in order, on the topic of hiring your first three.

[Claude]

[Claude] I’m a solo founder doing $18k MRR, shipping features, support, and sales myself. Interview me one question at a time about where my week actually breaks, then output a 3-role ladder table: role, what it permanently removes from my plate, monthly cost, hire order. Flag any role I could replace with a $200/mo tool instead.

[ChatGPT]

[ChatGPT] Write a one-page interview scorecard for a first engineer at a 4-person seed startup. Four competencies, one behavioral question each, and a 1-5 anchored rubric per level where 3 is hire and 5 is ‘explain it to a customer.’ Add a red-flag row for candidates who can only describe work as a team effort. Output as a table I can print.

[Cursor]

[Cursor] Generate a reference-call script for my first hire’s final-stage references. Five questions that surface the candidate’s real failure mode, plus a follow-up probe for each. Skip soft questions like strengths. Output as a markdown checklist with a blank field for the verbatim quote I should record after each answer.

Full archive at aicofounderstack.com/tag/prompt-pack.