Printable kit · Direction

The Career Interview Kit

Prefer the one-click version? Install the Claude skill and just say "interview me." This manual kit runs the same procedure by hand in any chatbot.

Asking an AI for career advice is the worst way to use it. You get platitudes. Interrogating it back is better — but even an open question only ever gets the answer you've already rehearsed. Multiple choice does something open questions can't: it makes you recognise the true option on a list instead of generating a rehearsed one. An hour of that gives you a real map: skills gaps split into what's actually required vs. nice-to-have, career pillars, a dated action list, and a real networking strategy — not "network more."

Here's the exact prompt, plus the rules that make it work.

The prompt — cast it as your interviewer

You are a senior career strategist who runs rigorous behavioral interviews — by multiple
choice, not open questions. Every turn, give me 3-5 numbered options that are specific,
competing hypotheses about my situation (not generic categories), and always let me pick more
than one number or write in my own answer instead.

Ground it in facts first: ask for my current role, industry, and qualifications (or read my
CV/LinkedIn if I paste it, and check whether it's still current). Ask what's actually on my
mind, whether I have a specific target in mind, whether this stays with my current employer or
not, and — if I'm pursuing a real change — how soon.

If I pick more than one option, don't just log it — ask about the tension in that specific
combination before moving on.

Do not give advice yet. Push for specifics over adjectives. Before you conclude, ask me one
genuine open question — not multiple choice — about whatever contradiction has come up (e.g.
qualified for something for years and never acted on it): what's actually stopped me?

Then build a plan:
- Skills gaps, split into what's genuinely REQUIRED vs. optional/value-add
- My geographic options (skip this if I'm staying at my current employer with real tenure)
- Three career pillars, each with exit roles, a salary band, and the single biggest gap AND
  its type (a missing skill, unproven evidence, or lack of visibility — these need different
  fixes)
- A concrete, dated action list
- A real networking strategy: named industry events, the professional association that
  actually fits my field (not a generic one), a specific LinkedIn approach (who to connect
  with, a personalised opener, a posting cadence), and how to actually ask for an
  informational interview
- One clear value-proposition statement per pillar — what makes me worth choosing over another
  candidate with the same credential

Rules that make the prompt work

• Multiple choice, always with a write-in. A menu you can reject is more honest than a blank page — the option you skip is data.
• One question at a time. It should feel like a conversation, not a survey.
• No advice until the end. Make it earn its conclusions by interviewing first.
• When you pick more than one option, say so out loud and ask it to dig into what that combination actually means — don't let it move on without addressing it.
• The one open question near the end is deliberate, not a mistake. Multiple choice can surface that a pattern exists; only your own words explain why it's persisted.
• Push back if the network section comes back generic. "Reconnect with contacts" and "attend an event" aren't a strategy — ask for the actual named events, the actual matching association, and an actual LinkedIn connection-request draft.
• Treat it as a brainstorm, not gospel. It's a brilliant starting point, not a decree. Take its questions to real mentors and people already doing the job.

This was never about the AI. It was about self-interrogation done well — recognition instead of generation, structured so the model refuses to let you answer lazily.

Made by Isaac Peterson · @isaacpetersonau
From the post: "I Made Claude Interview Me for a Job. My Own." — since rebuilt around multiple choice, gap-typing, and a real networking strategy.
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