30 and 90 Day New Hire Check-In Questions

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Prompt

ChatGPT
Claude
Grok
OpenRouter
You are an HR business partner designing check-ins with new hires to find problems early, while there is still time to fix them.

Role and team: {{ROLE_AND_TEAM}}
What the job ad or offer promised: {{PROMISED_EXPERIENCE}}
Known onboarding weaknesses: {{KNOWN_WEAKNESSES}}
Who will run the conversation (HR, manager, skip-level): {{INTERVIEWER}}

Create two conversation guides, one for day 30 and one for day 90. Each should have 8 to 10 open questions that cover role clarity, workload, tools, manager relationship, belonging, and whether the job matches what was described.

For each question add a one-line note on what a worrying answer sounds like and a suggested follow-up. Add a short opening script that explains what will happen with the answers, and a closing script that confirms next steps.

Constraints: don't ask leading questions; don't promise confidentiality we can't keep; tell the person that serious concerns such as harassment must be taken further. Remind me to record only what is needed and store notes securely.

Output: two guides in numbered lists, then a one-page template for recording themes and actions that has no personal data beyond the employee's initials.

Customize this prompt

Fill in the variables below to personalize this prompt:

ChatGPT
Claude
Grok
OpenRouter

Model Settings

Recommended Models

ChatGPT Claude Gemini

Temperature

0.7

Max Tokens

2000

Additional Notes

Best for: Spotting early-tenure problems while they are fixable

About this prompt

“30 and 90 Day New Hire Check-In Questions” is a free prompt for ChatGPT in the Reasoning & Problem-Solving category, 185 words long, added to The Prompt Index on October 28, 2026 by The Prompt Index. Copy it with the button above, paste it into ChatGPT or any other AI chat assistant, and send it.

It has 4 placeholders to fill in first: {{ROLE_AND_TEAM}}, {{PROMISED_EXPERIENCE}}, {{KNOWN_WEAKNESSES}}, {{INTERVIEWER}}. Use the “Customize this prompt” fields to personalise it before you copy.

Recommended models: ChatGPT, Claude, Gemini.

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