Overview
Most onboarding is a wall of docs plus 40 Slack pings. A Custom GPT loaded with your handbook, org chart, and glossary lets new hires get answers instantly — including the small questions they'd feel dumb asking a human ('what does OKR mean here?', 'when do expenses get reimbursed?').
How it works
- You create a Custom GPT and upload handbook.pdf, org-chart.pdf, glossary.md, and benefits-summary.md.
- The system prompt sets tone (warm, direct) and enforces citations to the source doc.
- The GPT is shared with the workspace via a link in the offer letter.
- New hires ask questions in weeks 1-2 and rate answers with 👍/👎.
- You review the low-rated answers monthly and add missing content to the handbook.
Benefits
- New hires get answers in 10 seconds, not 24 hours.
- The handbook improves because the GPT surfaces gaps.
- Managers get their calendar back — no more 'quick question?' pings.
Use cases
- Remote-first companies with no hallway to overhear things in.
- Rapidly hiring teams where the same 30 questions come up.
- Ops teams maintaining an internal wiki nobody reads.
Step-by-step guide
Step 1: Audit the source docs
Handbook, org chart, glossary, benefits, tooling list. If a doc is out of date, don't upload it — fix or omit.
Step 2: Set the tone in the system prompt
'You are the friendly onboarding buddy. Warm, direct, cite the doc for every answer.' Tone matters more than instructions for adoption.
Step 3: Enforce the citation rule
'If the answer isn't in the uploaded docs, say so and suggest who to ping in Slack.' This kills hallucination.
Step 4: Publish and share the link
In offer letters, in the welcome Notion, in the #newhires channel. Onboarding managers should mention it in day-1 kickoff.
Step 5: Read the transcripts weekly
OpenAI shows conversations to the creator. The questions people ask are the gaps in your handbook — this is free research.
Example
New hire: 'When do I get my laptop reimbursed if I bought my own?' GPT: 'Per the Handbook §4.3, laptop reimbursement is $2,000 within your first 30 days. Submit via Ramp with the receipt. If your purchase was over that, ping @IT-Ops.'