Onboarding Copilot
New hires productive by week two, and nobody re-invents day one
The problem
In most small businesses, onboarding is whoever has time that morning. The new hire shadows someone, gets logins over three days of asking, and forms their picture of the company from whichever coworker talked most. The [Onboarding Plan Builder](/toolbox/onboarding-plan-builder) writes a solid plan for one hire; what it can't do is run the plan, adapt it mid-stream, or remember what worked so hire number four starts better than hire number one. That standing job is what this skill installs.
The tool
Once installed, this skill turns your assistant into the onboarding coordinator your business is too small to employ. It keeps your onboarding playbook (built with you once, from how your business works), and for each new hire it produces the working documents on demand: the before-day-one checklist for you, the week-by-week plan for them, and the check-in scripts for whoever supervises.
The standing part is what earns the install. Log two lines after each check-in and it tracks the hire's progress against the plan, flags what slipped ("still no POS access, day 4"), and adjusts the remaining weeks instead of letting the plan rot. When something confuses a new hire, that confusion gets captured as a playbook fix, so onboarding compounds: every stumble becomes a line the next hire never trips on. It also drafts the 30/60/90 check-in agendas and keeps the record of what was agreed at each one.
What's inside
- A house onboarding playbook, interviewed out of you once and versioned after
- Per-hire documents: prep checklist, week-by-week plan, first-day script
- Check-in tracking from two-line updates, with slipped items flagged
- Confusion capture: what stumped this hire becomes the fix for the next one
- 30/60/90 agendas with a record of what was agreed
- Role variants without starting over (the technician plan and the front-desk plan share the same skeleton)
How to use it
- 1Click "Install skill" on this page and copy the install prompt.
- 2Paste it into your AI assistant (Claude, ChatGPT, anything that accepts pasted text).
- 3Answer the setup questions: the business, the roles you hire, what the first week looks like today.
- 4On a new hire, give it the name, role, and start date; print or send what it produces.
- 5After each check-in, paste two lines about how it went. That habit is the whole system.
Example
An HVAC company with 11 staff hires two techs a year and loses a week each time to improvised starts. The skill interviews the owner once: certifications to verify before day one, the van and tool assignment, who rides along in week one, what "safe to send alone" means. The next hire gets a printed week-one plan, the supervisor gets three check-in scripts, and when the new tech's confusion about the parts-ordering app gets logged, a one-line explainer joins the playbook. By the second hire that year, day one runs off a checklist nobody had to rewrite, and the 60-day check-in agenda already lists the two skills the 30-day notes flagged as shaky.
Pro tip
The two-line check-in log is the habit that separates this from a template folder. Pair it with the [One-on-One Agenda Builder](/toolbox/one-on-one-agenda-builder) once the hire graduates from onboarding: the 90-day record hands the first regular one-on-one its starting agenda.
Related tools
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