30-60-90 Day Check-In Scheduler: Catch New-Hire Problems Before They Quit

The problem this kills

You mean to check in on new hires. You really do. But the day someone starts, the calendar takes over — and the 30-day check-in slides to day 45, the 60-day one never happens, and by month three you find out the person has been quietly miserable since week two and is already interviewing elsewhere.

The cost is brutal and invisible until it isn't: a new hire who churns in their first 90 days burns the recruiting spend, the manager's ramp-up time, and the team's morale — and almost always the warning signs were there at the 30-day mark, if anyone had asked. Sticky notes and good intentions don't scale, and a shared spreadsheet of "check-ins to do" is the first thing everyone ignores. You don't need an expensive HRIS module to fix this, and you don't need to be a developer.

What you'll build

A simple internal web tool. You add a new hire — name, start date, manager — and the tool instantly schedules their 30, 60, and 90-day milestones, computed from the start date and nudged off weekends and company holidays. At each milestone it emails a short, structured check-in to the manager and a separate confidential one to the employee, collects the answers, and scores them against your rules. Anyone whose answers cross your at-risk threshold gets flagged for HR review — never auto-escalated. HR reads the flagged responses, decides on follow-up, and logs it; if an escalation to the manager's manager is warranted, it waits for HR's approval before a single email goes out. At any point you can export a clean check-in-status CSV for your records or your HRIS.

What's inside the Implementation Plan

The downloadable plan is a step-by-step file you paste into an AI coding agent. It opens by interviewing you about your business — how you onboard today and who owns it, where your roster lives, exactly what your employee/manager fields are named, your typical and peak monthly hiring volume, what "at-risk" actually means in your shop, your confidentiality rules, and your messy edge cases (early terminations, start-date changes, a manager who's also the employee's reviewer) — and then it tailors the data model, the scoring, and every later step to your answers. This is not a generic template; the agent reflects a short spec back to you and waits for your thumbs-up before it builds anything. From there it walks the agent through the roster import, the milestone-date math (skip weekends and holidays), the prompt emails, the response capture and scoring, the at-risk flagging, the HR review-and-approve screen, and the CSV export — each step with a ready-to-copy prompt. There's also a fallback so you can build the whole thing today even with no API to your HRIS.

The governance it includes (this is the point)

People data is sensitive, so this ships with the controls an HR team needs: login so only your team can use it, row-level security so you only ever see your own organization's hires, a complete audit trail of who viewed, reviewed, and approved which check-ins and when, a hard human-approval gate so no escalation to a manager's manager goes out until HR signs off, and duplicate guards keyed on employee + milestone so the same check-in can't be scheduled or scored twice. Employee responses are kept appropriately confidential — managers see their own prompt, HR sees the flags, and the raw employee feedback stays where it belongs.

Who it's for

People-ops leads, HR generalists, and managers who fully intend to do new-hire check-ins but lose the thread the moment the new person actually starts. If you can describe how you'd want to follow up on a struggling new hire, you can build this.

You've got this — start with the plan, paste the first prompt, answer the interview, and you'll have your first new hire's milestones scheduled the same afternoon.