HR playbook · AI Employee: Harry

Time Off & Leave Requests

Requests resolved in <24h; balance auto-updated

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The problem

Time-off requests are the single most repetitive HR workflow. Employees submit a form, HR checks the balance, the manager approves, the calendar updates, payroll gets notified, coverage gets arranged. Every step is trivial. Every step is a place the process breaks. Every year the queue grows with headcount.

At a glance
Trigger
Form
Approvals
Manager approval
What it does
Writes to your systems
Systems
Workday · HiBob · Rippling · Google Calendar
How it feels in production

An hour-by-hour walkthrough.

9:14am Tuesday. Priya DMs Harry: "I want to take Thu-Fri off next week." Harry pulls her leave balance from Workday (7.5 days remaining), checks team coverage for those dates (nobody else on Priya's team is out), and posts a request card to her manager Alex. 9:18am. Alex sees the card, taps Approve. Harry writes the leave request back to Workday, adds the dates to Priya's Google Calendar as an out-of-office event, sets her Slack status to 'On leave — back Monday' for those days, and posts to the team channel: "Priya is out Thu-Fri." 9:19am. Priya gets a confirmation: dates approved, balance updated (5.5 days remaining), coverage confirmed, calendar blocked. From ask to done in five minutes; zero forms, zero waiting. If Alex is out that week, the request escalates to Alex's designated delegate automatically. If Priya asks for more days than her balance covers, Harry flags the shortfall and asks whether she wants to convert to unpaid or reduce the request. If two people on the same team try to be out on the same day, Harry flags the coverage gap before routing to the manager.
How it works

Step by step.

  1. 01

    Collect leave dates + type

    Employee DMs Harry in Slack / Teams (or fills a portal form). Harry parses the dates and leave type (vacation / sick / parental / bereavement / unpaid), asks a clarifying question if the type is ambiguous.

    Slack · Teams · Portal
  2. 02

    Check balance and coverage

    Read the employee's leave balance from HRIS. Check the team's calendar for the requested dates — if a coverage gap is likely, surface it in the request card so the manager sees it before approving.

    Workday · BambooHR · HiBob · Google Calendar
  3. 03

    Route to manager

    Post an approval card to the manager in Slack / Teams / email with dates, balance, coverage note, and one-tap Approve / Decline / Delegate. Deadline auto-set (default 24h); escalation to the manager's delegate if untouched.

    Slack · Teams · Email
  4. 04

    Apply approved leave

    Write the leave request back to HRIS, update the balance, add the dates to the employee's Google Calendar / Outlook, set their Slack / Teams status for those dates, post the team-channel note. All writes idempotent.

    Workday · Google Calendar · Outlook · Slack · Teams
Systems and wiring

What you connect to make this run.

Workday · BambooHR · HiBob · Rippling · ADP

read+write

OAuth credential with leave-request scopes. Balance read + leave-write. Custom leave types map to your HRIS's own leave categories.

Google Calendar / Outlook

write

Per-user OAuth (delegated) via workspace-wide app. Out-of-office events created on approval and cleaned up if the request is later revoked.

Slack · Teams

write

Bot posts request cards to managers, updates employee status on approved dates, posts team notifications. One bot, three surfaces.

What changes

Before and after, honestly.

Time from request to approval
Before
2-5 business days across email chains
After
Under 24 hours, most under 1 hour
Manager time spent on approvals
Before
~5 min per request across form-checking + calendar-checking
After
One tap on a pre-filled approval card
Coverage-gap incidents
Before
Manager discovers overlap after the second person is out
After
Flagged in the request card before approval
HR tickets on 'what's my balance?' / 'did my request go through?'
Before
~15% of HR ticket volume
After
Near zero — Harry answers instantly
Related

Playbooks that pair with this one.

HR

Parental Leave Intake

Parental leave is a specialised variant with benefits-election flow.

HR

Manager Change Cascade

Ensures approval routing follows the current manager after a reporting-line change.

Frequently asked

Answers about this playbook.

What if I request more days than my balance allows?

Harry surfaces the shortfall in the request card. You can reduce the request, convert the overage to unpaid leave (if your policy allows), or borrow from next year's accrual (per your policy). Manager still sees the underlying details before approving.

How does it handle regional leave laws?

Per-country policy files hold the local rules — statutory minimums, waiting periods, notification requirements. Harry checks the requester's employee location before offering leave types and enforces the local rules before submitting.

Can I request leave for a team member as a manager?

Yes — managers can submit on behalf of a direct report (with an audit note attached). The employee still gets notified and can decline if the request was mistaken.

What if two people on my team are already out?

Harry surfaces the coverage gap in the manager's approval card with a rationale ("Priya and Alex are both out Thu; approving this makes three of five out"). Manager decides; the coverage flag is informational, not blocking.

Does this work for hourly workers?

Yes — leave requests convert to hours per your policy, HRIS updates the timesheet, and payroll gets notified in the next cycle. Salaried and hourly variants use the same playbook with different balance-conversion logic.

See it run on your data.

Free plan, no credit card. Connect the systems this playbook needs and run it against a past event first.

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