Case study 02 — Leave Management

Leave management — year-end should not be a crisis

From manual carry-forward calculations and December chaos to modular policies, automation, and team availability visibility

RoleLead UX Designer
PlatformWeb + Mobile
Users4 personas — 100k+ employees, 100+ companies
ScopePolicy Setup · Balance Tracking · Approvals · Holiday Calendar · Year-end
Leave Management
Step 1 — Empathise

December was a crisis. Every year. For every HR manager.

Research sessions with 30+ companies revealed a consistent pattern: year-end leave processing was the single most stressful moment in the HR calendar. HR managers spent 3–4 weeks manually calculating carry-forward, chasing manager approvals, and reconciling policy compliance under payroll pressure.

Persona 01 — Owner
🏢
Owner / Company Admin
Sets leave policy, monitors compliance, manages year-end
"I don't want to think about carry-forward every year. Just automate it based on the rules I've already set."
Says
Leave policies should match our company culture. Carry-forward rules must comply with labour law. I need to see leave liability as part of cash flow planning.
Thinks
Are our leave policies actually working? Are we compliant? What is our total leave liability for the year?
Does
Approves leave policy changes. Reviews overall leave utilisation. Monitors compliance risks. Signs off on year-end carry-forward decisions.
Feels
Concerned about labour law compliance. Satisfied when policies are enforced automatically. Worried about leave liability accumulation in balance sheets.
Pain
  • Carry-forward must be manually calculated at year-end
  • Leave accumulation becomes complex with multiple policies
  • Compliance risk when rules are not uniformly applied
  • No visibility into total leave liability for financial planning
Need
  • Automatic year-end carry-forward based on set rules
  • Clear leave liability summary for financial reporting
  • Compliance audit trail for every leave decision
  • Policy effective-date control (changes apply from date X)
👩‍💼
HR Manager
Daily approvals, policy implementation, year-end processing
"December is the worst month of my year. I'm calling managers to approve leaves while simultaneously trying to calculate carry-forward in Excel. All before payroll closes."
Says
I need to close leave balances before payroll runs. Managers don't approve pending leaves on time. Carry-forward has too many edge cases.
Does
Creates and assigns leave policies. Processes leave requests. Calculates carry-forward manually. Sends reminders to managers. Handles year-end compliance.
Sees
All pending leave requests across teams. Employees with unused leave approaching expiry. Manager approval delays. Payroll deadline on the calendar.
Feels
Overwhelmed in December. Frustrated when managers delay approvals. Anxious about compliance. Satisfied when year-end closes cleanly.
Pain
  • Year-end carry-forward is manual and error-prone
  • Managers don't approve pending leaves before year-end
  • Late declarations from employees
  • Policy rules are complex and have overlaps
  • No automated reminders for pending actions
  • Cannot see team coverage when approving leaves
Need
  • Auto carry-forward calculation based on defined rules
  • Automated reminders to managers 30 days before year-end
  • Batch approval tools for pending leave backlog
  • Team availability calendar for coverage decisions
  • Policy overlap validation built into setup flow
Persona 02 — Team Manager and Employee
👔
Team Manager
Approves team requests, manages coverage, plans projects
"I have 50 leave requests in December I haven't seen. HR calls me but I'm in end-of-year project crunch."
Says
I approve leaves but I need to see team availability first. I don't want to have half the team on leave during a critical delivery.
Thinks
Who else is on leave this week? If I approve this, will I have enough coverage? I need to see the impact before I click approve.
Does
Reviews leave requests one by one. Checks informally with team for coverage. Approves or declines based on gut feeling. Forgets to process requests during busy periods.
Feels
Burdened by approval volume. Blind when making coverage decisions. Guilty about delays. Frustrated when HR escalates overdue approvals.
Pain
  • Too many approval requests pile up
  • No team availability calendar to check coverage
  • Approving blind — can't see who else is on leave
  • No reminder until HR escalates urgently
  • December backlog is overwhelming
Need
  • Team calendar showing leave vs availability by day
  • Batch approval for backlog clearance
  • Automatic reminders 7 days before requests expire
  • Mobile approval — quick actions from anywhere
👤
Employee
Applies for leave, checks balance, plans personal time
"I applied for leave and still don't know if it's approved. My manager hasn't said anything."
Says
I don't know how many leaves I have left. When does carry-forward happen? Will my leaves expire? How long does approval take?
Does
Applies for leave via HRMS. Waits for notification. Checks status manually. Asks HR or manager directly for updates. Plans personal events around uncertainty.
Sees
Opaque leave balance numbers. No clear breakdown of casual, sick, earned. No indication of when leaves expire or carry-forward.
Feels
Uncertain about balance. Frustrated waiting for approval. Anxious about year-end leave expiry. Relieved when quickly notified.
Pain
  • Unclear leave balance breakdown
  • Slow approvals — no timeline visibility
  • No alerts before leaves are about to expire
  • No clarity on year-end carry-forward rules
  • Blue collar workers: SMS only, no app visibility
Need
  • Live balance breakdown by leave type
  • Push notification when leave approved/declined
  • Warning when leaves are expiring
  • Plain-language summary of their leave policy
  • SMS fallback for blue collar workers
HR Admin emotional journey — leave management throughout the year
From policy creation through routine approvals to year-end carry-forward chaos and recovery
😐Policy
Creation
😟Assign to
Employees
😊Routine
Approvals
😊Mid-year
Running
😐Year-end
Prep
😡Carry-forward
Chaos
😌New Year
Set
Key insight from research: The most painful moment in leave management is not an approval workflow problem — it's a timing and automation problem. By the time HR realises carry-forward calculations are wrong, it's already November. The fix: automate carry-forward based on policy rules 30+ days before year-end, not on January 1st.
Step 2 — Define

Four distinct failure modes across the leave lifecycle.

HR Manager · Owner
Policy complexity problem
Leave rules vary by employment type, grade, location, and tenure. Multiple overlapping policies create edge cases — one employee can fall under two policies with different carry-forward rules, with no system validation to catch the conflict.
HR Manager
Year-end processing bottleneck
December: managers haven't processed pending leaves, HR must manually calculate carry-forward across hundreds of employees in Excel, declarations from employees still trickling in, payroll deadline immovable. Result: 3–4 weeks of high-stress manual work.
Team Manager
Coverage visibility blind spot
Managers approve leave requests one-by-one without seeing team-wide availability. A manager can approve 5 requests in a week without knowing 3 others were already approved — leaving critical projects understaffed.
Employee · Blue Collar
Communication and transparency gap
Employees don't know their leave balance, when it expires, or what carry-forward rules apply to them. Blue collar workers receive no app notifications at all — only SMS after decisions are made, with no context.
Step 3 — Ideate

Modular policies again. But this time, year-end automation is the centrepiece.

We mapped the leave policy creation flow across 5 approaches (from single-form to wizard-based), validating each with HR managers. The modular approach (same structure as attendance) won again — but the bigger ideation breakthrough was the year-end automation trigger.

Year-end automation concept

January 1st auto-reset
Apply carry-forward rules on January 1st automatically. Simple, but gives HR no advance warning and no opportunity to fix edge cases before it happens. Managers haven't approved all pending leaves yet. Rejected.
Chosen
30-day advance automation
System starts the year-end process 30 days before December 31: sends reminders to managers, calculates projected carry-forward, surfaces pending leaves for batch approval, flags compliance issues. HR has time to fix problems before they're locked. Chosen.

Holiday calendar mental model

Research showed HR managers had a natural mental hierarchy for holidays: National + Compulsory first, then Optional floaters, then State-specific. We mirrored this hierarchy in the UI — build National foundation first, layer Optional on top, add State-level last. This reduced setup confusion significantly.

Leave balance widget for employees

Single number balance
Show one total leave balance. Simple, but hides type breakdown (casual vs sick vs earned) which employees need for planning. Creates confusion when different leave types have different rules. Rejected.
Chosen
Breakdown widget with expiry
Used / Available / Carry-forward / Expiring soon — all visible at a glance per leave type. Green/amber/red indicators for expiry timeline. Employee can plan accurately and won't be surprised at year-end. Chosen.
Step 4 — Prototype

Modular setup + automated year-end + team availability calendar.

HR Admin — Leave policy setup flow

Create Policy→ Define Rules→ Carry-forward Settings→ Applicable For→ Assign Employees→ Policy Active

HR Admin — Leave management task flow

Phase Policy Creation Daily Approvals Mid-year Year-end (Nov) Year-end (Dec)
Activity Create leave policy with types, limits, carry-forward rules. Assign to employee groups. Configure holiday calendar by level. Review and approve leave requests. Handle escalations from managers. Monitor team availability dashboard. Review leave utilisation trends. Check employees with high unused balances. Send usage reminders. System triggers 30-day warning. Send reminders to managers for pending approvals. Preview projected carry-forward. Final batch approval of pending requests. Auto carry-forward applied per rules. New year policies activate. Compliance report generated.
Feeling Neutral — familiar setup process Satisfied — streamlined with team calendar view Neutral — proactive checks prevent surprises Relieved — system flags issues early, not late Satisfied — year-end closes cleanly without Excel
Design decision Policy preview showing affected employee count and any overlap before activation Team availability calendar shown alongside approval form — coverage context before clicking Approve Proactive expiry alerts sent to employees 2 weeks before year-end Auto-generated carry-forward preview report for HR to review and adjust before lock One-click confirm for automated carry-forward calculation. Audit trail generated automatically.
Step 5 — Test and Ship

Validated with HR teams from 6 companies. Three changes before final release.

What shipped

🧩
Modular policy system
Policy rules and employee assignment decoupled. Update carry-forward rules without recreating assignments.
🤖
Year-end automation
Configurable advance trigger. Auto-reminders, carry-forward preview, batch approval, then auto-process on December 31.
📅
Team availability calendar
Managers see team coverage week-by-week before approving — not one-by-one in isolation.
📊
Leave balance widget
Used / Available / Carry-forward / Expiring per type. Expiry countdown in amber/red.
📱
SMS for blue collar workers
Leave approvals, balance notifications and year-end alerts via SMS for workers without app access.
🗓️
Holiday calendar (3-tier)
National + Compulsory → Optional floaters → State-specific. International date support. Employee self-selection for optional holidays.
3–4 wks
Year-end manual effort eliminated by automation
100k+
Employees on leave policies — monthly active usage
92%
Reduction in manual carry-forward calculations (self-reported)