War-game an onboarding checklist before tool access, buddy assignments, and first-week tasks harden into how every new hire starts.
Onboarding checklists fail when access tickets lag the start date, when buddies are named without protected time, when "read the wiki" stands in for a real walkthrough, and when success is measured as boxes checked rather than a new hire who can clear a real task. A tidy Notion page is not evidence.
Freeze first
State the roles the checklist covers, the day-one access and compliance gates, who owns each step, the buddy model and time budget, and the success metric after thirty days. Attach IT provisioning SLAs, security training requirements, manager scripts, and the kill criteria if completion rates hide stalled work. If people ops, IT, and hiring managers disagree on who unblocks a stuck step, reconcile before seating.
Name the decision you will make if the war game finds nothing new, and the hold criteria if any critical access path lacks an owner or a measured lag.
Attack surfaces
- Access fiction: accounts that "should" exist by day one and routinely do not.
- Buddy theater: named helpers without calendar protection or a mandate.
- Wiki dumping: long reading lists that replace live walkthroughs.
- Role blur: one checklist for every function that needs different first tasks.
- False completion: checked boxes while the new hire still cannot ship a small task.
Optional counsel seat if background checks or regulated training bind start dates. Optional security seat if privileged access is in the first week.
How to run it
Feed Pingpong the draft checklist, provisioning notes, and open risk list. Early passes steelman the sequence. Later passes attack from new hire, manager, IT, people ops, and security seats. End with a pass that turns surviving objections into fewer day-one blockers, clearer owners, or a hold. Delete invented "everyone finishes in a week" claims and dual-counted buddy hours.
Ask people ops and IT seats to price the first-week experience the checklist will create. If day-one language promises tools that still wait on a ticket queue, new hires will learn that the checklist is theater. Write the intended sequence, the escalation path for stuck access, and the steps you will refuse to fake as complete, then attack whether learning still happens under that discipline.
Force a day-after narrative: what happens if a laptop ships late, if a buddy is on PTO, or if security training blocks production access for three days. If those stories are stronger than your mitigation plan, fix the checklist before the next cohort starts. Related: pretend you are the new hire, war-game a hiring plan, pretend you are the ops lead, war-game a delegation framework, and the war-game decisions hub. Process: how to run a Pingpong.