---
id: "action-legitimize-experimentation"
type: "action-item"
source_timestamps: ["§ What Leaders Can Do"]
tags: ["culture", "innovation"]
related: ["concept-side-quests", "concept-praiseworthy-exploratory-testing", "entity-anthropic"]
action: "Create a formally named, sanctioned category of work for self-directed AI tinkering outside official roadmaps."
outcome: "Removes the stigma of rule-breaking and brings shadow experimentation into the open."
speakers: ["Eric Anicich", "Jeslyn Brouwers"]
sources: ["execution"]
sourceVaultSlug: "hbr-seg-execution"
originDay: 8
articleStem: "hbr-cl-76-employees-not-transparent-ai-usage"
sourceUrl: "https://hbr.org/2026/06/why-employees-arent-transparent-about-their-ai-usage"
sourceTitle: "Why Employees Aren’t Transparent About Their AI Usage"
---
# Legitimize AI Experimentation via 'Side Quests'

**Commitment #4 — 'Legitimize AI experimentation.'** Part of [[framework-leadership-commitments-for-disclosure]].

**Do:** Borrowing from [[entity-anthropic-d8|Anthropic]]'s [[concept-side-quests]] or Google's 20% time, create a **sanctioned category of work** specifically for self-directed AI experiments outside the official roadmap. Naming this behavior formally converts AI tinkering from perceived 'corner-cutting' ([[concept-blameworthy-deviance]]) into legitimate work, so standard surfacing mechanisms (team demos, repositories) can function and [[concept-praiseworthy-exploratory-testing]] is protected rather than punished.

**Action:** Create a formally named, sanctioned category of work for self-directed AI tinkering outside official roadmaps.

**Outcome:** Removes the stigma of rule-breaking (the Reputational Cost in [[framework-costs-of-ai-visibility]]) and brings shadow experimentation into the open.