OKR Change Management

This skill provides the complete change management framework for rolling out an OKR program. It covers the nine-step playbook, cadence tiers, anti-patterns, and timing benchmarks.

Nine-Step OKR Rollout Playbook

Step 1: Executive Alignment

Objective: Secure executive buy-in and define the "why" behind OKRs. Owner: CEO / COO Artifact: Executive alignment memo with OKR charter Success Criteria: Executive team unanimously agrees on OKR purpose and scope Timeline: Week 1-2

Step 2: Pilot Selection

Objective: Choose 1-2 teams for the initial OKR pilot. Owner: OKR Program Lead Artifact: Pilot team selection rationale Success Criteria: Pilot teams selected, managers briefed, timeline agreed Timeline: Week 2-3

Step 3: Training and Enablement

Objective: Train pilot teams on OKR methodology. Owner: OKR Program Lead + HR Artifact: Training materials, workshop recordings Success Criteria: All pilot team members attend workshop, pass quiz (≥80%) Timeline: Week 3-4

Step 4: First Cycle Draft

Objective: Draft OKRs for the pilot teams using live data. Owner: Pilot team managers Artifact: Draft OKR set per pilot team Success Criteria: Drafts pass schema validation, baselines are real, targets use three stances Timeline: Week 4-5

Step 5: Approval and Launch

Objective: Review, approve, and activate the first OKR cycle. Owner: Executive sponsor + pilot team managers Artifact: Approved OKR set, Asana project (optional) Success Criteria: "APPROVED: OKR-{cycle}" recorded, cadence calendar published Timeline: Week 5-6

Step 6: Operating Rhythm Activation

Objective: Establish and begin the weekly/monthly/quarterly cadence. Owner: OKR Program Lead Artifact: Cadence calendar, first weekly check-in template Success Criteria: First 3 weekly check-ins completed on time Timeline: Week 6-8

Step 7: Mid-Cycle Review

Objective: Conduct a formal mid-cycle health check. Owner: Executive sponsor Artifact: Mid-cycle scorecard, intervention list Success Criteria: All at-risk KRs have documented interventions Timeline: Mid-quarter

Step 8: Scale to Organization

Objective: Extend OKRs to all departments based on pilot learnings. Owner: OKR Program Lead Artifact: Org-wide rollout plan, department alignment map Success Criteria: All departments have approved OKR sets with cascade links Timeline: Next quarter

Step 9: Governance and Automation

Objective: Automate cadence, reporting, and calibration. Owner: RevOps / OKR Program Lead Artifact: Automated dashboards, cadence tasks, learning engine active Success Criteria: Zero manual reporting, calibration engine has ≥4 cycles of data Timeline: Quarter 3+

Three-Tier Cadence Design

Weekly Check-In (15-30 minutes)

• Who: KR owners + team lead
• Format: Async update or brief standup
• Content: KR progress update, blockers, help needed
• Template: templates/reports/weekly-kr-update.md
• Red Flags: >2 consecutive missed check-ins, same blocker reported 3+ weeks

Monthly Scorecard (45-60 minutes)

• Who: Department leadership + executive sponsor
• Format: Synchronous meeting with pre-read scorecard
• Content: One-page scorecard, biggest movement, top risks, decisions needed
• Template: templates/reports/monthly-scorecard.md
• Red Flags: No decisions made for 2+ months, scorecard not distributed before meeting

Quarterly Review (90-120 minutes)

• Who: Full leadership team
• Format: Formal presentation with Q&A
• Content: Cycle outcomes, what worked/didn't, calibration, next cycle planning
• Template: templates/reports/quarterly-review.md
• Red Flags: Review deferred or cancelled, no learning capture, next cycle not drafted

Adoption Anti-Patterns (Six Failure Modes)

1. Trophy OKRs

Symptom: OKRs are written once, never checked, displayed for optics only. Root Cause: No operating rhythm established; OKRs disconnected from daily work. Fix: Activate weekly check-ins within 1 week of approval.

2. Waterfall Targets

Symptom: Targets are imposed top-down without team input or data grounding. Root Cause: Executive team sets all targets without consulting KR owners. Fix: Use collaborative drafting with three stances. Team proposes base, leadership adjusts.

3. KR Stuffing

Symptom: Objectives have 8+ KRs, many are activity metrics (not outcomes). Root Cause: Conflating tasks and deliverables with measurable outcomes. Fix: Enforce 2-5 KRs per objective. Apply the "would a customer notice?" test.

4. Orphan Objectives

Symptom: Team/department objectives don't link to any company objective. Root Cause: OKRs written in isolation without cascade alignment. Fix: Run alignment audit before approval. Block activation of unlinked objectives.

5. Check-In Theater

Symptom: Check-ins happen but are superficial — "all green" when nothing has changed. Root Cause: No accountability for honest updates; fear of showing red. Fix: Normalize yellow/red as healthy signals. Celebrate early escalation.

6. Retrospective Amnesia

Symptom: Cycle ends without outcome recording; same mistakes repeat. Root Cause: No formal close process; team moves immediately to next cycle. Fix: Block next cycle generation until /okr-retrospective is completed.

Rollout Timing Benchmarks

Company Size	Pilot Duration	Full Rollout	Steady State
<50 employees	1 quarter	2 quarters	Quarter 3
50-200 employees	1 quarter	2-3 quarters	Quarter 4
200-1000 employees	1-2 quarters	3-4 quarters	Quarter 5-6
1000+ employees	2 quarters	4-6 quarters	Quarter 7+

Key Milestones:

• Quarter 1: Pilot team running full cadence
• Quarter 2: 2-3 additional departments onboarded
• Quarter 3: Org-wide adoption with cascade alignment
• Quarter 4+: Learning engine calibration reaches decision-grade