---

name: okr-planning description: >- Guides OKR (Objectives and Key Results) planning: writing ambitious objectives with measurable key results, aligning teams, running the quarterly cycle, and scoring results. Use when a user asks to "write OKRs for next quarter", "review our OKRs", "turn these goals into key results", "run OKR planning", or "score our OKRs". Applies frameworks from John Doerr (Measure What Matters), Christina Wodtke (Radical Focus), and practices from Google and Intel. license: Apache-2.0 compatibility: No special requirements metadata: author: terminal-skills version: 1.1.0 category: business tags:

• okrs
• goals
• planning
• alignment
• objectives

---

OKR Planning — Objectives and Key Results

Overview

This skill guides OKR (Objectives and Key Results) planning: it helps product teams set ambitious goals, define measurable outcomes, align teams, and run quarterly planning cycles. This skill applies frameworks from John Doerr (Measure What Matters), Christina Wodtke (Radical Focus), and practices from Google, Intel, and high-growth startups.

Instructions

Writing OKRs

## OKR Structure

**Objective**: Qualitative, inspiring, time-bound
- Answers: "Where do we want to go?"
- Should be ambitious but achievable (for a stretch objective, 70% completion = good)
- One sentence, memorable, motivating

**Key Results**: Quantitative, measurable, specific
- Answer: "How do we know we're getting there?"
- 3-5 per objective
- Include a number (baseline → target)
- Measurable at the end of the quarter with no debate

### Good OKR Examples

**Objective**: Make onboarding so good that users succeed on day one

Key Results:
1. Increase Day 1 activation rate from 35% to 55%
2. Reduce median time-to-first-value from 14 minutes to 4 minutes
3. Decrease "how do I get started" support tickets from 120/week to 30/week

**Objective**: Build a revenue engine that scales without scaling the sales team

Key Results:
1. Increase self-serve revenue from $40K to $100K MRR
2. Achieve free-to-paid conversion rate of 8% (currently 3%)
3. Launch usage-based pricing tier with 50+ paying customers

**Objective**: Become the most trusted brand in our category

Key Results:
1. Achieve NPS score of 60 (currently 38)
2. Publish 20 case studies from customers with measurable ROI
3. Reach 5,000 community members in Discord (currently 1,200)

### Bad OKR Examples (and fixes)

❌ Objective: "Improve the product"
(Too vague, not inspiring)
✅ "Deliver a product experience that users recommend to peers"

❌ KR: "Launch feature X"
(Output, not outcome — shipping ≠ success)
✅ "Feature X drives 30% increase in weekly active users"

❌ KR: "Improve customer satisfaction"
(Not measurable — what number? from what to what?)
✅ "Increase CSAT score from 3.8 to 4.5 on post-interaction survey"

❌ KR: "100% of sprint stories completed"
(Activity metric, not impact metric)
✅ "Reduce average bug fix time from 5 days to 2 days"

Quarterly Planning Process

## Run Quarterly OKR Planning

### Week -3: Preparation
- Review last quarter's OKRs: what scored well? what missed? why?
- Gather input: customer feedback, analytics, team retrospectives
- Leadership shares company-level objectives for next quarter
- Each team lead drafts 1-2 team objectives aligned to company OKRs

### Week -2: Alignment
- Cross-team review: do team OKRs create conflicts or dependencies?
- Resolve resource conflicts (two teams need same engineer)
- Identify shared KRs (both teams contribute to the same metric)
- Challenge: "If we hit all these KRs, will we actually achieve the objective?"

### Week -1: Finalization
- Lock OKRs (no changes after this point)
- Each team presents OKRs to the company (transparency)
- Set up tracking: dashboard, weekly check-in cadence
- Identify leading indicators for each KR (don't wait until end of quarter)

### During Quarter: Execution
**Weekly**: 15-minute OKR check-in per team
- Traffic light each KR: 🟢 on track | 🟡 at risk | 🔴 off track
- For 🟡/🔴: what's the plan to get back on track?
- No surprises at quarter end

**Mid-quarter**: Formal review
- Are KRs still the right measures?
- Any external changes (market, competitor, tech) that require adjustment?
- Adjust confidence levels, not the KRs themselves

### End of Quarter: Scoring and Retrospective
Score each KR: 0.0 to 1.0
- 0.0-0.3: Failed to make meaningful progress
- 0.4-0.6: Made progress but fell short
- 0.7-1.0: Delivered

Average KR scores = Objective score.

Label every OKR before the quarter starts — the expected score differs:
- Committed OKR (a launch date, an SLA, a compliance deadline): expected score 1.0;
  anything lower needs an explanation of what went wrong in planning or execution
- Aspirational (stretch) OKR: expected average 0.6-0.7 with high variance;
  consistently scoring 1.0 here means the goals aren't ambitious enough

OKR Alignment

## Align OKRs Across Teams

### Company → Team → Individual

Company Objective: "Achieve product-market fit in the SMB segment"
  └─ Company KR: "Reach $500K ARR from SMB customers"

    Product Team Objective: "Make the product irresistible for SMB users"
      └─ KR: "SMB trial-to-paid conversion from 5% to 15%"
      └─ KR: "SMB onboarding completion from 40% to 80%"

    Marketing Team Objective: "Fill the SMB pipeline with qualified leads"
      └─ KR: "Generate 500 qualified SMB leads per month"
      └─ KR: "Reduce SMB CAC from $800 to $400"

    Engineering Team Objective: "Enable SMB self-service at scale"
      └─ KR: "99.9% uptime for core workflows"
      └─ KR: "Reduce p95 page load from 3s to 1s"

### Rules for Alignment
1. Teams own their OKRs — company provides direction, not dictation
2. Roughly half bottom-up — about half of objectives (and nearly all KRs) should come from the teams, not from the top
3. Dependencies must be explicit — if Team A needs Team B, it's in the OKRs
4. No duplicate KRs — if two teams share a KR, assign one owner
5. Individual OKRs are optional — team-level is sufficient for most orgs

Common Pitfalls

## Avoid OKR Anti-Patterns

1. **Too many OKRs**: Max 3 objectives, 3-5 KRs each. If everything is a priority, nothing is.

2. **KRs as tasks**: "Launch feature X" is a task. "Feature X drives 20% increase in activation" is a KR. Measure impact, not output.

3. **Sandbagging**: If teams always score 1.0 on aspirational OKRs, they're setting easy goals. Stretch OKRs should feel uncomfortable.

4. **OKRs as performance reviews**: If KR scores affect compensation, teams will sandbag. Decouple OKRs from performance reviews.

5. **Set and forget**: OKRs require weekly check-ins. Without them, you discover failure at the end of the quarter.

6. **No baseline**: "Improve retention" means nothing without "from X% to Y%". Always include the current number.

7. **Missing counter-metrics**: "Increase signups" without tracking quality leads to gaming (bot signups, low-quality traffic).

8. **Mixing committed and aspirational**: A commitment marked as a stretch gets under-resourced and missed; a stretch marked as a commitment makes teams defensive. Label each one.

Examples

Example 1: Drafting OKRs for a product launch

User request:

We're launching Loomboard, a critique tool for remote design teams, on August 12.
Draft our Q3 OKRs. Today: 12 beta teams, 140 teams on the waitlist, 0 paying.

The agent asks who owns each number and which results are promises to customers, then returns:

**Objective (aspirational):** Remote design teams run their weekly critique in Loomboard

Key Results:
1. 40 teams hold 3+ critique sessions in their first 30 days (baseline: 0 of 12 beta teams)
2. Week-4 team retention reaches 60% (no baseline — the launch cohort reaches week 4 on September 9)
3. Median time from signup to first shared board drops from 26 minutes to under 10

**Objective (committed):** Launch on August 12 without losing customer work

Key Results:
1. Zero data-loss incidents in the launch cohort
2. p95 board load time falls from 4.1 s to under 2 s at 500 concurrent editors
3. All 12 beta teams run a critique in their production workspace before launch day (today: 0 of 12)

Counter-metric: support tickets stay under 0.5 per active team per week.
Open question: KR2 has no baseline; treat the first score as a calibration, not a grade.

Example 2: Reviewing quarterly OKRs for measurability and ambition

User request:

Here are our Q2 OKRs for the platform team. Check if key results are measurable
and objectives are ambitious enough.

O: Improve platform reliability
KR1: Migrate all services to the new Kubernetes cluster
KR2: Improve uptime
KR3: 100% of on-call tickets closed

The agent returns a line-by-line review with rewrites:

| Item | Problem | Rewrite |
|------|---------|---------|
| O: Improve platform reliability | Vague, describes no end state | Product teams ship without thinking about the platform |
| KR1: Migrate all services | Output — a task, not a result | Node-level incidents fall from 9 to 2 per quarter (the migration is the initiative) |
| KR2: Improve uptime | No baseline or target | API availability rises from 99.82% to 99.95% (30-day rolling) |
| KR3: 100% of tickets closed | Activity metric, invites closing tickets early | Median time to restore falls from 47 to 15 minutes |

Missing:
- Counter-metric: deploy frequency must not drop below 20 per week
- Labels: 99.95% availability is a commitment (expected score 1.0);
  the incident reduction is a stretch (0.7 is a good result)
- Owner for each KR

Guidelines

1. Outcomes over outputs — Key Results measure impact on users/business, not tasks completed or features shipped
2. Ambitious but achievable — For stretch OKRs target 70% completion; consistently scoring 1.0 means you're not stretching enough. Committed OKRs are expected to hit 1.0
3. 3 objectives max — Focus is the point of OKRs; if you have 8 objectives, you have zero priorities
4. Weekly check-ins — Traffic-light each KR weekly; fix problems in week 3, not week 12
5. Decouple from compensation — OKRs are a goal-setting tool, not a performance evaluation tool; linking to bonuses kills ambition
6. Include baselines — Every KR needs "from X to Y"; without a baseline, you can't measure progress
7. Counter-metrics — For every metric you're trying to improve, define one you don't want to hurt
8. Retrospect every quarter — Score OKRs, discuss what worked and what didn't, apply learnings to next quarter's planning