Quarterly Planning: Setting OKRs That Work

Quarterly planning is where strategy meets execution. Done well, it creates clarity, alignment, and momentum. Done poorly, it wastes time and creates confusion. This guide walks you through a proven process for quarterly OKR planning that actually works.

Why Quarterly Planning Matters

Quarters provide the perfect timeframe for meaningful progress:

Long enough to accomplish significant goals Short enough to maintain urgency and focus Aligned with business reporting cycles Conducive to regular reset and learning

Annual planning is too slow for modern business. Monthly planning doesn't allow for meaningful progress. Quarterly is the sweet spot.

The Quarterly Planning Timeline

Effective quarterly planning happens over several weeks, not in a single meeting.

6 Weeks Before Quarter End

Leadership Strategy Review

Activities:

• Review company performance year-to-date
• Assess market conditions and competitive landscape
• Identify strategic priorities for next quarter
• Draft preliminary company OKRs

Participants: Executive team

Output: Draft company OKRs and strategic themes

4 Weeks Before Quarter End

Company OKR Draft

Activities:

• Refine company OKRs based on strategy
• Share draft with leadership team for feedback
• Consider dependencies and resource constraints
• Finalize 3-5 company objectives

Participants: CEO and executive team

Output: Finalized company OKRs for next quarter

3 Weeks Before Quarter End

Company OKR Communication

Activities:

• Present company OKRs to entire organization
• Explain the "why" behind each objective
• Open Q&A session
• Share written documentation

Participants: All employees

Output: Company-wide understanding of priorities

2 Weeks Before Quarter End

Team OKR Drafting

Activities:

• Teams draft OKRs that support company objectives
• Identify cross-team dependencies
• Estimate resource requirements
• Get initial feedback from peers

Participants: Team leads and their teams

Output: Draft team OKRs

1 Week Before Quarter End

Alignment and Finalization

Activities:

• Review all team OKRs for alignment
• Resolve conflicts and dependencies
• Confirm resource allocation
• Make final adjustments
• Get leadership approval

Participants: All teams and leadership

Output: Finalized company and team OKRs

First Week of New Quarter

Kickoff and Commitment

Activities:

• All-hands OKR kickoff
• Team-level OKR workshops
• Individual OKR alignment
• Setup tracking and check-ins

Participants: Entire organization

Output: Everyone knows their OKRs and how to track them

The Quarterly Planning Process

Step 1: Review Previous Quarter

Start by learning from the past.

Questions to Answer:

Performance:

• Which OKRs did we achieve?
• Which did we miss, and why?
• What was our overall achievement rate?

Process:

• Did we set the right OKRs?
• Were they too ambitious or not ambitious enough?
• Did we review them regularly enough?

Learnings:

• What worked that we should continue?
• What didn't work that we should change?
• What surprised us?

Example Review Format:

Q3 2024 Review

Overall Achievement: 68% (aspirational OKRs)

Wins:
- Exceeded enterprise customer acquisition target (120%)
- Launched mobile app ahead of schedule (110%)
- Strong team collaboration across functions

Misses:
- Revenue target at 55% (market conditions changed)
- Product quality below target (rushed to launch)
- Engineering hiring at 40% (competitive market)

Key Learnings:
- Need to adjust revenue targets for market reality
- Quality cannot be sacrificed for speed
- Should start hiring process earlier
- Cross-functional collaboration was a strength

Changes for Q4:
- More realistic revenue projections
- Add quality gates to launch process
- Start hiring 6 weeks earlier
- Formalize cross-functional rituals

Step 2: Set Strategic Context

Before setting OKRs, establish the strategic foundation.

Define Strategic Themes

What are the 2-3 big themes for the quarter?

Example Themes:

• Enterprise Market Expansion
• Product Quality and Reliability
• Team Growth and Culture

Clarify What's NOT a Priority

Explicitly state what you're choosing not to focus on.

Example: "This quarter, we are NOT focusing on:

• International expansion (planned for Q2)
• Significant product feature additions (focused on quality)
• Marketing to SMB segment (enterprise focus)"

Identify Constraints

What limitations exist?

• Budget available
• Team capacity
• Technical dependencies
• Market timing
• Regulatory requirements

Step 3: Draft Company OKRs

Company OKRs should reflect your strategic priorities.

Best Practices:

Limit to 3-5 Objectives

More than five dilutes focus.

Make Them Ambitious

Aim for 60-70% achievement on aspirational goals.

Ensure Measurability

Every key result must have a clear metric.

Create Logical Flow

Objectives should work together toward overall strategy.

Example Company OKRs:

Objective 1: Establish leadership in the enterprise OKR market

Key Results:

• Close 25 enterprise deals ($50K+ ACV)
• Achieve 4.9+ rating on G2 for enterprise category
• Generate $2M in enterprise ARR

Objective 2: Deliver a world-class product experience

Key Results:

• Achieve 99.99% uptime (currently 99.5%)
• Reduce P0/P1 bugs from 15 to <3
• Increase NPS from 45 to 60

Objective 3: Build a high-performing, scalable team

Key Results:

• Hire 12 team members across all functions
• Achieve 90+ employee engagement score
• Reduce time-to-productivity from 60 to 30 days

Step 4: Cascade to Team OKRs

Teams create OKRs that support company objectives.

The Cascade Process:

1. Teams Identify Contribution

Each team determines how they support company OKRs.

Example - Engineering Team:

Supporting Company Objective 2 (Product Experience):

• Will focus on reliability and bug reduction
• Will improve deployment processes
• Will implement automated testing

2. Teams Draft Their OKRs

Engineering Team OKR:

Objective: Deliver enterprise-grade reliability and quality

Key Results:

• Achieve 99.99% uptime for all services
• Reduce deployment time from 2 hours to 20 minutes
• Implement automated testing for 90% of codebase
• Reduce production incidents from 20 to <5

3. Verify Alignment

Check that team OKRs ladder up to company OKRs.

Company: Deliver world-class product experience
    → Engineering: Deliver enterprise-grade reliability
    → Product: Improve user experience and usability
    → Design: Create intuitive, accessible interfaces

Step 5: Identify Dependencies

Map out where teams depend on each other.

Dependency Matrix:

Team	Depends On	For What	By When
Sales	Marketing	200 enterprise leads	Ongoing
Sales	Product	Enterprise features shipped	Week 6
Engineering	Design	New UI designs	Week 2
Product	Engineering	API performance improvements	Week 8

Managing Dependencies:

• Make them explicit in OKRs
• Assign owners to coordinate
• Build in buffer time
• Have contingency plans

Step 6: Resource Planning

Ensure you have the resources to execute.

Resource Check:

People:

• Do we have enough team members?
• Do they have the right skills?
• Is anyone overallocated?

Budget:

• Marketing spend available?
• Tools and infrastructure costs?
• Hiring budget?

Time:

• Is the timeline realistic?
• Are there competing priorities?
• Do we need to sequence work?

Example Resource Analysis:

OKR: Close 25 enterprise deals

Required Resources:
- 5 enterprise sales reps (have 3, hiring 2)
- $200K marketing budget (allocated)
- Sales engineering support (need to hire)
- CRM and sales tools (in place)

Resource Gaps:
- 2 sales reps (hiring in Week 2)
- 1 sales engineer (hiring in Week 4)

Risk: Hiring timeline may impact Q1 targets
Mitigation: Accelerate hiring, use consultants if needed

Step 7: Get Team Input

Involve teams in the OKR creation process.

Why Team Input Matters:

• They understand execution details
• Increases buy-in and ownership
• Surfaces issues leadership might miss
• Improves quality of OKRs

How to Get Input:

Individual Contributors:

• Review and comment on draft OKRs
• Share concerns about feasibility
• Suggest alternative key results
• Identify missed dependencies

Team Meetings:

• Present draft OKRs
• Discuss as a team
• Refine together
• Build consensus

Example Feedback Loop:

Draft KR: Reduce deployment time from 2 hours to 20 minutes

Engineer Feedback: "This requires significant infrastructure work that's not in the plan. More realistic target is 45 minutes, or we need to descope other work."

Resolution: Adjusted KR to 45 minutes and documented infrastructure work needed for future quarters.

Step 8: Finalize and Commit

Lock in your OKRs for the quarter.

Finalization Checklist:

• Company OKRs support overall strategy
• Team OKRs ladder up to company OKRs
• All OKRs are measurable and ambitious
• Dependencies are identified and managed
• Resources are allocated
• Team input has been incorporated
• Leadership has approved
• Everyone understands their OKRs

Communication Plan:

All-Hands Kickoff:

• CEO presents company OKRs
• Each team presents their OKRs
• Q&A session
• Celebration to build energy

Written Documentation:

• OKR dashboard updated
• Team pages refreshed
• Individual OKRs documented
• Tracking process confirmed

First Week Activities:

• Team workshops on OKRs
• Individual 1:1s to discuss alignment
• Setup tracking tools
• Schedule check-in meetings

Common Planning Pitfalls

Pitfall 1: Planning Too Late

Starting the week before the quarter begins doesn't allow for thoughtful planning.

Solution: Begin 6 weeks before quarter-end.

Pitfall 2: Top-Down Mandates

Leadership dictates OKRs without team input.

Solution: Create drafts, get feedback, iterate.

Pitfall 3: Disconnected Team OKRs

Teams set OKRs in isolation without alignment.

Solution: Explicit cascade process and dependency mapping.

Pitfall 4: Unrealistic Ambition

Setting targets that require 10x improvement in one quarter.

Solution: Base targets on historical performance and realistic growth.

Pitfall 5: No Resource Planning

Setting ambitious OKRs without allocating resources.

Solution: Resource planning as explicit step in process.

Pitfall 6: Set and Forget

No plan for how OKRs will be tracked and managed.

Solution: Establish tracking rhythm during planning.

Planning for Different Company Stages

Startup (< 20 people)

Characteristics:

• High uncertainty
• Rapid change
• Limited resources

Planning Approach:

• Shorter planning cycles (consider monthly)
• More flexibility to pivot
• Fewer, simpler OKRs
• Informal process acceptable

Example:

• 1 company objective
• 3 key results
• All-hands planning session
• Weekly reviews

Growth Stage (20-100 people)

Characteristics:

• Finding product-market fit
• Scaling team
• Establishing processes

Planning Approach:

• Full quarterly cycle
• Department-level OKRs
• More formal process
• Invest in tools

Example:

• 3-4 company objectives
• Department OKRs that cascade
• 2-week planning process
• Weekly check-ins

Scale Stage (100+ people)

Characteristics:

• Established market position
• Complex organization
• Multiple products/markets

Planning Approach:

• Comprehensive planning process
• Multiple levels of cascade
• Formal governance
• Sophisticated tools

Example:

• 4-5 company objectives
• Division → Department → Team cascade
• 4-week planning process
• Dedicated OKR program manager

Tips for Successful Planning

Tip 1: Make It Collaborative

The best OKRs emerge from conversation, not command.

Tip 2: Ground in Data

Use past performance and market data to inform targets.

Tip 3: Tell Stories

Connect OKRs to company vision and customer impact.

Tip 4: Visualize the Plan

Use roadmaps, Gantt charts, and dependency diagrams.

Tip 5: Build in Flexibility

Leave 20% capacity for unexpected opportunities.

Tip 6: Celebrate the Plan

Make planning energizing, not bureaucratic.

Tip 7: Document Everything

Written plans beat verbal agreements every time.

Tip 8: Start Before You're Ready

Your first quarterly plan won't be perfect. That's okay.

Planning Template

Use this template for your next quarterly planning:

6 Weeks Out

• Leadership strategy session completed
• Company themes identified
• Draft company OKRs created

4 Weeks Out

• Company OKRs finalized
• Resource constraints identified
• Leadership alignment achieved

3 Weeks Out

• Company OKRs communicated to all
• Q&A session held
• Written documentation distributed

2 Weeks Out

• Teams draft their OKRs
• Dependencies mapped
• Initial resource planning complete

1 Week Out

• All OKRs reviewed for alignment
• Resource allocation finalized
• Conflicts resolved
• Final approvals received

Quarter Start

• All-hands kickoff held
• Team workshops conducted
• Tracking setup complete
• First check-in scheduled

Conclusion

Quarterly planning is where the magic happens. It's where strategy becomes actionable, where teams align, and where individuals understand how their work connects to company success.

The process outlined here—starting 6 weeks before quarter-end, involving teams throughout, mapping dependencies, and allocating resources—sets you up for execution success.

Remember these keys to great quarterly planning:

1. Start early (6 weeks before quarter-end)
2. Review and learn from the past
3. Set clear strategic context
4. Limit company OKRs to 3-5
5. Cascade thoughtfully to teams
6. Make dependencies explicit
7. Plan for resources
8. Get team input
9. Communicate thoroughly
10. Kick off with energy

Your quarterly planning process will improve with each cycle. Start with the basics, learn from each quarter, and refine your approach. Within a few quarters, you'll have a planning rhythm that drives real results.

The companies that master quarterly planning create competitive advantage through superior execution. Start building that advantage in your next planning cycle.