Leadership

OKRA Session #4: OKR Quarter Draft Plan

Build a visual, collaborative quarter plan that creates shared alignment without rigid timelines—turning intentions into executable roadmaps

From Alignment to Visualization

After defining our OKRs, shaping milestones, and evaluating effort and dependencies, it’s time to zoom out. Session #4 is where we bring it all together. But not by locking a roadmap. Instead, we build a visual draft—one that reflects how we believe the quarter might unfold based on what we know today.

This isn’t a Gantt chart. This is a conversation canvas. It allows teams to align, anticipate, and adjust. It gives everyone—from engineers to PMs to designers to stakeholders—a shared artifact to reference and challenge as the quarter progresses.

When to RunWhy It Matters
After Session #3You now understand what’s possible and needed
Before sprint prepThis sets up a planning process rooted in context

1. Building a Living Plan

Session #4 is not about committing to hard dates. It’s about mapping intention. Together, the team sequences milestones across a draft timeline:

  • Each milestone includes annotations for effort, value, dependencies, skills needed
  • Teams place cards across weeks, calling out risk areas, constraints, or parallel work needs
  • One person proposes; the rest react—like a fishbowl dynamic
# Folder structure
okra/
├── session-4/
│   ├── quarter-plan-board.png
│   ├── timeline.md
│   └── constraints-risks.md

2. The Flow of the Session

We typically run this session with four key steps:

  1. Each team member picks a milestone, reads it aloud, and proposes where it might land based on earlier sessions.
  2. They annotate effort, dependencies, and skill needs using color or symbols.
  3. Everyone else responds: Are we overlapping too much? Is this sequence risky? Where are we tight on capacity?
  4. Milestones get moved, split, sequenced, or flagged.

3. Outcome: A Shared Plan, Not a Frozen One

You leave the room with:

  • A visual timeline of the quarter with mapped milestone intentions
  • Clear markers for where we might need spikes, research, or alignment
  • A sense of which milestones depend on external unlocks or deep learning cycles
Milestone: Email Feedback MVP
Planned Start: Week 3
Planned End: Week 5
Notes: Depends on DS validation and UX wireframes
Color: Yellow (Experiment), Skills: Design, Backend, DS

4. A Quarter That Reflects How We Work

Session #4 closes the OKRA loop. It helps the team see time and scope as dimensions we manage together—not inputs handed down. We can now:

  • Start sprints with clarity, not surprise
  • Adjust direction without chaos
  • Celebrate learnings and shifts, not just delivery

Most importantly, we have a way to make alignment visible. And in agile work, that’s often what separates good teams from resilient ones.

This isn’t the end of planning. It’s the beginning of a quarter with shared intent.