A Year Later: Why We Built This Session
Almost a year has passed since we shared our experience running Session #2. Back then, we were excited about ideating milestones and shaping bets collaboratively. But over the following quarters, we hit a common wall—we had great ideas, but not enough shared clarity around how complex they were, what they unlocked, or what they required.
We’ve always believed in collaborative planning. We care about building a product culture where autonomy, creativity, and accountability thrive. And yet, we felt something was missing between ideation and execution.
The truth is: we needed a better way to talk about constraints. We needed a place to slow down, assess our ideas critically, and ask:
- What’s the real cost of this idea?
- What skills are needed to validate it?
- What blocks us?
And so, gradually, we began to shape two new sessions:
- Session #3: to understand complexity and where we could learn faster
- Session #4: to layout a collaborative, visual draft of a quarter, highlighting risk, learning, and collaboration needs
Session #3 became our moment to reality-check the hypotheses we co-created in OKRA.
1. Translating Ideas Into Delivery Reality
By Session #3, your team has drafted OKRs and brainstormed candidate milestones. Now comes the hard but essential work: sizing, qualifying, and de-risking those ideas. This session is where we stop imagining and start grounding.
Every milestone is a bet—but not all bets are equal. Some require coordination. Others are low-hanging fruit. Some have high UX payoff but unclear technical feasibility. Session #3 gives us the shared language and structured time to turn that ambiguity into alignment.
| When to Run | Purpose |
|---|---|
| After Session #2 | Milestones exist but haven’t been sized, scoped, or tested |
| Before Planning Phase | Ensures we’re sequencing based on real constraints |
This session isn’t where you plan your quarter. It’s where you learn what’s actually possible.
2. What the Session Looks Like
We don’t run this session like a spreadsheet. We run it like a collaborative draft board. Here’s the structure:
- Milestone Review – Go one by one. A teammate presents a milestone card and walks through context.
- Effort Estimation – The group sizes the milestone (S/M/L), using heuristics based on prior delivery experience.
- Business & UX Value – Participants score the milestone on business impact ($/$$/$$$) and UX value (♥/♥♥/♥♥♥).
- Dependencies – Team calls out any blocking coordination, e.g. Platform, BI, DS, or external providers.
- Skills Needed – In pairs, identify core skills needed to deliver the milestone (e.g., Design, Frontend, Backend).
# Example layout
okra/
├── session-3/
│ ├── milestone-table.csv
│ ├── effort-size.md
│ ├── value-scores.md
│ └── dependencies-skills.md
No one owns the truth in this session. It’s about surfacing assumptions.
3. Scoring Isn’t About Precision—It’s About Conversation
Don’t waste cycles debating if something is Medium or Large. The goal is shared understanding, not perfect math. Scoring helps your team:
- Balance short bets vs. long-term investments
- Sequence based on value or technical constraints
- Avoid overcommitting by visualizing effort vs. payoff
| Attribute | Scale | Used To… |
|---|---|---|
| Effort | S / M / L | Estimate delivery complexity |
| Business Value | $ / $$ / $$$ | Predict monetization or strategic payoff |
| UX Value | ♥ / ♥♥ / ♥♥♥ | Reflect end-user experience impact |
| Dependencies | Free text | Reveal coordination needs & risks |
| Skills | Free text | Clarify resource needs for planning |
Color coding or emoji isn’t just decoration—it makes patterns pop.
4. Common Pitfalls We’ve Learned to Avoid
We’ve run this session many times. Here’s what breaks it:
- Letting only PMs or Tech Leads estimate — This session is richer when everyone speaks.
- Skipping dependency review — One invisible blocker can break your quarter.
- Not aligning on what S/M/L means — Write it down. Use examples.
- Over-scoring everything as high value — Not everything is top priority. Prioritization needs contrast.
Make this session a safe space to express uncertainty. Estimations are signals—not promises.
5. What You Leave With
By the end, your team will have:
- A complete, team-scored milestone table
- Shared clarity around feasibility, value, and constraints
- Aligned assumptions on what will move the needle
This becomes the foundation for the next phase: building the visual plan and committing to sequencing. In Session #4, you’ll put these cards on the timeline. But this session? It ensures they belong in the deck.
Milestone: Enable smart match recommendations
Effort: M
Business Value: $$
UX Value: ♥♥
Dependencies: Ranking system API, DS support
Skills: Frontend, DS, Product Analytics