Issue Planner · Case study

From backlog to executable plan

Human-in-the-loop AI planning that turns a vague issue into a repo-correct, PR-sized plan a person can trust.

Role
Lead Product Designer
Timeline
One quarter, to GA design
Team
1 PM, platform & applied-AI eng
Add SSO (SAML) to admin console v4 ▾

The challenge

Most wasted effort is decided before the first commit.

The gap between an accepted issue and the first line of code is where scope creep, rework, and stalled tickets collect. Three problems sat underneath it.

Tap a point on the path to see each one.

IssueFirst commit

My role

I led the design end to end.

A capable planning pipeline already existed. My work was the experience on top of it, and the way we'd know it worked.

Toggle to see what I owned versus where I partnered.

Problem framing & JTBD Information architecture Every screen & state The trust model Measurement plan Scope (PM) Pipeline limits (platform) Model uncertainty (applied-AI)

Strategy

A product line, not a feature.

Reviewing code is downstream; we arrive once work is half done. Planning moves the product upstream, to where work is shaped.

Switch the surface to see what changes.

Discovery

One job, three people who need it.

“A plan good enough to start from, without the work of writing it.” It read differently for each.

The design

Five decisions, one rule: the person decides.

The AI drafts a full plan, but the default action is review. Edit in place, replan in chat, revert without risk, hand off cleanly.

Try the tabs.

v5Merged phases 1 + 2 (chat)
v4Confirmed Okta assumption
v3Added rollout flag phase
v2Repo target → +auth-svc
v1Initial generation

Package the plan into your environment.

Measurement

One metric that is hard to fake.

The north star sits at the end of the loop: plans that become a merged PR, linked back to the issue. Beneath it, a funnel shows where plans drop off.

Hover a stage. The dashed one is the part worth instrumenting.

Plan generated100
Viewed82
Worked on (edits, assumptions)61
Handoff completed44
First PR opened37
Merged PR · north star29

Reflection

What I would carry forward.

The decisions that mattered were about doubt and control, not layout.

Human-in-the-loop AITrust designInformation architectureComplex state designOutcome-driven measurementCross-functional leadership

The trust model is the design

For AI products, when the system admits doubt and who holds the decision matter more than layout.

Editing beats re-prompting

The moment someone argues with the model to fix one line, they are gone.

A plan you can't run is a demo

The handoff, and the link back to the PR, is what changed how work got done.

Scroll