Home
cd ../playbooks
Project ManagementAdvanced

Wayfinder: Decision-Ticket Planning for Oversized Efforts

Plan work too big for one agent session as a shared map of decision tickets — questions to resolve, not slices of a build to execute — and work through them one at a time until the way to the destination is clear.

10 minutes
By Matt PocockSource
#planning#project-management#decision-tracking#issue-tracker#scoping#large-projects

A huge, foggy effort doesn't fail because nobody could code it — it fails because nobody could hold the whole shape of it in one session, so the plan drifts, decisions get made twice, and nobody can tell what's actually settled versus still open.

Who it's for: engineering leads scoping multi-session efforts, teams planning a spec or major migration before implementation starts, solo developers who lose track of open decisions across long-running projects, anyone whose planning currently lives in scattered chat threads instead of a single source of truth

Example

"Chart a map for redesigning our auth system" → A named destination (the target auth architecture spec), a breadth-first frontier of decision tickets (which provider, how sessions migrate, what breaks for existing users), research tickets fired off in parallel, and a living map that tracks exactly which decisions are settled and which are still fog — worked one ticket per session until the way is clear

CLAUDE.md Template

New here? 3-minute setup guide → | Already set up? Copy the template below.

# Wayfinder — Decision-Ticket Planning for Oversized Efforts

A loose idea has arrived that's too big for one agent session, wrapped in fog: the way from here to the **destination** isn't visible yet. Wayfinding charts that way as a **shared map** of **decision tickets** — questions whose resolution is a decision, not slices of a build to execute — then works them one at a time until the route is clear.

The destination varies per effort: a spec to hand off and iterate on, a decision to lock before planning starts, or a change made in place (a data-structure migration, say). The map is domain-agnostic — engineering work, course content, whatever fits the shape.

## Plan, Don't Do

Wayfinder is **planning** by default: each ticket resolves a decision, and the map is done when the way is clear — nothing left to decide before someone goes and does the thing. The pull to just do the work is usually the signal you've reached the edge of the map and it's time to hand off. You can override this for a given effort by noting in its Notes that execution belongs inside the map itself; absent that, produce decisions, not deliverables.

## Refer by Name

Get new playbooks like this one

One email a week with new Claude Code workflows. Free, like everything here.

No spam. Unsubscribe anytime.

README.md

What This Does

Wayfinder charts oversized, foggy efforts as a shared map of decision tickets on your issue tracker — questions whose resolution is a decision, not a slice of a build to execute. It names a destination first (the spec, decision, or change the effort is finding its way to), fans out breadth-first across the open decisions, and creates tickets only for questions sharp enough to state precisely now, leaving everything else in a deliberately incomplete "fog of war" that graduates one patch at a time as earlier tickets resolve.

The discipline that makes it work: plan, don't do. Each ticket resolves exactly one decision, the map is done when nothing's left to decide, and no session resolves more than one ticket (research tickets excepted) — so scope never quietly balloons into execution and no single sitting tries to hold the whole effort in its head.


Quick Start

Step 1: Create a Project Folder

mkdir wayfinder-map && cd wayfinder-map

Step 2: Download the Template

Click Download above, then:

mv ~/Downloads/CLAUDE.md ./

Step 3: Chart Your First Map

claude

Then describe the oversized, foggy idea you need to plan. Claude will name the destination, map the frontier of decisions, and create the map plus its first batch of tickets.


Tips & Best Practices

  • The destination line is the single highest-leverage sentence on the whole map — get it right before creating a single ticket, since every later "is this in scope" call traces back to it.
  • Keep ticket questions genuinely decision-shaped. "Implement the login form" is a task wearing a ticket's clothes; "Which auth provider do we standardize on?" is a real ticket.
  • Use your tracker's native blocking/dependency feature if it has one — it renders the frontier visually, so anyone can see what's takeable without opening the map itself.
  • Resist resolving two tickets in one sitting even when the second feels quick. The one-ticket-per-session rule is what keeps each resolution properly scoped, not a formality to skip under time pressure.

Limitations

  • Built for genuinely oversized efforts — a task small enough to finish in one sitting doesn't need a map; skip straight to doing it.
  • Without a tracker that supports native child-issues and blocking, the fallback (local markdown files) works but loses the visual frontier a real tracker's UI gives for free.
  • The map is only as good as its destination. A vague or drifting destination produces a map that never converges — revisit and sharpen it explicitly if tickets start feeling arbitrary.

$Related Playbooks

Project Management

Trello Board Automation

Automate Trello board management, card workflows, power-ups, and team collaboration

10 minutes
Advanced
Project Management

Project Charter & Kickoff Documentation

Create project charters with scope definition, stakeholder analysis, risk assessment, and kickoff materials for new initiatives.

5 minutes
Beginner
Project Management

Project Status & Health Reporting

Generate project health dashboards with RAG status, milestone tracking, risk updates, and stakeholder-ready summaries.

5 minutes
Beginner
Project Management

Requirements Documentation

Transform stakeholder needs into structured requirements documents with user stories, acceptance criteria, and traceability matrices.

10 minutes
Intermediate
Project Management

Sprint Planning & Backlog Refinement

Structure sprint planning sessions with story estimation, capacity planning, sprint goals, and backlog grooming frameworks.

10 minutes
Intermediate
Project Management

Stakeholder Analysis & Communication Planning

Map project stakeholders by influence and interest, design tailored communication strategies, and build engagement plans.

5 minutes
Beginner
Project Management

Project Management Bootstrapper

Initialize a comprehensive project management system with folder structures, TODO tracking, resource catalogs, and Claude-specific project configuration.

15 minutes
Intermediate
Project Management

Team Capacity & Resource Planner

Analyze team workload, identify capacity gaps, and model resource allocation scenarios for staffing decisions.

15 minutes
Intermediate
Project Management

Product Feature Prioritization

Prioritize product features using RICE, weighted scoring, and value-vs-effort frameworks with stakeholder alignment.

10 minutes
Intermediate
Project Management

Lessons Learned Documentation

Facilitate and document project retrospectives with structured lessons learned, root causes, and actionable improvements.

5 minutes
Beginner
Project Management

Product Roadmap Communication

Transform product roadmaps into audience-specific communications for executives, customers, sales teams, and engineering.

5 minutes
Beginner
Project Management

Weekly Project Review

Automate comprehensive weekly project summaries by synthesizing WhatsApp, email, and meeting transcript data into a living dashboard and detailed activity log.

30 minutes
Advanced

Browse all Project Management playbooks →