Planning and Task Management skill 05 of 13
Project Breakdown SKILL.md
The Project Breakdown skill makes Claude, Codex or another AI agent turn any outcome into a plan you can start today. It defines what done looks like, sets scope, picks milestones, breaks them into tasks small enough for one sitting, maps dependencies and owners, estimates with buffer, runs a pre-mortem on risks, schedules the work and names the first next action.
project-breakdown/SKILL.md, version 1.0.0, 1,498 words.
By Afeez Adebayo, Marketing, SEO & Growth Expert with 10+ years of experience.
Created 10 October 2026. Updated 10 October 2026. Free to use under CC BY 4.0.
Big work stalls because it is shaped wrong, not because people are lazy. "Launch the new website" or "write the report" sits on a list for weeks because nobody can start a project; they can only start a next action. Projects also slip because the finish line is vague, dependencies surface late, estimates are optimistic and risks are discovered after they hit. Research on the planning fallacy shows people routinely underestimate how long their own tasks will take. [Research, Kahneman and Tversky; Buehler and colleagues]
This skill turns any outcome into a plan someone can start today: a clear definition of done, milestones, a breakdown into tasks small enough to finish in a sitting, dependencies, owners, realistic estimates with buffer, risks found in advance and the very first next action.
Operating principles
- Define done first. A project without a finish line never finishes.
- Work backwards from the outcome. Milestones, then tasks, then the next action.
- Small enough to start. Every task should take one sitting, roughly two hours or less.
- Make dependencies visible. Know what waits on whom before the plan starts.
- Estimate with buffer. Add time for the unknowns everyone forgets.
Inputs
- The outcome or project name, and why it matters.
- Deadline or target date, and whether it is fixed.
- People involved and their availability.
- Constraints: budget, tools, approvals, other commitments.
- Anything already done or decided.
When to use, and when not to
Use it for any outcome that needs more than one step: launches, reports, events, moves, job searches, courses, renovations or personal projects that keep stalling.
Don't use it for large programmes with many teams, budgets and formal governance (the Product Management category) or for choosing between projects (prioritisation).
Raw SKILL.md file
This is the exact file agents read, including the credit header and licence notice. Save it as project-breakdown/SKILL.md.
--- name: project-breakdown description: "Turn any outcome into a plan someone can start today: a definition of done, scope, milestones, tasks small enough for one sitting, dependencies and owners, estimates with 20 to 30% buffer against the planning fallacy, a pre-mortem, a schedule and the first next action. Use whenever someone has a big project that keeps stalling, needs a project plan, wants to break down a goal or task, has a deadline to plan backwards from or asks where to start." license: CC-BY-4.0 metadata: author: Afeez Adebayo author_url: https://afeezadebayo.com author_linkedin: https://www.linkedin.com/in/afeez-adebayo/ author_x: https://x.com/za_icon source: https://afeezadebayo.com/skills-md/productivity/planning-tasks/project-breakdown/ category: productivity subcategory: planning-tasks version: "1.0.0" created: "2026-10-10" updated: "2026-10-13" --- # Project Breakdown Big work stalls because it is shaped wrong, not because people are lazy. "Launch the new website" or "write the report" sits on a list for weeks because nobody can start a project; they can only start a next action. Projects also slip because the finish line is vague, dependencies surface late, estimates are optimistic and risks are discovered after they hit. Research on the planning fallacy shows people routinely underestimate how long their own tasks will take. [Research, Kahneman and Tversky; Buehler and colleagues] This skill turns any outcome into a plan someone can start today: a clear definition of done, milestones, a breakdown into tasks small enough to finish in a sitting, dependencies, owners, realistic estimates with buffer, risks found in advance and the very first next action. ## Operating principles 1. **Define done first.** A project without a finish line never finishes. 2. **Work backwards from the outcome.** Milestones, then tasks, then the next action. 3. **Small enough to start.** Every task should take one sitting, roughly two hours or less. 4. **Make dependencies visible.** Know what waits on whom before the plan starts. 5. **Estimate with buffer.** Add time for the unknowns everyone forgets. ## Inputs - The outcome or project name, and why it matters. - Deadline or target date, and whether it is fixed. - People involved and their availability. - Constraints: budget, tools, approvals, other commitments. - Anything already done or decided. ## When to use, and when not to Use it for any outcome that needs more than one step: launches, reports, events, moves, job searches, courses, renovations or personal projects that keep stalling. Don't use it for large programmes with many teams, budgets and formal governance (the Product Management category) or for choosing between projects (`prioritisation`). ## Workflow ### Step 1. Write the outcome and definition of done One sentence on the outcome, then three to five checks that prove it is finished. "Website live" becomes: pages published, forms tested, analytics recording, old URLs redirected, team trained. ### Step 2. Set scope What is in, what is out, and what would be nice later. Cutting scope is often the fastest way to hit a date. ### Step 3. Define milestones Three to six checkpoints that each produce something visible, such as "draft approved" or "beta with five users". ### Step 4. Break milestones into tasks Verb-led tasks of two hours or less. Larger tasks are split again. ### Step 5. Map dependencies and owners Which tasks wait on others, which wait on people outside the team, and who owns each task. ### Step 6. Estimate Size each task (small, medium, large or hours), add them up, add 20 to 30% buffer, and compare with the deadline and available hours. ### Step 7. Run a pre-mortem Imagine the project has failed and list why. This technique, described by Gary Klein, surfaces risks people are reluctant to raise. [Reference, Klein] Add a response for the top three risks. ### Step 8. Schedule Place milestones on a calendar, book the first focus blocks and add check-ins. ### Step 9. Name the next action The single first step someone can do today, added to the task list. ## Project plan template ``` # Project: <name> Outcome: <one sentence> Done when: <3 to 5 checks> In scope / Out of scope / Later Milestones: 1. <milestone> | target date | owner Tasks (by milestone): - [ ] <verb-led task> | size | owner | depends on Estimate: <total> + 25% buffer = <total>; fits deadline? yes/no Risks (pre-mortem): <risk> -> <response> Check-ins: weekly in the weekly review Next action: <first step today> ``` ## Splitting large tasks | Too big | Split into | |---|---| | Write the report | Outline sections; gather data for section 1; draft section 1; review with Sam | | Plan the event | Choose three venue options; get quotes; confirm date with speakers | | Learn Python | Install Python; complete lesson 1; write a script to rename files | | Find a new job | Update career profile; set daily job search; tailor CV for first role | ## When the deadline does not fit 1. Cut or defer scope to the Later list. 2. Add people or move other work. 3. Move the date, explaining the trade-off early. Never silently squeeze estimates to make the plan fit. ## Output format ``` 1. Outcome and definition of done 2. Scope: in, out, later 3. Milestones with dates and owners 4. Task list with sizes, owners and dependencies 5. Estimate, buffer and fit with the deadline 6. Pre-mortem risks and responses 7. Schedule and check-ins 8. Next action ``` ## Estimating more accurately - Compare with similar past work rather than imagining the best case. - Ask how long it took last time, not how long it should take. - Estimate in ranges (best, likely, worst) for uncertain tasks and plan on the likely figure plus buffer. - Include reviews, approvals, waiting time and rework, which are easy to forget. - Re-estimate at each milestone with what has been learned. ## Keeping the project moving Check the project in each weekly review: tick finished tasks, confirm the next action, chase dependencies and compare progress with the next milestone. If a milestone slips, decide immediately whether to cut scope, add time or move the date, and tell anyone affected. ## Project file Keep each project in its own file, such as `projects/booking-launch.md`, with the plan template at the top and a short log of decisions and changes below. The agent can then update tasks from meeting notes and prepare status summaries on request. ## Status updates A one-paragraph update works for most audiences: progress against the next milestone, what is done since last time, what is next, risks or help needed, and whether the date still holds. Sending it on a fixed day builds trust and surfaces problems early. Keep updates short; link to the project file for detail. Celebrate finished milestones briefly; momentum keeps long projects alive. ## Edge cases and judgement calls | Situation | What to do | |---|---| | Unclear outcome | Ask what success looks like and who decides | | Many unknowns | Plan the first milestone in detail and the rest roughly; add a research task first | | Waiting on others | Make the request the first task, with a date to chase | | Personal project with no deadline | Set a target date and a weekly slot | | Project keeps stalling | Check the next action is truly small; check it still matters | | Team project | One owner per milestone; share the plan in one document | ## Handoffs to related skills - Choosing which projects to do: `prioritisation` - Task list and next actions: `task-system-setup`, `task-capture-clarify` - Scheduling the work: `time-blocking` - Goals the project serves: `goal-setting-okrs` - Weekly progress: `weekly-review` - Getting started on avoided tasks: `procrastination-unblocking` ## Worked example A small business owner wants to "launch online booking" before a busy season in eight weeks. Done when: booking page live, payments tested, confirmation emails working, staff trained and the old phone process retired. Milestones are tool chosen (week 1), setup complete (week 3), test bookings (week 5), staff trained (week 6) and launch (week 7). The breakdown produces 24 tasks; the estimate with 25% buffer is 38 hours against 40 available. The pre-mortem flags slow payment approval, so applying for the payment account becomes task one. Today's next action: compare three booking tools against a five-point checklist. ## Common mistakes - Starting without a definition of done. - Tasks that are still projects. - Hidden dependencies on other people. - Estimates with no buffer. - No first next action. ## Self-check before you answer - Is done defined with clear checks? - Can every task be finished in one sitting? - Are dependencies, owners and buffer included? - Is there a next action for today? --- Created by Afeez Adebayo, Marketing, SEO & Growth Expert Website: https://afeezadebayo.com LinkedIn: https://www.linkedin.com/in/afeez-adebayo/ X: https://x.com/za_icon Source: https://afeezadebayo.com/skills-md/productivity/planning-tasks/project-breakdown/ Licence: CC BY 4.0 (https://creativecommons.org/licenses/by/4.0/). You may copy, share and adapt this skill, including for commercial use, as long as you credit Afeez Adebayo and link to the source URL above. Keep this notice in any copy or adapted version.
Workflow
Step 1. Write the outcome and definition of done
One sentence on the outcome, then three to five checks that prove it is finished. "Website live" becomes: pages published, forms tested, analytics recording, old URLs redirected, team trained.
Step 2. Set scope
What is in, what is out, and what would be nice later. Cutting scope is often the fastest way to hit a date.
Step 3. Define milestones
Three to six checkpoints that each produce something visible, such as "draft approved" or "beta with five users".
Step 4. Break milestones into tasks
Verb-led tasks of two hours or less. Larger tasks are split again.
Step 5. Map dependencies and owners
Which tasks wait on others, which wait on people outside the team, and who owns each task.
Step 6. Estimate
Size each task (small, medium, large or hours), add them up, add 20 to 30% buffer, and compare with the deadline and available hours.
Step 7. Run a pre-mortem
Imagine the project has failed and list why. This technique, described by Gary Klein, surfaces risks people are reluctant to raise. [Reference, Klein] Add a response for the top three risks.
Step 8. Schedule
Place milestones on a calendar, book the first focus blocks and add check-ins.
Step 9. Name the next action
The single first step someone can do today, added to the task list.
Project plan template
# Project: <name>
Outcome: <one sentence>
Done when: <3 to 5 checks>
In scope / Out of scope / Later
Milestones:
1. <milestone> | target date | owner
Tasks (by milestone):
- [ ] <verb-led task> | size | owner | depends on
Estimate: <total> + 25% buffer = <total>; fits deadline? yes/no
Risks (pre-mortem): <risk> -> <response>
Check-ins: weekly in the weekly review
Next action: <first step today>Splitting large tasks
| Too big | Split into |
|---|---|
| Write the report | Outline sections; gather data for section 1; draft section 1; review with Sam |
| Plan the event | Choose three venue options; get quotes; confirm date with speakers |
| Learn Python | Install Python; complete lesson 1; write a script to rename files |
| Find a new job | Update career profile; set daily job search; tailor CV for first role |
When the deadline does not fit
- Cut or defer scope to the Later list.
- Add people or move other work.
- Move the date, explaining the trade-off early.
Never silently squeeze estimates to make the plan fit.
Output format
1. Outcome and definition of done
2. Scope: in, out, later
3. Milestones with dates and owners
4. Task list with sizes, owners and dependencies
5. Estimate, buffer and fit with the deadline
6. Pre-mortem risks and responses
7. Schedule and check-ins
8. Next actionEstimating more accurately
- Compare with similar past work rather than imagining the best case.
- Ask how long it took last time, not how long it should take.
- Estimate in ranges (best, likely, worst) for uncertain tasks and plan on the likely figure plus buffer.
- Include reviews, approvals, waiting time and rework, which are easy to forget.
- Re-estimate at each milestone with what has been learned.
Keeping the project moving
Check the project in each weekly review: tick finished tasks, confirm the next action, chase dependencies and compare progress with the next milestone. If a milestone slips, decide immediately whether to cut scope, add time or move the date, and tell anyone affected.
Project file
Keep each project in its own file, such as projects/booking-launch.md, with the plan template at the top and a short log of decisions and changes below. The agent can then update tasks from meeting notes and prepare status summaries on request.
Status updates
A one-paragraph update works for most audiences: progress against the next milestone, what is done since last time, what is next, risks or help needed, and whether the date still holds. Sending it on a fixed day builds trust and surfaces problems early.
Keep updates short; link to the project file for detail.
Celebrate finished milestones briefly; momentum keeps long projects alive.
Edge cases and judgement calls
| Situation | What to do |
|---|---|
| Unclear outcome | Ask what success looks like and who decides |
| Many unknowns | Plan the first milestone in detail and the rest roughly; add a research task first |
| Waiting on others | Make the request the first task, with a date to chase |
| Personal project with no deadline | Set a target date and a weekly slot |
| Project keeps stalling | Check the next action is truly small; check it still matters |
| Team project | One owner per milestone; share the plan in one document |
Handoffs to related skills
- Choosing which projects to do:
prioritisation - Task list and next actions:
task-system-setup,task-capture-clarify - Scheduling the work:
time-blocking - Goals the project serves:
goal-setting-okrs - Weekly progress:
weekly-review - Getting started on avoided tasks:
procrastination-unblocking
Worked example
A small business owner wants to "launch online booking" before a busy season in eight weeks. Done when: booking page live, payments tested, confirmation emails working, staff trained and the old phone process retired. Milestones are tool chosen (week 1), setup complete (week 3), test bookings (week 5), staff trained (week 6) and launch (week 7). The breakdown produces 24 tasks; the estimate with 25% buffer is 38 hours against 40 available. The pre-mortem flags slow payment approval, so applying for the payment account becomes task one. Today's next action: compare three booking tools against a five-point checklist.
Common mistakes
- Starting without a definition of done.
- Tasks that are still projects.
- Hidden dependencies on other people.
- Estimates with no buffer.
- No first next action.
Self-check before you answer
- Is done defined with clear checks?
- Can every task be finished in one sitting?
- Are dependencies, owners and buffer included?
- Is there a next action for today?
On this page
- When to use this skill, and when not to
- Example prompts
- Example output
- What the agent needs from you
- How this skill hands off to related skills
- How to run Project Breakdown step by step
- Situations this skill handles
- What makes this skill different
- Practical tips from real projects
- Frequently asked questions
- Changelog
When to use this skill, and when not to
Use it for any outcome that needs more than one step: launches, reports, events, moves, job searches, courses or personal projects that keep stalling.
Big work stalls because nobody can start a project, only a next action. Projects also slip because the finish line is vague, dependencies surface late and estimates ignore the planning fallacy.
Don’t use it for multi-team programmes with formal governance, or for choosing between projects; for that, see prioritisation in the Planning and Task Management skills.
Example prompts
- “Break this project down into steps I can start today.”
- “Plan backwards from a launch in eight weeks.”
- “This project keeps stalling. What is the next action?”
- “Run a pre-mortem on my plan.”
- “Write a one-paragraph status update for my manager.”
Example output
The skill returns a fixed structure. A shortened example for an imaginary site:
Outcome: online booking live before busy season Done when: page live, payments tested, emails working, staff trained, phone process retired Milestones: tool chosen (wk1), setup (wk3), tests (wk5), training (wk6), launch (wk7) Tasks: 24 | Estimate: 38 hours incl. 25% buffer vs 40 available Risk: slow payment approval -> apply first Next action: compare three booking tools against a 5-point checklist
Every plan ends with one next action you can do today, and estimates always include buffer rather than squeezing to fit.
What the agent needs from you
The skill asks for the outcome and why it matters, the deadline and whether it is fixed, the people involved, constraints such as budget and approvals, and anything already done or decided.
How this skill hands off to related skills
Project Breakdown connects to Goal Setting and OKRs, the Weekly Review, Focus and Deep Work and Quarterly Planning and Review, plus prioritisation and task capture in the Planning and Task Management skills.
How to run Project Breakdown step by step
- Install the skill as
project-breakdown/SKILL.md. - Describe the outcome and deadline.
- Agree what done looks like.
- Review milestones and tasks.
- Check the estimate against your time.
- Do the next action today.
Situations this skill handles
Projects vary. The skill handles these:
| Situation | What the skill does |
|---|---|
| Unclear outcome | Asks what success looks like |
| Many unknowns | First milestone detailed, research task first |
| Waiting on others | Request made the first task |
| No deadline | Target date and weekly slot |
| Project keeps stalling | Smaller next action |
| Team project | One owner per milestone |
What makes this skill different
Most project templates list phases. This skill starts with a testable definition of done, keeps every task small enough to start, adds buffer for the planning fallacy and finds risks with a pre-mortem before they hit.
It always ends with the one thing to do today.
Practical tips from real projects
- Define done first.
- Work backwards.
- Small enough to start.
- Estimate with buffer.
A worked example: a small business owner wants online booking before a busy season in eight weeks. Done means the booking page is live, payments are tested, confirmation emails work, staff are trained and the old phone process is retired. Milestones are tool chosen in week one, setup in week three, test bookings in week five, staff training in week six and launch in week seven. The breakdown produces 24 tasks, and the estimate with 25% buffer is 38 hours against 40 available. The pre-mortem flags slow payment approval, so applying for the payment account becomes the first task, and today the owner compares three booking tools against a five-point checklist.
The workflow writes the outcome and three to five done checks, sets scope as in, out and later, defines three to six visible milestones, splits each into verb-led tasks of two hours or less, maps dependencies and owners, sizes tasks and adds buffer, runs a pre-mortem, places milestones and focus blocks in the calendar and names the next action.
Large tasks are split until they fit one sitting. Writing a report becomes outlining sections, gathering data for section one, drafting it and reviewing it with a colleague. Planning an event becomes choosing three venue options, getting quotes and confirming a date with speakers. Finding a new job becomes updating the career profile, setting up a daily job search and tailoring a CV for the first role.
Estimates improve when they use similar past work rather than the best case, use ranges for uncertain tasks, include reviews, approvals, waiting time and rework, and are revisited at each milestone. When the deadline does not fit, the skill cuts or defers scope, adds people or moves other work, or moves the date with the trade-off explained early.
The pre-mortem, a technique described by Gary Klein, asks people to imagine the project has already failed and list the reasons, which surfaces risks people are often reluctant to raise. The top three risks each get a response.
Each project lives in its own file with the plan at the top and a short log of decisions below, so the agent can update tasks from meeting notes. Progress is checked in each weekly review, slipping milestones lead to an immediate decision, and short status updates on a fixed day cover progress, next steps, risks and whether the date still holds.
Edge cases are handled with simple rules. An unclear outcome leads to questions about what success looks like and who decides. A project with many unknowns gets a detailed first milestone, a rough outline for the rest and a research task at the start. When work depends on other people, the request becomes the first task with a date to chase. Personal projects without deadlines get a target date and a weekly slot, and stalled projects get a smaller next action and a check that they still matter.
Frequently asked questions
How do I break down a big project?
Define done, set scope, choose three to six milestones, split each into tasks of two hours or less, map dependencies and name the first next action.
How small should tasks be?
Small enough to finish in one sitting, roughly two hours or less.
How much buffer should I add?
Usually 20 to 30%, because people underestimate how long their own tasks take.
What is a pre-mortem?
Imagining the project has failed and listing why, so risks are found and handled early.
What if the deadline does not fit?
Cut scope, add people or move the date openly; never silently squeeze estimates.
Can the agent keep the plan updated?
Yes. With a project file, it updates tasks from meeting notes and drafts status updates.
Changelog
- 1.0.0, 10 October 2026: first release.
Use, adapt and share this skill under CC BY 4.0: credit Afeez Adebayo and link to this page.
