Day 1c · The Importance of Requirements
Plan Mode
& Milestones
The most important skill when working with AI isn't prompting. It's knowing what you want before you start.
20 min + live demo
Kyle
plan mode · milestones · drift · verification
The Problem
This feels productive
You
Build me a landing page
Claude
Done! Here's your landing page.
You
Make the header blue
Claude
Updated to blue.
You
Darker blue
Claude
Done.
This continues for
another 45 minutes.
No defined goal — each response feels like progress. It isn't.
19%
slower when using AI assistants —
while believing they were faster
"Rachel Thomas calls this 'dark flow' — an addictive, non-productive state, like gambling."
Rachel Thomas, co-founder of fast.ai · Forbes "20 Most Incredible Women in AI"
fast.ai, Jan 2026 ↗
Defining "done"
What you used to tell Claude
"Make me a project management app."
What you tell Claude now
"I want to build a project tracker that lets me…"
- ·Drag and drop tasks across workflow stages in a Gantt-style timeline
- ·Click a task to mark complete or flag dependencies
- ·Expand a task to see referenced files, subtasks, and subitems
- ·Support multiple projects with separate boards
- ·Persist data locally — storage, infrastructure, offline access
Wandering vs. Iterating
Wandering
- ·No defined goal
- ·Each change is a coin flip
- ·45 min of "darker blue"
- ·Feels productive, isn't
Iterating
- ·Target defined upfront
- ·Each change moves toward it
- ·Push back on the plan itself
- ·Slower start, faster finish
The Solution
Plan Mode
Think together before it acts
Claude Code
Shift+Tab
press twice — or type /plan
Locks Claude to read-only.
Can explore, cannot change.
Claude Desktop
"Let's plan this before building anything"
Be explicit — it will jump ahead otherwise.
How it works
1
You provide contextWho it's for, constraints, tools, preferences — everything
2
Claude proposes milestonesBased on your context — phases with dependencies and decision points
3
You push back"Add this." "Remove that." "You're overcomplicating this." This is where value is created.
4
Written to a filemilestones.md — persists beyond the conversation
The more context you give upfront, the better the milestones.
The push back
is the skill
"Once the plan is good, the code is good."
Write it to a file
Ask Claude to create a milestone document. Look for milestones.md in your project.
Conversation
- ·Disappears when session ends
- ·Gets compressed in long chats
- ·Can't be re-read later
- ·Only one of you remembers it
milestones.md
- ·Persists across sessions
- ·Claude can re-read anytime
- ·You can review & edit it
- ·Single source of truth
02 · Staying on track
Recognizing
drift
When to stop and reset
Signs you've drifted
⚠️
Claude keeps saying "You're absolutely right"It's reflecting your input back, not collaborating.
📋
5+ one-off requests not in the original planYou're wandering, not iterating.
🔄
Fixing things the last fix brokeWhack-a-mole means you've lost the thread.
❓
You can't remember the original goalIf you can't articulate it, you've drifted.
When you spot drift
1
Stop.Don't send another message.
2
Re-read the milestones file.Is this in the plan?
3
If the plan needs to change— go back to plan mode and update it first.
4
If you just wandered— start fresh. Point Claude at the file.
Coming this afternoon
Why drift happens:
AI has limited memory
Long conversations get compressed. Early details get fuzzy. Claude may lose track of decisions you made at the start.
That milestones file isn't just organization — it's a lifeline Claude can re-read when its memory fades.
03 · Closing the loop
Make AI check
its own work
Three prompts that work
After building
"Review what you just built against milestone 1. What's missing?"
Before moving on
"Check each acceptance criterion. Which ones pass?"
When something's off
"Pretend you're QA. Test this against the requirements."
Why this works: milestones with clear "done" criteria give Claude something concrete to check against. Without that, asking it to verify is meaningless — verify against what?
Your superpower
The rigor doesn't
disappear
"The rigor that used to live in coding doesn't disappear — it moves elsewhere."
It moves to requirements and decisions.
That's you.
Live demo
Let's build
something
Campaign Management Board — live, using this process
01 Plan mode — describe what we're building
02 Claude proposes milestones
03 I push back
04 Build milestone 1
05 Verify against milestones