Brainstorming and Outlining with AI

The Hardest Part: Getting Started

The blank page is terrifying. AI can fill it with ideas, structure, and starting points—so you spend your time choosing and refining instead of staring.

Idea Generation from Scratch

When you have nothing:

Broad topic brainstorming:

Give me 20 article ideas about [general topic] for [audience]

What are 10 interesting angles on [subject]?

What topics in [field] are people searching for right now?

Niche down:
Start broad, then narrow:

You:

Give me article ideas about productivity

AI lists 15 ideas.

You:

Expand on #7 (productivity for remote workers). Give me 10 specific article angles.

Use constraints:

Give me 10 blog post ideas about [topic] that:

• Target beginners
• Can be written in under 1000 words
• Include actionable advice
• Haven't been done to death

When You Have a Vague Idea

Turn fuzzy thoughts into concrete topics:

You:

I want to write something about how AI is changing work but I'm not sure the angle

AI:

Here are 10 angles:

1. How to AI-proof your career
2. Jobs AI will create in the next 5 years
3. Using AI tools at work without getting replaced
4. Skills that matter more because of AI
   [etc.]

Audience-specific angles:

I want to write about budgeting. Give me 5 angles for college students, 5 for new parents, and 5 for people near retirement.

Organize Random Thoughts

Problem: You have notes, thoughts, and ideas scattered everywhere.

Solution: Dump them into AI and ask for structure.

Prompt:

I have these random thoughts about [topic]: [paste all your notes, bullet points, random ideas]. Organize these into a logical structure for an article/presentation/report.

AI will:

• Group related ideas
• Suggest a logical flow
• Identify gaps
• Propose an outline

Example:

Your messy notes:

- remote work saves commute time
- harder to separate work/life
- some people miss office social
- productivity studies mixed
- tech tools make it possible
- not all jobs can be remote

AI output:

Proposed outline:
1. Introduction: The Remote Work Shift
2. Benefits of Remote Work
   - Time savings (commute)
   - Flexibility
3. Challenges
   - Work-life boundaries
   - Social isolation
   - Not suitable for all roles
4. The Technology Enabling It
5. What the Research Shows (productivity)
6. Conclusion: Is Remote Work Right for You?

Now you have structure instead of chaos.

Creating Outlines

Simple outline:

Create an outline for a 1000-word article about [topic] for [audience]

Detailed outline:

Create a detailed outline for [content type] about [topic]. For each section, include:

• Main point
• 2-3 sub-points
• Suggested examples or data points

Specific structure:

Create an outline using the problem-solution-results structure for [topic]

Create an outline using the hero's journey structure for [story]

Outline Refinement

Start basic, then enhance:

Step 1: Get basic outline

Outline for article about [topic]

Step 2: Expand sections

Expand section 3 of this outline with more detail: [paste outline]

Step 3: Add elements

Add 3 real-world examples to this outline: [paste outline]

Add data points I should research for each section: [paste outline]

Step 4: Reorder if needed

Does this outline flow logically? Suggest a better order if needed: [paste outline]

Different Content Types

Blog post outline:

Create a blog post outline about [topic] including:

• Attention-grabbing intro
• 4-5 main points with subpoints
• Practical examples for each
• Actionable conclusion

Presentation outline:

Create a 20-minute presentation outline about [topic] for [audience]. Include timing estimates for each section.

Report outline:

Create a business report outline about [topic] with:

• Executive summary
• Background/context
• Analysis sections
• Recommendations
• Appendix items

Video script outline:

Create a 10-minute YouTube video outline about [topic]. Include:

• Hook (first 30 seconds)
• Main content sections
• Call to action

Email series outline:

Create an outline for a 5-email onboarding series for [product/service]. Each email should build on the last.

Brainstorming Specific Elements

Headlines/titles:

Give me 20 headline options for an article about [topic]

Rewrite this headline 10 ways to make it more clickable: [headline]

Opening hooks:

Give me 5 opening sentences for an article about [topic] that grab attention immediately

Examples to illustrate a point:

I'm writing about [concept]. Give me 5 concrete examples that illustrate this for [audience]

Analogies/metaphors:

What's a good analogy to explain [complex concept] to [non-expert audience]?

Counterarguments:

I'm arguing that [position]. What are the strongest counterarguments I should address?

Transitions:

I just covered [topic A] and I'm moving to [topic B]. Give me 3 transition sentences.

Research Questions

Identify knowledge gaps:

I'm writing about [topic]. What questions should I research before writing?

What data or statistics would strengthen this outline: [paste outline]

Find interesting angles:

What's surprising or counterintuitive about [topic]?

What common myths about [topic] should I debunk?

Collaborative Brainstorming

Build on AI's ideas:

You:

Give me 10 article ideas about AI

AI lists them.

You:

I like #3 and #7. Combine them into one article concept.

AI combines them.

You:

Now create an outline for that combined concept.

Diverge then converge:

1. Generate many ideas (diverge)
2. Pick the best (converge)
3. Develop the chosen one (dive deep)

Unsticking Stuck Thinking

When you know what you want to say but can't organize it:

Here's what I want to communicate: [brain dump everything]. Structure this into a logical outline.

When you have writer's block on structure:

I'm stuck organizing my thoughts about [topic]. Ask me 5 questions that would help me clarify my structure.

When you're overthinking:

I'm overthinking this article about [topic]. Give me the simplest possible outline.

Advanced Brainstorming Techniques

SCAMPER prompts:

Apply SCAMPER to this idea: [your idea]

• Substitute: What could I replace?
• Combine: What could I merge?
• Adapt: What could I adapt from elsewhere?
• Modify: What could I change?
• Put to other uses: How else could this be used?
• Eliminate: What could I remove?
• Reverse: What if I did the opposite?

Six thinking hats:

Analyze this idea using six thinking hats: [your idea]

• Facts (white hat)
• Emotions (red hat)
• Negatives (black hat)
• Positives (yellow hat)
• Creativity (green hat)
• Organization (blue hat)

First principles:

Break down [topic] to first principles. What are the fundamental truths? Build up from there.

Content Calendar Planning

Generate content themes:

Create a 3-month content calendar for [topic/brand]. Include 2 posts per week, varying formats and themes.

Topic clustering:

I want to create a content cluster around [pillar topic]. Give me:

• 1 pillar article (comprehensive)
• 10 supporting articles (specific subtopics)
• How they link together

Turning Outlines into Content

Once you have an outline:

Option 1: Write it yourself
(Outline removes the hard part—deciding what to say. Writing is easier.)

Option 2: Have AI draft section by section

Using this outline: [paste], write a detailed introduction (300 words)

Then move to next section, etc.

Option 3: Hybrid

• Write sections you know well yourself
• Have AI draft sections you need help with
• Edit everything to sound like you

Real-World Examples

Example 1: Article idea to outline
You:

I want to write about saving money

AI:

20 article ideas about saving money

You:

Expand on #5 (saving money as a freelancer)

AI:

10 specific angles on freelancer finances

You:

Create an outline for "5 Money Mistakes Freelancers Make (And How to Fix Them)"

AI:

Detailed outline with intro, 5 mistakes, solutions, conclusion

Example 2: Random notes to structure
You dump 2 pages of meeting notes into AI:

Organize these notes into a project proposal outline

AI creates:

• Executive summary
• Problem statement
• Proposed solution
• Timeline
• Budget
• Expected outcomes

Example 3: Content series
You:

Create a 4-part beginner guide outline for [topic]

AI outlines:

• Part 1: Basics
• Part 2: Getting started
• Part 3: Common mistakes
• Part 4: Next steps

Practice Exercises

Exercise 1: Idea explosion

1. Pick a broad topic
2. Ask AI for 20 article ideas
3. Choose your favorite 3
4. Have AI create outlines for each
5. Pick the best

Time: 5 minutes. Result: 3 article outlines.

Exercise 2: Notes to outline

1. Dump your random thoughts on a topic (messy is fine)
2. Have AI organize them
3. Refine the outline
4. Identify what's missing

Exercise 3: Multi-format
Take one topic.
Have AI create:

• Blog post outline
• Video script outline
• Social media post series outline
• Email outline

Notice how structure changes per format.

Exercise 4: Unstick yourself
Next time you're stuck:

1. Dump everything in your head to AI
2. Ask it to organize
3. Start writing from the outline

Tips for Better Brainstorming with AI

Be specific about audience:
"Ideas for article" → generic
"Ideas for beginners struggling with [specific problem]" → targeted

Give context:
"I'm a [role] writing for [audience] about [topic]"
Better results.

Iterate, don't accept first draft:

• First pass: Get ideas
• Second pass: Refine best ones
• Third pass: Develop chosen idea

Combine human + AI thinking:

• AI generates options
• You evaluate and choose
• AI expands your choice
• You customize and finalize

Save good outlines:
When AI creates a great outline structure, save it as a template for future similar content.