A note from the author, Mark Levy: I wrote this guide (I believe) in about 2010. In the age of AI, I find its method for generating original ideas more critical than ever. Here it is, lightly edited for today.

This list-making guide is a method for mining your own mind for experiences and insights that exist only there. These are the unique stories, forgotten connections, and nascent hypotheses that have not yet found their way into the world. Because they don’t exist on the internet, they cannot be found or replicated by generative AI.

This is why a manual, systematic ideation technique remains not just relevant, but essential for any thought leader. It is a process for unearthing the very raw material that will differentiate your work. What follows is the original guide. It’s a timeless method for looking at a topic from so many different angles that it becomes foreign to you, forcing you to see it anew and generate foundational ideas.

The Original Text: List-Making As a Tool of Thought Leadership

As a thought leader, you’re hired for your ideas. In a sense, your ideas are your inventory. They’re your currency. Bluntly stated: Your ideas equal money.

The right ideas form the basis of your consulting engagements, media appearances, books, articles, posts, and speeches. Your ideas get you noticed in the marketplace, help you command enviable fees, and enable you to do good work on projects of significance.

When your career is predicated on ideas, however, a complication arises: You cannot endlessly promote the same ideas. One reason is that, as the world changes, the effectiveness of your ideas can erode. A second reason is that the marketplace habituates to your ideas. Prospects think they know what you’re going to suggest, so they turn to other people who tout mystery strategies holding greater promise.

As a thought leader, it’s important that you refine or even restock your ideas periodically, so your brand stays distinct, you stay sought-after, and your business practice stays lucrative.

How, though, do you create standout ideas and intellectual property to add to your business? The ideation technique I’ve used with clients is one you’ve likely used all your life: list-making.

A list constructively narrows your focus. It’s a lens that forces you to ignore most of the world, so you can examine and make decisions about an isolated sliver. A list also coaxes unarticulated and half-remembered information from your brain, so you can better see, understand, and act upon the information.

As useful as list-making has been as a gathering-and-prioritizing device, its worth is amplified when you use it as a tool to produce insights and ideas.

List-Making for Ideation in a Nutshell

Next time you need new ideas, first consider your topic by making a list. Don’t make just one lone random list, though. No single list could give you a suitable view.

You want to look at your topic in a way that’s broad and, in a sense, disorienting. You want your topic to seem foreign to you, so as you study it, surprises, insights, and novel ideas emerge without much effort.

Instead of one list, create five-to-fifteen lists – each with its own focus. These lists would have names like, “What facts come to mind about the topic?,” “What stories come to mind about the topic?,” and “In what ways can I reframe the topic?”

Spread the lists out on a table, look from list to list and item to item, and ask yourself questions, like “What’s obvious here?” and “What’s surprising?”

Human beings are meaning-making machines. In a matter of moments, you’ll find yourself making unexpected connections and seeing unpredicted patterns. New meaning will appear to you, because of the curious vantage point afforded by the lists. You can then turn your latest ideas into “thought chunks,” which you can expand into products and services that support your thought leadership.

That was the nutshell version. Here is the same technique told in detail:

List-Making for Ideation in Detail

Step #1: Brainstorm a Master List

When you need fresh ideas on a topic, start by making an initial list. What type? A list of lists. You’re going to brainstorm the title of every list you could possibly make about your topic. Let’s call the paper you record these titles on your master list.

Some of the titles on your master list might sound generic, like you could use them to study virtually any topic:

  • What do I know about (this topic)?
  • What don’t I know about it?
  • What are all the pieces I could divide it into?
  • How can I reframe it?
  • What are my assumptions about it?
  • What are some facts?
  • What stories about it come to mind?
  • What images?
  • What metaphors and analogies?
  • What successes have I had in my work on it?
  • What mistakes have I made?
  • What excites me about it?
  • What scares me?
  • Who are the experts on this topic?

Other titles on your master list will be topic-dependent. For instance, if your topic is organizational culture change, some of the titles you could put on your master list include:

  • How would an organization know if its culture is changing?
  • Why do some culture changes succeed?
  • What must an organization give up to change its culture?
  • How do you measure the value of a culture change?
  • What organizations have I worked with that have had a great culture?

In making your master list, don’t over-think it. Take a few minutes and jot down as many titles as you can, as fast as you can. When you’ve listed thirty titles or so, stop.

Step #2: Explore Your Topic Through Multiple Lists

Look over your master list, and pick a handful of lists you’d like to write. Maybe five, ten, or fifteen different ones. How do you know which titles to select? If an entry feels boring or unnecessary, pass it by. If an entry seems valuable, even if it’s for reasons you can’t explain, choose it. Your gut has its reasons.

Write the title of each chosen list at the top of its own page, and fill in those lists. You can fill in each list one at a time, or you can haphazardly jump back and forth among lists, jotting down items as they occur to you.

Step #3: Make Meaning From Your Fresh Vantage Point

Once you’ve finished filling in the lists, spread them on a table, shuffle them around, and look from list to list and item to item. Ask yourself questions about what you see. Questions like:

  • What’s obvious?
  • What haven’t I noticed before?
  • What’s right? What’s wrong? What’s missing?
  • What’s surprising?
  • What’s useful?
  • What patterns do I see?
  • What’s this all adding up to?

By giving your lists time, attention, and curiosity, you’ll see your topic from a perspective that’s wide and uncommon. It’ll be like the first time you saw your hometown from the air. You’ll make fresh meaning from what you’re observing. You’ll notice connections between lists, spot associations among items, discover patterns, build hypotheses, recall stories, and formulate ideas.

While studying your lists, write down your thoughts on a pad as they hit you. Don’t limit yourself to notions elegant or weighty. Get everything down.

Step #4: Build an Inventory of New Thoughts

To finish your list-making ideation session, you need to convert your fragmentary notes into what I call, thought chunks. Doing so will give you a better handle on the ideas, and will help you store them for later use.

What is a thought chunk? It’s a piece of prose containing a complete thought. That prose piece may be a sentence or two or three long. It may even stretch into a couple of pages. Its length isn’t critical. What is important is this: If you read one of your thought chunks – even ten years from now – you’d understand what it meant instantly.

A chunk, then, is a time capsule you create for the future you.

For example, I was once working on ideas for elevator speeches. I scribbled the note “Talking about a movie.” Later, I expanded this into a full thought chunk:

“When looking for distinctions that would fit an elevator speech, most people freeze up. They think finding distinctions is a special skill. It’s not. Finding distinctions is no harder than talking about a movie. If a friend asked about a movie you’d recently seen, you wouldn’t hesitate until you found the perfect thing to say. Instead, you’d instinctively head for something distinctive: ‘It’s about a robot that travels back in time to protect its inventor,’ or ‘It’s the new Daniel Day-Lewis film.’ Finding engaging business facts to talk about in your business elevator speech is no different. It comes naturally if you let it.”

I’ve now captured that idea as a standalone thought chunk. Its meaning is clear and will remain so. I could use the idea now, or a decade from now. It’ll always be at the ready.

Finish your ideation session by converting all your ideas into chunks to store on your computer. You’re building an inventory of fresh ideas, observations, and stories.

Additional Notes from the Original

  • Time: A quick session can be done in under an hour. A deeper dive might take three hours, perhaps broken up over several days.
  • Revisit: Come back to your lists days or weeks later. Your fresh eyes will see a dozen connections that eluded you the first time.
  • Group Work: This process can be adapted for group brainstorming. The group jointly follows the list-making process to solve one member’s problem.
  • Organization: Once I’ve written up a thought chunk, I drop it into a separate document on my computer which holds similarly-themed chunks (e.g., “Positioning,” “Sales,” “Writing Technique”). This is far more effective than having ideas scattered across your hard drive. By saving and organizing chunks as you go, you’re tending your lawn regularly so it’s always thick and green.

Modernizing the Method: Tips for Today

The core of this technique is timeless, but the tools we use can make it even more powerful.

Use AI as a Brainstorming Partner. Stuck on your master list? Ask an AI assistant: “I’m trying to generate new ideas about [your topic]. What are 20 different lists I could make to explore this topic from unusual angles?” Use its suggestions as a starting point.

Create a Digital “Thought Chunk” Database. Instead of Word documents, use modern tools like Notion, Obsidian, or Roam Research. These allow you to tag, link, and instantly search your entire inventory of ideas. A simple tag like #thoughtchunk can make them all instantly accessible.

Use Voice-to-Text. Ideas often come at inconvenient times. Use a voice memo app on your phone to capture fleeting thoughts and raw ideas for your lists. You can transcribe them later, ensuring nothing gets lost.

Apply it to Social Media. This technique is perfect for generating a month’s worth of content. The items on your lists can become individual tweets. The connections between items can become LinkedIn posts. A fully developed thought chunk can become a thread or a short article.

Let AI Be Your Editor. Once you have a raw, powerful thought chunk born from your own experience, you can use AI to help refine it. Ask it to “clean up this prose,” “suggest three different headlines for this idea,” or “expand this into a short blog post, keeping the core message intact.”

Getting Started Today

Ready to try? Here’s a simplified guide.

First, Pick a Topic. Choose a subject you want to explore or a problem you need to solve.

Next, Brainstorm Your Master List. Spend 10 minutes writing down the titles of every possible list you could make about your topic. Don’t judge, just write.

Then, Choose and Create. Pick the 5-10 most interesting list titles and spend 20-30 minutes filling them out. Jump between them as ideas strike.

After that, Connect and Capture. Spread your lists out (digitally or physically). Look for patterns, surprises, and connections. Ask, “What’s the interesting thing here?” and write down your emerging ideas.

Finally, Create Your Thought Chunks. Take your best 3-5 ideas and write each one out as a complete “thought chunk.” Give it a clear title and save it in your new idea inventory.

In a world of content abundance, the new thought leadership is not about creating more content, but about creating different content. It’s about depth, originality, and a unique point of view. This method is a reliable engine for producing exactly that.