Working in Reverse - Creative Ways to Use Classic Writing Tools


Writing is not a linear process with a specific set of tools that a writer must use to succeed. For many, it’s a messy, disjointed puzzle where the missing pieces are not found until the very end of the process.

The goal of writing is to capture and present your thoughts so others can derive value from your thinking; you can take several paths to get there. This article is your permission to try something different.

Here’s how to get new value from some classic tools.

1. Use checklists at the beginning of your writing to avoid weak areas.

Most people think of checklists as a series of things to confirm after you’ve completed a task. But checklists can be used in many ways. Consider reviewing your checklist before starting a writing assignment. Reviewing a checklist (or rubric) can bring issues to front of mind and help prevent repeating mistakes you’re prone to make on autopilot.

Why Use a Checklist?

Checklists help capture the value of your experience in solving complex problems and build on those experiences—without forgetting steps along the way. This is particularly important for routine and mundane tasks that can blur in your mind—like proofreading, editing, or formatting citations.

How a Pre-Writing Checklist Helps

A pre-writing checklist primes you to break your habits and act intentionally. When you review your checklist, visualize proper writing techniques and rules you should follow. This review + visualization method helps you achieve clearer focus. Visualization brings nearly the same benefits as having actually practiced the writing techniques themselves. And by preparing yourself to write, you create a map for your mind to follow.

Make Your Own Checklist

Make a checklist of things you’d like to remember and techniques you’d like to employ in your writing. Each rule should be an affirmative statement of something you will do—not a list of don’ts. When you use positive, affirmative language in your checklist, reviewing your list will naturally lead to visualizing yourself accomplishing the task.

Here’s how to do it:

  • Think about your weaknesses and include them on your list
  • Prioritize tasks by importance or risk
  • Group tasks into 1st, 2nd, and 3rd pass; each pass is more granular
  • Include easy to miss, yet critical tasks
  • Include essential elements from court- or firm-mandated style guides
  • Limit yourself to one or two pages of easy-to-read font

2. Use reverse outlines to check your structure.

Outlining before writing helps some people organize their thoughts, but for others it can be too restrictive and, as a result, prescriptive. Sure, it helps to organize your thoughts, but some people just don’t work well that way.

Personalities and circumstances may require different approaches. For example, in law, we continue to discover new information throughout the writing process. We learn new facts, ask new questions in response to research, and revise our strategy accordingly. If we tried to learn everything before starting, we’d never start! So a rule that says you must outline before you write may not be useful. That doesn’t mean that an outline can’t help make a better final document. Try reverse outlining.

What Is Reverse Outlining?

Reverse outlining is the process of producing an outline from a draft you’ve already written. It allows you to create information organically, writing as you are inspired, then search for patterns later. When you reverse outline, you review your work and pull out the main ideas and supporting points. Then ask yourself: Is that really what you meant to show?

Why Use a Reverse Outline?

Done properly, reverse outlining will yield a condensed version of your argument to evaluate. It will show you whether your logic, support, and flow deliver your intended message.

A reverse outline will make obvious any weaknesses in your document’s organization and expose any unnecessary repetition. It will also show you whether you have an unclear thesis statement, make unclear or unsupported claims, or have disjointed or disconnected analysis. It’s tough to see these things as you’re writing. Forcing this organization during the writing process may lead to awkward flow and artificial, stilted transitions.

Create Your Reverse Outline

To create a reverse outline, you’ll work with the existing structure of your document and distill the main point of each paragraph one at a time. Be sure to stick with what you actually wrote—don’t create an outline for what you meant to write.

Here’s how to do it:

  • Number the paragraphs of your document
  • Review your document paragraph-by-paragraph
  • Identify the main topic of each paragraph
  • Write that main idea in the margin or on a blank page
  • List the supporting points for that main idea

Once finished, your reverse outline should look like any other outline, but with more detail. The next step is to analyze it and revise.

Analyze Your Reverse Outline

Does your outline meet your goals? Analyze what you wrote to determine whether the completed document did what you meant it to do.

  • For overall organization, consider: Did your ideas flow logically and build on each other? Did you give readers a roadmap so they could follow your argument?
  • At the document level, ask: Did your main ideas work together to match your document’s purpose? Consider how many lines you devoted to each topic—do the important topics take up most of your document?
  • At the paragraph level, check for: a main idea; whether it accomplishes its goal; and whether it stays on topic—or does it contain stray ideas and details? And ask: Is every paragraph both strong and valuable?

Don’t be afraid to move paragraphs and sections around or to delete paragraphs that have drifted off topic.


Creatively using classic writing tools, like checklists and outlines, can free you to write to your strengths and improve your results. This helps produce high-quality writing within tight timelines. Once you’ve edited for organization and content, let WordRake help you edit for clarity and brevity. It will help you tighten and tone your prose and cut the clutter, leaving only what you meant to write. Try WordRake for free today.


About the Author

Ivy B. Grey is the Vice President of Strategy and Business Development for WordRake. Prior to joining the team, she practiced bankruptcy law for ten years. In 2018, Ivy was recognized as a Fastcase 50 Honoree and included in the Women of Legal Tech list by the ABA Legal Technology Resource Center. Follow Ivy on Twitter @IvyBGrey or connect with her on LinkedIn.

Our Story

WordRake founder Gary Kinder has taught over 1,000 writing programs for AMLAW 100 firms, Fortune 500 companies, and government agencies. He’s also a New York Times bestselling author. As a writing expert and coach, Gary was inspired to create WordRake when he noticed a pattern in writing errors that he thought he could address with technology.

In 2012, Gary and his team of engineers created WordRake editing software to help writers produce clear, concise, and effective prose. It runs in Microsoft Word and Outlook, and its suggested changes appear in the familiar track-changes style. It saves time and gives confidence. Writing and editing has never been easier.