Overcoming common writing problems argument organization and backwards outlining

Welcome back to our series on overcoming common writing problems!
In the first post in the series, we talked about making sure you’ve locked down the essential elements of a post—an intro, a “this post is about” sentence, good subheads, and a conclusion. This time, we’re going to talk about more big picture stuff. Specifically, we’re going to chat about how to get a bird’s eye view of the flow of your ideas and check that your argument is cohesive.

Wait, Do I Have Organization Problems?

Most people don’t realize that they’re getting off track as they’re writing. They sit down to write about a topic and just let the ideas flow. I mean, that’s what I do.
But there are warning signs that you have organization and argument problems. Here are a few of them:

  • You have trouble writing a conclusion (a sign that you’re not sure what you proved)
  • You have a really long, all-over-the-place conclusion (a sign that you covered too many points with no overarching takeaway)
  • You find yourself making a lot of diversions or side notes in the text (a sign that your mission as discussed in your “this post is about” sentence—the one where you say what the post will prove—isn’t covering the scope of what you have to say)
  • When you go back and read the post after a few days, you feel vaguely like you didn’t quite express yourself as clearly as you thought you did but you’re not sure why (a sign that…you didn’t express yourself as clearly as you thought you did 🙂)

Notice that all these warning signs come after composition. And that’s okay.
If you want to do some upfront work to try to prevent argument flow problems, sure, you could write an outline first. Outlines are never a bad idea. But our ideas often flesh themselves out as we’re writing, so trying to plan everything out perfectly before you write has its problems. I’ve never once had a piece of writing spring onto the page fully formed, like Athena popping out of Zeus’s head.
That’s why I’m going to give you an after-you-write tool that will rock your world.

The Solution: Backwards Outlining

Backwards outlining is one of my absolute favorite things in the world to share with writers. It’s like developing 3D vision after seeing in 2D for your whole life. Here’s how it works.
After you write, record your “this post is about” sentence. What did you want to prove with this post? What was the main idea you wanted to convey?
Now, write down each of your subheads. Ask yourself how each section (which should have its own singular mission) ties back to your main point. It should be short and easy to understand. If you have to jump through mental hoops or take a long time to explain it, your section needs work.
Next, look at each subhead again. Write down how each section connects with the section before it. Do your sections, as indicated by your subheads, build on one another in a logical order?
So, in summary, here are the steps to backwards outlining:

  1. Record your main objective for writing the post.
  2. Record all your subheads and ask how each section supports that main objective.
  3. Ask how each subhead relates to the one before and after it and see if those ideas flow.

As with most things, this becomes easier to understand once you see examples. So let’s work through a few of them.

Backwards Outline Example: A Post That Doesn’t Need Work

First, let’s take a look at a post that makes a solid argument start to finish and flows really well. It’s written for our client Plutora by our author Eric Boersma, and it’s called, “Is There a Place for the Waterfall Methodology in 2019?” You can read the post if you want—and you should because Eric’s a lovely writer—but what I’m about to share should make sense even without the background of the post.
Note that there isn’t a ton of text explaining the connections. It’s short and simple. That means those connections are easy ones to make, and that’s what we want.

Backwards outline good

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Backwards Outline Example: A Post That Needs Organization Help

Early in HS days, we worked on a post from an intelligent writer who had exactly all the right ideas and a great deal of valuable insight. But he just didn’t have the tools—backwards outlining—to organize his arguments for maximum coherence and power.
Here’s the original draft, if you want to follow along with my assessment. Otherwise, you can just trust my analysis and see what a backwards outline turned up:

Shadow IT First Draft Backwards Outline

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There’s a lot of great things about this post, but I’m going to be the bad guy here and focus on the negative. After all, we’re here to see what a backwards outline can reveal when there’s something not quite right but you’re not sure what.
So, what we saw above forced us to think about the post objective and then the actual content section by section. And it revealed two big problems that we might not otherwise be able to articulate:

  1. Much of this post shares the author’s observations about why shadow IT happens, not so much why it’s defensible, from a business perspective (which is the objective of the post, as stated in the intro and with the title).
  2. It doesn’t flow from one thought to the next in a logical progression, nor does it build steadily toward a powerful, convincing point at the end.

What the Revised Version Looked Like

So, Hit Subscribe editorial worked with this author to reframe the content. In the end, the author was able to make the connection to the mission clearer and improve the flow. Here’s what the backwards outline looked for the post when it was finished. (Take a special look at the new section headings!)

Shadow IT New Backwards Outline

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And the Backwards Outline Shows Even More Room for Tweaks!

Note that the backwards outline revealed that, from a bird’s eye view, things still aren’t quite perfect. Hey, this is real life. And besides, the post turned out well overall—HS only delivers ones that we’re proud of. But let’s talk about how we could have fine-tuned this even further.
While this argument has great flow now (as you can see from the subheads), it was a stretch to tie a few of the sections to the objective. If this were your post, this backwards outline would alert you to the possible need to tweak the wording of your objective to better match your now-solid argument. And it’s totally fine to do this after you’ve composed! Sometimes we don’t know quite what we’re going to prove until we’ve proven it.
In this case, you can see that this post could easily be made more airtight by reframing the objective (in the form of a “this post is about” sentence) to something like

I’d like to submit that, believe it or not, shadow IT can be a way for companies to find the balance between speed and security.

If we’d have done that, every section would be a no-brainer tie to the objective.

What If It’s the Text Inside My Sections That Feel Off?

So, you feel like your overall argument is solid, and it backwards outlines beautifully. Nice work!
But maybe a section feels off. Maybe when you read it, it seems to lack punch, or you’re not happy with the way it flows. Or maybe it’s just really long and you want help knowing where and how to break it up.
Guess what? You can backwards outline your section! The process is the same as the big backwards outline, but instead, you

  1. Record what your objective for the section is.
  2. Write down how the single idea expressed in each paragraph helps achieve your section objective. (<–Important! A paragraph should have only one main idea.)
  3. Write down how each paragraph relates to the one before it.

I’m not going to show an example of that here—we’ve covered a lot already, and I think you’ve earned a break from this intense detail work. Please go get a snack and scroll mindlessly through Instagram for a while to recover.

Having Trouble Applying the Concept to Your Own Writing?

It’s really difficult to do this without an example to work through, and it’s even harder if you don’t have someone experienced in backwards outlining along for the ride. Sure, I showed specific examples here. But those will only truly click with you if you become deeply familiar with the content we worked with. And studying blog posts written by other people just for the sake of understanding my examples…well, ain’t nobody got time for that.
But you’ll know your own blog post in and out, so you’re in a great position to do a backwards outline with one of our editors and learn how to massage the content you already have into a solid argument that achieves its goal—and does it in a way that flows with purpose.
Want to give it a try? If you’re a software engineer, apply to write for us. We’ll work with you on this and on other writing skills you can take with you and use for the rest of your life.
Or maybe you want to try it on your own, without our help. If you do and you use my instructions, let me know how it goes. While I’ve done this with countless authors, I’ve never tried to explain it quite as I have here. I’d like to know how to make my explanation clearer and easier to follow, so your thoughts are welcome in the comments.