Diagnosing & Curing Common Writing Problems

You can plan a great content strategy, but if you don’t have the writing abilities to execute it, your content will fail. Give yourself a writing check up!

guest post graphicEverybody wants to be a better writer these days. The experts keep telling us to create “great” content, like it’s as simple as making a bowl of cereal.

But it’s not.

Bad writing is everywhere, from humdrum blog posts to garbled landing pages. There are brilliant ideas that will never get the attention or recognition they deserve because they’re mired by weak, anaemic or delirious writing.

Don’t worry, the doctor is in.


Writing Ain’t Easy…

Perhaps that’s because writing is more than a set of grammatical rules or the ability to string words into sentences. It’s a developed skill, a mental game of persuasion, a war for the reader’s attention.

It’s a war you can win and a skill you can learn.

In this piece, I want to help you cure your writing ills by identifying the symptoms, getting right to the root causes and giving you some resources to improve.This doesn’t just apply to your own writing. What you learn here will make you a better editor, written communicator and all-around human being.

Sold? Then let’s get going.

What this is not:

  • A guide to generating topic ideas or beating writer’s block. Lisa Barone has written a fantastic piece on content ideas and Gregory Ciotti can help make you more creative and get out of your rut. If you need help with those things, moonwalk thattaway.
  • A grammar-centric snooze-fest that will harp on the proper usage of the words “there, their and they’re”. We’ll touch on it, but I think you’ve been scolded enough.If you want to improve your grammar (and it’s pretty important you do), there’s a tool for that. You can also see the “5 Cures for Most Major Ills” at the end of this piece (but don’t skip the meat in the middle).
  • A catch-all. There are many different types of writing out there; sales letters will look and sound different than blog posts, which are wildly different from technical writing. It’s up to you to apply what you learn here to the format at hand.

What this is:

  • An actionable guide to diagnosing some of the most common writing problems that damage your brand, lose you conversions and cost you respect – and some actionable ideas as to how you can fix them.

Problem #1: Your Writing is Disorganized


  • Your writing lacks “flow”; ideas jump from one to the other with no clear connection
  • You find that you’re rambling from idea to idea, unsure of where or how you’re going to finish
  • Your visitors aren’t staying on-page long enough to finish the piece
  • Responses from readers includes: “I’m not sure I see your point”, “This doesn’t read well”, “How is this related?”, “Could you explain what you meant by…” or “I’m not following your logic.”


You’re not using frameworks or mental models to guide your writing structure.


Create an outline to bring order to the chaos, and test your outline by stepping into the head of your reader.

When inspiration to write strikes, you’re hit with a flurry of ideas you want to capture before they can float away. Visually, the idea generation process looks something like this (an example from the piece you’re reading right now):


But readers don’t read like this.

One spurt of genius must flow to the next without crippling, unanswered questions left along the way. I find it helpful to think of this in two ways:

  • If you’re telling a story, the plot needs to connect cohesively from scene to scene.
  • If you’re writing a paper, every argument needs to be supported and explained before moving to the next.

Step away from your keyboard and chart out the structure of what you’d like to write, breaking it down into clear, obvious pieces  with supporting arguments or “plot elements”:

And imagine you’re reading it to an aggravating 2 year old:

“Experts are recommending content marketing for small businesses.”
“Because the statistics show it’s an incredibly effective form of marketing.”

And so on.

Following our earlier example, here’s those same ideas dropped into a structure:


Once you’ve drawn out the framework, test it with a “mental model” by charting the questions and thought process of your reader as they navigate your piece. Anticipate the reader’s headspace, needs and questions before they can even ask.It’s a bit like chess.


Finally, write the content following your model. When you’re done, review. Have you left all questions answered? Does your “plot” make sense?

If you’re unsure where to begin, Open Polytechnic has a great set of resources on improving the flow of your writing.

Problem #2: Readers Tune Out Early


  • Readers begin your content, but don’t finish.
  • Time spent on your piece is low and bounce rates are high


  • You’ve failed to prove your piece will do what it promises
  • Your piece looks too daunting to read

Or, most likely:

  • The “Why” is not established early on

Something I was taught early in my writing career is the principal of honoring your reader’s time. As a writer, it’s easy to get cute and try to build up suspense for the “big reveal” at the end of your piece. The trouble is, your audience has questions, and they want them answered NOW.


  • Don’t wait to show your readers the benefit of your piece or save big stats for the end. Avoid wasting the opening paragraphs of your writing on eloquent introductions.Instead, give the reader a compelling reason to keep going by showing them the benefit of what they’re about to learn, buy or do.
  • Don’t resort to gimmicky, click-worthy headlines unless they align with the content you’re providing. The bait and switch is the lowest form of journalism; deliver the content your headline promises.

Problem #3: Writing is Off-Brand/Inconsistent

This problem plagues both individuals and groups – especially when there are multiple contributors to a project. As everyone brings their own style to writing, style, subject matter and content can get a bit schizophrenic.


  • Your pieces vary wildly in tone and voice, from funny to eloquent to abrasive and beyond.
  • Your target audience can’t describe your brand’s personality in two words, or the two words used range wildly


Writers have no roadmap or reference to follow.


Create and enforce a style guide.

Have you ever actually sat down and thought about how you’d like to be perceived when you write? Yes, everyone is a snowflake, but there should be unifying themes and a cohesive element to your brand’s communication – even if that brand is yourself. That goes for blog posts, sales letters, newsletters, web page copy – it all has to sync up.

I hit upon creating a style guide in “The Complete Guide to Working With Copywriters”, but a quick review:

  • Define the personas you are trying to reach
  • Clearly express the goals you are trying to achieve
  • Articulate your brand’s tone and voice: the framework you will use to reach them
  • Set rules for verbiage & formatting
  • Refine the style guide as you get more feedback from writers over time

Problem #4: Fillers, Fall backs & Turns-of-Phrase

Have you ever watched someone give a presentation and noticed how often they say “um”, “yeah” or “y’know”? These “fillers” are borne out of habit, nervousness and a lack of self-awareness – and they exist in writing too. They can quickly distract readers and pull their minds out of the piece they’re reading.


  • Repeated turns of phrase, ie: “Whether you need X or Y…”, “As a matter of fact…”, “In other words”, “Of course…”, “Literally…” – and one that I’ve personally struggled with, “Now that you’ve X, it’s time to…”
  • Overused descriptors, sometimes close together but often spread a few sentences apart. E.g. “Remarkable” – In this remarkable study, we saw that over 10% of Americans don’t know how to make Jell-O. It’s quite remarkable!”


  • Old habits
  • A limited or comfortable vocabulary
  • A lack of self-awareness when writing


“Fillers” tend to be unique from person to person. The first step to recovery is finding yours.

Read your piece aloud to someone else, and then have them read the same piece back to you. Your ears should be attuned, listening for overused phrases or comfortable fallbacks. Flag them, write them down on a post-it and keep them where you write.

(For extra fun, use the “Find” function  to see how often you’ve used your fall backs across several documents).

When you’ve identified the problem, bust out your old friend the thesaurus and jot down 25 different ways or words that mean the same thing. Put these on a post-it next to your other post-it. Now, you’ve got options to practice.

Problem #5: Typos & Oversights

Spell-check and Microsoft Word, right? DONE!

Not so fast.

While a typo might not cost you $250,000, it could cost you up to 50% of your sales (or more, depending on how bad the problem is). Typos are often linked to bad grammar – if you don’t know what word to use, even correctly spelled words can be typos.

Worst of all, though, is that typos destroy trust. If you haven’t taken the time to edit your own writing, why should any client or customer trust you’ll take your time and pay attention to the details with them?


  • Words are spelled wrong
  • Words are spelled right, but they’re not the right words (way more deadly!)
  • Misplaced commas, abused semi-colons and tormented exclamation points
  • Improper word usage


A lack of proper editing; no “simmering” or editing time.


If you never want to suffer typo again, there’s an easy, four -step process:

  1. Read it out loud at half the speed you would normally read.
  2. Wait awhile; a few hours is good, a few days are better.
  3. Read it out loud again.
  4. Have someone else (your computer’s speech program, if necessary) read it out loud one more time.

In addition, always, ALWAYS cross-check unconventional words like people’s names. It takes seconds to take a second or third look, but it can mean the difference between a conversion and a bounce.

Problem #6: The Content Isn’t Persuasive

There are a multitude of reasons writing fails to persuade its audience, many of which we’ve already covered: length, tone, grammar, organization – they all contribute.

Trying to unpack why your specific piece didn’t accomplish its mission is a daunting task, but here is a final list of “usual suspects” to turn to when everything else is in check.


  • Conversion rates are low despite clean, grammatically correct and typo-free copy and a clear call to action (if you haven’t covered these bases, you’re destroying trust no matter how good your point is)
  • Readers aren’t convinced of your point or do not see a need for what you’re sharing


  • The audience’s needs have been poorly defined, so the piece doesn’t resonate
  • You have not established credibility
  • You haven’t appealed to logic, emotion or tradition
  • Copy may be too self-centric, focused on you as a person or company and not them as a reader or customer
  • The “WHY” of your writing is unclear; you’ve given the audience no reason to care or agree with what you’re stating
  • You’ve failed to provide “because” statements or back up your claims sufficiently with evidence or appeals.


  1. Establish some form of commonality with the reader. What do you both want, or want to avoid?
  2. Revisit your audience’s needs. Have you correctly identified them?
  3. Review your arguments. Have you provided sufficient supporting data, leaving no questions unanswered and no room for skepticism?
  4. For sales-orientated pieces, how often are you talking about your business vs. the benefit to your customers? Have you made it all about you?

In reality, persuasive writing is an art form and we’re only scratching the surface. Here are just a few resources to help you master it:

5 Cures for Most Major Ills

Whether you struggle with structure, grapple with grammar or can’t seem to persuade your audience, there are three tools at your disposal that will help you improve as a writer.

1. Find An Unbiased Peer Group

To improve your writing, you need to look outside yourself. Often, a writer will be too close to their own work to see where they could improve. Seek out experienced writers who can give you the hard, honest truth about your writing and where you need to improve and aren’t worried about hurting your feelings.

Source them as editors and give them free reign to tell you exactly what you need to hear.

2. Conduct Rigorous Testing

You are not finished when you push the “publish” button. Every piece of content you write is a live, real-time test that gives you insight into how well you’re connecting with your audience.

  • Test headlines. Upworthy writers need to come up with 25 of them; your first is rarely your best.
  • Test calls to action. Use A/B testing if you can. See if you can drive a better response to the same piece of writing.

Test formats and lengths. Would the same message be better received if presented differently?

3. (Actively) Read More Often.

If you want to improve your command of the written word, you need to find yourself some role models and study what they do. But don’t passively pick up a book and expect to learn from osmosis – read actively.

What does that actually mean?

  • Keep a pen and paper nearby, jotting down the turns of phrase and word choices that you found particularly interesting
  • Create a mock-up of what you imagine that writer’s outline, plot or framework was and analyze how they strung their ideas together.
  • Find writing that you feel is “bad” and critique it. Learn from others’ mistakes; know what turns you away so that you can avoid repeating the same mistakes.

4. Write (with Intention).

I wish there were a “magic formula” to give you, but like any skill, you will only master writing through practice. That said, where others will stop at saying “Write more often”, I’m not content to leave you fiddling with a keyboard and hoping for the best.

As you write, choose areas to practice and be deliberate about your learning. Much like learning to play piano consists of technique, notation and physical movements, learning to write consists of theory (how to be more persuasive), application (proper structure of a piece) and mechanics (grammar).

  • Create writing experiments for yourself, using formats and subject matter outside of your comfort zone. Test your ability to capture a subject, drive a conversion or earn a response.
  • Choose areas of weakness (have others help you identify them) and be deliberate about learning in those areas.
  • Write for hyper-critical audiences – SEEK OUT criticism. You’ll need a thick skin, but nothing fosters change like the honest feedback of an invested audience.

5. Edit For Others.

You don’t need to be a professional writer to give feedback on a piece. Editing the work of others gives you an opportunity to learn from others’ mistakes and adopt their strengths. As an added benefit, you won’t have to write 10,000 pieces to keep progressing; you’ll be learning to spot problems in the work of others, which translates back into your own work.

It’s a Long, Wordy Road…

Improving your writing is a process that will take time to learn. But armed with what you’ve read today, you should be prepared to identify, diagnose and treat some of the more common problems plaguing content on the web.

responses to “Diagnosing & Curing Common Writing Problems”

  1. Krystian Szastok says:

    I think the point about structure is crucial. From experience I can say clients mind if an article is chaotic. They appreciate ‘easy read’, ‘good flow’ etc.

    I think too many copywriters just spit content out without being critical on themselves.

    Some are also very protective over their writing usually. Afraid of bad comments and not willing to adjust.

    I think finding an unbiased group or even one person to read your piece of content as a human would without judgement – is the best remedy to most issues.

    • Joel K says:

      I think it goes beyond copywriters too! Everyone could benefit from a bit more structure and flow. Being protective of one’s own writing is an insecurity, it’s the false belief you can never get better and have hit your ceiling. I hope to never hit my ceiling.

  2. Desirae Odjick says:

    Awesome post, Joel!

    The one thing that I would add to the third “cure” is to read outside of your field, industry or writing style. I’ve found it’s really helpful to get me out of my head, help me read actively and switch up the way I think and write about more “standard” topics.

    If I’m stuck saying the same things over and over again, I’ll take a break and read fiction, or a non-fiction book completely unrelated to marketing or business. It helps me see how other fields write, which is sometimes just the thing I need to find new ways to phrase an idea.

    • Joel K says:

      Thank you, Desirae! (And thanks for following my subtle hint on Twitter, hah!)
      I think it definitely helps to read outside of what’s comfortable and familiar – I just think no matter what you read, you need to read actively instead of hoping you’ll just absorb what you need to learn.

      Fiction is a wonderful place to learn sentence structure and descriptive language; storytelling is something that you can easily weave into business communications as well.

  3. ronellsmith says:


    Give it up, please, sir. You are making it look too easy. Just … Dayum! Fine work, sir.

  4. Baadier Sydow says:

    Great post Joel but that goes without saying. I’ve just realised I’m a poster child for problem number 4. Along with my inclusion of South Africanisms(proably not a word) I can really put together some terrible copy.

    • Joel K says:

      Cheers, Baadier! It takes a long time to improve, but you have to be deliberate about it.

      • I think that’s probably everything really in a nutshell. You have to aim the arrow so to speak and really focus on it. We are redeveloping our site and getting a copywriter to redo the core site content. We debated doing the same thing for our future blog posts but decided the best thing would be to keep that as our “true/natural voice”.

        Definitely merit in having it looked over by a copy writer before publishing.

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  13. Megan Garner says:

    I do love my fillers and turns-of-phrase… I think I’ll examine my writing more closely from now on. I like the idea of letting your writing “simmer.” It really makes a difference when you leave a blog post or article alone for a few days, and then come back to see the moronic sentences you’ve constructed. Thanks for the helpful and interesting article, Joel!