Word-of-Mouth and Referral Marketing Blog

How To Write Well? Ask Better Questions


I was both pleased and frustrated when reading Jason Freedman’s Five Paragraph Essays on 42floors’ blog. Pleased because he addressed the very real problem of stodgy, formulaic writing, but frustrated because he didn’t actually get to the heart of the problem.

Here’s a quick recap of Jason’s post:

  • Jason used to write in a predictable 5-paragraph-essay format. He mastered this in high school, thanks to his AP English teacher Mrs. Streeter.
  • In college, he peer-reviewed an essay which answered “What was King Lear’s fatal flaw?” He encouraged his friend to follow the strict 5-paragraph format.
  • His professor, Professor Wheaton, informs him that he has to unlearn the rigid structure that Mrs. Streeter taught him.
  • Jason posits that rigid structures are the source of bad writing, and recommends verbal dictation as a “trick” to escape learned rigidity.

“To become a better writer you have to stop writing and start speaking.”

I must admit, this does improve the form of your writing. People are typically more experienced at speaking than writing, so our speech tends to be a little more “natural” than our writing.

Note that “natural” here describes the sort of easy, confident competence that comes from experience. The more conscientous practice you have, the more natural you will seem at whatever you’re doing.

But that doesn’t change the fact that listening to someone speak fluently about boring stuff isn’t much very better than reading boring stuff that they wrote.

When it comes to good content, form doesn’t matter nearly as much as substance.

Form does matter, but discerning audiences typically are more concerned about substance. And the magical thing about good substance is that it inspires good form. When you find something really important that’s worth saying, the weight of the moment will force you to write more economically.

So the highest order bit for writers and bloggers isn’t to experiment with their structure, but to focus on writing things that are genuinely interesting and useful. Here’s my one trick for helping people become better writers:

To become a better writer you have to ask better questions.

I don’t mean that in an abstract or rhetorical sense. Look around! There’s amazing content being posted, shared and upvoted on Hacker News, Reddit and Quora (and Medium and…) every single day. Great writing is borne out of good writers answering to good questions.

In both cases, we encounter fantastic writing from writers who clearly loved the subject matter. But it took the right question (and environment) to trigger the cascade of words that would eventually be recognized by others as quality writing.

There are countless other examples of great questions inspiring great writing, which you can see in Best of Quora 2010-2012, or on r/askreddit/top and r/explainlikeimfive/top, amongst other places. I’d highly recommend every blogger to carefully dissect and analyze all of those questions. Pick them apart, see what makes them tick. One has to wonder, what would it be like if we practiced and developed the ability to ask such good questions of ourselves, and one another?

Let’s revisit Professor Wheaton’s statement:

What I wanted you and your partner to do was put some real thought into the character of King Lear and write me an essay that helps unpack all of that.” – Professor Wheaton

It’s a noble agenda, but what neither Wheaton nor Freedman seem to realize is that “What was King Lear’s fatal flaw?” is a horrible question! It doesn’t actually direct the essayist to do what the Professor wants. The student is trapped in the unenviable position of trying to intuit what the professor wants to read, while simultaneously answering an oversimplistic question.

Jason tells us that it’s time to leave Mrs. Streeter behind. He’s completely right.

What he missed, though, is that it’s time to leave Professor Wheaton behind, too.

Practicing what we preach:

I don’t want to be too self-promotional, but in this case I think it’s warranted because anybody telling other people how to write ought to have a few decent examples of her own. Here are some of the questions we’ve asked and answered on this blog, which have resonated with others:

How many online stores are there in the US? This was a question with a concrete number, and we had to do some research and use some mathematical modelling to get the answer. It’s a figure that’s been cited multiple times, most notably on Forbes.

What IS social media, exactly? This stemmed from our frustration with imprecise terminology, and a sense that most people aren’t really sure what they’re talking about when they talk about social media. Answering this question helped us think about other questions too, such as Why are people so annoying on social media? and the relationship between mainstream/traditional media and social media. (Social media emerged from social networking sites, and went on to disrupt traditional media.)

What’s up with the relationships between white girls and Starbucks? This was a fun thought to explore, and there’s actually room for a lot more nuance. I just thought I’d ask the question, and explore the landscape a little. It’s gotten thousands of hits from search engines, presumably because it’s a question that lots of people have, and few people have really bothered to try answering properly.

Further reading:

If you enjoyed this post, I highly recommend Paul Graham’s The Age Of The Essay, which demands the delivery of the unexpected. If you’re feeling adventurous, there’s also George Orwell’s Politics and the English Language, which describes how bad writing is used to deliberately avoid saying anything of significance.


Visakan Veerasamy

Visa is ReferralCandy's former Blog Editor [2013–2018]. He also co-founded Statement.sg, a fashion ecommerce label selling witty t-shirts. He's mildly Internet-famous for his elaborate Twitter threads. He hopes to enjoy a glass of scotch onboard a commercial space flight someday.

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