For the email situation, why wouldn't you just send it out to 100 customers to get a sample of confusion? Reply to the 10 people who were confused, fix the problems, repeat.
Same goes for websites. People send in "HN please review my site" all the time.
But your point does stand for websites. Politely asking people to review your site on HN will allow for some great feedback, but you really only get one shot at it.
Anyone know if a service exists (-MTurk) where you can pay people to constantly review your site?
I think that'd be an awesome way to evolve a website. Just apply constant feedback by paying people to launching fast and iterating.
Concise answer: MTurk was an obvious, yet too simple solution.
Long answer: My imagination was something designed specifically for pushing websites to some degree of success. So without me having to think of all of the different dimensions that bring a site to success (clearly state what it is, beautiful design, something people want, easy to use) -- the site I have in mind would walk you through that process taking your money at iterations of each step. In the end, you should have a site that meets the standards of sites which are already winners with most if not all of the dimensions in question.
There's FiveSecondTest (http://www.fivesecondtest.com/) that shows an image of your website for five seconds and asks users for their feedback. Not enough time for users to read all the text, but it's good at seeing if your general point is getting across. It's free too.
that's what the non-tech guy on our team is for (among others things). constant user studies.
you have to be hitting the right crowd. asking advice from HN or random people only works if your site is meant to have universal appeal. HN in particular is a heavily skewed audience.
Once he's been on the team for a short time though, and if he's used the website a lot, then he's not going to provide the newcomers or non-technologists perspective. This is a situation in which increased knowledge of the user decreases their worth to the process.
It's very hard to pretend to yourself that you haven't seen something before and imagine your reaction - was that logo clear in its affordance?, etc..
That's a trial and error process of proof reading your writing. Inefficient IMHO. A solid approach would be clarity of writing through lucid and cogent thought; if your thinking is clouded so is your writing.
It never hurts to read aloud your email to be sure it "sounds" right but that is, I assume, something everyone practices before they post, email, or submit.
That's basically using an audience of 1. Starting with yourself and checking if it sounds right. After that, you'd probably bounce it to a few people in the office, see what they think. They might pick up on something that sounds clear to you, but doesn't make sense to other people.
Finally, you would want to bounce it to a few customers. Everyone inside the company is going to have a similar set of knowledge and assumptions when they look at the email, the only way to really be sure is to send it out.
I don't think he's saying you should write down some random thoughts and test them, but rather as a final proof-reading step before sending it out to everyone.
Even lucid, cogent thought can result in confusing prose. Proofreading your own writing is necessary, but not sufficient.
The problem is that, for you, the abstract thoughts in your head came first, and the prose came second. When you re-read your prose, you're reminded about all of the implications of the abstract thoughts in your head. When someone else reads your text for the first time, they have to construct the abstract thoughts from your words alone. This process reveals confusion that you probably would not find on your own.
"but that is, I assume, something everyone practices before they post, email, or submit" I like your optimism, but I'm guessing the majority of people do not in fact read things aloud before submitting. I'm sure it's different when sending an email to thousands of customers, but the quality of comments on any forum site suggests it's nowhere near universal.
There are cases when you don't need a huge audience to feel pain when unclear.
'An old blacksmith realized he was soon going to quit working so hard. He picked out a strong young man to become his apprentice. The old fellow was crabby and exacting. "Don't ask me a lot of questions," he told the boy. "Just do whatever I tell you to do." One day the old blacksmith took an iron out of the forge and laid it on the anvil. "Get the hammer over there," he said. "When I nod my head, hit it real good and hard." Now the town is looking for a new blacksmith.'
I used to post longer pieces that looked at a subject from a few different angles. They didn't seem to be getting through to many people.
Maybe because a quick glance at a longer article make you say, "I'll read that later when I have more time." (At least that's what I often do.)
When I started breaking up each point into its own separate short post, they started getting more response, retweets, comments, etc. Maybe because it passes the GTD "under 2 minutes" test?
I have often though this in work project emails to a much smaller audience (under 20 people). If I get one person replying back to me asking to clarify something, then I have failed in some way or another in my explanation, so I always read everything more than once.
I have noticed that many of our off-shore contractors, where English isn't their first language are prone to sending unclear emails - it's actually quite frustrating going through several replies to get to the bottom of it, and it often causes things to be delayed unnecessarily. If only everyone thought so carefully before sending the email!
I had to follow the link to find out what he meant by "when unclear." It's ambiguous between "express yourself unclearly" and "perceive something unclearly," which is a pretty big difference.
Actually, my first thought was the character in some Woody Allen (?) movie who just won't come into focus. It jeopardizes his career as an actor.
It aids clear thinking to habitually demand immaculate precision in your speech. It's not just for mass-emails or public-facing websites--it helps you, too.
Same goes for websites. People send in "HN please review my site" all the time.