Make their choices easy by giving details and examples
For all the required materials, show the students where they can buy, what specification they should look for (2B pencil, 0.5mm mechanical pencil, etc.), and how much.
For organization and legible writing, provide a few examples on what you consider as organized and legible. Annotate with your comments if necessary. You can then attach a learner's contract at the end, let the students sign to attest that they can produce work with comparable legibility and clear assignment of section titles, etc. This should be done once, at the beginning of the course.
This contract and printed example are necessary. The examples allow the students to judge their work more objectively, the contract instills a sense of seriousness and responsibility.
Distribute an assignment coversheet with checklist on it
Now that the groundwork is laid, give each of them a homework cover page whenever you give an assignment. The page should at least list:
- A place for student to write down their name
- Course code/title
- Assignment title
- Due date/time
- A checklist of your requirements for student to check
The checklist can contain your objective or measurable criteria. After each criteria, attached a box that, if checked, would indicate the criterion is fulfilled.
The students will have to check all these by themselves, and then staple the front page to the assignment before handing it in. In terms of how to deal with unchecked items, it's all up to you, as long as the consequences are clearly printed on this cover sheet. It can range from "If any of these item is unchecked, your work will not be higher than a B-" to attaching corresponding points to be taken away for each violation, then you can let them pick which to forfeit.
Have you had someone checked the box without being organized?
Yes and no. I specify that all the assignments need to be typed so I never had the problem of self-claimed organization that actually looks messy. My checklist consists of mostly clearly yes-or-no's: "1-inch margin," "mentioned sample size in the Methods," "did not report p-value as zero," etc.
But your question did prompt me to think about a method we use when hiring interviewers. When we hire interviewers, we sometimes give them a sheet with numbers (0-9), some common phrases (such as "Not application," "N/A,") and words likely causing confusion (-y vs. -g, double t, etc.) printed on them. Then, we ask the candidate to copy the numbers and words by hand. Those forms are life savers whenever we're confused by their hand writing on the data collection sheet. We have used them in a pinch when entering data, and we have used them to advise data collectors who show deteriorating handwriting quality.
So, I guess you may modify your standard a bit. Instead of showing them some pre-existing copies of assignment, give them a couple pages of sentences and formulas and ask them to neatly copy them. Afterwards, if you're happy with the quality, they may proceed to sign the contract. Keep both writing sample and the signed contract together.
Would this prevent students from blindly checking the box? Not entirely. But at least now you have a good sample and a bad sample from the same student on the file, and it'd be easier to point out what went wrong.