* The Discipline (And History) Of Checklists, Including USAF Pilot Training (Or Why ‘AI Workflows’ Should Be Renamed ‘TODO Lists’)

This Is Our “17 Seconds” Newsletter #146: 17 Seconds = Useful Info Quickly.

OK, one more newsletter about pilot training. Sort of.

Erik And Checklists

I have been making lists (and checking things off) for as long as I can remember. Perhaps this began when I was collecting baseball cards, coins, and stamps. Or perhaps earlier. I sometimes joke that I don’t have OCD but instead have CDO, which is like OCD except in alphabetical order. (And please note from a couple of sentences ago that my list of collectibles is in alphabetical order.)

For my 18th birthday, my friend Peter Carroll (now a history professor at Northwestern University) gave me a copy of the 1977 book “The Book Of Lists,” in which he wrote:

“Erik, This is the gift that you had to receive. This will let you know that there are others like you out there somewhere. May this also represent a symbol of you. Remember how your lists have slowly driven people mad, especially me. Happy Birthday! -Peter”

Please also note the “1977” that I wrote on the first page. This is because my bookshelf is arranged in chronological order (of course it is).

USAF And Checklists

In 1989, when I was in USAF pilot training, all student pilots were given a T-37 “Abbreviated Flight Crew Checklist” booklet, which was then strapped to one leg during flights, with key pages tabbed (such as landing procedures and emergency procedures). Some checklists I remember, such as the one for ejection: handgrips raise, triggers squeeze. Others I do not remember. Still others are not in the (abbreviated) booklet, such as the spin-recovery procedure. The T-37 is easy to put into a spin, which makes it possible to teach spin-recovery, and I remember being very good at that one. I guess that we had to memorize the spin-recovery checklist, since it’s difficult to read from a booklet when you are spinning out of control!

Clocktower And Checklists

In 2001, when I launched Clocktower, I divided the physical storage space into five “libraries,” namely:

  • Admin Library
  • Clients Library
  • Law Library
  • Marketing Library
  • Tech Library

Our virtual “libraries” (i.e. our intranet) mirror the physical, with folders named as follows:

  • admin-library
  • clients-library
  • law-library
  • marketing-library
  • tech-library

I created procedure manuals for each library, each of which contains – you guessed it – checklists. How to open a file, how to close a file, how to search a trademark, how to draft a patent, and so on.

The first time that I sent a letter to a client, I thought to myself, “I should make a template of this letter, since I’ll need to send it out again.” Today, we have hundreds of these templates. Many templates are for email. We started with Eudora (https://en.wikipedia.org/wiki/Eudora_(email_client)) templates (“.sta” files), which morphed into HTML files when we switched to Gmail, and them morphed again into PHP templates when we realized that some paragraphs had been duplicated in some email templates. So now, when we need to change a standard paragraph, we update one PHP file, and all of the email templates are automatically updated (since they “include” these standard paragraphs). Clocktower may be the only law firm that you have heard of that uses (hand-coded) PHP as its Content Management System (CMS). For those who like to drill down, we power this system with MAMP (https://en.wikipedia.org/wiki/MAMP).

In 2021, after 20 years of physical offices, and as a result of the COVID-19 pandemic, Clocktower went virtual. So while the physical libraries no longer exist, the virtual ones persist, using the exact same structure as the ones I created 25 years ago.

Over time, checklists got spun out of the procedure manuals (which I call “procs” for short) into more task-specific (plain text) lists. Such as how to do billing, how to create an online event, or how to evaluate a patent application for terminology consistency.

AI And Checklists

This is where the AI industry has some teaching to do. Many AI pundits like to call the things that can be automated “workflows.” I have never ever referred to anything as a workflow. But checklists I know. “TODO” lists I know.

So as Clocktower continues to integrate Artificial Intelligence (AI) into its practice, we think about it as simply automating our “TODO” lists.

And because all of our files are highly organized and internally consistent (since they are also based on templates), automating tasks has become second nature.

So it turns out that, with my obsession for lists, I have been preparing for AI my entire life!

As Conan O’Brien said after Norm Macdonald told his epic moth joke, “My congratulations to anyone who stuck it through to the end!”

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One Reply to “* The Discipline (And History) Of Checklists, Including USAF Pilot Training (Or Why ‘AI Workflows’ Should Be Renamed ‘TODO Lists’)”

  1. [Written 2026-07-16, posted 2026-07-17.]

    Friends of 17 Seconds:

    You may be asking one of the following questions:

    First, why did Erik email this “17 Seconds” newsletter a day early? That, my friends, was a mistake! But congrats if you noticed! The blog posts (https://www.clocktowerlaw.com/6582.html, https://www.giantpeople.com/17860.html) were both scheduled for the correct time and date (17:17 on the 17th, explained here, sort of: https://www.giantpeople.com/4497.html).

    Second, why, in a “17 Seconds” all about lists, did Erik omit “The Legal List,” the book that paid for law school (as well as being Erik’s first successful startup exit) (https://www.giantpeople.com/44.html)? That, my friends, was NOT a mistake! While I am very proud of this book, it’s a “list” in name only and doesn’t really relate to checklists, procedures, and AI “workflows,” which was the main point of this edition of “17 Seconds.”

    So there you have it. Thanks for reading! And how ’bout that Norm Macdonald moth joke!

    -Erik (heels@alum.mit.edu)

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