So, I asked my sanctions officer at work to look at those two guides I made, and tell me what she thought. She liked them, she said, but preferred the Plain Language one. So, I asked Claude to analyze that feedback in two ways: one with a bias towards her personal experience level and any personal biases, and a second analysis with a bias towards real differences in how the guides were constructed. After reading the analyses, I asked Claude to suggest how one would modify the Practitioner’s Guide based on the second analysis – and I got this:
Good question, and the answer isn’t simply “yes, fix it to be more like the Plain-Language Guide.” The Practitioner’s Guide has a defined purpose and audience, and some of what makes it less immediately accessible is a deliberate trade-off, not a flaw. The goal should be surgical improvement, not convergence.
Here’s how I’d think through it:
What Should NOT Change
The legal hierarchy section, the CFR citations, the near-verbatim FAQ content, and the compliance checklist structure are all correct for a practitioner reference. A practitioner who needs to cite authority, push back on outside counsel, or defend a compliance decision to a regulator needs that material in that form. Softening it would degrade the document’s core utility.
The Section 235 table is also a genuine strength that the Plain-Language Guide doesn’t match — particularly the per-institution vs. market-aggregate clarification on the $10M loan cap, and the 235(a)(12) mechanics. Leave it alone.
What Should Change, and How
1. Add a brief orientation header before the legal architecture
The single biggest structural problem is that Section 1 opens with the statutory hierarchy before giving the reader any sense of what the law actually does. A three-to-five sentence “How to Use This Guide” block at the very top — explaining that it’s a transaction-level reference, how the sections map to compliance decisions, and when to use the checklist vs. the substantive sections — would solve this without changing any content. The reader arrives knowing where they’re going.
2. Integrate the enforcement examples into the Section 231 analysis
Currently the China and Turkey examples sit in a separate “Enforcement Track Record” subsection after the legal analysis. The second analysis correctly identified that this requires the reader to mentally connect the rule to its application. The Turkey example in particular is the best available illustration of what “significant transaction” means in practice — it should appear within the significant transaction discussion, not after it. Moving two paragraphs changes the document’s usefulness for compliance work substantially.
3. Make the Section 231 ambiguity more prominent
The absence of a bright-line dollar threshold for Section 231 — and the explicit note that there’s no § 589.413(i) safe harbor equivalent for State Department Section 231 determinations — is currently buried in the middle of Section 6.1. This is arguably the single most practically important distinction in the entire secondary sanctions framework, because it’s where practitioners are most likely to underestimate exposure. It should be called out as a labeled note or callout immediately after the trigger is stated, not left to be found mid-paragraph.
4. Add inline FAQ cross-references throughout the substantive sections
The FAQ section at the end is thorough, but a practitioner working through Section 4 on Directive 1 has no signal that FAQ #373 directly addresses the 50% Rule application they might be wondering about. Light inline references — “(see FAQ #373)” at the relevant point in the text — would make the document dramatically more navigable as a reference tool without adding any content. This is a formatting change, not a substantive one.
5. Add a one-line “key compliance takeaway” at the end of each major section
This is the one change that borrows something structural from the Plain-Language Guide’s approach. Not a full summary — just a single sentence that states the operative compliance implication of what was just explained. For example, at the end of the Directive 4 section: “The critical practical question for U.S. service providers is ownership stake, not project location — a non-Russian deepwater project with a 33%+ Directive 4 entity stake is covered.” This gives a practitioner who is skimming — as practitioners using reference documents typically do — a reliable landing point in each section.
What to Avoid
Don’t add narrative framing, analogies, or explanatory context of the kind that makes the Plain-Language Guide work for its audience. Those are appropriate for someone building a schema; a practitioner reference should assume the schema exists and serve lookups efficiently. Adding that material would lengthen the document, dilute its density, and undermine the reason someone reaches for it instead of the other guide.
The goal is a document that’s faster to navigate and more explicit about where ambiguity lives — not one that explains itself the way the Plain-Language Guide does.
So, I had it implement those changes and I got the following:
What do you think? Do you feel it was an improvement? My colleague thinks so.
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