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How you organize the Library matters more than which structure you pick. Any folder structure works well, as long as each folder is specific enough that you (and the AI) can point at exactly the right one when searching.

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The rule: subfolders over mega-folders

  • Keep folders under roughly 20 files. When one grows past that, split it into subfolders.
  • Folders within folders is good. A mega-folder with 100+ files is not.
  • Why: when a search is scoped to a folder (see the Prompting Guide), a small, specific folder means the AI reads only the relevant files, so answers come back faster, more accurate, and easier to verify.

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A proven example

The rest of this page is the structure Sweetspot recommends as a starting point: five top-level folders, each with a single job. Adopt it as is, or keep your own layout and apply the same rule.

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01_Company-Identity

Who you are: the facts and approved language every proposal draws from.

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02_Past-Performance

Your contract execution record only: proof of what you’ve done. One folder per contract, named {"{Agency}_{Program}_{Contract#}_{YYYY-YYYY}"}.

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03_Proposal-Library

What you wrote: submitted proposals only, never edited after close-out, plus a curated reference folder of excerpts worth reusing. Name each proposal folder {"{YYYY}_{Agency}_{Sol#}_{ShortTitle}"} plus the outcome: WIN, LOSS, NO-AWARD, or PENDING.

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04_People

The team: one trusted source for resumes and credentials.

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05_Teaming-Partners

Partner materials only: never mixed into Past Performance, Proposal Library, or People. One folder per partner.

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Why the example works

  • One job per folder. When each folder holds one kind of content, the AI (and your teammates) always know where to look, and where new files belong.
  • Names carry the facts. Contract numbers, date ranges, and win/loss outcomes in folder names make search results self-explanatory and let you scope AI requests precisely: “search the 02_Past-Performance folder for cloud migration work.”
  • Submitted work stays frozen. Separating the never-edited record (03_Proposal-Library) from reusable excerpts (_Reference-Content) means you can reuse confidently without corrupting the archive.
  • No folder gets huge. Every branch bottoms out in small, specific folders, which is the rule that makes everything else work.