Most small businesses have no idea what software they are licensed for. Not through dishonesty — through growth: PCs bought at different times, a departed employee's setup nobody documented, a subscription on a personal card. This checklist gets a company of five to fifty people from “no idea” to “documented and deliberate” in one sitting.

Step 1: Inventory what is actually installed (60–90 minutes)

Make a sheet with a row per machine. For each, record: Windows edition and license channel (run slmgr /dli — it takes ten seconds), Office version and how it is licensed (File → Account in Word), plus any paid tools (billing, design, antivirus, browser extensions). Do not skip the machine everyone forgot in the storeroom — it is licensed to something.

Step 2: Match installs to proof (30 minutes)

For every paid item, locate the evidence: delivery email, invoice, order-history entry, or the subscription's admin page. Three outcomes per row:

  • Matched — install and proof line up. Done.
  • Unproven — it is installed and probably legitimate, but no paperwork exists. Flag it.
  • Unlicensed — a copy someone activated with “a tool,” a single-user license running on four PCs. Flag in red.

Step 3: Fix the red flags — cheapest first

  1. Over-installed licenses: uninstall from the extra machines or buy the missing seats. Retail Office keys are cheap enough that this is rarely painful.
  2. KMS-tool activations: replace with genuine keys. Beyond the legal exposure, these machines often have update and security side effects.
  3. Personal-account entanglements: licenses redeemed to an employee's personal Microsoft account walk out the door with them. Migrate to business-controlled accounts as machines get reinstalled.
Tip: fix forward, not backward. You cannot un-run last year's unlicensed install; you can make every machine from today onward clean. Auditors and vendors respond very differently to “we found it and fixed it” than to shrugs.

Step 4: Set three standing rules

  • One folder (or account) holds all license records. Delivery emails forwarded to licenses@yourcompany, or a shared drive folder. New purchase → record lands there the same day.
  • New machine = licensed machine. Windows and Office are part of the setup checklist, not an afterthought when a trial expires mid-invoice.
  • Departure checklist includes licenses. Reclaim transferable licenses and note where each one went next.

Step 5: Spend deliberately going forward

With the inventory in hand, patterns appear: machines that should standardize on one Office version, subscriptions nobody used since March, an OEM-heavy fleet where the next hardware refresh will silently delete licenses. Decide per category — perpetual vs subscription, Pro vs Home — using real usage, not defaults. Our comparison guides on this blog cover each of those decisions in depth.

When the checklist surfaces gaps to fill, the store supplies genuine Windows, Office and business-software licenses with instant email delivery — and buying them all in one place means Step 2 is just your order history at /account.