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Tracks›Claude Cowork
L2Lesson 8Free

Ask for source-backed questions

Expose what the files do not answer

After this, you'll be able to create a source-backed question list and use it to make Claude's work with local files safer and easier to verify.

Before you start

Complete Compare versions without losing the thread first.

The idea

Good file work tells you what the files do not answer yet. This lesson asks you to make a source-backed question list, not a broad promise that Claude can use files. The output should be specific enough that you can inspect what Claude read, what it produced, and what still needs review.

Open evidence gaps hover above a rack of blank source slots, with one gold review dot waiting beside the rack.
Open evidence gaps hover above a rack of blank source slots, with one gold review dot waiting beside the rack.

Here is the before and after: Before, Claude fills gaps so the answer feels done. After, it lists questions tied to missing, conflicting, or weak source material. For example, a client folder might include notes, drafts, exports, and old versions. The lesson output should say which files are in scope, which are out, what Claude is making, and how you will prove the result came from the right source.

Now try it: Ask for questions before the final answer and decide which ones block the output. Make one choice before asking Claude to work: folder, file set, output shape, source check, access path, or maintenance rule. That choice keeps desktop file work from becoming vague local search.

Ask for source-backed questions runtime mapThe folder workflow works when a source-backed question list connects the input, the check, and the next step.
Messy inputThe raw desktop files material before the lesson shapes it.
a source-backed question listThe thing you can inspect, edit, and reuse.
1Review checkThe source check that catches a weak assumption.
Next stepThe output moves into the next lesson instead of sitting alone.

The lesson is done when you can show the source boundary, the output, and the check that proves the output is safe to use.

Try it (15 min)

Watch out for

  • Treating every question as a blocker.
  • Letting Claude answer from general knowledge when source is missing.
  • Skipping owner assignment.

Paste this into Claude

Using this source inventory and task: [paste], create a source-backed question list. For each question, include Why It Matters, Source Gap, Blocks Final Output?, Who Can Answer, and Suggested Next Step.

If any input is missing, ask me up to three questions before producing the artifact. Then return five sections: Finished Artifact, Realistic File Example, Assumptions To Check, What I Should Use In The Next Lesson, and One Risk If I Trust This Without Fixing It. Keep the answer practical enough that I can paste it into my folder workflow notes.

Created by potrace 1.16, written by Peter Selinger 2001-2019 What a good response looks like

Finished Artifact:
- a source-backed question list
- Why it matters: it gives the folder workflow a concrete thing to inspect instead of a vague intention.
- Use it next: paste this artifact into the next lesson before asking Claude to write, build, import, publish, or review anything.

Reality Check:
- The artifact names the user, input, decision, owner, or proof it depends on.
- The weakest assumption is visible.
- The next step can be completed in one sitting.

Created by potrace 1.16, written by Peter Selinger 2001-2019 What good looks like

  • Questions are tied to source gaps.
  • Blockers are separated from nice-to-have questions.
  • An owner is named for each blocker.
  • Next steps are included.

Created by potrace 1.16, written by Peter Selinger 2001-2019 Go deeper (8 min)

Paste this into Claude

Without rereading the lesson, explain why a source-backed question list matters in three bullets. Then apply it to a second file example: [describe a different folder or document set]. Return What Changed, What Stayed The Same, What To Check Before Trusting The Output, and the exact next action.

Created by potrace 1.16, written by Peter Selinger 2001-2019 What a good response looks like

Transfer Check:
- What changed: the second example has a different audience, input, or delivery context.
- What stayed the same: a source-backed question list still needs a source, a review check, and a next step.
- Before trusting it: inspect the source check that would catch a wrong assumption.
- Next action: run the check once, then carry the revised artifact into the next lesson.

Created by potrace 1.16, written by Peter Selinger 2001-2019 What good looks like

  • You explained the lesson idea from memory before applying it again.
  • The second example changes the artifact instead of copying the first answer.
  • The trust check names a real risk.
  • The next action can be done in one sitting.

When this breaks

  • Fails when gaps are filled with guesses because file work should expose uncertainty.
  • Breaks when blockers are not separated because the owner does not know what must be answered first.

AI can help with this

Paste the exercise prompt into Claude with your real folder or file context. Ask Claude to interview you one question at a time, produce a source-backed question list, challenge the weakest assumption, and rewrite the artifact once so it is ready for the next file step.

Each gap docks into a matching source slot before it becomes a review item.

Created by potrace 1.16, written by Peter Selinger 2001-2019 You can now

✓

You can point to a source-backed question list.

  • ✓You can explain which files are in scope.
  • ✓You can name the assumption that still needs checking.
  • ✓You can use the output in the next lesson.

Key takeaways

Source-backed questions make the final output more honest and easier to finish.

  1. 1Questions should point to source gaps.
  2. 2Blockers need owners.
  3. 3Non-blockers should not stop all work.
  4. 4Final output should wait for true blockers.

Created by potrace 1.16, written by Peter Selinger 2001-2019 Go deeper

  • Claude file uploads

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