2 min lesson

What to extract from the answers

Match each case in "What to extract from the answers" to the signal and response that fit it.

What to extract from the answers

Pain to quantify

Payments PR-to-merge cycle time, onboarding ramp for new hires and the review backlog the principals complain about.

Pick one you can baseline and re-measure in a pilot.

Risks to surface

Data-retention exposure, shadow self-serve seats outside SSOSingle Sign-On. One company login (usually via SAML or OIDC) instead of a separate password per tool. Press Enter for the full definition. and the credibility scar from the Copilot rollout.

Name them before the platform team does.

Success criteria to lock

One headline metric the VP Eng named, plus the principals' merge conditions.

Written down and agreed, so the pilot can pass or fail honestly.

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Full explanation

The discovery summary you send back

Within a day, you send a short confirmation note. It proves you listened and converts spoken answers into a shared, correctable record. If you got something wrong, this is where they fix it for free.

Discovery summary - send within 24h

Subject: Northwind x Cursor - what I heard, please correct

The decision: by end of Q2, a go/no-go on standardizing AI-native
development, evidenced by a scoped pilot - not a seat purchase.

The pain we'll baseline: payments PR-to-merge cycle time (currently
~3.5 days median, per the squad) and new-hire ramp-to-first-merge.

Hard gates (platform): zero-data-retention required, SSO/SAML
mandatory, SCIM deprovisioning + admin audit before any expansion.

The skeptics' bar: principals will merge AI-authored code only if it
passes existing review + tests with no drop in defect rate.

Success = cycle time down, no governance regression, two principals
shift from skeptic to neutral-or-better.

Open unknowns: confirmed champion, budget ceiling, security-review
lead time. Proposing we close these next session.

Watch out

The failure mode of this section is pitching disguised as questions. “Don't you think faster reviews would help?” is a pitch. “Where does a change wait longest between idea and prod?” is discovery. If your notes are full of Cursor features instead of their facts, you ran a demo with a question mark on the end.

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Advanced table

Objections you should expect - and your live response

Objection (live): “We already pay for Copilot - why add another tool?”
Your move: Ask what Copilot usage actually is. Low adoption is the proof, not the counter-argument: the mandate didn't change behavior, so a measured pilot on real pain is the cheap way to learn what would.

Objection (live): “Legal will never approve a tool that sees our code.”
Your move: Agree the bar is right, then name it: zero-data-retention, no training on their code, model routing they control. Offer to bring the platform team the exact security posture before any expansion.

Objection (live): “Our principals think AI writes bad code.”
Your move: Don't defend AI. Convert it: “what would have to be true for you to merge an AI-authored PR?” Then make the pilot prove exactly that, with their review gates intact.

Objection (live)	Your move
“We already pay for Copilot - why add another tool?”	Ask what Copilot usage actually is. Low adoption is the proof, not the counter-argument: the mandate didn't change behavior, so a measured pilot on real pain is the cheap way to learn what would.
“Legal will never approve a tool that sees our code.”	Agree the bar is right, then name it: zero-data-retention, no training on their code, model routing they control. Offer to bring the platform team the exact security posture before any expansion.
“Our principals think AI writes bad code.”	Don't defend AI. Convert it: “what would have to be true for you to merge an AI-authored PR?” Then make the pilot prove exactly that, with their review gates intact.

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Optional practice

Practice: What to extract from the answers

QA Northwind principal engineer says “AI writes bad code - Copilot proved it.” You are mid-discovery. What is the strongest move?

What to extract from the answers

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