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Program Execution & Driving Without Authority1 / 3

2 min lesson

Escalate with a recommendation, not a problem

Work through this: "Your weekly status has read green for a month and now the program is suddenly red and will miss its date. What does that pattern tell you about your operating cadence and what would you change?"

Step 1 of 3

Escalate with a recommendation, not a problemmake the decision easy

Cursor's leaders are time-poor and founder-engaged. Dropping a raw problem on them - “Finance and Infra disagree on attribution” - costs them the work of diagnosing it. Bring the decision pre-chewed.

  1. 1State the decision needed in one line. “We need to pick the source of truth for billable inference by Friday.”
  2. 2Give the two or three real options, each with its cost and consequence, not a strawman and a favorite.
  3. 3Make your recommendation and say why. You're closest to the data; have a point of view.
  4. 4Name the deadline and what happens if it slips. Tie the decision to the date it puts at risk.
Say it like this

“Decision needed by Friday: pick the source of truth for billable inference - our telemetry or the Finance ledger. They disagree on how retried requests are counted, and the attribution model is blocked until we choose. Option A: adopt the Finance ledger as truth - clean audit story, but we lose per-request granularity and showback slips a week. Option B: keep telemetry and reconcile to the ledger monthly - we keep the granularity but own a recurring reconciliation and a known variance. I recommend B: per-request detail is what makes the routing decisions defensible, and a stated monthly reconciliation is cheaper than rebuilding attribution later. If we don't land this by Friday, the showback pilot slips and the target date moves with it.”

Close the loop on every risk

A risk register earns its keep only if every entry resolves to one of three states: mitigated (you took action and it's handled), accepted (leadership chose to live with it, on the record) or escalated (it's now a decision in someone else's hands). A risk that just sits “open” for six weeks is a risk you're pretending to manage. Driving each one to a verb is the discipline interviewers are listening for.