2 min lesson
Sequence your first two quarters
Walk through "Sequence your first two quarters" in order, then name the proof that tells you it worked.
Step 1 of 2
Sequence your first two quarters
Expect “what would you do in your first 90 days and the quarter after?” Don't lead with reorgs. Lead with understanding the existing contracts and where reliability is actually at risk.
- 1Quarter one, weeks 1–4: learn the system in the code. Read the auth, webhook and agent-backend services; sit on-call; map the real SLOs and the top incident sources. Ship one small fix to earn credibility.
- 2Quarter one, weeks 5–12: stabilize the riskiest path. Pick the one Core Service most likely to cause an outage and harden it - idempotency on webhook delivery, token rotation, backpressure on the agent queue - with the team, not over them.
- 3Quarter two: invest in contracts and impact. Tighten the service boundaries between product surfaces and infra, pay down the debt you've now seen and start hiring against the gaps the first quarter exposed.
- 4Throughout: keep shipping. Stay in the code enough that your architecture calls are grounded in the current system, not last year's mental model.
“We were debating whether to build our own webhook delivery layer or extend the managed queue we had. I pushed hard for managed at first - less to operate. Then we modeled the failure semantics and found the managed option couldn't give us per-tenant ordering and idempotency without a fragile shim. The evidence moved me: I changed my recommendation to a thin in-house delivery service on top of the queue, scoped to the minimum that gave us the guarantees we actually needed. I was wrong about where the cost was - it was in the semantics, not the ops.”
Use a changed-my-mind story to cover technical direction and truth-seeking at once. A senior architecture call where new evidence reversed your position is the strongest single answer in this round, because it proves you can both make the call and update it - which is exactly the judgment a player-coach EM is hired for.
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Full explanation
Full explanation
Don't propose a first-90-days reorg and don't assert Cursor-internal architecture facts you can't support to the people who built it. Frame your roadmap as hypotheses to confirm in the code - “I'd want to verify how revocation propagates today” - because honest curiosity survives the follow-up and a confident wrong claim ends it.
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Optional practice
Practice: Sequence your first two quarters
QHow should you answer 'what would you do in your first 90 days as EM of Core Services'?