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- How do you decide team boundaries and ownership models as an organization scales?
- What indicators tell you a current structure is limiting execution?
- How do you turn company strategy into an engineering plan over the next 12 to 18 months?
- How do you balance platform investments against product feature delivery?
- How do you build a strong bench of Engineering Managers and senior IC leaders?
- What is your approach to succession planning for critical leadership roles?
- What planning and review cadence do you use to keep multiple teams aligned?
- How do you handle quarterly goals when priorities shift mid-cycle?
- How do you reduce cross-team dependency drag in a growing engineering org?
- Describe a time you unblocked a high-impact initiative with many stakeholders.
- How do you assess whether commitments are realistic before they are announced?
- What interventions do you use when one area consistently misses commitments?
- How do you set engineering standards without centralizing every decision?
- How do you evaluate when architecture choices should be standardized across teams?
- How do you partner with Product leadership on sequencing and scope for strategic initiatives?
- How do you resolve tradeoffs between user impact, technical debt, and reliability?
- What org-level mechanisms do you use to improve quality and incident outcomes?
- How do you measure engineering effectiveness beyond output volume?
- How do you calibrate hiring bar across different teams while preserving local context?
- What changes have you made to improve hiring signal and reduce bias?
- How do you ensure performance reviews are fair, specific, and actionable?
- How do you identify and coach high-potential leaders early?
- How do you reinforce accountability and ownership without creating fear?
- What cultural anti-patterns do you actively watch for in scaling orgs?
- How do you communicate engineering tradeoffs to non-technical executives?
- What does a strong monthly executive update from engineering include?
- How do you approach headcount planning and prioritization during constrained budgets?
- Tell me about a time you had to do more with less without burning out teams.
- Describe a major organizational or technical change you led and how you made it stick.
- How do you maintain trust during periods of uncertainty or reorganization?
- What are your expectations of the VP/CPO partnership in this role?
- What outcomes would define a successful first six months?
- What questions do you have about our strategy, org shape, or leadership expectations?