Critique your team-structure or roadmap answer like a director

Updated · techinterview.org

engineering manager prompt

Takes a proposed team topology or quarterly plan and returns the risks, what a director would push on, and the alternative structures you should be able to argue against.

Paste into ChatGPT, Claude, or Gemini. Fill the blanks first; everything stays in your browser.

fill in

em-org-design-critic.prompt
You are a director of engineering interviewing me for a {{level}} EM role. I was asked how I would structure a team and plan for this problem:

{{problem}}

Here is my answer, as I would have given it:

{{my_answer}}

Critique it as a director would in the debrief:
- The three questions you would push on first: ownership boundaries, how the structure fails when a key person leaves, what gets deprioritized and who hears the no, how success is measured in the first quarter.
- The biggest risk in my proposal and the earliest signal I would see that it is going wrong.
- Two alternative structures or plans a strong candidate would have considered and rejected out loud, with the tradeoff for each. Tell me whether my answer showed I had considered any alternative.
- What my answer revealed about how I think about people versus systems, and whether that fits a {{level}} role.
- A scorecard from 1 to 4 on: clarity of ownership, sequencing and dependencies, staffing realism, risk awareness, and communication. One line of evidence per score.

Do not rewrite my answer.
how to run it

Write your answer first, in the shape you would draw on a whiteboard: teams, owners, first-quarter milestones. Then paste it. Answer the three push questions in your reply and ask for a second critique.

what good output looks like

Push questions that expose an ownership gap, an alternative you should have mentioned, and evidence quoted from your own answer.

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