Describe the most ambiguous assignment you have had. How did you turn it into a plan?

How to answer

“Most ambiguous” invites a story about chaos; the second half of the question matters more: where the ambiguity became a plan, and the evidence that changed it. The Pragmatic Engineer reported, in August 2025, that Colin Jarvis, then OpenAI’s head of forward deployed engineering, said what customers describe in scoping often does not match the data and system reality, so his team biases toward moving fast and re-scoping to the most useful thing it can do. ^[1]Source 1What are Forward Deployed Engineers, and why are they so in demand? (Gergely Orosz)PublisherThe Pragmatic EngineerSource typenews report The re-scoping is what this question tests.

1. The brief, quoted. “Use our sensor data for something.” Then name what was missing: an owner, a metric, the data, or agreement on the problem.
2. The owner and the decision. Whose decision would change if the work succeeded, and how you found them. A vague brief often has a sponsor but no owner; naming one is the first piece of the plan. Quote the question that found them: “Which decision would someone make differently next month if this worked?”
3. The questions that changed the work. Only those whose answers changed what you built, with the answers.
4. The assumption you made instead of asking. Say it as you said it then, with the date you would check it.
5. The first small deliverable. What it was, when a user saw it, and why that slice.
6. What it exposed, and the plan before and after. This is the center of the answer.
7. The result, and what you chose not to build.

Say out loud when you stopped asking, and why the remaining unknowns were cheap to check by building.

The trap is an answer that is all process: interviews held, documents written, and a plan that never changed. If nothing altered the plan, the listener concludes the assignment was not ambiguous or you were not listening.