Tell me about a time you were 75% through a project and realized the strategy was wrong.

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Anonymous · Accepted Answer

💬 Question: How do you ensure that the strategy is sound before starting a
project?

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⭐️ Answer: I validate strategy through three gates: problem clarity, business
alignment, and feasibility confidence. I don't move forward until all three are
solid.

Problem clarity: I start by talking directly to users or customers—not
stakeholders. For Ellis AI at CBRE, I ran structured interviews and design
thinking workshops with enterprise researchers to understand their actual
workflow friction, not what leadership thought the problem was. I mapped the job
they were trying to do using JTBD analysis. If I can't articulate the problem in
one sentence and explain why it matters to the business, the strategy isn't
ready.

Business alignment: I define the North Star metric and leading indicators before
writing a single requirement. For Ellis, I decided the North Star was adoption
rate—not just usage—because the business needed to prove AI ROI across multiple
business units. I then worked backward: what product capabilities drive
adoption? What data do I need to measure it? What does success look like in 6
months versus 18 months? I aligned engineering, data science, and business
stakeholders on this metric framework using RICE prioritization to sequence the
roadmap.

Feasibility confidence: I pressure-test the technical and operational
assumptions with engineering and data teams early. Can we actually retrieve and
rank documents accurately at scale? What's the latency risk? What's the cost?
For Ellis, I built a small prototype with the data science team to validate that
hybrid retrieval and reranking could improve accuracy by 25% before committing
to the full roadmap. That prototype became the evidence I needed to move
forward.

The key tradeoff is speed versus certainty. I don't wait for perfect
information, but I do wait until the risk is contained—either through evidence,
a small experiment, or a clear rollback plan. If I'm wrong about the problem or
the metric, I want to know in week two, not month six.

Tell me about a time you were 75% through a project and realized the strategy was wrong.

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