Interview Insights
- Mike DiGregorio

- 6 days ago
- 1 min read

Interview Question
"Tell me about a time you identified an opportunity to improve a process or product by taking a calculated risk. What data or intuition led you to take that chance, what was the outcome, and how did you manage the potential downside? 💡🎲"
Purpose of the Question
This question is designed to separate "order-takers" from value-creators by assessing three specific traits:
Critical Observation: It reveals whether the candidate is paying enough attention to their environment to spot inefficiencies or untapped opportunities rather than just following the status quo.
Analytical Risk Assessment: The "calculated" part of the question is key. It shows if the candidate uses data, pilot testing, or stakeholder feedback to mitigate risks before jumping in.
Entrepreneurial Mindset: It highlights a candidate’s bias for action and their ability to take ownership of an idea from conception through execution, regardless of their formal job title.
This question is perfect for identifying "intrapreneurs"—employees who drive growth from within the organization.




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