Among the questions we routinely ask executive contributors during the development of executive perspective pieces, one produces genuinely strong, differentiated content more reliably than any other we've tried: asking them to describe a significant decision related to their company's AI strategy that they'd make differently if given the chance again.
Why this specific question produces stronger content
Most executive contributors arrive with a comfortable, pre-formed narrative about their company's AI strategy success, and a direct question about a past decision they'd revise forces genuine, in-the-moment reflection rather than a rehearsed summary they've already delivered elsewhere.
What the strongest answers tend to include
The most useful responses identify a specific decision point, explain what assumption at the time turned out to be wrong or incomplete, and describe concretely what they'd do differently given what they now know - a structure that produces genuinely instructive content for readers navigating similar decisions themselves.
Why executives are often willing to answer this candidly
Framed as a forward-looking reflection on lessons learned, rather than as an admission of failure, this question gives contributors a comfortable and professionally safe way to be genuinely candid about a real misstep, which is usually the most valuable part of the resulting piece.
Why we keep returning to this question
Across many executive perspective pieces, the answer to this specific question has consistently produced the most concrete, useful, and differentiated material in the final piece, more reliably than any other single question in our standard interview approach.