06 October 2026
Do They Really Know How to Lead AI Initiatives? How Can You Be Sure?
Inside the Mind of Hiring with Dr. Mickey Fineberg: Business Psychologists Enabling the Selection and Preparation of Great Leaders
About
I was recently asked to assess a COO for a consumer and business data company.
While I typically don’t delve into a candidate’s technical depth, the hiring exec asked me how I might assess the COO’s experience and know-how related to leading AI initiatives. I asked for a little time to think it over and,
perhaps, do some research before getting back to him. Between what I know about experientially qualifying an executive candidate and what I found re: the hiring exec’s question, this is what I advised him (and how I would also advise executive candidates seeking roles that involve AI leadership ).
First I said not to bother asking about specific AI definitions (Machine Learning) or model names (Mem Palace). Instead, I stressed asking the candidate to describe an AI initiative they led (that may or may not be noted on their resume). In that context, ask about specific decisions, trade-offs (improving some aspects while accepting certain costs or risks), artifacts (e.g. the model card that described the project purpose and parameters), project metrics, failures and related adjustments, and their personal role and accountability. A credible exec can explain what they did, why they chose that approach, how they measured results, and their adjustments when the system fell short.
While I typically don’t delve into a candidate’s technical depth, the hiring exec asked me how I might assess the COO’s experience and know-how related to leading AI initiatives. I asked for a little time to think it over and,
perhaps, do some research before getting back to him. Between what I know about experientially qualifying an executive candidate and what I found re: the hiring exec’s question, this is what I advised him (and how I would also advise executive candidates seeking roles that involve AI leadership ).
First I said not to bother asking about specific AI definitions (Machine Learning) or model names (Mem Palace). Instead, I stressed asking the candidate to describe an AI initiative they led (that may or may not be noted on their resume). In that context, ask about specific decisions, trade-offs (improving some aspects while accepting certain costs or risks), artifacts (e.g. the model card that described the project purpose and parameters), project metrics, failures and related adjustments, and their personal role and accountability. A credible exec can explain what they did, why they chose that approach, how they measured results, and their adjustments when the system fell short.