Last week, I had the privilege of hosting the inaugural session of Leading With Impact, our Community of Practice for leaders committed to meaningful transformation. It was an inspiring event filled with deep conversations, thought-provoking insights, and, most importantly, great questions.

With the phenomenal Marina Steagall as our keynote speaker, we explored the power of the questions we ask every day. Are we aware of the types of questions that come naturally to us? And more importantly, which questions are missing from our repertoire?

From the five categories of questions: are we asking the right ones?

We used the framework from Harvard Business Review’s ‘The Art of Asking Smarter Questions’ (by Arnaud Chevalier, Frédéric Alsace, and Jean-Louis Barsoux, HBR May-June 2024), which identifies five mutually exclusive, collectively exhaustive categories of questions:

• Investigative: What’s known? - these questions help analyze problems and clarify objectives
• Speculative: What if? - also known as the possibility-based questions, these reframe challenges and push us beyond limiting assumptions
• Productive: Now what? - these drive decisions, actions, and momentum
• Interpretive: So what? - these questions synthesize trends and give meaning to information
• Subjective: What’s unsaid? - these delve into personal feelings, fears, and motivations, aka the human factor

The first four categories focus on content, logic, and analysis and are in a natural order. But the last category, Subjective, stands apart - tapping into emotions, frustrations, concerns, beliefs, expectations, and hidden agendas. This is where the make or break happens for transformations. Because even with the best strategy, even when everything
seems to be aligned, if leaders ignore the human response to change, progress stalls.

What’s missing from our question mix? During our session, we ran a ‘What’s Your Question Mix?’ survey. As a trained theoretical chemist, I expected my Subjective score to be on the lower end. It wasn’t my highest, but surprisingly, it wasn’t my lowest either.

What shocked me was this: for almost no one in the room was Subjective their highest-scoring category! And for many the lowest scoring.

We had a diverse group of leaders: HR executives, CEOs, operations leaders – all people whose roles revolve around human dynamics.

And yet, the most human category of questions -the ones that probe emotions, motivations, and personal stakes- was consistently underutilized.

That got me thinking.

Are we forgetting to ask the human questions in the age of AI?

AI is shifting our focus from having the right answers to asking the right questions. It drives a paradigm shift from seeking answers to seeking questions, with prompt engineering quickly becoming an essential skill. But in our excitement for AI’s capabilities, are we losing touch with the very thing that makes us humans human?

Are we forgetting to ask: How do we feel about this? What do we want? What is your concern about this transformation? Why does this growth plan make you feel uncomfortable? What must change to make you feel better about it? What needs to be added to make it digestible?

For years, I’ve believed AI would make work more meaningful and humans more human. But now, I’m wondering: do we love AI so much that we’re starting to mimic it, becoming more machine-like ourselves?

A challenge for all of us.

To circle back: if AI is optimizing our ability to ask precise, productive questions, shouldn’t we double down on the Subjective ones?

My husband once said, ‘She doesn’t need January 1st to make resolutions.’ So here’s my new resolution, starting today: I will ask at least three Subjective questions in every
relevant conversation.

Now, I challenge you: what will you do to keep the human factor alive in the age of AI?