The Art of Asking Smarter Questions

Recently, I discovered another interesting article from Harvard Business Review. I am not really a fan of this magazine. But they tend to select trendy topics that generate interesting discussions, in my opinion. I can thank Hilton Barbour, a contact newly added on Linkedin, to let me discover this article. I appreciated him emphasizing the importance of better questions in this era of AI with easy answer. He’s so right saying that “questions are going to be the mechanism to unlock creativity and innovation.”

I also appreciate that the Harvard Business Review recognises that the best questions in an organization may be the ones that often go unasked. A few lines before, it says leaders must be attentive to avoid sensitive topics… This got me thinking. It is the scope of the last component of their framework, the “subjective questions”. Is this really solved with questions? Probably not without a very human leadership in my opinion.


“It’s not a matter of asking lots of questions in hopes of eventually hitting on the right ones.”

I highlight this statement for my part. Their practical framework of questions investigative-speculative-productive-interpretive-subjective is definitively worthwhile, I have no doubt. But I would say it might miss something related to completeness. This is the “Collective Exhaustive” part of the beloved MECE principle of these McKinsey folks. How do you ensure you will provide this “big picture” going through the framework? Is a standardized approach feasible?



I don’t have an answer, unfortunately. My method is intuitive and based on feeling. Faced with the uncertainty of a task, I imagine myself in a sort of dark cave, lighting torches by answering a set of diverse questions. These questions must be based on availability in terms of information/knowledge, while being as speculative as possible. Obviously, knowledge scope is both acquired and the potential through continuous learning. I don’t attempt to meticulously illuminate every corner of the cave, but rather aim to sense its boundaries. Once I have this feeling in a reasonable time, I am generally capable of defending a proposed solution, showing a feasible path, while revealing some potential potholes. Obviously, if it appears useful, I will have dug deeper into certain aspects.
This is then refined through fruitful debates with peers. No, this is definitively not a scientific methodology, even if the outputs will be as rational as possible. But is there really a systematic method to move forward in the unknown?

I suspect there will be always a part of feeling, i.e. subjectivity in problem solving, even with a practical framework made of diverse questions. This reminds me this irresolvable “disconnection between the observers and the observed fueling a crisis of meaning today”.


More questions than answers, but isn’t that the journey? Feel free to share your insights or approaches by mail or Linkedin—I’m eager to explore different viewpoints and learn from diverse perspectives!



More questions than answers, but isn’t that the journey?



(last picture taken from https://septennial.wordpress.com/tag/torch/, thanks! this is what I had in mind, other pics from the HBR article with link above)

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