Finally! Asking Questions is Important Again.

I was the bane of my grammar school teachers because I always asked questions that were not part of the lesson plan. As a result, I was told to focus on the lesson at hand, which was frustrating, not to mention boring!

I was not a happy camper in school

Discovery makes life interesting and vibrant. I did not do well academically, but excelled in college when the shackles were removed. Not only did I develop an insatiable thirst for reading and discovering new technologies, but I also got involved in AI in the late 1990s. I founded a consulting business that rewarded me monetarily and personally. A True nerd, I was the envy of my peers when I was the first to have a 10 Megabyte hard drive! “You’ll never run out of space,” they said. As the years progressed, I was one of the first adopters of Lotus Notes, then a bleeding-edge technology.

Lotus Notes = Collaboration / NOT!

I was involved with Lotus Notes from its second release, and my consulting business was focused on application development and infrastructure implementation. I can’t tell you how many executives bought into Lotus Notes because it was a “collaborative technology,” like swallowing a pill; if they bought this software, their employees would magically start to collaborate. You guessed it, didn’t happen!

My technological curiosity, often an obsession, has caused me to stay at the bleeding edge of numerous technologies. While many past technologies were intriguing, today’s AI advancements, like Google’s recent announcements, present a different kind of shift that fundamentally relies on human inquiry.

Ask me a question, anything really AMA!

Today, Google announced yet more and tighter AI integration with its products. I don’t think executives are as naive as their predecessors, and buying Google Workspace bells and whistles will not instantly make your employees more productive. However!

Google’s announcement is important not so much because of the AI bells and whistles but because the mere existence of AI requires humans to ask questions. Why is asking questions key to unlocking this power? Is it because AI’s output is directly proportional to the quality of the input? Is it because we need to critically evaluate AI-generated answers? It’s because asking questions is extremely valuable in and of itself, and adding value is what grows companies, teams, and individuals.

There was a phase where we called this by a fancy name, “Prompt Engineering.” It’s just asking a more beautiful question. Input to an AI requires contextual questions, and that requires considerable forethought. You can ask dumb questions without the fear of being embarrassed by your AI assistant and iterate on that conversation until you reach questions of significance, or think harder and ask better questions.

A More Beautiful Question

I was impressed with Warren Berger’s book A More Beautiful Question, which champions the idea that in a world increasingly saturated with answers, the ability to formulate the right questions is a critical skill for innovation, problem-solving, and driving meaningful change in both professional and personal spheres.

School was focused on having me answer test questions to demonstrate that I understood something. Knowledge and understanding are not about memorizing the right answers. Can we look forward to a resurgence of our childhood curiosity? I sure hope so. Imagine if we valued the individuals with the more beautiful questions over the know-it-alls with all the answers.

In my years at an innovative think tank in Sterling Forest, NY, I learned a valuable lesson. What before How. It sounds simple, but it is profound. Our educational system has conditioned us to have the right answer, and in that rush to be the “smartest person in the room,” we often don’t ask if we are answering the right question.

The author Berger outlines A Framework for Inquiry. He introduces a practical framework for effective questioning, often summarized as a “Why / What If / How” sequence:

  • Why? This stage involves deeply understanding a situation or problem.
  • What If? This encourages imaginative thinking about possibilities and alternative solutions.
  • How? This phase focuses on moving from ideas to action and implementation.

I can’t tell you how many mistakes were made in business because some smartie pants jumped to conclusions “How” without having a clue about “What”.

Back to Google. They have remarkably excellent tools in the Google Workspace. I administered Workspace for over 10 years and was always impressed with the volume of innovation and improvement on the base layer. Docs, Sheets, Chrome, Calendar, Meet, and much more, but today, Google took a giant leap by asking us to ask (AI) questions. This is the most crucial thing if you want your organization to be more productive and innovative, and leverage the power of those foundational tools that Google has been improving over the past 10 years.

To be clear, I am pleased with Google products. Historically, they have been slow on the uptake and mediocre on some aspects of support, but today, they hit a home run. I am certain that the emphasis on asking questions will have a greater impact than any company’s cool software.

For many years, I worked professionally as a “Knowledge Engineer” tasked with uncovering the essential knowledge that industries relied on to be profitable, incorporating this into process reengineering and often automating it in expert systems. While expert system technology fell out of favor because it was too expensive to maintain, and BPR had limited success because office politics often negated any meaningful changes, the core component of Knowledge Engineering, asking questions, produced some of the most valuable and lasting benefits to my clients.

The overarching goal of creating a pervasive culture of inquiry is widely accepted as important, even if its full realization is a continuing journey for many. The most significant benefit of AI may just be that of a teacher who will help us ask better questions.