The Art of Asking Questions

Unlock the Secret to Unparalleled Professional Success

I have persistently asked questions for 20 years. 2004 was the year when I intentionally started building the habit of asking questions and pursuing mastery of this skill.

While I haven’t exactly tracked how many questions I have asked, they comfortably run into the hundreds of thousands. Sometimes, my journaling is actually a sequence of questions and more questions to tease out the insights I am seeking.

I had started practising the Socratic method of learning about things even before knowing the term existed. This found me peeling back layers of understanding by answering questions with even more questions.

Questions once led me off social media for 5 years and even more questions kept me totally occupied throughout that period until I found I had drilled down to the first principles of major chunks of the human experience. These questions distilled answers as wisdom that has impacted tens of thousands of people and counting across the globe. During the COVID-19 pandemic, for instance, I taught a MOOC with 1500+ participants from all over the world some of these things you are about to come across in this playbook.

Questions have served me. Good questions have served me well. Great questions have flung open doors of opportunity to me. I have been the youngest in many rooms but it only made my insights more staggering and that led to even more doors of opportunities opened to me.

I have taught PhDs and legal luminaries these skills. Medical practitioners, engineers, business moguls have listened to me with rapt attention. One of them, after going through a one-week course with me, attended a similar session at the foremost business school in Nigeria. He said, “Your class was by far better than what they served us here! They weren’t even close!” Another, a Senior Advocate of Nigeria and one time Chief Justice of one of the Southwestern states said after I had taken his entire chamber through a critical thinking course that was built around asking questions, “We have been having sessions like this; matter of fact, we had [one of the top finishing schools in Lagos, Nigeria] take us last year. But it is evident that you teach this because you have deeply practiced it while theirs was like a textbook exercise.”

This is my natural habitat. Constructing questions that help me unlock new insights to do great things, to transform the world, to make history.

And now, for the very first time, I have distilled these years of unlearning, learning and relearning how to ask strategic questions into this playbook "The Art of Asking Questions: A Failproof Guide to Career and Professional Excellence." It will change your life. I promise you. The content that makes up this playbook changed the life of one of the PhD students I once trained. She became an Assistant Professor in record time. In one of the foremost universities in New York, USA.

It’s your turn. 

Are you ready?