12 Self-Directed Questions To Help Improve How You Think

Did I ever tell you that I have various notebooks where I collect questions? It’s a practice that I picked up many years ago, doing so sharpens my thinking, helps me ask better questions and enables me to extract insights from conversations. The rule is simple: ask better questions to get better answers.

There are many categories of questions directed at situations, people, and other things. But the ones directed at yourself are the most interesting ones because they’ll enable to question yourself; your beliefs, perceptions, assumptions, thoughts and thinking patterns.

In 2019, after I shut down my emotion AI startup, I put myself through some deep, rigorous questioning about my motivations, beliefs, thinking patterns, perceptions and assumptions. I do this anytime something doesn’t go as I want it to, and usually leads to some hard truths.

Nobody likes being questioned. Much less, not many people question themselves. But, doing so will help you figure out the truth about yourself; and that is very liberating.

“The key to wisdom is this — constant and frequent questioning, for by doubting we are led to question, by questioning we arrive at the truth.” – Peter Abelard

Ask yourself these 12 questions to help sharpen your thinking

So, sticking to the topic of “thinking better“, I came across Thomas Oppong’s 12 Questions for rigorous thinking while scrolling through my Medium recommendations. I found the 12 self-directed questions he proposes very useful:

  1. Am I holding on to convention beliefs for too long and are they still helping me become a wiser version of myself?
  2. How many of my immediate connections are independent-minded? Conventional thinkers think alike. For rigorous thinking, break the chain.
  3. When was the last time I had a rational conversation with multi-disciplinary thinkers? Embrace cross-domain thinking.
  4. Are the books I read on the same topic? Reading books outside your usual scope can broaden your knowledge and expand your working memory.
  5. Do I read biographies? Make time to get into the heads of intelligent people by reading good books that talk about their habits, routines and experiences.
  6. Am I curious enough? Rational scepticism encourages rigorous thinking — question almost every common sense.
  7. What habits, behaviours, routines and beliefs control my judgements? Are they all accurate and objective? Can they be improved? Remember what Einstein said, “Insanity is doing the same thing over and over again and expecting different results”.
  8. Am I unconsciously forcing myself into a fixed mindset? “The first principle is that you must not fool yourself, and you are the easiest person to fool,” Richard Feynman said.
  9. Do I easily discount knowledge I disagree with? Our blind spots can easily lead us to make wrong conclusions. Keep an open mind.
  10. Do I look for answers at the same places? We tend to rely on the same set of information to make judgments. Start considering places/information you usually ignore.
  11. Have I considered all the possible choices and outcomes? Think first, second, third and fourth-order consequences of your decisions.
  12. When was the last time I changed my mind? Learn to change your mind when you find new knowledge that proves your existing beliefs, models and perceptions were wrong.

These questions are about questioning your habits, choices, perspective and mindset; the things we do on a daily basis. Do it, let me know what answers you get and what you plan to do about it.