Questions: The Holy Grail of Decision-Making

“What use is knowledge if there is no understanding?” — Joannes Stobaeus

If there was one challenge worthy of some paranoia, Stobaeus’ question captures it for me. Amidst all the noise of modern living, I worry if our minds are ready to infer the accuracy of information and the relevance of knowledge. I worry about the unwieldy beast that is our modern Information Age — which could just as easily be called the Disinformation Age. I worry if my children and future generations will be prepared to tame that beast.

Whether my worries manifest as anxiety epidemics, total anarchy, or just an inability to experience joy from acquiring wisdom — all would be a sad outcome for humanity.

Still, my optimism remains — and was boosted by the most frequent questions I received in response to “The Uncertainty Paradigm: A Playbook for High-Stakes Decision-Making.” The questions were regarding the principle of Inquiry.

Why do questions about Inquiry inspire optimism? It indicates a shared curiosity regarding a principle that I believe is essential to the evolution of decision-making.

Within “The Uncertainty Paradigm,” I describe Inquiry as a principle we apply by converting ideas, opinions, dogma, and “facts” into questions. But the goal is not just to ask any question. It’s to ask high-quality questions. To gain mastery over the science, and the art, of Inquiry.

So, how can we become Inquiry gurus? We’ll get to that shortly…first let’s be clear why it is so valuable.

Inquiry accomplishes two things:

1. Decreases the noise of our minds so we can detect signal, or clarity
2. Increases curiosity and our hunger for clarity

My foremost goal is not to convince anyone what Inquiry is. It is far more useful to know what it is not — and to have curiosity about what it could be.

If Inquiry were a map, it would NOT be one of cities, states, or even earth — it would more likely resemble a map of the universe. Inquiry does not guide us to answers or known destinations — it does, however, guide us to waypoints along a journey into uncertainty.

Inquiry is intended to generate clarity. We mustn’t get answers and clarity confused. An answer is like a plane landing — clarity is a plane taking off. Answers close our mind and create cognitive biases. Clarity opens our mind and inspires the imagination.

Here is a simple example comparing bad vs. good Inquiry:

• Bad Inquiry: Is it true?
• Good Inquiry: How is it true?

I suggest Inquiry become our most beloved and protected principle for decision-making. Societies are built on systems that value answers more than they do questions. We can counterbalance this inequity — and our decision-making will thank us for it.

By making Inquiry part of our values system, we can undo some of the mental programming and biases in our minds’ software. More importantly, we can reduce the need for future generations to undo the same.

In his book, Teaching as a Subversive Activity, Neil Postman shined a light on several challenges within education systems. Notably, he described how “Children go to school as question marks and leave school as periods.”

Some might say that modern education systems have made progress on this topic. However, when we consider that Neil Postman published the aforementioned book in 1969 — and he wasn’t alone in drawing attention to these systemic issues over the past several decades — I argue we have not made enough progress.

Debating the need to evolve modern education systems is not for this writing. My intent is to convey a far simpler point: Most of us alive today were not raised in systems that adequately exercised our Inquiry muscles.

Which brings us back to the question posed at the beginning: How can we become Inquiry gurus?

Like any worthwhile endeavor, it requires energy. There are many methods for investing that energy and acquiring such mastery. Here is my suggestion:

• Step 1: Make Inquiry a value
• Step 2: Practice Inquiry daily
• Step 3: Become a collector of questions

Step 1 and Step 2 require a simple choice and commitment, which I hope is inspired by what has been shared thus far. Step 3, on the other hand, requires us to know what a high-quality question looks like — and what it does not. For why would we want to collect shitty questions? (Don’t answer that.)

One common characteristic of Inquiry, or high-quality questions: They rarely push us to choose the fastest and easiest option. So — if we ask a question and the clarity it generates makes us comfortable and uninspired — that’s an indicator of a bad question.

Peter Thomson said, “Ask yourself the easy questions and you’ll have a hard life. Ask yourself the hard questions and you’ll have an easier life!”

With that wisdom in mind, Inquiry is served when we embrace the concept of delayed gratification. Inquiry ought to be thought of as an investment. The kind from which we’re prepared to wait for its value to appreciate.

As another common characteristic: Inquiry inspires successive questions. If a question doesn’t lead to more questions, it’s typically a bad one. Which is not to say bad questions should be immediately thrown in the proverbial shitcan.

The process of reframing and reworking a bad question can itself be a source of clarity, and lead to high-quality questions. The example from earlier demonstrates how to reframe questions: Don’t ask, is it true — ask instead, how is it true?

With the above in mind, we can think of questions like pieces of art we collect. Therein lies another intent for this writing: To provide questions I’ve found valuable for all variety of decision-making. Mastering Inquiry is within all our reach — and being inspired by high-quality questions contributes to our journey of mastery.

Without further ado, I’ll let the questions speak for themselves:

1. What is this circumstance or emotion teaching me?
2. Do I need more information, or do I simply need to act on the information I have? (Avoiding paralysis by analysis)
3. Before it happens, how can I prevent it? If it happens, how can I recover?
4. How is this uncertainty constructive? (Constructive = ways we can control and reduce uncertainty)
5. In this situation, what advice would I give to someone I care about? Can I accept and apply my own advice?
6. If ______ occurs, how can I/we/they weather the storm and recover stronger? (Assessing the Anti-Fragility factor)
7. How is this analogous? How isn’t this analogous?
8. Ask your higher wisdom, is it not true that without worry you would have arrived exactly where you are now, just more pleasantly?
9. What consequences would we rather be associated with? (Helpful for deciding what risks to accept when only unattractive options exist)
10. How else could I be spending my finite time? How are those activities more valuable? (Assessing Pareto Principle)
11. How do the benefits of ______ outweigh the risks?
12. In 20 years, how would I have hoped to respond to the situation or decision I’m facing right now?

(New questions are periodically added at the bottom of this article.)

It matters little what system we use for collecting questions. Just have one, and make it easy to access. What works for me is a Note on my iPhone, simply titled “Questions.” When I hear or read a high-quality question — whether from James Clear, Tim Ferriss, Tom Bilyeu, Gavin de Becker, or anyone for that matter — I add it to the Note.

If I can serve as part of your system, I’d be honored to have this writing bookmarked — and to have questions forwarded to me. I will be the curator and periodically republish this writing with new questions added to the list above. Email me at bryan@niederhelm.com.

What better way to close than with a quote from Albert Einstein, a true Inquiry guru:

“I have no special talent. I am only passionately curious.”

Addendum Questions (updated 12/5/23)

1. What other ways can we produce the same outcome?
2. What’s one decision you can make today that will save you from making ten more decision in the future? Make the choice that eliminates other choices. — James Clear
3. What do I want this to mean?
4. Do you want to be the most interesting person in the room, or the most interested?
5. How is my biology affecting my thinking about this situation?
6. What would I regret more, this or that? Why?
7. What do you get when you squeeze an orange? Orange juice. Why? Because that’s what is inside. What do you want to come out when somebody or something squeezes you? (Paraphrased from Dr. Wayne Dyer)
8. Six months from now, what do you wish you had spent time on today? — James Clear
9. Define ______? (When someone uses a word that can be interpreted several ways. Seek clarity before responding.)
10. What is not being said? (Six Listening Concepts: Patterns, Omissions, Innuendos, Generalizing, Emphasizing, Catastrophizing)
11. Is the solution to this challenge one of art, science, or both?
12. Is this decision a marathon or sprint?
13. How does this decision move me closer to, or farther away from, the long-term outcome I want to produce?
14. What assumptions am I making about this situation? What assumptions are helpful to guide immediate decisions?
15. Look around the rooms where you spend the most time. What behavior does this space encourage? How can you set things up to make your good habits easier? — James Clear
16. What would ________ do? (insert a mentor, hero, sage, etc.)
17. Aside from my thoughts, am I okay? — James Clear
18. Is this an obstacle to go through or around? How is it under my control or not?
19. If we ask Earth to choose either humans or Artificial Intelligence, which would it pick? How can we behave so it wants to choose both?
20. We often behave as our best selves in the presence of people with whom we’re not close. How can we behave the same around the people with whom we’re closest — our family and dear friends — those most deserving of our best selves?
21. How does an astronaut keep experiencing fulfillment after completing a mission to the moon?
22. Would we rather be right or _______? (Insert: great, better, honest, relevant, etc.)
23. What are three examples of ______? What are three more examples? (easy prompting of ChatGPT)
24. How will the best solution be generated? Going deep, going wide, or both?
25. Fair inequality, or unfair equality?
26. How might we be confusing our interests with our position? (Negotiations)
27. Where is/was the point of diminishing return?
28. During this day, week, month, year — how do I need to work ON the business, and how do I need to work IN the business?
29. Is this decision ready-aim-fire, or ready-fire-aim?

Inquiry Models:

Byron Katie’s four questions of self-inquiry, known as “The Work”:

1. Is it true?
2. Can I absolutely know that it’s true?
3. How do I react when I believe that thought?
4. Who would I be without that thought?

Debrief:

• What worked?
• What didn’t work?
• What’s wanted or needed?