Mystery Gift Box #036 | 40+ Questions to Help You Make Better Decisions

Hey friends,

The five enemies of questioning.

Fear. Knowledge. Bias. Pride. Time. We all know the importance of asking thoughtful questions at the right time in order to make the best decisions. Yet we are never taught how to be a better questioner…

The Book of Beautiful Questions provide over 200+ questions in the area of decision-making, creativity, connectivity, and leadership. Here are some key questions from the book that you can ask yourself in order to make better decisions:

General Questions for Better Thinking

1. How can I see this with fresh eyes?

2. What might I be assuming?

3. Am I rushing to judgment?

4. What am I missing?

5. What matters most?

Four Questions to Check Your Biases and Beliefs

1. What am I inclined to believe on this particular issue?

2. Why do I believe what I believe? (jugular question)

3. What would I like to be true? (desirability bias)

4. What if the opposite is true? (debiasing experts)

Four Questions to Assess your Intellectual Humility

1. Do I tend to think more like a soldier (defending) or a scout (exploring and discovering)?

2. Would I rather be right, or would I rather understand?

3. Do I solicit and seek out opposing views?

4. Do I enjoy the “pleasant surprise” of discovering I’m mistaken?

Five Questions to Detect B.S.

1. How strong is the evidence?

2. What are they not telling me?

3. Does it logically flow?

4. What is the opposing view?

5. Which of the conflicting views has more evidence behind it?

Five Questions to Open Up a Closed-Ended Question

1. How can I “open up” the question to be decided?

2. What is the great, the good, and the ugly?

3. If none of the current options were available, what would I do?

4. What is the counterintuitive choice?

5. What would an outsider do?

Six Questions to Overcome Fear of Failure

1. What would I try if I knew I could not fail?

2. What is the worst that could happen?

3. If I did fail, what would be the likely reasons?

4. … and how would I recover from that failure?

5. What if I succeed — what would that look like?

6. How can I take one small step into the breach?

Six Questions to Ask Before Taking That Job

1. Can the little person rise to the top?

2. How does the organisation react to mistakes? Will I be punished for exploring?

3. Can I have influence in this organisation?

4. How have others here added to their skills?

5. Does this place encourage camaraderie?

6. Will I enjoy the “small pleasures” of my daily routine?

Six Questions to Help Find your Passion

1. What is my tennis ball — the thing that pulls you?

2. What makes me forget to eat?

3. What did I enjoy doing at age 10?

4. What are my superpowers?

5. In what way do I wish the world were different?

6. What is my sentence? (Who are you and what are you aiming to achieve?)

⛰ 4-4-4 Exploration Project

January 2023: Writing and Storytelling (Subject) ✅

February 2023: KURIOS – Cabinet of Curiosities (Cirque Du Soleil — Experience) ✅

March 2023: 28 Days of Cold Exposure (Subject and Experience) ✅

April 2023: Complete Growth / Product Marketing Course (Subject) 🟧

📚 This week, I finished reading…

Have interesting gems you want to share with me and others? Share it by replying to this email and I will include it in the next gift box :)

With love,

Ryan O. 🎮

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