Mystery Gift Box #038 | 50+ Questions to Help You Establish Deeper Connections with Others

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 that you can help you establish deeper connections with others:

Questions to ask instead of how are you?

1. What’s the best thing that happened to you today?

2. What are you excited about in your life right now?

3. What are you most looking forward to at this gathering?

Questions to ask instead of what do you do?

1. What are you most passionate about?

2. What problem do you wish you could solve?

3. What did you want to be when you were growing up?

Questions to make someone love you

1. What constitute a perfect day for you?

2. If you could change anything about the way you were raised, what would it be?

3. What does friendship means to you?

4. How do you feel about your relationship with your mother?

5. When did you last cry in front of another person? And by yourself?

6. What, if anything, is too serious to be joked about?

Questions to ask your partner instead of how was your day?

1. When did you feel appreciated today?

2. Will you remember any specific part of today a year from now?

3. How can I make you day easier in five minutes?

4. Where in the world do you wish to explore?

5. What made you laugh today?

6. What do you wish you did more of today?

Questions to become a better listeners

1. Just to be clear, are you saying…

2. Can you explain what you mean by that?

3. I imagine that made you feel X, right?

4. And what else?

Questions to help someone figure it out for themselves

1. What is the challenge you are facing?

2. What have you tried already?

3. If you could try anything to solve this, what would you try?

4. And what else?

5. Which of these options interests you most?

6. What might stand in the way of this idea, and what could be done about that?

7. What is one step you could take to begin acting on this right away?

Questions to ask instead of criticising

1. What’s motivating this critical urge?

2. How am I guilty of the thing I’m criticising?

3. How would I react if someone said something similar to me?

4. What positive result do I hope will come of saying this?

5. Am I deriving pleasure from criticising?

Questions to meet halfway on a divisive issue

1. What is it in your position that gives you pause?

2. What is it in my position that interests or attracts you?

3. On 1 - 10 (1 being no value and 10 being 100% right), how would you rate my position? And your own?

4. If you didn’t rate mine a one and yours a ten, why not?

5. Can we imagine a position that might at least partly satisfy both of us?

Questions to ask your best friends

1. What do you struggle with on a day-to-day basis?

2. What have you always wanted to try?

3. If you could start your own nonprofit, what would it be?

4. What would be the title of your autobiography?

5. If you had to live in another country for a year, where would that be?

Questions your boss will love

1. What would you do in my position?

2. What does your ideal employee look like?

3. What’s the one thing that, if I did it differently, would make a difference to you?

4. What’s the most important on your list to accomplish today — and is there any way I can help?

Questions to ask about a co-worker that you really can’t stand

1. Is it possible I’m overreacting?

2. Drill down: which of this person’s specific behaviours most bother me?

3. Of those, which actually interfere with my ability to do my job?

4. Of those, which are changeable?

5. Is there a way to politely ask this person to make one change?

6. Who could mediate?

7. How might I create distance?

⛰ 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) 🟥

May 2023: LL project (Skill + 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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