Mystery Gift Box #039 | 30+ Questions to Help You Become a Better Leader

The best hidden gems I've found; interesting ideas and concepts, thought-provoking questions, mind-blowing books/podcasts, cool animes/films, and other mysteries ❤️

May 28, 2023

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 become a better leader:

Questions to ask to see if you are ready to be a leader

  1. Am I willing to step back to help others move forward?

  2. Do I have the confidence to be humble?

  3. Can I learn to keep learning?

Questions to figure out what type of leader you are

  1. Who are my formative influencers?

  2. When have I been at my best?

  3. When have I come up short — and why?

  4. What have I taken a stand for (and against)?

  5. What is my story about being a leader?

Questions to clarify your mission and why

  1. If we disappeared tomorrow, who would miss us?

  2. What do we do that others can’t or won’t?

  3. What are we against?

  4. How might we be not just a company but a cause?

Question to sharpen your leadership focus

  1. What is the one thing I can do that would make everything else easier / unnecessary?

  2. What should we stop doing?

  3. What do I want to go big on?

  4. Which stupid rule should we kill?

  5. At this moment, what is the best use of my time?

Questions to establish your vision

  1. How can we become the company that would put us out of business?

  2. How can we embrace ourselves for the third wave?

  3. If an oracle could tell us about our business five years from now, what would we ask?

  4. What would the seventh generation think about what we’re doing?

  5. How might I make tomorrow visible?

  6. What is our “vision question”?

Questions to ask to inquire and problem solving

  1. What’s the biggest challenge you’re facing?

  2. Are you making progress?

  3. Help me understand what led to…

  4. Is it clear what we’re doing and why?

  5. How can I help?

Questions to encourage a culture of safe questionings

  1. How can we make it safe to question?

  2. How might we make questioning rewarding?

  3. How might we make questioning productive?

  4. How can we make a culture of inquiry stick?

⛰ 4-4-4 Exploration Project

Each month, I would explore one new thing; a skill, a subject, or an experience.

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…

Polysecure: Attachment, Trauma and Consensual Nonmonogamy eBook : Fern, Jessica: Amazon.co.uk: Kindle Store

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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