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Curated Questions

Celebrating The Power Of Questions

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#60 Radhika Dutt: From Goals to Puzzles: How Questions Outperform OKRs in Real Teams!

"We vote with our labor for the world we want to create. If you don't reflect on what you're doing, how do you know you're casting the right vote?" - Radhika Dutt

In this episode of Curated Questions, host Ken Woodward engages entrepreneur and author Radhika Dutt in a profound exploration of how questions can transform organizations from goal-driven to puzzle-solving entities. Radhika is the author of "Radical Product Thinking" and shares her journey from MIT to becoming a serial entrepreneur to developing the puzzle-based leadership OHLA framework (Objectives, Hypotheses, Learnings, Adaptations).

The conversation reveals how traditional goal-setting, rooted in 1940s assembly-line thinking, fails in today's complex environment, where creative problem-solving matters more than repetitive execution.

Radhika demonstrates through a live experiment how "puzzles" energize while "goals" burden, explaining that puzzles tap into internal motivation rather than external pressure. She emphasizes the critical importance of reflection, a practice she credits with enabling better decision-making both personally and professionally.

Drawing from her nine languages and global experience, including living in post-apartheid South Africa, Radhika offers insights on creating psychological safety for questions across cultures. The episode culminates with practical guidance on implementing puzzle-based thinking in organizations, showing how asking better questions leads to ownership, engagement, and transformative results.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

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tags: Curated Questions, Ken Woodward, Radhika Dutt, goals vs puzzles, OKRs, puzzle thinking, radical product thinking, reflection practice, psychological safety, leadership development, asking better questions, problem framing, product strategy, curiosity mindset, organizational learning, decision making, innovation leadership, team culture, effective questioning, corporate transformation, AI product slop, strategic reflection, business innovation, human-centered leadership, continuous learning, team engagement, adaptive leadership, complex problem solving, mindset shift, product leadership
categories: Leadership, Mental Wellness, Personal Growth, Creative Thinking, Innovation
Wednesday 12.03.25
Posted by Kenneth Woodward
 

#54 Jill Reilly: The Permission Paradox & Why Questions Matter More Than Approval!

"The most fundamental relationship in any change process is the one that you have with yourself. It's the questions that you ask yourself first and foremost that are the game changers." - Jill Reilly

In this episode of Curated Questions, host Ken Woodward is in conversation with global citizen and author Jill Reilly to explore the power of questioning in navigating life’s complexities.

Jill shares her journey from the Midwest to South Africa, Zimbabwe, and beyond, reflecting on her experiences as an aid worker and the lessons that shaped her understanding of change and personal agency.

They discuss the importance of self-permission, processing grief, and the need to adapt amidst societal and technological upheaval. With insights from her new book The Ten Permissions: Redefining the Rules of Adulting in the 21st Century, Jill emphasizes the transformative potential of asking the right questions to unlock personal growth and resilience.

This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.

Keep questioning!

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tags: Ken Woodward, Curated Questions, Jill Reilly, permission, questions, approval, self-permission, personal agency, curiosity, life transitions, career change, South Africa, cultural intelligence, adult learning, mindset shift, breaking patterns, family expectations, authentic connection, willpower, being willful, navigate uncertainty, AI age, future of work, personal growth, self-discovery, questioning techniques, life choices, global citizen, aid worker, The 10 Permissions, transformative questions, personal boundaries
categories: Community, Social Impact, Connection, Leadership, Listening, Personal Growth, Change Management, Problem Solving
Wednesday 10.22.25
Posted by Kenneth Woodward
 

#35 Shelbie Morgan: When You Show Up for Yourself, Your World Changes

In this Curated Questions episode, host Ken Woodward is in conversation with Shelbie, who emphasizes the importance of showing up for oneself, making empowered decisions, and the value of financial literacy. They discuss her upbringing, shaped by strategic parenting and mandatory volunteering, and how these experiences cultivated her confidence, empathy, and strong work ethic. The conversation explores the importance of structured freedom, the power of serving others, maintaining financial awareness, and the impact of manifesting goals and self-belief. Shelbie's insights highlight the vital questions to ask oneself to achieve both personal and financial growth. Tune in for actionable advice on harnessing your full potential and building a successful, balanced life.

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tags: Ken Woodward, Curated Questions, Shelbie Morgan, showing up for yourself, self advocacy, financial literacy, entrepreneurship, manifestation, vision boards, structured freedom, volunteerism, curiosity, confidence building, decision making, money mindset, budgeting tips, subscription audit, emergency fund, business ventures, authentic self, personal growth, mindset shift, strategic parenting, service to others, kindness matters, passion activation, grit development, corporate america, side hustles, wealth building, self investment, peace and value, betting on yourself
categories: Leadership, Coaching, Listening, Mentoring, Personal Growth, Innovation, Strategy
Thursday 06.12.25
Posted by Kenneth Woodward
 

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