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Curated Questions

Celebrating The Power Of Questions

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#103 Ken Woodward: The People Who Leave Get the Last Word: Revisiting a Question Ten Years Later

"What do former members say about the organization?" - Ken Woodward

Ten years ago today, I asked a question on my daily practice, IOTD365: what do former members say about an organization? I wrote it after my daughter gave up on an internship. One conversation in a hallway with a senior who'd done it was all it took.

In 2016 I read that question as an insider asking leaders to listen. Today I read it as a former member who left federal service after thirty-two years without anyone asking what I knew. I also read it as a founder who can't hear what's said after I leave the room.

In this episode, I reread the original post and question the man who wrote it. I look at where reputation really lives and the courage it takes to tell someone the truth. Then I borrow a habit from my years navigating submarines in and out of port. Taking a fix on an old question shows how far I've moved.

What question did you answer years ago that deserves a second look?

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

Be sure to subscribe to the weekly Curated Questions Dispatch newsletter for more fun with questions and curiosity! (https://substack.com/@curatedquestions)

Keep questioning!

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tags: Curated Questions, Ken Woodward, revisiting questions, asking better questions, organizational reputation, former employees, exit interviews, employee feedback, workplace culture, climate survey, leadership listening, organizational learning, institutional knowledge, speaking up at work, workplace courage, internship, career reflection, leaving federal service, Navy veteran, submarine navigation, taking a fix, self-reflection, personal growth, journaling practice, Insight of the Day, IOTD365, reputation management, founder lessons, listening to feedback, curiosity
categories: Leadership, Strategy, Coaching, Critical Thinking, Innovation, Legacy, Problem Solving
Wednesday 09.30.26
Posted by Kenneth Woodward
 

#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!

Read more

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
 

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