Friday - June 5th, 2026
Apple News
×

What can we help you find?

Open Menu

The Question Asked in the Wrong Room | Ken Woodward #78

  1. The Question Asked in the Wrong Room | Ken Woodward #78 22:24

“Those scripts are not Wisdom. They are load-bearing walls for other people’s power.” – Ken Woodward

Every room has a question nobody asks. Sometimes that’s a failure of courage. Sometimes it’s something else entirely, a hierarchy so explicit it pre-sorts who is permitted to speak before anyone opens their mouth.

In this episode, Ken reflects on a $100M federal acquisition program derailed by a senior stakeholder who wielded disruption as a weapon. The question that could have changed the outcome existed. It just never reached the person who needed to hear it.

Drawing on that experience, a chance conversation with a Vietnamese businessman named Kien, and the current civic moment, Ken explores why we swallow necessary questions, and what it costs us when we do. He offers a ladder of micro-courage for asking harder questions at every level of power, from the private to the public square.

One braver question. That’s the practice. That’s where it starts.

Fellow pilgrims, this one’s for the rooms we’ve all been in.

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!

In March 2025, I wrapped up 32+ years working for the US Navy (Active Duty, Contractor, Civil Servant) and am now developing three elements (podcast, coaching, and speaking) of the Curated Questions project. Keep up with all the action at www.curatedquestions.com and come along for the ride!