What happens when you stop playing by the rules and start asking better questions? Where’s the line between healthy dissent and chaos — and why do the best leaders welcome a little pushback?

Psychologist and researcher Dr. Todd Kashdan joins us to make the case for principled insubordination — and why compliance culture kills innovation. We’re breaking down how to lead curious teams, challenge bad ideas without blowing things up, and create the kind of environment where the smartest voices aren’t the quietest ones.

KEY TOPICS

• Why curiosity is inefficient — and why that’s a good thing.
• The danger of compliance culture in leadership.
• When “too agreeable” becomes your company’s biggest risk.
• The art of asking better questions (and why most people don’t).

SUBSCRIBE

https://www.youtube.com/@decidedlypodcast?sub_confirmation=1

CHAPTERS

(00:01) When rebels outperform rule-followers

(01:19) Skipping the meeting — and still winning

(02:05) The problem with obedience culture

(05:56) Why Dr. Kashdan left Wall Street for psychology

(07:13) Anxiety, self-awareness, and bad leadership

(08:36) Purpose as a cure for social anxiety

(10:51) Social skills we lost during COVID

(13:47) Are we overusing the word “bullying”?

(14:42) You need stress to build strength

(16:07) Why popular kids sometimes peak in high school

(17:36) The confidence gap nobody talks about

(19:30) Why honest feedback is so rare

(22:17) Sarcasm, teasing, and intimacy

(25:03) How curiosity actually builds connection

(29:43) Don’t Google it: The social power of not knowing

(32:42) Curiosity vs. the shortcut mindset

(34:41) The link between curiosity and memory

(36:17) Why some people just aren’t curious

(38:24) Curiosity is inefficient — and that’s the point

(40:14) The risk of staying “safe” in leadership

(43:58) The freshman year lesson that changed everything

(45:47) Tailoring leadership to your team

(47:46) Smart rebels vs. loose cannons

(49:24) When curiosity backfires at work

(51:20) Why some employees stop sharing ideas

(53:29) How to disagree without blowing things up

(56:19) The decision-making checklist your team needs

(58:09) Defensive pessimism: The plan B mindset

(60:05) Dr. Todd Kashdan's top decision-making tip for business owners

CONNECT WITH US

⁠www.decidedlypodcast.com⁠

Instagram⁠: @decidedlypodcast

Facebook⁠: https://www.facebook.com/decidedlypodcast

Shawn’s ⁠Instagram⁠: @shawn_d_smith

Sanger’s ⁠Instagram⁠: @sangersmith

Thank you to Shelby Peterson of Transcend Media for editing and post-production of the Decidedly podcast.

SANGER’S BOOK

A Life Rich with Significance: Transforming Your Wealth to Meaningful Impact⁠: https://www.amazon.com/Life-Rich-Significance-Transforming-Meaningful/dp/1952654769

SHAWN’S BOOK

Plateau Jumping: What to Change When Change Is What You Want⁠: https://www.amazon.com/Plateau-Jumping-What-Change-When-ebook/dp/B0CTXHP5HR

MAKING A FINANCIAL DECISION?

At ⁠Decidedly Wealth Management⁠, we focus on decision-making as the foundational element of success, in our effort to empower families to purposefully apply their wealth to fulfill their values and build a thriving legacy.

LEARN MORE: ⁠www.decidedlywealth.com⁠

WEEKLY NEWSLETTER https://visitor.r20.constantcontact.com/manage/optin?v=001aeU_pPBHJPNJWJBdVbaci6bjGIuEJurH12xHBWDEVT_NxyCadMd7wLSZjcEZglkSjDjehuIbTHD8nABOIdV69ctfYpSzg24RCIytetBUrlIPPKgaGzjGZ8DkM0Wp1LMjbErcYUur7PbZGjeVo4gyXlz821AoJGZR⁠

CONNECT WITH DR. TODD KASHDAN

Newsletter: https://toddkashdan.substack.com/about

Website: https://toddkashdan.com/

The Well-Being Lab (download articles here!): https://toddkashdan.com/well-being-lab/

Linkedin: https://www.linkedin.com/in/toddkashdan

Instagram: @toddkashdan

X: @toddkashdan

Facebook: https://www.facebook.com/public/Todd-Kashdan

Psychology Today Blog: psychologytoday.com/blog/curious

Books: https://toddkashdan.com/books/