Tap into hidden wisdom and unlock breakthrough learning—no matter your title. In this dynamic episode, Damon Lembi sits down with Jeff Wetzler, co-founder of Transcend, former Chief Learning Officer at Teach for America, and author of Ask: Tap Into The Hidden Wisdom of People Around You For Unexpected Breakthroughs in Leadership and Life. Jeff unpacks why even the smartest leaders miss crucial insights, how defensiveness blocks learning, and why the answers to your toughest problems are closer than you think. With stories from his own career, actionable tools, and research-backed advice, Jeff shares his Five Step ASK Approach—an adaptable playbook for building trust, surfacing blind spots, sparking genuine dialogue, and designing action plans that actually work. 

From elite leadership traps to the art of high-quality questions, this episode is overflowing with practical wisdom for anyone who wants to lead, listen, and learn at the next level. 

In this episode, you’ll learn: 

• Why top leaders often fail at learning—and how to avoid the “know-it-all” trap 
• The biggest barriers that keep people from honestly sharing what leaders need to hear 
• Jeff’s real-world examples (including his own missteps) and how the ASK Approach could have changed outcomes 
• The Five Steps of the ASK Approach, including: choosing curiosity, making it safe, posing quality questions, listening to learn, and reflecting/reconnecting 
• What quality questions sound like—and how they unlock hidden ideas and energy in your team 
• Actionable prompts and strategies to cultivate trust, safety, and psychological resilience—so people tell you the real story 
• How closing the feedback loop cements learning and strengthens your culture 

Timestamps: 

00:00 – Why high achievers can struggle more with deep learning 

03:15 – The Know-It-All vs. Learn-It-All leader mindset 

04:52 – Jeff’s personal story: missing key signals as a leader 

07:32 – Core barriers that prevent honest feedback (fear, time pressure, lack of psychological safety) 

10:12 – Recent missteps & lessons as a leader 

14:03 – How to signal that you value people’s input 

16:28 – The power of the “What’s your reaction?” question 

19:31 – Why great insights rarely come unprompted—leaders must ask 

20:16 – The ASK Approach: Five steps for breakthrough conversations 

22:31 – Step 1: Choose curiosity—why it’s the gatekeeper to learning 

24:31 – Practical ways to reclaim your curiosity as an adult 

28:27 – Using AI to challenge your own assumptions 

29:29 – Step 2: Make it safe—how leaders build psychological safety 

33:12 – Steps investors and CEOs can take to cultivate candor 

34:36 – Radiating resilience: Showing you can “handle the truth” 

36:38 – Step 3: Pose quality questions (with examples to use) 

39:18 – The trap of “Does that make sense?”—better alternatives 

41:38 – Asking for headlines, digging deeper, and hearing real stories 

42:45 – Step 4: Listen to learn (not just to respond) 

45:12 – Pulling the thread: How therapists and leaders get to the real issue 

45:57 – Paraphrase and test: The magic strategy for clarity and trust 

47:01 – Step 5: Reflect and reconnect—why closing the loop matters 

49:04 – The impact of follow-up and closing feedback surprises 

50:07 – Where to connect with Jeff and get free resources 

50:31 – Damon’s challenge: Go into every conversation ready to learn 

About Jeff Wetzler 

Jeff Wetzler is a seasoned organizational learning expert, co-founder of Transcend, and author of Ask. With over 25 years of experience, including as Chief Learning Officer at Teach For America, Jeff has helped leaders and teams unlock blind spots, build trust, and discover hidden insights that drive performance and breakthrough change. His work blends academic research, real-world consulting, and lived leadership lessons. Learn more on Jeff’s website and connect with him on LinkedIn. 

Resources & Mentions: 

• Jeff’s website: askapproach.com 
• Jeff’s book: Ask: Tap Into The Hidden Wisdom of People Around You 
• Jeff on LinkedIn: linkedin.com/in/jeffwetzler 
• Craig Dowden (mentioned): LinkedIn 
• Tools referenced: Ladder of Understanding, AI tools: ChatGPT, Claude, question storming methods by Hal Gregersen & Marilee Adams 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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