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

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: [email protected]

Follow us on LinkedIn and Instagram for more updates.