About this episode
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
