236: The Ask Approach: How to Lead with Curiosity (Not Control) | Jeff Wetzler
Release Date:
October 28, 2025
Release Date: Oct 28
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.
What 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
In This Episode:
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”
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.
