The Learn-It-All Podcast 201: The “Ugly Pond” Sales Strategy Every Pro Needs to Know | Greg Bennett
What if everything you know about sales is about to be turned on its head? In this high-energy episode, host Damon Lembi sits down with legendary sales trainer Greg Bennett to reveal why most pipelines (and salespeople) are headed for extinction in the age of AI. Greg breaks down his signature “Ugly Pond” concept—embracing uncomfortable truths early to build trust, not just chase maybes—and shares why mini steps are the real secret to sales momentum. From the destructive dance between “hopeless romantic” sellers and ninja-level buyers, to the pressure AI will put on lazy pipelines, Greg pulls no punches. Packed with real stories, actionable frameworks, and hard-won wisdom, this conversation is a must-listen for anyone who wants to stay ahead as trust, outcomes, and human connection become the ultimate differentiators in sales.
Whether you lead a team, carry a quota, or just want to future-proof your career, you’ll leave motivated (and equipped) to trade wishful thinking for real results—one “mini step” and honest conversation at a time.
In this episode, you’ll learn:
- Why selling services is dead—and the new playbook is all about selling outcomes.
- What the “Ugly Pond” is, and how embracing “no” early unclogs your pipeline and builds trust faster.
- How AI is exposing lazy salespeople and forcing a new era of transparency and specificity.
- The powerful psychology behind the dysfunctional dance between buyers and sellers.
- The magic of “mini steps”: breaking the sales process into visible, mutual-commitment wins that build confidence, progress, and clarity.
- How to build instant credibility by putting client outcomes first, not product features.
Timestamps:
00:00 – Don’t talk services, talk outcomes: building instant trust
01:17 – The “Ugly Pond” origin: Saying the uncomfortable truth in sales
05:22 – Why facing “no” is the key to real pipeline health
09:24 – The sales dance: Why buyers and sellers deceive each other
11:00 – How AI will crush average salespeople and fake pipelines
15:11 – Building trust fast: Arrive with value for the client
16:28 – Features, benefits, and the power of client-outcome storytelling
20:00 – Hyper-relevance: Why vertical-specific prospecting wins
21:11 – Introducing mini steps: Making invisible sales processes visible
29:52 – Mini steps in action: Why mutual commitments matter
33:17 – Flushing the pipeline: When to pivot, when to press for “no”
35:41 – The “zero to ten” flush: How Greg gets prospects to name the truth
43:47 – Management’s real job: Owning the pipeline and coaching for reality
46:56 – What a good sales day looks like (and why new reps need clarity)
48:45 – Why fundamental sales skills matter more than new tricks
49:16 – A classic San Francisco story with Damon’s father and a surprise celebrity proposal
52:44 – Where to find Greg’s Ugly Pond course and connect for more help
About Greg Bennett
Greg Bennett founded his own sales coaching and consulting firm in 1987, building a career grounded in psychology and human behavior. He’s trained organizations of all sizes—from large, medium and small sales organizations, to national consulting firms, to Fortune 500 giants. His client list also includes over 200 pro and collegiate sports teams, including the NFL, NBA, MLB, and NHL.
Greg is also the author of four books, including Consultative Closing and Make More Donuts.
He officially retired from full-time speaking and consulting in January of 2025, and is now offering occasional webinars, an online program called, "The Power of NO", as well as select 1-on-1 coaching engagements.
Resources & Mentions:
- Greg Bennett on LinkedIn
- The Ugly Pond website & course – Greg Bennett’s training and resources
- Consultative Closing - https://a.co/d/ftiKpzj
- The Challenger Sale book - https://a.co/d/2hJwDWS
- “Make More Donuts” – https://a.co/d/d4iou66
Podcast Contact Information:
Website: www.learnit.com
Email: podcast@learnit.com