201: The “Ugly Pond” Sales Strategy Every Pro Needs to Know | Greg Bennett
Greg Bennett, legendary sales trainer and author, joins The Learn-It-All Podcast to break down why the future of sales has no room for fluff, false hope, or feature lists. In this high-impact conversation, host Damon Lembi and Greg get brutally honest about what’s killing sales pipelines—and what actually works in the AI age. From his signature Ugly Pond philosophy to his “mini steps” framework, Greg shares how to build trust faster, move deals forward, and cut through the noise with relevance and realness.
Read the full breakdown of Greg Bennett’s episode on Learnit.
Key Leadership Lessons from Greg Bennett’s Journey:
Stop selling services—start selling outcomes. Greg challenges the old playbook and shows how trust skyrockets when you lead with results, not features.
The “Ugly Pond” builds better pipelines. Embracing rejection early unclogs sales cycles, eliminates wishful thinking, and frees up time for real opportunities.
Mini steps = major progress. By breaking the sales process into mutual micro-commitments, reps gain confidence, clients gain clarity, and deals move forward.
Connect with Greg Bennett:
Website: https://theuglypond.com/
LinkedIn: Greg Bennett
Books:
Greg’s work has transformed the sales performance of over 200 pro sports teams and Fortune 500 companies. Now semi-retired, he continues to coach top performers through his online program and one-on-one engagements.
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