Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose.
In this episode, Doug Weaver, Founder and CEO at Upstream Group, joins me to share the timeless lessons he’s learned from decades of teaching and practicing sales. From a creative career-defining win at Allure Magazine to decades of training top sellers in digital media, connected TV, online audio and ad-tech space, Doug argues for a return to authentic, process-driven selling rooted in curiosity and courage.
Doug and Michael talk about the threat and promise of AI in sales, why the best sellers are “a little bit unreasonable,” and the importance of closing the gap between sales behavior and real human behavior.
Join us as we discuss:
[3:58] Pivoting from overcoming objections to making the human connection
[9:09] Why the sales game has been losing the human touch and the AI conversation
[22:06] Not just taking “yes” for an answer and the current state of sales skills
Check out these resources we mentioned during the podcast:
The Challenger Sale: Taking Control of the Customer Conversation by Matthew Dixon and Brent Adamson
For more My Sales Day, subscribe to the inspiring My Sales Day newsletter at mysalesday.io, follow the show on Apple Podcasts, Spotify, or search for “My Sales Day” in your favorite podcast player.
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