MySalesDay | Human-Centered Selling: Process, Empathy, and a Little Bit of Unreasonable

Description

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.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

I’m Michael Hess, Founder and Chief Seller Advocate of “My Sales Day”, and it's my job to make “the sales life” "less messy" for you...and of course, to help you excel and perform at your peak abilities.

My goal is to make your time here educational, inspirational, and actionable. And yeah, entertaining too…sales doesn’t have to be boring! Selling is fun too, so let’s have some of that here as well.

You'll get skill ideas, action items, and hugs.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

Description

Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose.

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

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

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Description

Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose.

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

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

Description

Human-centered selling requires more than just closing deals — it means understanding people, showing empathy, and leading with purpose.

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

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

About MySalesDay

Sales is hard...brutally hard.

And it's messy.

My Sales Day is a podcast BY Sellers, FOR Sellers.

Yes, hugs.

You need support and you don't often get it from inside your org, and you certainly don't get it from the street.

The goal of this show is that you walk away with ideas, confidence, and a whole lot of skip in your step.

And if you need more of this positivity in your sales day, be sure to read the MySalesDay email which you can get by subscribing at mysalesday.io.

Hosted by Ausha. See ausha.co/privacy-policy for more information.

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