Coffee Over Cold Calls: Why Relationship-Based Selling Wins | MySalesDay

Description

Paul Cassar, Head of Enterprise Partnerships at DanAds, joins me to share why relationship-based selling isn’t just a strategy — it’s the secret weapon many sales professionals take for granted.

We share stories that blend humor, hard lessons, and high stakes, showing how listening and authentic engagement can turn casual meetings into massive deals.

From an embarrassing misstep that ended with public criticism to a career-making win that began with a simple chat over coffee, Paul and I unpack why playing it safe won’t cut it in today’s sales world.

Join us as we discuss:

[4:24] When a “smooth” meeting turns into a humiliating disaster
[13:10] Why relationships are your greatest asset in the long-game
[20:34] Finding the courage to get personal and ask tough questions

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

Description

We share stories that blend humor, hard lessons, and high stakes, showing how listening and authentic engagement can turn casual meetings into massive deals.

Join us as we discuss:

[4:24] When a “smooth” meeting turns into a humiliating disaster
[13:10] Why relationships are your greatest asset in the long-game
[20:34] Finding the courage to get personal and ask tough questions

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

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Description

We share stories that blend humor, hard lessons, and high stakes, showing how listening and authentic engagement can turn casual meetings into massive deals.

Join us as we discuss:

[4:24] When a “smooth” meeting turns into a humiliating disaster
[13:10] Why relationships are your greatest asset in the long-game
[20:34] Finding the courage to get personal and ask tough questions

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

Description

We share stories that blend humor, hard lessons, and high stakes, showing how listening and authentic engagement can turn casual meetings into massive deals.

Join us as we discuss:

[4:24] When a “smooth” meeting turns into a humiliating disaster
[13:10] Why relationships are your greatest asset in the long-game
[20:34] Finding the courage to get personal and ask tough questions

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

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