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The StoryBrand Podcast

#74: How to Ask for the Sale Without Sounding Pushy

The StoryBrand Podcast

StoryBrand.com

Business, Marketing

4.72K Ratings

🗓️ 1 June 2026

⏱️ 42 minutes

🧾️ Download transcript

Summary

Believing in what you sell is one thing. Asking someone to pay for it is another. When it's time to talk price, follow up, or close the deal, everything starts to feel awkward. So you wing it, avoid the hard questions, and hope the customer decides on their own. But hope is not a sales strategy. What if selling could feel less like pressure and more like helping someone cross the finish line?

 

In this week's episode, Donald Miller talks with Jonny Holsten, CEO of Bridge Selling and author of Fix Your Broken Sales Calls. Jonny explains why so many sales conversations fall apart and shows you how to guide buyers through a simple "bridge" from pain to purchase. You'll learn how to ask better questions, qualify without sounding rude, present the right solution, and close the sale without the cringe factor. Listen in to learn how to make sales feel clear, helpful, and a lot less awkward.

 
 
 

Ready to clarify your message and grow your business?

 

Attend StoryBrand Your Business LIVE to learn how to explain what you do in a way customers instantly understand:
https://storybrand.com/live/?utm_medium=podcast&utm_source=podcast&utm_campaign=sbyourbusiness&utm_term=sbpod&utm_content=SB_workshop 

 

Visit StoryBrand.com for business training, messaging tools, and resources to help you grow:
https://storybrand.com/?utm_medium=podcast&utm_source=podcast&utm_campaign=storybrand&utm_term=sbpod&utm_content=SB_home 

 

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Transcript

Click on a timestamp to play from that location

0:00.0

The three mistakes that I see the most, these will make a seller feel very uncomfortable.

0:05.0

It'll also create a bunch of revenue leakage. Invisible leakage in your sales, winging it.

0:10.0

Going into a conversation with no game plan. The second is measuring the wrong things,

0:16.0

looking at number of conversations and close rates as opposed to measuring the substance or the quality of

0:22.7

that conversation. And the third thing is we don't practice. You go into like a large professional

0:28.5

sales organization and they're having weekly sales trainings. Yet most small businesses, that's not

0:35.1

always feasible. So they end up practicing only when money's on the

0:39.5

line. They go into a big sale. Having not practiced, the words you're going to say. That's, you know,

0:44.8

like rolling out a big marketing campaign without having anyone proofread it. Those are the things I see,

0:50.1

winging it, measuring the wrong things, and then just simply not practicing until you're on an

0:54.5

actual deal.

0:56.7

If you've ever struggled to explain what your business does or you felt like your marketing

1:01.9

should be converting better, then join us for Storybrand Your Business Live.

1:05.9

It's a two-day workshop here in Nashville.

1:08.4

It's happening September 1st through 2nd where Donald Miller himself will teach you how to

1:13.5

build clear messaging that works.

1:16.1

And at the event, you'll also get direct feedback from Storybrand certified guides.

1:20.4

So your message finally connects with customers.

1:23.4

All of this year's workshops have sold out.

1:25.5

So don't miss your chance.

1:27.4

Register for the Story Brand Your Business Live event happening September 1st through 2nd at

1:32.4

storybrand.com slash live.

...

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