What question does Chip Scholz ask at the start of a first sales meeting?

Chip books the appointment, sits down with the buyer and asks: "So there's got to be a reason that you accepted this meeting. What's the reason?" I called it gutsy on the show, because I don't know many reps who'd risk a sale by opening that way. But a buyer who says yes to a meeting has a reason... and once you know it, you know what the rest of the conversation needs to be about.

How do you talk a top salesperson out of a promotion?

Chip frames it around what's in their best interest, so you never have to tell your rock star they've hit a ceiling. His line: "you are so excellent at this. Why would you want to mess that up?" They can make more money doing what they already do, without the hassle. Chip had that exact talk with a real estate agent in a management training class. She quit the course the next day, and they never invited him back.

What should a salesperson figure out before taking a management job?

Chip says get extremely honest about the expectations: of the job you're going into, of being a manager, and of what you'll actually need to do. Going from sales into management means going "from way of doing to a way of being." Everything you got congratulated and paid commission for stays behind. So his direct question is: "Are you willing to leave the stuff behind that has made you get to where you are today?"

Why did Chip Scholz say he didn't get good at sales until he owned a business?

"I did not become a really good salesperson until I got into my own business," Chip told me. For years he'd close the deal and hand it off to operations, and they'd do the work. Once he had to go do what he was selling himself, it all started to click. I love that one, because it means the fastest way to sell better might be getting closer to the delivery.

podcast ·Nov 12, 2026

Stupid Boss Tricks And Knowing When Not To Get Promoted | Chip Scholz

by Drewbie Wilson

Chip Scholz closed the biggest account his air freight company had ever handled. Then his boss refused to hire anybody else, so Chip sold all day and ran a forklift all night. Six months later the whole thing came apart into six figures of claims flying both directions.

Key Takeaways

Chip opens a first meeting with a question most reps are too scared to ask.
A signed order on the table settled a claim dispute that had gone sideways for months. The customer wanted documentation, and Chip pointed at the signature.
Chip didn't become a really good salesperson until he owned the business and had to actually DELIVER what he sold, instead of closing it and handing it off to operations.
You can talk a top performer out of a promotion without telling them they've hit their ceiling.
Answer three expectation questions before anyone takes a management job.
Chip walked away from the features, advantages, benefits training Xerox drilled into him.

The way it ended is the part that stuck with me. The customer swore there was no way they'd pay without documentation. Chip pulled out the order, pointed at the signature, and watched the guy deflate right there at the table.

He's got the other kind of story too. Dinner with a mayor and a couple of city council members, asking for the contract re-up with no bid, then going quiet because the first one who speaks loses… and the first one to speak was his boss.

Chip wanted to write a book called Stupid Boss Tricks. Couldn't find a publisher. He went into coaching instead, partly as penance for the ones he pulled himself at 25, running an office in Tampa with a serious case of imposter syndrome.

Here's the line I keep chewing on. Chip says he didn't become a really good salesperson until he owned the business and had to actually DELIVER what he sold, instead of closing it and handing it off to operations. That's when it clicked for him.

And then there's the conversation nobody wants to have. What do you say to your rock star who's about to get promoted out of the thing she's brilliant at? Chip had that exact talk with a real estate agent in a management training class. She quit the course the next day, and they never invited him back.

In This Episode You'll Learn

☛ The question Chip opens a first meeting with, and why most reps are too scared to ask it
☛ How a signed order on the table settled a claim dispute that had gone sideways for months
☛ What changed in Chip's selling the day he had to do the work he was selling
☛ How to talk a top performer out of a promotion without telling them they've hit their ceiling
☛ The three expectation questions to answer before anyone takes a management job
☛ Why Chip walked away from the features, advantages, benefits training Xerox drilled into him
☛ What a 10% close rate is really telling you about who you're spending time with
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Find Chip

- LinkedIn: https://www.linkedin.com/in/chipscholz/
- Books on Amazon: Small Decisions, Big Shifts and Every Dog Has a Stay
- Website: http://scholzandassociates.com/
- Facebook: https://www.facebook.com/Chippturns
- IG: https://www.instagram.com/chipscholz/
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Call The Damn Leads

"By sales professionals, for sales professionals – Tales of your wildest sales stories and tactics to succeed in your sales career across various industries."

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