A high-level prospect meeting gone terribly wrong

Published: Wed, 04/08/26

Updated: Sun, 04/12/26

April 8, 2026

TOGETHER WITH

Welcome back to The Quota, where April showers (prospecting) bring May flowers (closed-won deals). If you liked that little proverb, you’ll love this week’s issue, where we’ll look at the rise and fall of Yellow Pages sales, share a Sales Fail about a drunk AE, and give some advice to a rep whose shady former coworker is interviewing at his current company. Let’s go!

NUMBER OF THE WEEK

500+

Organic inbound is the best-performing lead source for companies with 500+ employees.

Source: Ebsta

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

ServiceNow is allegedly refusing to pay a salesman commissions on more than $27 million in sales, telling the 13-year veteran of the company that he "overperformed" his quota and insisting that he sign paperwork that retroactively reduces the commission amount, according to a lawsuit filed by the salesperson. ServiceNow has denied these claims. Jorge Costa, who is still employed by ServiceNow as the public sector sales leader in Washington, D.C., is demanding a jury trial and payment of $761,974, double the $380,987 in commissions he says he is owed for closing two massive federal contracts. You can read about it here.
Pipedrive recently conducted a survey of 1,000 Americans that exposes a gap between how people view the sales profession and the reality of modern sales. The findings show that 71% of people agree that sales is a respected profession, yet more than half (53%) admit they have only surface-level knowledge of what salespeople actually do day-to-day. The compensation blind spot is among the report’s most striking findings. Half of respondents believe experienced sales professionals earn less than $70,000 in base salary, which is well below typical market rates for mid-to-senior roles ($85,000-$90,000). And only 16% of Americans believe experienced salespeople earn $100,000 or more in base salary, and just 5% believe top performers can earn $150,000 or more. You can read more about it here.

FEATURE

The Rise (and Fall) of Yellow Pages Sales

For most of the 20th century, if you wanted your phone to ring, you paid to be in the book.

The Yellow Pages started as a simple directory. In 1883, a printer in Wyoming ran out of white paper while producing a telephone directory and used yellow stock instead. The color stuck. By the early 1900s, phone books had split into two sections: white pages for residential listings, and yellow pages for businesses.

What began as a listing quickly became a valuable product. By the 1920s and 30s, local telephone companies—many of them part of the Bell System—realized they were sitting on something valuable. Every business needed visibility, and The Yellow Pages gave them a way to get it.

With the Pages success came a new kind of salesperson: the directory rep. They carried rate cards, mockups, and had a deep understanding of local markets. They walked into small businesses and made a straightforward pitch: when someone needs what you offer, this is where they look.

And for decades, that was true. By the 1950s and 60s, the Yellow Pages had become one of the most powerful advertising platforms in the country. Penetration was near total. Nearly every household had a directory, and when something broke or needed fixing, people flipped to the category and started calling.

By the 1970s and 80s, Yellow Pages sales had become a career. Large directories in major cities generated hundreds of millions in revenue. Top reps earned strong commissions and built long-term relationships with local businesses. Many operated with a high degree of autonomy. If you owned a territory with a dense business base, you could build a very good living.

Companies like AT&T and its regional operating companies controlled much of the inventory. Independent publishers also entered the market, especially after the breakup of the Bell System in 1984, which opened the door to more competition. Still, the core behavior held: when people needed something, they reached for the book.

The sales pitch (correctly) focused on the results. Reps would ask simple questions. How many calls did you get last month? How many jobs did you close? What’s one new customer worth to you? From there, the math followed. A larger ad, a better position, or a second category listing were each framed as a way to capture more of the demand that already existed.

And for many businesses, it worked quite well. For years, entire local economies ran through those pages.

The decline didn’t happen all at once. In the late 1990s, search engines started to change how people found information. Early on, the impact was easy to dismiss. Internet access wasn’t universal, and habits were slow to shift. Yellow Pages companies even launched their own online directories, assuming the brand would carry over. Both systems coexisted, at least for a while.

But the underlying behavior kept moving. By the mid-2000s, more consumers were searching online first. By the early 2010s, smartphones made that shift constant. Instead of flipping to a category and calling down the list, people typed a query and chose from a set of results that changed in real time.

By then, the annual print cycle had become a financial liability and the fixed placement that once created scarcity now felt rigid.

Major publishers saw steep declines. Some consolidated, while others filed for bankruptcy. Dex Media, once one of the largest directory publishers, went through multiple restructurings.

Predictably, the sales role changed with it. Reps who had spent years selling print ads were asked to sell digital packages—search listings, website services, bundled marketing products. Some adapted, but many didn’t. The product was different, the pitch was different, there was more competition, and the certainty that came with the old model was gone.

The Yellow Pages still exists, but is a mere fraction of the search behemoth it once was. But, as every good sales person knows, nothing lasts forever.

You shouldn’t have to choose between Microsoft and Slack. The best sales teams use both.

Most sales teams don't need more tools. They just need their existing tools to actually work together.

That's where Slack comes in.

Slack sits alongside Microsoft 365, connecting your apps, your Salesforce data, and your conversations in one place. So instead of jumping between tools to piece together the full picture of a deal, everything your team needs is right there, in the flow of work, when it matters most. Reps can spend less time hunting for updates and more time actually selling.

Leading organizations have already figured this out.

See how they're using Slack alongside Microsoft 365 to close deals faster, collaborate better, and keep their pipelines moving without ripping out a single tool they already use.

See how it works

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Which famous actor sold tools over the phone before getting his big break?

A. Denzel Washington
B. Robert Downey Jr.
C. Vin Diesel
D. Tobey Maguire

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

I’m a sales engineer. About a year ago, I was supporting one of our AEs on a demo. It was a strong account with multiple stakeholders on the video call, and we had a real chance to close if we handled it well. Needless to say, that’s not how it turned out.

My AE joined the call ten minutes late. And it was immediately obvious that he was drunk. He was talking loudly, leaning in close to the camera, and slurring his words. His face was flushed, and he kept smiling at nothing. He missed basic questions and answered things that hadn’t been asked. I honestly thought he was having a medical episode at first.

Within ten minutes, it got even worse. He interrupted the client mid-sentence, repeated himself, and lost track of where we were in the demo. At one point, he started explaining pricing even though we hadn’t finished the demo. There were long pauses after he spoke. One of the clients glanced off-screen like they didn’t know how to respond.

I started taking over more of the call, trying to keep things moving. Finally, I messaged him: “Hey, I’ve got this part.” No response. Then: “Let me run the rest.” Nothing. Finally: “Can you drop? I’ll take it from here.” He read it and stayed on, still talking. We finished the call, but it was already gone. They never replied to the follow-up. Most awkward sales call I’ve been on in my life.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- April 2026

WORTH A PEEK

Who was the biggest jerk to ever have been your boss? And what was it like working for them? This juicy question was recently posted to Reddit, and the responses did not disappoint. Check out the conversation here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Someone I used to work with is interviewing at my current company. We were at the same company for about a year over four years ago. The problem is that I know this guy is completely unethical.

He would stretch the truth to clients, promise things that didn’t exist yet, and take credit for deals that were clearly team efforts. There were a few situations where he created problems just to swoop in and “fix” them later. Nothing that ever got him fired, but enough that most people started to not trust him.

Now he’s interviewing here. My manager mentioned his name in passing and asked if I knew him since we are connected on LinkedIn. I gave a vague answer and didn’t really say much. I didn’t want to come off like I was badmouthing someone or making it personal. But if he gets hired, there’s a decent chance we’d be on the same team.

I feel like I should say something, but I also don’t want to insert myself into the process or create drama. Not sure what the right move is here.

Conflicted in Location Withheld

Dear Conflicted,

If your manager asked, that’s an opening. Keep it factual and measured. Share what you saw without labeling him or making it personal. Focus on the behaviors, without attacking the person’s character.

It can be something as simple as: “He performed, but there were a few situations where trust became an issue on deals.” This will give your manager a signal without turning it into a takedown. After that, it’s their decision. The only thing you’re responsible for is being honest when asked. Good luck!

Quiz Answer: C. Vin Diesel sold tools over the phone before getting his big break (you can read the source article here)

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Today's email was written by Ken Kupchik and Steve Rado.

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