Why most sales training doesn't work

Published: Wed, 10/22/25

Updated: Fri, 10/24/25

October 22, 2025

TOGETHER WITH

Good morning, and welcome back! While you were busy helping your kid pick out their Halloween costume, we were picking out similarly overpriced sales content for you to enjoy. In this week’s issue, we’ll look at why most sales training doesn’t work. Then, we’ll share a Sales Fail about sneezing, along with our usual grab-bag of fun. Enjoy!

NUMBER OF THE WEEK

82% of top performing salespeople say they always perform research before contacting prospects, compared to 49% for other sellers

Source: LinkedIn

SALES ROUNDUP

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

A Winnipeg building supply salesman has been charged with embezzling more than $4 million through fake applications submitted to his employer's rebate program over a span of eight years. Between April 2016 and April 2024, the former employee registered four fictitious home building companies, including fake employees. He collected about $4.2 million in rebates after submitting an estimated 5,500 fraudulent applications to the supplier's program, police say. You can read more about it here.
Salesforce CEO Marc Benioff says AI won't replace sales, and that Salesforce is still hiring thousands of salespeople. Benioff said that "face-to-face communication" was still needed in sales. "AI doesn't have a soul. It's not human connectivity," Benioff said this week. He also said he is hiring thousands more salespeople and aims to reach 20,000 account executives. You can read more about it here.

FEATURE

Why (most) sales training doesn't work

Walk into any sales organization and you'll find a predictable ritual playing out: quarterly training sessions where reps watch video modules, flip through workbooks, and nod along to presentations about proven methodologies. Companies spend billions on sales training each year, yet ask any salesperson how they feel about it, and you'll likely get an eye roll.

The numbers tell a stark story. Despite the massive investment in sales training, studies show that 87% of new skills are lost within a month of training. So why does an industry that prides itself on results continue to pour money into something that demonstrably doesn't work?

The answer lies in three fundamental problems that plague modern sales training, according to industry experts who've seen the failures firsthand.

We're Teaching Yesterday's Tactics for Tomorrow's Buyers

Sam McKenna, founder of #SamSales, a sales trainer who's worked with hundreds of organizations, points to a critical flaw in how the industry approaches skill development. "The primary risk in sales training is that we still rely on methodologies built decades ago," she explains. "Sandler? 1967. SPIN? 1988. MEDDIC? 1990s."

The issue goes deeper than just age. These legacy frameworks were designed for a different era of selling, when buyers had less information and salespeople held more power in the relationship. Today's buyers research extensively before ever talking to a salesperson, often knowing more about a product than the rep trying to sell it.

"The age of methodologies alone isn't the issue," McKenna clarifies. "It's that it walks you through a massive overhaul in your process, and tells you what to do, but not how to do it." Consider the standard advice that pervades sales training: multithread your deals, find the economic buyer, identify buyer pain. All critical concepts, but the execution details are either non-existent, outdated, or rely on frameworks that feel awkward in modern buying situations.

The One-and-Done Problem

Ian Koniak, a former number-one account executive at Salesforce turned sales trainer, identifies another core issue: most sales training treats learning like a light switch that can be flipped on during a workshop and then left on to illuminate future performance.

"The main reason is that sales training is typically set up in a 'one and done' format with little to no follow up and reinforcement afterwards by sales leadership, so the information doesn't stick," Koniak explains. "Essentially, when the training is over people go back to what they were doing beforehand."

This creates a cycle where organizations invest heavily in bringing in expert trainers, gathering their teams for intensive sessions, then wonder why performance metrics remain unchanged months later. Koniak puts it bluntly: "Most sales training fails because a one or two day training can spark inspiration but it can't rewire habits and behaviors. Real transformation takes time, accountability, and daily reinforcement."

The problem isn't the quality of the material being taught. Methodologies like Challenger or SPIN contain valuable lessons about buyer psychology and the sales process. The breakdown happens in the gap between learning and application, where new concepts get overwhelmed by ingrained habits and the pressure to hit monthly quotas.

Vague Strategies Without Tactical Execution

Perhaps the most frustrating aspect of traditional sales training is its tendency toward inspirational platitudes rather than practical instruction. McKenna points to this as a major stumbling block: "Many sales trainings also lack practical and actionable advice. What works is less of 'you need to be strategic in how you sell and you need to meet your buyer where they are!' but more of 'Three ways you can be more strategic are... and say exactly this in those instances.'"

This vagueness leaves salespeople feeling motivated but unprepared. They understand they should be more strategic or consultative, but lack the specific language, questions, and frameworks to execute these concepts during actual sales conversations.

A Path Forward

The solution isn't to abandon sales training entirely, but to fundamentally reshape how it's delivered and reinforced. McKenna advocates for a more focused approach: "In order for trainings to be effective today, we need to arm our sellers with modern content that is immediately actionable, and that offers one or two big quick changes they can make to see progress, build trust, and come back to learn the rest."

#SamSales Perfect Discovery Call training exemplifies this philosophy. Rather than overwhelming reps with dozens of concepts, it focuses intensively on changing one element: the opening script. "That one shift changes the entire trajectory of the call, which builds enthusiasm in the rep and builds the muscle to adopt the new methodology."

Koniak emphasizes the need for ongoing reinforcement: "The reason sales training often misses the mark isn't the material—it's that it never transforms what reps actually do in the field."

The persistence of ineffective sales training speaks to a deeper challenge in sales organizations. Leaders know their teams need development, but the current approach treats complex behavioral change like a software update that can be downloaded and installed in a day. Until the industry acknowledges that real skill development requires sustained effort, practical application, and modern methodologies, sales training will continue to be an expensive exercise in good intentions.

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Where was sales trainer Jeff Gitomer’s 17,000 square foot condo located?

A. Phoenix, AZ
B. Boca Raton, FL
C. Charleston, SC
D. Charlotte, NC

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 woke up the morning of a big signing for a first-time homebuyer who had been waiting weeks to close. I wasn't feeling great, my seasonal allergies were acting up, but I tried to power through. After they arrived at the house, we sat down at the kitchen table, and I started walking them through the documents. Everything was going smoothly until they had a question about the disclosure section.

I leaned in close, pointing at the specific paragraph they needed to initial. Right as they started writing their name, I felt it coming. I didn't even have time to turn my head or get my hand up. I just exploded. A full, wet, uncontrollable sneeze directly onto the contract. And their hand, the pen still touching the paper.

They looked up at me slowly, their expression somewhere between disgust and disbelief. Their hand didn't move. The pen didn't move. We just stared at each other for what felt like an eternity.

I started apologizing profusely. They carefully set down their wet pen, grabbed a tissue from the box on the table, and wiped their hand without saying a word.

The signing continued in painful silence. They signed everything, we shook hands (after I thoroughly sanitized mine), and the deal closed. But I've never felt more mortified in my entire career.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- October 2025

WORTH A PEEK

If you were 36 and looking to break into sales, what would be the best path forward? A frustrated bartender recently posted this question to Reddit, with valuable responses for all walks of life. You can read 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).

Dear Quota Team,

I sell HR software and joined my company about six months ago. Since then, one of the senior reps has unofficially taken me under his wing. At first, I appreciated it — he offered tips, introduced me to a few prospects, and checked in after my first demos. But lately, it’s starting to feel less like mentorship and more like babysitting.

He constantly drops into my DMs with “advice” I didn’t ask for, volunteers to “sit in” on my calls, and tells people on the team he’s “helping me find my voice.” My manager thinks it’s great that I’m getting coached, but I’m starting to feel smothered and patronized.

How do I set boundaries without making it awkward or looking ungrateful?

Micromanaged in Location Withheld

Dear Micromanaged,

You don’t need confrontation here — just a reset. Acknowledge his good intentions so the tone stays friendly, then start creating more distance in how you work. Keep conversations focused on your own progress rather than his input, and disengage politely when he oversteps. If the pattern continues, mention to your manager that you’re trying to take greater ownership of your process. The goal is to reestablish independence without causing friction, and to remind everyone — yourself included — that mentorship only works when it’s mutual, not one-sided. Good luck!

Quiz Answer: D. Sales trainer Jeff Gitomer’s 17,000 square foot condo was located in Charlotte, NC (You can read the source article here).

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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