Why confidence backfires with expert buyers

Published: Wed, 03/05/25

Updated: Sun, 03/09/25

March 5, 2025

TOGETHER WITH

Good morning, sales world, and welcome back to The Quota. Or welcome for the first time, or welcome back after you unsubscribed and resubscribed again— er, this is getting awkward. In this week’s issue, we’ll take a look at why confidence backfires with some prospects, share a Sales Fail about an unexpected competition, and give some advice to a rep who doesn’t want to give up WFH. Let’s go.

NUMBER OF THE WEEK

3.1

Buyers change their problem statement an average of 3.1 times during complex purchases

Source: Emblaze

SALES ROUNDUP

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

Tom Brady is taking time off from sport-casting and getting roasted to dip his toe into the exciting world of sales. The seven-time World Champion, sports broadcaster, and entrepreneur, is now adding used car salesman to his growing resume in a new ad for Hertz Car Sales. In the ad, Brady explains the benefits of buying a vehicle from Hertz Car Sales and gives a lucky winner the chance to own a piece of sports history. You can read about the new campaign here.
Car salespeople are improving, according to a recent study by CDK. Over three years, more than 11,000 shoppers have been surveyed about how well their car salesperson has assisted them in key areas. And each year, the numbers have improved. Since 2022, the percentage of people who say a salesperson made efficient use of their time has risen from 75% to 82% in 2024. You can read more about the study here.

FEATURE

The Dunning-Kruger sales paradox: why confidence backfires with expert buyers

The original 1999 study in the Journal of Personality and Social Psychology by Dunning and Kruger demonstrated that low-performing individuals significantly overestimated their abilities, while high-performers underestimated theirs. This cognitive bias became known as the Dunning-Kruger effect. They found this pattern spans across various domains from academic performance to professional skills assessment. This creates an interesting paradox in sales contexts that contradicts conventional wisdom about projecting confidence at all costs.

The Expert Buyer Phenomenon

Now, more than ever, buyers tend to be aware of the problems they’re trying to solve. They’ve done research on the different solutions in the market and often have deep subject matter expertise. When selling to genuine domain experts, traditional high-confidence sales tactics often trigger skepticism rather than trust. Technical buyers can detect superficial knowledge masquerading as expertise, while overstated capabilities create expectation gaps that damage credibility. Expert buyers respond particularly negatively to perceived cognitive shortcuts or simplified explanations of complex concepts they deeply understand.

What makes this phenomenon particularly challenging is that it creates an inverse relationship between seller confidence and buyer receptivity. The more confidently a salesperson presents on technical matters beyond their expertise, the more an expert buyer's internal alarm bells ring. This goes against traditional sales training that emphasizes projecting unwavering confidence and actually sabotages deals with sophisticated buyers.

Practical Applications

Studies in cognitive psychology suggest that acknowledging limitations actually increases credibility with expert audiences. This can help salespeople appear more sincere and self-aware, improving the way they are perceived by buyers. This counterintuitive approach suggests the value of knowledge calibration - using precise technical language and references that genuinely demonstrate domain understanding without overreaching. Developing questions that signal your understanding of nuanced domain problems, but not being afraid to acknowledge your knowledge gaps or product limitations.

The implications extend beyond individual sales interactions to how organizations structure their sales approach to complex products. Sales teams acknowledging the boundaries of their expertise and appropriately incorporating specialized knowledge create more credible customer experiences than those trained to project universal confidence across all product aspects.

Technology giant IBM identified this gap between sellers and expert buyers. To help close it, they implemented the Experts at IBM program, which trained their sales teams to clearly identify when there was a knowledge gap between themselves and their prospective buyers. When a seller realized they were outmatched in domain expertise, they were trained to bring in specific product experts from their Experts team.

This "knowledge-calibrated approach" requires accurately assessing your expertise relative to the buyer and matching confidence levels to genuine knowledge depth. When reaching knowledge boundaries, don’t be afraid to say “I don’t know,” and bring in an expert from your team to help. This will build more credibility and avoid any embarrassing foot-in-mouth moments where you may get caught faking your expertise.

While this approach directly contradicts the "always be confident" sales mantra that dominates conventional sales wisdom, it can be more effective with sophisticated buyers who can detect the difference between genuine expertise and surface-level knowledge. In an increasingly specialized business environment, with niche knowledge at every turn, salespeople who understand the Dunning-Kruger effect can gain a competitive advantage — and avoid losing deals by acting like a know-it-all.

REMOVE THE GUESSWORK FROM YOUR PIPELINE

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

Approximately how many total salespeople do the 500 American companies with the largest salesforces employ?

A. 23 million salespeople
B. 18 million salespeople
C. 14 million salespeople
D. 19 million salespeople

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 had this deal that I felt pretty good about. We had had a few meetings already, and I was hoping to get a verbal confirmation. I walked into the prospect's office and he was there with another guy sitting in the room. I introduced myself. I figured he was another decision maker I hadn't met yet. I was very wrong. It turned out, he was a sales rep for one of our competitors. Once I sat down, the prospect said, "Alright, I'm going to give you each 15 minutes, and after that, I will decide who to go with. Who wants to go first?"

I was completely blindsided. I glanced at the other rep and he seemed equally confused. I panicked and volunteered to go first, which turned out to be a mistake. I went through all the reasons why we were the right fit. I didn't even mention the competitor. I felt like I did a good job under the circumstances. But by going first I gave the other rep the opportunity to refute some of the points I was making and talk about why they were actually a better fit than us. The prospect said he was going with the competitor and asked me to leave. I went back to the office and told my manager about it. He took it pretty well and said, "Maybe we dodged a bullet." Maybe we did, but I missed my quota that month because of it.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- February 2025

WORTH A PEEK

Were you good at sales right from the start, or did it take you a while to get the hang of it? This was a question posed on a recent Reddit thread, and responses ranged from yes to absolutely-freaking-not. You can 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).

Dear Quota Team,

I'm a top-performing sales rep at my company, consistently exceeding my quota for the past two years. Here's my problem: the company just announced a mandatory return-to-office policy. Everyone must be in-office 4 days a week starting next month. I don't want to give up my freedom. Working remotely allows me to hit my goals efficiently and still have time for personal projects, midday workouts, and avoiding a soul-crushing commute. I can get my work done in 3-4 highly focused hours a day, but in the office, I'll need to look busy for 8+ hours.

Should I push harder for an exception based on my performance? Look for a new remote-friendly position? Or just accept that my days of productive flexibility are over? I genuinely enjoy my role and clients, but this feels like a major step backward.

Homebody in California

Dear Homebody,

Your situation is straightforward: you've proven you can excel remotely, and you value the flexibility it provides. You should make your case to your boss using concrete data. Prepare a brief but compelling presentation showing your numbers before and during remote work. Include deals closed, revenue generated, customer satisfaction metrics, and even how your response times improved without a commute.

That said, at the end of the day, the boss makes the rules. If they've made up their mind about in-office work being non-negotiable, you have two choices: comply or find a new job. Good luck!

Quiz Answer: A. The 500 American companies with the largest salesforces employ approximately 23 million salespeople total (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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