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  1. Sales Gravy: Jeb Blount
  2. 16 Sales Horror Stories That Prove You’re Not Alone
16 Sales Horror Stories That Prove You’re Not Alone

16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount · Oct 30, 2025

This Halloween special shares scary sales stories, from disastrous internal errors to cringe-worthy customer encounters, as lessons in resilience.

One Abrupt Rejection Can Demoralize a Junior Rep During Training

When mentoring a new salesperson in the field, the first prospect interaction is critical. A single, blunt dismissal can shatter their confidence and negatively impact their willingness to continue prospecting for the entire day, derailing the training objective.

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16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount·4 months ago

Feeling the Pain of Sales Failures Is a Strong Indicator of Aptitude

The stress and anxiety felt after a sales interaction goes poorly is not a weakness. It signals a high degree of ownership and responsibility—core traits of successful salespeople. Those who feel this pain are more likely to learn, adapt, and ultimately be trusted by clients.

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16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount·4 months ago

Sales Reps Absorb All Blame for Back-Office Operational Failures

When internal teams like operations or IT make critical errors that impact a client, the salesperson must bear the full force of the customer's frustration. Despite being blameless, the rep is the face of the company and is held responsible for managing the crisis.

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16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount·4 months ago

Maintaining Composure During a Virtual Selling Disaster Can Still Save a Deal

Even when a virtual sales presentation descends into chaos with distracting software glitches and a physically collapsing background, a salesperson can still succeed. By maintaining professionalism and focusing on the message, it's possible to overcome the technical failures and secure the next meeting.

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16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount·4 months ago

Highly Confidential Enterprise Deals Can Be Instantly Killed by a Media Leak

For massive, secretive deals like a corporate headquarters relocation, confidentiality is a core requirement. A single leak to the press, against the company's wishes, can violate the terms of secrecy, trigger internal revolt, and cause a multi-million dollar opportunity to collapse immediately.

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16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount·4 months ago

An Internal 'Anti-Champion' Can Covertly Sabotage Deals for Personal Gain

A key stakeholder within a client account may actively create friction and gaslight your team, not for legitimate business reasons, but to steer the contract towards a competitor where a friend works. This form of psychological warfare can derail renewals despite strong performance.

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16 Sales Horror Stories That Prove You’re Not Alone

Sales Gravy: Jeb Blount·4 months ago