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  1. Sales Gravy: Jeb Blount
  2. What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)
What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

Sales Gravy: Jeb Blount · Jan 26, 2026

Master new sales skills like a skateboarder. Embrace the cycle of try, fail, learn, adjust, and repeat to overcome the know-do gap.

The Most Effective New Sales Techniques Often Feel the Most Awkward Initially

Techniques that yield the best results often feel unnatural at first because they challenge your existing habits. Pushing through this initial discomfort is crucial. For instance, strategically using silence in negotiations feels awkward but leads to better deals. The discomfort is temporary, but the improved results are permanent, making the initial struggle a worthwhile investment.

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday) thumbnail

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

Sales Gravy: Jeb Blount·24 days ago

High Performers Iterate After Failure; Most People Just Quit

Many professionals abandon a new technique after a single failed attempt. Top performers, however, engage in a deliberate process: they try, fail, analyze what went wrong, make a small adjustment, and then try again. This iterative cycle of learning and adjusting, rather than simply quitting, is what leads to mastery and separates them from the pack.

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday) thumbnail

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

Sales Gravy: Jeb Blount·24 days ago

When a Proven Technique Fails, Your Execution Is Likely the Problem

It is a common human fallacy to blame the tool or technique when a first attempt fails. More often, the problem lies not with the method but with its execution. Before concluding a strategy 'doesn't work,' you must first re-evaluate your own steps, identify potential errors, and try again. This shift towards personal accountability is essential for genuine skill development.

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday) thumbnail

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

Sales Gravy: Jeb Blount·24 days ago

Commit to 20 Repetitions Before Judging Any New Sales Technique

To truly evaluate a new skill, you must move beyond initial awkwardness and gather sufficient data. A single attempt is not a valid test. Commit to practicing any new technique at least 20 times before deciding if it works. This framework provides enough repetitions to overcome discomfort, begin seeing patterns in results, and make an informed judgment on its effectiveness.

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday) thumbnail

What Skateboarders Can Teach Salespeople About Mastering New Skills (Money Monday)

Sales Gravy: Jeb Blount·24 days ago