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

What It Covers

Jeb Blount uses observations of skateboarders practicing tricks at a skate park to illustrate why salespeople fail to implement new techniques. He explains the gap between learning sales strategies and executing them through repeated practice and iteration.

Key Questions Answered

• •The 20-Attempt Rule: Commit to practicing any new sales technique at least 20 times before deciding if it works. Most salespeople try a new approach once or twice, feel awkward, and abandon it before getting past the initial discomfort phase where real results begin to emerge.
• •Iterate Don't Quit Framework: After each failed attempt, track results in writing, identify what went wrong, make one small adjustment to a single variable, and try again. This mirrors how skateboarders watch videos, attempt tricks, analyze failures, and modify their approach rather than simply repeating the same mistake.
• •Success Leaves Clues Principle: When other salespeople successfully use a technique documented in books or training, that proves the method works. Your job is to master their patterns through practice rather than concluding your situation is uniquely different or the approach won't work for you specifically.
• •Discomfort Precedes Mastery: Techniques that feel most awkward initially often produce the best results once mastered. Examples include using silence in negotiations or asking for referrals with specific frameworks. The discomfort is temporary but results become permanent after pushing through the uncomfortable practice phase.