3 biggest mistakes I’ve seen after 291 one-on-one sales coaching sessions | Ep 61

3 biggest mistakes I’ve seen after 291 one-on-one sales coaching sessions | Ep 61

Author: Paul M. Caffrey August 16, 2025 Duration: 8:44

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After delivering 291 one-on-one sales coaching sessions in just six months, Paul M. Caffrey has seen the same three mistakes holding salespeople back again and again.

In this episode, Paul breaks down each mistake, why it matters, and the exact steps to fix it — so you can improve your forecasting, increase your close rate, and sell with more confidence.

Whether you’re an Account Executive, a Sales Leader, or preparing for your next SKO, these three fixes will help you move deals faster and close more business.

 

Timestamps

  • 00:00 – Intro: 291 coaching sessions in six months

  • 00:18 – Podcast credits

  • 00:33 – Why you’re losing deals (and it’s not what you think)

  • 01:15 – About Paul M. Caffrey and The Work Before the Work

  • 02:05 – Mistake #1: Skipping Mutual Success Plans

  • 03:20 – How to make Mutual Success Plans a habit

  • 04:02 – Mistake #2: Not Confirming the Agenda

  • 05:05 – How to make agenda confirmation a habit

  • 05:40 – Mistake #3: Avoiding Video Prospecting

  • 06:42 – How to make video prospecting a habit

  • 07:30 – Closing thoughts: Fix one, fix all three


Paul M. Caffrey’s The Prepared Seller moves past surface-level sales tips to explore the foundational habits and strategic thinking that separate consistent performers from the rest. Grounded in Paul’s experience and the principles from his book "The Work Before the Work," each episode focuses on the deliberate preparation that happens long before a pitch is made or a contract is signed. You’ll hear practical discussions on refining your prospecting approach, navigating complex deal cycles, and leveraging technology thoughtfully within a modern sales process. This podcast is designed for ambitious account executives and founders who sell, offering a space for genuine professional development rather than quick fixes. The conversations aim to provide actionable insights you can apply directly to your own pipeline, helping you build a more resilient and effective sales practice. Tune in for a clear-eyed look at the craft of selling, where success is built on the work you do when no one is watching.
Author: Language: English Episodes: 67

The Prepared Seller
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