EPISODE · Aug 16, 2025 · 8 MIN
3 biggest mistakes I’ve seen after 291 one-on-one sales coaching sessions | Ep 61
from The Prepared Seller · host Paul M. Caffrey
Assess Yourself or your sales team vs Top Performers Here for FREE! or Free Sales Preparation Course to help you outperform the competition in 19 minutes. 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
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3 biggest mistakes I’ve seen after 291 one-on-one sales coaching sessions | Ep 61
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