The Real Reason Reps Miss Quota | Bite Sized Tactics

The Real Reason Reps Miss Quota | Bite Sized Tactics

Struggling to diagnose why your sales rep isn’t converting? Jordan Chavez (Head of Enterprise GTM @ ActivelyAI) breaks down his “5 Whys” sales coaching framework—a simple, proven method to uncover the real reason behind poor performance. Instead of jumping to surface-level fixes (like “just sell the value”), we’ll show you how to ask layered “why” questions that reveal what’s actually holding your reps back—whether it’s low confidence, weak discovery, or lack of preparation. Whether you're a sales manager, team lead, or AE looking to self-diagnose, this framework will help you stop treating symptoms—and start solving the real problem. RESOURCES DISCUSSED: ⁠Join our weekly newsletter⁠ ⁠Things you can steal⁠ ⁠Save $50 on any 30MPC course⁠ with code “PODCAST” ⁠How to Run 1-on-1s⁠ ⁠Free Sales Templates, Scripts and Guides

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#86 - Embracing competitors and asking the right questions at the right time (Ryan Staley, Founder & CEO @ Whale Boss)

#86 - Embracing competitors and asking the right questions at the right time (Ryan Staley, Founder & CEO @ Whale Boss)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Learn from the 5 biggest deals you have lost and replace them with the 5 fastest deals yo...

15 Dec 202130min

#85 - Death of the helpful seller: Use proven psychology to stop losing deals (Belal Batrawy, DeathtoFluff)

#85 - Death of the helpful seller: Use proven psychology to stop losing deals (Belal Batrawy, DeathtoFluff)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Disclose “often withheld” information around pricing, competition, weakness, and implemen...

8 Dec 202133min

#84 - Leading with data in your sales process and why traditional sales is broken (Anthony Iannarino, President @ SOLUTIONS Staffing)

#84 - Leading with data in your sales process and why traditional sales is broken (Anthony Iannarino, President @ SOLUTIONS Staffing)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Lead with insights to show the prospect that you know their business. * Don’t assume the ...

1 Dec 202132min

#83 - Selling to executives, selling with them, and everything in between (Kris Rudeegraap, CEO @ Sendoso)

#83 - Selling to executives, selling with them, and everything in between (Kris Rudeegraap, CEO @ Sendoso)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Bring your executives early to accelerate the deal instead of at the end when it’s too la...

24 Nov 202128min

#82 - Getting out of the script for more effective Gap Selling (Keenan, Author of Gap Selling)

#82 - Getting out of the script for more effective Gap Selling (Keenan, Author of Gap Selling)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Don’t talk about root causes/technicalities until you get to the business impact first. *...

17 Nov 202132min

#81 - Mapping out your demo during the discovery call to drive the ‘aha’ moment (Will Lui, CRO @ Pairsoft)

#81 - Mapping out your demo during the discovery call to drive the ‘aha’ moment (Will Lui, CRO @ Pairsoft)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Tie each feature you demo to the discovery, then an example, then a use case so it really...

10 Nov 202127min

#80 - Working with your Sales Engineer to run effective discovery and demos (Zach Farber, AE @ Salesforce)

#80 - Working with your Sales Engineer to run effective discovery and demos (Zach Farber, AE @ Salesforce)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Lean on your champion to schedule large meetings with multiple functional groups. * Stay ...

3 Nov 202128min

#79 - Systematizing the way you use text messages in a deal cycle (Eric Buckley, President @ Skipio)

#79 - Systematizing the way you use text messages in a deal cycle (Eric Buckley, President @ Skipio)

Join the most tactical sales newsletter in the world: https://hubs.ly/Q01-R33G0 Four Actionable Takeaways:  * Don’t try to sell over text, your goal is to get a response, meeting, or call. * Keep you...

27 Okt 202126min

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