Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss:

• Why 40% to 60% of qualified sales opportunities are lost due to customer indecision

• Why dialing up FOMO doesn’t work, and what to do instead

• The “pings and echoes” technique to catch issues early

• The JOLT method for overcoming indecision

• Key lessons from The Challenger Sale

• Practical examples of how to apply these principles to close more deals

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Brought to you by:

• Enterpret—Transform customer feedback into product growth

• Webflow—The web experience platform

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Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon

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Where to find Matt Dixon:

• LinkedIn: https://www.linkedin.com/in/matthewxdixon

• Website: https://www.jolteffect.com/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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In this episode, we cover:

(00:00) Matt’s background

(01:57) The research behind Matt’s books

(06:08) Insights from The JOLT Effect

(10:15) FOMO vs. FOMU

(18:18) An example of selling software

(26:04) The JOLT method Step 1: Judge their level of indecision

(29:41) The “pings and echoes” technique

(34:49) Step 2: Offer a recommendation

(38:36) Step 3: Limit the exploration

(41:43) Step 4: Take risk off the table

(45:58) When to hit the pause button with a customer

(47:27) Insights from The Challenger Sale

(49:07) An example of a challenger sale

(55:23) Where to find Matt

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Referenced:

• A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting

• The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854

• The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102

• Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition

• Tiger King on Netflix: https://www.netflix.com/title/81115994

• Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral

• Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham

• Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias

• Omission bias: https://thedecisionlab.com/biases/omission-bias

• Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant

• Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect

• Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision

• Dentsply Sirona: https://www.dentsplysirona.com/

• “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE

• Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html

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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

The LIZ and JNY Show - November 10, 2025

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