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The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect)

The surprising truth about what closes deals: Insights from 2.5m sales conversations | Matt Dixon (author of The Challenger Sale and The JOLT Effect)


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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

Listen now on Apple, Spotify, and YouTube.

Some takeaways:

  1. The best salespeople are challengers. They don’t think about what’s keeping a customer up at night; they think about what should be keeping a customer up at night. They teach the customer their insights from working with many similar customers, problems, and solutions. While many salespeople are cautious of “overreaching” and are used to “listening to the customer,” when done correctly, most customers prefer honesty and the benefits of leveraging expertise.

  2. Most deals are lost to “no decision” rather than to competition, i.e. it’s not that the customer didn’t buy your software because they wanted to go with someone else’s; it’s that they didn’t buy any at all, despite genuinely exploring the opportunity.

  3. Dialing up the FOMO backfires 87% of the time by actually increasing the odds your customer will be lost to no decision. Contrary to common belief, customers’ fear of messing up (FOMU) outweighs their fear of missing out on benefits (FOMO).

  4. There are three major fears that drive customer indecision:

    1. Fear of making the right choice, which includes concerns about solution configuration, contract terms, and integration

    2. Fear of learning something negative after signing a contract, such as discovering unfavorable reviews or rankings post-purchase

    3. Fear of not realizing the expected ROI, which can lead to reputational damage and even job loss

  5. Use “pings and echoes” to gently surface the customer’s fears and concerns without putting them on the defensive. Just like sonar detects objects underwater, salespeople can use a similar technique to gauge customer preferences and concerns: send out “pings” by articulating potential issues or questions and listen for “echoes,” the customer’s response or confirmation. This opens the door to an honest conversation.

  6. Shift from asking the customer what they want to confidently recommending what they should do. Options are great early on but eventually become overwhelming. Just like a waiter in a fancy restaurant, it’s no help to ask vague questions like “What are you in the mood for?” Instead, take a stance, justify your recommendation, and guide the customer to a decision. They will appreciate your sharing the burden of a potentially bad decision.

  7. When customers are stuck in a place of indecision, apply the JOLT method to jolt them into action:

    1. Judge their level of indecision: Start by assessing your customer’s level of indecision. This involves understanding if they are overwhelmed by choices, still in the research phase, or concerned about the risk involved in the purchase.

    2. Offer a recommendation: Once you have gauged their indecision, offer them a recommendation tailored to their situation. This recommendation should guide them toward making a decision by providing clarity and direction.

    3. Limit the exploration: Encourage your customers to stop endless research and start trusting you as the expert. Help them narrow down their options and focus on what truly matters for their needs.

    4. Take risk off the table: Address any concerns about risk associated with the purchase by (1) proactively resetting expectations, not letting the customer anchor on the most spectacular case studies, and (2) establishing “safety net” options like implementation support, specialized terms, and close collaboration to ensure the customer achieves their goals.

Where to find Matt Dixon:

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

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

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


• 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

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

Lenny may be an investor in the companies discussed.

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Lenny's Podcast: Product | Growth | Career
Interviews with world-class product leaders and growth experts to uncover concrete, actionable, and tactical advice to help you build, launch, and grow your own product.