Gap Selling: Why Price Depends on the Problem You Solve with Keenan

Keenan is the founder and CEO of A Sales Guy, where he helps organizations move beyond product-driven selling and into problem-centric sales strategies. He's also the author of Gap Selling, a framework built around one powerful idea: understanding the gap between where a buyer is today and where they need to be.

In this episode, Keenan and Mark Stiving unpack a truth most teams say they believe—but rarely execute: buyers don't pay for products, they pay based on the size of the problem and the cost of not solving it.

If you've ever wondered why deals stall, why buyers default to "no decision," or why price suddenly becomes the issue—this conversation will challenge how you think about selling, pricing, and what actually drives someone to act.

Why You Have to Check Out Today's Podcast:

• Understand why buyers don't change unless the problem feels urgent enough and how to surface the real cost of inaction.
• Learn how gap selling uncovers the true drivers behind buying decisions by connecting root causes, problems, and impact.
• Discover why pricing power comes from problem size not product features and how that changes the way you sell and price.

"Value is delivered by the size of the problem—and the cost of not solving it."
— Keenan

Topics Covered:

01:07 – What Gap Selling Really Means. How shifting from product pitching to problem diagnosis changes win rates, deal size, and sales outcomes

05:05 – Why Everything Starts with a Problem. The hidden truth: every buying decision is driven by a problem—whether the buyer realizes it or not

09:47 – The Different Levels of Problems in Sales. How surface-level needs hide deeper drivers—and why most salespeople stop too early

10:37 – Root Cause vs. Problem vs. Impact. A powerful framework to uncover what's really driving the need to change

13:56 – What Actually Motivates Buyers to Act. Why root causes don't trigger action—but impact does

19:30 – How Deep Should You Go in Problem Discovery? Knowing when to keep digging—and when you've found what truly matters

20:26 – A Real Example: Breaking Down Root Causes (Obesity Case). How complex problems reveal multiple layers—and why that matters in selling

25:04 – How Trust Is Built Through Problem Clarity. Why buyers trust you more when you understand their problem better than they do

27:33 – Pricing Based on the Cost of Inaction. Why price isn't about your product—it's about how painful it is not to solve the problem

Key Takeaways:

"People don't change unless their current state is untenable." – Keenan

"Gap Selling is a selling methodology that helps salespeople improve their win rate, shorten sales cycles, improve their average contract value and close more deals faster." – Keenan

"Understanding the size of the problem of not solving it is crucial for pricing." – Keenan

People / Resources Mentioned:

• A Sales Guy – Keenan's company; focused on modern sales strategy
• Gap Selling – Framework for understanding buyer problems and driving sales
• Gap Prospecting – Keenan's extension of gap selling into outbound and pipeline generation
• Status Quo Bias – Why buyers avoid change unless impact is high

Connect with Keenan:

• LinkedIn: https://www.linkedin.com/in/jimkeenan/
• Website: https://salesgrowth.com/

Connect with Mark Stiving:

• LinkedIn: https://www.linkedin.com/in/stiving/
• Email: mark@impactpricing.com