Gap Prospecting 2026: Intrigue, Interest, and Outbound That Works With Keenan
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Gap Prospecting that gets replies. Keenan breaks down problem-centric outbound, the Problem Identification Chart, and how to write messages that create intrigue and interest. If you’re stuck in activity theater, this flips the script. Keenan is the CEO of A Sales Growth Company, a Forbes Top 50 Social Seller, and one of the most cited sales experts in the world. He wrote Not Taught and the bestselling Gap Selling, with his new book Gap Prospecting dropping in 2026. His firm was also named a Representative Vendor in the 2025 Gartner® Market Guide for Sales Training Service Providers, Worldwide.
What you’ll learn
- Who Gap Prospecting is for and why now
- Problem-centric selling vs product-centric habits
- The three-layer enablement model: skills, opportunity, forecast
- How to run a great discovery without scripts
- The Problem Identification Chart: problems, impacts, root causes
- Symptoms vs catalysts and how to spot them
- Intrigue→Interest: writing emails buyers answer
- Where AI helps prospecting…and where it makes it worse
- Burn it or build it: rapid takes on quotas, video, texting, gifting, breakup emails
Chapters
00:30 Welcome, guest intro
01:05 Who Gap Prospecting is for
02:39 Why a prospecting book now
04:31 Why coauthoring this time
05:25 The Problem-Centric Operating System
10:36 Where companies blow enablement
12:38 What makes discovery questions good
17:16 The Problem Identification Chart (PIC)
22:22 Has this changed since 2020?
23:22 AI and prospecting: help or harm
31:25 Unexpected lessons: symptoms & catalysts
32:42 Burn it or Build it: 10 hot takes
41:32 One contrarian move for Q1 win rate
42:48 Where to find Gap Prospecting info
43:06 Close
Who this helps
- CROs, VPs Sales, and founders with an outbound motion
- SDRs, BDRs, and AEs who prospect
- RevOps and Enablement leaders building repeatable systems
- Marketers supporting pipeline with outbound signals
Guest
- Keenan, CEO, Sales Growth Company
- Website: salesgrowth.com
- LinkedIn: https://www.linkedin.com/in/jimkeenan/
Host
- Burn The Playbook Podcast — Digital Rebels Consulting
- https://DigitalRebelsConsulting.com
- Marc Crosby — https://linktr.ee/digitalrebelsconsulting
Keywords
gap prospecting, gap selling, problem centric selling, problem identification chart, discovery questions, sales enablement layers, skills layer, opportunity layer, forecasting layer, symptoms and catalysts, intrigue and interest emails, outbound strategy, SDR prospecting, BDR prospecting, AI in sales, breakup emails, video prospecting, multithreading, daily activity quotas, buyer intent
Hashtags
#GapProspecting #GapSelling #Sales #Prospecting #B2B #Outbound #SalesLeadership #BurnThePlaybook #DigitalRebels
gap prospecting; gap selling; keenan; problem centric selling; problem identification chart; PIC; discovery questions; ou
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- Linktree → https://linktr.ee/digitalrebelsconsulting
- Socials → Follow us on LinkedIn www.linkedin.com/in/marcccrosby
- Email → marc@digitalrebelsconsulting.com
- Apple Podcasts → https://podcasts.apple.com/us/podcast/burn-the-playbook/id1828969451
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