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This is my favorite book about outbound: Outbounding by William “Skip” Miller.
Why?
It breaks down the difference between inbound deals and outbound deals. And why they should be treated differently.
Plus the Above-the-Line (executives) and Below-the-Line (users) framework for messaging. Which I broke down in this newsletter.
It should be a mandatory read for any GTM leader running outbound.
So if you want to skip reading it, here are my 10 takeaways + 10 core ideas from the book:
P.S. Want the full book? Amazon link (affiliate)
My favorite outbound book: Outbounding by William “Skip” Miller
1-Page Summary
Outbound selling isn’t just “harder inbound.” It’s totally different.
Your prospects need to see they have a problem first. Only then can they think about what to buy.
Inbound leads already know their needs. Outbound prospects often don’t know they have a problem.
That’s why your sales process doesn’t work.
10 Key Takeaways
1 - Why inbound reps struggle with outbound
Inbound reps are trained to handle prospects who’ve already decided to change - they’re essentially order-takers. Outbound requires diagnosing unrecognized problems, creating urgency around the status quo, and guiding prospects through early-stage change psychology.
2 - Inbound vs Outbound = Different Buyer Psychology
Inbound prospects have decided to change: 50%+ want demos immediately.
Outbound prospects don’t know they have a problem: less than 10% are demo-ready. You’re shifting from product-focused selling to change awareness creation.
3 - Change Before Adoption
Outbound success follows Lewin’s model:
Unfreezing (create problem awareness)
Changing (guide evaluation)
Refreezing (solidify solution)
Most reps jump to “buy our product” when prospects are stuck in unfreezing.
Focus on why they need to change their current state, not why they should choose you.
4 - Two Buyers, Two Messages
ATL (executives): Care about ROI, risk, past failures, future threats
BTL (managers/users): Care about features, functionality, present problems
ATLs live in the past and future while BTLs focus on present problems.
Use VAT Framework for ATLs: Value + Action + Time urgency.
5 - “Validate, Don’t Educate” for Execs
Replace “Here’s what we do” with “If you need to reduce costs, here’s what works.” Execs buy confidence in outcomes, not product features.
6 - Solution Box Theory
What prospects think they’re buying (Box A - your product) represents maybe 10% of the real value. The game-changer is Box B - their larger strategic initiative worth millions that your solution enables. ATL buyers have a 30% confidence gap in achieving Box B, and that’s where urgency and big deals live. Stop selling your product; start selling their success in the bigger initiative.
7 - ProActive Sales Matrix prioritizes effort
Plot accounts by value and probability to find your "Red Zone", high-value, winnable deals that deserve maximum effort.
8 - Research is a system, not a task
Systematic homework across company, executive, and industry dimensions transforms generic pitches into relevant conversations.
9 - Track leading indicators religiously
Skills and activity scorecards catch problems 60-90 days before revenue misses, measure what builds success, not just outcomes.
10 - Toward vs. Away drives urgency
Prospects running away from pain buy 2x faster than those moving toward gain, diagnose their motivational direction.
Full Summary + Core ideas
Core Idea #1: Why inbound and outbound are totally different
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