Outbound Kitchen

Outbound Kitchen

10 outbound secrets from Skip Miller's book

Why inbound reps fail at outbound

Elric Legloire - Outbound Chef's avatar
Elric Legloire - Outbound Chef
Sep 25, 2025
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👋 Welcome to a 🔒 paid edition 🔒 of my weekly newsletter Outbound Kitche. Each week I dive into reader questions about creating outbound systems for sustainable growth. For more: Podcast | Launching Outbound | Scaling Outbound | Deep Dives


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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