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What Top Sales Performers Do Differently

31 chapters. No fluff. No theory. A blunt, practical guide built from 27 years at Oracle, IBM, Demandware, Alteryx, and beyond — for every rep who wants to stop pitching and start closing.

"You've been my boss, my colleague, a trusted partner, my mentor, and most importantly, my friend over the last 16 years. You have a heart of gold and a wealth of knowledge to share."

"This book will be the golden ticket to president's club."

"But now other people are going to get access to all the little nuggets of insight I gathered from you over the years. Ok, fine. Let it rip."

"Every time we chat I learn something — can't wait to have it all written down."

"Anyone who's worked with Darrin knows the impact he has on people professionally and personally."

Preview the Contents

Sell the Hole, Not the Drill — book cover by Darrin De Stasio

About the Book

Nobody wakes up excited to
buy your product.

They wake up thinking about missed targets, wasted time, broken processes, and pressure from every direction. Your product only matters if you can connect it to something they already care about. And most salespeople never make that shift.

Sell the Hole, Not the Drill is not a motivational speech. It is not a list of tactics dressed up as strategy. It is a blunt, practical guide to what actually separates the top five percent from everyone else — built from 27 years of doing it at the highest level.

Whether you are a new rep finding your footing or a seasoned seller who knows something is off but cannot name it — this book will change how you sell.

Every dollar of proceeds is donated to BackPack Buddies — a program of the Food Bank of Central & Eastern North Carolina dedicated to making sure kids have access to nutritious meals outside of school hours.

What You Will Learn

Why buyers decide emotionally and justify logically — and exactly how to use that to your advantage
The questions that actually open deals versus the ones that just fill time and create false progress
How to run discovery calls, demos, and negotiations that move things forward instead of stalling them
The President's Club math — working backwards from your quota to the exact weekly activity targets you need
Why ninety percent of reps quit after the fourth attempt — and what the top performers do after that
How to build trust fast, price with confidence, and stop apologizing for your value
The real reason deals stall — and it is almost never what you think it is

From the Book

Lines that will stick with you.

These are the ideas that change how you think about selling.

Pressure does not create conviction. It creates caution. And cautious buyers do not say yes — they just get better at saying "not yet."

Chapter 21

Trust is built in inches and lost in seconds. One careless moment can undo ten great conversations.

Chapter 26

Practitioners know their buyer before the conversation starts. Amateurs find out during it.

Chapter 30

Inside the Book

31 chapters. Nine parts. No filler.

Part I

Fix Your Broken Sales Brain

01Nobody Is Thinking About You

02Features Are Boring. Outcomes Pay.

03Stop Pitching. Start Helping.

Part II

How Buyers Actually Behave

04If They Do Not Like You, You Are Done

05Never Rely on One Contact

06People Do Not Decide Logically

07Scripts Kill Deals

Part III

Skills That Separate Pros

08Ask Better Questions

09Shut Up and Listen

10Read the Room

11Teach Something or Be Forgotten

Part IV

Make Your Value Impossible to Ignore

12So What?

13Confused People Do Not Buy

14Sound Different or Sound the Same

Parts V & VI

Real Conversations & Closing

15The Discovery Call

16The Demo Trap

17Know Who You Are Selling To

18–25Objections, Negotiation & Closing

Parts VII–IX

Be Someone Worth Buying From

26Trust Is Built in Inches

27–29Credibility, Character & Managing Up

30Show Up Ready or Do Not Show Up

31Getting to President's Club

Every Copy Makes a Difference

Buy the book.
Help a kid thrive.

BackPack Buddies is a program of the Food Bank of Central & Eastern North Carolina. Every week, they make sure children have nutritious food when school closes — so hunger does not steal their focus or their chance to thrive. Every dollar of proceeds from this book goes directly to that mission.

Learn about BackPack Buddies

100%

of proceeds from this book donated to BackPack Buddies

From the Readers

Successful selling is very hard work. With a fantastic product or service, use this book to understand the steps to a successful sale that you must develop. It outlines all best practices, in detail, so that you create the opportunity to bring the solution to your prospect that drives value, solves the problem and enables the customer to move on to solving their next problem with you.

Co-Founder

Alteryx

What Top Sales Performers Do Differently

Nobody wakes up excited to
buy your product.

The mission behind the book — and what to expect.

Lines that will stick with you.

31 chapters. Nine parts. No filler.

Buy the book.
Help a kid thrive.

Ready to change how you sell?

What Top Sales Performers Do Differently

Nobody wakes up excited tobuy your product.

The mission behind the book — and what to expect.

Lines that will stick with you.

31 chapters. Nine parts. No filler.

Buy the book.Help a kid thrive.

Ready to change how you sell?

Nobody wakes up excited to
buy your product.

Buy the book.
Help a kid thrive.