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Be Bold and Win the Sale: Get Out of Your Comfort Zone and Boost Your Performance
WHAT’S THE KEY TO SALES SUCCESS?
BOLDNESS.
How to figure out exactly what inhibits you
Why you make certain decisions in moments of discomfort
How to train your brain to prepare for uncomfortable moments
How your customer's own discomforts affect his or her purchase decisions
BOLDNESS.
Includes interviews with Daniel Pink, Larry Winget, Linda Richardson, and many others
The most common challenge every sales professional must overcome is not indecisive customers, inferior products, or innovative competitors. It's the discomfort you feel when initiating calls, dealing with difficult customers, and asking for the sale. Sales expert Jeff Shore argues that boldness is required to embrace this discomfort and leverage it to land the sale. And it is a skill that can be learned. In this inspiring, humor-filled guide, he teaches you:
How to figure out exactly what inhibits you
Why you make certain decisions in moments of discomfort
How to train your brain to prepare for uncomfortable moments
How your customer's own discomforts affect his or her purchase decisions
Featuring self-assessment tools, hands-on exercises, and case studies showing Shore's methods in action, Be Bold and Win the Sale is an indispensable resource for any sales professional.
- GenresBusiness
290 pages, Kindle Edition
First published December 10, 2013
30 people are currently reading
135 people want to read
About the author
Jeff Shore
13 books7 followers[There is more than one Jeff Shore in the GR database. This is Jeff^Shore, author of sales/marketing books.]
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Displaying 1 - 7 of 7 reviews
December 21, 2013
“Be bold and win the sale” by Jeff Shore, could just as easily been called “Be bold and Win!” Jeff introduces a thought process about boldness in sales and in life that directly addresses the one trait that inhibits success – “our addiction to comfort.” Rather than face our discomfort and boldly take action, it is human nature to retreat to a place of comfort, only to regret or justify our decision of inaction later.
Besides finding this book educational and insightful, I found it to be quite inspiring. As I was reading it, making my notes and going through the tasks at the end of the chapters, I found myself addressing the activities that I was putting off in my own state of comfort addiction. And, making great progress along the way.
Many sales books focus on the processes of sales and do very little to address the behavioral components of selling that inhibit or block our successes. “Be bold and win the sale” focuses on the most critical behavioral issues that stop most selling professionals – discomfort. The author successfully maps out the process that is normally followed as a result of our addiction to comfort and provides clear, concise actions that can be boldly chosen to change our behaviors and improve outcomes.
This is a refreshing book. Rather than tout some master plan or revolutionary concept as a “book with fake cures and quick fixes”, Jeff focuses on a real life challenge from an honest, educational, and application oriented perspective. This is as much a book for self-improvement, leadership, parenting and life as it is for selling. This is the bonus value associated with “Be Bold…”
As a resource and coaching tool for today’s sales warriors – it is a can’t miss guide for any selling professional.
Besides finding this book educational and insightful, I found it to be quite inspiring. As I was reading it, making my notes and going through the tasks at the end of the chapters, I found myself addressing the activities that I was putting off in my own state of comfort addiction. And, making great progress along the way.
Many sales books focus on the processes of sales and do very little to address the behavioral components of selling that inhibit or block our successes. “Be bold and win the sale” focuses on the most critical behavioral issues that stop most selling professionals – discomfort. The author successfully maps out the process that is normally followed as a result of our addiction to comfort and provides clear, concise actions that can be boldly chosen to change our behaviors and improve outcomes.
This is a refreshing book. Rather than tout some master plan or revolutionary concept as a “book with fake cures and quick fixes”, Jeff focuses on a real life challenge from an honest, educational, and application oriented perspective. This is as much a book for self-improvement, leadership, parenting and life as it is for selling. This is the bonus value associated with “Be Bold…”
As a resource and coaching tool for today’s sales warriors – it is a can’t miss guide for any selling professional.
Read
May 16, 2025*Be Bold and Win the Sale: Get Out of Your Comfort Zone and Boost Your Performance* is a high-energy, motivational sales guide that challenges sales professionals to abandon timid habits and embrace bold, decisive action to elevate their results. Written by Jeff Shore, the book focuses on developing mental toughness, emotional resilience, and the courage to push beyond internal barriers that limit performance.
The core thesis is simple but powerful: boldness is a skill, not a trait—and it can be developed with intentional practice. Shore argues that what separates top-performing salespeople from the rest is not product knowledge or technique alone, but the willingness to act decisively in uncomfortable or high-stakes moments. Whether it’s asking for the sale, handling objections, or engaging a hesitant prospect, boldness often makes the difference between mediocrity and mastery.
The book begins by dissecting the psychology of hesitation. Shore identifies fear—of rejection, failure, confrontation, or looking foolish—as the main reason salespeople hold back. He explains how comfort zones become performance traps, reinforcing risk-averse behavior that leads to missed opportunities and stalled growth. Using relatable examples and research from behavioral science, he helps readers understand how to override fear-based responses and choose bold action instead.
A recurring theme is emotional discipline. Shore introduces the idea that boldness isn’t recklessness—it’s controlled confidence under pressure. He offers tools for managing internal dialogue, reframing fear as a signal for action, and building mental resilience in the face of discomfort. This shift in mindset is presented as foundational to sustainable sales success.
Practical strategies are provided throughout the book to help readers apply boldness in real-world sales situations. These include:
* **Mastering the moment of hesitation** – recognizing the split-second choice between comfort and courage, and conditioning yourself to choose action.
* **Asking bolder questions** – going beyond safe, scripted conversations to uncover real needs and motivations.
* **Owning the close** – eliminating the fear of rejection by shifting focus from personal validation to helping the customer make a confident decision.
* **Following up with purpose** – pushing past awkwardness to re-engage prospects with confidence and clarity.
* **Leading with value, not apology** – presenting yourself as a trusted advisor, not a desperate seller.
The tone is straightforward, motivational, and often humorous, making the book accessible to both new and experienced salespeople. Shore writes with a coaching style that is both challenging and encouraging, urging readers to take personal responsibility for their growth while assuring them that change is achievable.
Each chapter ends with clear action steps and reflection questions, reinforcing the book’s hands-on, results-oriented approach. Readers are not only taught what boldness looks like, but are guided to practice it consistently until it becomes a natural part of their sales behavior.
In essence, *Be Bold and Win the Sale* is a call to action for anyone tired of playing it safe. It reframes boldness as a competitive advantage—one that can be learned, strengthened, and leveraged for long-term sales success. It’s not about gimmicks or pressure tactics, but about showing up fully, acting with conviction, and creating meaningful value through courageous selling.
The core thesis is simple but powerful: boldness is a skill, not a trait—and it can be developed with intentional practice. Shore argues that what separates top-performing salespeople from the rest is not product knowledge or technique alone, but the willingness to act decisively in uncomfortable or high-stakes moments. Whether it’s asking for the sale, handling objections, or engaging a hesitant prospect, boldness often makes the difference between mediocrity and mastery.
The book begins by dissecting the psychology of hesitation. Shore identifies fear—of rejection, failure, confrontation, or looking foolish—as the main reason salespeople hold back. He explains how comfort zones become performance traps, reinforcing risk-averse behavior that leads to missed opportunities and stalled growth. Using relatable examples and research from behavioral science, he helps readers understand how to override fear-based responses and choose bold action instead.
A recurring theme is emotional discipline. Shore introduces the idea that boldness isn’t recklessness—it’s controlled confidence under pressure. He offers tools for managing internal dialogue, reframing fear as a signal for action, and building mental resilience in the face of discomfort. This shift in mindset is presented as foundational to sustainable sales success.
Practical strategies are provided throughout the book to help readers apply boldness in real-world sales situations. These include:
* **Mastering the moment of hesitation** – recognizing the split-second choice between comfort and courage, and conditioning yourself to choose action.
* **Asking bolder questions** – going beyond safe, scripted conversations to uncover real needs and motivations.
* **Owning the close** – eliminating the fear of rejection by shifting focus from personal validation to helping the customer make a confident decision.
* **Following up with purpose** – pushing past awkwardness to re-engage prospects with confidence and clarity.
* **Leading with value, not apology** – presenting yourself as a trusted advisor, not a desperate seller.
The tone is straightforward, motivational, and often humorous, making the book accessible to both new and experienced salespeople. Shore writes with a coaching style that is both challenging and encouraging, urging readers to take personal responsibility for their growth while assuring them that change is achievable.
Each chapter ends with clear action steps and reflection questions, reinforcing the book’s hands-on, results-oriented approach. Readers are not only taught what boldness looks like, but are guided to practice it consistently until it becomes a natural part of their sales behavior.
In essence, *Be Bold and Win the Sale* is a call to action for anyone tired of playing it safe. It reframes boldness as a competitive advantage—one that can be learned, strengthened, and leveraged for long-term sales success. It’s not about gimmicks or pressure tactics, but about showing up fully, acting with conviction, and creating meaningful value through courageous selling.
March 30, 2018
Very encouraging. Jeff Shore presented at my last two sales conferences and I couldn't have been more motivated after both. This book reflects his strategy and has been helpful in my job!
June 16, 2025
Great book about leaving your comfort zone and challenging yourself
March 26, 2017
Very Clear tips to help you overcome some difficulties you might have!
April 10, 2016
very Insightful. Made me realize that the first thing you have to have in order to closing sales is the gut to ask the closing questions or making asking for appointments. I have been trying to apply this techniques to my daily activity and works very efficiently. I gave 3 stars because the book becomes very redundant at the end.
March 7, 2015
Gets pretty redundant towards the end, but this is among my favorite Jeff Shore books. He is the most contemporary new home sales trainer out there.
Displaying 1 - 7 of 7 reviews