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Wes Schaeffer, Sales Outreach, Sales Whisper

TSE 1124: Sales From The Street: “The Fundamentals of Sales Outreach”

Wes Schaeffer, Sales Outreach, Sales WhisperMany sellers have a tough time with outbound sales, so we’re spending the month of June focused on the topic, and today we’re specifically addressing the fundamentals of sales outreach.

Wes Schaeffer entered sales in 1997, covering stocks, bonds, retail, real estate, and high tech. He decided that, since sales was crazy and uncertain, he’d bet on himself. He laid the foundation for The Sales Whisperer, where he helps people with sales training.

Outbound struggles

Too many sellers mistakenly believe that outbound is dead. That cold calling and email are dead. The truth is you simply have to do a little bit of homework.

Some people would say that because everybody drinks water, if you sell water, everyone is your prospect. But some people are content drinking water out of a hose. Not everyone will spend money on your stuff.

Client selection is important. You have to figure out who’s going to buy your stuff and who isn’t.

The number of people who are ready, willing, and able to buy what you sell right now is in the single digits. If, for example, you just bought four brand new tires for your car, it doesn’t matter that you’re having a 50-percent-off sale.

Follow a script

Now that you know who you’re going after, what will you say? Will you fall into the trap of not following a script because it feels unnatural?

The Rock has made over $60 million a year by regurgitating scripts. He makes it his own and he makes it believable. The truth for all of us is that we’re living on a script.

I once talked in a presentation about seeing the band Chicago and about the fact that they play the same 20 songs in the same order at every single show. What would happen if they decided to just wing it every now and then?

That’s not what professionals do. Professionals practice things until they can’t get them wrong. You could wake them out of a stupor, hand them a guitar or keyboard, and they could play any song perfectly.

Practicing skills

Look at Tom Brady or Lebron James or Tiger Woods. I guarantee you they are still practicing. Are you willing to practice the little bitty things? How do you open? What do you say? How do you title your emails? How do you build interest?

If you sound like everybody else, I’m going to treat you like everybody else. The only way I can differentiate between you and everyone else that sounds like you is on price.

Think of the phone calls you get from an autodialer. They’re nice because they streamline things, but when people hear the long pause while it’s connecting to the first available person, they are completely uninterested. Then they mispronounce your name and you’re done.

Diagnose the problem

Wes recommends at least five emails in any outbound process. He also pointed out the distinction between frequently-asked questions and “should ask” questions. FAQs can be written out and sent in an email. The “should ask” questions allow you to differentiate yourself. These are the things the prospect doesn’t know.  

Understand your product and the situation of your prospects well enough to know what issues might arise. Our goal in prospecting is to ask a question that our prospect can’t answer.

Doctors do the same, and it’s why we trust them. When they take the time to diagnose the problem, we trust their prescription.

Ask questions

  • How are you generating leads?
  • What trends are you seeing?
  • Is it becoming more expensive to run ads?
  • How is your team performing?
  • Do you experience ups and downs?

Spend some time on your “should ask” questions.

We’re all too close to our own offerings. There’s an adage that says you can’t read the label from inside the bottle.

Outreaching sequences

Timing matters in outreach, and that’s why you need multimedia multi-step followup sequences. You need a success story about a prospect in your niche. You need a case study or a video testimonial. And then you’re off and running.

Dripping a prospect is a little like dating. When you continue coming back to your prospects, they eventually decide that there must be something good about your offering.

You have your target market or your dream 100. It’s worth persisting because, eventually, something is going to happen: a machine will break or the competition will miss a delivery. Maybe an employee will quit or they will have their own quality issues.

Start early, stay late

Remember that whatever you can measure you can improve.

Jeffrey Gitomer speaks about gold calling because he says there isn’t such thing as pure cold calling in B2B. You’re most likely to reach people by phone. You can do direct mail and other things, and they may work.

Executives and decision-makers get to the office early and they stay late. Since I’m a west coast guy, I start calling the east coast about 2 p.m. when the assistants and receptionists have gone home. Same with the lunch hour. The hourly people take their breaks while the boss keeps working.

Be strategic about your calls. Use LinkedIn to find information about your prospects. Where did they go to school? Do they have a recent article? The research demonstrates that you did your homework. It differentiates you from your competition.

Little things add up. Trust the process and have a process.

“The Fundamentals of Sales Outreach” episode resources

Connect with Wes at You can find his social media links and his phone number there.

Connect with me at

Try the first module of the TSE Certified Sales Training Program for free.

This episode is brought to you by the TSE Certified Sales Training Program. I developed this training course because I struggled early on as a seller. Once I had the chance to go through my own training, I noticed a hockey-stick improvement in my performance.

TSE Certified Sales Training Program can help you out of your slump. If you gave a lot of great presentations and did a lot of hard work, only to watch your prospects choose to work with your competitors, we can help you fix that. 

Tools for sellers

This episode is also brought to you in part by, a Chrome browser extension for Gmail that allows you to track and schedule your emails. It’s super easy, it’s helpful, and I recommend that you try it out. You’ll receive real-time alerts anyone opens an email or clicks a link. allows you to see around the corners. You can see when people open your email, or when they click on the link you sent. will give you half-off your subscription for life when you use the Promo Code: Donald at check out.

I hope you enjoyed the show today as much as I did. If so, please consider leaving us a rating on Apple Podcast, Google Podcast, Stitcher, or wherever you consume this content and share it with someone else who might benefit from our message. It helps others find our message and improves our visibility.

If you haven’t already done so, subscribe to the podcast so you won’t miss a single episode. Share it with your friends who would benefit from learning more.

Audio provided by Free SFX and Bensound.


Donald Kelly, Stephen A Hart, The Sales Evangelist

TSE 1000: The Sales Evangelist 1000th Episode with Donald C. Kelly

Donald Kelly, Stephen A Hart, The Sales Evangelist

It’s The Sales Evangelist 1000th episode and Stephen A. Hart from the Trailblazers.FM Podcast is conducting the interview while Donald Kelly answers the questions.

This podcast started five years ago after Donald attended sales training to try to improve his performance. He started seeing some gains, and he figured the very least he could do was tell other people what was working for him.

He realized along the way that he would get to interview great guests like Jeffrey Gitomer who would share a wealth of information and he was hooked. Donald wanted to share sales content that would help himself and others at the same time.

Blessings and opportunities

The greatest benefit to a podcast like this is the relationships you build. There’s a camaraderie and people want to help each other. [05:50]

Perhaps it’s because the medium is so new, but a lot of podcasters are connecting with each other to share experiences.

People have become like family, and many business opportunities have emerged from it.

There’s a whole crew of people in the background who help create the content, and it’s blessing people along the way.

After Donald jumped ship from his full-time job in 2015, this lifestyle business allowed him to travel and speak in different parts of the country, and it all stemmed from the training and consulting that has developed.

10,000 hours

The podcast is officially five years old, which amounts to about 10,000 work hours. According to Malcolm Gladwell’s theory that it takes 10,000 hours to become an expert, Donald is officially an expert podcaster now.

The story started when Donald was working at a software company in Boca. His plan was that at the three-year mark, he wanted to go back to grad school for an MBA. [10:11]

The other alternative was that he would launch a startup.

TSE started as a hobby because Donald had done B2C in high school and college. Now, he transitioned to B2B, but he didn’t know how to talk to people or set up business opportunities.

His company provided training and he discovered a love of teaching and an excitement about the content he had learned.

He paired his love of teaching and his desire to be the center of attention, and it was a perfect marriage. Edutainment allowed him to educate and entertain at the same time.

Birth of a podcast

Jared Easley introduced Donald to the world of podcasting despite the fact that Donald knew nothing about it.

He started by listening to Seth Godin’s Startup School, a podcast that featured Seth guiding 30 entrepreneurs through the process of launching a dream business. [11:46]

He was still debating startup or college, and he realized that a startup didn’t have to mean developing a product. Donald didn’t see how the podcast was going to make money, but he launched it as a hobby.

The platform existed six months before the podcast did, but Donald recalls that he had to get over the worry and just pull the trigger. He had to stop worrying about how it would sound and what people would say about it.

He eventually decided that he had something valuable and he needed to share it. When he got out of his own way, the money started coming in.

When Donald started producing content that benefited the people around him, people started to raise their hands and seek his help.

Lessons learned

Donald calls episode 1 cringe-worthy. He says he was nervous and afraid throughout it. He was self-conscious about his voice, and he didn’t own his personality. [15:29]

Donald also wishes he had done video much sooner. He was afraid of the comments people would make and that fear kept him from producing video.

Donald also wishes he had known that people don’t know what you have to offer until they know what you have to offer. He was afraid of sounding pushy, so he was apprehensive about sharing what he knew.

Take more action. Get out of your comfort zone. Get out of your own way.

Despite the late start to the video world, TSE is getting into video now, so it’s better late than never.


Donald points to the burned-ship theory that dates to sailors who were either going to burn the ships and win the battle or die on the seashore. There was no escape.

If you’ve burned the ship, there’s no alternative, so you have to make it work. Those men are the master of their own destiny.

Although Donald could still be employable in the sales realm if necessary, he doesn’t want to use that as a parachute. [19:27]

The “no’s” can’t hinder him. He either has to conquer or die.

He realizes that the “no’s” aren’t personally directed at him.

Your “why”

Donald’s desire to provide for his family drives his passion and his motivation. He wants to make things happen so that his family never has to be in the predicament of being homeless again. [21:50]

Those dark moments such as the first lull in listenership can plague podcasters.

Although numbers are great for measuring, Donald got too focused on the numbers. He started to compare too much and he neglected his own community.

When the website was down for a prolonged period in 2016, he started to feel tremendous stress. For 1-2 months there was no new content.

He worried about losing listeners and the huge setback that might come. He wasn’t sure he would be able to continue because there were so many technical problems.


You can’t succeed in a silo. Name any company and you can almost guarantee that they had help from some outside forces. [29:17]

The term entrepreneur is deceptive because there’s really no single person who creates a business. Donald avoided asking for help because he was embarrassed and he thought he was supposed to know how to solve the problem.

Advice and discussion help people share their burdens and to recognize that they can benefit from other people’s input.

Top takeaways

People who succeed do so because they partnered with others for good. There are people who are willing to partner strategically to make things work. [31:57]

All of his guests who have had success did so because they found synergy in the people they worked with.

Look at Henry Ford and the number of companies that spawned from his invention. Tire companies, radio companies, and other companies developed because of it.

You can’t be a lone wolf and you must be willing to admit that other people might be able to do things better than you can.

TSE is writing for HubSpot now and has been mentioned in Entrepreneur and Inc. Magazine because Donald was willing to reach out.

Don’t be afraid to sell yourself. People in post-recording conversations advised Donald that he was charging too little.

Customers aren’t paying for one hour of guidance or coaching. They are paying for 15 years of experience. [35:23]

Be aware of your worth. If you undervalue yourself, no one will willingly pay you more. Ask for more than you’re comfortable asking for.

Always push yourself for bigger and better things.

Once you push outside of your comfort zone, you’ll evolve. You’ll find yourself doing things that once scared you.

Emotional rollercoaster

Preparation helps us avoid the emotional rollercoaster of sales. October Donald should be helping December Donald. Salespeople must plan much further out than they can comfortably do. [38:50]

If you know you need 5 deals, you should put 7 or 8 in your pipeline. Never ease up off the gas. Have a systematic approach.

When Donald coaches people, he helps them see beyond the now. He helps them develop a system that prevents lulls.

Healthy competition

Donald remembers wanting to be included on a list of top sales podcasts. [44:01]

He refers to the power of “coopertition,” where people become allies.

As a track athlete, he learned that when you’re turning back to see where other people are, you aren’t aerodynamic anymore. You lose your focus and you slow down.

Instead of looking to see where other people are, look toward the finish line. Compete against your own yesterday instead of competing against others.

Future of TSE

The Sales Podcast Network will continue to grow and offer a community of salespeople who will encourage one another. [50:57]

If TSE ever gets boring, maybe the day would come when it would be “sunset.”

TSE will continue to grow. The goal on sponsorship side will eventually separate so that the training organization will separate from the media company side.

TSE will seek to double its revenue, and ultimately the platform will be bigger than just a podcast.

TSE has been a huge influence in the podcasting space by encouraging those people who are in the community.

The Sales Evangelist 1000th Episode resources

Connect with Stephen A. Hart and check out his  Trailblazer.FM Podcast.

This episode is brought to you in part by, a powerful sales automation platform that allows you to build highly personalized, cold email campaigns. To learn more, go to It will help you with your outbound to expand your outreach. It allows you to set it and forget it. Your prospecting will never ever be the same.

Previously known as TSE Hustler’s League, our TSE Certified Sales Program offers modules that you can engage on your own schedule as well as opportunities to engage with other sellers in other industries.

This episode is brought to you in part by, a Chrome browser extension for Gmail that allows you to track and schedule your emails. It’s super easy, it’s helpful, and I recommend that you try it out.

You’ll receive real-time alerts anyone opens an email or clicks a link.

I hope you enjoyed the show today as much as I did. If so, please consider leaving us a rating on Apple Podcast, Google Podcast, Stitcher, or wherever you consume this content and share it with someone else who might benefit from our message. It helps others find our message and improves our visibility.

If you haven’t already done so, subscribe to the podcast so you won’t miss a single episode, and share with your friends!

Audio provided by Free SFX and Bensound.


Jeffrey Gitomer, Napoleon Hill, Positive Thinking, Truthful Living: The First Writings of Napoleon Hill

TSE 966: The Law of Harmonious Attraction

Jeffrey Gitomer, Napoleon Hill, Positive Thinking, Truthful Living: The First Writings of Napoleon HillIn this episode of The Sales Evangelist, I had the pleasure of speaking once again with Jeffrey Gitomer, The King of Sales, about the Law of Harmonious Attraction.

Jeffrey is an author, speaker, and business trainer who writes and lectures internationally on sales, customer loyalty and personal development.  He also hosts the very popular Sell or Die podcast.

Jeffrey talked with us about his newest book, Truthful Living: the First Writings of Napoleon Hill. The first chapter, Success is Up to You, is now available as a free download for listeners of this podcast.

Napoleon Hill

Napoleon Hill was an American self-help author perhaps best known for Think and Grow Rich, one of the top 10 best-selling books of all time.

Jeffrey has a 15-year relationship of volunteering with The Napoleon Hill Foundation. As a result, when the foundation found the first writings of Napoleon Hill from 1917, they offered them to Jeffrey to edit and annotate as he desired.

Hill, as Jeffrey learned, believed that for someone to sell well, they have to learn more than selling skills; they need to learn how to be a positive person.

This book is not a life-changing book. This book is a life-altering book!

Jeffrey removed the lessons about sales but kept Hill’s personal development lessons.

He included his own observations at the beginning of each chapter and explained how to implement the lessons at the end of each chapter.

But Napoleon Hill’s 100-year-old writings remain completely intact.

If you already subscribe to the lessons in Think and Grow Rich, then Jeffrey’s book will reinforce every single thing that you already believe and already do. It will reunite you with great facts, and introduce you to new ideas.

This book will either put you on a bigger path, a better path, or it will reinforce the path you are already on.  Once you know you are on the right road, the incentive to continue stays with you.

Success is up to You. Finish what you start.

If you can get just those two things into your head, you will completely understand Hill’s writings on personal development and positive attitude.  

The Law of Harmonious Attraction

Don’t confuse this with anything you’ve read before about the Law of Attraction where you simply visualize what you want in order to make it happen.

The Law of Harmonious Attraction instead tells us that big pay and little responsibility seldom occur together.

Hill believed that it’s much easier to create a connection or friendship between like-minded people. It’s easier to build trust when people think alike, converse alike and are comfortable with each other’s strategies, philosophies, actions, and ethics. 

Hill, for example, wanted to attract people with wealth.  To that end, he urged others to read and reread The Law of Financial Success

If you are a diehard listener of Jeffrey’sSell or Die podcast, to offer a more current example, then you and he are already attracted to one another. You know his philosophy, his expressions, and you already feel good about doing business with him.

The salesperson can make things happen by building such relationships and keeping them.

Rapport vs Attraction vs Reciprocity

Building rapport is a lighter version of harmonious attraction. It begins when people ask superficial questions in hopes of finding opportunities to go further. It brings genuine value both people rather than being manipulative.

The idea of reciprocity is that if you help 10 people, then eventually, at least nine of them will help you.

Hill believed we should give without the expectation that people will give back, and with the realization that some will not.

The Five-Point Rule

Hill, in 1917, said this:

Success may be had by those who are willing to pay the price.

Most of those who crave a $10,000/year position*, especially if they are engaged in business, may realize it if they are willing to pay the price.

That price is eternal vigilance in the development of self-confidence, enthusiasm, working with the chief aim, performing more service than you are paid for and concentration. With those qualities well-developed, you will be more likely to succeed.

*approximately $250,000 in today’s dollars

“Harmonious Attraction” episode resources

Grab a copy of Napoleon Hill’s books The Master Key to Riches as well as The Magic Ladder of Success.

This episode is brought to you in part by, a powerful sales automation platform that allows you to build highly personalized, cold email campaigns. To learn more, go to It will help you with your outbound to expand your outreach and it allows you to set it and forget it. Your prospecting will never ever be the same.

We’ll use in the upcoming semester of TSE Hustler’s League to focus on prospecting. We’ll give you insights and tools that will help you gain new customers. In addition, we’ll provide training and strategies that you can implement today to ensure constant flow in your pipeline.

Check out our new semester of The Sales Evangelist Hustler’s League. We’re taking applications for the semester beginning in January, and we can only take a limited number of people.

This episode is also brought to you in part by Maximizer CRM, personalized CRM that gives you the confidence to improve your business and increase profits. To get a demonstration of maximizer, go to the sales

Click on the link to get a free demo of what Maximizer CRM can do for you. It integrates your marketing campaign as well as your CRM, and it works whether you’re a small organization or a large one.

Leave us a review on Apple Podcast, Google Podcast, Stitcher, or wherever you consume this content, and share it with someone else who might benefit from our message. It helps others find our message and improves our visibility.

If you haven’t already done so, subscribe to the podcast so you won’t miss a single episode.

Audio provided by Free SFX and Bensound.

Donald Kelly, The Sales Evangelist Podcast, 800th Episode

TSE 800: Some of The Best Tips From Over 800 Episodes Published

Donald Kelly, The Sales Evangelist Podcast, 800th EpisodeToday’s podcast celebrates the very best sales tips we’ve learned in the previous 799 episodes of The Sales Evangelist podcast.

I’ve pulled together the best sales tips I’ve heard on the show, as well as some details about how I got started in sales and why it matters so much to me. We also discuss where we’re headed next and the new things you can expect from us in the coming months.

From our first 799 podcasts:

Overcome self-doubt.

In episode 001, Jared Easley, host of Starve the Doubts podcast, and Jeffrey Gitomer, author of The Little Red Book of Selling, discussed self-doubt, and the ways to overcome the self-doubt that plagues people in all industries: sales, business, even life.

Gitomer shared the impact of growing up in a family where people made their own money. Because he grew up around it, he assumed he would do the same.

The people around him were successful, so he assumed he would be successful as well. He never doubted himself, even when he went broke.

From that, Gitomer explained the importance of surrounding yourself with people who are achieving great things. Spend time around top performers and see what you can learn.

Take action.

Serial entrepreneur Ralph Quintero challenged us to do the things we know we need to do as sales professionals that will bring us success and happiness.

We should begin by looking at numbers, because they don’t lie. If we make 10 phone calls but convert only 2 of them, those numbers don’t lie.

Perhaps we’re allowing our fear of rejection to keep us in the office instead of getting in front of prospects. Maybe we’re staying out of the office to avoid working the phone.

If you are’t constantly hustling, you may be the reason you aren’t achieving the success you desire.

Understand buyers.

Many of us mistakenly believe that buyers make decisions based upon products, services, brand, pricing, or other variables.

Jill Konrath challenges that notion with research that indicates buyers make decisions based upon their experience with their sales person.

The more information you have about your buyers, his priorities and plans, his obstacles and challenges, his processes, and his finances, the better equipped you’ll be to bring insights and information that can help him meet his objectives.

Be human.

Jon Buchan shares his genius copywriting experiences with salespeople who are engaging in cold contacts.

He takes advantage of the fact that his prospects don’t know his name and he uses it to inject humor and honesty into his cold emails.

My name is Jon. You don’t know me because I got your name from a list, but at least that means you’re list-worthy, right?

Because his emails begin with such brutal, unexpected honesty, he has credibility in the eye of the prospect. Additionally, he has made them smile and he has piqued their curiosity.

Be human. You’ll stand out from the others.

Prioritize presentation.

Patricia Fripp came to the U.S. with $500 and made a name for herself as a woman specializing in men’s hairstyling.

She started her own business when she was 30, and she invested time and resources in several speaking courses at the urging of her mentors.

When she was 39, she sold her hairstyling business and started a business as a keynote speaker, which led her to work with sales professionals who seek to improve their sales presentations.

Her clients realized that they were in danger of losing large deals, not because of price or offering, but because of presentations. As a result, Fripp teaches sales reps to sound more professional, more personable, more persuasive, and to connect better with clients.

Join our community.

Each of us has our own niche in sales, and we often get into our silos and focus on our own industry. Other professionals are selling successfully in other industries like cars or advertising.

If those people are doing something that might benefit you, wouldn’t you want to try it?

The The Sales Evangelist Hustler’s League is an online group coaching program that brings together sellers from all over the world to share training, exchange sales tips and grows in their careers.

Moving forward, time limitations will restrict the number of one-on-one coaching commitments we can accept because we always want to focus on quality. F

We’ll be adding a second podcast in April and we’ll work with companies later this year to generate leads, create opt-ins, and develop business.

We hope you’ll join our Facebook group The Sales Evangelizers. 

We also hope you’ll share this podcast with others who can benefit from it, and that you’ll leave us a review wherever you consume this content. If you haven’t already, subscribe to this podcast so you’ll benefit from all the things we have learned and will continue to learn.

Episode Resources

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