Basketball Pro Dre Baldwin: How To Be Great At Sales Without Seeming Salesy

Authority Magazine
Jul 31, 2020 · 11 min read

The concept is simple: note everything that is part of your offer and what it’s worth to your prospect to make their decision a no brainer. It’s way of building momentum for them to easily say “Yes.”

a part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Dre Baldwin.

Dre is a former 9-year pro basketball player who traveled 8 countries in his career after walking on at an NCAA Division 3 school.

Dre is now a full-time entrepreneur who has authored 27 books and performed 4 TEDxTalks on Discipline, Confidence, Mental Toughness & Personal Initiative. He has over 135,000 subscribers on YouTube, and his daily Work On Your Game podcast has been downloaded over 3 million times.

Dre built his company, Work On Your Game Inc. on giving as much “game” as possible to many people as possible.

Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

hanks for having me! One thing I learned early in life is that everything is a sale. Making a sports team is a sale. Getting a date. Getting people to listen to you. Cleaning your house when you have guests visiting… they’re all sales.

Knowing this, I would read books about business and sales as a kid, and when I was introduced to the concept of entrepreneurship, I was immediately drawn in: your income is based on selling your value to those who need it. Perfect for me!

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

The most interesting experience of my life in sales would be two things that happened, about ten years apart.

The first was when I hopped on eBay and started selling items like out-of-print, no-copyright books for $0.99 cents apiece — and it actually worked. I knew nothing about keyword optimization or copywriting, but I did learn some things along the way by simply modeling what I saw on others’ listings.

And my book listings were selling.

That taught me that having the right product, along with the right “pitch” to get people’s attention (in this case it was the product listing headline) led to sales.

The second experience was in the early years of social media and content creation. I had a small-but-growing audience on YouTube and was known for basketball training content.

Players continually asked me for programs they could follow so they could work on their games — I finally got the hint and started creating and selling my own programs.

I quickly realized that what I’d stumbled upon — creating products from an idea and selling them to an eager audience — would be the most valuable activity of my life.

Are you working on any exciting new projects now? How do you think that will help people?

Right now my focus is on The Overseas Basketball Blueprint, which provides a complete framework for basketball players to play professionally worldwide, and guides them through every aspect of their careers.

Any player who’s serious about going pro can get a free copy of The Overseas Basketball Blueprint Book at

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

That person is Robert Kiyosaki.

While I’ve never met the man, his book Rich Dad Poor Dad was the key to me angling towards entrepreneurship rather than a “regular” job after school (with respect to a 9-year detour in professional basketball).

I grew up around career employees, and none of them ever seemed to have money for anything after food, clothing and shelter. I heard things like, “we’re not rich” and “money doesn’t grow on trees.” I was trained to not ask for anything that my parents may not have been able to afford so as not to embarrass them, which led to being the target of their ire.

The thing was, I saw other people, along with their cars and homes, who seemed to have money to do whatever they wanted — like buying their kids “extra” stuff, going on vacations, and having multiple cars in one household. I wanted to know what those people were doing that the adults around me were not doing.

Robert Kiyosaki’s book opened my eyes to what those other people, who appeared “rich” to me, might have been doing. If nothing else, it helped me understand that trading time for money had its limits — I don’t like limits.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

My credibility in the sales world comes from the fact that I’ve been creating, marketing and selling my own products for over a decade, and have owned my business Work On Your Game Inc. for just as long.

We generate revenue only when we exchange our goods and services for money; i.e. when we make sales.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts of the news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

Here’s an easy one: STOP watching the news!

“The news” isn’t the news anymore.

The news was designed to offer objective, factual information about what was happening, and to leave the consumer to draw their own conclusions as to what that objective information meant.

Today, name one objective news outlet. They’re dwindling by the day. News shows are more like talk shows now, giving you some fact mixed in with a lot of opinion and presented as “truth.”

A news outlet’s only aim is to keep you fearful and anxious — so you have to keep coming back to them to get an update on the things you’re afraid of. That’s how they stay in business.

All of that said, when there is real news happening, it will find you — you won’t have to go looking for it.

Once you have “the news” out of your life, find something to occupy your mind.

I don’t care if it’s spending time with family, taking up a new hobby with your free time, or if you are able to, work from home. Give yourself a reason to get out of bed in the morning. It’s hard to feel positive and excited about life when you don’t have anything to do.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Because the traditional educational system was created to create employees — and traditional thinking seems to believe that the only people who have to sell are those with “sales” in their job title.

You and I both know that this could not be further from the truth.

Another reason is that a sales career appears risky next to a job that comes with a supposedly “guaranteed” paycheck. In sales, the traditional wisdom says, you never know when you’ll make money.

Most people want no part of that life. And school is designed to train the masses.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesy”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

Yes — and No!

On one hand, everything is sales. Everything we do in life is effectively a sale. Any time we aim to influence or persuade another person, we are selling. Anyone who doesn’t like the idea of “sales” doesn’t like getting their way in life!

On the other hand, though, many people don’t look at things as practically as what I explained: they see sales as what some unethical people do to make others buy stuff that they don’t necessarily want.

The bottom line is this: life is competitive. If you’re unwilling to be a bit pushy or aggressive (defined as “forcefully going after what you want”) in pursuit of your aims, you won’t get them.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?


I have always had a natural inclination for public speaking, starting with playing Brutus in “Julius Caesar” back in third grade.

Nowadays as a professional speaker and content creator of thousands of videos and audio MasterClasses, I use this skill literally every day.

My favorite thing about presentation is that it’s performance art; people who have a flair for what they do will always do well with presentation, as long as they know their product. I can invoke my personality and energy into it.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, but can you share some of the fundamental strategies you use to generate good, qualified leads?

One way is to pay for them! Haha… Facebook has a robust platform for targeting the exact person you’re aiming for.

Another is via specifically targeted content. This can be done via podcast, blog post or video. Include with your content an irresistible offer — usually free of charge — in exchange for someone’s contact information. This tried and true method has worked for as long as sales has existed.

One more way is to borrow the audience of someone else by collaborating with them. This can be in the form of guest posting, making a piece of content together, interviewing them (and having them promote the interview to their audience), or them interviewing you — like we’re doing right now!

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for many people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

It’s difficult for many people because it hints at the energy of disagreement or confrontation, and many people are deathly afraid of both!

To be better at handling objections, all a salesperson needs to do is get experience handling them.

Role play with a colleague who tosses every possible objection at you, and the two of you take turns handling them, swapping tips.

After every presentation, take note of every objection you’ve heard and role play handling them until you’ve literally “heard it all.”

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

1) Ask for the sale. Funny thing: many sales people never actually ask for the sale or make it clear to their prospects what they want the prospect to do! As Zig Ziglar said, timid salespeople have skinny kids.

When I worked in gyms selling memberships, I always concluded my presentations with, “are you ready to get started?”

2) Recap what you’re offering. In digital marketing, I’ve heard this referred to as “stacking.”

The concept is simple: note everything that is part of your offer and what it’s worth to your prospect to make their decision a no brainer. It’s way of building momentum for them to easily say “Yes.”

At the gym, for example, I’d mention the convenient hours of the gym, the use of the pool, how clean we kept the locker rooms, the 50 classes offered every week, the waived initiation fee, and the free personal training assessment the prospect would get immediately upon joining…

And I’d personalize every element of the stack based on the needs the prospect had already shared.

3) Be armed to handle objections. Not every prospect is going to be ready to say yes immediately. Some will have objections, complaints or questions.

If you’re well prepared, you will anticipate these statements and be ready to handle them (or, even better, have already handled them before the prospect brings them up).

4) Have your homework done. Know your prospect and their needs better than they do. Know how your offering solves their problems, and emphasize those elements as much as you can.

Anticipate objections and handle them before they’re voiced by your prospect.

5) Be ready for follow-up. Since no salesperson closes every deal upon first contact, have your follow-up process in place.

Know when and through what mediums you’ll be following up with any prospect who does not close.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

Follow up is 90% of the game!

Most sales, depending on size of the transaction, do not close upon first contact. Even when I sell $7 products, people leave and come back 48 hours later to buy. When we fail to follow up, we are letting money walk away from us.

The follow-up process should be systematized and routine when it comes to when and how we follow up, and it should be tested regularly to be optimized.

I don’t worry about being too pushy in following up; a person who wants my product will appreciate my persistence. Someone who isn’t going to buy is not buying no matter what you do.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

In person is always the best method of communication, period, whether making a sale or not.


Because most of communication is non-verbal, and we can intuit many things via in-person dialogue that we can’t get any other way. A person’s body language and energy tell us a lot more than a person’s words.

Even a phone call cannot show us body language, but it does have voice, and it’s the next-best way to communicate when you can’t see someone in person.

I like to communicate with people as directly as possible.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. :-)

My current movement, “Work On Your Game”. It’s based on taking the mentality of the professional athlete and applying those Mental Game tools to business, sports and life.

How can our readers follow you online?

On Instagram @DreBaldwin, and my website

Thank you for the interview. We wish you only continued success!

Thanks a lot, I had a great time with you all!

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