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Salesman.com
The Salesman.com podcast feed gives you the worlds best sales content. Salesman Podcast – The Salesman Podcast is the worlds most downloaded B2B sales podcast and is an Apple Award winning show. It helps sales professionals learn how to find buyers and win business from them in a modern, effective, and ethical way. The show has featured NASA astronauts, F1 drivers, Olympic athletes, UFC fighters, world leading neuroscientists and the world’s top sales experts as guests. Selling Made Simple – Sometimes sales professionals just don’t have the time to listen to an hour of content. This is where Selling Made simple comes in with its 10-minute, practical episodes.
Episodes
Mentioned books

Jun 13, 2022 • 15min
The Rocky Road to Becoming a Sales MILLIONAIRE | Selling Made Simple
Money! We all love it. We all want it. And we all never seem to have enough of it.
Sam here tried his hand at sales because of the earning potential. But he quickly dropped out due to the stress.
But Walter knew that if you could push through the downsides, you could bring in a massive income. We’re talking MILLIONS. And he also learned the tricks to make earning beefy commissions easier than ever.
And that’s what we’re covering today—the risks, the rewards, and the simple steps you can follow to become a sales millionaire.
Now, working in sales is no picnic by any means.
On the one hand, there’s the rejection. Which sorry to say, is typically a given. The better you get, the less of a problem it becomes, sure. But first starting out, you’re going to get some no’s.
On top of that, the cold calling and cold emailing can be monotonous at times.
But by and large, the toughest thing about sales is this—you are the one responsible for your pay. If you suck, you sink. And for some, that can be a terrifying prospect. Because if you slack off, you aren’t guaranteed the paycheck you’ve come to depend on.
A sales career isn’t a cakewalk. That much is clear. But there are some serious benefits to it too. Benefits that no other career can offer.
And today, that’s what we’re talking about. The upsides. The reason why sales is in my opinion, so special. So exciting. And so fulfilling.
So let’s jump into it.
A) Quickest Way to Make Money
It’s the quickest way to make money. There are other careers that may get you to that 7-figure level at some point. But sales is without a doubt the fastest. So, why is that?
1. Product Development’s Done Already
The hard work’s done. Your brand’s already spent the time, the money, and the effort to create a working product. And they’ve built connections with vendors, distributors, and regulatory agencies to handle all those sticky logistics.
All you have to do is sell it!
2. You Can Stay Mobile
You can stay mobile. Sales skills tend to transfer cleanly from one company, market, and even industry to another. If you were killing at company A, you’ll probably kill it at company B too.
So once you’ve built up a proven success record, you can easily move on to a more profitable company. Working your way up and up until you’re at an employer and salary that’s a fit for your goals.
There aren’t a lot of other positions that allow for this level of mobility. So take advantage.
3. Brand Leverage
Brand leverage. One of the great things about sales is you can leverage the social proof of the brand you’re working for.
If you’re working with one that’s established, they already have a customer base. They’ve got a market. And they’ve probably got case studies, success stories, and testimonials that you can distribute to potential buyers.
If you were to say, start your own business, you’d have to toil away for years to make a name for yourself. But as a rep, that hard work’s already done for you.
4. Inbound Sales Leads
Inbound sales leads. In all likelihood, your brand will have a marketing department. And that marketing department will literally feed you leads. That’s their entire purpose—to send qualified buyers to your doorstep.
And if they do things right, that means you don’t have to work nearly as hard to get prospects knocking on your door.
Alright so let’s get into the second reason sales can be such a great career.
B) Least Risky Way to Make Money
It’s the least risky way to make money. With other money-making ventures, risk is a serious factor. In many cases, the risks outweigh the earning potential. And if they don’t, it’s usually because the pay isn’t all that great to begin with.
You Can Become Unsackable
See, every business knows the value of a great sales rep. We are the lead moneymakers, the final step between selling and sold. And there is a direct and easily observable correlation between a bad rep and a good one—good ones bring in more money.
That’s why a quality rep is such a secure position. There’s not an iota of confusion about your contribution to the company. So as a rep, you’re likely going to be one of the last employees to go on the chopping block.
On top of all that though, your competitors will proactively try to poach you. That means if you do get fired, it’s an easy path to another job. Plus, you can leverage their offers for a raise at your own.
It’s also the least risky way to make money because…
The Alternative is to Start Your Own Business
The alternative is to start your own business. When you boil it down to earning potential and speed of making your first million, creating a business for yourself is the only real alternative to a sales position.
And there are some very real downsides here.
First you’ve got to develop a product. That can take years and years of brainstorming, rigorous testing, partnering with the right vendors, blah blah blah. You see how this can take forever.
But even when you do develop a product, you’ve still got to build awareness around it AND, surprise surprise, you have to be good at SELLING that product anyhow! It all comes back down to sales, doesn’t it?
And finally, most importantly, most businesses just don’t make it that long. The U.S. Bureau of Labor Statistics reports that one out of five businesses go under in their first year. Only half make it to year five. And by year ten, 2 out of 3 are kaput.
So when it comes to the best alternative to sales in order to make your millions, the odds are just stacked against you.
Let’s move onto the third reason for sales being such a great moneymaker.
C) Simplest Way to Make Money
It’s the simplest way to make money… if you know what you’re doing that is.
Here’s why. Once you get good at it, it actually becomes easier to make more money. For instance, once you make a name for yourself, you can start selling products that are…
Well Known, Easy to Explain, High Value
Well known products already have great marketing and inbound lead generation systems in place. Think of platforms like HubSpot CRM. Practically every business owner already knows about HubSpot. And that means selling prospects on its value doesn’t take much work at all, making your life 100% easier.
Easy to explain products have strong messaging. And they’ve already broken through to the mainstream. There’s no question about what they do. Because everyone already understands it! Think DHL here with their tagline, “Excellence. Simply Delivered.”
And last but not least, once you get good at sales, you can also work with products that have a high value. These are the products where it’s easy to show a strong ROI. And that means less squabbling over budget problems.
The Selling Made Simple Academy, for example, has a very clear value proposition—find and close more sales in the next 30 days or your money back. It’s as easy as that.
Strong, Proven, Repeatable Sales Process
This is a process you can use every day that’ll consistently let you blow past quotas. And it’s a process that lets you scale your earning potential rather than keeping your income level set.
For you, that means no more guesswork. No more struggling with meeting your numbers. And no more hoping this next call is the one.
Instead, it’s a system you know works. And it’s giving you more financial freedom than ever.
Now, there are plenty of sales methodologies out there. But obviously we recommend the Selling Made Simple Academy. This academy uses easy-to-follow yet highly actionable selling frameworks that, well, make selling simple.
And it’s helped literally thousands of sales reps just like you up their game and earn more than they thought possible.
So if you’re interested, I recommend having a look today over at Salesman.org.
Summary
Now I know, sales can be tough. There’s rejection, monotony on some days, and your pay largely depends on your own abilities. If you suck, you sink. And that can be scary for some. But the downsides come with a major upside—the opportunity for making serious bank.
So don’t be fooled here—sales can suck. But when you know what you’re doing, it can hands down be the most lucrative and fulfilling career of your life. No question about it.

Jun 8, 2022 • 11min
SALES Is Just Like DATING... | Selling Made Simple
Question for you—what do a product demo and a candle-lit dinner have in common?
As it turns out, more than you might think. See, sales is a lot like dating. If you jump into a sales call by bragging and boasting about your product, your buyer is going to immediately lose interest.
But just like in the dating world, there are a few things you can do to make closing much more of a success. And today, we’re talking about three in particular.
So we’ve all been out on a nightmare date before, right? Think back—what was so bad about it? In all likelihood, it was that the person on the other side of the table just wouldn’t stop blabbing about themselves. How much they make. What they can bench press. Who they’re friends with. It’s exhausting just talking about it.
Or maybe that’s been YOU in the past?
But the thing is if you can get the other person talking, feeling good, and sharing what they’re working towards, you’re one thousand percent more likely to build a deep connection.
The same goes for saless.
So, let’s start with maybe the most impactful step you can take to boost your chances of success, both in love and in sales…
Ask, Don’t Tell
To be perfectly honest, your buyers don’t really give a shit about your company or your product. They may eventually, sure. But in the initial stages of the sales cycle, the ones that focus on awareness, the key is to turn the focus on them. You’ll have plenty of time to point to all that juicy social proof when it comes to the decision stage.
So instead of telling prospects about yourself, ask more questions. Now, there are three very real benefits to taking this approach.
1. You Better Understand Their Problem
You better understand their problem. When you’re talking, you’re not listening. And that means you’re not taking in as much info as possible about the problems your prospect is facing. As a result, you’re missing a valuable opportunity to understand their pain points. And an opportunity to find the RIGHT solution for them.
2. You Qualify Them As Ideal Clients
You qualify them as ideal clients. The more you learn about a prospect, the more info you can gather about them. What’s their budget? What kind of timeline do they have? Does their problem even match up with your solution? These are all critical questions you need answers to. Because these are the answers that let you know if this client is right for your business or, frankly, if they’re a waste of time.
3. You Connect Their Emotions
You connect their emotions. Logic plays an enormous factor in B2B buying decisions. But that doesn’t mean emotion doesn’t come into play too.
President and CEO of Whetstone Inc., Adrian Davis, put it to me like this:
“Fundamentally, we make decisions emotionally, and if all we're doing is spouting features and benefits, we're really engaging the logical part of the brain. The logical part of the brain does not make decisions. But analyses and captures information to weigh pros and cons, but decisions are made emotionally.”
When you get prospects talking about their problems, they get invested emotionally in solving those problems. And that means you’re engaging with them using both sides of the coin—logic and emotion.
The #1 Turnoff
The number one turnoff. And like I hinted before, this one overlaps pretty well with the dating world. So, what do you think it is? The top turnoff for both sales and dating?
Bad Breath
No kidding! Now while the worst lingering aroma on your breath while dating is garlic or onions, in sales the worst smell is—commission.
Yep, commission breath. It’s sunk countless sales in the past. And if your buyer catches even a whiff of it, they’re bound to leave you high and dry.
Commission breath is basically when you come off too needy, too desperate. You NEED that sale. And it’s showing. When a buyer sees that desperation, they’re way less likely to trust you. And they’re way less likely to buy from you.
So, how do you kill commission breath? Well, there are three ways in particular.
1. Understand You’re Selling Value
Understand you’re selling value. Your product isn’t some throwaway piece of trash. It isn’t some waste of money. And it does in fact have value for businesses. So don’t come into a sale hoping, begging to close. Because after all, the only thing you’re doing here is trading value.
2. Build Your Self-Respect
Build your self-respect. Now this one isn’t a quick fix. And confidence doesn’t develop overnight. But what I can say is that we at the Selling Made Simple Academy have a framework dedicated specifically to helping reps like you be more confident and assertive on the job. So if you’re interested, I highly suggest checking that out.
3. Re-Evaluate Your Product
Re-evaluate your product. This one’s a tough truth. But it can make the rest of your career far more successful. Ask yourself, is this solution something you can really get behind? Do you really, truly believe it has value? If not, it’s time to start asking yourself some hard questions like, “Do I really want to sell this?” If the answer is no, you may want to find another employer.
Closing – Doing It Wrong?
In the dating world, it’d be just plain weird to end a great date by saying, “Whelp, that was fantastic. Email me if you’re interested in getting together again!”
Ridiculous, right? Instead, you want to seal the deal. Not like that. Get your head out of the gutter! But I’m talking setting up the next date. You want to close on the next steps. The next date.
Same goes for sales. Rather than leaving the next steps up in the air, you want to close on your next meeting—a discovery call, a product demo, a tech spec deep-dive, whatever!
And to do that, I have one little phrase for you…
“Does It Make Sense To…”
This is the ultimate closing phrase that’s perfect for any phase of the sales cycle. Does it make sense to draw up the paperwork, have a demo call, look at some case studies? It doesn’t matter what stage you’re in.
If things aren’t quite right on your buyer’s end, they’ll say no and you can follow up questioning why. Simple!
This is the perfect closing question because it keeps things mutual, it identifies any roadblocks, and it lets prospects know exactly where they’re at.
So give it a try.
And that, my friends, is a perfect recipe for winning your second date.
As you can see, dating has a lot more in common with sales than most people realize.

Jun 3, 2022 • 16min
WIN The Most Important Part Of Cold Calls | Selling Made Simple
The fate of your deal rests in the first four seconds of the sales call. That’s it. If you can nail the first 4 seconds, often the deal is as good as yours. Why is that? It’s because of the importance of first impressions…
Sales rep Sam, for example, always botched his first impressions. So, even though he was selling a solid product, buyers never stayed interested long enough to hear about it.
But Walter knew the importance of a strong first impression. He knew by immediately playing the three specific roles we’re talking about in this video, he’d always win over his prospects.
And guess what? If you implement the 3 roles we’re going to cover, you can do the same too.
Now, first impressions. They set the foundation for the rest of your sales call. If you come off as a commission-hungry sleaze, good luck earning trust with your buyer.
First impressions count. And they form almost instantly, as soon as 33 milliseconds according to some studies.
For sales reps like you, they’re even more important than people in an average job. Because your buyers are busy. And in the short time they give you, you need to build up rapport especially quickly.
So the question is, how do you do it? How can you win over prospects in the first four seconds of a sales call?
It all comes down to playing three key roles. And the first role you need to play is that of…
1. Be the Expert
The expert. If you’re coming off unprofessional or unknowledgeable right off the bat, a buyer isn’t going to waste their time listening to anything you have to say. And if they do, they’re probably just waiting for their chance to leave.
So how do you prove to them that you do, in fact, know what you’re talking about here? Two words—Social. Proof.
Social proof is key to demonstrating your expertise before you ever even get on the call. And there are three specific ways to show that social proof.
A) LinkedIn
First up is LinkedIn. The LinkedIn platform is fantastic for demoing social proof. Endorsements, testimonials, credentials—buyers can see all of it in just a few clicks. But beyond that, they can also get a look at the thought leadership content you should be creating.
So be sure you’ve created a complete profile here. Ask for endorsements. Put out original content regularly. And check in once a day or so to stay active. It doesn’t have to take more than 15 minutes.
Now if you’re social selling, buyers coming through the platform should see your page immediately. But if you’re not, I’ve got a tip coming up that’ll boost the odds of your prospects checking out your LinkedIn page.
B) Network
Network. Who you associate with says a lot about who you are. Are you connected with big names in the industry? Have you worked with top players before? What brands have you sold for and to?
A smart buyer will do their homework before setting up a call with you. And they’re sure to check out who you’re connected with, most likely through LinkedIn.
But if you’re especially savvy, you’ll have your own website set up that prospects can look through. Here you can house all your thought leadership content as well as your experience, testimonials from clients, and endorsements.
So make sure you’re doing the work of collecting this kind of social proof from your clients. Because they can do wonders for trust-building before you hop on the sales call.
C) Setup Email
Setup Email. This is the sales call confirmation email that buyers will get after booking a time with you.
Typically this email will include all the basic info. We’re talking time and date, agenda, and a few words on what else buyers can expect.
But this email is the perfect place to include some pieces of social proof to start the trust-building process. A testimonial here. A success stat there. Nothing too over the top. You don’t want to come in too strong.
Your signature line is also a great place to include links to your website, testimonials, and LinkedIn profile.
And finally, you could even point them to a piece of content you created within the email.
2. Be the Equal
The equal. A successful relationship is one that’s built on equality. Each member needs to give and take equally. And if your buyer is the one with all the power, they’ll never give you the respect and consideration you deserve.
That’s why you need to be the equal here.
A) You Are Serious
You are serious. You aren’t some second-rate sales rep that’s pestering prospects into buying. And you aren’t sending hordes of desperate emails or calling five times a day.
Nope, you’re a professional. And to make sure that comes through, there are a few things you can do.
First, put some effort into your appearance. Clean, smart clothing. Impeccable hygiene—comb that hair. And equipment and a camera background that says, “Hey, I do this for a living. And I take this seriously.”
Second, come prepared. Sending out an agenda beforehand is a must. And showing up on time, with all your necessary materials in-hand, is key.
And finally, get to the point. A bit of small talk is fine. But don’t let things go on for too long. Your buyer’s time is valuable. And so is yours.
2. You Aren’t a Crook
You aren’t a crook. And you don’t have to trick prospects into buying from you. That’s because you have real value to exchange here. A lot of the work being done here comes from the social proof you’ve shared before the call.
But you can also tweak your language to build trust. Stay away from getting too personal or friendly early on in the relationship. Keep communication professional—no swears or inappropriate stories. And don’t badmouth your competition. It might be tempting to bring a competitor down to boost yourself up. But doing so makes your own business come off shady.
And the third way to show you’re an equal is by proving…
B) You Are Assertive
You are assertive. You don’t let the prospect walk all over you. You can start by taking control of the call at the outset. Be the first to show up, the first to talk, and the one to set the agenda.
Depending on the buyer, you may hit a bit of resistance. But don’t give up control here.
For instance, when clients try to take hold of the conversation or steer away from the agenda, simply say, “This is the way these things normally work,” and redirect the conversation. If they do it again, pause, and then repeat. They’ll get the point.
This is your show here. So act like it.
Now, the final role you’ve got to play on calls is
3. Be of Value
A rep that has value. You’re an expert so you’re not wasting their time. You’re an equal so you’re worth listening to. And you have value, so you have what it takes to make your buyer’s life easier. They just have to listen up.
A) Your Product Is Solid
Your product is solid. Testimonials, credentials, awards, referrals, and other social proof nuggets are powerful here. Your product works! And here’s the info to prove it.
But you may want to take things a step further too. In the agenda confirmation email, try pointing them to a bit of light reading on your product before they jump on the call. It could be product details, case studies, even blog posts. Whatever it is, you want your buyer to come into the call confident that what you’re selling isn’t a sham. And in fact, it might be the exact solution they’re looking for.
B) You Are Knowledgeable
You are knowledgeable. The old “It practically sells itself!” saying is bull. Any sale, no matter how great the product, can be completely ruined by an unknowledgeable sales rep. Because even in the high-logic world of B2B sales, buyers still need to work with someone who knows what they’re talking about.
And if they catch even a whiff of you fudging numbers, getting product details wrong, misunderstanding use cases, or generally not knowing what it is your product does, they’re going to head for the hills. And fast.
So make sure you’re doing your due diligence beforehand. Or else you might end up looking like a fool.
C) You’ve Done Your Research
You’ve done your research. You need to show that you know you can specifically help the person you’re talking to.
What problems is their business currently facing? What issues are cropping up across the industry? How are their competitors handling these changes? These are all must-knows here.
Because the more specifically you can cater your product’s benefits to your buyer’s exact needs, the closer to closing you’ll be.
LinkedIn is a great research tool here. Dive into what types of content the buyer’s been sharing, creating, and commenting on. Get a feel for what they’re focusing on before the call.
And if you’ve helped a business like them in the past, send over case studies or some numbers beforehand. That way they’re getting on the call knowing you’ve helped someone similar in the past.
Summary
So, to win over your prospects in the first 4 seconds of your sales calls you need to –
1. Be the Expert
First, be the expert. LinkedIn, networking, and including social proof in the call setup email are your friends here.
2. Be the Equal
Be the equal. Remember, that one, you are not another pesky salesperson chasing and pestering the prospect. Two, you’ve made it clear you have value to exchange. And three, you aren’t some sort of pushover.
3. Be of Value
Be of value. You’ve got a solid product. You’re knowledgeable. And you’ve done your research.
And when you’re able to play all three roles the instant you step on your sales call, you’ll immediately be building rapport, earning trust, and boosting your odds of closing.

May 27, 2022 • 18min
How I Close COMPLEX Sales In A SINGLE Call | Selling Made Simple
In sales, the general rule of thumb is, the more complex the product, the longer the sales cycle.
And for some complex products, that might be true. But for others, a single phone call is all it takes to get a deal done.
I close complex training and consulting packages with some of the brightest companies in the world. And usually, I do it over a single conversation. Yep, I have one phone call with the prospect and then send the invoice.
Most salespeople think this is impossible. But with the right step-by-step, single call structure, you too can start closing your deals quicker than ever before.
So the business-winning phone call isn’t a sales myth. It isn’t sales folklore. And it isn’t an old wives’ tale. But it is misunderstood. See, you can’t get any old buyer on the phone and close them in a single conversation.
No, they have to be the right buyer. And the real trouble, the thing that should take the most effort, the most thought, and the most time is qualification. A survey from HubSpot found that the number one challenge for one out of three sales reps is lead qualification. And it’s true, doing it right is tough.
That’s why with the Diagnosis framework we’re going to first discover the pain that the prospect is in, qualify them to see if we should be doing business with them and then close them, in that order.
Most salespeople do this over multiple calls, over multiple weeks. This framework will show you how to do this in just one call and then close the prospect at the end.
The first step is to understand the buyers…
1. Pain
Pain. Is this potential buyer actually in pain right now? Is their problem actually a problem at all?
The buyers you want to work with are feeling the hurt from this problem. And as a result, they’re going to be highly motivated to find the right solution.
Now, a few qualifying questions to ask that’ll get to the bottom of their pain are…
“You booked this call with me today, what led to getting this call booked in?” and…
“What’s stopping you from solving this issue yourself?”
Both of these questions should help you get to how big this problem really is for the buyer.
2. Time
Time. Not all problem and solution timelines are going to line up. And one of your primary concerns when qualifying prospects is what their timeline is for when they need their problem solved.
Are they thinking today? This quarter? Or in the next few years?
If your buyer doesn’t have urgency, they won’t be compelled to act. And as a result, you’ll likely encounter plenty of feet dragging and time-wasting along the way. Best instead to say you’re not a fit early on.
As for qualifying questions here, start with…
“Do you have a deadline to solve this?”
It’s straightforward, I know. But the answer will give you a clear, no-bullshit timeline that you can work with.
3. Fit
Fit. Can you actually fix this buyer’s problem?
The truth of the matter is there’s no perfect product or service for everyone. And saying otherwise is just playing into the public’s idea of sales reps being con men.
Instead, it’s your job to think of yourself as someone who offers value. And you shouldn’t have to waste time with someone who doesn’t need what you’re selling.
Qualifying questions here are for YOU this time, not the buyer. So ask yourself…
“Do I have the solution for this buyer’s problem?” and…
“Do they really need this solution?”
4. Return
Return. There’s a downside to any solution. Buyers need to change vendors, hire new staff, train on novel systems, or fight for a change to the budget.
The question is, is the value your solution provides worth that discomfort?
How much will they have to change to accommodate it? And when all is said and done, will they look back on the investment as a good purchase or one that ate up too many resources?
Going through this calculation upfront is a must during qualification of sales leads
For qualifying questions here, try…
“How would things be different if we solved this for you?”
“What is your motivation to make this happen?”
“If we took your business from $X to $X, how would that change things?”
These three questions will help you parse out whether your buyer’s willing to put in the effort needed to make this a success.
5. Process
Process. As an expert on your product, you know what it takes to make using it a success.
But does the buyer know how things are purchased in their organization? Do they know who needs to be involved? What training needs to be done? What process did you need to follow to get the project implemented.
You can uncover this by asking…
“When your organization has done similar projects in the past, what paperwork process needed to happen?”
This will give you a clearer idea of what lies ahead should the buyer be a reasonable fit.
6. Budget
Budget. As touchy of a subject as budget can be, it’s absolutely essential that you get a feel for your buyer’s budget before you start working with them.
Now, that doesn’t mean you have to lead the call with questions about money. And in fact, doing so may turn off the prospect from the outset, sinking any hopes of a deal.
Instead, lead up to budgetary questions. Handle the subject professionally and use direct communication. Think of it as just another aspect of the qualification process.
And use these questions to get the necessary details without scaring off the buyer.
“How are projects like this funded?”
“Is a project like this in this year’s budget?”
“What financial scope do you have to solve this issue?”
7. Champion
Champion. With sales, your buyer’s decision is often going to be influenced by other individuals in the business. It could be heads of other departments, higher-ups in the C-suite, or even influential team members below them.
That’s why it’s important to figure out who these other individuals (or “champions”) are before you decide the buyer’s a fit.
Doing so clues you into whether the buyer is the final decision maker and if there’s someone else you should be talking to instead.
The main qualifying question here should be…
“Who is the person that people look up to within your department on projects like this?”
This subtle approach will help you uncover any other decision-makers that may influence the passing of the deal.
8. Agreement
Agreement. As a sales professional, it’s up to you to get your buyer’s verbal commitment on the call. Otherwise, they’re liable to walk away after days or even weeks of your hard work, leaving you out weeks or even months of hard work.
So when you’ve determined that a buyer is a solid lead, don’t hang up the phone before asking this discovery call question.
“You’re a good fit to work with us. If we can solve X, will you commit to Y?”
This time-tested formula has it all—validation, a hint of flattery, results anchoring. By asking this question, you’re tying your solution to a specific result. And equally importantly, you’re influencing the buyer to commit to that solution, provided you can achieve the results you promise.
After that, the only thing left to do is nail down the specifics and sign the papers.
Summary
No matter how complex your product is, how many moving parts your solution may have, it is possible to win business on a single call. All it takes is asking the right questions and qualifying prospects according to the right structure.

May 23, 2022 • 16min
Never Again Wonder “Are They Going To Buy?” | Selling Made Simple
Invisibility, flight, laser eyes… NONE of these superpowers compare to the #1 superpower for sales reps—which is the ability to read minds…
Because when you can read your prospect’s mind, you can give them exactly what they’re looking for. And that means more closed deals, better commissions, and a bank account even Bruce Wayne would be jealous of.
Today I’m showing you how to become a sales superhero by learning how to read your prospect’s mind. In this video you’re going to learn 6 ways to understand exactly what your prospect is thinking.
But before we get into the specifics, let’s talk about verbal language.
Language is an amazing tool for connecting and communicating with others. It lets us share ideas, vent frustrations and, solve mutual problems, But even still, Words alone have limitations. And context, history, and individual experience all can change a word’s meaning from one person to the next.
Luckily, according to the research, around 70% of our communication doesn’t rely on words. And equally lucky, our brains are equipped with the ability to read nonverbal communication effectively . we can use non verbal communication to understand what someone else is thinking without them ever saying a single word!
So, what do you need to do to become a better mind reader?
3 Internal Tactics
1) Establish a Baseline
Establish a baseline. This one has its roots deep in the world of science and evidence. Here’s why.
When you’re creating an experiment, say you’re testing the effects of a new pain pill, you need to run at least two versions of that experiment. In one of the experiments you actually give the pain reliever to patients. Duh, right? How else could you tell if the drug worked or not?
But you also have to run what’s called a “control experiment” too. This is where every variable of the experiment is the same. EXCEPT rather than giving the patients the drug, you don’t. You give them a placebo instead,
Why do we also run a control experiment? Because you need something to compare the results of the pain pill against. You need to know how much of the effects are due to the drug itself and how much are due just to the experimental conditions.
And when it comes to becoming a mind reader with your prospects, you need to do the same by establishing their baseline. Do they always have a sweaty brow, or just when they’re lying to you? Do they always speak fast, or only when they’re lying that they’re close to doing a deal with the competition and they’ve only come to you for pricing?
To get a baseline of your prospect, you first need to get them relaxed. Get them talking about something friendly and unassuming, maybe a hobby or the weather. Then study how they’re acting.
This is your baseline. From there, you can look out for changes from this state. Those changes indicate a shift in their mood
Say for example you ask a prospect about a competitor, and they change their posture and start talking faster. That may indicate they’re already working with them. If on the other hand they maintain their baseline and casually say they’re not interested in your competition, then they’re probably telling the truth.
See how that works? So first and foremost, always establish a baseline to help you spot changes in the emotions or actions of the prospect.
2) Ask Assertive Questions
In sales, you need to be clear and assertive with your questions.
For example, let’s take our old friends Sam and Walter the sales reps.
Sam’s got a problem with assertiveness. And when he tries to close, he asks something like this…
“Well, when… er… would you like to get started working with us? I mean if that’s what you choose to do?”
What’s the problem here? A Lack of confidence. And importantly, asking TWO questions—are you choosing to work with us and when would you like to get started?
There’s a lot to unpack for the prospect here. And it’s no wonder a question like this leads Sam’s buyers to give mixed signals, hedge on their promises, and ultimately back out of the deal.
Walter on the other hand is assertive and clear. He asks…
“Does it make sense to sign the contracts today?”
There’s only one way to go from here—yes or no. This reduces the mindreading that you have to do and it makes the buyers opinions clear for you to read.
So take a page from Walter’s book.
And last for the internal mind-reading tactics is…
3) Listening to Your Gut
There is a lot of science around the truth behind “gut feelings”.
In one study from the journal Nature Scientific Reports, Italian scientists filmed a series of short videos of a hand grasping a bottle and either pouring it out or drinking from it. Then, study participants were shown a short 1-second clip of the hand just before it touches the bottle. They were then asked to guess, using their gut feeling, whether the whole video showed the grasper pouring it out or drinking from the bottle.
And guess what? Participants guessed right far above the level of mere chance.
That shows, scientifically, that you should trust your gut feelings when reading your prospects.
And there are countless other studies just like this one too. Our intuition is more powerful than most people give it credit for. This primal response has been honed over millions of years. It’s what kept your ancestors alive. And it’s just as effective in the corporate jungle as it has been in the past.
So if you’re feeling like a prospect is confused, upset, excited, or disengaged but you can’t quite put your finger on why, listen to your gut. And more likely than not, your unconscious mind is picking up on signals your conscious one just can’t see.
Alright let’s shift over to the external tactics. First up here is…
3 External Tactics
1) Studying the Environment
When trying to read your prospects, be on the lookout for environmental cues that hint at your prospects personality, hobbies or motivators . You can then use those cues to round out your idea of who your prospect is. . you can also use their environment as a way to build rapport and open the door to even more friendly, open conversation.
For instance, when I interviewed Andy White, author of MEDDIC for the first time, I noticed he had tons of racing helmets on his bookcase in the background. Now, I could have let that environmental cue go by. But instead, I brought it up. I also happen to like F1, so we had instant rapport because of it.
And because of that rapport, I was able to get a better sense of what Andy was thinking and he was much more open with his thoughts and feelings as a result.
And guess what, you can do the same thing. So be sure to take note of environmental cues. They could be the difference between closing and crashing.
2) Take Note of Their Appearance
What are they wearing? How do they keep themselves? Are they clad in an expensive, jewel-encrusted watch? Wearing a Ferrari owners club T-shirt? Dressed down in a stained sweatshirt with unkempt hair?
These are all valuable details. And they’re all hints that you can use to better read them.
Now to be clear, we’re not looking to see if they “have money”. Lots of super-rich people wear tattered RL polo shirts, after all. But instead, what we’re looking for is their social status. Who are they compared to the people around them?
If for example they’re more dressed down than everyone else in the room, then they are probably the real decision maker here. Best to focus in on them with your pitch. If they’re wearing a Rolex and everyone else looks like students with Apple watches, you should probably approach them differently than the rest.
3) Be Ultra-Aware of Distractions
One of your top goals on a sales call is to command your prospect’s full attention. And if you don’t have it, that means they don’t care about what you’re saying.
Distractions also make it very hard for you to read your prospects too. Because if they’re distracted and they move away from their baseline, you don’t know if it was something you said, or if it was because of whatever else is going on around them.
There are three things you can do here.
First, you can double down on your point to bring the attention back. Really hit on the reason your prospect will benefit personally from working with you here. And hopefully, you can perk up their ears and get them interested.
Second, you can stop and call them out on it. As you might imagine, this one is risky, especially if you haven’t built up a lot of rapport. But in some cases, that assertiveness is enough to make them realize you’re someone worth listening to.
And last, you can reschedule. You can cut the meeting short and agree on a later date so your time isn’t wasted. Sometimes that’s all it takes to get a prospect in the right headspace to see the value in what you’re offering.

May 20, 2022 • 15min
Stop Letting Buyers Walk All Over You | Selling Made Simple
Sales reps have it rough. Besides the endless slog of cold outreach, when you actually do connect with a buyer, you’re told to suck up to them. Smile, dance, give-in—do anything to win the deal.
But what most reps don’t know is that there’s a better way to get what you want from your selling conversations. And best of all, it doesn’t require you to leave your dignity at the door.
“The customer is always right.” We’ve all heard the old saying. And unfortunately, a lot of sales professionals have moved through their careers believing that it was true. That the rep who charms, kowtows, and leaves buyers smiling 100% of the time is the one that kills it month after month.
But what would you say if I told you this age-old rule was… ready? Shit. It’s shit!
It’s just plain wrong. And in fact, bending to a buyer’s will in every single conversation is a surefire way to muck up any sale.
Instead, the trick is to be assertive. And if you’re one of the many professionals out there that isn’t as assertive as they should be, never fear. Because today, we’re looking at how to be a more assertive sales rep.
Now, before we get into the nitty-gritty of it all, let’s first hit on…
Why Assertiveness Is a Must
Why assertiveness is a must in sales. There are five main benefits to being assertive in this industry. First…
A) It Closes More Deals (Duh)
It closes more deals. You don’t get the sale if you don’t ask for the sale. When you lack assertiveness, you lack the confidence you need to push through the awkward yet entirely necessary stages of closing a sale. But as you become more assertive, you’ll find yourself closing more often.
B) It Gives You More Authority
It gives you more authority. The more authoritative you appear, the more likely buyers will be to listen, value your opinion, and look to you as a trusted expert. Consequently, you’ll find yourself having more influence over not just whether they buy. But also what they buy.
C) Communication Improves.
Communication also improves. Tiptoeing around an issue may seem like a good way to soften a blow and keep on your buyer’s good side. But in B2B sales especially, being clear and to the point is a better way to communicate. Your buyers will appreciate you saying outright what you think.
D) Higher Self-Esteem
Assertiveness leads to higher self-esteem. That, in turn, leads to greater job satisfaction, a higher earning potential, and ultimately a happier, healthier home life.
Alright, so how do you become more assertive?
The Assertiveness Training Framework
The Assertiveness Training Framework comes in. Now, if you want to learn more about this framework, be sure to check out the Selling Made Simple Academy. But for today’s purposes, let’s quickly go over the core tenets of this proven framework.
1) Excuses
You have the right to offer no reasons or excuses for your behavior. It’s true.
Now, you might be tempted to give an excuse for your actions or beliefs. But doing so takes the control out of your own hands. Instead, get used to not giving excuses for your beliefs, actions, or decisions.
Don’t get me wrong—you still need to take responsibility if you’re in the wrong. So take ownership and apologize.
But if you’re being pressed to say sorry for something you were in the right for, you do not need to offer up any excuses. And in fact, you shouldn’t do so.
2) Choice
You have the right to decide if you will (or won’t) find solutions to other people’s problems.
You need to learn to say “No” to solving other people’s problems.
You are ultimately responsible for your own psychological well-being, happiness, and success in life. And as much as we might want to do good things for one another, we are not responsible for other people and their problems.
To master this step, you need to get comfortable with saying “no” more often.
So to build this skill up, start saying “no” more. The more you do it, the easier it becomes.
3) Change
You have the right to change your mind.
We don’t have access to all the evidence, all of the time. And when new evidence comes to light, it’s natural—even more, it’s beneficial—to change your mind in light of that new evidence.
This is especially important in a fast-paced business environment like sales. Variables change all the time. And what was a given about a deal or a lead will often flip, turning the knowns on their head.
If you are rigid in your responses to these changes, you can’t react as well as you should. And that can lead to blown contracts, angry prospects, and poor performance overall.
So don’t be afraid to change your mind. Your buyer might even respect you more for it.
Alright so step four of the framework is…
4) Mistakes
You have the right to make mistakes.
No one is perfect. And no matter how smart, skilled, and charismatic you may be, you’re going to make mistakes.
It’s important to remember, though, that everyone else is in the same boat. We all make mistakes. And since everyone does, you shouldn’t have to feel like you need to hide them.
It is your assertive right to make those mistakes and not to tear yourself down (or let someone else tear you down) because of them.
You are not uniquely terrible or especially flawed if you screw up.
And in fact, making mistakes is often the only way you learn. So if you aren’t making mistakes, you aren’t trying hard enough to grow.
5) “I Don’t Know”
You have the right to say, “I do not know” without embarrassment. This one is huge for salespeople. Especially salespeople that work with a particularly technical product or service.
Despite what many in the public think, sales isn’t about bullshitting. It’s not about trickery or cons. Instead, it’s about problem-solving. And if you’re not providing the right information, your solution won’t fix the issue your buyer’s trying to solve, leading to low satisfaction, damaged trust, and zero loyalty (this is bad stuff).
Rather than rattling off a white lie, it’s actually better to say you don’t know the answer to a question.
If it’s a specific product detail, don’t fudge the numbers. Instead, say, “I don’t know” and then assure them you’ll find out the answer.
If it’s an unrelated question, don’t be afraid to say, “I don’t know” and then shutting up.
But just because a prospect asked a question doesn’t mean you need to have the answer, especially if the question was downright stupid to begin with.
6) “I Don’t Care”
You also have the right to say, “I don’t care.”
Your needs, goals, and interests are your own. And just because someone else is worried about an issue doesn’t mean you have to be too.
You tend to find this in the workplace a lot. Random people will tell you how you can become more efficient, or you can become more of a team player, for example. But when it comes down to it, your sales target is based on your actions and work alone.
You should not be forced to care about the stresses, accomplishments, or methodologies of others.
If you’re missing out on some real benefits from collaboration, then that’s on you. But if it’s all about feigning interest for the sake of “harmony,” you shouldn’t feel obligated to care.
Now it’s time to put the framework into action. It’ll take a bit of work to make the shift, I know. But when you do, you’ll find yourself becoming more confident, more effective, and more successful as a sales professional in no time.

May 18, 2022 • 12min
INSTANT Rapport WITHOUT Being Weird | Selling Made Simple
There’s a lot of bullshit in old school sales training. Mirroring body language, fake-as-hell urgency, uncomfortably high enthusiasm—this is what they USED to say closed deals. But in modern times, They’re all crap. They simply don’t work. And they’re scaring off your potential buyers.
Instead, there are a few surprisingly simple ways you can instantly build rapport WITHOUT coming off as a weirdo. And that’s what we’re talking about in today’s video.
Now, before we jump in, let’s talk about the current state of sales. These days, more than ever, your time winning over a buyer is limited. With all the automation in marketing these days, most buyers can get the majority of the info they need from your website or your content funnels.
Added to that, most businesses are facing 3X as much competition as they would’ve been just 15 years ago.
So when you DO get a buyer on the phone, you’ve got to make your time count. Because if you don’t they’ll have plenty of other options to go with. And that’s where rapport comes in.
What Rapport Is & Why It’s Important
Essentially, rapport is how much your buyer trusts you. It’s what dictates whether or not they take your advice, listen to what you have to say, and ultimately choose to do business with you.
And like most ideas in sales, rapport comes down to a very human, very biological issue—are you part of their tribe or not? Are you on the same side or opposite ones?
See, the human brain is wired to keep us close to those we identify with (our tribe) and be skeptical of those we don’t (not our tribe). It’s called in-group/out-group thinking. And it’s this tendency that’s at the root of so many social and political problems today.
But to bring it back to sales, the better you are at building rapport, the more your buyer will think of you as part of their tribe. And that makes it 10X easier to close the sale.
How to Build Rapid Trust
How do you build rapid trust with potential buyers?
With such little time available to you, how can you earn the trust of a buyer quickly?
Well, technique number one is…
A) Great First Impressions
Nailing a great first impression.
First impressions set the foundation for the rest of your conversation. And for video calls, there are four ways to create a great first impression. First…
B) Tidy Up Your Appearance
Tidy up your appearance. No one likes working with a slob. And no one trusts one with a deal worth tens of thousands of dollars either. So spend some time looking sharp. But skip the diamond-encrusted jewelry here everyone. The goal is to hit a look that hints at success but doesn’t overdo it.
C) Upgrade Your Camera
Upgrade your camera. We’re already deep into the age of remote selling. So if your camera’s grainy, shell out the extra hundred bucks or so for a quality camera. Doing so will also make it easier to form a real, human connection.
D) Set the Stage
Set the stage. Make sure you have adequate lighting and a professional background here. That might mean moving the call to a more secluded area if you’re at home. Or maybe even getting a background screen you could pull down during calls.
Now, on the phone, things are a little different. Instead of visuals, we’re talking audio. So to nail your first impression over the phone, first…
E) Smile
Smile when you’re talking. No kidding here. Try it. People on the other end can tell when you’re smiling. And this tiny change can make a huge impact on whether your buyer decides to keep listening.
F) Speak Confidently
Speak confidently and assertively. If you’re worried you’re wasting a prospect’s time, they’re going to hear it in your voice. Instead, remember that you’re delivering real value here. Say your piece with confidence. And make sure your voice is loud (but not too loud) and clear as crystal.
G) Get to the Point
Get to the point. Your prospect’s time is limited. And the more you waste it with fluff and chit-chat, the more they’re going to resent you for it. Simple as that.
2. Drawing Them In
Drawing them in with a very biological, very human way of building trust. What is that you ask?
Making Eye Contact
Eye contact tells your prospect you’re listening. You’re engaged. And you’re ready to help.
In fact, we’re so biologically attuned to the importance of eye contact that we can tell when eye contact is just a little bit off. Have you ever noticed someone looking at your hair or ears? That’s just inches away, and yet, you can tell!
If you’re uncomfortable making so much eye contact, try looking between the person’s eyes. That’s close enough that they won’t be able to notice.
Now for phone calls, that’s a bit harder. So instead…
Make Ear Contact
Make ear contact. Let the prospect know you’re paying attention by listening more than talking. In fact, the top sales reps spend more time listening than they do talking. You should also regularly repeat your prospect’s concerns with phrases like, “So what I’m hearing you say is…” or “It sounds like you’re saying the problem is…”
This helps keep communication clear while also signaling, “Hey, I’m listening to your every word.”
3. Finding Common Ground
Finding common ground. As soon as you start speaking, find something of common interest.
A great place to start here is contacts, colleagues, or referral sources you have in common. This is without a doubt the most powerful social proof you have. And dropping a familiar name alone is often enough to keep them on the line.
If you don’t have any common contacts, it’s time to do your research. Look for any content they’ve put out on their socials, any industry news they’ve read or commented on. What you’re looking for here is leverage. What’s going to perk up their ears and get them saying, “Oh right, I know what he’s talking about.”
It’s the foot in the door you need to keep moving on.
4. Finding Common Ground on Steroids
Finding common ground on steroids. And that means finding a similar goal.
Sure they’re a buyer and you’re working in sales—different businesses, right? But you’re also people. And that means you two likely have similar goals.
USE THAT.
Early retirement, building enough financial freedom to focus on hobbies, sending your kids to a great school—these are all goals you can both relate to.
And when you find these goals, you’re not only creating a deeper human connection. You’re also setting the groundwork for pain points to hit during your pitch.
That’s a win-win!
And when you use these four techniques together, you’re going to turn into a rapport-building machine.

May 16, 2022 • 14min
No One Buy’s From This Type of Sales Person | Selling Made Simple
Nobody wants to buy from a people pleaser. it’s a business killer.
Now, we all want to make other people happy. We’re social animals. And caring about the opinions of others is hardwired into our brain. It’s in our DNA.
But when you make the happiness of others your primary goal, it can lead to some pretty disastrous consequences. And that goes double, triple, and quadruple for sales reps like you.
So, how do you stop being a people pleaser?
5 Problems
5 problems with people pleasing. Why is being a people pleaser such a bad thing in sales anyway? Well first off, it leads to…
1) Wasted Time with Bad Clients
Wasted time with bad clients. People pleasers hate confrontation. And that can make it difficult, if not impossible, to cut bad clients loose early on.
The result? Tons of wasted time. Tons of wasted effort. And a buyer that sucks all the value out of you possible and then leaves you high and dry.
2) Great Relationships Are Built on Equal Value
Great relationships are built on equal value. People pleasers are notorious for being taken advantage of. And that sets the foundation for a wholly unequal relationship. When equal value isn’t brought to the table because of what’s known as covert contracts (more on that in a sec), a buyer won’t think twice about ditching on a deal at the last minute.
3) Finding the WRONG Solution
Finding the wrong solution. People pleasers are bad communicators. And as sales reps, it’s our job to connect the right buyers with the right solutions. But since a people pleaser’s so avoidant to conflict, they may end up misleading the wrong buyer to believe the solution can fix their problem rather than risk disappointing them.
And that, as you can imagine, can lead to some very serious problems.
4) Inauthenticity Breeds Contempt
Inauthenticity breeds contempt. Nobody likes a suck-up. And more importantly in sales, nobody trusts a suck-up. When you can tell someone isn’t acting authentically, the promises they make, the guarantees, the assurances—they don’t mean a thing.
And that’s enough to leave buyers heading for the hills.
5) Your Boundaries Will Suffer
Your boundaries will suffer. Perhaps the biggest problem with being a people pleaser is that others won’t respect your boundaries. You’ll tell them you need to be out of the office by 5. Yet, they’ll still ask you to stay late to help them finish up their work. And being the people pleaser you are, you’ll agree.
The problem here is your own needs will suffer. And that means you’ll be way more likely to burn out sooner.
So, how do you stop being a people pleaser?
The How to Stop People Pleasing Framework.
The How to Stop People Pleasing Framework. This framework has just three simple rules. Yep, three. That’s it. And the first one is perhaps the most important.
A) Prioritize Needs
If you don’t make your needs a priority, someone else will inevitably come along and take advantage of you. That’s just a fact. And it’s just how we’re wired.
That’s why the number one rule of the framework is to take stock of your needs and start prioritizing them.
After all, if you’re not in a good place, you won’t be able to help others as effectively.
It’s like in those airline safety videos—“Always put on your own mask before helping others during an emergency.”
But to do that, it helps to understand one of the most nefarious aspects of being a people pleaser—covert contracts.
Covert Contracts
Covert contracts are unconscious, unspoken agreements that people pleasers use to interact with everyone around them.
A people pleaser’s covert contract might look like this:
“I will do X for you, so that you will do Y for me. But I’m not going to tell you what the contract consists of. Instead, I’m going to hope that you understand what I want and I’ll get mad if you don’t deliver on it.”
The problem of course is that the contract isn’t agreed upon by both parties. And as a result, a people pleaser will often put in tons of effort only to be snubbed when it comes time to sign on.
The challenge, then, is to uncover these covert contracts and take responsibility for getting your own needs met. If you want an exchange in value, you need to be overt about this, especially to a would-be customer.
Remember, this is a business transaction, not a personal relationship. You have to understand that having your needs met in business is a part of the game. And being an adult means making your own needs a priority.
B) Shift Validation
Shift your validation. See, other people are terrible judges of the value of your own work.
They have their own lives to worry about. Their goals, their ambitions, and their endless thoughts and emotions are filling their heads every hour of the day. So if they don’t hand out the validation you’re looking for, it may not be because you aren’t worthy of it. But rather, it’s because they’re just concentrated on themselves.
If you truly want to be successful, you need to only care about how you judge yourself.
When you depend too much on others to build up your own self-worth, you’re at their mercy. You have no control over your life. And the goals you set, the dreams you have for what you can accomplish, those are all going to be under the power of someone else.
The result for you is feeling exhausted, anxious, and unfulfilled.
Worst of all, you’ll have zero control over your life and where you want to take it.
But when you shift your validation standards away from others and towards yourself, you’ll have the freedom to make decisions for yourself. And there’s nothing more empowering than that.
C) Power Words
The two most powerful words you can use in sales.
Can you guess what they are?
“Yes” and “no.”
Unclear instructions lead to uncertain results. And if you’re not clear when you say “yes” or “no” to people, it’s your fault when they pester you to do something that you don’t want to do.
When you learn to wield these two power words effectively, they’re going to help you set boundaries. Boundaries that you should never, ever waver from. And once those boundaries are set, you’re going to find yourself with more time and more energy on your hands.
Now, you should also practice eliminating the word “maybe” from your vocabulary.
Outside of job commitments, if something isn’t a “hell yeah” then it should be a no. Plain and simple. When you approach situations with this mindset, you can start weeding the low-value activities from your life and start concentrating on those that are high-impact. Like creating insightful content, filling up your buyer pipeline, and expanding your skillset.
So kill the maybes and stick to the absolutes instead.

May 13, 2022 • 13min
The Pros & Cons of Working in Sales—The TRUTH | Selling Made Simple
There are few professions that match the high risk, high reward stakes of sales. For some, this is the best way to earning true financial freedom. But for others, it’s never going to be that perfect fit.
Today we’re talking about the real pros and cons of working in sales. The euphoric ups, the devastating downs, and everything in between. So if you’re thinking about joining the sales industry or just wondering if this is your right profession, this is the guide for you.
Now, let’s face it—not everyone’s cut out for sales.
Ambition, confidence, self-discipline, and not to mention plenty of grit—they’re all required if you want to make it in this industry. And even if you do have all the right qualities, long hours, difficult quotas, and a high-stress environment are typically a given.
But few other professions carry the enormous benefits of killing it in sales. And if you’re the right type of person, no other career will give you the same fulfillment and control over your on-the-job success.
The trick is knowing what to expect in this job beforehand. That way, you can make an informed decision about if this is the right job for you.
And that’s what I’m here for. Today we’re looking at the true upsides and downsides of being a sales pro. No lies and half-truths. No BS. And no holds barred.
So first off, let’s start with the pros of working in sales.
By far one of the biggest benefits is…
Pro: It’s the Quickest Way to Become a Millionaire
The money. Yep, sales can be lucrative. Incredibly lucrative if you’ve got the talent.
And when you do have that talent and, of course, a proven sales system, hitting your quotas and raking in massive commissions isn’t all that difficult.
As author and business founder Kent Billingsley told me in our interview:
“Sales is one of the professions where you can make an embarrassing amount of money and have so little responsibility.”
See, with traditional professions, your salary is capped. Sure, you may get bonuses and raises every few years. But no matter how hard you work, your end-of-year pay doesn’t change much.
But with the commissions in sales, your earning potential is unlimited. And best of all, your pay is based on your own abilities. So you are in control here, not your employer.
And that’s incredibly empowering.
Pro: Much Less Risk Than Starting a Business
It’s much less risky than starting a business yourself.
Entrepreneurship can be exciting. But it’s also risky.
About 20% of new businesses fail during their first two years. 45% go under in less than five years. And just 35% of all businesses survive past ten years.
You may make it past that point. But realistically speaking, the odds are against you.
When you work in sales, however, there are two threats to your livelihood—getting fired or your employer going under. And both are far less likely to occur than a startup failing.
Pro: Easier to Land Clients Than Going Solo
It’s easier to bring on new clients compared to if you were running your own business.
When you start your own business, you’re starting from ground zero. You’ve got to prove to potential clients that you’re worth trusting. And only then will they entertain the idea of buying from you. That can end up taking years or even decades to do.
But if you’re in a sales position at another company, you can “borrow trust” from your organization. You are a representative of a business with a proven track record, a history of clients served, and a reputation of its own.
Your own trustworthiness will impact your performance, of course. But it’s ten times easier to close if you’re working for an established brand than if you tried going it alone.
Now, the final benefit we’re talking about today is…
Pro: Job Security (If You’re Good)
Job security… if you know what you’re doing.
If you’ve got the skills, you can rest easy knowing you’ll always be employable.
Businesses are in dire need of capable sales reps these days. And while new technologies are threatening other professions, buyers will always want to speak with a real person before spending tens of thousands of dollars.
Even if you do lose your position, you’ll always be able to quickly find a new one.
You just need to make sure you’ve developed the skills necessary to make yourself marketable. Skills like those taught in the Selling Made Simple Academy.
Alright, so now that we’ve tackled the perks, let’s look at the difficulties. Now quick heads up, we’re only going to look at a few downsides here. But these negatives can be absolute dealbreakers for certain types of people.
So with that, downside number one is…
Con: You Have to Learn to Live With Rejection
You have to learn to live with rejection.
Rejection, sadly, is a given in sales. It just is.
So if you’re someone who can’t handle rejection or lets it get under your skin, sales might not be the job for you.
But you also have to be able to learn from that rejection.
Speaker, author, mentor, and sales legend Harvey J Eisenstadt put it best when he told me:
“First, nobody, and I've met thousands of wonderful salespeople in my career, nobody has a hundred percent closing ratio. The second is, rejection is part of the learning process. If you fail to make a sale, what you’ve got to do is go back to your office, sit down by your desk, analyze the sales call, and don’t say, “Why didn't the prospect buy from me?” What you’ve got to say is, “How could I have gotten the prospect to say yes?” Too many salespeople put the blame on the prospect and not on themselves. And they fail to learn from their rejection.”
In this career, you’ve got to be constantly looking for ways to grow, ways to improve, and ways to get better.
And if you can’t look at a failure and learn from it, you’ll never make it in this business.
Con: Things Get Competitive at the Middle/Bottom of the Hierarchy
Things get very competitive at the middle and bottom of the sales job hierarchy.
If you’re just starting out or can’t seem to land a position with the right company, you’ll be stuck working your butt off.
At the bottom of the hierarchy, you’ll be selling commodities. If you move up to the middle, you’ll be working with better products that you actually find useful. But there’s a tradeoff here—those useful products typically come with lots of competition. And it’s going to be tough to close when buyers can find a similar product for less of an investment.
But when you get to the top of that hierarchy—I’m talking medical devices, $100k+ software, etc.—that’s when you’ve reached the sweet spot. These are the products that change the lives of the people that buy. They’re the ones that revolutionize businesses. And they’re the ones that are more interesting, lucrative, and fulfilling to sell.
So the point here is this—you may have to spend some time working your way up in the industry. Or at least finding ways to make yourself marketable so that these higher-tier organizations want to work with you.
And you can do that by developing your skills, expanding your social network, and earning credentials that show you’ve got the right stuff.

May 11, 2022 • 17min
Upselling: Your Ticket to 67% MORE Revenue | Selling Made Simple
Sales manager pushing you for more cold outreach to hit your quota? Not so fast. If you really want to start killing it, you need to shift away from new clients. And towards the ones you have now with upselling.
In fact, done right, upselling your current customers can on average increase your sales revenue by 67%!
That’s the difference between Pirus and Porsche at the end of the year when you take home your commission bonus.
unanswered emails. And eventually, eventually, all that effort could lead to a new buyer or two. Emphasis on the “could” here. Even still, you’ve got to wade through a lot of crap to get there.
But filling your pipeline with new buyers isn’t the only way to do business. In fact, focusing on maximizing value with your existing clients can make your life a hell of a lot easier.
And today, we’re talking about using upselling to do just that.
Sound good? Then let’s do it.
Why Upsell?
Why should upsell in the first place? You’ve already clinched the deal. So what’s the point of pushing things even further? Well, there are four benefits in particular here…
1. It’s Easier
It’s easier than focusing on new buyers. With new buyers, you’ve got to go through the pains of establishing trust. But with existing ones (or those who have already committed to the sale), that trust is already there.
Here’s a stat to prove my point. According to Marketing Metrics, you have just a 5 to 20% probability of successfully selling to a new prospect in most industries. 5 to 20%. If you’re selling to an existing customer though, that probability jumps to 60 to 70%. That’s an enormous increase!
So if you want to make your job selling easier, go with the existing customers. Next…
2. It Drives More Revenue
It drives more revenue. Customers spend more with the brands they’ve bought from before. To put a number on it, repeat customers spend 67% more on purchases than new customers. That’s two-thirds more!
Just think what a 67% increase in earned revenue would mean for your commissions.
3. It Instills Greater Loyalty
Upselling also instills greater loyalty. When you’ve already proven you can deliver real value, your past customers are 10X more likely to continue buying from you. After all, why go through all the hassle of finding a new vendor when you’ve already shown you’ve got the right stuff?
Now, there are clearly some very real benefits to upselling. But how do you do it? That’s where…
The Proven Product Upselling Framework
The Proven Product Upselling Framework comes in. This framework is exactly what I teach in the Selling Made Simple Academy. And it’s made up of four steps. I go into these steps in great detail inside the academy. But for today’s video, let’s go through a quick overview of each step so you can start upselling right away.
1. Document Results
Step one, gather the numbers. If you want to show a current customer that a new product has value, you’ve got to have the numbers to back it up.
When it comes to new vs. current accounts, it’s all about how you treat the status quo.
For instance, with new accounts, you want to attack the status quo. Productivity could be better. Efficiency could be better. Bottom-line earnings could be better.
But with current accounts, you’re actually attacking and defending the status quo. You’re defending it because you don’t want clients to head to your competitor. And you’re attacking it so you can convince them to upgrade to your premium product.
There are a couple of ways you can do both at once. But the best I’ve found is by sending them a value-rich quarterly report.
Now, you can check out an example of this quarterly report in the blog post found in the description of this video.
But in this report, you should include the following:
1. Your Earned Results
Your earned results.
2. Review of Previous Buying Process
A quick review of the previous buying process that reconfirms the client did their due diligence choosing you.
3. Sharing of New Industry Insights
Sharing of new industry insights to provide extra value.
4. Detailed Competitor Improvements
Detailed competitor improvements, highlighting new changes in your industry competitors.
5. Your Own Detailed Improvements
Your own detailed improvements, including new features you’ve been developing and how they compare to your competitor’s.
6. howing the Cost of Change
A section summarizing the cost of changing considering everything discussed so far. This is also a great place to start introducing your upsell products.
2. Review Changing Needs
Highlighting their changing needs. Every business grows. And as it does, needs change. It’s a part of life.
But your job is to identify those changing needs and show how your upsell product addresses those needs.
It’s time to put your research skills to work here. As the more nuanced and specific you can get, the better. If you can pinpoint some of the biggest pain points and growth opportunities your client is facing, you can leverage them to better sell your premium product.
Using “what if” scenarios here is a great sales tactic. Try getting them to vividly imagine what it would be like if they achieved their future goals using your product.
Beyond simply priming them for a “yes” answer, this technique also helps the client clearly see that something is needed to achieve those goals. And if you’ve done your job, they’ll know it’s what you’re offering.
3. Share The Risk Of No Change
Three, driving urgency. And the best way to do that is by demonstrating the risk of not switching.
Now, there are six types of risk you can leverage here. First is…
1. Physical
Physical risk. This includes dangers to your buildings, equipment, and people.
2. Strategic
Second, strategic risk. This risk type involves roadblocks to achieving organizational goals.
3. Regulatory
Third, regulatory risk. Have their compliance risks changed? How can your product reduce this new risk?
4. Operational
Next up is operational risk. Can your product reduce the new risks that now exist in the buyer’s operations that didn’t exist before?
5. Technological
Then there’s technological risk. If your buyer has increased their reliance on technology, can you reduce their new risks with your product?
6. Financial
And of course, financial risk. If your buyer has increased in size, production, or headcount since you originally sold them, has their financial risk increased? Can your product help reduce this financial risk?
Try to point out multiple types of risks your buyer faces during your upsell conversation. Two or three should get the ball rolling.
4. Instant Discount
The “coup de gras” a.k.a. the killing blow. So you’ve proven your worth with a quarterly report. You’ve highlighted the buyer’s changing needs. And you’ve outlined the risks of not changing.
What’s the trick to pushing the buyer over the edge? To finally getting that elusive “yes”?
The instant discount.
Now, this doesn’t have to only be a price discount. It can also be complimentary onboarding support, expert consultations, additional product add-ons—whatever. Get creative here.
But essentially you want to create a time-based trigger event that gets them to act now.
There are a few things you can do to ensure that trigger event is effective.
1. Avoid Fake Urgency & Scarcity
Avoid fake urgency and scarcity here. These ploys, when uncovered, only breed animosity and degrade your client’s loyalty (a death sentence for your rapport).
2. Don’t Get Too Flashy
Don’t get too flashy. Too many buzzwords and urgency pushes will rub buyers the wrong way. Instead, be clear, confident, and respectful. Remember, you’re offering value, not trying to meet a quota.
3. Personalize If You Can
Personalize if you can. If you’re only cutting a deal or giving a unique discount with them, let them know. And tie back the deal (for example, lower price) to the client’s goals (like coming in on budget).
4. Keep the Pressure On (To an Extent)
Lastly, keep the pressure on, to an extent that is. There’s nothing wrong with sending a few helpful reminders that your trigger event is ending soon. Just be careful of getting too pushy here.
With the right trigger event, your buyer won’t have any other choice but to say yes to your premium upsell.