Mastering Sales Psychology: Insights from Simon Severino

Master Sales Psychology w/ Simon Severino

Welcome back to the Daily Mastermind. George Wright III with your daily dose of inspiration, motivation, and education.  We are joined today by an expert in Sales Strategies, Simon Severino. Welcome to the show, Simon.

Hey, George. Thanks for having me. Hello, everyone.

I don't do a lot of interviews, but I try to find individuals that I know will really bring some phenomenal value for the business owners and CEOs and high achievers that are in our show here. So I'm going to give a little bit of background.

Simon's the CEO of Strategy Sprints. He's done $2 billion in sales for his clients over the last 21 years. But he has an amazing list of templates that people can use in business in order to grow and expand their business. He's an individual that has a top-ranked podcast. He's the author of Strategy Sprints, which I love the word and the term in general, TEDx speaker, Forbes contributor, and triathlete.

You're just an all-around very successful guy.

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Simon's Journey into Sales

So do me a favor, give everybody an idea of what took you into sales. Like, why is that the area that's your genius? What brought you into that originally?

Yeah, it's funny because it was never a goal of mine. When I started working, I was a strategy advisor in a big firm.

And when you're a strategy advisor, you have to land your own clients. So I was always landing my own clients. And I didn't even know that it was for sales. I was just having clients, I was having work, and I had to solve big problems of how to enter the market, stay in the market, and keep market position.

So I was so passionate about doing that, that the next project came in, the next project came in, the next project came. When I went on my own and became an entrepreneur, I realized so many moving parts, but actually, it's marketing, sales, and operations.

And inside of sales, I realized that it's mostly psychology.

It's really understanding the other side, asking really good questions, becoming a masterful listener and interviewer. And that's my passion. I love becoming better at buyer psychology and understanding why people buy what they buy, what's the best buying experience, and designing businesses accordingly, according to that buying experience.

And so I'm really passionate because there is so much to learn about why buyers buy and how buyers buy. And second, there is not so much about it. There is a lot about selling, but there is not so much about buying. And yeah, I did fall in love with the buying question, and I'm still obsessed with that.

I love that. Obviously, like most people that eventually find the area that they're amazing at, they do it in life. They just go through business. And I love the way you put that phrase of the buyer psychology because I do think a lot of people don't understand how significant the sales process is.

Even if you're not the one selling and you're running a business, you've got to understand the significance of that. And the perspective that it's not just about having techniques and strategies to close deals. It's about having an understanding of the psychology of the buyer, of the other person. And a lot of people don't put effort into that.

So I like that you say that, and I know you also have a lot of amazing strategies.

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Effective Sales Strategies

But where does someone start to understand the psychology of the buyer? Where do you recommend people start to begin to understand what the mindset is of their ideal client?

I'll give you a practical example. We get six, seven, eight sales recordings from our clients so that we can give them feedback and increase the win rate.

Now, what do you think makes the biggest difference in a high win rate in the 70% vs a very low win rate in the 10%? - it's the talking time. Talking time below 30% has a 70% win rate. So if you're talking 28% of the time, you are winning the deal 70% of the time.

So what are you doing when you're not talking? You're listening?

Yeah, it turns out the biggest impact is being a good listener, but listening is not enough. You have to ask the right question and then listen.

I love that because we always hear in sales, "Don't talk so much." And so many people with sales presentations are just trying to sell, close, and they don't stop to listen.

But I never thought of tracking the metric of being aware of how much you are talking. So I like that a lot. But at what point, how do you become effective at asking the right questions? How do you become effective at really becoming strategic with your talk time?

So with all our clients, we help them develop their own sales script, which means 48 stages of closing the deal.

There are eight very specific stages for closing big deals. In each stage, they have three powerful questions that are relevant to their buyers and that they feel good asking because they show their expertise. So for example, if they say, "Yeah, but it's not the right time." Now you might have different ways of answering that, but if you ask the right question right now, they will see, "Oh my God, he's really intimately into my world."

He knows exactly where I am and why it's not the right time. And you ask the question in a way that has them thinking deeper around that, and you give them enough time. Now, you have established a stronger relationship. They feel that you're an expert, that you have intimacy with their world, and the space is a valuable space.

And you don't have anything else. You don't have the product during the conversation. So you have only the conversation itself. So this is where you have to land value to move forward.

I actually really like how you put that—being strategic with your questions as well. You want to ask questions that are relevant to the buyer but also that showcase your expertise that allow you to lead the buyer.

How do you shorten the path? Because I think a lot of people in sales try to think of how to shorten the path to get a deal. How do you shorten the path? What is the way to do that?

We have to be backward-engineers. If you think about someone working with you for six months, what is the transformation? What changes in their life, in their business? Now we go back to the first week of working with you. How can we have them experience a small sample of that in the first seven days? In the first four hours?

And now we go into the sales conversation—the first 40 minutes. Because you only have that conversation; otherwise, they will not move forward. So you have to have a sample of that. And the best way to sample that is not through presentations; it's by asking the right questions. You will have some samples of your right questions.

For example, if your product is a CRM, you will ask how they follow up with leads right now. And then you'll ask, "What do you do if you forget to follow up?"

And they'll say, "Oh my God, how do you know that I frequently forget to follow up?"

By doing that, you're creating a moment that will happen three months later when they use the CRM and don't forget to follow up. But they will experience a sample of that right now. They’ll see the broken flow, the right flow, and they will experience the difference.

I love it. I love it. One of the things in sales that I think people don’t understand—and your book is packed with this—is that people are really looking for roadmaps and paths to succeed. Asking better questions, understanding the psychology of your client, and ultimately, people just want to accelerate their sales.

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Accelerating Business Growth

The whole idea behind your book—I wanted you to maybe take a minute and dig in a little bit to the “12 Ways to Accelerate Growth.” That’s what people want. They want to accelerate growth. And you have so many different things. I’m going to highly recommend that people listening to this check out the book because it’s packed with strategies and tactics. But what are some accelerated growth strategies that fit most businesses right now?

In the book, we outline the three levers for doubling revenue in 90 days. This is the Strategy Sprints method:

1. Increase the price by 25% for the same offer without losing clients. You do that by improving positioning.
2. Improve the win rate by 25%. You achieve this by creating the eight-step playbook and reducing your talk time to 28%. Then, you practice by recording, reviewing your tape, and improving like an athlete.
3. Reduce sales time by 25%, which increases your sales velocity by 25%.

Reducing sales time is tricky. You can tackle it in two ways. First, you shorten the time from awareness to closing by using videos and voice messages in a high-frequency cadence during the first 12 days. We call it the "Relationship Building Sequence." By doing this, you create 12 times the value in the first seven days and shorten the sales cycle by at least 25%.

If that doesn’t work—because you’re dealing with a complex B2B scenario involving multiple stakeholders across departments and countries—we go to the other side of the funnel. Here, the focus shifts to retention, upselling, and cross-selling. Customers come for a solution, but they stay for a community.

When you increase these three metrics by 25%, you effectively increase revenue by 99%.

Wow. I love the simplicity of that. There are so many levers in sales, but those three—pricing, win rate, and sales cycle time—are primary. Do you find that clients struggle the most with the first one, increasing their pricing?

Absolutely. Most people undercharge, and they introduce pricing at the wrong point in the sales conversation. Pricing should only come in step six, but many people mention it in steps one, two, or three.

The second mistake is they over-explain. For example:

"Hey Simon, what’s the price of a sprint?"

"It's $27,000, but you also get XYZ..."

Instead, the correct approach is:

"Hey Simon, what’s the price of a sprint?"

"$27,000."

Then pause for 16 seconds—Obama-style silence.

What’s the purpose of that silence?

It shows you own it. You believe in its worth and its impact. If you try to justify the price, you’re telling the prospect you don’t believe in it yourself.

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Practical Sales Tips and Tools

You’ve packed your book with strategies. For salespeople or business owners trying to improve, what habits do you recommend to make them more productive in sales?

We host a weekly "Sales Booster" group, where entrepreneurs bring their pipeline questions, and we review their sales process. The focus is always on one thing: customer intimacy.

The better you understand your customer’s world, the easier everything becomes. You’ll use their language, empathize with their struggles, and avoid wasting their time with irrelevant questions.

Intimacy builds credibility. If a prospect feels, “This person understands my world,” you’ve gained credibility—and credibility is what gets you from a discovery call to a demo, and then to a closed deal.

I think you nailed it. Most people work too hard trying to build their credibility instead of immersing themselves in their prospect’s world. Credibility comes naturally when you truly understand your audience.

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Final Thoughts and Recommendations

Simon, where should someone start if they want to improve their sales process?

It depends on their learning style. If they learn by reading, they can get Strategy Sprints on Amazon. The book includes real-world examples, tools, and checklists.

If they learn by doing, they can visit strategysprints.com and download free tools to apply immediately. For deeper support, they can book a call to explore working with a sprint coach.

Thank you, Simon. You’ve shared so much valuable insight. To everyone listening: revenue grows with sales. Share this episode to help others benefit from these strategies.

Remember, it’s never too late to start living the life you’re meant to live. We’ll talk with you more tomorrow.

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About Simon Severino:

Simon Severino has created +2B in additional sales for his clients over the last 21 years. As an advisor who became CEO, he had to learn the importance of working ON the business more than IN it. Now, he shares his proven templates with high-ticket entrepreneurs. They reclaim 14 hours per week using the Strategy Sprints™ Method and enjoy sales that soar. Author of "Strategy Sprints", Podcast Host Ranking Top 2,5%, TEDx speaker, Forbes contributor, Triathlete. Has appeared on over 1300 podcasts. When he is not supercharging sales, you'll find him swimming, biking, running and tricking his 3 kids into outdoor activities so they can't escape his annoying shrinky questions.

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Guest Resources:

LinkedIn Page: https://www.linkedin.com/in/simonseverino/

Facebook: https://www.facebook.com/strategysprints/

Instagram: https://www.instagram.com/strategysprints/

Website: https://www.strategysprints.com/

YouTube Channel: https://www.youtube.com/channel/UCnSFgJd0CrsEdQdO21txR2A

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About George Wright III:

George Wright is a Proven, Successful Entrepreneur- and he knows how to inspire entrepreneurs, companies, and individuals to achieve Massive Results. With more than 20 years of Executive Management experience and 25 years of Direct Marketing and Sales experience, George is responsible for starting and building several successful multimillion-dollar companies. He started at a very young age to network and build his experience and knowledge of what it takes to become a driven and well-known entrepreneur. George built a multi-million-dollar seminar business, promoting some of the biggest stars and brands in the world. He has accelerated the success and cash flow in each of his ventures through his network of resources and results driven strategies. George is now dedicated to teaching and sharing his Prosperity Principles and Strategies to every Driven and Passionate Entrepreneur he meets. His mission is to Empower Entrepreneurs Globally to create Massive Change and LIVE their Ultimate Destiny.

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