How to Improve Your Sales Conversations: 3 Simple (But Not Easy) Mindset Shifts

You're listening to The Jewish Entrepreneur Podcast with Debbie Sassen, Episode 154. 

Welcome to The Jewish Entrepreneur Podcast. I'm your host, Debbie Sassen. I went from being a financial adviser, author and chronic under earner to building my business to six figures as a financial planner and money mindset coach. And then, on to multiple six figures as a fulltime money and business coach. 

I help entrepreneurs create money making businesses and build wealth using sales and money mindset strategies in alignment with authentic Jewish values. Now, let's dive into today's show.

Hello, my friends, and welcome back to the podcast. Today, on the podcast, I am going to talk to you about sales. Sales is one of the fundamental skills that you need to run a successful business.

Lots of people have thoughts about selling. A lot of people do not like selling and they come to me. My goal is to make all of my clients fall in love with selling. I started selling when I was just a little girl. I had a lemonade stand. Selling lemonade to passers-by during a hot summer afternoon was a way to make my clients very, very happy.

And when I was a teenager, I worked in my cousin's electronics store. I sold VCRs. I sold Instamatic cameras. I sold all the things. If you remember Atari games, Pong. I'm talking about the 1970s, so I'm dating myself a little bit. People came into the store to buy, and when I sold electronic goods, electronic devices that were so simplistic relative to what we have today, people left the store happy.

When you approach sales in your business with the mindset “this is how I'm going to make people happy. This is how I'm going to help people get what they want in life and in business,” it will change the way you think about sales.

So today we're going to talk about three mindset shifts that I think are very simple to implement in your business. They might not always be easy, but if you work on changing the way you approach sales and think about sales, I think it really will do your business a ton of good. And then I'm going to give you one practical piece of advice at the end of the podcast. All right, so let's dive in.

Number one: I had someone say to me recently, during a sales conversation as it was, she was interested in joining one of my programs. She did in the end. And if you're listening and you remember our conversation, thank you very much because you inspired this entire podcast. 

She told me on our sales call, “I don't want to be viewed as a life insurance salesperson.” Now, I don't know what it is about insurance salespeople that they have a bad reputation. I usually use a used car salesman instead of life insurance, but I kind of get it. 

Sometimes you get these phone calls over and over and over again by insurance salesmen and they seem to be relentless. They don't let you go. They're kind of fuzz that sticks onto your jacket. It just doesn't go away. But I do think, as a former financial planner, that life insurance is a very valuable way for you to protect your financial assets.

There's a difference between term life insurance and whole life insurance. We're not going into financial planning issues today or life insurance, but especially if you are the parent of children, young children in particular, insurance is a way for you to protect your family, your loved ones from financial devastation. But I digress. 

This beautiful woman did not want to be viewed as a life insurance salesman. So obviously she had a very bad mindset about what it was that a life insurance salesman was trying to do to her. And that approach, that mindset, that view, those thoughts about sales, someone who pushes and pushes and pushes, I can definitely see why you don't want to be a pushy person. 

However, when I go back to what I just said, think about serving somebody a delicious cup of cold lemonade on a hot summer day. It's 95⁰F outside or 32⁰C, they're sweating, and it just tastes so delicious. Whatever it is that you are selling, all of my clients are beautiful, wonderful people.

And if you're listening to this podcast, you are also selling something beautiful that helps to transform people's lives. It could be coaching, which is what I do. Many of my clients are coaches. It could be that you're a copywriter, and the beautiful words that you write, help your clients by the way, to sell whatever it is that they are selling. And then their services are going out into the world. 

Of course, we have to bear in mind that not everybody that you meet is going to want what you're selling. Can you imagine if you're a vegetarian and you go into a hamburger joint and they're like, “No, no, you really have to try this hamburger. And we recommend that you get it medium rare. It's juicy. We add lettuce, we add tomatoes, we add a slice of onion, and it's so delicious. And the bun, it's fresh. The bread is just so squishy. And you know what fresh bread, fresh buns, taste like.”

And you're like, “But I don't eat meat,” but they keep pushing and trying to sell you the hamburger. You have to understand that not everybody is going to want what you are serving. So if you were trying to sell hamburgers to vegetarians, then obviously they're going to feel like you are a used car salesman or a life insurance agent or something like that. 

But there are people in the world who are carnivores and they want your hamburgers. And if you speak to them the right way, and you tell them how succulent and delicious and juicy your hamburgers are, then of course their mouth is going to water. They're going to start salivating, and they're going to want to buy your hamburgers. 

So you always have to understand that you are selling to the people that want what you have, want what you're offering. You don't have to sell your goods and services to 8 billion people in the world. You can't even probably serve them anyway. Even Amazon doesn't serve 8 billion people all at the same time. They serve a lot of people, but they have an entire delivery for us and lots of warehouses and Amazon sellers all over the world.

You just have your people. Today it might be 10 ideal clients. Tomorrow it could be 50 and then 100 and then 1,000, and you're going to scale your business even into the thousands of clients that you'll serve over the lifetime of your business. But just for today, focus on your audience, the people that you are really here to serve.

And my belief is that my clients are divinely contracted to work with me. They come into my world. They come into my audience. They're interested in what I have to offer. And if I don't sell to them, they're going to walk away empty handed. They're going to be disappointed.

I want you to take that mindset shift onto the work you do. When people reach out to you, my firm belief is that 80%, maybe even 90% of the people that get on a sales call with me, they want to work with me. And if I don't manage that sales conversation correctly, they're actually going to be disappointed because they wanted transformation today. They wanted results. They were looking for a solution. 

Can you imagine if you had a problem with your washing machine? Your washing machine was broken and it's not washing your clothes. So then you call the appliance repairman and the appliance repairman doesn't want to sell. He doesn't want to come to your house. He's like, “Well, it's very uncomfortable for me to sell. So maybe you want to call somebody else, because this is a really uncomfortable conversation.” 

You're not going to get your washing machine repaired. You're not going to be able to wash your clothes. And now you're going to have to make another phone call to another person and another person until you find somebody who can actually come and take care of your washing machine. 

I know this is maybe a silly example, but when you want something in your life, you want to change, you want somebody on the other end of the line to be responsive. They might ask you questions. “What happened? Did you get a sock stuck in the pipes or something like that? Is this a new problem? Okay, I'll come over today at three o'clock and I'll fix it.” That's what we want, your people getting in touch with you. 

I really want you to take that to heart; when somebody reaches out to you because they're interested in working with you. It's not somebody who you maybe promised a free audit of their website. You're not going to go and try to sell someone that you promised free advice or free services, or someone who reaches out to you for a free coaching call or a free healing session or a free meditation or something like that. 

Somebody with who you shared that you have free resources, that's not the time to sell to them. You can bring them into your network. You can create this know, like, and trust factor. And at some point in the future, if they stick around and they reach out to you, well then you can sell to them. But in the beginning, you're going to create the relationship.

And when they want, when they come to you, that's when it's okay for you to sell something to them, because they really want to work with you. So that is your mindset shift number one. 

When people reach out to you, selling is serving. We're not pushing. We're not going to be sleazy. We're not going to be that used car salesman selling a lemon. Selling is beautiful. You're giving your people what they want when you allow them to say yes to working with you.

Number two: I know a lot of people open up their businesses and they love the thing that they do. They're a coach... I'm going to use my example... I'm a coach and I love being a coach. I love helping my clients have a transformation, seeing things a different way, helping them with strategies so that they can grow their business. 

So somebody opens a coaching business and they're like, “No, but I just want to coach. I don't want to have to do marketing. I don't want to have to do selling. Can't somebody do this for me? Why do I have to do it?” It's like a cousin to this other thought that we had before, about selling is sleazy. Selling is manipulative, so I don't want to do it. 

But a lot of times it just is a skill set that you didn't learn. You learned how to be a coach. Or let's take someone who's a copywriter. You learned how to write words and put them on paper, put them up on a website. But you haven't yet learned the skills of selling, so you just were like, “Well, maybe somebody else can do this for me.”

Here's what I want to offer you. Perhaps there was a day, back in the day, where you actually worked for somebody else. You were a coach. You worked on somebody else's coaching team or you were a copywriter. You might have worked in-house, in somebody else's business. 

And at that time you were making $22/hour and you were like, “I can't believe this. They're charging the clients $100/hour and I'm only getting paid $22/hour. I could really go out and do this myself, open my own business and make more money.”

A lot of people open their businesses thinking like that. So here's the thing. The CEO of that business where you were working before, they were actually doing the marketing. They were doing the selling. If they had a real office, they were probably paying rent, electricity, water. They were managing the money. They were taking on all the risk onto themselves.

And so everything that they received from their clients, that $100/hour had to be divided among all of the expenses. And of course, the CEO also needs a paycheck. They need to take home money as well, to feed their family. And so, yeah, that's why you ended up with $22/hour in your pocket. 

So when you want to open up your own business, you can't just stay in your comfort zone and do the thing that you do without doing the marketing and selling and money management. It's part of running a business. If you are a CEO and you're owning your own business, you have to have a CEO mindset, not an employee mindset. 

If you're an employee, then somebody else is doing all the business activities and they're taking the risk. Once you have flipped the script and you are now running your own business, you have to act like a business owner, which means you have to sell. Businesses sell. If you don't close the sale, you don't make money. 

Yeah, sometimes people will come to you and say, “I really want to work with you. Here's $1,000. Here's $10,000. Take my money.” And as you grow in your business and you develop a reputation, then you will be the one and only, and people will, or some of them will, reach out to you and just give you their money because you are the only one they want to work with. 

But until you get to that stage where people know you, and lots and lots of people know you, you've got to do the marketing. You've got to do the selling. And even as you continue to get known, you have to keep marketing and keep selling because people forget. You can't just disappear out of their world and hope that they will continue to keep you top of mind. 

Businesses need to be run like proper businesses. You have to have a plan for how much money you want to make in your business in 2025. And then you have to do your marketing. You have to do your sales. You have to manage your money. You have to deal with all of the other business expenses. 

So if you are running your own business… you've decided whether you're going to be a freelancer or you're going to be a small business and have employees working with you… you have to think differently. That is the second mindset shift that you need to make. You have to do things, and you might not love all of the things. 

But hey, even as an employee, I remember doing lots and lots of things that I did not love doing because that's what I did. It was my job. So guess what? You running a business is your job and some of it's not going to be fun. You might have to take out your own trash. There's no cleaning service coming to take the trash out of your office. You might have to deal with your computer issues, your tech issues, and your sales issues.

So the mindset shift is thinking like a CEO, where sales is part of what you do in your business. 

The third mindset shift you need as a salesperson in your business is that you sell as a sacred service, you do not convince. I bring this up because one of my clients this week was talking about convincing her potential client. She brought this word in and I wanted to challenge her on it. And she came back with it a second time. The first time I didn't challenge her on it because the conversation, the coaching conversation, went a different way. But then she brought it up again.

When someone is trying to convince you… Just think about, I can think about my kids. They're trying to convince me that I should let them, when they were younger, stay out late at night beyond their curfew. Or now my older kids convince me that they should have the car, because we just have one car and they borrow it from time to time.

When someone is trying to convince you to do something, it has that energy of doing it against your will. They're trying to bring you over to what they want in a very pressurized… it just feels very aggressive. Not assertive, aggressive way. And so we naturally repel people who try to convince us. 

Even think about it in a marriage. If you were trying to convince your partner to do something, that is automatically going to set up a protective barrier. They're going to be like, “No, you cannot come into my energetic space. I feel your energy. You're trying to push. You're trying to convince me. This feels very uncomfortable.” Are you with me? 

And that same thing can happen in a sales conversation. If you talk and talk and talk and talk and try to convince, convince, convince, your person is going to back off. They're going to create a distance, an energetic difference between you and them. And they might even physically pull away from you. 

Even on Zoom, if you watch their energy, if you're really looking at their body language, you might notice that they pull back from you because they're feeling this force coming at them, this convincing energy.

A sales conversation is always about asking questions, trying to go deeper, and trying to understand what else. What else do they want? Why is what is currently going on in their life not working for them? Why do they think working with you would make a change? What do they want? What's the transformation? 

See, these are all questions that we ask our person. Where do they want to be after you work together? What opens up for them after you've worked together and you've written a copy for their website? What is their dream? What are their goals? How can you work together to develop a strategy? 

Sales conversations are all about you asking questions, way more questions than talking. I want you to think about it like this because this will help you keep a visual in your mind. God created you with two ears and one mouth. Do you know what that means? When you get on a sales conversation, you should be listening two times more than you are talking. 

If you notice that you are talking most of the sales conversation, you're doing it wrong. You should be asking a question and listening. Ask another question and listen again. Just ask someone what else do they want? What else do they want? Why is what's going on now not working? Do they have any fears? What will be different for them? 

Do you notice that you can ask a short question, it's maybe five or six words, and then they can say a paragraph or two paragraphs or three paragraphs. The more questions you ask, the easier it is for you to understand what's really happening in the mind of your client. 

And really think about it as you going into a doctor's office and you're going to share with your doctor everything that's going on. The doctor will ask you what's happening. Do you have a fever? When did it start? You'll be able to tell your story and the doctor listens. Most doctors don't spend a lot of time talking. They're doing their investigation and they're thinking. 

They're processing the information and then they're going to create their diagnosis. They don't spend an entire meeting with you, an entire doctor's visit with you, trying to convince you that you should take this antibiotic. Because they've listened. They have created trust between you and them. 

And you may have been seeing this doctor for a while. You might notice that they're thinking, they're assessing different options in their head, and then they're going to give you their treatment plan. 

That's what I want you to consider when you are having a sales conversation with your client. They will give you all of their symptoms. They will tell you what they want after they work with you, what's their ideal result or solution, and then you're going to present them with your treatment plan.

But again, you are doing mostly listening and just a little bit of talking. That's going to build trust. People love to talk. They want someone to listen to them. They want to be able to share their problems. Listen to your people. Then, after you really understand deeply what's happening, then you can present to them the way that you can work together.

I think the one mistake people make on their sales calls is they make them too short. I advise my clients, and it depends on what kind of business you're in… Sometimes you can make the sales calls shorter if you're a more product-based business.

If you're in a business like I am, coaching or even copywriting or website designing, where you really want to get to the bottom of what's going on with your clients, it might be 30 or 45 or even 60 minutes that you spend on the sales call with your potential client. 

So those are the three mindset shifts. Number one: No pushy used car salesman energy. Number two: Sales are sacred and they're part of your job as a business owner. And number three: No convincing and talking and pushing. Listen way more than you talk. 

The additional practical aspect that I want to bring to this is that you need to do evaluations of your sales calls. Because only by reviewing what happened in your sales call… And if you do your sales calls on Zoom, you can have AI in the background, you can have Fathom… 

That's what I use when I'm on my sales calls. I don't share them. My potential clients can easily see that I'm recording, that I have a transcript that's being recorded in the background. Of course, if your potential client doesn't want it recorded, then you turn off the recording. But this gives you all the words your client said and all the words that you said so you can go back and review.

You can actually see what you've said, or listen over to the sales call, and you can notice, did I get salesy or pushy? Did I talk too much? Did I miss something that my client said and that's where I fumbled the sales call? The evaluation part of the sales conversation is for you, so that you can get better. Your skillset as a salesperson can get better. 

And also, do you know what it does? It allows you to serve all of your future clients so much better. Because the next person who gets on a sales call with you, sales conversation, consult, discovery call, whatever you call them, the next person who wants transformation, who wants a different result from what they have right now, because you have improved your sales skills, you'll be able to help them more quickly.

And then you go back, you analyze your sales call, you do an evaluation, and then you tweak something else. Because none of us are perfect. We all have places that we can improve on our sales calls. And one by one by one, you will improve your skillset as a salesperson. 

Don't think that you're not a good salesperson. Don't think that you can't figure it out, you can't learn it. It's just a skill that you've never learned or that you learned a little bit. You're a little bit rusty. You can improve your sales calls. 

So that's it my friends. Those are the three mindset shifts and one practical application so that you can get better on your sales calls. As I said, these are simple. It really is not rocket science, but it's not easy. You have to commit to positive change in your business.

All right, my friends, thank you so much for tuning in to the Jewish entrepreneur podcast today. I want to let you know that if you are not yet on my email list, you really should sign up. Because, first of all, I share very valuable content once a week, at least, on my email list. But we're now nearing the end of November and I'm going to be having some fun Black Friday sales, and you really want to be there to find out what I'm selling for Black Friday. 

So go to my website, DebbieSassen.com/newsletter and get on my newsletter. I will see you next week on the podcast. Bye-bye, for now.

Thanks for listening to The Jewish Entrepreneur Podcast. If you want to stop underselling and underearning and close more sales, you need to clear the limiting money beliefs that are sabotaging your business growth. 

Head on over to DebbieSassen.com/mindset and download my free Money Mindset Workbook. Uncover and dissolve money blocks, like hundreds of other entrepreneurs who are now building six-, multi-six-, and seven-figure businesses and creating true financial freedom.