Why People Don't Get Deals: A Deep Dive into the Art of Sales

Have you ever wondered why some people seem to effortlessly close deals while others struggle? Why do some sales pitches resonate while others fall flat? If you’ve ever asked yourself these questions, you’re not alone.

I’ve spent the last 20 years in sales, from cold calling early in my career to leading a content-driven sales approach today. Through this journey, I’ve learned what works—and what doesn’t. Today, I want to share the top nine reasons why people don’t get deals. And no, “the price” isn’t one of them. Because, contrary to popular belief, price is rarely the real issue.

Understanding the Sales Process

Mastering sales isn’t just about pitching—it’s about preparation, confidence, and strategy. When you understand the process, sales becomes an accessible and even enjoyable experience. But when you’re underprepared, you’ll either avoid it or struggle through it, which leads to stress and missed opportunities.

Preparation is Key

Your success in sales starts before the conversation even begins. You need to:

• Know your product or service inside out.
• Understand your ideal customer’s needs and pain points.
• Have a clear, structured sales strategy.

Without these, you’re setting yourself up for failure.

Embrace the Challenge

Yes, sales can be tough. But it’s also an opportunity to grow, learn, and improve. The key is to shift your mindset—sales isn’t about forcing a pitch, it’s about helping people find solutions.

Now, let’s break down the nine reasons why people don’t get deals.

The Nine Reasons Why People Don't Get Deals

Over the years, I’ve identified nine common reasons why salespeople struggle to close deals. Each comes with challenges, but also opportunities for improvement.

1. Lack of Preparation

If you’re not prepared, your pitch will feel scattered, and you’ll struggle to answer objections. Customers can sense uncertainty, and if you don’t have a firm grasp on what you’re selling, they won’t trust you.

2. Lack of Confidence

If you don’t believe in what you’re selling, why should your potential customer? Confidence isn’t just about sounding enthusiastic—it’s about delivering your message with conviction and certainty.

3. Not Understanding the Customer’s Needs

Many salespeople focus too much on what they’re offering instead of listening to what the customer actually needs. A great salesperson asks the right questions and frames their offer as a solution.

4. Talking Too Much, Listening Too Little

Sales isn’t about dumping information—it’s about having a conversation. If you talk more than you listen, you’re missing key insights into what the customer truly wants.

5. Failing to Build Trust

Trust is everything in sales. People don’t buy from strangers; they buy from those they trust. If you don’t establish credibility early on, closing a deal becomes much harder.

6. Poor Follow-Up

Many deals are lost simply because of a lack of follow-up. A prospect showing interest isn’t the same as a closed deal. Consistent, thoughtful follow-up can make the difference between a lost opportunity and a sale.

7. Not Handling Objections Effectively

Objections aren’t rejections—they’re buying signals. If someone is asking questions, it means they’re interested but hesitant. A skilled salesperson knows how to address objections calmly and confidently.

8. Selling to the Wrong People

Not everyone is an ideal customer. If you spend time pitching to people who don’t need or can’t afford your product, you’re wasting effort. The key is to target the right audience from the start.

9. No Clear Call to Action

Even if a prospect is interested, they won’t take the next step unless you guide them. Every sales conversation should end with a clear, compelling next step.

A Content-Led Sales Approach

One of the most effective ways I’ve found to improve sales is through a content-led approach. Instead of hard-selling, this method focuses on attracting, engaging, and converting potential customers through valuable content.

Converting in the DMs

One of the most powerful tools in my sales process is direct messaging. But sending a cold pitch isn’t enough—you need to:

• Engage in meaningful conversations.
• Provide value before making an offer.
• Frame your product as the solution to their specific problem.

I’ll be sharing the exact wording I use in my DMs in my upcoming Content Conversion Workshop.

The Three Types of Posts You Need

For a content-led approach to work, you need three types of posts:

1. Educational Content – Establishes credibility and provides value.
2. Inspirational Content – Builds trust and connection with your audience.
3. Promotional Content – Clearly communicates your offer and next steps.

If you’re struggling with sales, shifting to this approach can be a game-changer.

Join My Content Conversion Workshop

If you want to learn how I use content to drive sales and close deals in the DMs, I invite you to check out my Content Conversion Workshop. It’s pre-recorded, so you can go at your own pace, take notes, and implement strategies immediately.

What You'll Learn

• The three types of posts that generate sales.
• My exact DM strategy, including real message examples.
• How to build trust and engage potential clients without being pushy.

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