The Discipline of Sales: When Confidence Becomes Your Biggest Enemy

Sales is often about confidence—knowing your product, knowing your client, and knowing the value you bring. But there’s a fine line between confidence and overconfidence. When you feel the sale is a "sure thing," it's easy to let your guard down and skip the critical steps that ensure success. The truth is, the deals that seem easiest are often the ones that fall apart the fastest if you don’t follow the discipline of sales. And that discipline starts with asking one crucial question: Why?

When in Doubt – Ask 'Why'

In any sales process, when things seem unclear or uncertain, asking 'why' is your greatest tool. It gets to the heart of the issue, helping you understand not just what your prospect needs but the reasons behind those needs. Asking 'why' can reveal deeper pain points, uncover underlying motivations, and expose potential challenges.

For example, let’s say you’re meeting with a prospect who says their biggest challenge is growing their customer base. Instead of jumping straight into offering a solution, start by asking 'why'. Why are they struggling with customer growth? Why have previous efforts not worked? This approach not only helps you gain a clearer picture but also builds trust by showing that you care about their specific situation.

When Confident – Ask 'Why'

Ironically, the time to ask 'why' is not just when you have doubts. It's equally important when you feel completely confident about a sale. Overconfidence can lead to missing key details, and as a result, losing the deal altogether.

Imagine sitting across from a business owner with a $10 million company. They tell you they are stuck and struggling with sales, and you know you have the perfect solution. You're confident, but in that confidence, you skip asking crucial questions. You jump into your plan: Get back to the basics, revisit the growth model that worked, and focus on key areas like serving the right customers and offering more value.

It sounds solid, right? But suddenly, your prospect shuts down. They’ve lost interest, and you're left wondering what went wrong. What you didn’t ask—what they had already tried—was the most important question. If you had asked, you would have discovered they had hired a consultant who sold them a similar solution, and it failed miserably. They had already been through this exact process, and it didn’t work.

Story Time: The Cost of Overconfidence

I’ve made this mistake before—multiple times. Let me share one of those experiences with you.

I was sitting down with a gentleman who ran a $10 million business. He was frustrated because his company wasn’t growing, and he wasn’t making sales. Everything about the conversation felt like a home run. I knew I could help him. I had the answers.

Confidently, I walked him through the steps: focus on who they best serve, understand their unique value, and refine how they present that to their customers. Simple, effective, and proven. But as I continued, he completely shut off.

What I failed to ask was the simple question: What have you tried before?

If I had asked, I would have learned that he had already hired a consultant who pushed a nearly identical strategy, and the results were disastrous. The consultant had left him skeptical, disappointed, and unwilling to trust another outsider with the same solution. Had I asked 'why,' I could have tailored my approach to address where the previous strategy failed and built trust by understanding his specific situation. But instead, my overconfidence cost me the deal.

Trust is Built Through Understanding

In sales, confidence can help you present your ideas with conviction, but trust is built through understanding. The moment your prospect feels that you’re just like everyone else, offering the same solutions without knowing their unique struggles, the deal is in jeopardy. I lost that deal because I didn’t take the time to understand where the previous effort fell short. Overconfidence killed my ability to develop trust and make the sale.

The Lesson: Stick to the Discipline

The key takeaway is simple: When everything seems to be going smoothly, that's the time to slow down and return to the basics. Stick to the discipline of sales—asking questions, gathering information, and developing a deep understanding of your prospect’s needs. Even when you’re confident in your solution, take a step back and ask the important questions. You never know what you’ll uncover by simply asking why.

At the end of the day, it's not just about knowing what the client needs; it's about knowing why they need it and what hasn’t worked in the past. Sticking to this discipline will help you avoid costly mistakes and lead to better, more successful deals.

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