5 Sales Mistakes Costing You Deals (and How to Fix Them)

Oct 15
3 min read

Updated: Nov 26

A Few High-Quality Tactics to Help You Succeed in Sales

Some of the most valuable lessons I’ve learned didn’t come from success. They came from slip-ups, missed opportunities, and downright funny mishaps.

The five mistakes below are among the most common I’ve observed from consultants and sales professionals across industries. These mistakes are easy to overlook because they often feel like “small things.” I know… I made them myself.

The truth is that awareness of your gaps is a blessing. It gives you the power to grow. Once you can spot the issue, you can fix it. That’s where transformation begins.

Mistake 1: Talking More Than You Listen

The Problem: Many sales professionals rush to explain their product, idea, or service. They are eager to prove value before understanding what truly matters to the person across the table. Unfortunately, this screams “ME! ME! ME!” to your prospect.

The Fix: Slow down. Ask open-ended, thought-provoking questions that evoke feeling and uncover real needs:

“What’s most important to you right now?”
“Why is finding a solution for ____ so important to you?”

Then listen. Pay attention not just to words, but to tone, pacing, and pauses. Often, the truth behind a buyer’s motivations lies beneath the surface.

Mistake 2: Treating Sales as a One-Time Transaction

The Problem: Some approach sales like a quick exchange. "I give, you buy." This misses the bigger picture.

The Fix: Think of sales as a relationship, not a transaction. When you focus on solving problems and building trust, people return, refer you, and see you as a long-term partner.

Mistake 3: Letting Opportunities Slip Through the Cracks

The Problem: Even skilled professionals lose deals when they don’t stay organized. Forgotten follow-ups, missed reminders, and scattered notes lead to lost opportunities.

The Fix: Keep a simple, reliable system. Whether it’s a CRM, a spreadsheet, or calendar reminders, find what works for you. Then, evolve it. As your business grows, create smart systems that work for you rather than you constantly working for them.

Consistency compounds. An organized salesperson with great timing will outperform even the most talented, but disorganized, competitor.

Mistake 4: Talking About Features Instead of Value

The Problem: It’s easy to describe what your product does. “Our software has 10 modules” can easily become a rote pitch. However, it’s crucial to connect it to why that matters. Features don’t create emotional or practical resonance.

The Fix: Translate your offerings into outcomes that matter:

“This system can save you 5 hours a week, freeing up time for strategic work or family.”

That’s what people remember and act on.

Bonus Tip: Tie it to something personal and powerful. We like to think we make decisions logically, but emotion drives action.

Example:

“I’m sorry to hear you missed your son’s game last week. Let’s build a system that operates smoothly and frees up your time so you can not only make it to the next game but be fully present.”

You’re not just selling a product. You’re selling a better version of their life.

Mistake 5: Entering Negotiations Unprepared

The Problem: Too often, professionals “wing it” in high-stakes discussions. They concede too early, accept poor terms, or take rejection personally. This happens not because they lack skill, but because they lack a plan.

The Fix: Before every negotiation, clarify three things:

Your Goals: What outcome do you truly want?
Your Boundaries: What’s non-negotiable? Establish the minimum and maximum of the acceptable terms before engaging.
Your Alternatives: What will you do if you don’t reach an agreement?

The strongest negotiators succeed not by improvisation, but by preparation.

Bonus Tip: Engage your team before big conversations. Rely on diverse expertise so you enter the room backed by insight, not ego. Imagine how much more confidence (and credibility) you’ll project when you show up prepared and supported.

Sales isn’t about perfection; it’s about progress through awareness. By catching these five mistakes early, you create more meaningful connections, more consistent opportunities, and ultimately, more sustainable success.