From Awkward Pitches to Natural Conversations: The Entrepreneur's Sales Evolution

An organic pest control salesman knocked on my door last week, working the neighborhood. I hadn't heard of his company, but he was engaging enough that I let him deliver his pitch. Having sold books door-to-door one college summer 30 years ago—and spending a lifetime in sales since—I had empathy for his situation and curiosity about his approach.

It didn't take long before I could predict exactly what he'd say next.

After he left (without a sale), I realized his techniques were nearly identical to what I'd learned three decades ago. Has nothing changed in sales training?

The Time Warp Problem

When I was recruited on campus with promises to "earn more money in a summer than you do in a year," I received a week of immersive sales training. Scripts, role-playing, door positioning techniques—all the methods I was witnessing with this young salesman.

This isn't about him personally. If I were hiring salespeople, I would have recruited him on the spot. This is about the outdated training he received and the absurdity that in five minutes, I was transported back to Sales 101 from the 1990s.

Here's the thing: this interaction represents exactly why so many business owners say they "hate sales" while being their company's primary business developer. What creates resistance in sales is often a bad memory of experiences like mine—when the opposite approach is what makes sales a true service.

The Techniques That Never Die (And Why They Shouldn't)

These components work. There's a reason they're still taught decades later. The difference lies in the approach—the customization and adaptation that feels authentic, reduces tension, and builds genuine relationships.

Let me break down what felt familiar about my recent exchange and how these classic steps can be refined for better results:

1. The Approach: Making First Contact

The old way: Ring the bell, take two steps back, turn sideways to appear non-threatening.

The modern adaptation: In business, this translates to doing your homework. Research prospects beyond surface level to uncover genuine common ground. LinkedIn stalking isn't rapport building—finding authentic connection points is.

2. Establishing Credibility

The old way: "I've been helping people in your neighborhood"—name-drop streets and neighbors.

The modern approach: Reference genuine referrals, remind prospects where you met, or mention your specialization in their industry. It's not name-dropping when it's relevant context.

3. Positioning Against Competition

The old way: Ask what they're currently using, then explain why you're better.

The smart way: My pest control guy actually nailed this. Ask what they like about their current solution AND what gaps remain. Don't criticize their choices—focus on how you're different or how you enhance what they're already doing.

4. Identifying Decision Makers

The cringe way: "I imagine in your household you're the CFO, am I right?"

I literally laughed out loud. This isn't 1950s vacuum sales, people. While you absolutely need to understand decision-making dynamics, please skip the cheesy empowerment attempts.

5. Creating Urgency

The approach: "We bundle neighborhood pricing" and "Today I'm offering a discount."

The reality: If they don't want it, urgency doesn't matter. If they're intrigued, it helps. Know your audience—does your timeline align with their decision-making process? For transactional businesses, "today only" makes sense. For relationship-based sales, it feels pushy.

6. Gauging Interest

The key insight: Sometimes it's not objections—it's apathy.

My pest control guy was skilled at handling objections, but my interest level was simply low. In these situations, pivot. What DO they care about? Maybe you're solving the wrong problem right now. Find their pressing issue, and the entire conversation shifts.

Pro tip: Even if you can't solve their urgent problem directly, you probably know someone who can. Making that referral builds relationships regardless of immediate sales.

7. The Close

The tired line: "What would make you say yes today?"

The better approach: Know your sales process and natural next steps. Stop trying to force everything into one conversation.

• Outreach gets meetings
• Discovery uncovers potential
• Presentation narrows options
• Proposals offer customized solutions
• Agreement includes next steps
• Execution deepens relationships and reveals new opportunities

Break it down. Take a breath. Enjoy the process.

The Missed Opportunity

Here's what really frustrated me: I was actually a perfect target prospect. But my salesman never asked if I had problems he could solve.

If he'd simply asked, "What bugs you about the creatures in your yard?" (I would have appreciated the pun), I could have listed several irritating issues. That would have opened the door for him to explain how they address those specific problems.

Instead, he just told me what they spray for. I didn't care.

The Bottom Line

Sales is service, regardless of what you're offering. The techniques work when they feel authentic and focus on genuine problem-solving rather than manipulation.

Stop using scripts from the Clinton administration. Start building real relationships that solve real problems.

Your prospects—and your revenue—will thank you.

Experiences like these led me to creating something special for entrepreneurs who aren't classically trained sales people, AND are the revenue generators of their business. 

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