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The life of a small business owner involves wearing multiple hats, with the sales hat often being the most uncomfortable. Throughout my journey, I’ve discovered that effective selling isn’t about slick pitches.
The thing is, it’s about something more fundamental: understanding the customer’s problem before offering your solution.
The me-me-me trap
When entrepreneurs are new to their ventures, I notice a common pitfall. After defining their offerings and differentiators, they’re eager to talk about their amazing solution. That eagerness translates into sales meetings where they talk endlessly about their solution or themselves.
Here’s the cold truth: 99% of the time, this approach fails because potential clients don’t care about you. They care about themselves, right?
As the saying goes, “You have two ears and one mouth.” You should be listening twice as much as you’re talking. A two-to-one ratio is probably the minimum you should aim for in sales conversations.
Related: How to Craft a Bulletproof Sales Strategy That Will Survive Any Economy
Digging for pain points
Instead of leading with your solution, pull information about what prospects are trying to accomplish. Ask: What are you trying to achieve? Why aren’t you doing that already? What challenges have you faced?
When you pose these questions, real pain points surface. Let’s say a prospect mentions they’re interested in your service: rather than jumping into features, zoom in on why they’re looking. The pain points they share become your ammunition for crafting a tailored pitch.
Some pros I’ve observed use a “prequel” approach – a quick call before the formal meeting just to gather information. During these calls, they’re purely asking questions without selling. By the time the actual meeting arrives, they already know the prospect’s pain points and can address them directly.
The five whys technique
One effective method I use is the “five whys” technique, originally an engineering method for finding root causes. In sales, this means digging deeper by continually asking “why?”
Here’s a real-life scenario: Someone says, “I’m interested in video production.” Rather than jumping to packages you can offer, ask: “Why do you want video production?” They might respond: “I need to reach my customers better.” Then ask: “Why do you need to reach your customers better?” They might say: “Because they don’t understand our full range of services. After you hear that reply, follow up with “Why do you think they’re not finding this information currently?”
This continues until you understand the true objective. Sometimes, you’ll discover that people need a different solution altogether that better addresses their underlying problem.
Related: How to Redefine Sales Success — The Power of ‘Yes’ and ‘No’
Building trust through service
Throughout my entrepreneurial career, my relationship with sales has evolved. While I no longer handle direct sales as I once did, the principles I discovered still shape our company’s approach.
The most valuable lesson I’ve learned is that sales works best when it’s about service rather than transactions. This mindset naturally leads to:
- Finding the actual problems prospects are facing
- Earning people’s trust by understanding their challenges
- Discovering what customers need rather than what I want to sell.
This works across any industry. Whether you’re selling professional services or helping a friend buy a car, understanding true requirements yields better results than pushing what you think they should have.
Learning through trial and error
I didn’t master this mindset overnight. In my early days, when I was selling door-to-door vacuum cleaners and telemarketing services, I learned the hard way: talking more than listening fails.
What pushed me to transform my technique was hitting the wall a few times. I’d ask myself, “Why am I not selling when others around me are?” That’s when I started reflecting on what I was doing wrong. My mentors would say, “AJ, you’re talking too much. Ask them what they’re trying to accomplish.”
At Marketcircle, we’ve applied these principles to our product development. When building Daylite, our CRM tool for small businesses, we learned that understanding customer pain points is essential for creating solutions that truly serve users.
We faced this painful reality firsthand in 2023, when Apple eliminated a mechanism we used for mail integration. Without thoroughly understanding our users’ needs, we chose an approach that customers hated despite months of development. This painful experience reinforced that assumptions – whether in sales or product development – can be costly.
The bottom line
Problem-first selling isn’t just about closing deals – it’s about forming authentic connections. By understanding your prospects’ challenges, you position yourself as a problem-solver and trusted advisor.
The next time you prepare for a sales conversation, remember: your goal isn’t to explain your solution but to understand the problem your solution can address. A hundred percent, when you master this, sales become less about convincing and more about connecting.
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