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  • A Lesson from an “Old School” Seller

A Lesson from an “Old School” Seller

Jim Marshall May 8, 2025

  … on Engaging Effectively in the AI era

That’s the biggest stereotype some people have about the “typical salesperson”?

It could very well be the one-dimensional schmoozer depicted in movies, or television, many years ago. Pushy. Fast-talking. Fixated solely on closing the deal. Not always completely honest.

But it’s not a stretch to say stereotypes are often based in reality. Many sellers were—and some still are—pushy, fast-talking and fixated solely on closing the deal. But what valuable lessons can we learn as sales professionals from the “old school” model?

When you examine that stereotype closely, you’ll realize there’s plenty of useful insight lurking behind it. Relationship-building matters. Real-time social bonding matters. Introductions from trusted contacts matter. Networking matters. Connection around nonwork-related topics matters. There’s nothing wrong with taking a client to a ball game or golfing. There’s nothing wrong with deepening relationships over time, through enjoyable activities and interactions. These just aren’t the entire job description.

The data-driven salesperson

Fast-forward to today. What distinguishes the most successful salespeople now, from just a few years ago? What are top-performing salespeople doing differently in this era of AI, data analytics, remote selling and buyer-empowered customer journeys? Which best practices are now making a difference that weren’t even on our radar before the pandemic?

The most effective sellers recognize they’ve never learned it all. They’re open to new platforms and tactics. They operate in a digital-first landscape—a working world where adopting modern technologies, relentless self-development and a customer-centric approach are paramount. They expertly leverage advanced CRM systems, massive, constantly updated databases, artificial intelligence and data analytics to personalize their approach. They don’t rely on generic scripts or mass email blasts. Instead, they use advanced information tools to create outreach and follow-up messaging tailored specifically to each recipient.

These salespeople understand that today’s buyers are inundated with spam and possess vast amounts of information at their fingertips. They anticipate customer questions and needs, delivering customized responses. And yes, these salespeople build relationships over time. They sustain engagement through various digital tools that enable consistent, seamless interactions across multiple channels and touchpoints.

There is both an “old school” approach to selling and a newer, data-driven approach. To succeed as a sales professional today, we must use what works best from both perspectives.

The “old school” mentality emphasizes rapport, connections, influence and relationships to overcome sales challenges. The data-first mentality, on the other hand, risks turning salespeople into marketers by minimizing, or entirely overlooking, the critical face-to-face or voice-to-voice connections that launch and sustain important relationships.

Here’s the takeaway: When interacting effectively with the large (and growing) cast of characters influencing buying decisions within an organization, today’s most productive sales professionals harness both the power of data and personal relationships. They connect the dots, using innovative tools to build rapport, nurture relationships over time and earn the trust, goodwill and loyalty of their clients. They leverage the best of both the “old school” and the “data-driven” approaches.

Jim Marshall
Jim Marshall

So, how would you characterize your typical approach to selling and business development?

Jim Marshall is the founder of Sandler Training of Tampa Bay, which provides sales and management training and coaching to high-achieving companies and individuals.
Contact him at 813.287.1500 or [email protected].

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