Back to the future: Does AI in Sales Brings Us Back to Where We Started?

Are we travelling in circles?

In the evolving landscape of sales, technology has continuously reshaped how we connect with customers. From the charismatic traveling salesmen of the Old West to today’s AI-powered assistants, sales continues to change. Interestingly, with the rise of artificial intelligence (AI), we are returning to a focus on human connection and interpersonal skills as key differentiators in sales. While it may sound counter intuitive, we’re coming full circle as we’ll discuss here. If we are coming full circle, maybe that’s less the point. It’s the distance we've traveled, and lessons learned along the way that make that journey meaningful. As Mao famously said “the delight is in the journey, and the longer the journey – the greater the delight.”

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The Personable Salesmen of the Old West

In the 19th century, American traveling salesmen relied heavily on charm, storytelling, and charisma to engage buyers, often selling dubious, universal cures, like “snake oil.” These salesmen had to use their people skills to captivate skeptical customers.

Dale Carnegie and the Art of Influence

Dale Carnegie’s 1936, "How to Win Friends and Influence People", revolutionized the approach to building human relationships in sales. Carnegie’s teachings—showing genuine interest, listening actively, and making people feel important—became cornerstones for building trust. However, the moral dilemma remains: "Can I make you like me? And even if I could, does it mean I should?" and if someone (Carnegie) had to point these out, by definition, aren’t they then already disingenuous?  

The Rise of the Subject Matter Expert

As products and industries became more complex, the role of the salesperson evolved from charming persuaders to subject matter experts (SMEs). Expertise in specific products and industries has become essential. Sales professionals who could master product features, competitive analysis, and market trends gained a competitive advantage, with expertise often overshadowing personality which partly explains the rise of the consultant. As subjects have become wider and deeper, sellers have become orchestrators of expertise, working with the various domain and subject matter experts.

The Advent of AI in Sales – Expertise on Demand?

Today, AI is reshaping sales by providing instant access to product data, customer insights, and market analytics, reducing the need for salespeople to memorize technical details. AI makes expertise available to everyone. However, AI has its limitations. It lacks the human qualities necessary for building trust, forging connections, and navigating the emotional complexities of human interaction. While AI can inform, it cannot replicate the empathy and intuition that define meaningful human relationships. I guess the question is – “does anyone care?” 

Coming Full Circle: Déjà vu

If the same AI is available to everyone, what’s left to differentiate? Are we left with interpersonal skills again? Building trust entertains contradictions. Go back to Carnegie - "do I need to like someone before I’ll invest the time to build trust, or is liking them a part of trusting them?" So I need to have a prospect convinced of our “ability” before we cross the bridge of “character” or is it the other way round? I’m not sure it matters where you fall on this, as long as you have a plan and fall somewhere!

Trust and Likability in the Age of AI

In today’s AI-driven sales environment, trust and likability are more important than ever. While AI can provide data-driven insights, clients still need to feel that the person behind the screen is trustworthy and relatable. “People like people who are like they are,” but this goes beyond surface-level charm—it’s about aligning values, goals, and needs. Emotional intelligence (EQ) is recognized as an asset for sales professionals. The ability to listen, empathize, and respond authentically is something AI cannot replicate, making these human qualities key differentiators in today’s sales landscape.

Conclusion: Forward Motion in a Circular World

Understand yourselves – be self-aware. You don’t have to be those most charismatic person in the room. If that’s not your thing, don’t play that game – you’ll lose. Play a different game. One that you can win. Admit what you’re weak at and use tools like AI to help. Building trust is about ability AND character, qualities that include, but are not limited to technical expertise By leveraging AI while doubling down on trust, likability, and emotional intelligence, sales professionals can create meaningful connections that drive success in ways the snake oil salesmen of the past could not.

Final Thoughts

The question isn’t whether you can make someone like you in pursuit of business success—it’s whether you should. Striking a balance between being authentic and making the effort to be likeable, (or at least not dis-likeable) all while maintaining integrity, is key. As we move forward in this AI-driven world, it’s essential to remember that technology may change, but there’s a fundamental human desire for connection, trust, mutual respect and meaning. Act accordingly.