#My Best Sales Advice, Chris Herring

For two years, Chris and I shared a cramped office in Adams Morgan, back when the building still stood. We were colleagues, complete opposites, and soon-to-be lifelong friends.

Chris started his sales career in Charlotte, NC, before moving to Washington, DC, with his wife and kids. Over the years, he climbed the ranks—from seller to sales manager to running a large digital team in Pittsburgh.

When I asked him:

💬 “What’s the best sales advice you’ve ever received?”

His answer was straightforward but powerful:

Chris’s Best Sales Advice

💡 "Work hard to discover the decision-maker’s motivation and satisfy it. That’s often the only true differentiation you can offer—and it gets you to the buyer’s actual need."

Why Understanding Buyer Motivation is Everything

📌 Most salespeople focus on what they’re selling.
✅ The best salespeople focus on why the buyer is buying.

It’s easy to pitch features and benefits, but buyers don’t just want a product or service—they want a solution that solves their unique problem.

🚨 The challenge? Buyers don’t always tell you what they really need upfront.

👉 Your job as a salesperson isn’t just to sell—it’s to uncover the deeper motivation behind the request.

Example: Selling Beyond the Surface-Level Need

Imagine a marketing department approaches you about a software solution to improve communication channels.

At first glance, it seems simple:
📌 They need a tool to streamline messaging.

But after digging deeper, you learn:
🔹 The real issue? A hiring freeze.
🔹 Automation is a necessity, not just a preference.
🔹 The buyer wants their team to manage the software—once the hiring freeze ends.

📢 If you only pitch the software, you’re just another vendor.

How to Stand Out & Win the Deal

💡 Go beyond the obvious need and address the true motivation.

Instead of just offering software, present a tailored solution:
✅ Software implementation with interim staffing support
✅ A training plan to transition management to their in-house team after hiring resumes
✅ A roadmap showing how automation bridges their short-term needs with their long-term goals

📢 By aligning with the buyer’s motivations, you’re no longer selling a product but solving a problem.

How to Apply This in Your Sales Process

Want to uncover real buyer motivations? Ask better questions.

🔹 Instead of: “What are you looking for?”
✔️ Ask: “What triggered this need?”

🔹 Instead of: “What’s your budget?”
✔️ Ask: “What’s driving the financial decision behind this investment?”

🔹 Instead of: “What solution are you considering?”
✔️ Ask: “What concerns or roadblocks might prevent this from moving forward?”

💡 Your job isn’t to pitch first—it’s to understand first.

Final Takeaway: Solve for the Buyer, Not Just the Sale

🚀 The best salespeople don’t sell products—they sell outcomes.

✅ Find the buyer’s true motivation, and you’ll differentiate yourself from the competition.
✅ Dig deeper than the surface-level request—real value lies in the "why."
✅ When you align your solution with their long-term success, you don’t just close deals—you build relationships.

📢 Bottom line: If your product isn’t unique, your ability to solve the right problem can be.

About Chris

Chris is the Director of Digital Marketing at BarkleyREI, a full-service digital marketing agency specializing in strategy, analytics, and performance marketing.

📢 BarkleyREI leads digital advertising and website design projects for top universities, tourism brands, and nonprofits.

💡 Fun fact: As a buyer, Chris is highly motivated by Oreo Blizzards from Dairy Queen. (Salespeople, take note.)

🔗 Learn more: www.barkleyrei.com