♖ Relentless Empathy

Hi Friends,

Ten years ago, I was sitting in a sales training workshop in San Jose, CA with Jeff Thull, author of Mastering the Complex Sale, and one of the world's foremost experts on B2B sales.

At the end of the workshop, Jeff handed me a foldable wallet card.

It had his most important teachings on a single page.

It's been bent, coffee-stained, and carried through countless airports and boardrooms. But it's never left my wallet.

What Jeff taught me completely changed how I think about B2B sales. He obsessed over one thing: deeply understanding your customer's world before you say anything about yours.

That insight shaped everything. And now, 3 weeks into leading growth at Pricing I/O, our team's philosophy can be summed up in two words: Relentless empathy.

Empathy means showing up like a doctor, not a waiter. It's the discipline of deeply understanding a client's problems, context, and risks before suggesting any solution. It's the opposite of rushing to pitch.

By the end of this issue, you'll know the core principles to run more trusted, effective B2B sales conversations.

Why Empathy > Enthusiasm in B2B Sales

Most salespeople act like waiters. They take orders, nod politely, and hope the prospect leaves a good tip.

The problem? Waiters don’t solve business problems, they serve what’s already on the menu.

B2B buyers don’t need another waiter. They need a doctor. There is market chaos out there with so many “me-too” solutions all promising the same outcomes.

What prospects really need are trusted advisors who can ask tough questions, run a diagnosis, and guide them to the right solution they didn’t fully understand before.

This is where the 4D sales process comes in.

The 4D Sales Process

This framework is designed to guide prospects in making an effective decision (not just close a sale). Each step isn’t just a box to check, it creates a specific outcome that lowers buying risk, builds trust, and accelerates decisions.

1. Discover

• Purpose: set the stage for trust and credibility before a single question is asked.

• Do your homework: study the client’s market, competitors, executives, and pricing dynamics. Come ready to share insights.

• Why it matters: Credibility is established in the first 5–10 minutes. Buyers decide quickly if you’re a vendor or a trusted advisor.

• Outcome: Establish enough trust and context that the buyer feels understood and is open to a deeper diagnostic conversation.

2. Diagnose

• Purpose: shift the conversation from symptoms to root causes.

• Ask layered questions that uncover both business and personal risks. Buyers often struggle to quantify their own problems until someone leads them there. Goals without numbers are wishes.

• Why it matters: Gartner research shows 77% of B2B buyers say their last purchase was “very complex or difficult.” Diagnosis reduces this complexity.

• Outcome: Reach shared clarity with the buyer on the true problem, its cost, and the risks of inaction.

3. Design

• Purpose: move from discovery to co-creation.

• Instead of prescribing too early, collaborate with the client to shape the right solution.

• Why it matters: when buyers co-design the solution, they become internal champions. Most “no decisions” stem from lack of internal alignment, not lack of interest.

• Outcome: Create a solution the buyer feels they co-authored and is motivated to champion internally.

4. Deliver

• Purpose: ensure the decision is both confident and timely.

• Quantify urgency by calculating the business cost of doing nothing, dollars left on the table, risks unmitigated.

• Why it matters: without urgency, even strong solutions stall. This is the “value gap”—buyers won’t act unless the cost of inaction outweighs the cost of change.

• Outcome: Ensure the buyer commits to a quality business decision that is timely, quantified, and delivers lasting value.

How We’re Building It at Pricing I/O

Here’s what we’ve operationalized it so far:

• Pre-discovery prep → Before every meeting we now complete a pre-discovery checklist which includes management team bios, key goals, market intel, financials, competitors, product features, pricing page, and any hypothesis of potential issues. This is a valuable tool to also share internally to alleviate handoff concerns.
  

• Diagnose deeper → We’ve created a set of discovery questions to uncover root issues (not high-level symptoms) and have run role-playing sessions to improve the process.
  

• Design together → No cookie-cutter pitches. Our amazing pricing strategists are part of the sales cycle to listen and go deep with prospects. There is so much value delivery in just this process for clients.
  

• Quantify urgency → We built a new ROI quantification tool to help educate clients on how our efforts tie to their business objectives. Goal is to co-create this with prospects to help make it feel that this is “their” tool to support the decision making process.

It’s early days, but the shift is already visible. Our conversations feel more like strategy sessions than sale transactions. Will continue to improve and report back how things evolve.

Takeaways

Here are the principles to focus on. Apply these consistently and you’ll succeed:

1. Credibility in minutes. As a buyer of products & services, I’m amazed how unprepared sales people are despite all the tools available at their disposal. Prepare before every call so the buyer immediately sees you as a trusted guide, not a vendor.
   

2. It’s about them, not you. Never pitch until you’ve uncovered and agreed on the real problem and its cost.
   

3. Co-create the path. Involve the buyer in designing the solution so they own it and sell it internally.
   

4. Quantify urgency. Always translate the cost of inaction into numbers. No urgency, no deal.

My favorite line in the wallet card: Prescription without diagnosis is malpractice.

The best B2B sellers act like doctors. They show relentless empathy to diagnose the problem and guide the buyer toward the right decision for them.

That’s the kind of sales culture we’re building here at Pricing I/O.

Til next time,

—Ali

P.S. I'm building a reading list for our sales team. What's the one sales book you'd recommend that actually changed how you sell? Reply with your pick. I'll compile the best ones for a future issue.

About Me: I'm Ali, the VP of Growth at Pricing I/O and have been listening to “Catch My Breath” by Kelly Clarkson on repeat for the last few hours writing this. Come follow my journey on LinkedIn.