On Sales

In the modern world of enterprise sales, where competition is fierce and buyers are more informed—and distracted—than ever, sales leaders often find themselves searching for an elusive edge. It’s tempting to chase new tools, ramp up activity, and double down on process. But the most transformative breakthroughs in sales aren’t found in software or scripts—they live in the nuanced psychology of how trust, safety, and decision-making unfold between people.

What Even the Best Sellers Miss

Ask a hundred salespeople what drives deals, and you’ll hear about value propositions, pricing, and features. Dig deeper and most will describe an ideal sales “process”—but far fewer will mention the hidden, human patterns that really tip the scales.

One of the most consistent blind spots? Sellers spend their energy on what they want a customer to buy, not on how the customer feels about the journey. Are you solving a sharp pain or offering a “nice to have”? Are you matching your style to the buyer’s personality and organization? Are you navigating the unspoken fears of change—the risk, the learning curve, the stakeholder anxiety?

Let’s get more specific:

1. Painkillers vs. Vitamins
   Most sellers spend too little time diagnosing whether their offer is an “aspirin” (urgent painkiller) or a “vitamin” (nice-to-have). Pitching a vitamin as a must-have irritates sophisticated buyers and stalls deals. You have to relentlessly qualify for real pain, and be willing to walk away from those who only want prevention, not relief.
2. The Psychology of the Group
   If you sell into large organizations, it’s rarely one decision-maker who calls the shots. Complex, risk-averse teams are the norm. Pitching to a single champion or relying on their enthusiasm often leads nowhere if others in the room feel skeptical, overlooked, or threatened.
3. Character Before Credentials
   It’s a mistake to think skills and experience always win. Character—reliability, empathy, the ability to own mistakes or admit limits—builds trust at a deeper level. Buyers respond, consciously or not, to people who are candid about where they fit and when they don’t.
4. Simplicity Wins
   Teams often overload presentations with multiple strategies, all-in-one decks, and complex diagrams. The result? Buyers feel overwhelmed and tune out. The most effective sales organizations distill everything to one or two simple frameworks, make the path to adoption frictionless, and reinforce their messaging habitually.

What Actually Works: The Counterintuitive Edge

Where do top-performing sales teams outperform the rest? Surprisingly, it’s not in chasing every lead or pushing harder. It’s in doing less, but doing it with discipline:

• Disqualify Frequently and Early
  The best salespeople don’t beg for every deal—instead, they professionally try to rule out prospects who aren’t a strong fit. This selective posture increases trust. When buyers sense you’re willing to walk away, they lean in, and urgency follows.
• Engineer Small Steps
  Big closes are just a series of small, low-risk commitments. Break your journey into micro-steps: a resource sent, a quick call, then another stakeholder looped in. Each “yes” builds momentum and deepens engagement.
• Deploy Well-Timed Silence
  After a big ask or sharing pricing, resist the urge to fill silences. Let the buyer process. Give space for concerns and objections to surface. Silence is often where the real deal happens.
• Sell the Cost of Doing Nothing
  People hate to lose more than they love to win. Spell out the tangible cost of inaction—let your buyers feel the urgency of the status quo, not just the promise of something better.
• Coach Your Champion
  In every complex deal, there’s a champion who “sells” for you internally. Give them the tools, language, and support to make the case—even when you’re not in the room. Your success often depends on how skillfully you empower them.

The Most Surprising Motif: The Power of Detachment

Here’s the insight that feels almost paradoxical:
The less you need the sale, the more likely you are to win it.

When salespeople approach a deal with self-assurance—willing to walk away, open about who isn’t a fit, and unattached to the outcome—buyers sense confidence, scarcity, and authority. Instead of being sold to, they feel chosen. This dynamic flips the usual logic: neediness pushes buyers away, while calm detachment invites them in.

Why does this work? Centuries of psychology tell us people crave what feels selective and hate being pressured. Confidence is magnetic. Abundant, “low-need” energy signals expertise and makes trust possible, while over-eagerness triggers skepticism and slow-play.

What This Means for CxOs Investing in AI-Driven Sales

If you’re building or transforming your go-to-market function, it pays to see past surface metrics and process charts to the deeper, behavioral science at play. Here’s how to embed these insights at scale:

• Institutionalize pain-qualification rituals.
• Design outreach for micro-commitments, not just big asks.
• Model detachment, honesty, and selectivity in your hiring and coaching.
• Enable your team to coach internal champions, not just pitch your wares.

In sales as in leadership, the edge usually goes to those who are willing not just to work harder, but to think—and behave—differently from their rivals.

The field of sales psychology is dynamic, open, and collaborative. As you bring AI deeper into sales, remember: real differentiation begins at the level of human behavior, not just automation. Codify what’s hidden. Reward what feels risky but honest. The best results come from those willing to challenge the surface patterns—and to trust the power of simple, sometimes surprising, human motives.