Why Your Best Salespeople Are Always Uncertain
I watch faces, not spreadsheets. When I deliver an insight that shifts someone's thinking, I'm not just looking at their words; I'm reading the micro-expressions, the slight pause, the shift in posture. That moment of recognition changes everything.
As we increasingly produce content, presentations, and sales pitches using AI, we risk 'unlearning' crucial communication skills.
The Reactions Machines Cannot Read
I often observe powerful examples of these reactions to insights in my coaching workshops. For instance, many sales leaders discover their 'coaching questioning' style frequently creates defensive reactions from sellers instead of encouraging exploration. In these moments, leaders realise sellers might even manipulate information to align with expectations rather than convey factual truth.
This reaction is undeniably uncomfortable. Their numbers, forecasts, and entire understanding of the business suddenly feel false. At this point, a leader might find themselves in a challenging position without a clear path forward. Often, all it takes is for me to reach out and offer a way forward.
The Small Step Strategy
An offer or recommendation must be clear, actionable, and valuable. But here's what truly separates human insight from algorithmic suggestions: the small step.
The small step or recommendation I'm referring to isn't defined by me, the seller, but by the buyer's ability and willingness to execute it. Sometimes, the recommended action step must be so minor that the risk of not taking it far outweighs the risk of taking it. This demands reading context, understanding stakeholder dynamics, and navigating internal politics—factors no spreadsheet-based conversation history can easily capture.
Traditional selling asks: "What do I want them to do?" I ask instead: "What are they actually capable of doing right now?"
Customer Business Improvement First
The biggest mental shift salespeople must make sounds simple, yet it transforms everything.
They must think of customer business improvement first and foremost. There can be no evident self-interest; every question must lead to business improvement at all costs. While everyone knows I'm in business to sell, the key is to suspend my own agenda and realise my business only thrives when I drive customer business improvement.
When salespeople truly grasp this concept, their intrinsic curiosity shines through in their preparation. Their key questions become: "What else is possible?" and "What have they missed about themselves?"
The Three-Part Framework
My Thinking Planner connects this human-centred approach through three sections:
Information gathering: Where sellers learn about the customer's business through the customer's lens and perception of their truth.
Context strategising: Where sellers determine what the information truly means to the customer in terms of business impact.
Action planning: Where the focus is on the buyer's next step, not the seller's agenda.
AI can efficiently handle the first section and even assist with business impact analysis. However, that crucial middle piece requires uniquely human capabilities: anticipating what could go wrong, reading stakeholder dynamics, and sensing internal objections before they surface. This demands the ability to see beyond facts and rely on intuition built from experience.
Embracing Productive Uneasiness
One tell-tale sign of sales excellence might surprise you. It's when sellers shift from justification to exploration in their thinking and questioning, becoming chronically uneasy, always wondering what they or their customers are missing.
Most people see that uneasiness as weakness; I see it as mastery.
The problem is that our systems often punish this type of thinking. Sales leaders demand certainty when the best sellers are saying, "I'm not sure, let me explore further." The solution is to embrace the discovery of gaps and adopt a collaborative approach to closing them. Instead of punishing uncertainty, I celebrate the discovery of what's unknown. This transforms the entire customer relationship from transactional to truly transformational.
In a world where AI handles more sales tasks every day, the human edge becomes more valuable, not less. The future belongs to those who can read reactions, embrace uncertainty, and turn collaborative gap-closing into a competitive advantage. Your best salespeople aren't the ones with all the answers; they're the ones asking the questions machines never think to ask.