The world of selling has changed faster than most sales playbooks. I’ve been in sales for close to 40 years. Over those decades, I’ve seen sales professionals operate in a predictable environment where customer needs were stable, competitors were known, and sales cycles followed familiar patterns. In that world, a defined sales process made perfect sense. I can still remember how fascinated I was when a Silicon Valley company I worked for brought in two sales consultants to introduce a robust sales process. That was my first introduction to having a formal process that was set up in the CRM and that we were expected to follow. I was also fascinated by the analysis that was done to identify where each salesperson may be struggling to implement the process. The understanding was if each salesperson executed the prescribed steps in order, results were consistent and repeatable. And the results proved that understanding was right.
That world is gone
Today we live in a volatile, uncertain, complex, and ambiguous environment. Customers are fragmented across functions. Internal pressures shift weekly. Decision criteria evolve mid-conversation. What works beautifully with one customer falls completely flat with another. Leaders feel this every day: the old linear sales process simply can’t keep up with a world that won’t sit still.
This shift is a lot like the difference between checkers and chess. Checkers is predictable. The moves are limited, the patterns repeat, and the game unfolds in familiar ways. Traditional sales processes were built for this level of predictability.
Chess is something else entirely. Every move reshapes the board. Possibilities multiply. Experts estimate that after just 5 or 6 full moves (for both sides) players may already be in a position not found in large game-databases. By the time players reach the 20th move, it’s very likely they’re playing a game that has never been played before. There is no script. There is no sequence. There are only principles—fundamental truths—that guide judgment in the face of complexity.
Modern selling works the same way
Top-performing salespeople aren’t the ones who rigidly follow prescribed steps. They’re the ones who understand the underlying principles that make those steps meaningful. They know how to read the board, anticipate consequences, and choose the right move in the moment. They adapt their strategy while staying grounded in what creates value for the customer.
A few of the principles that matter most today:
• Start with the customer’s strategic context, not your agenda.
• Strengthen trust by acting as a guide on their journey—not the hero of your own story.
• Navigate stakeholders as an interconnected system.
• Reduce the customer’s risk in every interaction.
• Co-create value by helping them advance their highest-priority goals.
These principles don’t replace the sales process—they elevate it. They provide the judgment, flexibility, and situational awareness needed to execute effectively in a world where no two conversations look alike.
For sales leaders, this shift requires a different kind of coaching. Instead of policing compliance to stages, develop your team’s ability to think strategically, apply principles, and make sound decisions under pressure. In a complex environment, that’s the real multiplier.
Selling today isn’t checkers. It’s chess. And the organizations that win are the ones who equip their teams with the principles—not just the process—to play the game at a higher level.
