Overachievement in Sales is an Art, Not a Process Part 2: The Infinite Game

November 13, 2024

I keep a 3×3 Rubik’s Cube on my desk. My team finds it amusing, but there’s a reason why I placed it there. The cube serves as a constant reminder of the mind-bending complexity everyone in the enterprise tech sales industry must navigate daily.

Here’s why: The Mathematics of Human Complexity

Consider these numbers:

– Rubik’s Cube: 43 quintillion possible combinations

– Checkers: 500 quintillion combinations (I mean their only checkers!)

– Chess: 10^40 possible situations

– Go: Comparable to the number of atoms in the universe (roughly 10^80)

Impressive numbers, right? Now, let’s look at Enterprise Sales.

Breaking Down a “Simple” Sales Scenario

Let’s use MEDDPICC as our framework and create what appears to be a straightforward thought experiment:

– Remove competition (sell why you’re the only solution)

– Simplify legal/procurement to one decision-maker

– Limit yourself to just seven stakeholders

– Assume only three possible outcomes at each stage (Yes, No, Maybe)

– Factor in 16 different personality types (using Myers-Briggs as a reference)

The math? You’re looking at 587,068,342,272 (48^7) possible combinations. 16 different ways to get to yes, no, or maybe or 16*3 = 48. So, 7 different steps in the process = 48^7 different potential scenarios in even this simplified version of reality. And that’s the sanitized version.

You’re usually dealing with:

– Multiple stakeholders (who may or may not be aligned with the objectives)

– People who aren’t aligned with their business’ best interests

– 3-5 competitors

– Complex procurement and legal teams

– Technology that may or may not perfectly solve the customer’s pain

– Political dynamics you can’t see

– Budget realities you don’t know about

– Timeline pressures you’re unaware of

– FYI – Your champion is getting a job offer

– Board is firing the CEO, so there’s a 6-month halt on all IT purchases until there is a new “strategy.”

The “Infinite Game”

I refer to sales as the “Infinite Game.” Because when things go wrong, my Rubik’s Cube reminds me that enterprise technology sales is incredibly challenging. And when things go right, it prompts two crucial thoughts:

1. Success might involve luck—keep working hard

2. Success always involves countless others—from product managers to engineers, partner teams, solutions architects, and your executive team. (Humble and Hungry!)

The Process Paradox Revisited

Now you can see why reducing this complexity to an eight-step process is problematic. It’s like trying to capture the entire ocean in a drinking glass. Yes, MEDDPICC and similar frameworks are valuable navigation tools. I recently bought Andy Whyte’s book, MEDDICC, and will share my thoughts on it with you soon.

Understanding Human Decision-Making

This brings us to a critical concept: Heuristics. Simply put, a heuristic is a mental shortcut people use to make quick decisions before acquiring all relevant information. Humans love heuristics—that’s how we usually navigate life’s complexity.

Your customers use heuristics. You use heuristics. Everyone uses these mental shortcuts because the alternative—trying to process all 587,068,342,272 possibilities—would paralyze us. (I’ll be going deep into heuristics in future blogs. Because understanding heuristics are what separates the average and top performers.)

The Leadership Challenge

This complexity creates a fascinating tension in sales organizations. Leadership requires metrics, forecasts, and predictability. Leadership has to answer to board members, VCs/PEs, and/or stockholders who want clear, quantifiable answers. But they’re all trying to measure and predict something that’s fundamentally as complex as a game of Go. It’s exceptionally hard!

That’s why we often see companies embracing process framework as a means of perceiving stability/success during tough times. Process feels safe. Process feels manageable. Process feels measurable. Should top salespersons be let go because they forgot to update the CRM with who the economic buyer is when an opportunity is in prospect phase? Probably not! They want to get paid, so they’ll know when the time is right to update the CRM. Because they’re the ones on the front lines every day, AEs are the best positioned humans to understand and manage this.

Looking Ahead

In our final installment, we’ll explore how to bridge the gap between necessary process and artistic sales execution. We’ll dive deeper into heuristics and examine how emerging technologies, like large language models, might change how we evaluate and improve sales performance.

For now, remember this: Every sales interaction is unique. Every human decision is complex. Every consummated deal is a masterpiece in successfully navigating countless variables. That’s why, at their highest level, sales will always be more Art than Process.

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This is Part 2 of a three-part series on the art of enterprise technology sales. Stay tuned for Part 3, where we’ll explore how to bridge the gap between Process and Artistry in sales.

Link to article #1: https://www.linkedin.com/pulse/1a-technology-sales-art-process-part-1-beyond-paradigm-prozaki-4jocc/?trackingId=%2FclRk4%2FmQV2nGLpd%2B7OhZQ%3D%3D

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