Overachievement in Sales is an Art, Not a Process Part 3: The Heuristic Bridge
In our exploration of sales as an art form, we've covered the limitations of pure process and the challenging complexity of enterprise sales. Now, let's tackle the crucial question: How do we bridge the gap between necessary structure and sales artistry?
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The Power of Heuristics
?Let's start with the simple definition of Heuristics shared in Part 2: A heuristic is a mental shortcut that people use to make decisions quickly before having all the relevant information. Think of it as your brain's way of dealing with overwhelming complexity.
Here's Why Heuristics Matter in Enterprise Tech Sales: Everyone—you, your customers, your competitors—use heuristics all the time. It's not a flaw in the system; it's how humans cope with complexity.
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MEDDPICC as a Heuristic Framework
Look at MEDDPICC through this lens, and something fascinating emerges. It's not just a process—it's a sophisticated heuristic framework that helps us navigate the complexity we discussed in Part 2:
1. Metrics: Quantifying value when full ROI might be impossible to calculate
2. Economic Buyer: Simplifying complex organizational structures to key decision points
3. Decision Criteria: Creating a manageable framework for numerous variables
4. Decision Process: Mapping a path through organizational complexity
5. Paper Process: Navigating procurement and legal landscapes
6. Identify Pain: Connecting solutions to human needs
7. Champion: Finding your human guide through organizational complexity
8. Competition: Understanding your position in the market
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When you view MEDDPICC this way, it artfully becomes less about checking boxes and more about creating mental models geared towards enhancing your closing ratio.
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The Art of Applied Heuristics?
Great salespeople intuitively understand this. They use frameworks like MEDDPICC not as rigid processes, but as adaptable mental models. They know when to:?
- Dig deeper beyond the standard questions
- Adapt their approach based on subtle cues
- Skip steps that might damage relationship building
- Double down on areas that resonate with specific stakeholders
When you understand the rules well enough to know when and how to bend them is when process transforms into art. Here are five examples of heuristic models that focus on individual decision-making, which can be applied to accelerate sales by understanding how people think and make choices:
1.??????? Anchoring Bias?
2.??????? Framing Effect
3.??????? Recency Bias
4.??????? Endowment Effect
5.??????? Social Proof Heuristic
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These cognitive heuristics influence how individuals perceive information, make judgments, and come to decisions. Understanding these principles allows salespeople to craft approaches that align with natural human biases, accelerating the path to closing deals. If you want to start overachieving in your sales role, I encourage you to start studying these now. Over the weeks and months to come, I’ll be going deep into this area of study, so subscribe to my newsletter.
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The Future of Sales Performance Measurement?
The emergence of large language models (LLMs) and AI is about to transform how we evaluate sales performance. More importantly, the SDR role is going to be totally automated someday, so learning to sell is going to get harder as traditional entry level jobs continue to evaporate. Soon, we might be able to analyze:
- Communication patterns across channels (phone, text, email)
- Relationship development trajectories
- Decision-making influences
- Stakeholder engagement effectiveness
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But here's the catch: Even with perfect data collection (which is unlikely given the omni-channel nature of sales—phone, email, text, dinners, rounds of golf, time at sporting events or conferences), we'll still be measuring art, not science.
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Think about it like analyzing a jazz performance. You can measure:?
- Notes per minute
- Rhythm accuracy
- Tonal precision
- Time signatures
But none of these metrics fully capture what made the performances of pianist virtuoso and composer, Thelonious Monk, and his peers, so extraordinary.
Bridging Quantitative and Qualitative?
The key to future sales excellence lies in understanding both sides of the equation:?
Quantitative Metrics (The Science)
- Activity metrics
- Pipeline velocity
- Conversion rates
- Revenue achievement
Qualitative Elements (The Art)
- Relationship building
- Timing sensitivity
- Stakeholder navigation
- Value articulation
The most successful sales organizations will be those that can:
1. Use process frameworks as guidelines, not gospel
2. Understand heuristics as tools for navigation and human interaction
3. Measure what matters while acknowledging what can't be measured
4. Foster artistic development while maintaining structural integrity?
If it’s not process, then what are the core qualities that cause over performance??
What are the skills required to compete and outperform in the “Infinite Game?” I’m writing this blog right now. Sign up to get notified when I post it on LinkedIn.
The Path Forward
As I conclude this series, here's your challenge: Look at your sales process frameworks, not as chains that bind you, but as instruments in your artistic toolkit. Understanding process is important—but understanding when and how to adapt is of greater importance.?
The best way to solve sales, unlike the Rubik’s Cube, isn't by memorizing moves, but by understanding patterns and developing intuition. The same is true in checkers and chess. And the greatest winning formula has always been: Making the right moves at the right time.
Final Thoughts – Parts 1, 2, and 3?
Sales will always be an infinite game, where the rules change, players shift, and context evolves. Process provides us a dependable foundation, so we don’t get lost, and heuristics gives us critical navigation tools. But when it comes to solving the ultimate sales equation/deal, artistry is the greatest influencer.
In the end, the greatest salespeople aren't those who follow process perfectly—but the ones who understand process deeply enough to transcend it. The ones creating their own masterpieces in the complex canvas of enterprise sales, while building mutually beneficial relationships to effectively meet the client needs. The best sales and relationships are long-term and laser-focused on creating and delivering exceptional value for all concerned parties. ?
I propose that sales success doesn’t get any better than that!
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?This concludes our three-part series on the art of enterprise technology sales. Thank you for joining me on this exploration of process and artistry in modern sales.
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