Sherwin’s 10 Deadly Sins of Sales: An Autopsy of Manual Execution
During my three decades in sales leadership roles at large enterprises, early-stage growth companies, and my management consulting practice, I have witnessed and corrected many bad sales practices. In the world of Revenue Architecture™, we call these “systemic friction.” If not course-corrected, they lead to zero sales. When they numbered an even ten, they became Sherwin’s 10 Deadly Sins of Sales.
1) I’ll pretend to sell… if you pretend to buy. – The Deadly Embrace.
There is nothing Karen, the salesperson, likes more than showing up at the weekly pipeline call with a big potential deal. In the RAOS world, this is a failure of FACT qualification. Karen is ignoring “Authority.” Her buyer, Charlie, is four levels down the food chain. They are in a deadly embrace of ego—Karen wants a “hero” deal, and Charlie wants to feel important. Both are stalling deal velocity by ignoring the structural reality of the account.
2) Not yet, I’m still preparing.
Mike, a meticulous salesperson, has a mountain of color-coded folders but zero first-hand intelligence. This is “Analysis Paralysis” in Layer I (Strategy). He is building a Market Definition (PB1) on paper but failing to trigger a single play. In an engineered system, “Preparation” has a time-bound input and a required output (the meeting). Mike is stuck in the logic flow.
3) Not yet… I’m not done consulting.
Rick, a partner at a major firm, is stuck in “Trusted Advisor” limbo. He brandishes knowledge but never asks for the order. By the time he does, the window has closed. In RAOS, Opportunity Orchestration (PB8) requires moving from a “Working Lead” to a “Qualified Prospect” using a defined call to action. Consulting is the value; selling is the execution. Don’t confuse the two.
4) My idiot customer just doesn’t get it.
If a prospect “doesn’t get it,” the failure lies in your Value Proposition Chain. Specifically, a break between Audience Value (AVP) and Offer Value (OVP). It is the architect’s job to align the solution with the client’s need. “They don’t get it” is a symptom of poor positioning, not a customer defect.
5) Wait right there; let me get the “real salesperson.”
When Subject Matter Experts (SMEs) take over but ignore the FACT model—ignoring decision criteria and competitive threats—the deal loses its structural integrity. Salespeople and experts must be joined in a unified Account Plan. An expert who doesn’t understand the “Pain Ladder” is just a lecturer, not a deal-closer.
6) So what …who cares?
My mentor Duane taught me this: if you can’t articulate why a feature matters to the client’s specific pain, you haven’t climbed the Pain Ladder. You are stuck at Layer 1 (Operational Symptoms) when you need to be at Layer 3 (Personal/Reputational consequences). Every message must align with Actual Customer Value (CVP).
7) My hygiene is great; leave me alone.
A project can be on time and on budget (“Hygiene”), yet the account “Health” is failing. If you only have 12% of wallet share, you are missing 3C Expansion opportunities. Within Account Optimization (PB9), we look for Continuations, Crop Rotations, and Colonizations. Good hygiene is the baseline; health is about expansion.
8) I’m selling for a hypothetical company.
“If only we had this feature…” is the anthem of the struggling rep. You must sell for the firm you have, not the one you wish you had. Effective GTM Architecture (PB3) frames the client’s problem in terms of your actual, current capabilities. Deliver insights for the roadmap, but execute with the tools in hand.
9) Let’s keep investing … one day we’ll win this deal!
The hardest thing in sales is knowing when to stop. Without a FACT-based scoring system, you spend “personal money” on low-probability Omahans. RAi helps remove this emotional bias by providing structured reasoning—if the “Timeline” or “Competition” metrics don’t align, the system signals a “Stop Loss.”
10) If I had a hammer, you’d have a nail.
If your only tool is a hammer, every problem looks like a nail. While we sell what we have (#8), engineered execution starts and ends with the client’s unique friction. RAOS provides the full toolbox of 27 plays to ensure we aren’t just hammering—we’re building.
Sherwin Uretsky is a Managing Partner with Revenue Architects. He helps businesses transform their front office through the Revenue Architecture Operating System (RAOS) to drive sustainable growth.
