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Deal Inspection

Kathleen’s chapter in McMahon’s book is a goldmine for deal inspection.

EnterpriseChai 2026-02-16

Kathleen’s chapter in McMahon’s book is a goldmine for deal inspection.

It exposes three foundational truths that most pipeline reviews miss.

Deals don’t close in the middle of the quarter after one call.

If a customer says they'll buy this week after hearing about your product for the first time last week, the probability of closing is near zero.

Why?

  • No champion alignment
  • No consensus
  • No internal justification
  • No procurement path
  • No real pain established
  • No urgency
  • No reason to buy now

These are 5-risk signals, especially for new vendors.

Obsessing over one feature is not the same as wanting the product.

This is a subtle but powerful signal.

Customers will say things like:

  • “We love that one capability…”
  • “We’re excited about this one thing…”

But if they never say:

“We need your platform for X reason,”

the feature is a distraction, not a deal.

Sales leaders must detect:

  • Feature praise vs actual need
  • Whether the feature exists in competitor products
  • If the customer is shopping the category (Gartner, Magic Quadrants, G2, analysts)
  • Whether the category suggests competing evaluation motions

This is an external + internal coalesced signal.

Customer POC criteria is NOT validation.

Customers often propose POC requirements that:

  • Your product can only partially satisfy
  • Require configuration you don’t have
  • Test capabilities outside your roadmap
  • Stretch your platform into unrealistic territory

Sales leaders should identify:

  • Which POC criteria map to real features
  • Which don’t
  • Which require workarounds
  • Whether your product can actually win under that evaluation

Otherwise, your reps are forecasting a POC you’re destined to lose.

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