Internal Deal Strategy & Escalation
Run a deal review that actually changes the plan, and write escalations that get fast, defensible answers from Deal Desk and leadership.
Two operating mechanisms make or break internal selling: the and the . A weak deal review is a status report; a strong one stress-tests the plan, surfaces hidden risk, and produces named next moves. A weak escalation is a Slack ping at quarter-end; a strong one is a one-page memo that pre-answers the 's questions.
Deep practical explanation
Deal reviews. Use a consistent format: deal facts, score, top three risks, three asks the room, and one specific next move. Force the to articulate the loss path: 'If this deal slips, the most likely reason will be X.' Strong managers spend most of the review on the loss path, not the win path.
Escalations. Treat them as written work. The format: situation, ask, recommendation, customer impact approval, customer impact of denial, internal precedent, expiration date. Approvers who get this format five days early approve; approvers who get a hallway question the day-of decline by reflex.
Real-world example
An needed a 28% discount approval on a $700k deal — well above their . They sent a Slack message to the lead at 4pm on the last day quarter: 'Need this to close tonight, can we approve?' Predictable answer: no.
The rebuild for the next deal: a one-page memo sent the previous Friday, including the customer's competitive context, three comparable approvals at peer accounts, the multi-year structure that justified the discount, and a sign-off line. The discount was approved by Tuesday. The deal closed on the Thursday.
Tactical steps
- Run a weekly on every Tier 1 deal; spend 70% the time on the loss path.
- Score every deal against every week — re-score after every customer interaction.
- Bundle every non-standard ask into a single, written memo.
- Send escalations 5+ days before the customer deadline; never on the day.
- Make a recommendation; never escalate without a position.
- Close the loop with approvers — what closed, what didn't, what you would do differently.
# ESCALATION — [Customer / Opportunity] From: [AE] Manager: [name] Approvers needed: [Deal Desk / Legal / VP / CRO] Customer deadline: [date] Internal need-by: [date 5+ days earlier] ## SITUATION [2–3 sentences. The customer, the deal, the stage, the stuck point.] ## ASK [Specific. Quantified. Bounded.] E.g. "Approve a 22% discount on a 3-yr $1.4M ARR deal in exchange for prepaid Year 1 and a logo-rights commitment." ## RECOMMENDATION [Approve / approve with conditions / decline + alternative] ## CUSTOMER IMPACT — APPROVAL [What happens if we say yes — closure timing, expansion path, reference] ## CUSTOMER IMPACT — DENIAL [What happens if we say no — slip, competitor, downsize, walk] ## PRECEDENT / SCALE - Comparable approvals: [Account A — 24%; Account B — 20% with prepay] - Strategic value beyond ARR: [reference, market signal, displacement] ## RISKS / TRADE-OFFS 1. [trade-off + mitigation] 2. [trade-off + mitigation] ## EXPIRES This recommendation is valid until [date]; after that, the customer structure changes and we will need to re-scope.