Introduction
Every CRO I know has lived through this moment.
You’re in the weekly forecast call. A large deal—one that materially affects the quarter—is sitting confidently in “Commit” or “Best Case.” The account executive sounds optimistic. The CRM shows recent activity. Meetings are happening. Notes say things like “good engagement” and “positive feedback.”
Then, quietly, the deal slips.
No dramatic loss email. No explicit “we went with someone else.” Just delays. Pushed decision dates. Stakeholders suddenly “busy.” Eventually, the deal either dies or moves to the next quarter—where it slowly bleeds out.
What’s frustrating isn’t that deals are lost. That’s sales.
What’s infuriating is when deals look healthy right up until they don’t.
As a CRO with hands-on pipeline ownership, this is where I spend most of my time—not on closing techniques, but on risk detection. The earlier you spot risk, the more leverage you have to fix it. The later you spot it, the more you’re managing disappointment instead of revenue.
This article is about how to use ChatGPT as a deal risk lens—not to replace judgment, but to pressure-test optimism, expose blind spots, and surface uncomfortable truths before they show up in your forecast miss.
No hype. No “AI magic.” Just a structured way to look at deals more clearly.
The Problem
Why Deals Appear Healthy But Fail
Most deals don’t fail because something suddenly goes wrong. They fail because something was wrong all along, but no one named it.
In my experience, deals that collapse late usually share one or more of these characteristics:
- The buyer was polite, not committed
- The rep mistook activity for progress
- Risk signals were present but normalized
- Assumptions replaced validation
The CRM didn’t lie—but it also didn’t tell the truth.
Pipeline Blind Spot #1: Activity Masquerading as Momentum
Meetings, demos, emails, follow-ups—these are inputs, not outcomes.
A deal can have:
- 12 meetings
- Multiple demos
- Frequent emails
…and still be going nowhere.
Why? Because none of those activities answer the real questions:
- Is there a compelling reason to buy now?
- Is there an internal owner pushing this forward?
- Is there a decision path we’ve validated?
When CROs look at pipeline dashboards, activity-heavy deals often look “safe.” They aren’t.
Pipeline Blind Spot #2: Buyer Politeness Interpreted as Intent
Experienced sellers know this, but it still happens.
Buyers say things like:
- “This is interesting”
- “Let’s keep talking”
- “We like what we’re seeing”
Reps hear momentum. Buyers may simply be being professional.
Without explicit confirmation of:
- Business priority
- Economic buyer involvement
- Decision criteria
…interest becomes a dangerous illusion.
Pipeline Blind Spot #3: Unchallenged Rep Optimism
Good reps are optimistic by nature. That’s not a flaw—it’s often why they succeed.
But optimism becomes dangerous when:
- Assumptions go untested
- Risks are minimized
- “I think” replaces “They said”
In forecast reviews, you’ll hear:
- “I feel good about this one”
- “They’re aligned”
- “It should close”
None of those statements are evidence.
Pipeline Blind Spot #4: Risk Signals That Feel Normal
Some risks are so common they stop triggering alarms:
- “Procurement still needs to review”
- “Legal hasn’t weighed in yet”
- “We need to loop in finance”
These aren’t minor details. They’re structural risks.
But because they show up late in many deals, teams accept them as “part of the process” instead of treating them as deal threats.
ChatGPT Prompts
The goal here is not to ask ChatGPT, “Will this deal close?”
That’s useless.
The goal is to force structured thinking around:
- Deal health
- Buyer intent
- Risk signals
- Assumptions vs. facts
Below are step-by-step prompts you can use as a CRO, VP Sales, or senior manager to analyze deals more rigorously.
Prompt 1: Deal Health Reality Check
Purpose:
Strip away optimism and assess the deal based on evidence.
When to use:
Before forecast calls, QBRs, or executive reviews.
Input to provide:
Deal notes, stage, forecast category, and recent activity summary.
Prompt:
You are a Chief Revenue Officer reviewing a sales deal for forecast accuracy.
Based on the information below, assess the true health of the deal.
Identify:
- Evidence-based strengths
- Assumptions or unvalidated beliefs
- Missing information required to confidently forecast this deal
Be critical and specific.
Deal details:
[Paste deal notes, stage, and activity summary]
What this surfaces:
Where confidence is built on facts—and where it’s built on hope.
Prompt 2: Buyer Intent Analysis
Purpose:
Differentiate curiosity from commitment.
When to use:
When deals linger in mid or late stages.
Input to provide:
Buyer statements, email excerpts, meeting outcomes.
Prompt:
Analyze the buyer’s intent based on the following interactions and statements.
Categorize intent as:
- Curious
- Evaluating
- Committed
Explain your reasoning and highlight what evidence is missing to confirm strong buying intent.
Buyer interactions:
[Paste notes or excerpts]
What this surfaces:
Whether the buyer is actually moving toward a decision—or just learning.
Prompt 3: Risk Signal Identification
Purpose:
Make hidden risks explicit.
When to use:
For any deal in Commit or Best Case.
Input to provide:
Full deal timeline, stakeholders, objections, and blockers.
Prompt:
Review the following deal information and identify potential risk signals.
Focus on:
- Stakeholder gaps
- Decision process uncertainty
- Timing risks
- Competitive or internal resistance
Classify each risk as Low, Medium, or High impact.
Deal information:
[Paste details]
What this surfaces:
Risks that are often ignored because “they’re normal.”
Prompt 4: Deal Progress vs. Deal Movement
Purpose:
Separate motion from progress.
When to use:
When deals have many activities but no clear advancement.
Input to provide:
Meeting history and outcomes.
Prompt:
Based on the following deal activity, evaluate whether the deal is truly progressing or simply staying active.
Identify:
- Actions that moved the deal forward
- Actions that maintained engagement only
- What must happen next to create real movement
Activity summary:
[Paste summary]
What this surfaces:
Whether time is being invested wisely—or wasted.
Prompt 5: Close Risk Forecast Adjustment
Purpose:
Pressure-test forecast category.
When to use:
Before locking forecasts.
Input to provide:
Current forecast category and justification.
Prompt:
Given the deal details below, assess whether the current forecast category is appropriate.
If not, recommend a more accurate category and explain why.
Highlight what must change for the deal to earn its current forecast status.
Deal details:
[Paste details]
What this surfaces:
Forecast inflation—and how to correct it.
Real Example
Let’s walk through a realistic deal.
Deal Name: Atlas Manufacturing
Deal Size: $280,000 ARR
Stage: Proposal Sent
Forecast Category: Commit
Close Date: End of current quarter
Raw Deal Notes (As Seen in CRM)
Multiple demos completed
Strong interest from Ops team
VP Ops positive on solution
Discussed pricing, some pushback
Procurement review pending
Legal not engaged yet
CFO not on calls
Rep feels confident
Customer says timing depends on internal approvals
On the surface, this looks decent. But let’s apply structured analysis.
Sample Output
Deal Health Assessment (Using Prompt 1)
Strengths (Evidence-Based):
- Multiple demos completed
- Clear operational pain identified
- VP of Operations engaged and positive
Assumptions / Unvalidated Beliefs:
- VP Ops can drive final approval
- Procurement and legal review will be quick
- Pricing pushback won’t delay decision
- CFO alignment is implied, not confirmed
Missing Information:
- Confirmed economic buyer involvement
- Defined approval sequence and timeline
- Explicit business case tied to financial impact
- Clear “decision date” owned by the customer
Overall Assessment:
The deal shows engagement but lacks confirmation of decision authority and process. Risk level is high for a Commit forecast.
Buyer Intent Analysis (Using Prompt 2)
Intent Classification: Evaluating
Reasoning:
- Buyer is engaged and interested
- Pricing discussed but not agreed
- No firm decision date
- Key stakeholders (CFO, Legal) not involved
Missing Evidence of Commitment:
- Executive sponsorship beyond Ops
- Internal alignment meeting scheduled
- Verbal or written confirmation of purchase intent
Risk Signals (Using Prompt 3)
| Risk | Impact |
| No CFO involvement | High |
| Procurement & legal not engaged | High |
| Pricing resistance unresolved | Medium |
| No confirmed decision timeline | High |
Progress vs. Movement (Using Prompt 4)
True Progress:
- Problem validation with Ops
- Product fit demonstrated
Activity Without Movement:
- Multiple demos without stakeholder expansion
- Proposal sent without approval clarity
Required to Move Forward:
- CFO alignment call
- Defined approval path
- Confirmed internal deadline
Forecast Adjustment (Using Prompt 5)
Recommended Forecast Category: Best Case
Reasoning:
While interest is real, the deal lacks economic buyer validation and a confirmed decision process. Keeping it in Commit creates forecast risk.
To Re-Earn Commit Status:
- Secure CFO meeting
- Confirm procurement and legal timelines
- Get verbal confirmation of decision intent
Tips
1. Use This to Coach, Not Police
These prompts aren’t about catching reps out. They’re about raising the quality of deal conversations.
Use outputs as discussion starters:
- “What evidence do we have?”
- “What are we assuming?”
- “What risk would kill this deal?”
2. Normalize Risk Conversations
When risk is openly discussed, reps surface issues earlier. When optimism is rewarded blindly, risk hides until it’s too late.
Make it safe to downgrade deals.
3. Don’t Delegate Judgment
ChatGPT structures thinking. It doesn’t replace leadership judgment.
Read every output critically. Challenge it. Add context.
4. Focus on Patterns, Not One-Offs
The real power shows up when you see patterns:
- Deals stuck without CFO access
- Late-stage procurement surprises
- Reps overestimating buyer urgency
That’s where strategy changes—not just deal saves.
5. Use This Before the Quarter Is Lost
The best time to identify deal risk is weeks earlier than feels comfortable.
If a deal can’t withstand scrutiny early, it won’t survive pressure late.
Final Thought
Revenue doesn’t get missed in the last week of the quarter.
It gets missed quietly—weeks earlier—when optimism replaces evidence and risk goes unnamed.
Used correctly, ChatGPT becomes a mirror. It reflects what’s really happening in your pipeline—not what you hope is happening.
As a CRO, that clarity isn’t optional.
It’s your job.
