◆   Field Dispatch #001 — Free Sample   ◆   Section 01 of 04   ◆
Dispatch #001  —  Professor Pipeline

Deal Autopsy —
Section 01 of 04

The full dispatch contains 38 questions across four sections. What follows is Section 1 in its entirety — 10 questions, each with its mechanism, what it reveals, and the red flags that mean a deal is already dead.

Read it. If you recognise the problems, the remaining 28 questions are in the full dispatch.

Free sample — no email required

Deal Autopsy

Run on every deal over $50,000. Run it before you include it in a forecast. Run it when your instinct says the rep is lying to themselves. Ten questions. Each one is a scalpel.

Q01 / Deal Autopsy
What is the exact evidence — not the rep's feeling — that the economic buyer has approved budget for this quarter?
Why it works

Reps conflate "they seemed interested" with "budget is approved." These are not the same thing. One is a conversation. The other is a purchase order. The forecast only cares about the second one.

What the answer reveals

If the rep cannot name a specific conversation, email, or internal document in which the economic buyer confirmed available budget, the deal is not in this quarter. It is in the rep's optimism.

Red flags
  • "They said it shouldn't be a problem"
  • "We're expecting approval next week" (for the third consecutive week)
  • "Budget isn't really their concern at this stage"
  • Silence followed by a change of subject
Q02 / Deal Autopsy
When was the last time the champion sent you something you didn't ask for?
Why it works

A real champion sells internally on your behalf. They forward your deck without being asked. They CC you on emails you shouldn't have seen. A passive contact is not a champion. They are a friendly face with no power and no skin in the game.

What the answer reveals

If the answer is "never" or "I'm not sure," you do not have a champion. You have a contact. Contacts do not get deals done.

Red flags
  • "They're very supportive when we speak"
  • No unsolicited communication in the last 30 days
  • Champion has changed roles since the deal started
Q03 / Deal Autopsy
What is the compelling event — not our close date — that makes this quarter the right quarter for them to buy?
Why it works

Close dates in CRMs are almost always derived from the rep's quota deadline, not from the customer's urgency. A deal without a compelling event on the customer side has no reason to close this quarter. The rep's target is not a compelling event.

What the answer reveals

If the rep cannot name a specific customer-side driver — a contract expiry, a board deadline, a product launch, a cost that starts accruing — the close date is fiction. It is a number in a field that makes the forecast look full.

Red flags
  • "They want to get it done before year end"
  • "It's been in the pipeline since Q2"
  • "They're motivated" (without a reason why now)
Q04 / Deal Autopsy
Who else is in the evaluation — and have we spoken to all of them?
Why it works

Enterprise deals die in rooms the rep has never been in. A stakeholder who has never been engaged is a veto waiting to happen. The rep who believes the deal is won because their contact is enthusiastic has not mapped the buying committee. They have mapped the contact.

What the answer reveals

If the rep can only name the person they speak to — not the legal, procurement, IT, or finance stakeholders who will be involved in a decision of this size — the deal is single-threaded. Single-threaded deals slip. They do not close on time.

Red flags
  • "I mostly deal with [name]"
  • No procurement or legal contact identified
  • "They said they'll handle the internal sign-off"
Q05 / Deal Autopsy
What does the competition look like in this deal — and how do we know?
Why it works

Reps underreport competitive presence because acknowledging competition makes the deal feel less certain. The customer who says "we're not looking at anyone else" is frequently looking at two other vendors. The rep who believes them is building a forecast on a courtesy.

What the answer reveals

If the rep's competitive intelligence comes entirely from the prospect's self-reporting, it is unreliable. Real competitive intelligence comes from procurement language, evaluation timelines, and the questions the prospect is asking.

Red flags
  • "They told us we're the only ones they're talking to"
  • RFP received with unusual specificity (written around a competitor)
  • Evaluation timeline suddenly extended without explanation
Q06 / Deal Autopsy
Has legal or procurement been involved yet — and if not, why not?
Why it works

Legal and procurement involvement is a buying signal. It means the organisation has decided to proceed far enough to allocate internal resource. The absence of legal and procurement in a deal marked as close-ready means either the organisation has not decided, or the deal has not reached the people who actually process purchases.

What the answer reveals

If legal and procurement are not engaged and the deal is in the current quarter's committed forecast, the timeline is wrong. Legal review alone can add four to eight weeks. Nobody told the CRM.

Red flags
  • "We haven't got to that stage yet" (with two weeks left in the quarter)
  • "Our champion is handling the internal process"
  • No MSA or SOW in progress
Q07 / Deal Autopsy
What has the customer said no to in this deal — and what did we learn from it?
Why it works

A deal where the customer has never pushed back is not a deal. It is a series of pleasant conversations. Real buying processes involve objections, scope questions, and commercial friction. A prospect who has agreed with everything has not bought. They have been polite.

What the answer reveals

The absence of objection in an enterprise deal is a red flag, not a green one. It means either the evaluation is not serious, or the rep has not asked the questions that would surface resistance. Either way, the deal is not as solid as the forecast suggests.

Red flags
  • "They've been really positive throughout"
  • No documented objections or scope challenges in the CRM
  • "It's been a smooth process"
Q08 / Deal Autopsy
What is the last concrete next step — with a date, an owner, and a deliverable — that was agreed with the customer?
Why it works

Deals without next steps are not in motion. They are in memory. A rep who describes the deal's progress in terms of conversations rather than agreed actions has lost control of the process. The customer is not buying. They are being waited on.

What the answer reveals

If the last agreed next step is more than two weeks old, or cannot be described with a specific date and deliverable, the deal has stalled. The forecast entry is describing a deal that was in motion, not a deal that is in motion.

Red flags
  • "I'm following up with them this week"
  • Last customer-side action: more than 14 days ago
  • "They're reviewing it internally"
Q09 / Deal Autopsy
If this rep left tomorrow, what would happen to this deal?
Why it works

Deals that live entirely in the rep's head are fragile. If the institutional knowledge about the deal — the relationships, the history, the objections, the internal politics — cannot be reconstructed from the CRM and documented communications, the deal is one person deep. One person deep is a risk the forecast has not priced in.

What the answer reveals

If the honest answer is "it would probably die," the deal is not an organisational asset. It is a personal one. The forecast is treating personal assets as organisational certainties.

Red flags
  • CRM notes sparse or absent
  • All customer relationships mediated through the rep
  • "I know this account really well" (undocumented)
Q10 / Deal Autopsy
Has this deal slipped before — and if so, what is different this time?
Why it works

A deal that has moved its close date once will move it again unless the underlying reason for the slip has been addressed. Reps rationalise slippage as external — budget cycles, stakeholder changes, procurement delays. The question is whether anything structural has changed, or whether the new close date is the old close date plus 90 days.

What the answer reveals

If the deal has slipped more than once and the rep's answer to "what's different" is a feeling rather than a fact, the deal will slip again. The forecast entry is a comfort blanket with a close date.

Red flags
  • Close date moved two or more times
  • "We're really close this time"
  • Same deal, same stage, different quarter
End of free sample — Section 01 of 04

The remaining 28 questions are in the full dispatch.

Three more sections. A pipeline health scan. A forecast reality check. A Monday morning operating rhythm. A scoring rubric. Four printable worksheets.

02 Pipeline Health Scan
03 Forecast Reality Check
04 Monday Morning Execution
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