I have watched a lot of enterprise deals die. Some of them were mine. Most of them were in companies I advise or operate alongside. Almost none of them died because the product was worse than the alternative.
They died because the seller skipped qualification and started pitching. Usually because the first meeting went well and everyone got excited.
The five questions
Before anyone on my team quotes a price, I want answers to five questions. Not guesses. Answers from the buyer's mouth.
- Who signs? Not who is enthusiastic. Who has signature authority at this dollar amount, and have you spoken to them?
- What is the budget line? Does this money already exist in a line item, or does it need to be created? New budget is a 2x longer sales cycle, minimum.
- What happens if they do nothing? If the honest answer is "nothing bad," you are selling a nice-to-have and you will lose to inertia, not to a competitor.
- What is the decision process and date? Who else needs to say yes, in what order, and what is the event that forces a decision? No forcing event means no close date, which means no deal.
- Why now, and why us? If the buyer cannot articulate both in their own words, you have not earned the right to propose.
Skip any one of these and the deal looks healthy right up until it stalls at legal, or procurement, or a reorg, or a quarter-end that came and went.
Why sellers skip them
Because asking feels like friction, and a good first meeting feels like momentum. The seller does not want to be the one who slows it down. So they send the deck, send the proposal, and wait. The buyer, who was never actually qualified, goes quiet. The CRM says "proposal sent" for nine weeks.
A deal with no forcing event is not a deal. It is a conversation with a price tag.
What the product has to do with it
Less than you think. In a real enterprise evaluation, you are one of two or three finalists, and all of you can do the job. The product gets you into the room. It does not get you the signature. The signature comes from the buyer being able to defend the purchase internally, which means they need the five answers as much as you do.
When you ask the questions, you are not qualifying them. You are helping them build the case. The sellers who understand that close more and faster, with less discounting, because the buyer is doing the selling inside their own building.
The kill rule
If two of the five are unanswered after the second meeting, the deal goes to a holding pattern. No proposal. No pricing. A direct ask for the missing answers, and if they do not come, the deal is marked and the time goes to the next one. This feels brutal and it is the single biggest improvement in forecast accuracy I have seen across the companies I work with.
The deals that die on product are rare and usually fair. The deals that die on skipped questions are common and entirely avoidable.