In our view, the useful deal review questions are the ones aimed at what the deal is missing. Ask all thirty classic questions and you get thirty confident answers; ask the handful on the gap and you learn whether the deal is real. The table below sorts the questions by gap, with the answer that should satisfy you and the answer that should not. It sits under our guide to deal coaching; for the short definition, see deal review.
The question bank, sorted by the gap
First find the gap. Walk the deal from the top row down and stop at the first row where the rep cannot point to something the buyer said or did: a quote, an email, a calendar entry. That row is the deal's real stage, whatever the CRM says. Then ask that row's questions.
| What the deal may be missing | Questions to ask | Strong answer | Weak answer |
|---|---|---|---|
| The problem in the buyer's words | What did they say is wrong, word for word? Who said it? What happens if nobody fixes it? | A quote, a name and a date: "Priya, ops lead, call 2: 'we miss one in five delivery windows.'" | "They have a lot of inefficiency in operations." |
| A cost on the problem | What number did the buyer put on it? Who gave it? Would their boss recognize that number? | "Priya said the missed windows cost them about $40k a month in credits." | "It's a big problem for them, easily six figures." (The rep's estimate.) |
| Criteria the buyer has stated | Which of their criteria did they say we meet? Which did they say we miss? Who wrote the criteria? | "Their IT lead said single sign-on is a must and we passed the security review on the 12th." | "The demo went really well." |
| The person who signs | Who signs? When was that person last on a call? What did they ask? | "Their COO joined the second half of Tuesday's call and asked about rollout time." | "Our champion is close to the COO." |
| The approval path | Walk me through the steps from today to a signature, in order. Who owns each? Where are we now? | "Ops recommends, Finance approves over $50k, Legal reviews; Priya sent me the policy." | "It's with procurement." |
| A dated buyer step | What is on the buyer's calendar that only makes sense if they are buying? Who put it there? | "Their Finance review is booked for the 18th and Priya sent the invite." | "They said they want to move quickly." |
| A second thread | Who else at their end loses if this does not happen? When did you last speak to them? | "The regional manager who fields the complaints; we spoke last Thursday." | "Everything goes through Priya." |
Two questions belong on every deal. Open with "What has changed since the last conversation?" A rep who answers "nothing" has not spoken to the buyer. Close with "Why will this deal not close?" The answer is usually the gap the rep already suspects, and reps find it easier to give than an answer to "will it close?", because it lets them name the risk without admitting the deal is weak.
The rows map onto any method. MEDDPICC teams will see metrics, decision criteria, economic buyer and decision process; Gap Selling teams, current state and its cost; ValueSelling Framework® teams, the business issue and the person with the power to buy (ValueSelling). Ask in your method's words and keep the strong-answer standard.
Questions on timing, competition and buying history
The gap table covers the buyer evidence most methods ask for. Four other areas change how a deal should be worked, and each has its own weak answer to listen for.
| Area | Questions to ask | Strong answer | Weak answer |
|---|---|---|---|
| Why now | What happens on their side if they decide next year? What event set this date? | "Their carrier contract ends on 30 June, and they have to re-tender if nothing replaces it." | "They're keen to get it done this quarter." |
| Competition | Who else are they talking to? If they do nothing, what do they keep doing? Who would we lose to? | "One other vendor, and the spreadsheet the ops team built is the real alternative." | "No competition, they love us." |
| Buying history | Have they bought something like this before? Who signed it, and how long did approval take? | "They bought routing software two years ago; the CFO signed after a six-week legal review." | "Should be straightforward." |
| The price | Has the person who signs seen the number? What did they say? | "The COO saw the quote on Tuesday and asked for a two-year option." | "The champion says budget isn't an issue." |
"No competition" needs a follow-up every time. The buyer always has an alternative, even if it is the way they work today, and a spreadsheet that costs nothing is a hard thing to beat. A first-time buyer for this kind of product carries its own risk: the people inside may not know the approval path either, so ask who signed the last comparable purchase and how long it took.
How to use it
Use the list to find the deal's one gap, then spend the review on that row's questions.
- Open with what changed. One question, one answer, before anything else.
- Find the gap. Start at the top row and ask for the evidence for each, briefly. Stop at the first row where the answer sounds like the weak column.
- Ask that row's questions in full. Push until you get a quote, a name, a date or an honest "I don't know".
- Name the gap in one sentence about the buyer. "Their COO has never heard the $40k number."
- Plan the conversation that fills it. Who, why they will take it, the opening line, the likely pushback and the reply.
- Hear the opening line. The rep says it out loud. If it starts with "just checking in", go again.
- Calendar the conversation and the next review. Next time, start with what the buyer said.
That fits in a 20 to 30 minute review. The full agenda is in how to run a deal review, and the one-page form is the deal review template.
A filled-in example (illustrative)
The account, people and numbers are fictional.
- 01What changed?A revised quote with a two-year term
- 02Find the gapProblem, cost, criteria pass; the signer does not
- 03Ask the signer questionsThe CFO has never been on a call
- 04Name the gap in one sentence
- 05Plan the next conversationOpening line said out loud
Dana manages Marcus. His deal with a regional logistics firm sits at Negotiation in the CRM: $85,000, closing in three weeks.
What changed? "They asked for a revised quote with a two-year term."
Finding the gap. Marcus quotes the operations lead from call one on the problem, and on cost: "She said re-delivery costs them about $25k a quarter." Criteria: "IT signed off the integration on the 3rd, I have the email." The signer: Marcus pauses. "The CFO. She hasn't been on a call. Our champion says she's supportive." That is the weak column, so the real stage is the signer row.
The signer questions. Who signs? The CFO. When was she last on a call? Never. What did she ask? Marcus does not know. What does she know about the $25k? "I assume the ops lead told her."
The gap, in one sentence. The CFO has never heard the cost of the problem from anyone on our side, and a two-year quote is going to land on her desk without it.
The next conversation. With the operations lead, tomorrow. Opening line, said out loud: "Before the revised quote goes to your CFO, can we spend 15 minutes on how she'll want the $25k shown?" Likely pushback: "I'll just forward it." Reply: "Happy for you to. Can I draft the one page she'll ask for and join for ten minutes if she has questions?" Marcus wants to leave with a date for the CFO, or agreement on the one page.
Dana asked nine questions. Four were on the signer row.
Questions to stop asking
Some questions fill the review with talk and leave the deal where it was. Five to drop, and what to ask instead:
| Stop asking | Why | Ask instead |
|---|---|---|
| "Is the close date right?" | The rep will say yes | "What happens on the buyer's side on that date?" |
| "What stage is it in?" | The CRM already says | "What did the buyer do that put it in this stage?" |
| "Do we have a champion?" | Invites a name with no evidence behind it | "What has this person done for the deal that cost them something?" |
| "What's the probability?" | A percentage is a feeling | "What would have to be true for this to close this quarter?" |
| "Did you follow up?" | Counts activity and says nothing about progress | "What did the buyer agree to on the last call?" |
The rule behind the table: if the manager can check the answer in the CRM, do not spend review time on it.
Three ways teams misuse deal review questions
Asking every question on every deal. A thirty-question list turns the review into an interrogation. Find the gap first and ask only that row's questions.
Accepting the weak column. "Our champion is close to the CFO" sounds like an answer. It is the rep's belief. Ask for the quote, the email or the calendar entry, and if there is none, write the gap down and plan the conversation.
Stopping at the gap. The meeting ends with "get to the CFO", which is a task with no plan. The review ends only when the rep has said the opening line of the next buyer conversation out loud.
Deal review questions and pipeline review questions
A deal review and a pipeline review need different questions, because they answer different things. A deal review takes one deal and asks what it is missing and what the rep will do next. Everything above is for that meeting. A pipeline review looks across all of a rep's deals and decides which belong in the forecast and which need a deal review.
Pipeline review questions are shorter and comparative. Which deals moved since last week, and what did the buyer do to move them? Which deals have gone two weeks without a buyer conversation? Which close dates fall before the buyer's own approval step? Each deal gets a minute, and any deal that fails one of those questions leaves the pipeline meeting for a deal review of its own.
Running a pipeline review deal by deal is the usual way the two get mixed up: the hour runs out at deal six, and the deals at the bottom of the list never get looked at. The difference between a deal review and a pipeline review is covered separately, and the pipeline review questions have their own list.
Asking these questions on every deal
Few managers have thirty good minutes for every deal that needs one, and skill matters too: across 1,246 pharmaceutical reps, managers' coaching skill predicted goal attainment, and frequent coaching from less skilled managers was linked to worse results (Dahling et al. 2016, via our kickoff field study).
Caty runs this review as a call. The rep brings the deal and talks it through out loud; Caty walks the rows, asks the questions on the first one without evidence, pushes past the weak answer and has the rep say the opening line of the next conversation, in the team's own methodology. Gap Selling teams work the deal with Keenan, ValueSelling Framework® teams with Val. A rep who cannot talk at that moment can type. The manager gets a read across the team from Bryce, the expert that coaches managers, including which deals carry buyer evidence. To run the rows on one of your own deals, talk to us, or read how deal execution works.
FAQ
What are the most important questions to ask in a deal review?
The most important questions are the ones on the deal's first missing piece of buyer evidence. Open with "what has changed since the last conversation?", find the first gap (often the signer or the cost of the problem), ask the questions for that gap until you get a quote, name or date, then plan the next buyer conversation.
How many questions should a manager ask in a deal review?
Usually eight to twelve, most of them on one gap: one opener, a quick pass to find where the buyer evidence stops, then that row's questions in full. Asking every question on a long list buries the one gap that matters this week.
What is a weak answer in a deal review?
A weak answer is the rep's belief stated as fact, with no quote, email or date behind it. "The champion is bought in", "the demo went well" and "it's with procurement" are weak. A strong answer names who said what and when, so the manager can tell evidence from hope.
Should deal review questions change by sales stage?
They should change by the gap, which is often different from the CRM stage. A deal marked Negotiation with no signer on record needs signer questions. Find the first row with no buyer evidence and ask that row's questions; the CRM stage tells you where the rep thinks the deal is.