40 sales coaching questions for 1:1s and deal reviews, by situation (2026)

Coaching questions for a deal that stalled

A stalled deal is quiet in the CRM; the questions find out whether it is also quiet with the buyer.

Bring: the last logged activity date, the days in stage, how often the close date has moved, and the buyer-side contacts on the record. A deal is stale after no logged activity for 7 days on a sales cycle under 30 days, 14 days for 30 to 90 days, or 21 days over 90, and stuck past 1.5 times the median days won deals spend in that stage. Rules of thumb; adjust them to your data.

1. "What has happened on this deal since the last activity in the CRM?" Separates quiet in the record from quiet with the buyer.
2. "What did the buyer say they would do next, and when?" Tells an agreed next step from a hoped-for one.
3. "Who on their side wants this, and who could stop it?" Surfaces single-threading and the unmet decision maker.
4. "What would have to be true for this to close on the date in the CRM?" Turns a close date into conditions you can check.
5. "If you were the buyer, what would be holding you back?" Makes the rep name the real objection.
6. "What would tell us this deal is dead?" Sets an exit condition.

Coaching questions for a discovery call that went shallow

A shallow discovery call is one where the demo started before the rep knew the buyer's problem, timeline and decision process.

Bring: the recording with the minute the demo started, or your notes, and the CRM fields for the problem, the timeline and who decides. Blank fields are the evidence. Use only calls recorded under your company's recording policy and the consent rules where your reps and buyers are.

1. "What problem is the buyer trying to solve, in their words?" An answer in your product's words means discovery did not happen.
2. "What happens to them if they do nothing?" Without a cost of waiting, nothing closes this quarter.
3. "Where in the call did you decide it was time to show the product?" Locates the moment discovery stopped, judged by the rep first.
4. "What did you learn that you did not know before the call?" A short answer means assumptions were confirmed, never tested.
5. "Which question did you want to ask and didn't?" Finds the avoided question, usually money or who decides.
6. "What would you ask first if you ran the call again?" Turns the review into the next call's plan.

Coaching questions for a rep who is behind on pipeline

A rep behind on pipeline, which is where a slump shows first, needs a diagnosis before a target, because a stopped routine, dried-up sources and deals dying at one stage each need a different fix.

Bring: deals created per week against the rep's own usual number, open pipeline against the coverage their win rate calls for (see the pipeline coverage ratio guide), and conversion by stage next to the team's.

1. "Walk me through where last month's new deals came from." Shows which sources still produce and which were dropped.
2. "What does a good prospecting day look like for you right now?" Reveals whether a routine exists before you judge its output.
3. "Which accounts have you decided not to pursue, and why?" Surfaces silent disqualification, sometimes right, sometimes avoidance.
4. "Where in the funnel are deals dying for you at the moment?" Points the coaching at one stage instead of at effort.
5. "What is taking the time that prospecting used to get?" Often one big deal or admin, a different conversation.
6. "What would it take to get back to your usual number of new deals a week?" Puts the rep's plan on the table first.

Coaching questions for a rep who is ahead and coasting

A rep who is ahead gets the least coaching and needs a different kind, one that checks the lead rests on a pipeline that keeps producing.

Bring: next quarter's pipeline coverage, deals created in the last four weeks against the rep's own usual number, and the close dates of the deals that put them ahead.

1. "What are you doing differently this quarter that got you here?" Names the behavior so it can be kept and taught.
2. "What does next quarter look like from where you sit?" Shows whether the number was built or borrowed from next quarter.
3. "Which deal would you rather I did not look at too closely?" Asked lightly; finds the soft deal inside a strong number.
4. "What would you take on if the number were not a worry?" Opens the career conversation before someone else does.
5. "Who on the team would learn the most from sitting in on one of your first calls?" Turns the lead into teaching.

Coaching questions after a lost deal, and after a won one

Run both within a week of the close. A loss review finds when the deal was really lost; a win review finds the behavior worth repeating.

Bring, after a loss: the deal timeline with its pushed close dates, the loss reason in the CRM, the last call or the email thread logged on the deal (or ask the rep for it), and the contacts on the record.

1. "When did we actually lose this?" Most deals are lost well before the closed-lost date.
2. "What did the buyer say, and what did we not hear?" Separates what was said from what the rep concluded.
3. "Who made the decision, and when did we last speak to them?" Tests multi-threading without an accusation.
4. "What did we do that they told us they valued?" Keeps the review from flattening into "we lost on price".
5. "What would we want to know before the next deal like this?" Turns the loss into a qualification question.
6. "What did you hear about our product or pricing that I should pass on?" Ends on market signal you can act on.

Bring, after a win: the deal timeline, the number of buyer-side contacts, and which stage took longest.

1. "What did we do on this one that we should do every time?" Names the repeatable behavior.
2. "Where did it nearly go wrong?" Every won deal has one, and it is honest coaching material.
3. "What made them buy now, in their words?" The trigger to look for in the next ten deals.
4. "What did the champion do for us, and how did we earn that?" Makes multi-threading concrete.
5. "What did you do here that nobody else on the team would have?" Finds the edge worth recognizing.

Coaching questions for a rep who disagrees with the plan

A rep who disagrees out loud is giving you something; the questions narrow it to one piece you can test, before anyone has to be right.

Bring: the plan on one page, the two calls or deals that made you write it, and the one number it should move within a month (for example, a dated next step on 80 percent of open deals).

1. "What do you see that I might be missing?" Shows you mean it; sometimes the rep is right.
2. "Which part of this do you agree with, and which part do you not?" Narrows it to the piece you can work on.
3. "What would convince you?" Turns a standoff into an experiment with a named result.
4. "If we ran it your way for a month, what would we measure?" Puts the rep's alternative under the same test as yours.
5. "What does doing it my way cost you?" Surfaces the real objection, often time or pride.
6. "What do we do if the number does not move either way?" Agrees the exit before the trial.

Which coaching questions to avoid (leading, yes/no, "why didn't you")

Open questions start with what, where, who, how or "walk me through", and make the rep do the reasoning. Closed questions get a yes or a no; confirm a fact with one, then go open. Three kinds do damage, leading questions, yes/no questions about a judgment, and "why didn't you", and two more waste the slot: the vague status check and the plan asked before the diagnosis.

How to use the question bank in a 1:1 or a deal review

Two questions, chosen before the meeting, each resting on one fact you brought; the first answer chooses the second question.

1. Pick two, not twenty. Choose the situation, then two questions from it, each written next to its fact. Ten make an interview.
2. Lead with the fact, then ask. "The close date has moved twice. What has to be true for it to hold?" The fact makes the question fair.
3. Ask, then be quiet. The first answer is usually a summary; the real one arrives only if you do not fill the silence.
4. Follow the answer, not the list. If deals are dying at proposal, the next question is about proposals.
5. Write the answer down, in the rep's words, in the running document from the sales 1:1 template; "what would tell us this deal is dead" becomes next week's check.
6. Turn a repeat into a plan. The same answer three weeks running is a skill, and a skill gets a coaching plan, one per rep per quarter.

Frequently asked questions