The one-on-one questions that coach a rep are the ones the rep can only answer from what the buyer said on a live deal, and that end with one thing the rep will do differently on the next call.
Status questions and coaching questions
A status question asks the rep to report. A coaching question asks the rep to look at the evidence and find the gap. "How's it going?" is a status question, and usually a sign the manager has not prepared. A better opener is "What would have to be true for this deal to close?"
- 01Ask a coaching question"What would have to be true for this deal to close?"
- 02Check the evidenceWhat did the buyer say, and who said it?
- 03Let the rep find the gap
- 04Agree one changeFor the next call
- 05Open the next one-on-one with it
Even a good question can collect opinion. A rep can answer "what would have to be true" with hope. So follow every answer with the evidence check: what did the buyer say, and who said it? If the answer is the rep's paraphrase, the gap is still open.
Telling still has a place. If a call is tomorrow and the rep has missed something important, say it plainly, then ask the rep how they will raise it on the call. The question comes after the advice, so the rep still does the planning.
The manager's skill decides whether this works. In a study of 1,246 pharmaceutical reps, the manager's coaching skill predicted goal attainment, and frequent coaching from less skilled managers was linked to worse results (Dahling et al. 2016, summarized in our Game Winning Kickoffs field study). The sales manager coaching guide sets the questions inside a weekly rhythm.
Questions for the next call
- "What does this call have to produce for the deal to move?"
- "What has the buyer told you the problem costs them, in their words?" (the current state and the gap, in Gap Selling terms)
- "Who signs, and have they been on a call?" (the economic buyer, in MEDDPICC terms)
- "What will you ask in the first five minutes?"
- "What would make you leave the call knowing it went well?"
Questions about the last call
- "What did the buyer say that surprised you?"
- "Where did they give you a long answer, and what did you ask next?"
- "What did you agree as the next step, and did the buyer say it back?"
- "If you ran that call again, what is the one change you would make?"
- "When will we see that change, and on which deal?"
Write the answer to the last one down and open the next one-on-one with it.
Questions for a discovery call coming up
- "What do you already know about the problem, and who told you?"
- "Which question will tell you whether this is worth a second meeting?"
- "If the buyer says the problem is 'a bit of a pain', what do you ask next?"
- "Who else feels this problem, and how will you find out?"
- "What do you want the buyer to agree to do before the end of the call?"
Discovery is where a rep is most tempted to fill silence with the pitch. Asking them to say the follow-up question out loud, before the call, is often enough to stop it.
Questions for a stalled deal
- "When did the buyer last do something, and what was it?"
- "What changed on their side since the deal was last moving?"
- "Who is the next step waiting on: them, or you?"
- "If the buyer did nothing at all, what would happen to them?"
- "What is one conversation that would tell you whether this deal is still alive?"
A stalled deal invites a status update dressed as a story. Keep pulling it back to the last buyer action and the next one.
Questions for late-stage and pricing conversations
- "What are the remaining steps on the buyer's side, and who owns each one?"
- "Whose date is the close date: theirs, or ours?"
- "What will you say if they ask for a discount on the call?"
- "What has the person who signs heard about the cost of the problem, from their own team?"
- "What would make this slip into next quarter, and what can you do about it this week?"
Late in a deal, reps tend to protect it by talking less about it. These questions ask for names and dates, which are easy to check on the next call.
Newer reps and tenured reps
The questions are the same; the follow-up changes. A newer rep often has the evidence and does not know it matters, so ask them to quote the buyer and then ask what that quote tells them. A tenured rep usually knows what matters and skips it from habit, so ask what they did differently from their usual approach, and what they would expect a newer rep to ask. In both cases, the rep does the finding and the manager holds the question.
Questions about skill and growth
Once a month, step back from the single deal.
- "Across your last few calls, where do you lose the thread?"
- "Which deal are you avoiding, and why?"
- "What did the last deal you lost teach you that you have used since?"
- "Which part of the method do you find hardest to do on a live call?"
- "What would you like to be better at by next quarter, and what would show it?"
The answer to the last one becomes the skill the deal questions keep coming back to.
Questions about the rep, beyond the deal
Some weeks the deal is fine and the rep is not. A rep who is stretched, stuck on an internal blocker or losing interest will not take much from the evidence check. Keep a few minutes for questions about them, and ask at least one every week.
- "What took more of your time this week than it should have?"
- "What is waiting on someone inside our company, and who?"
- "Which part of the job are you enjoying least right now?"
- "What would make next week easier?"
- "Is there anything you want me to hear before we talk about deals?"
These questions work best at the start of the meeting or in the slot for blockers, and they need a different follow-up. The aim is to remove an obstacle the manager can remove, such as a pricing approval stuck with finance or a territory question nobody has answered. If the answer is about workload or something outside work, listen, agree what the manager will do, and leave deal coaching for another day.
Follow-ups when the first answer is thin
The first answer to a coaching question is often the rep's summary. These follow-ups get to what the buyer said.
| The rep says | Ask next |
|---|---|
| "They're very engaged." | "What did they do that shows it?" |
| "Budget shouldn't be an issue." | "Who said that, and in what words?" |
| "I think the CFO is on board." | "Has the CFO been on a call? What did they say?" |
| "The call went well." | "What did the buyer agree to do next, and by when?" |
| "They just need to get it through internally." | "Through whom, and what will that person need to see?" |
| "I'd change my opening." | "To what? Say it the way you will say it." |
One follow-up is usually enough. If the second answer is still a summary, that is the gap, and the next call's job is to close it.
"How confident are you?" versus "Who approves?" (illustrative)
A manager asks about a deal at proposal stage: "How confident are you on this one?" The rep says 80%. That is status, and the meeting moves on.
Same deal, different question: "Who has to approve the spend, and what have they said?" The rep pauses. The operations lead said finance "will need to see it," and nobody from finance has been on a call. The rep agrees to ask the operations lead on Thursday what finance will want to see, and to propose 15 minutes with that person. The next one-on-one opens with whether it happened.
A 30-minute one-on-one built on these questions
Read the CRM before the meeting so the time goes on coaching. Then:
| Minutes | What happens | The question |
|---|---|---|
| 0 to 3 | Last week's commitment | "Did the change happen, and what did the buyer say?" |
| 3 to 15 | One deal in depth, chosen by the rep | Two or three from the lists above, each followed by the evidence check |
| 15 to 25 | The next call on that deal | "What will you ask in the first five minutes?" Then have the rep say it. |
| 25 to 28 | Anything blocking the rep | "What do you need from me this week?" |
| 28 to 30 | One commitment | "When will we see that change, and on which deal?" |
If a second deal needs attention, book it as its own conversation. Two deals in one 30-minute slot usually means both get status questions.
One deal across three one-on-ones (illustrative)
This example is illustrative. Jordan sells scheduling software and brings a deal with Ferncliff Logistics, a regional freight company, to a one-on-one with their manager, Sam.
Week one. Sam asks, "What has the buyer told you the problem costs them?" Jordan says dispatch is "a mess". Sam asks who said that. It was Jordan's summary of a call with the dispatch lead. The commitment: on the next call, ask the dispatch lead what a missed pickup costs, and write down the answer in the buyer's words.
Week two. Sam opens with the commitment. Jordan asked, and the dispatch lead said each missed pickup means a re-booked truck and an apology call to the customer. Sam asks, "Who signs, and have they been on a call?" Jordan thinks the operations director signs. Nobody from that team has spoken. The commitment: ask the dispatch lead to bring the operations director to the next call, and prepare one question for that person.
Week three. The operations director joined for twenty minutes and asked about rollout time. Sam asks, "What did you agree as the next step, and did the buyer say it back?" Jordan agreed to send a rollout plan, and the director said the team would review it by Friday. The commitment for next week: open the next call by asking what the director's team said.
Three one-on-ones, three questions, and the deal moved from a rep's impression to the buyer's own description of what a missed pickup costs them and an approver who has been on a call. None of the meetings needed the forecast number.
Mistakes that turn coaching back into status
- Asking five deals' worth of questions in one meeting. Each deal gets a sentence, and every sentence is status. Pick one deal.
- Answering the question for the rep. When the rep pauses, the manager fills the gap with what they would do. The pause was the coaching.
- Skipping the evidence check. A confident answer with no buyer words behind it closes nothing.
- Ending without a commitment. A good conversation that names no change for the next call is forgotten within days.
- Not opening with last week's commitment. If the manager never checks, the rep learns that commitments are a way to end the meeting.
Using the questions every week
The sales manager coaching guide covers the full weekly job. How to run a one-on-one on a deal gives the procedure, and the one-on-one sales meeting template has the agenda. Our docs show how a coaching conversation runs in the product.
Pick two questions from each list and use them for a month before adding more. If you want the evidence check prepared before each one-on-one, Bryce coaches managers on the 1:1 and the forecast, starting from what each deal is missing.
FAQ
How many questions should a manager ask in a sales one-on-one? Two or three, on one deal. Follow each with "what did the buyer say?" and the gap usually shows. End on the commitment question so the rep leaves with one change for the next call.
What is the difference between a status question and a coaching question? A status question asks for a fact the manager could read in the CRM, such as the close date or the rep's confidence. A coaching question makes the rep look at what the buyer said and find what is missing. Get status before the meeting so the time goes on coaching.
How often should a manager hold one-on-ones with sales reps? Weekly, for most front-line teams, at a fixed time. Weekly gives each commitment one buyer conversation to happen in before the manager checks it. Canceling one-on-ones in a busy week tends to cost the follow-through that makes them work.
What if the rep has no deal worth discussing? Then the one-on-one is about pipeline. Ask which accounts look like the deals the rep has won, what they will do this week to start a conversation with one of them, and what they will say in the first message. The commitment is the same shape: one action, on one account, by a date.
Should the rep or the manager set the one-on-one agenda? The rep picks the deal; the manager keeps the shape. A rep who brings the deal with a meeting coming up gets help they will use that week. The manager makes sure the session ends on one change and opens the next time by checking it.