The job
A one-on-one on a deal is the ten to fifteen minutes inside a manager's weekly one-on-one where the manager and rep work one live opportunity to its next buyer conversation. The manager runs it, the rep does most of the talking, and it ends with the rep saying, out loud, what they will say to a named person and when.
- 01The rep tells the dealFrom the buyer's side, uninterrupted
- 02Walk the ladderThe evidence behind each rung
- 03Name the one missing thing
- 04The rep says the opening lineOf the next conversation, out loud
- 05Check the month's skillOn this deal
- 06Write the commitmentIn the rep's words, with a date
The rest of the one-on-one (last week's commitments, the number, the rep's skill for the month) is laid out in our one-on-one sales meeting template. This piece is the deal block in detail. It sits inside the cadence described in our sales manager coaching guide.
Why one deal and why this way: the manager's coaching skill matters. Across 1,246 pharmaceutical reps, manager coaching skill predicted goal attainment, and frequent coaching from less skilled managers was linked to worse results (Dahling et al. 2016). The questions below are the skill.
The evidence ladder
Walk the deal from the top. The first rung with no buyer evidence is the deal's real stage, whatever the CRM says.
| Rung | Buyer evidence that earns it | What usually stands in for it |
|---|---|---|
| Problem | The buyer described the problem in their own words | The rep's account research |
| Cost | A named person put a number on the problem | "It's a big pain for them" |
| Fit | The buyer said which of their criteria the solution meets and which it misses | A demo with no objections |
| Signer | The person who signs has been on a call and said what happens next | "My champion is taking it upstairs" |
| Path | The buyer walked the rep through their approval steps, with names | "It's with procurement" |
| Date | A dated step sits on the buyer's calendar | A close date the rep picked |
Questions for each rung
Use one or two of these per rung in step 3. Each asks for something the buyer said or did.
| Rung | Questions to ask the rep |
|---|---|
| Problem | "How did the buyer describe the problem, in their words?" "Who else at the buyer has it?" |
| Cost | "What did they say it costs them, and who said it?" "What happens if they leave it another quarter?" |
| Fit | "Which of their criteria did they say we meet? Which did they say we miss?" "What did they compare us with?" |
| Signer | "Who signs, and have they been on a call?" "What did the signer say happens next?" |
| Path | "Who walked you through the approval steps, and what are they, with names?" "What did the last similar purchase go through?" |
| Date | "What is on the buyer's calendar, and who put it there?" "What event on their side makes this date matter?" |
When the rep answers with their own view ("I think they're close"), ask the same question again with "what did they say?" in front of it. Two tries is enough. If the second answer is still the rep's view, that rung has no evidence, and you have found the stage.
How to run it: seven steps
1. The rep picks the deal; the manager preps for fifteen minutes
The rep chooses the deal the evening before: the one that would change their number most if it moved a rung. The manager reads it as far as the last buyer action and prepares one question for the first rung that looks thin.
What good looks like: the manager walks in knowing which rung they will test first.
2. The rep tells the deal from the buyer's side, uninterrupted
Ask: "Tell me this deal from the buyer's side. Who has the problem, what did they say it costs, who signs, and what did they last do?" Then stay quiet for three minutes.
What good looks like: the rep quotes people. If the story is all about the rep's activity ("I sent the proposal, I followed up twice"), that tells you the buyer side is thin.
3. Walk the ladder and ask for the evidence behind each rung
Go rung by rung. For each one: "What did they say? Who said it? When?" Accept quotes, emails and calendar invites. Treat "they're keen" as a forecast.
What good looks like: within five minutes both of you agree on the first rung with no evidence. That is the real stage.
4. Name the one thing the deal is missing
Say it in a sentence and write it down. "We don't have a number on the problem from anyone at the buyer." One gap. If you find two, take the higher rung; the lower one is usually fixed on the way.
What good looks like: the rep agrees with the sentence. If they argue, go back to step 3 on that rung.
5. The rep says the opening line of the next conversation
Ask: "Who do you need to speak to, and what's the first thing you'll say?" The rep says it out loud as if the buyer were on the line. Then give the buyer's likely reply once, and let the rep answer it.
What good looks like: a line that names something the buyer said and asks for one specific thing. "You said the month-end close takes your team a week. Can you put a number on that before we meet your CFO?"
6. Check the month's skill on this deal
If the rep's skill this month is putting a number on the problem, this deal is the evidence: did they ask, what did the buyer say? Transfer research is consistent that what happens back at work predicts whether a skill gets used (Saks & Belcourt 2006; Blume et al. 2010). The live deal is where you see it.
What good looks like: one sentence in the record on whether the skill showed up on this deal.
7. Write the commitment in the rep's words, with a date
The rep says what they will do and by when; the manager writes it down and reads it back. Next week's one-on-one opens by checking it against what the buyer said.
What good looks like: "Thursday call with Ana: ask for the cost of the close, and ask for 20 minutes with the CFO before the 14th."
Worked example
Illustrative. The rep, account and figures are fictional.
Sam's deal is a $75,000 opportunity with a regional insurer, marked "proposal" in the CRM.
Step 2. Sam tells it: the claims director, Ana, has a backlog problem; the demo went well; the proposal went out last week; Ana said she would "socialize it internally".
Step 3. The manager walks the ladder. Problem: yes, Ana described the backlog in her own words on the first call. Cost: "What did she say the backlog costs?" Sam: "She said it was significant." No number. The real stage is problem, two rungs below where the CRM puts it.
Step 4. The gap, written down: "Nobody at the insurer has put a number on the backlog."
Step 5. Sam's first try: "Just checking in on the proposal." The manager asks for a line that uses something Ana said. Second try: "Ana, you said the backlog was significant. When your CFO reads this proposal, what number will she want to see next to it?" The manager plays Ana: "I'd have to pull that together." Sam: "Can we do it together on our next call? Fifteen minutes, your numbers."
Step 6. Sam's skill this month is a number on the problem. On this deal, he missed it on the first call. One line in the record.
Step 7. Commitment: "Next call, 15 minutes with Ana to build the backlog cost from her numbers; ask who besides her sees the proposal."
Eleven minutes. Next week, the first block checks whether Ana gave a number.
The manager's prep checklist
Step 1 gives the manager fifteen minutes. A list that fits in them:
- Open the deal and read the last buyer action, with its date. Ignore the rep's notes for now.
- Check the CRM stage against the ladder. Mark the first rung where the record shows no buyer evidence.
- Pick one question for that rung from the table above, and write it at the top of your notes.
- Read last week's commitment for this rep and whether the buyer did what the rep hoped.
- Note the rep's skill for the month, so step 6 takes one sentence.
- Decide the buyer reply you will give in step 5, based on what this buyer has said so far.
Done this way, the manager walks in with one question and one buyer reply, which is all the block needs. Anything more tends to turn into the manager solving the deal. If the prep shows the deal has no thin rung at all, ask the rep to bring a different one; a deal with evidence on every rung needs a closing plan more than a coaching block.
Where it goes wrong
The manager solves the deal. Former top reps tend to take over. The rep leaves with the manager's plan and no practice saying it. Keep the rep talking in steps 2 and 5.
Several deals in one block. Four deals in fifteen minutes is a pipeline review. One deal, worked to a line.
Feelings accepted as evidence. "She loves it" is not a rung. Ask what she said, and when.
No line said out loud. A plan that stays in the manager's notes is easy to agree with and hard to deliver. The rep should hear themselves say it.
The commitment is never checked. If next week's one-on-one does not open on it, the rep learns that commitments are optional.
Doing this on every deal
The one-on-one covers one deal a week. A rep with a dozen open deals needs the same questions on the other eleven, and no manager has the hours. Our AI sales experts cover the other eleven. The rep brings any deal to Caty on a call, by voice or video, and she walks the same ladder in the team's own method, names what is missing and helps plan the next conversation. Gap Selling teams get the same from Keenan, and ValueSelling Framework® teams from Val. The expert remembers the deal next week. Typing is there for when a rep cannot talk.
The manager keeps the one-on-one. Before it, fifteen minutes with Bryce, the manager coach, gives one gap, one piece of evidence and one opening line for the meeting (manager coach docs). At the end, the manager can send the rep back to their coach with a specific ask, such as "show me what quantifying the backlog sounds like on the insurer deal", so the next session picks up where the one-on-one stopped (the coaching conversation).
Sam's deal got a cost question and a CFO ask in eleven minutes. Doing that every week for every rep is a rhythm problem, covered in how to set a sales coaching cadence and how to coach every rep when a manager has eight.
FAQ
How do you run a one-on-one with a sales rep?
Run it weekly for 30 minutes in five blocks: last week's commitments, the number, one deal, the rep's skill for the month, and next week's commitments. In the deal block, the rep tells the deal from the buyer's side, the manager asks for evidence rung by rung, and the rep says the opening line of the next buyer conversation out loud.
What should a manager ask a sales rep about a deal?
Ask for the buyer's side: who has the problem, what they said it costs, who signs, what the buyer last did and when. For each answer, ask who said it and when. The first question the rep cannot answer with something the buyer said or did marks the deal's real stage.
How many deals should you cover in a one-on-one?
Cover one deal in a one-on-one, worked properly, in about ten to fifteen minutes. Covering several deals turns the one-on-one into a pipeline review and leaves no time for the rep's skill. Other deals go to the weekly pipeline review or to a separate deal review.
How do you stop a sales one-on-one becoming a status update?
Ask only for buyer evidence on one deal, and end on the rep's next line to a named buyer with a date. Status questions ("where is it, when will it close?") belong in the pipeline review. Open each one-on-one by checking last week's commitment against what the buyer said.
What if the rep cannot answer the evidence questions?
If the rep cannot answer the evidence questions, that gap is the finding. The first rung without buyer evidence is the deal's real stage, and the next conversation should get that evidence. Write the gap in one sentence, have the rep say the line that asks for it, and check next week whether the buyer answered.
Should the manager play the buyer in a one-on-one?
The manager should play the buyer in a one-on-one once, briefly. After the rep says the opening line, the manager gives the buyer's most likely reply and the rep answers it. That takes a minute and shows whether the line survives contact. For longer practice, the rep's coach can build a roleplay from the deal and debrief it before the call.