Coaching a rep on a deal is a 20-minute call in which the manager helps the rep find what one live opportunity is missing and plan the next conversation with the buyer. The frontline manager runs it, usually weekly, on the deal where a conversation this week will change the outcome.
This piece is the procedure for that one call. For the wider practice (choosing the deals, staging the pipeline, mutual action plans and stalled deals), see our guide to deal coaching.
The job: one deal, one call, one next conversation
The output of a deal coaching call is a conversation the rep will have with a named person at the buyer, planned well enough that the rep could have it an hour later. Everything in the 20 minutes serves that.
Three ground rules keep the call on that job:
- One deal. If the rep wants to cover three, the manager picks one and books the others.
- Evidence over opinion. A claim about the deal counts when the rep can point to something the buyer said or did.
- The rep talks first and most. The manager's main tool is a question.
The call is held out loud, on the phone, Zoom or video. A typed update lets a rep describe a plan they could not say out loud. Saying it shows the gap in seconds.
Before the call: two minutes of prep
The rep brings the deal, the manager brings one question. Prep is short on purpose; a call that needs an hour of preparation will not happen every week.
The rep should have the last two buyer touchpoints open (an email, call notes or a recording) and know who they last spoke to. The manager should look at the CRM stage and close date and write down one question the record cannot answer, such as "Who signs?"
The 20-minute deal coaching call, step by step
Step 1. The rep tells the deal (minutes 0 to 4)
Say: "Tell me this deal from the buyer's side. Who has the problem, what did they say it costs, who decides, and what happened last?"
- 01The rep tells the dealMinutes 0 to 4
- 02Find the real stageMinutes 4 to 9
- 03Name the one gapMinutes 9 to 11
- 04Choose the conversationMinutes 11 to 13
- 05Say the opening out loudMinutes 13 to 18
- 06CommitMinutes 18 to 20
Do: listen without interrupting. Write down every claim that sounds like a belief: "they love it", "it's a priority", "the champion is strong".
Good looks like: the rep names people and quotes them. Weak looks like product features and adjectives.
Step 2. Find the real stage (minutes 4 to 9)
Say: for each belief you wrote down, "What did they say or do that tells you that?"
Do: walk the deal from the top. Has the buyer described the problem in their own words? Put a number on it? Said which of their criteria the solution meets? Has the person who signs been on a call? Has the buyer explained the approval steps? Is there a dated buyer step on the calendar? The first one without evidence is the deal's real stage. Our deal review template lays this out on one page.
Good looks like: the rep finds the evidence or admits it is not there. Both are wins. A rep who says "I'm not sure, let me check" is telling the truth.
Step 3. Name the one gap (minutes 9 to 11)
Say: "If we could fix one thing in this deal this week, which one moves it furthest?"
Do: let the rep answer first, then agree or redirect. Write the gap as one sentence: "Nobody who signs has heard the business case."
Good looks like: one gap, stated as something the buyer has not yet said or done. "Send the proposal" is a task; "the CFO has not seen the number" is a gap.
Step 4. Choose the conversation (minutes 11 to 13)
Say: "Who is the one person who could fill that gap, and why would they take your call?"
Do: push for a named person. The answer is often the existing champion, asked for help.
Good looks like: a name, a reason they would make time, and a channel (call, meeting, intro).
Step 5. Say the opening out loud (minutes 13 to 18)
Say: "Give me the first two sentences you'll say to them. Out loud, the way you'll say it."
Do: listen for the buyer's own words in the opening. Then play the buyer for one exchange: give the pushback the rep is most likely to hear and ask for the reply. Ask what the rep wants to leave the call with (a date, a name, a number or an introduction).
Good looks like: an opening that uses something the buyer said, a reply to the likely pushback, and a specific ask. If it starts with "just checking in", go again.
Step 6. Commit (minutes 18 to 20)
Say: "When will you have that conversation, and when do we talk about what they said?"
Do: both dates go in the CRM. Note the gap and the planned conversation in the deal record so next week starts from it.
Good looks like: a conversation booked or requested before the rep hangs up.
Next week, the first question is: "Did it happen, and what did they say?"
A worked example (illustrative)
The rep, account and figures here are fictional.
Deal: Marisol is working Corran Health, a 900-person clinic network. CRM stage: Negotiation. Close date: end of month. Contact: Ben, Director of Patient Access.
Step 1. Marisol: "Ben's team loses hours to no-shows. He loved the demo, says it's a top priority. Legal has the contract." The manager notes three beliefs: loved the demo, top priority, legal has it.
Step 2. "What did Ben say that tells you it's a top priority?" Marisol checks her notes: Ben said no-shows run at about 14% and each one is an empty 40-minute slot. That is evidence. "Who signs?" Marisol thinks the COO, Elena. "Has Elena been on a call?" No. "What did legal say?" Ben said he "sent it over"; nobody at Corran has replied with redlines. Real stage: the buyer has priced the problem, and nobody who signs has engaged.
Step 3. Marisol picks the gap herself: "Elena has never heard why this matters."
Step 4. The person is Ben. He wants the project and he reports to Elena.
Step 5. Marisol tries an opening: "Hi Ben, just following up on the contract." The manager stops her. Second attempt: "Ben, you told me no-shows are running at 14%. Before legal spends time on this, can we get 20 minutes with Elena so she hears that number from you, with me there to answer questions?" The manager plays Ben: "Elena's slammed until next month." Marisol: "Then could I send you a one-page summary you'd be comfortable forwarding, and we ask for 15 minutes in the first week she's free?" What she wants to leave with: a date for Elena, or Ben's agreement to forward the page.
Step 6. Marisol calls Ben tomorrow. They talk again Thursday. The CRM stage moves back, with a note on why.
The deal looks smaller on the dashboard after this call. The forecast is more honest, and Marisol has a reason to call Ben with something new to say.
Coaching a new rep and an experienced rep
The six steps stay the same for every rep. What changes with tenure is where the manager spends the minutes.
A new rep usually stalls at step 2. They have not yet learned what counts as evidence, so "he loved the demo" sounds like progress to them. Spend longer on the evidence check, and name the standard each time: "That's a reaction. What did he say it costs?" Let the new rep borrow wording for the opening in step 5, then have them say it again in their own words.
An experienced rep usually has the evidence and skips straight to a plan. Their gap tends to sit higher in the deal: a signer they have assumed, or a competitor they have stopped worrying about. Spend the time on steps 3 and 4. Ask which gap moves the deal furthest, and push on whether the person they picked can fill it. Experienced reps often resist coaching on a deal they consider safe, so pick the deal with the biggest gap between its CRM stage and its evidence.
Spotting the gap that repeats across deals
One deal coaching call fixes one deal. After four or five calls with the same rep, the notes start to show a pattern: the same gap in deal after deal. A rep whose deals keep stopping before finance has a habit of selling to the person who likes the product. That pattern is worth a separate skill session, outside the deal coaching call. Keep a one-line record of the gap from each call so the pattern is visible, and raise it when it has appeared three times.
Where it goes wrong
The manager tells the deal. The manager has read the CRM and starts with "So this is at negotiation, right?" The rep agrees and the evidence check never happens. Fix: the rep speaks first, every time.
Four gaps, no plan. The manager spots everything wrong and lists it. The rep leaves with a to-do list and fixes none of it. Fix: name one gap and park the rest in the deal notes.
The plan is a task. "Get to the CFO" or "send a recap" ends the call. Neither is a conversation. Fix: step 5 is the call. If the rep has not said the opening out loud, the call is not finished.
Skill coaching in place of deal coaching. The manager hears a weak discovery question and spends ten minutes on questioning technique. That may be worth doing, in a separate session. The deal still needs its next conversation.
No follow-up. Next week starts with a new deal and nobody asks what the buyer said. The rep learns that the plan was a formality. Fix: step 6's second date, and the first question next week.
What to look for in a deal coaching tool
Many coaching platforms score a call after it happens. Deal coaching works one level down, on the opportunity, before the next buyer conversation. Four checks help when choosing a tool for it:
- It starts from the deal record. Through a CRM integration, the CRM stage, close date, contacts and recent notes should be in front of the coach, so the rep spends the time on evidence and does not retype the record.
- It coaches in your method. The evidence questions should use the team's own framework, such as Gap Selling, the ValueSelling Framework® or MEDDPICC, in the words your managers use.
- It runs on a call. The rep talks the deal through, because saying the opening line out loud is where the gap shows.
- It remembers, and can write back. The gap, the planned conversation and both dates should be kept with the deal (in the CRM if your team wants them there), and next week's session should open with "what did they say?"
A tool that passes all four can run the six steps between manager sessions. A tool that only scores recordings leaves the next conversation unplanned.
Coaching every rep on every deal
The procedure works. The constraint is that it takes a manager 20 good minutes per deal, and the manager's 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). What happens back at work is also more strongly tied to whether a skill gets used than what happens in the training room (Saks & Belcourt 2006; Blume et al. 2010). Both findings come via our kickoff field study.
So the question for most teams is how to give every rep this call on every deal that needs it.
A rep like Marisol brings the deal to Caty and talks it through; Caty separates the beliefs from the evidence, names what is missing and makes the rep say the opening line until it works, in the team's own methodology. Teams on Gap Selling get Keenan; teams on the ValueSelling Framework® get Val. The expert remembers the deal next week and asks what the buyer said. If the rep cannot talk right then, typing works as a fallback. The manager sees the read across the team and spends their own time where a human is needed. To hear the six steps run on one of your own deals, talk to us.
The 20-minute call is the short form. When a deal needs a written record, use the 30-minute deal review; when it has gone quiet, how to coach a stalled deal; and to choose which deals get the call at all, the pipeline review template.
FAQ
How do you coach a sales rep on a specific deal?
Run a 20-minute call on that one deal. Have the rep tell it from the buyer's side, ask for the evidence behind each claim, agree the single gap, pick the person who can fill it and have the rep say the opening of that conversation out loud. End with two dates: the conversation and the follow-up.
What questions should a manager ask in deal coaching?
Ask questions only buyer evidence can answer. What did they say or do that tells you that? What number did they put on the problem, and who said it? Has the person who signs been on a call? If you could fix one thing this week, which one? What are the first two sentences you will say?
How long should a deal coaching session be?
Twenty minutes for one deal is enough when the rep comes prepared. About four minutes for the rep to tell the deal, five to check evidence, two to name the gap, two to choose the conversation, five to rehearse the opening and two to commit to dates. Covering more deals in the same time turns it into a status update.
How is deal coaching different from a deal review?
They are close cousins. A deal review usually runs 30 minutes and produces a written record that feeds the forecast. Deal coaching is the shorter, rep-focused version whose only output is the next buyer conversation. Many managers run the coaching call inside the weekly one-on-one.
What if the rep does not know the answer to an evidence question?
Treat it as a finding. A rep who says "I don't know who signs" has just told you the deal's real stage. Write it down as the gap, and plan the conversation that finds out. Do not let the rep guess, because a guess repeated in a forecast becomes a fact.
Can an AI coach run a deal coaching call?
Yes: Caty, our deal expert, runs the call the same way on voice. She asks for the evidence, names what is missing, and builds a short roleplay from the deal so the rep can rehearse the opening of the next conversation in the team's methodology, then debriefs it. She remembers the deal next week. A rep who cannot talk can type it in.