How to Coach a Salesperson (A Weekly Sales Coaching System, Questions, and Template)

How do you coach a salesperson?

To coach a salesperson, meet with them every week, review one real sales call or deal together, and focus on one skill to improve. Ask them what went well and what they would do differently before you share your own view. Then practice the skill in a short role play, agree on one specific thing they will do differently next week, and check how it went at the next session. The goal is a steady change in how they sell, not a lecture about their numbers.

My strong opinion: most small business owners think they coach their salespeople when they are really just reviewing the scoreboard. Asking why the numbers are down is not coaching. Listening to a call and saying the discovery questions stopped too early, then practicing better ones, is. If you only talk about results, you will get a salesperson who knows they are behind and has no idea what to change.

Sales coaching vs sales management

You need both. Keep them in separate meetings if you can. When the numbers review and the coaching happen in the same half hour, the numbers always win and the coaching gets squeezed out.

A simple weekly sales coaching system

1. Pick the material before the session. Ask the salesperson to choose one recorded call or one open deal they want help with. Recordings need the other person's permission. If they choose, they come in ready to learn instead of ready to defend themselves.
2. Review it on your own first. Listen to the call or read the deal notes and write down what went well and the one moment that mattered most.
3. Ask them first. Open the session by asking how they think it went, what they would keep, and what they would change.
4. Agree on one skill. Choose a single skill to work on, such as asking a deeper follow-up question, handling a price objection, or setting a clear next step at the end of a call.
5. Practice it. Role-play the moment that went wrong and let them try it again until it sounds natural.
6. Set a commitment. Agree on exactly what they will do differently on their next calls this week.
7. Follow up next week. Start the next session by asking how the commitment went, and only move to a new skill once the last one has stuck.

How to run a sales call review

A call review is the most useful coaching material you have, because it shows what actually happened instead of what the salesperson remembers. Listen for these parts of the call.

For the discovery part, How to Run a Discovery Call That Leads to a Clear Yes or No gives you a standard to compare against. For objections, use How to Handle Sales Objections Without Sounding Pushy.

Sales coaching questions to ask

Good questions get the salesperson thinking about their own performance, which makes the change far more likely to stick than a list of instructions.

• "What were you trying to get out of this call?"
• "What do you think went well, and why?"
• "Where did the call change direction?"
• "What did the buyer say that you wish you had asked more about?"
• "If you could have one moment back, which would it be and what would you say?"
• "What is the next step on this deal, and does the buyer agree with it?"
• "What will you try differently on your next call?"

Sales coaching template

Keep one shared document per salesperson and add to it every session.

1. Date and material reviewed: the call or deal you looked at.
2. What went well: in their words first, then yours.
3. The moment that mattered: the point where the call or deal could have gone better.
4. Skill to work on: one skill only.
5. Practice notes: what you role-played and how it went.
6. Commitment: exactly what they will do differently this week.
7. Follow-up: how last week's commitment went.
8. Skills history: a running list of skills worked on and whether each one has stuck.

A sales coaching example

Here is an illustrative session for a made-up salesperson at a small web design agency. All details are invented to show the format.

Notice that the session never talks about the agency's monthly target. The goal is a better discovery call, which over time is what moves the target.

Sales coaching mistakes to avoid

• Talking only about numbers and calling it coaching.
• Trying to fix five things in one session, so nothing changes.
• Telling the salesperson what they did wrong before asking what they noticed.
• Coaching from memory instead of from a real call or deal.
• Only coaching the people who are struggling, while your best salespeople get no help to get better.
• Skipping the follow-up, so commitments are made and quietly forgotten.
• Cancelling sessions whenever the week gets busy.

If you are coaching a brand new hire, start with How to Onboard a New Salesperson (30-60-90 Day Plan, Checklist, and Template) and move to this weekly system once they are selling on their own. To see which skill to work on first, compare their numbers with Sales KPIs for Small Business: What to Track and How to Calculate Each One, and use How to Do a Win-Loss Analysis (Questions, Template, and Steps) to find patterns across many deals.

How to prepare sales coaching sessions with Claude

Claude can cut the time it takes to prepare each session, so the session itself goes to practice. Use the Claude desktop app with your real material.

1. Paste in a call transcript you have permission to use, along with your sales process or playbook. Remove anything sensitive first.
2. Ask Claude to review the call against the table above and list what went well and the single moment that most changed the outcome. Listen to that part of the recording yourself before you rely on it.
3. Ask it to suggest three coaching questions about that moment, phrased so the salesperson does most of the talking.
4. Ask it to play the buyer from the call so the salesperson can practice the moment again, then give feedback against your own process.
5. After the session, paste in your notes and ask Claude to update the coaching document and remind you of the commitment to check next week.