How to Coach a Salesperson: A Working System for Sales Managers
Reviewed by Peter McKeon, Founder and CEO, Salesmasters International. 30+ years in sales and executive leadership; past Vice President and Board Member of the Chamber of Commerce & Industry Queensland.
Salesperson coaching is a weekly management rhythm, not an annual event. The working system has six parts. Choose one skill per rep per month. Run a ten-minute deal review every week. Observe real selling. Give one behavioural correction at a time. Track the pipeline evidence. And know the point where in-house effort stops being enough.
Sales teams rarely fail because a manager does not care. Sales teams fail because a manager’s week is eaten by forecasting, reporting, hiring and customer escalations. Help arrives only once a deal is stuck. Reactive talk manages the result. Coaching builds the salesperson.
Salesmasters International has worked with more than 1,000 businesses across Australia since 1991. Below is the manager-ready system, built for new starters, experienced reps and underperformers alike, with real client numbers attached to each step.
1. Pick one skill per rep per month
Step 1 of salesperson coaching is to choose one priority skill per rep per month, and only one. When a rep misses target, the feedback list swells to eight items at once: prospecting, discovery, qualification, objection handling, follow-up, negotiation, CRM discipline and confidence. Eight priorities is no priority.
Pick the skill from three inputs. First, pipeline evidence, meaning where deals slow, stall or disappear. Second, conversation evidence, meaning what a manager actually hears on calls and ride-alongs. Third, behaviour evidence, meaning what a rep repeatedly avoids, rushes or overcomplicates.
For example, when Salesmasters began work with Compass Cars, closing rates had been falling roughly 10% a year and the real gap sat in one place: telephone enquiries and site evaluations were being handled without a consistent method. Naming the gap precisely is what makes coaching possible.
The skill must be specific enough to observe. “Build confidence” is not coachable. “Ask one impact question before discussing product features” is coachable, and cross-checks cleanly against your sales metrics.
2. Run weekly ten-minute deal reviews
Step 2 is a ten-minute deal review every week, and the review is the highest-leverage of the sales coaching techniques available to a working manager. The purpose is not pipeline inspection. One deal becomes a window into a rep’s thinking, habits and next-action quality.
Five questions fill ten minutes:
- What is the opportunity, who is involved, and why does the outcome matter to the buyer?
- Where is the deal now, and what evidence proves the stage is real?
- What could stop the deal from moving?
- What specific step happens before the next review?
- How does the deal connect to the monthly skill?
For example, Levanta worked with Salesmasters on exactly this discipline and cut the average sales cycle from 120 days to 30, with revenue up 48% within eight weeks. Predictability does the work: same day, same five questions, same standard. Deals stop drifting because next actions stop being optional.
3. Observe live calls and ride-alongs
Step 3 is direct observation, because a manager cannot coach what a manager has not seen. Pipeline reports show the result of behaviour. Live calls and ride-alongs show the behaviour itself. For inside sales, observation means listening to live discovery calls, reviewing recorded demos and auditing follow-up emails. For field sales, observation means joining customer meetings and debriefing in the car immediately afterwards.
Observation also fixes a visibility problem most managers do not know they have. Working with Bishopp Outdoor Advertising, in-field coaching produced a 40% improvement in visibility of team performance inside a month, alongside a 22% lift in sales.
Agree the role before the meeting starts. Observing only? Joining as senior support? Taking one section? Stepping in only if the deal is at risk? A manager who rescues every difficult moment teaches dependency rather than skill, so observe far more than you rescue. If you are learning how to coach salespeople, observation is where theory turns real.
4. Give one behavioural correction at a time
Step 4 is a single behavioural correction per observation, structural rather than personal. After a call, the temptation is to unload everything: the opening was soft, discovery was shallow, the rep talked too much, pricing came too early, the next step was vague. All five may be true. Deliver all five and a rep retains none.
A correction that sticks has four parts: the observed behaviour, the commercial impact, the replacement behaviour, and the next chance to practise. In practice, that sounds like this:
“In the discovery call you moved to the demo before asking about cost, urgency or who else is affected. We positioned the product before understanding the business impact. On the next call, ask one impact question first. Try: what does the issue cost the team when the issue repeats?”
Corrections at exactly the level of enquiry, quote and close are what lifted Compass Cars to 20% higher closing rates. Coaching sales reps well shapes a behaviour, never a character.
5. Track improvement with pipeline metrics
Step 5 is measurement, and salesperson coaching has to show up in the pipeline before revenue moves. Match the leading indicator to the monthly skill. For prospecting, count new qualified conversations and connect-to-meeting conversion. For discovery, count opportunities carrying a recorded business pain and a named decision process. For next-step control, count meetings ending with a scheduled follow-up. For negotiation, watch discounting patterns and deals lost to no decision.
Closed revenue alone hides the improvement. A rep sharpens discovery in March, creates better-qualified opportunities in April, and closes them in June.
Compass Cars shows the full sequence. Alongside the closing-rate gain, sales rose 16% and staff turnover fell from 30–40% to 8%, while Titan Garages halved sales onboarding time. Behaviour numbers move first, revenue numbers second, and reporting in that order is what makes coaching credible when leading sales teams.
6. Know when to bring in outside coaching
Step 6 is knowing the ceiling. Bring in outside help when the same gap appears across several reps, when forecasts stay unreliable despite healthy activity, when a team shares no common sales language, or when a new manager needs building into a coach. One struggling rep is a coaching job. Three reps failing at the same stage is a system job.
Research favours building the internal coach over renting an external one indefinitely. A 2016 meta-analysis of workplace coaching led by Aston University, published in the Journal of Occupational and Organizational Psychology, found positive effects on organisational outcomes, with stronger effects for coaches internal to the organisation. According to Gartner, effective sales managers lift seller performance several times over, yet only 18% of sales managers lead high-performing teams.
Salesmasters works manager-first for that reason. Once a sales process is documented, we coach the sales manager on embedding the process and building the operating rhythm, then develop the manager into the coach of the team. Training builds skill, sales coaching embeds skill, and reinforcement sustains skill.
How often should you coach reps?
Salesperson coaching is a weekly job, but only one conversation needs to be formal. The workable pattern for a manager with a full workload is a monthly skill choice, one ten-minute deal review each week, an observed selling moment weekly or fortnightly, one behavioural correction after each observation, and a pipeline review at month end. Total cost: roughly 40 minutes per rep per month.
Research supports the short-cycle rhythm. A University of Sydney randomised controlled study of 41 executives paired a half-day workshop with four individual coaching sessions across 10 weeks, and measured better goal attainment and resilience against a control group. Four focused sessions changed behaviour. One long annual session does not.
New starters need the cycle tighter, usually two observations a week in month one. Experienced reps need less frequency and more challenge, often on enterprise deals or negotiation discipline. Reps in difficulty need closer structure, never random pressure.
How do you coach an underperformer?
Coaching underperforming reps starts by separating three different problems: skill, will and fit. Can the rep perform the required behaviour? Is the rep putting in the effort and ownership? And is the role, market or sales motion right for the person at all? Treating all three as one problem is why underperformance conversations stall for months.
If the problem is skill, run the six salesperson coaching steps above tightly for four weeks. If the problem is will, the conversation turns direct, and accountability sits alongside support. If the problem is fit, more training will not solve anything, and delay is unfair to everyone including the rep.
For example, set the expectation out loud at the start: “Over the next four weeks we focus on discovery calls. The behaviour is asking impact questions before presenting. I will review one deal each week and observe two calls, then we review the evidence together on the 30th.”
Coaching or managing: what’s the difference?
Managing sets direction, standards, priorities and accountability. Coaching develops the skill, judgement and behaviour a salesperson needs to meet those standards. Both are required, and neither substitutes for the other.
Managing sounds like: your target is this, here is the activity standard, the forecast needs updating, every opportunity must carry a next step. Sales manager coaching sounds like: let’s listen to how you opened the call, what question could have uncovered urgency earlier, how will you confirm the decision process next time, let’s practise the price response before Thursday.
Managers who only manage produce compliance without growth. Managers who only coach produce good conversations without accountability. According to Gartner, only 55% of chief sales officers say frontline managers consistently meet performance expectations, which is a gap in exactly this combination. The Salesmasters standard holds both: clear expectations, close observation, practical skill development, and measurable commercial progress.
Common mistakes sales managers should avoid
Six errors account for most wasted coaching effort. First, trying to fix everything at once, which feels thorough and slows improvement. Second, confusing advice with coaching, where every conversation becomes “here is what I would do” and the rep gradually stops thinking. Third, reviewing deals without reviewing behaviour, which identifies risk but never improves the skill behind the risk.
Fourth, avoiding live observation, because a CRM note cannot show tone, timing or the moment a rep talked past a buying signal. Fifth, waiting until performance is already a crisis, when early input costs less and works better than a late rescue.
Sixth, treating top performers as finished products. At Bishopp Outdoor Advertising, 70% of revenue was produced by two top performers before the coaching engagement, which is a concentration risk rather than a success story. Strong reps still need challenge on strategic accounts, negotiation discipline and mentoring others.
The manager’s weekly checklist
The manager’s weekly checklist is a seven-point Friday review of the whole system, and the check takes about two minutes:
- Has each rep got one monthly skill focus?
- Have you reviewed one live deal with each priority rep?
- Have you observed real selling behaviour rather than reading CRM notes?
- Have you given one clear behavioural correction?
- Have you linked the feedback to pipeline movement?
- Have you recognised improvement as well as gaps?
- Do you know which gaps are internal and which need outside help?
Seven yes answers means the system is running. Three or four means the week won, which happens to every manager. The fix is to protect the ten-minute reviews first, because ten minutes is the smallest unit of the system and the unit carrying everything else.
The strongest sales leaders in Australia do not rely on heroic one-off interventions. Strong leaders build a repeatable management system that compounds, quarter after quarter, busy month or quiet one.
Start the system, then decide about outside help
The first month is the honest test of any salesperson coaching system. Run it once before judging the result: pick the skill, hold four deal reviews, observe two calls, correct one behaviour, and check the pipeline evidence at month end. Most managers see the change first in the quality of next steps, not in the revenue line, which is why 30 days is long enough to know whether the rhythm holds.
If the same gaps keep returning across the team after a full month, the ceiling is structural rather than personal. Salesmasters has built sales systems for Australian SMEs since 1991. We partner with SHL on assessment, and we back the coaching engagement with a plain commitment: if we don’t increase your sales, you don’t pay.
Speak to our team about where external coaching accelerates the next stage, and we will help you decide whether the answer is coaching, sales training, or a tighter sales process underneath both.
