Coaching an underperforming sales rep means finding out why they are behind, then working their live deals with them more closely than usual until the cause is fixed or it is clear it will not be. The front-line manager does it, and it usually runs four weeks: about an hour of diagnosis up front, then two short sessions a week.
The common mistake is coaching before diagnosing. A rep at 55% of quota might have a discovery problem, a pipeline problem, a territory problem, or something at home. Each needs a different response, and only one of them is a coaching problem. This guide uses the same three-part session as the rest of our sales coaching framework: brief, observe, debrief. For an underperformer the loop runs tighter and the plan has dates.
What coaching an underperformer involves
Underperformance coaching is ordinary deal coaching with a diagnosis at the start, a shorter interval between sessions, and a decision at the end. The diagnosis decides what to coach, and the decision at week four decides what happens to the rep next.
- Up frontDiagnose
- Confirm the gap against peers
- Find the stage where deals stall
- Separate skill from everything else
- Weeks one to fourRun a tight loop
- Two sessions a week
- One gap, one move, a date
- Week fourDecide on evidence
- New skill
- Extend by two weeks
- Formal performance process
One piece of research should shape how hard you push. Across 1,246 pharmaceutical sales reps, managers' coaching skill predicted goal attainment, and frequent coaching from less skilled managers was linked to worse results (Dahling et al. 2016, via our kickoff field study). The rep who is behind gets the most coaching, so the coach's skill matters most here. So the plan below keeps every session short and specific, and it should be run by a manager who coaches well.
How to coach an underperforming rep in seven steps
Coach an underperforming rep by confirming the gap in the numbers, diagnosing its cause from calls and deals, then coaching that cause on live deals at a shorter interval until a set decision date.
Confirm the gap with the numbers. Look at quota attainment and win rate over two quarters, against peers with similar territories. What good looks like: you can say how far behind the rep is and whether it is new or long-running. One bad month is noise.
Find the stage where deals stall. Compare the rep's stage-to-stage conversion with the team's. A rep who books meetings but loses after the demo has a different problem from one who cannot fill the top of the pipeline. What good looks like: one stage where the rep's conversion falls well below the team.
Read the calls at that stage. Pick three recent calls on open or recently lost deals at the weak stage. Read for the buyer's words: what they said about the problem, the cost, the decision, the timeline, and what the rep did next. What good looks like: a pattern that shows up in at least two of the three calls, with quotes.
Separate skill from everything else. Ask the rep, on a call, what they think is happening. Then test the pattern. If the rep can describe the right move and does not make it, the cause may be confidence or habit. If they cannot describe it, it is a skill gap. If the pipeline is thin, it is a prospecting problem. If the deals are poor fit, it may be territory. If something outside work is going on, coaching is the wrong tool. What good looks like: one named cause that you and the rep agree on.
Write a four-week plan with one or two skills. Name the skill in the methodology's terms, pick two or three live deals where it will be tested, and state the evidence that will show it has changed. Use a sales coaching plan. What good looks like: "Reach the economic buyer by the second meeting. Evidence: the economic buyer states the decision process on a call, on two of three named deals."
Run a tight loop for four weeks. Brief before every important call on the named deals (five to ten minutes). Read or listen to the call within a day. Debrief on a call within 48 hours: rep goes first, one gap with the buyer's quote, one move with a date. What good looks like: two sessions a week, each ending with a move the rep makes on the next buyer call.
Decide at week four, on evidence. Look at the rep's calls across the four weeks in order. Is the named behavior showing up more often, and are the deals moving? What good looks like: a clear call. Continue with a new skill, extend by two weeks with a reason, or move to a formal performance process with the evidence attached.
On step 7, judge the trend across many calls. A single call score is a weak signal. In our research on AI call scoring, trained human assessors marking the same calls disagreed on 18% of individual scores. The ranking of a rep's calls over a month says more than any one number.
Worked example: four weeks with one rep (illustrative)
The rep, deals and figures below are invented to show the steps.
Jordan is in his second year selling a data platform. He is at 52% of quota after two quarters, and the team average is 94%. His meeting volume matches the team.
Diagnosis. His conversion from discovery to proposal is close to the team's. From proposal to close he wins about one deal in six, where the team wins one in three. His manager reads three late-stage calls. In all three, the buyer says something like "I need to take this to my VP" and Jordan replies "Of course, let me know how it goes." He never meets the VP. On a call, Jordan says he does not want to seem pushy. He can describe multi-threading. He does not do it. The cause is habit and confidence on one move, and the skill itself is there.
Plan. One skill for four weeks: get to the person who signs before the proposal goes out. The team sells with MEDDPICC, so the plan names it as the economic buyer. Three named deals. Evidence: on two of the three, the economic buyer joins a call before the proposal.
Weeks one and two. Before each late-stage call, a five-minute brief: who signs, and what will Jordan say when the buyer offers to "take it to my VP"? They agree a line: "That makes sense. What will your VP want to see? I'd like to build it with you, and fifteen minutes with them would help me get it right." In the first debrief Jordan admits he did not say it. By the third call, he does. The buyer agrees to set up the call.
Weeks three and four. Two of the three deals now have the economic buyer on a call. One of them moves to commit. In the week-four review, his manager puts Jordan's week-one calls next to his week-four calls. The late-stage calls rank higher, and the move shows up without a brief on a fourth deal nobody planned for. They pick the next skill.
Where underperformance coaching goes wrong
Coaching before diagnosing. A rep with a pipeline problem gets discovery coaching for a month and nothing changes. The hour of diagnosis saves the month.
Too many skills at once. A plan with five development areas reads as a list of failures. One or two skills, tested on named deals, is a plan the rep can act on.
Practice in place of deals. Rehearsal can help a rep say a hard line out loud once. The evidence of change is the line said to a real buyer on an open deal. Skills that are not used decay; after more than a year unused the effect size is minus 1.4 (Arthur et al. 1998), and transfer depends on what happens back at work (Saks and Belcourt 2006, via our kickoff field study).
No end date. Coaching that runs forever tells the rep nothing about where they stand. Four weeks with a decision is fairer to the rep and to the team.
Doing this without losing the rest of the team
The seven steps cost roughly an hour of diagnosis and two sessions a week for a month. Most managers can do that for one rep. Few can do it for one rep and keep coaching the other seven.
That is the problem our AI sales experts take on. In Replicate Labs, the rep brings each named deal to Caty on a call, by voice or video. Caty briefs before the buyer meeting, works the transcript afterwards for what the buyer said and what is missing against the team's methodology, and agrees the next move with the rep. Caty remembers the plan and the deals, so each session starts where the last one ended. Typing is the fallback for when the rep cannot talk.
The manager keeps the diagnosis and the week-four decision, and gets the read across the team from Bryce. More on that is on the for leaders page. If you have a rep at 55% of quota and no time for two sessions a week, talk to us.
For questions to use in each debrief, see sales coaching questions. For the week-four review, see how to measure sales coaching effectiveness.
FAQ
How do you coach a sales rep who is not hitting quota? Start with a diagnosis. Confirm the gap against peers, find the stage where the rep's deals stall, and read three calls at that stage for the buyer's words. Agree the cause with the rep. If it is a skill, run a four-week plan on two or three live deals with a brief and a debrief around every important call.
How long should you coach an underperforming sales rep? Four weeks is a practical first block. It gives the rep enough buyer calls to show a change and keeps the decision close enough to matter. At week four, compare the early and late calls and decide whether to continue with a new skill, extend by two weeks with a stated reason, or move to a formal process.
What is the difference between a skill gap and a will gap in sales? A skill gap means the rep does not know how to make the move; a will gap means they know and do not do it. Test it by asking the rep to describe the right move. If they can describe it and still do not make it on calls, the cause is confidence, habit or motivation, and the coaching focuses on doing it once on a real deal.
Should an underperforming rep get more coaching than other reps? They should get closer coaching for a fixed period, at a clear standard. Research across 1,246 pharmaceutical reps found frequent coaching from less skilled managers was linked to worse results (Dahling et al. 2016, via our kickoff field study). More sessions are not enough on their own: make each one specific, tied to the rep's deals and judged against the team's methodology.
When should coaching turn into a performance improvement plan? Move to a formal plan when four to six weeks of specific coaching on live deals has not changed the behavior on calls, and the numbers have not moved. The coaching record, with dated moves and call evidence, then becomes the basis for the formal plan, which is fairer to the rep than a plan written from the quota number alone.
Can AI help coach underperforming sales reps? Yes, if it coaches the rep's live deals and does more than score calls. An AI coach can brief the rep before each important buyer call, debrief it afterwards against the team's methodology, and remember the plan across sessions. The manager keeps the diagnosis and the decision at the end, and gets back the hours to coach the rest of the team.