Training and coaching

Is an Underperforming Rep a Skill Problem or a Will Problem?

By Jordan Stupar · October 2, 2026 · 7 min read

Most owners decide whether a struggling rep can't or won't based on attitude in meetings, and they get it wrong often enough to cost them good people. The real answer sits in two places: what the rep does when nobody is watching, and what happens when they practice the exact moment they keep losing. A rep who practices, finishes the work, and still fumbles the close has a skill problem, and skill problems are coachable. A rep who skips the practice, skips the follow-ups, and ignores the redo has a will problem, and no amount of training fixes that. You need both signals, measured the same way for everyone, before you make the call.

Cover illustration for Is an Underperforming Rep a Skill Problem or a Will Problem?

Why owners usually guess wrong

The guess is usually made from personality. The quiet rep who does not speak up in the sales meeting gets labeled as checked out, and the confident rep who talks a good game gets labeled as capable but unlucky. Neither label comes from the work. It comes from how each person performs in front of you, which is a different skill from performing in front of a buyer.

The cost runs both ways. Fire a rep with a skill gap and you throw away the months you spent hiring and ramping them, then start the same cycle with someone new. Keep coaching a rep with a will gap and you spend your scarcest resource, your manager's time, on someone who was never going to change. With 73% of sales managers spending under 30 minutes a week coaching a rep (ATD 2025, Gong 2025), there is no slack for spending that time on the wrong person.

What a skill problem looks like in the evidence

A skill problem shows up as effort without results. The rep finishes the lesson, completes the follow-ups on their list, and logs real practice. Then on live calls they lose at the same point, again and again. They present before confirming who decides, or they cave the first time price comes up, or they end the call without booking a next step.

That pattern is good news. It means the rep is willing and the gap is specific. The fix is narrow: identify the one moment they keep losing, have them rehearse it until they clear the bar, and check whether it shows up differently on the next real call. Skill problems shrink when the practice targets the exact moment, not when the rep sits through another general training day.

  • Lessons and workbooks finished on time
  • Follow-ups and daily tasks completed
  • Role play attempted repeatedly, scores climbing slowly
  • Live calls lost at the same identifiable moment

What a will problem looks like in the evidence

A will problem shows up as missing effort, regardless of results. The lesson is not finished. The follow-ups on the list are not done. The role play is logged in once and abandoned. When a manager assigns a redo, it is late or never completed. Sometimes this rep is even hitting an acceptable number, usually by working the easiest leads, which is why results alone hide it.

The important part is that a will problem is visible in behavior that has nothing to do with talent. Finishing a 15-minute lesson does not require skill. Completing a follow-up list does not require charisma. When those basic, low-difficulty actions are consistently skipped, you are not looking at someone who cannot sell. You are looking at someone who has decided not to do the job the way you defined it.

How to measure both signals the same way for everyone

The difficulty is that most companies have no record of the effort side at all. Training is a binder or a one-time event, and 84% of what reps learn in training is gone within 90 days (Sales Performance International). Follow-ups live in the CRM if anyone logs them. Practice, if it happens, happens in a hallway. So the owner falls back on impressions, because impressions are the only data available.

In Revenue OS, the effort side is the Compliance Score: one number per rep, 0 to 100, recalculated nightly, built from training completion at 30%, daily tasks at 25%, role play quality at 25%, and manager enforcement at 20%. The skill side comes from scoring. Sales Academy role plays are scored in about 60 seconds on script adherence, objection handling, close attempt, energy and tone, and follow-up setup, and real calls are scored against six core skills plus your own process at 60% weight. Put the two side by side and the diagnosis mostly makes itself.

What to do once you know which one it is

For a skill problem, coach the one moment. Pull the timestamp of the worst moment on the last real call, have the rep re-fight that exact situation against an AI customer, and set the bar at 80. A call under 80 becomes a redo due 6pm the next business day. Then watch whether the next real-call score moves. If effort is high and the score climbs, you made the right call by keeping them.

For a will problem, coaching is the wrong tool. Have the direct conversation, show the rep their own completion record, and make the expectation explicit with a date. The data keeps that conversation about behavior rather than personality, which makes it fairer to the rep and easier for you. If the effort numbers do not move after that, you have your answer, and you reached it on evidence rather than a feeling from a Monday meeting.

The short version

  • Owners usually judge skill versus will from how reps act in meetings, which is a poor predictor of how they act with buyers.
  • A skill problem is effort without results: work done, practice logged, the same moment lost on live calls.
  • A will problem is missing effort on low-difficulty tasks like lessons, follow-ups and redos, whatever the numbers say.
  • Measure effort and skill separately for every rep, then coach the first and confront the second.

Questions owners ask

Can a rep have both a skill problem and a will problem?

Yes, and it is common with newer reps who are struggling and losing confidence. Fix the will side first, because without the effort there is nothing to coach. Once the rep is completing lessons, tasks and practice consistently, the skill gaps become visible and specific, and they can be worked one moment at a time.

What if my underperformer is hitting quota?

Results can hide a will problem for a long time, usually because the rep is working the easiest accounts or discounting to close. Look at the effort record and at how their calls score against your process. If both are low while the number looks fine, the number is borrowed, and it tends to run out.

How long should I coach a skill problem before deciding it will not improve?

Long enough to see whether targeted practice moves the live-call score on the specific moment you are coaching. If the rep is doing the work and the redo cycle is running, you should see the pattern start to change within a few weeks of real calls. If effort is high and nothing moves at all, revisit whether the role is the right fit.

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