How do you turn around an underperforming sales rep?

Why This Happens — Diagnose Before You Coach

Underperformance is a symptom, not a cause. The fastest way to waste a quarter is to coach the wrong thing. Run every struggling rep through four buckets:

• Skill — they want to hit number but don't have the mechanic (can't run discovery, can't handle the "we already have a vendor" objection, can't multithread a buying committee). This is the most coachable bucket.
• Will — they have the ability but have lost motivation, belief, or trust. Often caused by a recent loss streak, a personal issue, or feeling the territory is unwinnable. Coaching tactics here fails; you have to rebuild belief first.
• Knowledge — they don't know the product deeply, the competitor set, or who their actual buyer is. This shows up as shallow discovery and "spray and pray" demos.
• System / territory / comp — the rep is fine, but the patch is dead, the ICP is wrong, the comp plan punishes the right behavior, or marketing hands them garbage leads. No amount of 1:1s fixes a structural problem.

A practical tell: pull the rep's last 10 calls in Gong or Chorus and watch the first five minutes of each. If discovery is consistently thin, it's skill. If the rep sounds flat and rushes, it's will. If they can't answer a buyer's technical question, it's knowledge. If the deals are simply too small or too few to ever make quota, it's a system problem — and that's on you, not them.

The Coaching Conversation

The turnaround conversation sets the tone. Use the GROW model — Goal, Reality, Options, Will — so the rep does the thinking and owns the plan. Your job is to ask, not to lecture. Open honest and direct, then get collaborative fast.

Open (name it without shame):

> "I want to be straight with you because I'm invested in you winning here. The numbers haven't been where we both want them for two quarters, and I'd rather fix it together now than have a much harder conversation later. So today is about building a real plan — not me reading you a list. Are you in for that?"

Goal:

> "Forget the annual quota for a second. What's the *one* thing that, if you got good at it in the next 30 days, would move your number the most?"

Reality (make it specific, use evidence):

> "I pulled your last ten calls. On eight of them, we jumped to the demo inside four minutes. Walk me through what's happening in discovery — what's getting in the way of slowing down and earning the right to present?"

Options:

> "If you were coaching another rep with this exact pattern, what two or three things would you tell them to try?"

Will (lock the commitment to ONE skill):

> "Of those, which one do you want to own first? Great — discovery it is. Here's my commitment: we review two calls a week together for the next month, and I'll role-play the hard openings with you. What's *your* commitment?"

Close every turnaround 1:1 by writing the single focus skill, the quick win you're targeting, and the cadence into a shared doc. Reps disengage when "coaching" feels vague; they re-engage when there's a concrete plan with their fingerprints on it.

The Coaching Plan / Cadence — A 30/60/90 Turnaround

Days 1–30 — Stabilize and get a quick win. Lock one focus skill. Get the rep an early, visible win to rebuild belief — hand-pick a winnable deal, pair on it, or revive a stalled opportunity together. Two call reviews per week, one role-play. Celebrate the win loudly and tie it to the new behavior.

Days 31–60 — Build the habit. The rep now runs the focus skill on live calls with you observing, not driving. Shift from "I'll show you" to "show me." Add a second behavior only once the first is consistent. Review leading indicators weekly.

Days 61–90 — Prove durability and decide. The rep should show the behavior unprompted and the leading indicators should be trending. If they are, broaden scope and graduate them off intensive coaching. If they're flat after honest, documented effort on both sides, that's your signal to move to a formal performance plan — and you'll do it with a clean conscience and a paper trail.

Drills & Role-Play

Coaching that lives only in conversation rarely changes behavior. Build reps the way an athlete trains — repeatedly, against resistance, with a scorecard:

• Call review with a scorecard. Pick two recorded calls a week. Score against a simple discovery or objection-handling rubric. Make the rep self-score first, then compare. Disagreements are the lesson.
• Objection gauntlet. You play a tough buyer. Fire the rep's three most-feared objections back to back until the response is reflexive, not improvised.
• Cold-open role-play. Practice the first 90 seconds of a discovery call ten times. The opening is where most thin calls are lost.
• Win/loss teardown. Have the rep present a recent loss to the team using MEDDICC or Command of the Message to expose where the deal actually broke.
• Ride-along on a strong rep's call. Knowledge and confidence transfer fastest by watching a peer who does the skill well.

What to Measure

Quota is a lagging indicator — by the time it moves, the quarter is over. Coach to leading indicators that show the behavior is changing weeks before the number does:

• Activity quality, not just volume — discovery calls that hit a minimum talk-ratio and uncover a quantified business problem (visible in Gong or Clari).
• Conversion between stages — discovery-to-demo and demo-to-proposal rates for the focus skill you're coaching.
• Behavior-change reps — how many calls per week show the new skill applied unprompted.
• Pipeline coverage — is created pipeline finally enough to hit number, or is this still a system problem in disguise.
• Win rate and sales-cycle length on the rep's deals over a trailing 30 days.

If activity and stage conversion improve but quota lags, stay the course — the lag is normal. If neither moves after 60 honest days, stop coaching tactics and address fit or system.

Common Mistakes Managers Make

• Rescuing instead of coaching. Jumping on every call to save the deal feels helpful but trains dependence. Coach the skill; let the rep run the deal.
• Coaching the deal, not the skill. Deal reviews fix one opportunity. Skill coaching fixes every future opportunity. Do both, but never skip the skill.
• No follow-through. Setting a plan and not reviewing calls weekly is the number-one reason turnarounds fail. The cadence *is* the coaching.
• Coaching everyone the same. A will gap and a skill gap need opposite approaches. Diagnose first, every time.
• Confusing motivation with development. A pep talk is not a plan. Belief gets rebuilt by a quick win, not by a speech.
• Coaching past the honest answer. When it's a wrong-fit hire or a structural problem, more 1:1s just delay the inevitable and burn the rep's confidence and your quarter.

The Hidden Pipeline Problem — Quantity vs. Quality

Many turnarounds fail because managers focus on activity metrics (calls, emails, meetings) without checking pipeline health. An underperforming rep often has a pipeline that looks full on paper but is full of stalled deals, unqualified leads, or prospects who can't buy in the current quarter. Run a pipeline audit with them: pull every open deal, rank it by likelihood to close in the next 30 days, and flag deals that have been sitting for 60+ days without a next step. If 60% of their pipeline is dead weight, no amount of closing technique will help — they need to rebuild from scratch with better qualification. A healthy pipeline should have 3–4x their quota in committed stage deals, with at least 40% in the last two stages. If they're under 2x, the real problem isn't skill — it's sourcing.

The Emotional Reset — Rebuilding Belief After a Losing Streak

A rep who has missed quota for 3+ months often carries a hidden weight: they stop believing they can win. This manifests as hesitation on calls, skipping discovery, or avoiding tough conversations. Before any skill work, do an emotional reset: review three wins from their past (even small ones), identify what they did differently, and recreate that pattern. Then set a micro-win goal for the first week — something they can achieve in 48 hours, like booking one meeting with a decision-maker or getting a "yes" on a trial. The goal isn't revenue; it's proving to their brain that they still know how to close. Once belief returns, skill coaching sticks. Without it, you're teaching a mechanic to a driver who's afraid to get behind the wheel.

The Manager's Mirror — When You're Part of the Problem

Sometimes the rep isn't the root cause — your management style is. Ask yourself honestly: have you been giving vague feedback ("be more assertive"), skipping ride-alongs, or assigning them leads that don't fit their strengths? A rep who's been micromanaged often shuts down; one who's been ignored drifts. Run a 90-day co-selling sprint: ride along on every major call, debrief immediately, and model the behavior you want. If the rep improves under direct support, the issue was your distance, not their ability. If they don't, you've confirmed the gap is theirs — and you can act with clarity.

FAQ

How long should I give an underperforming rep before deciding? A disciplined 30/60/90 plan gives you a clean read. Expect leading indicators (discovery quality, stage conversion) to move within 30–45 days and the number to follow by 90. If activity and conversion are both flat after 60 days of documented, two-sided effort, that's your decision point — extend only if there's a real trend.

What if the rep is defensive or blames leads, territory, or marketing? Separate signal from excuse with data. Pull the pipeline math: if coverage genuinely can't produce quota, they're right and it's your problem to fix. If coverage is fine, acknowledge their frustration, then redirect to what's inside their control: "I hear you on the leads — and let's also make sure that when a good one comes, we convert it. That's the part we own."

Should I coach skill or motivation first? Diagnose first. If it's a will gap, lead with a quick win to rebuild belief — coaching mechanics into a disengaged rep bounces off. If it's a skill gap, go straight to the focus skill and drills. Coaching the wrong bucket is the most common reason turnarounds stall.

How is coaching different from a performance plan (PIP)? Coaching develops a willing rep who can improve. A performance plan is a formal, documented step with defined expectations and consequences. Use coaching first and honestly; move to a plan when coaching has been given a fair shot and the leading indicators haven't moved. They're sequential, not interchangeable.

Can AI call-coaching tools replace 1:1 coaching in 2027? No — they amplify it. Tools like Gong, Chorus, and Salesloft surface the moments worth coaching and track behavior change at scale, which makes your call reviews sharper and faster. But the conversation that rebuilds belief and locks a commitment is still a human one. Use the tool to find the lesson; deliver the lesson yourself.

What if I only have time to coach one thing? Pick the single skill with the highest leverage on the rep's number — usually discovery quality or a specific objection. Depth beats breadth: one skill coached to mastery moves more deals than five skills touched lightly.

Bottom Line

The turnaround move that matters is diagnose, then coach one thing: separate skill, will, knowledge, and system, secure an early quick win to rebuild belief, and drill a single focus skill on a weekly cadence through a 30/60/90 plan. Measure leading indicators, not lagging quota, and stay honest — if a fair, documented effort doesn't move the rep, the kindest decision for everyone is a clear performance plan, not another quarter of vague coaching.

Related on PULSE

• [Top 10 Questions to Ask a Struggling Sales Rep During a 1-on-1](/knowledge/cg0909)
• [How do you ask a question that helps a rep identify the moment they lost control of the sales conversation?](/knowledge/cg0890)
• [Top 10 questions to refine a rep's sales pitch for different stakeholders](/knowledge/cg0887)
• [Top 10 questions to assess a sales rep's time management habits](/knowledge/cg0877)
• [Top 10 questions to identify a rep's biggest sales roadblock](/knowledge/cg0875)
• [Top 10 questions to boost a sales rep's negotiation skills](/knowledge/cg0871)

Sources

• Harvard Business Review — The Best Sales Managers Don't Chase Revenue
• Gong Labs — Sales coaching research and call analytics
• RAIN Group — Sales Coaching insights and research
• Sales Hacker — How to Coach Underperforming Sales Reps
• Sandler — Sales coaching methodology
• Winning by Design — Sales coaching and frameworks
• The GROW Model — coaching framework overview (MindTools)
• Salesforce — Sales coaching guide

*Sales coaching for turning around an underperforming sales rep — how to coach a struggling rep, sales manager coaching guide, rep turnaround framework, a 30/60/90 underperformer plan, and a coaching playbook for 2027.*