Your Underperforming Rep Has Either a Skill Problem or a Will Problem. Here's How to Tell the Difference.

When a rep starts missing their number, most managers reach for the same playbook: they add more training, more ride-alongs, more pipeline pressure. Sometimes it works… but often it doesn’t. 

The intentions are good, but that doesn’t mean the diagnosis is correct. 

Underperformance almost always traces back to one of two root causes. Either the rep can't do what's required (a skill problem), or they could do it but aren't (a will problem). These two causes look similar on the surface, typically showing up as missed quota, stalling deals, and low activity. 

However, they require completely different responses. Coaching to the wrong issue (e.g. coaching a rep for skills when they actually have a will problem, or vise versa) not only doesn't fix the problem, but can often make it worse. 

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What a Skill Problem Looks Like

A rep with a skill gap doesn't know what they don't know. They're putting in effort and following the process as they understand it—but something in their execution is breaking down at a specific, identifiable point.

Here are some signs that you’re dealing with a skill problem: 

• Performance is inconsistent in a patterned way. They struggle in the same stage, with the same objection, or in the same type of conversation every time.
• They can't articulate the process. Ask them to walk you through how they handled a specific call or deal stage, and the explanation is vague or misses key steps.
• They respond well to coaching. Show them what good looks like and they can replicate it. The gap closes with practice and feedback.
• Tenure doesn't match performance. A newer rep underperforming on complex enterprise deals may simply need more practice, not more motivation.

The coaching response to a skill problem is specific, behavioral, and observable. You identify the exact behavior that's breaking down. It might be discovery questions that don't uncover real pain, deals without confirmed next steps, proposals sent before the buying committee is mapped. Then, you focus every coaching conversation on that one thing until it improves. Telling a rep to "be better at discovery" isn't coaching. Walking through a real call and showing them the three moments where they left value on the table is.

What a Will Problem Looks Like

A will problem is both harder to see and harder to fix. A rep with a will problem often knows exactly what to do. They have the skills and they’ve done it well before. But somewhere along the way, a disconnect has emerged between the daily behaviors required and the outcomes those behaviors are supposed to create.

Here are some signs you are looking at a will problem: 

• Performance has dropped from a previous baseline. They used to hit their number. The skills are still there, but something has shifted.
• Activity is down but execution on active deals is fine. They're not making the calls or building the pipeline, but when they do engage, they're capable. The issue is initiation, not ability.
• They've become disengaged in team settings. This looks like less energy in the room, shorter answers in 1:1s, or less investment in deals they haven't already started.
• The work has disconnected from what they care about. When you ask what they're working toward (professionally, financially, etc) they either don't have an answer or it doesn't connect to what they're being asked to do.

The coaching response to a will problem starts with a different question entirely: what does this rep actually want? Not what the company wants from them—what they want for themselves. Are they trying to hit a comp milestone? Get promoted? Buy a house? Prove something? The more specifically you can connect their daily behavior to an outcome they genuinely care about, the more traction you get. A rep who understands why showing up to prospecting blocks matters to their own goals will outperform a rep who's doing it to avoid a hard conversation with their manager.

The Misdiagnosis Tax

The most common mistake is treating a will problem like a skill problem. Sending a disengaged rep to training, rolling out another methodology, adding more inspection to their pipeline—if anything these “fixes” are going to exacerbate the problem. The rep already knows what to do. More instruction doesn't address the real issue, and it signals that you haven't noticed what's actually going on.

The reverse is less common but equally damaging: treating a skill problem like a will problem. Motivational conversations with a rep who genuinely doesn't know how to run a good discovery call leaves them more confused and less confident, not more energized.

The diagnosis has to come before the coaching. And the diagnosis comes from two places: Data around which what’s changed or broken down, and a direct conversation that actually surfaces what the rep is thinking and feeling.

The First Question to Ask

Before your next 1:1 with an underperforming rep, ask yourself: do I know why they're underperforming, or do I just know that they are?

If it's the latter, the 1:1 is a diagnostic conversation first. Look at where in the funnel performance is breaking down. Ask about a specific deal, call, or week, and listen for whether the issue is execution or engagement.

Get that right and everything else follows.

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