(Last updated November 17, 2025)
Most problems in sales don’t come from a lack of skill. They come from mixed messages, weak coaching, bad territory setups, or tools that get in the way. When leaders take a breath and look at the real issue, they stop guessing and start solving.
Before you roll out another training, slow down and check these 7.5 things.
Key Takeaways
- Training only works when the foundations are solid
Many teams look to training when performance drops, yet most issues come from unclear expectations, weak coaching rhythms, and inconsistent messages across the organization. When leaders fix these first, training becomes more effective and easier to apply in daily work - System problems create performance gaps that no workshop can repair.
Territory design, broken tools, slow processes, and policy barriers shape how reps perform. These structural issues block momentum regardless of skill level. When leaders repair the system, reps have the space to execute at a higher level. - Delegation creates a culture of trust and autonomy.
Skill is only one piece of the performance equation. Motivation, leadership alignment, resource access, and workflow design also influence outcomes. Teams save time and budget when they identify which category the real problem belongs to before building a training plan.
1. Unclear Expectations
When reps don’t know exactly what “good” looks like, you’re starting from behind. Managers often assume everyone understands, but they do not. Clear expectations mean a rep knows the target behaviors, the “quality” of calls or meetings, and what success looks like in each step. If you skip this, training is like giving someone a tool without telling them what to build.
2. Inconsistent Coaching
Training feels like action. Coaching makes action happen. Research shows reps who get dedicated coaching see significantly higher revenue growth than those who don’t. If managers aren’t coaching regularly, what the rep learned in a training session won’t stick—or worse, they’ll revert to what’s comfortable.
3. Mixed Signals
If marketing wants one thing, leadership another, and the CRM pushes a third message, your team is confused. Confusion kills momentum. Reps stop. They drift. Training won’t solve this if everyone is pulling in different directions.
4. Bad Territory or Account Structure
A top rep can’t fix a territory that’s built to lose: too few accounts, too far apart, misaligned resources. If the setup is broken, training can’t patch that hole. Fix the structure first, then see if training helps.
5. Tools or Processes That Slow People Down
Even a great rep will struggle if the CRM is a mess, if logging calls takes longer than making calls, or if essential data is missing. Training won’t fix clunky tools or broken processes—it will just frustrate reps further.
6. No Time to Practice the Right Behaviors
You learn to sell (and re-sell your skills) by doing. If you don’t give reps time to rehearse, reflect, and improve, training becomes a checkbox. Studies show high training-content retention only when reinforced. sales-alliance.com+1If you’re scheduling training but not carving out time to practice, you’re wasting money.
7. “Hill” Blockers
These are the structural blocks reps can’t fix, policies that contradict how you sell, access delays, data issues, and workflows that were never designed for your model. If you have “Hill” blockers and you still train, you are asking the rep to climb a mountain with no rope.
7.5 Low “Will” (Not Low Skill)
Sometimes the issue isn’t that the rep can’t sell; it’s that they don’t want to, or they don’t believe they can. Will issues look like: low urgency, weak ownership, unclear purpose. These aren’t fixed by skill training; they’re fixed by leadership connecting the work to win, by coaching and accountability .Research shows training alone—without reinforcement and will alignment—often fails to deliver. The Sales Collective+1
Why Skill Gaps Are Rarely the Main Problem
Look: Skill gaps exist. But when everyone is struggling, that’s rarely the issue. Skill issues tend to show up in a small number of reps. They’re behavior-specific, fixable with coaching/training. When the whole team is underperforming, you’re looking at system, structure, clarity, or leadership issues, and training alone won’t fix that.
The Bottom Line
You wouldn’t give medicine without diagnosing the illness. So why do we keep giving training without checking what’s wrong first? The companies that win aren’t the ones who train the most—they’re the ones who fix the right problems. Before you schedule another session, ask:
- Are we fixing the cause or the symptom?
- Do we know whether it’s a Skill, Will, or Hill issue?
- Have we slowed down long enough to actually understand the problem?
Because the most expensive training is the training that was never going to work anyway. Your teams don’t need more workshops. They need fewer things blocking them.
Ready to Fix What’s Really Holding Your Sales Team Back?
Most teams don’t need another workshop. They need someone who can cut through the noise and find the real problem fast.
If your reps are stuck, if performance is uneven, or if you feel like you’re pouring money into training without seeing change, let’s fix that.
AT CMT, we help sales leaders:
- Pinpoint the true root causes behind stalled performance.
- Separate Skill issues from Will issues from Hill blockers
- Uncover system and process problems that training will never fix.
- Build simple, practical fixes that drive real results.
- Save time, budget, and energy by stopping the guesswork.
If you want clarity—not another expensive “maybe this will work” workshop—you’re in the right place.
Get a Clear Diagnosis Before You Invest Another Dollar
Click below to schedule a quick call. No pressure. No fluff. Just straight answers about what’s really going on—and what to do next.
→ Schedule Your Performance Diagnosis Call
Because training isn’t the solution. Knowing the real problem is.
Frequently Asked Questions (FAQs)
1. How do I know if my team really needs training?
Look for behavior patterns. If only a few reps struggle, a skill gap may be the cause. If most of the team is stuck, the issue is usually structural or coaching-related. Training helps when the basics are already clear and consistent.
2. What is the difference between a Skill, Will, and Hill problem?
Skill problems relate to ability. Will problems relate to motivation and confidence? Hill problems involve system or structural barriers that reps cannot control. Effective leaders identify the right category before choosing a solution.
3. How often should managers coach to support training?
Weekly coaching sessions create steady progress. Short, consistent conversations help reps apply what they learned. When coaching becomes predictable, performance becomes more stable across the team.
4. Can training still help if our tools and processes are weak?
Training may provide temporary energy, but it will not create lasting change. Reps will default to old habits when systems slow them down. Fixing the workflow first allows training to stick.
5. What is the most common reason training fails?
Training fails when leaders skip diagnosis. Without clarity about the real issue, teams invest in the wrong solution. A clear performance diagnosis helps leaders target root causes and avoid unnecessary spending.
6. How do I spot low Will in a rep?
Common signs include low urgency, inconsistent follow through, avoidance of difficult tasks, or a belief that effort will not lead to better results. These indicators need leadership support, accountability, and stronger alignment, not more skills training.
7. What should I fix first if my team shows several issues at once?
Start with clarity. Reps need to know what good looks like, how they are measured, and what leadership expects. Once clarity is in place, coaching, systems, and training become easier to implement.
8. When does a performance diagnosis make the biggest difference?
A diagnosis helps most when teams are underperforming, when leaders see uneven execution, or when repeated training has not delivered meaningful improvement. It gives you a simple map of what to fix, in what order, and why.
