Guilty pleasure: forcing role-play to build confidence

Your sales team has the tools. They know the pitch. The CRM is full of leads. So why are half your reps still missing quota? Randy Wilinski spent 15 years building high-performance sales teams before joining our training team at Sales Gravy. His answer to this question cuts through the usual explanations about territory problems or skill gaps. The real issue? Most sales leaders are managing activity instead of developing people. They're applying pressure instead of addressing the mental blocks that sabotage performance before reps ever pick up the phone. The Real Problem Holding Back Sales Teams Walk into any sales bullpen and you’ll hear the same beliefs on repeat: “I’m not good at cold calling.” “Nobody wants to hear from me.” “I don’t know if I can hit these numbers.” Most leaders dismiss this as an attitude problem or lack of confidence. So they fire up the team with a motivational speech, send everyone back to their desks—and nothing changes. Here’s what’s being missed: These aren’t attitude problems. They’re belief systems that determine behavior. And behavior determines results. Nobody was born knowing how to sell. Your top performer didn’t start with the ability to handle objections or close deals. They learned it. But the reps who believe they can’t learn it won’t put in the work to improve. They’ll make half the calls, avoid the hard conversations, and prove themselves right. The real work of building elite performers is getting inside your reps’ heads and rooting out the thought processes that are killing their performance. That’s where true coaching separates managers from leaders. Why One-on-One Coaching Unlocks Growth Group training builds skill, but addressing mental blocks requires one-on-one coaching—where you can dig into patterns, ask uncomfortable questions, and challenge unhelpful thinking. Why does this rep always sabotage themselves right before closing a big deal? Where did this idea that "people don't like being sold to" come from? What past failure is creating this blind spot? Good coaches shine a light on the patterns that people fail to recognize or flat-out avoid. They name the behavior that’s been there all along, but no one wanted to confront. Awareness alone doesn't create change. Your rep can have that breakthrough moment where they realize they are the problem, and still fall back into the same habits. Real coaching means holding people accountable to the change they commit to making. It means checking in, following up, and not letting them slide back into old patterns when things get uncomfortable. That’s the difference between feel-good conversations and actual performance improvement. The Coaching Gap in Sales Leadership Most sales leaders don't actually coach. They manage activity, review numbers, and deliver pep talks. But managing metrics does not build high-performance sales teams. Developing people does. Coaching starts with curiosity. It means sitting down one-on-one and asking questions that uncover what is really holding a rep back. Not "why didn’t you make enough calls?" but "what made those calls hard to make?" Sometimes the barrier is a belief. Other times, it is a communication issue between the rep and the leader. If you do not understand how each person communicates and processes feedback, you will keep missing the mark. When you tailor your coaching to match how a rep thinks and responds, conversations become more productive and performance starts to shift. That is how coaching turns from another meeting on the calendar into a catalyst for real growth. Creating an Environment Where New Reps Actually Develop The best thing you can do for your team is lower the pressure on outcomes and increase the focus on process. This doesn't mean accepting mediocrity—it means being relentless about the activities while being patient with the results. Your new reps are going to struggle. It’s a reality you have to accept,