Episode Details

I spent an afternoon at Ramsey Solutions in Tennessee with Jason Williams, Vice President of Sales for the EntreLeadership Division. What stood out wasn’t the size of the operation or the fancy building. It was walking into a room where sales reps genuinely wanted to talk to their leader.

Most sales floors feel like number factories. Reps avoid their managers. One-on-ones get rescheduled. And everyone wonders why performance stays flat despite “investing in our people.”

Sales leaders say coaching matters. They talk about developing talent. Then they spend their days staring at dashboards and asking why the team isn’t getting better.

Real sales coaching looks nothing like what most organizations call coaching. And after watching Jason work, I’m reminded why so few leaders actually get this right.

What Sales Coaching Actually Looks Like

Jason told me about one of his reps who started missing quota. Here’s what usually happens: Manager pulls up the CRM, points at red pipeline metrics, asks what happened. The conversation goes nowhere. Rep gets defensive, makes excuses, promises to work harder. Nothing changes.

Jason took a different approach. He asked about his rep’s life. Turned out he was stressed about buying his first house. That weight was bleeding into his work, affecting his confidence on calls, making him hesitant to push for commitments.

So Jason got into the field with him. He listened to calls. He rode along on appointments. He watched where deals were actually stalling. Then they debriefed what he observed. “Here’s what happens when pricing comes up.” “Let’s tighten how you handle that objection.” Zero mention of quota or pipeline metrics.

The rep turned it around because someone cared enough to understand what was broken and help him fix it.

That’s what coaching looks like. Managers react to outcomes they can’t change. Coaches focus on behaviors that create future outcomes.

Why Most Leaders Don’t Coach

The biggest barrier isn’t that leaders don’t want to coach. Most genuinely do. The problem is they don’t know what they’re looking for because they never see their reps in action.

Think about last week. How many discovery calls did you listen to? How many demos did you observe? How many customer meetings did you attend just to watch your rep work?

If the answer is zero, you’re coaching from spreadsheets instead of reality. You’re looking at lag indicators (closed deals, pipeline value, activity counts) and trying to diagnose skill gaps without ever seeing the skills in action.

Jason blocks time every week to observe his reps. He’s not there to supervise them or take over calls. Just to watch. Then the coaching becomes specific. He can say, “when that prospect brought up budget concerns, you deflected instead of asking questions,” instead of just “you need to handle objections better.”

You can’t coach what you don’t see. 

The second barrier is culture. In typical organizations, admitting weakness feels dangerous. You’re supposed to be confident, crushing it, always having answers. So problems stay hidden until they show up in the numbers.

By then, it’s too late to coach. You’re in damage control.

Creating an Environment Where Problems Surface Early

Jason builds what he calls a “safe space” for his team. When a rep is struggling, he starts the co