How Coaching Transforms Sales Performance and Culture (Ask Jeb)

Dennis from Chesterfield, Missouri, wants to know if sales coaching truly moves the performance needle, especially when shifting from transactional approaches to more consultative selling. Below are the key insights from our conversation on why coaching matters, how it boosts sales and culture, and what leaders should do right now to make it happen. Why Sales Coaching Is Essential Sales is a skill position. Even the best reps lose their edge if they’re left on their own for too long. Much like elite athletes, sales professionals need ongoing input to fine-tune their mechanics, recharge their motivation, and keep small errors from turning into big problems. Coaching can be the difference between a rep who has plateaued and one who keeps climbing—because it provides immediate, personalized feedback when it counts most. From Knowledge Acquisition to Knowledge Application Training is vital for learning new strategies, product details, and selling techniques, but it doesn’t guarantee that anyone will actually use those ideas. That’s where coaching comes in. A coach helps each individual absorb and adapt those lessons to their unique style, role, or territory. Research shows that simply sending people to training without one-on-one follow-up leads to a big dip in retention and performance. But when coaching supports training, skill application soars—along with results. Leading, Managing, and Coaching: The Three Pillars of Leadership Sales leadership has three core pillars. Leading sets the emotional vision of where the team is headed. It's getting people emotionally connected to a future state. Managing is driving the step by step processes that execute strategy. Coaching is developing your people to execute at a high level. It is the force that keeps every member of the rowing in the right direction. Think about it this way. 90% of strategy (leading) is execution (managing) AND 90% of execution is people (coaching). Everything depends on people which is why you can’t afford not to coach. Sales Leadership and Coaching Priorities Leaders who prioritized weekly one-on-ones, real-time one-to-one coaching, and rigorous sales pipeline reviews consistently deliver better results and productivity. One of my top clients reconfigured its leadership approach with inside sales reps, focusing on call-by-call coaching in real time. While the broader industry shrank, this company grew by over 20%. The common thread? Leaders were present. They weren’t waiting for problems to surface; they intervened early and often, guiding reps through each challenge. Why Simply Showing Up Makes a Difference Leaders sometimes fear that sitting with their reps will feel intrusive, yet just being there raises performance. When a coach or manager listens in on a sales call or rides along on an outside sales appointment, reps immediately sharpen their focus. They’re more likely to use proven techniques and avoid shortcuts. Even better is when the leader offers coaching in the moment—helping the rep pivot if the call starts going sideways. Catching issues before they snowball is how reps maintain a consistently high standard of performance. The Power of Being Side by Side One sales organization I work with discovered, after a big dip in sales productivity, that none of its sales managers were spending time on the floor. Rather than spending time on the sales floor coaching, the leaders were in their offices, behind closed doors grading calls. As soon as the managers started actively coaching—right next to their people, live—the entire team’s win-rates rose sharply. True coaching works best in real time, because your rep can implement what they just learned to get better on the next call. The Culture Shift from Transactional to Consultative When a coach is on the floor or in the car, they can see how a rep handles difficult questions, responds to objections, or frames value to a hesitant buyer.