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Asking about pipeline status or deal counts is a "check-in," not coaching. True coaching involves diagnostic questioning about specific calls and strategies to improve rep performance. Without this developmental focus, top performers get frustrated and leave, while struggling reps fail to improve.
A successful pipeline generation culture is not built by a playbook alone. It requires leaders to be 'in the pit' with their reps weekly—inspecting, inspiring, and actively participating in calls. This difficult, hands-on coaching, which includes being vulnerable and getting rejected, is essential for demonstrating commitment and helping reps get unstuck.
Underperforming sales reps are not failures; they often lack proper coaching or strategic frameworks. Investing in their development can transform these reps from liabilities into consistent performers, saving the high costs associated with turnover and re-hiring.
A sales leader's job isn't to ask their team how to sell more; it's to find the answers themselves by joining sales calls. Leaders must directly hear customer objections and see reps' mistakes to understand what's really happening. The burden of finding the solution is on the leader.
Many sales leaders run pipeline reviews solely to extract information for their forecast. The meeting's primary purpose should be to help the rep understand what to do next. Effective coaching leads to closed deals, which in turn creates an accurate forecast naturally.
Instead of telling a rep to "book more meetings," analyze their process and identify the specific micro-step where they are failing, such as getting past the first 15 seconds of a cold call. Focus all coaching efforts exclusively on improving that single, specific action to fix the larger outcome.
Managing pipeline numbers is a lagging indicator of performance. Effective sales leaders coach on leading indicators: the specific activities and customer interactions happening at the deal level. They influence outcomes by asking "Why should the customer buy?" instead of just reviewing the forecast.
Sales managers often gravitate toward big deals with star performers, believing they are helping close revenue. However, their highest-leverage activity is coaching ramping reps on smaller deals, as this develops the entire team and prevents churn. This is a common but incorrect prioritization of activity over accomplishment.
For effective coaching, a manager should spend a half-day with a rep on three appointments. Afterwards, provide structured feedback: three specific wins to reinforce good behavior and three actionable opportunities for improvement. This tactical routine drives targeted and immediate skill development.
Effective coaching follows a three-step process: Identify a metric-based performance gap, validate the specific rep behaviors causing it, and then co-create a coaching plan focused on improving those behaviors, not just the lagging metric.
Many sales organizations mistake "coaching the deal" for actual coaching. This is merely reactive performance management. True coaching focuses on developing a rep’s core capabilities—like discovery or closing—which prepares them for any future deal, not just the current one.