Structure, Preparation and Hard Data Form the Foundation for Effective Rep Coaching

September 4, 2019

Shawn Parrotte

Ask a sales rep what their manager wanted to hear about most in their last coaching or training session and there’s a good bet you’ll hear this response: “The deals I’m trying to close right now.”

Sales managers want to support their reps in getting deals across the finish line. But often, they do so at the expense of helping them build the skills they need for long-term sales success.

The importance of sales managers focusing less on deal coaching and more on skill coaching was a core topic in the recent webinar, The Surprising Truths About Effective Rep Coaching: Build Capability for the Long Term.

Here’s a look at some of the expert advice that featured speakers Joe Caprio, Vice President of Sales at, Matt Cameron, founder of SaaSy Sales Management, and Dylan Rushe, Sales Director at InsightSquared, had for sales leaders.

1. Managers, not reps, should set the agenda for sales coaching sessions #

The risk of letting a sales rep set the agenda for a one-on-one coaching session, according to Cameron, is that you’ll likely hear a report that’s “all unicorns and roses.” Reps may be inclined “distract you with shiny objects” to avoid an uncomfortable discussion of where they’re struggling.

Cameron offers a framework for setting an agenda and taking a more structured approach to training or coaching sessions with reps.

Matt Cameron’s Sales Coaching Tip: When setting an agenda, a good starting point can be addressing these questions: “Is the sales forecast believable? And how do we fill the gaps?”

2. Managers must prepare for coaching sessions like client meetings #

Sales managers need to come to coaching sessions ready to talk specifics with reps, Rushe said. “Preparation needs to be prioritized,” he explained, emphasizing that managers should put as much thought and care into planning for coaching sessions as they would for client meetings.

Following that tip from Rushe, Cameron added that sales managers can help ensure the time they schedule for coaching is used effectively by telling their reps in advance, “If you keep your CRM data up to date, and your opportunity records clean, I promise that in our meeting I’ll never ask you questions like, ‘What did you get up to last week?’”

Dylan Rushe’s Sales Coaching Tip: Scheduling dedicated time on the calendar for 1-on-1 meetings with reps to avoids the tendency of “on the fly” coaching that often doesn’t stick.

3. Managers need to use real data to help reps improve performance #

Rushe said he can’t emphasize enough how a tailored and data-driven approach to coaching has much more impact — and credibility — than a subjective approach.

He noted how tools like InsightSquared’s AI-powered revenue intelligence software and’s conversation intelligence platform can help sales managers deliver more individualized coaching by allowing them to drill down on data to identify trouble spots in reps’ performance.

Caprio expanded on Rushe’s message by explaining how is valuable for surfacing “coachable moments” in sales calls. That type of data insight helps managers deliver targeted skill coaching to reps that can lead to an increased win rate and higher quota attainment, instead of just providing tactical advice designed to close pending deals.

The platform allows sales managers to pinpoint whether an issue is unique to one rep, or an indicator of a broader problem across the sales team. With the data insights and capabilities like scorecards that provides, sales leaders can create custom coaching plans specific to your reps and their challenges.

Joe Caprio’s Sales Coaching Tip: Use data to build personalized, structured coaching plans that can help to elevate your whole team’s performance.

Watch the full webinar to get more expert tips for increasing sales coaching effectiveness. You’ll also learn more about how AI-powered solutions like and InsightSquared can make sales coaching less subjective, feedback more actionable, and progress more measurable.

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