How to Use AI to Supercharge your Sales Coaching Efforts

BY:  Rebecca Herson
March 1, 2021
Updated on September 4, 2023

Table of Contents

It’s that time of year when sales teams psych themselves up to meet the new sales goals. It’s always a challenge, but this year it’s even harder. The entire economic and business environment is uncertain and changing rapidly, and that’s a very tough field in which to drive sales. 

When sales enablement teams are given new targets to beat, they work hard to come up with new strategies to achieve these tasks. These strategies can include launching new products or versions, developing new messaging or sales methodologies, expanding into a new market, or adding more sales employees to grow the team.

While each of these strategies has potential for success, they need a very structured sales coaching system in place to reach their full potential. 

We recently held a webinar with Selling Power’s Gerhard Gschwandtner about this topic, which you can view here. Or simply continue reading…

Why you need structured sales coaching

Structured sales coaching stands in contrast to ad hoc coaching in that it’s systematic, focused on achieving specific results, and involves training sales representatives before they enter the field rather than giving ad hoc feedback on actual sales calls.

No matter how good your sales strategy, you’ll always need to bridge the gap between the theory and the execution. At the heart of every effective sales strategy lies a fluent, confident conversation between the sales representative and the lead, one that’s interesting and relevant to the buyer’s needs. That conversation is the key to driving revenue.

Structured sales coaching impacts the conversations that sales teams have on the ground by making them more focused. It may relate to mastery of product features, grasp of company messaging, or sales methodologies, but each aspect can be improved by structured sales coaching.

How to prepare to improve sales coaching at scale

There are a number of steps to building a structured and effective sales coaching program. First, you need to decide on a goal. There are many potential goals, like closing larger deals, expanding your sales pipeline, cutting the length of your sales cycle, and increasing your sales win rate. While it might be tempting to go for all of them, you could end up diluting the purpose of your sales coaching too much, so it’s best to focus.

Next, you’ll choose individual coaching scenarios within your goal, like breaking the goal of closing larger deals down to the scenario of selling to C-level executives and roll out those scenarios at scale. Each scenario can be divided up into specific conversations which are targeted for precisely this situation.

Finally, you’ll decide what to measure to track progress. You could use leading indicators like sales rep proficiency and confidence in sales pitches, or lagging indicators like the number and size of deals each rep is able to secure and the amount of revenue coming in.

The challenges to sales coaching at scale

Training sellers to hold these conversations can be challenging. There are four main options:

  • Top-down training, where the sales manager or sales enablement team deliver a presentation on your new messaging, product, or sales methodologies. The drawback is that once you reach a certain team size, it’s hard to communicate well with each seller and even harder to verify if they’ve understood. 
  • One-on-one training between the sales manager and the sales representative. This is ideal for training purposes, but sales managers lack the time to carry out in-person training for large teams. 
  • Managerial review for recorded sales pitches is great in theory, but again, managers don’t have time to send feedback, and employees quickly lose motivation when their pitches go unreviewed. Feedback also tends to be subjective and inconsistent. 
  • AI-powered sales simulations that allow each employee to practice their pitches privately and receive immediate, targeted, and consistent feedback that helps them improve their delivery. 

Tracking progress can also be difficult. Although there are a number of potential indicators, it’s often hard to reliably and objectively assess leading indicators, and lagging indicators are, by nature, lagging. By the time you discover that your sales reps haven’t quite mastered your new messaging, you’ll have potentially missed out on 6 months of better sales.

How Second Nature’s AI solution can help

This is where Jenny, Second Nature’s AI-powered sales training software, can help. Companies can create a realistic sales scenario for sales teams to use to practice their pitches.

The process is private, so no one feels nervous about making mistakes. As sales professionals conduct the conversation, Jenny asks leading questions to remind the user of key talking points that they missed, and at the end of the session she delivers targeted feedback that encourages the rep to try again to improve their score.

Second Nature’s Jenny reviews not just the content of the conversation, but also delivery points like the speed at which the user speaks, use of filler words, and how easy it would be for a prospect to follow the pitch. The AI solution provides consistency of feedback across the board.

Using an AI program also helps resolve challenges around tracking employee progress. The solution standardizes assessment to provide a baseline for measuring improvement, and includes a manager dashboard that allows comparison across teams and individuals and gives visibility into weak areas that need reinforcement.

Structured sales coaching at scale is the key to unlocking super sales

Effective sales coaching can bridge the gap between sales strategy and real revenue by enabling sales employees to carry out confident, engaging, and relevant sales conversations with leads. Choosing a goal, selecting scenarios, breaking them down into individual conversations, and measuring the results can help you build an effective structured sales coaching program, but rolling it out can still be challenging without the help of AI.

To learn more about how Second Nature’s AI can help you to provide effective, targeted sales coaching at scale, watch our Sales Coaching webinar with Selling Power’s Gerhard Gschwandtner.

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About the author

Rebecca Herson

Rebecca is head of marketing at Second Nature.

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