How to transform your sales coaching from ad hoc to structured

BY:  Rebecca Herson
August 5, 2021
Updated on May 13, 2024

Table of Contents

Having a structured coaching process can make a huge difference to your salespeople, and your sales results. Many companies, however, have an ad hoc approach, coaching on the fly, during pipeline meetings or whenever something comes to mind. This lessens the impact of sales coaching compared to a systematic approach, and less than using a dedicated sales training platform.

Sales Hacker recently hosted a Webinar with Ariel Hitron of Second Nature; Susan Greenberg, global pre-sales readiness lead at SAP; and John Hsieh, founder of Scale GTM to discuss how to convert an ad hoc sales coaching program into a structured program built to succeed.

Check out a few of the Webinar highlights below.

Building a great sales coaching program starts with data

Managing the massive amount of data your company has about its deals is the first step in building a great sales coaching program. By using data-driven sales coaching, your salespeople could increase your open pipeline by up to three times as much.

One of the biggest advantages that data-driven sales coaching provides your salespeople is confidence. Knowing everything about a product helps your salespeople when it’s time to talk about it with customers. As your sales reps talk more and more about a product, they build confidence around the product, helping to propel their sales.

One way to build confidence is through organizing the vast amount of data that a company has about a product or service. Having knowledge about what the company offers allows your salespeople to talk about it more easily, giving them the conversational readiness they need.

The most important questions surrounding data organization include, as John Hsieh said: “How do we start to help sellers organize this information so that they’re ultimately conversational ready? As an enablement professional for the past decade, it’s really helping to organize around what do reps need to know, what do they need to show, and then, finally, what do they need to say?…The role coaching sales leaders plays in this, it’s literally where the rubber meets the road. It’s taking all three of those things and connecting the dots.”

Learning from mistakes in a safe space

Along with being confident when talking about a product, a willingness to learn from mistakes plays an important part in the sales coaching process. In fact, making mistakes early on can be a good thing.

“When you’re talking about learning, you really learn better from your mistakes,” Greenberg stated. “If you do everything absolutely perfectly all the time, then you would never learn anything. You really remember when you mess up.”

Sales coaching helps to create the space needed for your salespeople to practice sales calls and make mistakes without the fear of making a mistake with an actual customer. This allows your salespeople to make those mistakes and improve upon their calling skills before the sales call. This confidence booster is essential to success.

“Sales coaching is all about creating that safe space and environment for people when they don’t yet have that competence to do the practice and to make those mistakes in that safe environment with their coach, as opposed to having that disaster happen for them because they thought they were ready but they really didn’t have the confidence,” Greenberg observed.

Second Nature and its AI sales enablement and coaching program, Jenny, provides vital practice that your salespeople need to improve their calls without having to make these mistakes when talking directly to the customer.

Setting aside time for coaching

In many cases, sales managers put off coaching to focus on the sales pipeline, since it’s most urgent. In fact, with most companies “urgent always takes precedence over the important,” Hitron said.

Keep in mind, discussing the pipeline is important, but you also need to set aside dedicated time for sales coaching, both now and in the future.

The best way to approach this is to have a goal in mind; for instance, whether it’s opening more opportunities or closing larger deals. Then it is a matter of breaking it all down into the components necessary to achieve that goal, such as asking the right questions, handling any objections, and knowing the product.

“Objection handling is one of these things that, it’s so critical to help new reps, or as they enter new markets or new industries, etc., to get a handle on,” Hsieh said.

How much time should you spend coaching your salespeople?

The amount of time you spend coaching your salespeople is also important, including on a weekly, monthly, or yearly basis.

“We actually started with what was our objective for coaching,” Greenberg said. “For us, the first one that we started with was experts who already had the technical ability and knew the technical product in and out.”

Then SAP developed an in-person class where sales leaders went through and collected objections and then roleplayed back and forth. “And as soon as people got into that roleplay with a real person, they realized ‘this is much harder than I thought that I was going to be able to do,’” she added.

This process highlights the need for a mechanism to practice in a safe environment. Using Second Nature, SAP developed a system where salespeople could practice on their own time on a regular basis.

This strategy produced better results, according to Greenberg. “Even when they thought they were confident and had all the technical abilities, the practice saw a dramatic increase in people’s comfort and their willingness to go and take it on.”

To help determine the impact that sales coaching has with a company’s salespeople, Second Nature published a sales coaching survey that gives insights on the sales coaching process.

How automating with a sales coaching platform can help your company scale

Another important consideration is allowing your sales managers the time they need to become familiar with any new messaging before sending them out to work with your sales reps.

“The question is, can that sales manager actually coach the sales rep for the new messaging when they’re just learning it themselves?” Greenberg asked.

Automation plays an important role in this initial practice, allowing companies to better scale through a more consistent process with clear goals for team members.

“Coaching is continual encouragement to help them figure out themselves how to be better,” Greenberg added.

Mixing sales coaching with an automatic program is also a good thing, as it allows both sales managers and their salespeople to practice before even making the first call to a customer. You must also keep in mind that having an established sales coaching program doesn’t mean that automation isn’t a necessity.

“Even with the investment that SAP made in the pre-sales academy and having an entire staff or faculty who were trained to be able to do this coaching, we found the need for automation was there,” Greenberg explained. “We found that the academy grads actually preferred to practice with an artificial intelligence automation, because it was nice getting back to that safe environment and not be in the pressure where they were sitting there with that academy faculty at the certification.”

Using Jenny — Second Nature’s AI sales coach, your company can give your sales managers and salespeople the practice they need to improve sales conversations.

Watch the full Webinar for more on how to best develop your company’s sales coaching program, as well as how using Second Nature can help streamline this process.


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About the author

Rebecca Herson

Rebecca is head of marketing at Second Nature.

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